As you may recall, I teased a future live event to round out the content flywheel. That day has come. Premium subscribers will receive a private link to join us live, along with access to a replay for those unable to attend.

With the Schedule III hearing right around the corner, this feels like the right moment to level-set before the next chapter begins.

True to form, SUNDAY SESH will treat live events differently. No shade, but most podcasts tend to be either reactionary—getting someone’s view after an event has already happened—or proactive, but not timely or broad enough to connect the dots.

We’re bringing together some of the sharpest minds in cannabis across regulation, capital markets, brands, and distribution at the same time. These executives have spent years on the ground building businesses, allocating capital, and navigating policy. All day, every day.

Together, I believe that creates a richer mosaic than any one voice can provide.

More details soon, but for now hold the date. In addition, we will be answering questions sent in ahead of time.

To join us, subscribe.

Subscribe now

Today’s SUNDAY SESH focuses on one category sitting directly in cannabis’ crosshairs—the $35BN U.S. cold and flu market.2 And it’s not hard to see why: endless pharmacy aisles filled with ancient syrups, pills, sprays, nutraceuticals, and homeopathic remedies that promise many things but mostly do none as your body does the real work.

That matters—especially as cannabis sheds its 100+ year archaic stigma. Whether it’s HHS’ groundbreaking analysis under Biden, Trump’s push to reschedule, or the decades of independent medical research, the conclusion is clear:

Cannabis is real medicine.

For 55+ years, cannabis as a Schedule I drug meant the government claimed it had no accepted medical use. Somehow they ignored thousands of years of documented history, including in our own country. More importantly, they ignored the countless stories from pop culture and people just like me who spent decades watching real people find real relief.

Even for the common cold and flu.

When it comes to cannabis, SUNDAY SESH tries to bridge Wall Street and Main Street: how the industry will evolve, and how real-world experiences can change minds and standards of care. Combined, we paint a vision for the future.

So let’s pull out the terpy RSO, maybe pour a hot cup of cannabis-infused tea, and dive deep on another hill we’ll die on: cannabis is coming for OTC cold and flu. And it’s my bet Big CPG is asleep at the wheel after one too many doses of NyQuil.

Welcome to SUNDAY SESH.

Subscribe now

2/WHAT IS THE COMMON COLD?

Before we dive into the thesis, a quick disclaimer: I am not a doctor, and these are not recommendations. But I do have reps: I was one of the 1-in-15 kids who needed tympanostomy tubes, not once but twice before age 10. My son also needed tubes—not once but also twice before age 10. So let’s just say I know my way around the ENT medical complex.

The common cold is exactly what it sounds like: common. It’s a viral infection of the upper respiratory tract, usually centered around the nose, throat, and sinuses. Symptoms are familiar: runny nose, congestion, sneezing, sore throat, cough, watery eyes, headache, low-grade fever, and that general “I feel like shit” malaise made worse by terrible nights of sleep.

The flu is different, but the experience rhymes. Influenza is also a viral respiratory illness, but it usually hits harder and faster. Putting aside Rx antivirals like Tamiflu, the consumer playbook is still mostly symptom management. And OTC meds are virtually identical to what you'd reach for with a cold. Same molecules, different box.

When you get these bugs, the virus isn’t “stuffing” your nose with mucus. Instead, infected respiratory cells release inflammatory mediators, including cytokines and chemokines, which call immune cells into the area and turn up local inflammation. This inflammatory cocktail is the source of the misery.

To state the obvious, what we reach for in the medicine cabinet is not curing the underlying virus. It helps alleviate symptoms as the virus naturally runs its course.

Even the claims of relief are spurious. Recently, the FDA unanimously concluded as much—finding no efficacy for oral phenylephrine, a main active ingredient found in over 250 OTC cold meds like Sudafed PE, DayQuil Severe, NyQuil Severe, and Tylenol Sinus.

This is critical to digest.

3/BUYER BEWARE

Regardless of questionable benefits, consumer feedback on OTC cold meds is universal: either you feel like a zombie or you feel wired. And therefore, you can’t stay awake or you can’t sleep.

For me, this “ping-ponging” was all too familiar growing up. As a kid, I vividly remember turning into a fucking werewolf after taking these drugs before bed. I couldn’t sleep, which left me feeling worse the next day. We’ve all been there.

To avoid that, today tens of millions of adults reach for drugs like NyQuil—a potent cocktail that includes Doxylamine (antihistamine) and ethyl alcohol (booze). This product basically puts you the fuck down, leaving many groggy. Why? Because doxylamine has a long half-life of ~10-12 hours. Not to mention, many products are still loaded with Blue No. 1 and Red No. 40 food dyes. (Hey Big CPG: wake up, you sell medicine in 2026.)

Still, these OTC drugs carry meaningful risks. Many products are “stacked” with multiple active ingredients, where patients can misdose or unknowingly combine drugs that interact with prescriptions. In addition, regulators have spent decades playing an endless game of “whack-a-mole” to ensure CVS isn’t pushing meth disguised as a cold remedy.

Anyone remember Sudafed’s “Medicine Head” commercials from the late ‘90s that promised alertness?

If you don’t, the upshot was that Sudafed contained pseudoephedrine, which later became tightly controlled because it’s a precursor to methamphetamine.

Lovely. No wonder I couldn’t sleep.

4/LET’S SIZE THIS MARKET

The addressable market is massive because "cold and flu" is not one category. It is a bundle of overlapping symptoms: cough suppressants and expectorants, antihistamines, decongestants, nasal sprays, and multi-symptom combinations (like NyQuil). Plus, it includes close adjacencies—like pain, fever relief and sleep—that customers often reach for when they get these bugs.

These drugs are the top two reasons why consumers still go to drug stores. Next time you walk into a CVS or Walmart, check out how much real estate the cold, flu and pain aisles cover. It’s massive.

Takeaway? This is a giant $35BN U.S. market.

5/ ECS UNLOCKS REAL SCIENCE

The cannabis-for-colds argument is not just “I took a gummy and felt better.” That may be where the idea starts, but the better question is why it might work at all. Beyond the sedation use-case to get better sleep—one of the main reasons why medical patients turn to cannabis—the biology runs deeper.

The answer likely lives inside inflammation, immune signaling, and the endocannabinoid system (“ECS”). We’ve discussed this in a prior SESH.

Early research is promising. Studies suggest cannabinoids may interact with inflammatory signaling pathways that are relevant to cold and flu symptoms. CB2 receptors, which are concentrated in immune-related tissues and cells, appear to help modulate the immune response. Not by turning inflammation off, but by acting more like a brake when the response becomes excessive.

A 2021 systematic review found cannabinoids—especially CBD, CBG, and CBD+THC combinations—often reduced inflammatory cytokines in animal models, while THC alone was less consistent. A separate lung-cell study found CBD-rich cannabis extracts reduced IL-6 and IL-8, two cytokines tied to airway inflammation and immune response.

On the antiviral side, the research is earlier and less proven but still relevant. A 2023 review summarized antiviral signals from hemp cannabinoids around viral entry, replication, and immune response. And CBD showed enough mechanistic activity to be tested in mild/moderate COVID, though the randomized trial did not show a clean benefit.

So the honest read: the biology is real, but the clinical bridge is unfinished. Schedule III classification should help close that gap. I’ll drop some relevant existing research in the comments to show what’s already been done.

Call it a hunch, but I’m wildly optimistic.

6/ WEED UNLOCKS BRO SCIENCE

“It’s good for the flu.” — “Legalize It” // Peter Tosh (1976)

Every great cannabis use-case typically gets exposed by “bro science” influenced by pop culture. And consumers don’t wait for white papers when they feel like shit. Peter Tosh, Bob Marley, Willie Nelson, Dr. Dre, and Cypress Hill carried the message through music. And movies like Caddyshack, Friday, Dazed and Confused, Half Baked, and Dallas Buyers Club only reinforced it.

That’s always been the cannabis playbook. The culture finds the use-case first. Science shows up later. Regulators show up last.

If we step back, OTC cold + flu meds really come down to two distinct use cases:

1. Reduce symptoms, which as noted is often spurious; and

2. Aid sedation to force you to ignore them.

That creates two very interesting seams: daytime symptom relief, and sleep.

The sleep angle should be obvious. I’ve previously discussed that global consumers have already figured out cannabis—like popping a gummy—can be more efficacious, and potentially safer, than popping an Ambien (Rx / zolpidem) or a Unisom (OTC / doxylamine succinate). And for millions it’s not even a debate anymore. Edibles across regulated and hemp exceed $8-12BN just in the U.S.

The $5BN OTC multi-symptom market—like NyQuil—already sells sleep. So if cannabis is already nipping at sleep aids when you’re not sick, nighttime cold meds are an obvious next bite. Especially since gummies cost ~$1.25-$2.00 per serving, which is on par with OTC alternatives.

The daytime side—relieving symptoms while you’re awake—is also where I’m optimistic. But I recognize the potential controversy given cannabis’ main cannabinoid—THC—is “intoxicating.”

On one hand, we’re forced to work through colds while dealing with “medicine head.” And millions of Americans already consume medical cannabis during the day. On the other hand, no one wants to show up stoned to a Board meeting. Including me. Cannabis and daytime don’t work for my lifestyle, ever.

So this is where I think the future gets interesting: micro-doses of THC (or none at all), complemented by more aggressive dosing of non-intoxicating cannabinoids like CBD and CBG. These minors may knock the funk out of the cold without knocking you out of your day.

And if you’re just too sick to work, then all bets are off. At that point, you just want relief—something that calms the body, helps you rest, and maybe lets you doze off during the day.

The point is simple: the market already exists. Consumers just might not realize cannabis belongs in the conversation. Folks like me—who’ve been relying on cannabis for decades to battle these bugs—will help light the path.

Think of the DayQuil || NyQuil combo. But made with cannabinoids.

7/FIN: CANNABIS IS A PERFORMANCE TOOL

True to form, I eat my own cooking. I’ll keep my personal routine high-level because this isn’t medical advice, and everyone’s body reacts differently. But when I’m sick and reaching for cannabis, I generally care about four things: quality, full-spectrum effects, form factor, and strain—in that order. Whether I’m trying to sleep or function.

My preferences have been further refined as the “green wave” spread. More access to more products from world-class teams has let me dial in my own standards of care across multiple major and minor cannabinoids, many of which are non-intoxicating. If you’re interested, I’ll drop the full “when I’m sick” stack in the chat— what I use, when I use it, what I avoid, and why.

To conclude, the status quo OTC cold and flu market is ripe for change. Existing products are ancient, potentially dangerous, and provide a mediocre experience at best. Even the FDA has started saying the quiet part out loud: most of this stuff doesn’t work.

Cannabis might not be the panacea, but neither is NyQuil or Robitussin. And that is the entire point—cannabis is simply a performance tool.

In 2026, it’s crazy to me that no one in the industry has leaned hard into this category. Very few even talk about it.

Perhaps that will be you. Ping me, I might be able to help.

Onward,

SUNDAY SESH

This SESH will be data-focused and concise. I’ll only paste the DASHBOARD panels that materially changed, with brief commentary on what it might mean. Goal: DASHBOARD v2.0 adds analytical context, not more noise.

If you’ve been watching the periphery, the cannabis event firehose has been on full blast since we launched v1.0 on May 24th. And it’s not just cannabis. Across the many transformations we track, there’s a ton going on right now.

In cannabis specifically, we saw catalysts across every major vector: regulatory, legal, financial, operational, cultural. Even hemp made noise. More importantly, six (6) companies in the past 2 weeks dropped public breadcrumbs around future uplisting: Curaleaf, Verano, Vireo, Trulieve, GTI and TerrAscend.

It’s wild how few investors believed them.

If you were in our chat, you saw SUNDAY SESH did. Or at minimum, we didn’t dismiss them. That also reiterated my strong views from The Dales Report on May 19th, just a short time ago.

Of course, this all crystallized Friday when Trulieve confirmed it will officially uplist to the NYSE on June 10th.

It’s only fitting that Trulieve goes first. Kim deserved it.

So let’s roll up and dive into DASHBOARD v2.0 with a few quick takeaways:

1/BIFURCATION

• MSOS hasn’t attracted meaningful net capital over the past two weeks, yet NAV moved materially higher (~+23%). Very minor repositioning. See below for the fund-flow summary.

• Bifurcation is real and accelerating. Direct access to single names via Robinhood, plus the (potential?) loosening of custodial pipes, are potential factors leading more investors to pick specific names instead of relying on the ETF wrapper. That’s a good thing. It’s also a sign of maturity.

• I’ve been consistent on my view: the next wave of capital will be stock-specific and solutions-oriented. Trulieve this week was an example of both: a company with a clear idiosyncratic catalyst, reinforced by the Harvest “ring-fence” carve-off, which brought in ~$15MM of solutions-oriented capital for the non-medical assets to preserve the cleaner uplisting story.

Read more

SUNDAY SESH started as a selfish endeavor. It was a way for me to get my swirling thoughts down on paper across many topics that matter. To solve problems. To poke and prod my convictions.

With time, the SESH evolved into a content flywheel that helps me pressure-test and track the narrative in real time. A breadcrumb on X often evolves into a chapter in my quarterly “WHAT’S ON MY MIND.” Many chapters then become dedicated SUNDAY SESH deep dives that I further unravel on social and unpack on podcasts. And since narratives now move faster than ever, I do my best to update you in real time through our group chat as I closely WATCH THE PERIPHERY to help inform my views and capital. DASHBOARD makes the flywheel spin faster.

Although I spend most of my time dissecting cannabis, I do so in the context of a bigger obsession: deeply understanding transformational change as it unfolds at an accelerating rate.

Specific to cannabis, I feel strongly there are limited resources you can rely on. No hate—there are a few great platforms and people I trust. But there aren’t many that attack cannabis as it relates to the broader consumer, and even fewer that analyze cannabis in relation to our unlimited opportunity set as investors and operators.

As I always say: value isn’t free. Neither is your attention. Given that, I have an obligation to publish work worth consuming to help guide our collective decisions. Or you simply won’t stay.

I take that responsibility very seriously, and I’m constantly thinking of ways to provide unique value. Of course, I will never “spam” you, but you should have noticed increased frequency across the flywheel—including Substack—to cohesively tie together the narrative.

Which brings us to today’s launch: custom dashboards built from the ground up using public data to help evaluate the cannabis sector in real time. To compare and contrast. And to sharpen our “utility” curve. As we all know, the constant fight for our time and capital is very real. I won’t always be right, but I sleep better knowing what I own. And what I could own.

For the launch, I’m going to tell you what these objective metrics mean to me today. Every panel in the rolling dashboard tells a clear story to support my thesis. I’m confident you will learn something regardless of where you sit. If you want to see the data more clearly, use your desktop.

So roll up a faaat J, and let’s dive into the new SUNDAY SESH: DASHBOARD. It’ll live on the homepage, and my goal is to keep updating it over time.

And stay tuned for more…

1/RETURNS

WHAT IS IT: Here we track MTD, YTD, and 52-Week returns for U.S. cannabis operators we follow closely. We also show you how Big Cannabis is tracking relative to “Big Everything”: Food/Beverages, Alcohol, and Tobacco on an equal market-cap basis. We often toggle in Communication Services (i.e. Media, Entertainment) and Consumer Discretionary (i.e. Retail, Restaurants, Hotels, Apparel) to track other transformations that matter.

SO WHAT: This is a critical component for understanding how capital is flowing within cannabis; and how cannabis is performing relative to other consumer subsectors. This dashboard also helps track and measure several SUNDAY SESH convictions, both at the company-specific level (i.e. GLASF, GTBIF) and also at a thematic level.

Within cannabis, months will continue to be noisy (see Dashboard 2) but overall the horses are running, especially on a risk-adjusted basis (i.e. safety vs. spiff vs. stupidity).

At a subsector level, it’s very clear long Big Tobacco and Cannabis are significantly outperforming over the past year. Big Tobacco at +10% MTD stands out…I’m still very bullish on select companies in this space, especially relative to Big Everything.

2/WHERE THE $ MOVED

WHAT IS IT: This dashboard “follows the money” by specifically tracking MSOS and how its capital moved month-to-date. It shows NAV movements through a proxy for redemptions/infusions, and how these managers reshuffled the portfolio intra-month by security.

SO WHAT: The vast majority of capital inside cannabis is still moving through this ETF (for now). And we get a real lens into how these active managers think about portfolio construction. Given its size and importance, MSOS’ “beta” is felt at all times. Yes, they leave a strong wake. And yes, that wake often creates opportunity. Few thoughts:

Read more

As I’ve highlighted in my rolling “WATCH THE PERIPHERY” series, The Dales Report is part of that “must-see” cohort that I regularly consume. Shadd and Anthony are great hosts—they are well connected and informed, have actual convictions, and consistently host experienced operators in the trenches to help create a rich mosaic. This is critical to navigate the daily gyrations as the long-term narrative evolves.

During our discussion, we touched on many SUNDAY SESH themes:

• Cannabis 3.0: Where the future of cannabis becomes increasingly dependent on architecture as stages stack. While Cannabis 2.0 was about bifurcation and survival, this stage will likely be defined by unique company-specific strategies.

• Cannabis vs. Big Everything: Comparing cannabis to other consumer subsectors that I’ve deeply invested and operated in over my career. I talk about how cannabis harnesses secular tailwinds unlike much of the ecosystem—food, staples, alcohol, apparel, retail, restaurants, supermarkets, media—where most are pissing against the wind. Pricing unwinds yet COGS + labor inflation. K-shapes and demand destruction. Analog vs. digital platforms. Health/wellness and GLP-1s. Just to name a few. Remember: Big Ideas Take Time.

• GTI / RYM: Where I explain again why hemp may have started the RYM story, but the resulting architecture has far less to do with it today than most investors appreciate. And that’s the genius of the structure. RYM is effectively a synthetic convert—where the “bond floor” is supported by the now fixed royalty, and the convexity leans on expanding brands and distribution. Think about a potential $20BN hemp beverage TAM alongside ~1MM+ points of distribution versus ~13K regulated dispensaries today. When, not if.

Hopefully the first of many. Enjoy our conversation.

Onward,

SUNDAY SESH

Subscribe now

***Disclaimer: Not financial or investment advice, do your own work; this is intended for sophisticated investors. No conflicts, no MNPI, these are my own opinions, and no representation that what’s presented is accurate. As disclosed, authors of SUNDAY SESH hold common shares and derivatives of companies mentioned and they have no obligation to update or disclose changes. No representation is made as to accuracy or completeness. Past performance is not indicative of future results. And as always, cannabis was used frequently in the authorship to creatively solve problems. Know what you own.

Let’s be honest: reunions are strange. Time feels different. You’re suddenly back in the fishbowl with friends you may not have seen in 10 or 20 years. It’s like peering into a mirror and a window at the exact same time.

The mirror forces introspection—to see your life through the classmates who knew you before much of your story was written. Who you were then. What you thought mattered. And what actually happened.

At the same time, the window offers perspective—to see the arc of friends’ lives in a way no CV ever captures. The real version shaped by timing, judgment, luck, relationships, and reinvention. And most importantly, how they handled it.

For the first time in a while, time froze. I wasn’t obsessing over what comes next. Perhaps because I was surrounded by friends asking themselves the same question. Nor was I ruminating on what came first. Perhaps because these were friends who already knew.

As part of the reunion, I was asked what advice I’d give my classmates. It’s a humbling question given the audience—and one that took a few quiet nights to answer.

So for the younger crowd staring out the window—or frankly, the older subs looking into the mirror—here are three critical lessons I’ve learned along the way. I hope you find them valuable.

Welcome to SUNDAY SESH.

1/GET CLEAR

When we’re just starting out, we often reach for the path directly in front of us. We listen to friends and parents. We search for prestige and titles. We follow momentum.

I’m no different. Coming out of undergrad—nearly 6 years before grad school—I literally fell into banking with no fucking clue what bankers actually did. Ironically, those early—and painful—years provided clarity. I quickly knew I wanted to sit on the other side of the banker’s table—either taking risk or taking the reins of these businesses seeking counsel. That led me to principal investing—something I also knew very little about growing up—until I realized investing alone wasn’t the full expression of what I wanted to do.

The truth: I didn’t have a vision for my future.

For me, business school wasn’t about pivoting careers as much as stepping off the NYC-centric finance treadmill. It forced me to look around. Learn new tools. And most importantly, surround myself with talented people searching just like me. Being in the epicenter of innovation helped immensely. I absorbed the early waves of transformational change we now take for granted. And what it would take for these builders to bring those visions to life.

Twenty years later, much of what I’ve invested in—and still invest in and write about today—was catalyzed during those indelible years.

At some point, you have to stop optimizing for what looks good and start focusing on what actually lights you up. Not because every day is supposed to feel magical—that’s a ridiculous expectation—but because this game is simply too hard otherwise. You’re not going to survive the constant uncertainty, doubt, long hours, setbacks, assholes, and competition unless some part of you genuinely loves the game you’re playing.

Two decades later, my classmates who seemed most fulfilled weren’t necessarily the people with the cleanest résumés or the highest paychecks. More often, they found alignment between what energized them, what they were good at, and what the world valued.

My advice: get clear on where you want to go as early as possible. Because if you don’t, life has a funny way of creating a path for you.

You simply can’t hit what you can’t see.

2/ADAPT OR DIE

While I firmly believe you should get clear on your vision, you must not get attached to your story.

Your vision and your story are two completely different things. Your vision captures what gives you energy, aligns with your values, and reflects who you want to become. Your story is simply the current expression of that vision.

Like any great saga, it has to evolve. Hold on too tightly to an old chapter, and you risk turning your identity into a stagnating trap.

Let me give you a personal example: About 10 years ago I realized my story was attached to a dying business model. I saw clearly where the hedge fund industry was headed—toward siloed pods with very tight constraints—and I started questioning my role despite the decades of hard-earned reps.

Could I have succeeded? I’d like to think so. But rather than find out, I realized what was required to win conflicted with my vision. And I knew I had to make a change.

Twenty years ago, some classmates were absolutely convinced they knew what their life would look like. But what struck me most at the reunion wasn’t who “succeeded”—it was how many classmates ended up somewhere entirely different than they originally imagined. Of course luck and tragedy play a huge part, but many ultimately found paths better aligned with who they became.

Today, the world is changing faster than ever. AI is rewiring workflows and careers in real time. Business models and industries are being disrupted overnight. One day you may wake up and realize your current chapter is over. Sometimes by choice. More often by necessity. And when that happens, take stock of your vision, stay curious and willing to learn, and accept that L’s are required for W’s.

Then start writing the next chapter before the old one writes it for you.

3/GET FIT

In a world moving this fast, taking control over what you actually can control is paramount. And my physical and mental health sit at the top of that list. I’ve been clear in the past: today’s pace of change will eat you alive if you’re not prioritizing both.

Unsurprisingly, my classmates who were in the best shape 20 years ago are still the ones in the best shape today. Typically retired college athletes or ex-military, they figured out early that fitness wasn’t about aesthetics.

It was about setting a standard.

Twenty years later, that standard has broadened. More classmates were prioritizing health beyond the gym. Meditation, yoga, recovery, therapy, religion, and overall wellness were recurring themes. And to my enthusiasm, I had multiple unsolicited conversations about plant medicine like cannabis and psychedelics.

How far we’ve come.

For me, I certainly was not in that “fit bucket” back in grad school. Hardly. Although I was a competitive D1 athlete, I simply lost my way after college. I ate “fine,” but I was incredibly atrophied—routinely skipping the gym for the bar. A casual run or quick rumble on the mat made that painfully obvious. Worse, the meditation and visualization habits from my competitive days were long gone too.

Back when I was competing, I was repeatedly coached: “as your body tires, so does your mind.” When you’re physically depleted, you make terrible decisions. In my sport, that was a recipe for disaster.

Somehow I ignored these lessons. And man, were those painful to relearn as I approached 30. Then, I had moved from the private markets side of my firm to our growing public markets team. On my first day, I quickly realized I was surrounded by three Ironmen, including my boss and the founder of the firm. Already in their 40s, they somehow never tired. Even after 12-hour days, they still hit the gym or biked home. Regularly.

My youth and adrenaline got me through the first year, but by Friday I was fucking gassed. My body simply couldn’t compete. Public investing demanded speed, rapid information processing, and the ability to stay calm as new data streamed in.

One of my stronger assets—my mind—became a huge liability.

I knew I had to make a change.

The best gift I ever gave myself was hiring a trainer on my 30th birthday. I’ve been working out religiously ever since. Nearly 20 years later, exercise has become oxygen. And the real benefits come from how I think—especially during times of pain and uncertainty. Over the past two decades, that standard has expanded: meditation, recovery, journaling, and other rituals now anchor my daily life.

My advice: it’s never too late to reclaim control. Get your ass and your mind fit.

You will never regret it.

4/FIN

Time compresses for all of us eventually. The years start moving faster. Responsibilities pile up. And chapters must close whether we’re ready or not.

Which is why—for me—what actually matters is simple: get clear, stay adaptable, and protect your body and mind. Those assets compound too.

Maybe that’s why reunions exist: a mirror to reflect on who you’ve become, and a window into who you still might be.

Keep going.

Onward,

SUNDAY SESH

***Disclaimer: Not financial or investment advice, do your own work; this is intended for sophisticated investors. No conflicts, no MNPI, these are my own opinions, and no representation that what’s presented is accurate. As disclosed, authors of SUNDAY SESH hold common shares and derivatives of companies mentioned and they have no obligation to update or disclose changes. No representation is made as to accuracy or completeness. Past performance is not indicative of future results. And as always, cannabis was used frequently in the authorship to creatively solve problems. Know what you own.

If you’re here, chances are your career—and your constantly evolving role—is always fighting for more attention. And if you’re an investor or operator in cannabis, chances are since November it’s been a never-ending sprint crowding out everything else. When you layer on the other critical transformations moving at light speed, the sprint starts to feel permanent.

So far in 2026, I’ve never worked harder—and many people I admire seem to feel the same. I’m swimming in information, choices, tools, itches to scratch, people to call, capital to move, and a family to love than ever before. While these new AI tools have given me an absolutely insane productivity boost, they’ve created this twisted flywheel—one that constantly reminds me I might not be working hard enough.

By now, you know that I’ve spent my entire career investing and operating in change. Not incremental change, but the kind of change that breaks shit. Sometimes that’s from the “outside in” as an active investor. Other times it’s from the “inside out” as an operator.

Same arena, different seat. Through all of it, there’s one constant: change or die.

Given that, this quarterly “WHAT’S ON MY MIND” (“WOMM”) will focus heavily on weed and other transformations demanding my attention. More importantly, what I’m doing to harness and monetize them in this profound era of change.

So roll up a fat J—maybe reach for creative focus—and let’s dive into the 11th edition. Take your time—click backlinks to go deeper and track the evolving narrative. And of course, see my positioning.

Like every WOMM, this one will eventually be free after paying subs have time to digest.

Welcome to SUNDAY SESH.

Subscribe now

1/SAFETY, SPIFFS & STUPIDITY: UPDATED

Let’s set the tone with a market check and a refresh of my Safety, Spiffs & Stupidity (“SSS”) framework. From there, I’ll bounce between cannabis and other consumer transformations to show how I’m actively using it.

If you’re new to SSS, start here. At its core, I’m constructing a “synthetic convert”: safety generates durable yield, spiffs provide cheap convexity, and stupidity creates dislocations to pounce on. SSS was built for this era.

Remember: SSS is dynamic. As the world rapidly transforms, your portfolio should too—which is only possible if you’re not trapped inside archaic institutions that “debate” alpha while someone faster devours it.

Recall, the framework applies both within sectors and across asset classes. I skew heavily towards consumer, along with other sectors and situations where I have edge. This allows me to “stay in the trade” as the macro winds constantly shift, which is more likely as time compresses. Filling the “stupidity” bucket with idiosyncratic shorts—especially as beta keeps making new highs—is a cleaner way to manage risk.

That’s been my approach all year.

I’ve been transparent about my positioning—especially on the Cannabis Investing Network podcast and of course on X.

If you want to go deeper, reach out. This is increasingly the work I’m doing with institutional investors: sourcing, evaluating, structuring, and risk-managing investments focused on transformative change impacting the consumer.

2/CANNABIS MOVES

Let’s get to the meat of why many of you are here—how I’m positioned in public cannabis.

As you know, my cannabis exposure ramped significantly throughout Q1 and early April. This all occurred prior to Trump’s decision to reschedule cannabis to Schedule III on April 23rd. Since that event, on the margin I’ve added risk despite the ~40% move. This was a major catalyst that I still think is under-appreciated. I continue getting bigger in my horses rather than diversifying into more names.

• GTI: I’ve been buying GTI and RYM all year—see my posts on GTI (Part III) and RYM (Part IV). Even with this 45% rip, at ~$8/share I’m still only paying <6x GTI Core. And at ~$30/share for RYM, I’m only paying <$500MM for RYM that now gets $70MM/yr of fixed royalties. I’m effectively getting paid to own the hemp option (Senorita). Too cheap for the best operator with the best balance sheet.

• GLASF: I also increased my exposure in GH all year long. I’ve spent considerably more time with the business and management, including a trip to the retrofitted farm. I have conviction this team has more shots on goal than most. Now it’s about execution. While optically expensive at ~25x FY’26E EBITDA, Glass House’s earnings power in Cannabis 3.0 will open many eyes. Spiffier, yet safer than cannabis beta.

• TRULIEVE: It’s been a core name in the past so it’s always on my radar. If we learned anything since Trump got back in the saddle, don’t fight Trump or the companies in his ear. Recall, Trulieve navigated its debt cliff in late Q4/early Q1, still has ~$300MM of cash, and now has a bit more clarity on its $630MM UTP (which is 40% of its market cap). Still cheap. I’ve re-entered, but it’s not core.

• VERANO: The one “spiff” I entered AFTER the Schedule III news. I originally passed—and alerted you in the chat—but seeing it retrace was just too enticing. Not big enough to matter, perhaps some day.

• OTHER SPIFFS: I exited SNDL and a few other “hanging chads” post–Schedule III for small gains. They’re distractions—too illiquid and inferior to other opportunities. That said, they are all on my very short list if we do see another wobble.

• SHORTS: See the chat, but I’ve decided to increase short exposure to manage my growing long exposure. Unlike my longs, I’ve decided to broaden out the short bets across Tier 1s, Tier 2s, Canadian LPs and ancillary bets. Nothing personal, just trying to neuter exposure and focus on shorts where I diverge from the Street.

Before moving on, I have to get something off my chest: yes, better growth is preferred, but it’s not required with upcoming regulatory and institutional unlocks. Just look around the broader consumer ecosystem.

Campbell’s Soup (CPB)—trades at a 50%+ premium to cannabis, yet is secularly challenged with persistent revenue declines, has 4x leverage that’s increasing, and pays a precarious dividend that should get cut. There are hundreds of consumer companies that look similar or worse.

Don’t make this harder than it needs to be—cannabis is cheap, asymmetric, under-owned, beating Big Everything, and doing it with both hands tied behind their back.

Let’s see what happens when the handcuffs come off.

A lot more on cannabis below...keep reading.

3/SNAKE SHEDDING: SCARCITY WINS

I’ve said it before: now is by far the best investing environment for nimble investors with limited constraints.

To be clear, I have high conviction that the winners driving this market will grow exponentially—and will constantly shock investors because humans can’t think non-linearly. Inevitably, there will be wobbles along the way as the old regime pounds their chest. Or as bottlenecks temporarily delay the inevitable.

At the same time, I have the same conviction that the companies that fail to embrace change will be stuck in the mud—and constantly plummet because those same investors double-down on linearity and try to catch falling knives (read: software).

That combination creates a tricky setup as new eats the old. I call it: SNAKE SHEDDING. The old skin doesn’t disappear all at once. It tears, catches, and creates dislocations.

Many of the themes we’ve kicked around—especially in my WATCH THE PERIPHERY posts and X teases—are great examples of how this is playing out.

AI eating software. Hard assets eating soft. Distribution eating content. Data centers eating commercial R/E. Bitcoin eating fiat. Cannabis eating booze.

Scarcity eating abundance.

4/BETA STILL SCARES THE FUCK OUT OF ME

Like I keep saying: beta still scares the fuck out of me. So my focus is cobbling together a collection of idiosyncratic, non-correlated assets that are: secularly-advantaged, scarce, cheap, asymmetric, and durable where they can win with or without beta participating.

Cannabis is a clear example. And as we just saw, it doesn’t need beta’s permission.

Given that approach, I simply don’t have high conviction on where the overall market goes over the next 1–3 years. Yet it’s undeniable that after Iran stabilized, a capital “release valve” unlocked at precisely the same time S&P earnings estimates moved higher despite rising inflation. Not a coincidence.

And I know it’s hard to believe, but the U.S. is on the cusp of a manufacturing and industrial boom. Close investor friends thought I was insane last year to project a manufacturing PMI > 60 in FY’26. Just watch. At the same time, every American regardless of wealth is pissing against the wind as everything inflates.

That won’t mean the market goes straight up as the snake sheds. This volatility regime is likely here to stay—which should increase the frequency of “fear spikes” as liquidity disappears at exactly the wrong time. Higher volatility, more expensive funding, covariance blowups, and tight drawdown rules force institutions to all turn the dial at the same time. And when those same institutions come back into the pool, they search for what will not underperform.

During these moments, I actively turn the book while harvesting shorts. For example, during the Iran situation I closed many software shorts as I scaled and/or entered new longs (i.e. DELL, XOM, BAT, CRWV, SNAP are a few I’ve cited on X). I’m always doing work on situations I don’t own to prepare for these gyrations.

5/IT’S TERMINAL, BRO

The critical issue facing all investors is that terminal values for every business are being deeply questioned. And so as time compresses, what was safe in the past might now be risky (i.e. software, staples, media). And what seemed risky then, might now be safe (i.e. semiconductors, metals, biotech).

Scarcity vs. abundance theme, in bright lights.

6/ACTIONS > WORDS: SUMMARY

To quickly summarize, here’s how I’m actively deploying capital:

• I’m still running the “horses” with a heavy “safety-rich” allocation that gets deployed—and harvested—in waves to pounce on anomalies. I’m trading more than prior years. Why? More focus + more vol + more dislocations.

• I completely ignore short vs. long-term taxes—just a cost of doing business. Don’t overstay your welcome based on an arbitrary calendar flip.

• I’m building a collection of non-correlated, idiosyncratic assets that harness specific company or industry transformations—sized based on risk and event path within the SSS framework.

• I’ve dramatically increased my Bitcoin exposure again in Q1. Yes, I buy it every day, but I also added size in the $60-70K range when software was imploding. I continue to believe BTC will attract incremental capital as it further breaks away from code.

• Beta scares me more than ever. On one side, it’s dominated by concentrated positions in the hyperscalers/MAG7 that will be funding the boom (and funding HF longs). On the other, beta is filled with sleeping large-cap giants too slow to maneuver (see below: Disney). Still short much of the MAG7 (ex-GOOG and AMZN), QQQ/software, and XLP—I don’t want this risk.

• For the first time in years, some shorts are as big if not bigger than some core longs. Nike, Big Media, Big Food, and Big Alcohol were past examples of what I gravitate toward. I’ve been clear I’m short WBD and EA—highly asymmetric as risk-arb desks effectively sell puts.

• Finally, I’m always looking for investments that hedge or at times lever personal exposures. XOM “safely” hedged oil. UNH hedged healthcare inflation. Bitcoin hedges hard-earned fiat. The fundamental thesis has to work first, but solving real-world exposures adds utility.

7/“YOU DOWN WITH UTP?”

Back to cannabis.

The news that should have gotten your attention was the AG encouraging the IRS to consider retroactive 280E relief. This was the biggest new signal. I’ve been clear that I found it very surprising that few (if any) investors priced in possible UTP reversals. Put this on the heaping pile of mispriced convexity.

Let’s go back to understand why this is important:

• First, long-time followers will remember me banging the drum that all operators should turn off 280E to maximize optionality, where the penalty was lower than the cost of equity. And we saw that in droves.

• Because of that decision, UTP balances ballooned (except for GTI). This dynamic created another narrative headwind as we entered the feared debt cliff in FY’25. Many bears used UTP to justify their tired opinions that these companies would hit the debt wall. Wrong, as I expected.

So why do possible UTP reversals matter? Take Verano, with a $378MM UTP as of Q4’25. As of today, Verano’s market cap is ~$400-450MM. Read that again…its entire market cap is effectively the value of a “liability” that might disappear.

So are you down with UTP? Yeah, you know me.

Powder keg.

8/TIME TO DANCE: PART II

You might recall that in this phase of cannabis where stages stack, we’d see more consolidation. And we have.

Now let’s consider the prior UTP section. One of the biggest barriers to dealmaking has been a very wide “bid-ask” spread. On one hand, buyers remained disciplined given depressed multiples or stretched balance sheets. On the other, sellers were trying desperately not to sell at the bottom as the wall quickly approached.

With UTP, we now have a real source of strategic and financial value. Since UTP will likely take some time to resolve, the seller can use that newly-found “asset” to bridge the divide with a buyer who can take on that risk (but at a reasonable discount).

The beauty of this structure? The buyer can manufacture built-in accretion, and the seller can manufacture a headline price. Using the Verano example….we’re talking about ~80%+ equity upside for both parties to negotiate from. Win-win.

Think of it like a CVR—or a contingent-value right—which we typically see in biotech. Interesting angle to watch.

9/EARNINGS SEASON

I don’t expect major earnings fireworks—especially with a few pre-announces—and I don’t think expectations matter much for now. But management clarity, confidence, and transparency most certainly will.

While we are far from regulatory certainty and can’t count our chickens, recent events should start to shape the future narrative for each company. The start of Cannabis 3.0 should have catalyzed strategies unique to each company’s situation.

I’m going to tread carefully into Q1 prints if names continue to run into earnings. Take GTI. I simply don’t know if investors—and certainly the algos with stale targets—have fully priced in the $70MM royalty to RYM. That’s a material hit to EBITDA, offset by a meaningful tax shield juicing FCF (regardless of 280E). Similarly, I doubt investors understand this value will simply accrue to RYM.

So if we get another wobble, I’d be happy to buy again. Just lower.

10/PRICING

You might remember from Higher Exchanges that I have a variant view on how 280E taxes will filter through the value chain. Most believe the tax break will reduce end-consumer prices to be more competitive with the illicit market. True at the margin, but I believe timing and sequencing matter. Operators aren’t sitting around the table saying: “We just saved $X million in taxes, let’s give it all back to our customer!” Especially when you consider much of the value chain is choking on unpaid taxes and under-investment in its people and operations.

So what do I think happens?

• Credit Leads Equity: The first windfall goes to creditors. Companies delever, struggling companies pay down A/R, and possibly earmark funds for the IRS as the cost of debt capital declines.

• Internal Investment: Most teams are sitting on high-ROI projects that couldn’t be funded. That includes human capital. These get addressed next.

• Wholesale Pricing: Future pricing depends heavily on future regulation. Does hemp exist? Will Trump greenlight international and/or interstate commerce? The answers are critical. I believe prices will continue to normalize and the total profit pool gets redistributed.

• Consumer Pricing: Like wholesale, end-pricing will also normalize as states mature, but bifurcation should widen within and across form-factors. Meaning, the premium markup within categories will increase; and I expect certain categories to be more stable (i.e. concentrates vs. flower). Yes, brands will eventually matter.

11/THC BEVS: IF IT’S COLD, IT’S SOLD

Most THC drink TAM analyses are wrong regardless of the source. Why? First, it’s a data problem—national aggregators like Nielsen intentionally exclude THC, lumping weed bevs with “non-alcoholic” beverages that muddy the water. Second, it’s a distribution problem—many beverages are hitting stores and homes via non-measured channels like “alternative” distributors and DTC. Third, TAM estimates are anchored to past dispensary share. This is especially true with MSO execs who couldn’t effectively merchandise these differentiated products.

I estimate the market is pacing $2-3BN+ right now—easily. And the math becomes clear after my time kicking tires across national and regional operators and triangulating: door expansion, market share, sell-through, out-of-stocks, and end-customer mix shifts.

“Low-dose” mandates will ironically be another growth driver. As “sessionable” cohorts reach for more per sitting, the TAM will increase, benefiting everyone in the value chain. Producers (scale), brands (ubiquity), distributors (scale), on-premise (more pours), and regulators (safer roads) all win. Yes, even customers—you all get too stoned lol.

Yes, I’m optimistic the November hemp deadline will carve out THC beverages.

It just comes down to: Demand Leads Policy. Keep the faith—one way or another THC beverages are here to stay.

12/BEVERAGES: $20BN TAM MATH

So here’s how I triangulate the future TAM:

• Alcohol in the U.S. is a ~$275BN+ retail market—beer (~$120BN), wine (~$80BN), and spirits (~$75BN).

• Roughly ~60% of U.S. adults consume alcohol. Average adult per-capita spend is ~$900/yr, with drinkers spending well in excess of $1,500/yr. (Anyone drinking in a metro city knows these numbers are laughably low).

• Now focus on the cohort that matters: ~100MM Americans aged 18–40 where behavior is already shifting. CivicScience’s 2026 tracker shows 41% of U.S. adults 21+ use cannabis at least occasionally, with daily usage around 16%. More importantly, THC beverage behavior has doubled from 6% in 2025 to 12% in 2026. This is the opportunity: THC beverages “speak” to booze drinkers more than legacy THC users comfortable with existing options.

• It’s unlikely we’ll hit alcohol’s ~60% penetration or $1,500/pp spend soon, but if THC beverages reach even ~20%, we’re talking ~20MM consumers. Even at ~50% of alcohol’s spend, you’re already looking at a $10–15BN market.

• THC beverages already exceed 15-20% of alcohol retailer mix in some geos. Take Minnesota—where tax receipts imply a ~$100MM+ beverage market in a state with only 6MM people. Extrapolate that to larger non-rec states like Texas, Florida, and North Carolina, and $500MM–$1BN per state today is within reach.

So when people call this a $1BN category, I just don’t see it. We’re staring at a $20BN market hiding in plain sight.

13/MARGINAL UTILITY: DISNEY

Let’s switch gears.

Own consumer companies where the marginal utility of consumption isn’t negative. Could be a cup of coffee, an eighth of weed, a Netflix subscription, or the shirt on your back—different categories, same truth. Winning companies deliver more value as usage increases.

So, be skeptical of “one-off” consumer brands and experiences, or face unattractive costs to acquire and retain customers. There’s just too much “content” to be reliant on occasional or fleeting demand.

Disney is a good example. I’ve been quite bearish for 4+ years, where DIS is -45% vs. +70% for S&P 500. In 2026, I’ve made it a core short once again.

My simple thesis: Disney has good brands, but content is not king—and every part of DIS is under significant pressure. Streaming needs more spend to compete as linear TV (ABC) falls off; Disney’s ESPN affiliate fees are melting as it leans into DTC, and Parks—which represent 60% of earnings—are reliant on a weakening consumer. That’s where the risk is hiding— inflation (gas, food, insurance) and job stagnation have gotten worse.

Disney looks like a rudderless ship that now trades at a significant premium to its struggling peers—media, travel, software, and even theme parks and experiences. The setup looks more like Starbucks or Nike than the market wants to admit.

Iger left a soiled diaper for his long-overdue successor who now needs to clean up the mess.

14/ZIG-ZAG

I’d like to put a bit more meat on the bone around my career transition after a great ~5 year run.

As I’ve explained, joining TPB and leading their cannabis efforts was highly intentional, armed with a specific bet during that phase of cannabis: own the “picks and shovels” in an industry that should see significant store growth as normalization and the “green wave” swept through.

While I was armed with a rare and sizeable war-chest, I was one of the very few cannabis investors who left it largely untouched for M&A. When you are a strategic investor with unlimited duration, the unwritten rules matter. I did not “spray and pray” capital by design.

Despite sourcing 500+ deals over my tenure, the remaining investment process—evaluating, structuring, integrating, and managing—often revealed several vulnerabilities that made it hard to transact.

In the meantime, it provided an iconic platform to lean into what we already owned by expanding distribution, enter new markets and partnerships, and create new products. All the while, allowing me to help advocate for and legitimize our industry. To partner with incredible people shaping it. To study the entire value chain and build relationships across the world. To learn what works and what doesn’t. From public to private; startups to established MSOs; cannabis to hemp; growing to retailing and everything in between.

Simply, Zig-Zag provided a graduate degree in the weed business.

Nearly five years later, I’m ready to put that degree to a different use.

15/OWN TO OPERATE VS. OPERATE TO OWN

I’m often asked the difference between investing full-time and being a full-time operator.

With investing, you have to think like an operator, but can’t overlook that the game you play is against other investors.

With operating, you have to think like an investor, but can’t overlook that the game you play is against your competition.

Same framing, very different challenges to optimize capital allocation.

So it shouldn’t shock you to hear that the best investors and operators I’ve worked with are experts in both. Or have the self-awareness to know they need to be surrounded by them.

16/MAVERICKS: PART II

As time compresses, uncertainty increases—regardless of the ship or its captain. That’s why I strongly believe it’s more important than ever to underwrite CEOs who can best navigate change.

Bet on winners. I’ll take a great CEO over a great stock any day of the week.

They tend to be intelligent, experienced, hungry, kind, transparent, nimble, bold, and visionary. And highly aligned with investors. No “ick” factor.

How do you know? Evaluate track records. Interview past/current employees. Scrutinize past decisions and their current playbook. Deeply understand whether incentives will drive the right behavior.

And above all else, spend time with them if you can. See how they treat others.

If you’re actively allocating capital, this is the minimum standard that allows me to sleep well knowing another storm is always just on the horizon.

17/WEED ADVICE

Any SUNDAY SESH wouldn’t be complete without a little cannabis recommendation. But instead of a strain or a brand, this one’s about temperature.

Temperature is the most underrated factor in the level of buzz. Keep it simple: the hotter the combustion/vape/dab, the more potency. Want to chill but not blast off? Vaporize vs. combust your flower; set your dab rig at the lowest setting (<400; 2.4v), and even play with cooling off the smoke by adding ice to your bubbler or bong. I’d also experiment with the thickness of your joint: thinner joints = less surface area = less oxygen = less heat.

Yes, I take this shit seriously.

18/DO YOU REALLY MEAN IT?

Yes, every single word on this page originated at some point with cannabis riding shotgun. Maybe not the finished product, but most of the “essence” started as a note jotted down in the quiet of the night. (Folks, get a journal.)

At 48, I’m pretty self-aware about what helps me perform. And what doesn’t.

Today, cannabis’ purpose for me is to slow down time. To savor. To feel. To breathe. To think. To solve. And to be present.

Cannabis is a performance tool.

19/END

Transformation is never clean. It’s always violent underneath. But through it all, change separates those who thrive from those who are just trying to survive.

Since I got involved as a full-time cannabis operator, over ~12K dispensaries, ~50K head and smoke shops, and ~20K+ c-stores, liquor stores, bars and restaurants now offer THC products.

That’s a 10–15x channel expansion in less than 5 years if you’re keeping score.

As I navigate my next chapter, I take solace in that truth. I don’t know yet where my path leads. But I’ve never been more energized to find out.

It is Day 1 in Cannabis 3.0. Thank you for joining me on this journey.

Onward,

SUNDAY SESH

***Disclaimer: Not financial or investment advice, do your own work; this is intended for sophisticated investors. No conflicts, no MNPI, these are my own opinions, and no representation that what’s presented is accurate. As disclosed, authors of SUNDAY SESH hold common shares and derivatives of companies mentioned and they have no obligation to update or disclose changes. No representation is made as to accuracy or completeness. Past performance is not indicative of future results. And as always, cannabis was used frequently in the authorship to creatively solve problems. Know what you own.

Rather than spend valuable time writing about “what-ifs,” I’m using the time to dig deeper and understand the future path alongside trusted experts on the ground. Plus, there’s plenty of trusted commentary out there—here, here, here are my current favorites. I also think it’s worth noting that the operators that seem to have a better understanding of the event path were in the room the entire time. That signal shouldn’t be underestimated.

The one thing my audience should take away: Cannabis 3.0 is in motion. Business got a shot in the arm. Institutions will now begin to enter the space. Customers got closer to the plant. And the industry—along with its key players—will evolve. With a go-forward tax reset plus possible 280E clawbacks, the cost of capital will decline. As I repeatedly say, credit leads equity. This is all part of the thesis as stages stack.

That’s the win, and there’s no going backwards.

If you’re investing: stay the course, continue to back your horses, and hang the f*ck on. I did make some adjustments this week. But at a high level, I continue to think cannabis is a unique asset class that’s highly consistent with how I see our transforming world: a collection of esoteric, secular, scarce, cheap, asymmetric, durable, and non-correlated bets. On its own, cannabis can serve as a unique asset allocation in a world where beta scares the fuck out of me. And where great teams on the ground can create a lot of value.

So with that said, a quick few programming notes to assist you:

First, of course continue to monitor my X feed for my real-time perspective. Any questions on those, ping me.

Second, as I mentioned this morning, I’ll be active in our private group chat. As always, it’s the spot to catch my rolling commentary between SUNDAY SESHES that I don’t want to air on X. Feel free to throw in your questions—I read every one—as the chat always sparks interesting debates. This is for paid subs only to respect their time and capital commitment. Thank you for your support.

Third, the next SUNDAY SESH will be my quarterly “WHAT’S ON MY MIND”—this will be my 11th edition, focused on the transformational themes that define SUNDAY SESH. Of course there will be plenty of cannabis commentary. Expect that soon.

Fourth, I’m planning more content, not less for SUNDAY SESH. In the near term, I’m producing a future SUNDAY SESH: LIVE. My goal is to make these events focused and genuinely additive — not just another livestream. Stay tuned for that.

Lastly, if you’re an institutional investor or a consumer operator looking at the space, feel free to ping me directly. This is the kind of work I do privately: helping teams source, evaluate, structure, and risk-manage complex public and private investments, partnerships, and strategic opportunities focused on transformative change.

Onward,

SUNDAY SESH

***Disclaimer: Not financial advice, do your own work, no conflicts, my own opinions, cannabis used frequently in the authorship to face the pain and creatively solve problems. And, know what you own.

As you know, I do my best to publish pieces that are timely and top of mind—and capture the spirit of transformative change on topics that matter. Like the words on the page, I also create original art for each SUNDAY SESH. Every creation is intentional and designed to match the feeling and the critical themes running through each SESH—in my style and voice.

The digital art is also a real-time look at me learning new AI tools on the fly. All of the art for SUNDAY SESH—so far—has been generated or assisted by artificial intelligence across multiple platforms. I also utilize on-premise software to modify and enhance the images by hand. Most start as sketches in my journal, others start as ideas dumped as prompts.

Would I prefer to engage a real artist? Of course. That’s how I was taught—by one of the best. But the world is moving too fast right now. And this is a great way for me to play with these game-changing tools and feel the pulse of progress for myself. Perhaps it’ll push you to do the same. As mentioned, get to the other side.

Below is a running gallery of the original art behind each SUNDAY SESH, from the most recent to the earliest.

So in upcoming SUNDAY SESH posts, spend some time with the image. And if you want to design one for an upcoming SESH, please reach out via chat.

So let’s pack the glass and take a quick look at the rolling art narrative, which I’ll update over time.

Welcome to SUNDAY SESH.

Subscribe now

All artwork is created for and used by SUNDAY SESH, a publication of Vindico Capital LLC. Please do not use without permission. Translation: don’t be the guy.

MAY ‘26: WHAT MATTERS MOST

“THE FARM”

MAY ‘26: WHAT’S ON MY MIND: VOL XI

“SNAKE SHEDDING”

APRIL ‘26: STEP FUNCTION

“CANNABIS 3.0”

FROM HERE DOWN IS THE ART TIED TO THE ORIGINAL APRIL 2026 POST

APRIL ‘26: ART FORM

“HAPPY ACCIDENTS”

APRIL ‘26: WE TRUSTED THE WRONG SYSTEM

“SYSTEMS OF THE BODY”

APRIL ‘26: RYTHM OF A NEW WORLD

“ROCKET COASTER”

MAR ‘26: WATCH THE PERIPHERY: VOL III

“BRAIN DUMP”

MAR ‘26: TIME COMPRESSION

“CONVEXITY”

MAR ‘26: THUMB IN THE EYE

“GREEN GIANT SMASHES BIG EVERYTHING”

FEB ‘26: WATCH THE PERIPHERY: VOL II

“POD”

FEB ‘26: SOFTWARE SLOP

“KABOOM”

FEB ‘26: WATCH THE PERIPHERY

“SLIVER”

JAN ‘26: THE PAGE NEVER TURNED

“MIND THE GAP”

DEC ‘25: TURN THE PAGE

“EVOLUTION”

DEC ‘25: GET TO THE OTHER SIDE

“FEED THE BRAIN”

NOV ‘25: BREAKING THE RYTHM

“OH SHIT”

OCT ‘25: WHAT’S ON MY MIND Q3/Q4 ‘25

“BRAIN WON’T SHUT OFF”

OCT ‘25: WHAT I LEARNED THE HARD WAY

“CANNABIS IS A PERFORMANCE TOOL”

SEPT ‘25: DEMAND ALWAYS LEADS POLICY

“FIAT IS TORCHED”

AUG ‘25: THE RYTHM IS GOING TO MOVE YOU

“STRAP IN”

AUG ‘25: CONTENT IS NOT KING

“CONTENT = DISTRIBUTION”

JULY ‘25: ALL AT ONCE

“WEED IN MOTION”

MAY ‘25: WHAT’S ON MY MIND: PART IX

“BANANA BUDTENDER”

APR ‘25: WHAT’S ON MY MIND: PART VI

“PROFESSOR BANANA”

APR ‘25: WHAT’S ON MY MIND: PART VI

“IN BANANAS WE TRUST”

JAN ‘25: WHAT’S ON MY MIND: PART V

“THE BANANA REPUBLIC”

OCT ’24: WHAT’S ON MY MIND: PART IV

“I VOTE GREEN”

MAR ’24: WHAT’S ON MY MIND: PART II

“BIFURCATION”

FEB ’24: WHAT’S ON MY MIND: PART I

“BRAIN DUMPED ON PAPER”

NOV’22: WHAT I’M TELLING MY PORTFOLIO COMPANIES

“WARNING SIGN”

***Disclaimer: Not financial advice, do your own work, no conflicts, my own opinions, cannabis used frequently in the authorship to face the pain and creatively solve problems. And, know what you own.

What began as a rogue plant ended up unlocking an unknown biological system already inside us. Unlike most drug discoveries built to address a specific indication, humans stumbled on the cannabis plant over 10,000 years ago with little understanding of why it worked the entire time.

The first major scientific breakthrough came in 1963. Raphael Mechoulam and Yechiel Gaoni isolated CBD and then THC, cannabis’ primary psychoactive compound. Those breakthroughs mattered because it turned cannabis from a mystery into chemistry. And once they did, scientists found something much more profound.

In 1988, researchers then identified a cannabinoid receptor in rat brain tissue—what we now call CB1. That was the unlock. Because once scientists established that the brain had a receptor specifically responsive to cannabinoids, the obvious question became: why would the body have a receptor for a plant compound at all?

The answer came in 1992, when Mechoulam’s group identified anandamide, the first endogenous cannabinoid—a naturally occurring compound produced by the body that binds to cannabinoid receptors. They named it after the Sanskrit word ananda, meaning bliss.

In other words, the body was already making its own cannabis-like messengers.

Researchers then identified a second cannabinoid receptor—CB2—and in 1995 Mechoulam’s team identified 2-AG, a second major endocannabinoid that would prove even more abundant than anandamide.

By the mid-1990s, the full outline of the endocannabinoid system (“ECS”) was emerging just as the culture was beginning to rethink—or rediscover—cannabis.

To me, this is not a coincidence.

On one hand, we learned our body was biologically wired for cannabinoids. On the other, culture was beginning to figure out in real-time that the government’s 80+ years of propaganda may have been a lie all along. Throw in targeted racism and xenophobia, and it becomes obvious why the fight we see today was inevitable.

So let’s break out the dab rig and get into the ECS—because once you understand the system, the old and tired labels start to fall apart.

Welcome to SUNDAY SESH. This SESH is on me.

Subscribe now

ECS: WHAT IS IT?

Picking back up from above, a few brave pioneers pushed forward and proved the ECS is not fringe science. It is a complex cell-signaling network involved in maintaining homeostasis—or balance—throughout the body. As mentioned, your body already produces these cannabinoid-like compounds—such as anandamide and 2-AG. These compounds are released, bind to receptors, and are then broken down by enzymes. The system is constantly working to maintain equilibrium. CB1 is concentrated heavily in the central nervous system and brain, while CB2 is associated with peripheral tissues and immune cells. That is why the ECS shows up in conversations ranging from cognition, appetite, pain, inflammation, mood, pleasure, and broader systemic regulation.

Similar to these natural compounds found in our body, the natural cannabis we consume is biologically wired to work with the same embedded ECS. Whether you’re a person of faith or science, it’s worth emphasizing that our bodies were “engineered” to oddly work with a random plant that naturally grows across the globe.

The point is: your body already makes “keys” for these receptor “locks.” Cannabis—like the endogenous cannabinoids inside your body—simply open the same locks.

Unlike the other 11 major systems in our body—like the circulatory, nervous, digestive, and endocrine systems—almost no one is taught about the ECS in medical school. And yes, even today, that includes many of the world’s best medical institutions training tomorrow’s best doctors.

Think about that for a second—the best doctors in the world never learn about one of the body’s major systems discovered over 30 years ago. That’s like training a heart doctor, but skipping over the sections on cholesterol and statins.

ECS: WHY IT MATTERS

Once you understand that your body already “speaks” cannabinoids, the lazy framing around cannabis starts to collapse. This is not some random outside substance smashing into the body from left field. This is a plant whose active compounds interact with a pre-existing biological system that exists for a reason.

That does not mean cannabis is harmless, perfect, or universally good. Of course not.

It means the plant is working through a physiological architecture already central to human regulation. From my seat, that is one of the most underappreciated truths in the entire category. Is it medicine? Is it wellness? Is it supplementation?

One thing is clear—cannabis isn’t the devil’s lettuce.

When you accept that the human body has an endocannabinoid system whose central role is to help regulate balance, a lot of the old propaganda starts to look even more ridiculous than it already did.

SUBSTITUTION

What makes this even more interesting is how cannabis differs from alcohol at a biological level. Alcohol does not interact with a dedicated, body-wide regulatory system the way cannabinoids do. Instead, it works more bluntly—through complex interactions with multiple neurotransmitter systems, including GABA and glutamate, effectively slowing and dysregulating neural signaling across the brain. That is why alcohol lowers inhibition and impairs coordination, memory, and judgment in a relatively non-specific way. It is broad neural disruption, not targeted modulation through a homeostatic signaling network.

Given this dynamic, it’s no surprise that alcohol can have many painful side effects. Why? Because our body wasn’t built for throwing back rounds of booze. One night of heavy drinking makes that point all too familiar.

Cannabis, by contrast, is interacting with a signaling system the body already uses. To be clear, that does not mean cannabis is “harmless” nor does it say that every use case is smart or benign, especially for youth or at-risk consumers.

But it does make it fundamentally different nevertheless. Alcohol works more like broad neural override. Cannabis modulates a system that already exists. From a consumer and category standpoint, that distinction matters more than most people realize.

This also helps explain why cannabis shows up across so many different consumer use cases. People do not just use it for one thing. They use it for sleep, stress, appetite, pain, inflammation, recovery, mood shifting, social lubrication, focus modulation, and general recalibration. That diversity of use has always confused outsiders who want cannabis to fit into one neat box: a dangerous drug with no health benefits.

WHAT’S IN IT FOR US?

This is also where smart operators and investors need to think harder. Because if cannabis is interacting with a body-wide balancing system, then product architecture matters enormously. Indication matters. Dose and onset matter. Form factors and quality matter. And in the end state, consumer education and trust will greatly matter.

The difference between a low-dose, fast-onset beverage or gummy, a combustible joint, and a high-potency concentrate is not just branding. It is user experience mapped onto physiology. That is why I continue to believe the category gets more interesting—not less—as it becomes more precise and more CPG-like where THC and other cannabinoids become ingredients. The result of that will be an explosion of use cases that we are barely scratching the surface on today.

And as these get figured out, new multi-billion dollar TAMs will be created instantly.

Let me give you two personal examples.

While I still maintain a prescription for Ambien, I’ve mostly swapped it out for cannabis more than a decade ago for numerous reasons. Similarly, when I’m home sick with a nasty flu or cold, I reach for a super high-quality RSO or rosin gummy or 6-star dab instead of dosing with Nyquil. It’s not even a debate anymore. These two categories alone exceed $65 BN in TAMs—and while I’ve known about these alternatives “forever” even a guy like me simply didn’t have access to them (especially RSO). Now I do. And so do hundreds of millions of people around the globe.

It also signals why the future of cannabis will not be won by the loudest people yelling “legalize it” as if the work stops there. Legalization is just the first unlock. The bigger opportunity is building products, brands, channels, and experiences that respect how people actually use cannabinoids in the context of real life. Sleep is different from social. Recovery is different from recreation. Calm is different from euphoria. Daily low-dose is different from weekend overconsumption.

A category built on top of the ECS should ultimately become more segmented, more targeted, and more intelligent over time. That is what mature consumer categories do when they stop being defined by stigma and start being defined by users.

The future is here.

CONCLUSION

For decades, cannabis was framed by the government as a devil frying our brains, making us crazy, and even stealing our women. Ironically, that erroneous view held by prohibitionists helped fund and prove their own lunacy. Clearly, the science then and now points to a very different reality.

As an activist in the space, I—like others—tend to take this truth for granted. When you step outside the “cannabis bubble” it’s very clear the mainstream conversation on cannabis is still centered on validating—or rejecting—80+ year old lies.

But that is on the verge of dramatically changing. With continued regulatory progress, practitioners will begin to study the plant without reputational and career risk. And my view is that future unlocks will be staggering. My strong thesis is that this work will validate decades of “bro science” I’ve personally experienced now over 30 years. I’m personally most optimistic about cannabis’ impact on inflammation (see above regarding colds/flu).

Because once consumers understand that cannabis is not merely about intoxication—but about interaction with a real endogenous balancing system—the category opens up in a very different way. It stops looking like a binary debate between “drug” and “medicine” and starts looking like what it actually is: a broad consumer and wellness category with deep biological roots, wide use-case potential, and a regulatory framework that still badly lags reality.

Which is why I keep coming back to the same idea in different form: we trusted the wrong system.

And your body already knew that. The world is just starting to catch up.

Onward,

SUNDAY SESH

***Disclaimer: Not financial or investment advice, do your own work; this is intended for sophisticated investors. No conflicts, no MNPI, these are my own opinions, and no representation that what’s presented is accurate. As disclosed, authors of SUNDAY SESH hold common shares and derivatives of companies mentioned and they have no obligation to update or disclose changes. No representation is made as to accuracy or completeness. Past performance is not indicative of future results. And as always, cannabis was used frequently in the authorship to creatively solve problems. Know what you own.

If you haven’t digested Parts I, II, and III, I strongly suggest you start there to complement what I’ve publicly said on X. Or perhaps, have your favorite LLM read them alongside you. Go ahead…we’ll wait.

Part IV was mostly polished for a few weeks now, but I decided to focus on more timely market-specific topics you all seem to crave. I hope those detours provided real value.

As you know by now, GTI shareholders by definition indirectly own a significant chunk of RYM. And given its materiality, if you’re not paying attention to RYM, you’re simply not paying attention to GTI.

In Part IV, I’ll reset the facts, walk through RYM’s Q4, refresh what the market is implying, and isolate the key changes—and risks—in the public filings. Of course, I’ll walk through this week’s (April 1st) amended royalty structure and why it matters as the narrative migrates to Cannabis 3.0.

Punchline: this week’s news is a major needle mover, and it only increases my conviction in the original GTI/RYM thesis. As a reminder, paying subs get access to me in real-time on the SESH group chat—where I shared my thoughts on the RYM news well before the market opened. RYM ripped ~60% in a day on its highest trading volume since December. I think that move was justified—in fact, I think it deserves to go much higher.

So with that, let’s crack a bevie, and dive deep on recent updates in GTI’s BrandCo—RYM.

Welcome to SUNDAY SESH.

2/BRASS TAX: RYM Q4

Now that you’ve digested Parts I-III, you appreciate that RYM isn’t just some random hemp micro-cap orphan. Most importantly, it became GTI’s BrandCo vehicle: a “ring-fenced” entity that owns key GTI brands and clips valuable royalties on GTI’s regulated products. At the same time, RYM provides GTI strategic optionality across hemp-derived THC as the rules are rewritten while providing a valuable NASDAQ listing.

Subscribe now

Read more

As I discussed on the CIN pod, watching the periphery is just situational awareness: closely watching the edges to help inform decisions at the center. And with time compressing, this skill has become a necessity.

I’ve practiced this skill my entire life—whether I realized it or not. Probably born from extreme curiousity as a kid, and beat into my brain by gifted mentors and teachers. Similarly, change was something I found painful, but a constant of my life. Over time, I luckily realized something better was always on the other side of pain—just as many of my heroes said.

I’m sure many of you know exactly what I mean.

The least I can do is pass that along by showing you what it means to me in practice. To be clear, my periphery might not be yours. But nevetheless, you must figure out what’s worth paying attention to. And like everything else, this skill compounds—meaning, what you noticed this week will help inform what you’ve already observed.

So with that, let’s roll up a fat J, and digest what grabbed my attention. Some below are “must-see” weekly content for me, and as always I’ve tried to add context as to why it matters.

Welcome to SUNDAY SESH. This SESH is on me, enjoy.

1/POMP PODCAST

I’ve always loved watching Anthony during the early crypto days, mainly because he took an incredible amount of shit with incredible poise on national TV. It felt like 99% of mainstream investors thought he was absolutely crazy or stupid. Or both.

Since then, he’s matured, broadened his reach, and started bringing on some of the most engaging investors, operators, and thought-leaders well beyond his crypto lane. He’s getting the last laugh, and I’m here for it.

The pod today is a melting pot of fresh ideas to make a soup filled with incredible “lateral thinking” insights. Which again, you’ll only pick up on if you’re watching the periphery (ok, that’s the last one today, promise).

In this episode with , the discussion is wide-ranging but grounded on markets with deep historical context given the recent explosion in energy and commodities. Perfect analysis for today’s “euphoric vs. paranoid” capital markets.

All year long I’ve been banging the drum that there’s a time to make money, and a time not to lose money. On that, I’m very aligned with Jordi—as I have for the past 2+ years. Jordi paints a real framework for why capital allocators should pay attention.

My view: Keep your powder dry. But if you see opportunity and have edge, lean in.

2/DELL: Play Nice But Win: A CEO’s Journey from Founder to Leader

You might have seen a few tweets from me on Dell lately. I can’t stress this enough—read real books. In a world built to increasingly hijack our attention, I think we need dedicated outlets to focus uninterrupted and train our brain. And find joy. Personally, I’ve always loved reading non-fiction memoirs. You can absorb someone’s hard-earned life in a few days that often comes with enormous gratitude, humility, and universal lessons. Every one I’ve read is underlined, along with hand-written notes on the flap I can revisit. And this ritual creates an internal energy that’s hard to describe. These books always inspire me. It’s truly electric.

I bring up this book now for two very important reasons.

• First, this isn’t exactly new content—it came out in 2021 and was collecting dust in my cue. Call it luck, but I picked it up around the time he was standing up Invest America as he ran a $115 BN company about to enter a supersonic tsunami. Hearing Michael describe then what was on the come just 4 years later was incredibly valuable perspective.

• Second, Michael paints a picture of how Dell specifically fits into the transformational change we’re living through right now. At times, the book reads like an IPO prospectus without Michael realizing it. And because it’s his memoir, it comes across as objective, candid, emotional, and filled with conviction—at exactly the moment the Street may have been doubting him (yet again).

When you combine those two observations, it became an opportunity to dig back into. Thankfully I did.

Read books folks. Here are few I absolutely loved in the past few years.

3/ALL-IN: FOUR CEOs ON THE FUTURE OF AI

Ok, I admit it: this podcast is a love-hate. Some of the time it feels like propaganda, and sometimes it feels like a bunch of highly successful domain experts wading into unfamilar topics. That said, they always come prepared, always give both sides, and bring on phenomenal CEOs. And unlike most podcasts, they at least give you a convicted view. Trust me—that’s really hard to do publicly week in and week out.

This episode from NVIDIA’s analyst day is a gem. I want you to focus on Coreweave’s CEO Michael Intrator downplay the major FUD bear case led by folks like Michael Burry and Jim Chanos that tech—and neoclouds like CRWV—are over-earning because they are under-depreciating their GPUs coupled with the fear of an AI bubble.

“My take on the GPU depreciation debate is that it’s nonsense.”
— Michael Intrator, CEO Coreweave (CRWV)

I prefer to give CEOs with great track-records the benefit of the doubt until proven otherwise. In this particular situation, I recognized a unique pattern I lived through. Back in 2011-2012, I had many heated debates on hard-disk drives (HDD) as the bears were screaming: “These HDD companies are highly cyclical, capex-heavy with declining demand, especially when Apple is producing laptops with next-gen SSD.” (If that’s too technical, drop that sentence into your LLM for a quick overview.)

Similar to today, it’s important to note this HDD bear case was right before Facebook’s IPO (May 2012), Instagram was barely 2 years old, the iPhone was <5 years old (4S), and Netflix was still shipping physical DVDs right before streaming. Point is: data and content production were about to explode.

In addition to failing to recognize this future digital transformation, the bears lost track of the transformational consolidation that had occurred that smoothed the “boom-bust” cycle. And that consolidation made the industry vulnerable to a tragic Japanese tsunami creating massive shortages. Lastly, they failed to recognize these names were dirt cheap, even before this exogenous shock.

Sound familiar?

This is basically today’s memory situation, which Manish cogently outlined on our podcast.

In hindsight—I was watching the periphery. And they weren’t. And many of those same highly controversial views from that era are still paying me today.

So, when I hear comments like this from Coreweave’s CEO—and read his body language—at a minimum it forces me to remain objective and try understand the truth before I get swayed by the bears.

4/HARVARD MEDICAL //
“THYMUS MAY BE CRITICAL FOR LONGEVITY”

Let’s change gears, shall we. I’ve previously mentioned tools that might help to get to the other side, and I made it clear that LONGEVITY is a critical theme I’m leaning into both in my personal life and my portfolio. This topic has always been on my radar.

This HBM article is eye-opening for a number of reasons. For one, these team of Harvard Medical doctors leveraged AI to analyze 27,000 routine CT scans within hours. On average, it takes ~20 minutes for a human to study just one scan. Working that thru, this would have taken 5 years if done by humans. 5 years!

Let that sink in. What was done in 5 years is now being done in hours.

When says that math and science are “cooked”—this is proof.

The practical takeaway is to own your health—been saying this forever. And with AI and new tools, you truly can while avoiding a 3 month waiting list and $2K doctor bill.

Yes, there’s a cannabis angle here too: if immune resilience is upstream of healthspan, then how you use cannabis greatly matters. Remember, cannabis is a performance tool. More on this in future SESHES.

5/CONCLUSION

Hope you enjoyed this SESH diving deeper on the process of being hyper aware of the massive change all around us. And how I find and filter endless content to reveal valuable signal.

It truly is the most exciting time of my career, even if it’s also the most uncertain time of my life.

I’m sure you can all agree.

Onward,

SUNDAY SESH

TIP YOUR BUDTENDER

***Disclaimer: Not financial or investment advice, do your own work; this is intended for sophisticated investors. No conflicts, no MNPI, these are my own opinions, and no representation that what’s presented is accurate. As disclosed, authors of SUNDAY SESH hold common shares and derivatives of companies mentioned and they have no obligation to update or disclose changes. No representation is made as to accuracy or completeness. Past performance is not indicative of future results. And as always, cannabis was used frequently in the authorship to creatively solve problems. Know what you own.

“You can’t understand cannabis unless you understand the consumer. And you can’t understand the consumer unless you’re closely watching the periphery.”

This week I was back on the Cannabis Investing Network podcast to talk through my latest views—inside and outside cannabis.

Manish and I can literally talk for hours. Good and bad news here—we did. That’s why I’ve put together show notes organized by key themes. The goal of this SUNDAY SESH is simple: highlight key takeaways, positions, and a few “easter eggs” that YOU might find valuable and can put into use. I also outline what active investors and operators should be doing to “get to the other side” and stay ahead.

I’d still encourage listening to the entire pod (even at 1.5x)—or download the script and have your AI agent do it for you. I don’t do these very often, and it gave me a chance to connect several critical dots I’ve discussed. This SESH is backlink-heavy—that’s our MO and each link is highly intentional—especially for newer subs that just joined the party.

For subs, this is the distilled version ordered by what I think you care about:

• Why cannabis remains significantly misunderstood, as I materially increase exposure (in only 2 names);

• How I’m thinking about recent market volatility; and

• Where I see opportunity leveraging my Safety, Spiffs & Stupidity framework.

So roll a big fat doink, let’s get cerebral, and recap the CIN podcast.

Welcome to SUNDAY SESH.

2/CANNABIS: LOADED SPRING

“Cannabis is really interesting. Even though no one cares, but this is why it’s a potential risk dampener.”

Cannabis is a mirror image of what scares me most about today’s market. Unlike the “mechanical” and concentrated capital driving beta, cannabis is fragmented, under-owned, under-researched, and largely ignored. I’ve been clear how I’ve structured this transformation in the past—including shorting Big Alcohol (and by extension Big Food)—as the major thesis I underwrote over 5+ years ago has come to fruition. You know them well by now: bifurcation, the strong getting stronger, and balance sheet > income statement as cannabis stages begin to stack in the next phase. (If not, start here, but sort thru my top SESHES.)

Read more

I’m a 25+ year “hand’s on” consumer investor focused on transformative change—and now a full-time investor and operator in the cannabis sector.

I’ve led over $4BN of active investments across public and private companies throughout the capital structure—from consumer startups to legacy turnarounds—at the intersection of internal change influenced by rapid and relentless secular change.

I began my career at Soros Private Equity after banking, spent over a decade at Magnetar Capital joining near its inception to become a Senior Portfolio Manager, and later founded Vindico Capital, a concentrated “constructivist” fund focused on small-to-mid cap transformations.

Over the past 5 years, I’ve led a “cannabis-first” growth strategy from the ground up for a NYSE-listed company.

Whether an engaged investor—or an aligned Board Director and operator from within—the common thread has been partnering with management teams to navigate and execute change—with the humility, grit, and expertise required to empower C-suites and Boards to act.

When you focus on change for as long as I have, you get to invest across nearly every sector and cycle. With time, I’ve specialized in consumer: CPG, staples, cannabis, beverages, alcohol, tobacco, restaurants, retail, apparel, hospitality, entertainment, media, technology, and more. Why? Because I’m obsessed with “consumerism”—the transformational forces that drive what, how, and why we buy.

MOVE THE NEEDLE: BE A CHANGE AGENT

My #1 goal is to move the needle of culture.

My relationship with cannabis started over 30 years ago. My curiosity during high school led me to a NORML meeting on campus at Columbia University as a freshman. It was in 1996, right before Prop 215 was finally approved in CA. I learned more about the benefits of the plant and the grassroots effort to legalize it, and the rally sent me down the path as an economics major to deeply analyze the horrific social and economic impacts of prohibition.

I concluded then that the government’s view of cannabis—which has been used medically for over 10,000 years—was built on a mountain of lies, racism, and deception now spanning 80+ years. These barbaric laws destroyed millions of lives—mostly black and brown men and their communities—while incentivizing organized crime and violence in our streets. That simply didn’t sit right with me. I’ve been on a mission ever since to fight for change to give this plant and those harmed their fair chance at redemption.

I felt strongly then—which is less controversial now—that legalization would provide net benefits across the spectrum: from unwinding 50+ years of systemic racism and end the futile war on drugs; creating a new industry built on wellness growing millions of jobs and raising desperate funds for our government; and providing new standard of care solutions to many healthcare issues while curtailing today’s opioid crisis.

I became a champion of legalization behind the scenes and always “on the low” for fear of enforcement and reputational harm—of which I was exposed to many including from the NCAA, Wall Street, and of course the government. I began my cannabis journey first as a consumer and activist, then an advisor and investor, and now as an operator for one of the largest brands in the cannabis value chain.

CANNABIS IS A PERFORMANCE TOOL

I was never a “dead head” nor do I consider myself a “stoner”—but rather a high-performing (but definitely rebellious) kid that didn’t take the “traditional” path my CV claims. By 13, I was a 2nd Degree Blackbelt in Taekwondo. Next, a D1 All-Academic top-ranked golfer that happened to also be very good at school. I also had a social life, filled with misfits and “degenerates” like me. I had talent, but the secret was always curiosity, discipline and working my ass off no matter what I passionately pursued. Still do today.

To win on the field and in the classroom—especially with the insane amount of training, traveling and studying over dual seasons at an Ivy League institution—I simply couldn’t couldn’t afford to be hungover or strung out on pain meds.

In my late teens, 20’s, 30’s—and now late 40’s—I consistently found cannabis to be a valuable “tool” to help me perform. From avoiding addictive pain meds, to dealing with my Type-A anxiety and pressure, to optimizing my sleep, to unlocking self-compassion to help solve major life and work problems, and avoiding alcohol which for me was always a painful waste of time, money and calories. Decades later, I’ve replaced several “standard of care” solutions with cannabis as the industry matures.

Some of my fondest memories over the years—from concerts, to food, to travel, to dating, to simply hanging with friends—all involve cannabis. And some of my darkest moments over the years—from injuries, to slumps, to breakups, to deaths, to work stress, to depression, to pains of parenting—all involve cannabis to heal.

There when I needed it: with friends on occasion, or now more typically, alone in the quiet of the night. And never on the clock or when I needed to actually perform, luckily. A tool, never a crutch.

These days as a consumer, I’m on the hunt for some of the most exclusive and exotic batches grown by some of the best talent throughout the country. I’m in deep on cultivars and genetic integrity, keeping detailed notes to learn and capture the experience. It helps me to understand and compare world-class brands, strains and consumer trends, and catalog the effects to help me perform. As long as it’s clean and grown with unbridled passion, I’m chasing it. My weed fridge is never empty. I’m also very much in the weeds on scientific research to back up “bro science” that I’ve witnessed for myself and others for 30+ years.

MY DIFFERENTIATED CAREER PATH

After college I didn’t know what the fuck I was going to do, especially since I spent nearly 10+ years training every day often for 10+ hours a day. But I had a passion for science, business and investing at early age. Part growing up with an immediate family full of entrepreneurs, college-nevers, and hustlers; and part opening my first brokerage account when I was 12 with a deep passion for both Wall Street (1987) and GoodFellas (1990). My tolerance for risk taking and high pressure over long-periods of time, combined with self-belief and grit were my advantages early on.

Wall Street seemed like a good fit.

First as a banker at Merrill Lynch, I learned from my clients like KKR, Blackstone, and TPG on what made a good business and an attractive investment. I immediately wanted to be on their side of the table, and after a few years I joined Soros investing in buyouts and growth equity where I learned to do deals, take risk, and provide flexible capital to solve problems. Soros was and is an idol of mine so it was a dream.

After Stanford Business School, I joined Magnetar Capital—an “upstart” hedge fund that grew to $15BN in AUM where I helped build and scale several businesses as an eventual Senior Portfolio Manager. Public and private. Debt and equity. Long and short. Startups to distressed/turnarounds. All leveraging a deep fundamental toolbox to pursue (and compare) opportunities across the capital structure with a “hand’s on” constructivist approach to push for change when needed. I was an early adopter of the “friendly activist” approach and spun my strategy into Vindico Capital which I ran for 4 years (and still do, all family capital).

From the beginning I always told it to C-suites straight, but with humility and perspective to get them to act on their own with accountability. It’s still my approach to this day.

If there’s a common thread to my investing approach, I always focus on transformative change rooted in fundamentals. Typically, I harness monumental secular themes that cut across sectors—and then sort through the “winners and losers” to monetize a highly variant perspective. With decades of experience, I know it when I see it.

Cannabis is a great example of this—and why my worlds collided about 8 years ago when a few of my portfolio companies were starting to surface cannabinoids, and conservatives like John Boehner were starting to dive in. I took that as a major sign that this was a generational opportunity for folks like me to not only create great businesses, but for me personally, to really move the needle of culture.

While that was (and still is?) taboo inside Wall Street, this massive green wave has afforded me the opportunity to come clean, pay it forward, and move the needle.

We are just getting started.

Welcome to SUNDAY SESH.

In an industry where trust and consistency can be as scarce as the very flower it tries to grow, Todd has been an invaluable resource and partner. And to me personally, a reliable friend. What I value most is that he and his CB1 team are relentless: true warriors who show up to the arena every day, battle scars and all. I deeply respect that.

If you’re new here, I’ve spent the past 25+ years as an investor—and more recently an operator—focused on transformational change within consumer. I’ve invested throughout public and private markets, across the capital structure, and across the full company lifecycle—from private startups to public legacy turnarounds. And just about every “event” in between.

The past 5 years I’ve been leading a “cannabis-first” strategy from the ground up for a NYSE-listed company, leveraging a playbook I’ve developed for well over a decade. As I’ve repeatedly said: you can’t understand cannabis unless you understand the consumer. And you can’t understand the consumer unless you closely watch the periphery.

While I’ve been lucky to see and do a lot, the common thread over my career has been partnering with management teams to navigate and execute change—with the humility, grit and alignment required to empower C-suites and boards to act.

Long before Todd and I met, I was that guy at Thanksgiving—back in 1996—trying to convince my family that cannabis prohibition was misguided. I leaned on economic theory, but most of what I argued was simply common fucking sense. As a DI Academic All-Ivy in a sport that didn’t have an offseason, I noticed something pretty quickly: my test scores, my scorecards, and my overworked body improved when I swapped booze and pain meds for cannabis.

To me, cannabis was a performance tool. Thirty years later, it still is.

Staring at my glass of wine that night 30 years ago, I knew deep in my bones cannabis would eventually transform everything in its path.

As I often say: Big Ideas Take Time.

In addition to wearing multiple hats, I also write SUNDAY SESH to pressure-test my views as the world rapidly transforms, weaving in a differentiated cannabis perspective. It’s core mission is to educate and pay it forward—especially for our future leaders who have yet to find great mentors and institutions along the way. I was simply lucky.

So when Todd asked if SUNDAY SESH would be interested in joining his cannabis “Player’s Club”—I didn’t hesitate.

To kick this off, I wanted to bring back an older Sesh that still holds up—LET’S GET REAL—now with updated backlinks (our MO, learned from a true OG). It focuses on cannabis’ big idea that most simply miss: this industry will be massive. And although the rules are still murky, you’re kidding yourself if Big Everything isn’t paying attention. Don’t miss the forest for the trees.

So roll up a fat J, let’s get real, and dive into one of my foundational cannabis tenets.

Welcome to SUNDAY SESH.

LET’S GET REAL
Don’t Miss the Forest For the Trees

Originally Published: JUNE 2025
Backlinks Updated: MARCH 2026

Think of a world where there’s exploding demand for a “new” product. Demand that spans generations. Seniors, adults, young adults. Ubiquitous. Global.

For some, a rational and efficacious new standard of care.
For many, a reconnection to simpler times.
For most, a safer “better-for-you” alternative.

From the grandma who finally gets relief from her arthritic, creaky hand.

To the veteran battling nightmares or chronic pain—who turns to the plant instead of opioids that numb, addict and destroy.

To the intense, Type-A professional who drives extremely hard, but refuses sleep meds, painkillers, Xanax, or SSRIs (🙋‍♂️).

To the young parent who realizes the 3rd glass of wine makes them slower, fatter, and grumpier, especially the next morning.¹

To the athlete or meditating yogi who consumes—on occasion, and with intention—to test their endurance, strength, and focus while aiding recovery.

And to the Gen-Z who wants to “chill out” but still needs to be up at 6am to surf.

The point is: cannabis demand has been exploding—and the wave is still building. More consumers, more patients, more use cases, more frequency per existing consumer, and of course, more (relative) spend of wallet.

On one hand, this market wasn’t created out of thin air—it lived in the shadows for 80+ years. Today, it’s undoubtedly stealing significant share from existing markets, while inventing new ones that offer new standard of care solutions.

On substitution, we’re talking enormous markets. Just in the U.S., cannabis is “ankle-biting” the:

• $600+ Billion OTC/Pharma industry, including the $20BN opioid and $20 BN OTC/Rx sleep med markets. Worth pointing out that despite the decline in opioid usage, the cost per pill has increased 2x since 2015 (creating a powerful feedback loop, much like cigarettes);

• $250 BN Alcohol industry, of which 1/3rd is beer ($122BN) which is now showing the worst annual shipments in 25 years, and 1/3rd is wine which is now pacing the lowest global consumption in 64 years. Spirits? You’re next.

• Or maybe it’s the $110 BN Tobacco market, that isn’t as relatively exposed—in fact, it’s highly complimentary—but it’s an industry desperately trying to find growth with its old horse—cigarettes—now >75% off from the peak hit in 1965. Like entering the new $5-7BN white pouch segment, that ironically doesn’t contain any tobacco.

Whether it’s a dispensary, headshop, smoke shop, liquor store, bar, restaurant, convenient store, cash-and-carry, pharmacy, gas station, supermarket, or an airport duty-free—just to name a few—all of these stores and distribution pipes are watching with intense paranoia (“Wtf is happening?”) and euphoria (“Does this come in other flavors?”).

You really think these highly strategic, deeply established distribution networks—reaching over 1.2 million stores—aren’t paying attention?

Get real.

When you step back from all the noise, and all the drama: this is the foundational tenet for any cannabis investor and operator to understand:

In the end-state, this industry will be massive.

Don’t lose sight of the forest for the trees.

Onward,

SUNDAY SESH

¹ Also me, it’s been 5+ years since I’ve had more than 1-2 drinks per month. I used to love drinking wine and beer. I still do, but it does not love me back.

***Disclaimer: Not financial or investment advice, do your own work; this is intended for sophisticated investors. No conflicts, no MNPI, these are my own opinions, and no representation that what’s presented is accurate. As disclosed, authors of SUNDAY SESH hold common shares and derivatives of companies mentioned and they have no obligation to update or disclose changes. No representation is made as to accuracy or completeness. Past performance is not indicative of future results. And as always, cannabis was used frequently in the authorship to creatively solve problems. Know what you own.

At the depths of the Great Financial Crisis the VIX spiked into the high 80s. The market’s fear gauge was screaming for its mommy. On top of managing the portfolio, my team and I were modeling scenarios early Sunday mornings around which banks might not open the next day. Regularly.

It felt like the entire system was burning down.

I remember those feelings viscerally and can recreate them instantly—the good and the bad. All of it still sits just below the surface. In fact, I spend a lot of energy making sure my mind doesn’t go back there too often.

Weed helps.

Experiences like that leave a mark. They armor investors. They teach humility. And they recalibrate your sense of how markets behave when things break.

But what’s interesting is what happened next. From the end of the GFC through much of the following decade, volatility steadily declined. Central banks flooded the system with liquidity, interest rates collapsed, and risk premiums compressed across the entire capital structure. Looking back, markets entered one of the most stable financial regimes in modern history.

And for folks like me, we adapted but never forgot.

By 2017, the VIX briefly touched 10. Ten! The markets barely moved. Although the global economy was growing in unison, chaos was everywhere. Hurricanes and wildfires. North Korea firing missiles. The #MeToo movement reshaping culture. Trump nuking political norms. Yes, I keep receipts.

Looking back, that calm likely marked the beginning of a regime shift. Since then, while volatility is still relatively muted, we see these recurring sharp intermittent spikes reminding investors how fragile the system can be. Volmageddon in 2018. COVID in 2020—sending the VIX to 83, its 2nd highest reading. Then SVB in March 2023. The yen carry unwind in August 2024. And finally, the Tariff Tantrum last year. Today with the VIX hovering around 30, it seems we might be on the verge of another.

Different catalysts, same message: markets can flip on a dime. And in both directions.

Diving deeper, the more interesting observation isn’t the spikes themselves, but rather how the market processes these shocks faster than it used to. Look at the trajectory—and the severity—of major drawdowns since the DotCom bubble:

Dot-com dragged on for years. The GFC took more than a year to bottom. COVID fell ~35% in a month—then snapped back as liquidity arrived. Since then, panics hit hard but resolve relatively quickly usually in a matter of weeks or months.

That’s not just volatility.
That’s time compression.

I’ve been hammering this theme for months as our world rapidly transforms. Something bigger—something structural—is likely happening.

I’m going to dive into the weeds on why: i) Time Compression; ii) Mispriced Convexity; and iii) Mechanical Capital.

Themes I’ve uncovered before, but now through the lens of volatility. Once you start viewing markets through that lens, these moves we’ve seen over the past few years stop looking like anomalies. They start looking like features of a faster system.

So let’s roll a big boy joint and let’s get volatile. There’s enough to go around—this SESH is on me (read: FREE). If you’re new here, spend time with the backlinks—and if you can’t, have your agent do it.

Welcome to SUNDAY SESH.

Subscribe now

1/ AI IS COMPRESSING TIME

Historically, markets priced risk around predictable rhythms. Earnings cycles. Fed meetings. Quarterly guidance. Analyst revisions. Information moved in waves where investors had time to process and debate developments. Price discovery was messy, but it was gradual.

That cadence worked because the underlying pace of change was relatively slow, which aligned with the financial architecture built for a slower world. A world where “long duration” meant the future was far away and uncertainty could be discounted gradually.

For most of the past decade investors weren’t just buying earnings. They were buying time. Time before meaningful competition arrived. Time protected by scale, distribution, switching costs, and capital intensity. Think back to prior SESHES—like CONTENT IS NOT KING—to understand how time was a sharp weapon that’s now blunted.

In this old era, time was the moat. And if the Internet chipped away at that moat, AI simply obliterated it.

Why? Technology—specifically AI—compresses time. Today, a model release can reprice an entire sector in days as investors rethink the economics of incumbency. We saw this in software in Q1, and the shock spilled into insurance and logistics—anywhere automation or cost curves can shift quickly. Today the future arrives all at once.

When the replacement cost of competence collapses—when code can be generated instantly and iterated continuously—competitive cycles shrink. A product that once enjoyed years of defensibility may now face viable competition in months.

The point isn’t whether those moves were right or wrong. The point is how fast they happened.

Markets aren’t mispricing companies.
They’re mispricing speed.

And when speed becomes the dominant variable, volatility changes character. In this new compressed system, information flows instantly and capital reacts mechanically.

Price discovery no longer happens smoothly—it happens in bursts.

2/DURATION: CAP STRUCTURE TENSION

Once you start looking at markets through that lens, you begin to see interesting tensions emerge across the capital structure. Specifically, debt and equity need fundamentally different things to function properly.

As we say: debt is built on reality, equity is built on hope. I should know—I’ve been lucky to invest in both, and frequently at the same time.

Debt needs certainty. Predictable, stable cash flows. Healthy coverage ratios. LTV cushions. Whether you’re underwriting mortgages or software private credit, the premise is the same: you’re betting that the future will resemble the past.

Equity is different. Equity is priced off the riskiness of that credit, and by extension, what risk premium equity investors demand. The upside lives in uncertainty—the possibility that value can compound with unlimited return.

But AI complicates both sides of that equation.

If technological change accelerates dramatically, long-duration assumptions become harder to model. And if you can’t confidently model what a business looks like in the future, pricing the spread between debt and equity becomes unstable. Some argue it might even collapse on itself.

That’s why you get “freak-outs” across the capital structure. Sometimes it shows up in debt —like SVB, where duration risk suddenly mattered again. Or today’s private credit. And sometimes it shows up in equity—COVID, tariffs, the violent software repricing.

In both situations, a lack of capital structure fluency and the inability of pros to color outside the lines causes enormous confusion. But the underlying tension is the same.

The system is struggling to price duration.

3/MISPRICED CONVEXITY

Putting #1 and #2 together leads to another critical factor I talk about a lot: mispriced convexity.

Not textbook convexity. What I’m referring to is structural convexity—the kind created by incentives, positioning, and narrative risk.

In this context, convexity means securities behave like loaded springs. They can sit dormant for long periods of time, building tension beneath the surface, until something shifts and the price moves violently.

Professional investors aren’t paid to be early, and they certainly aren’t paid to be the last one out. So capital tends to cluster around consensus trades until suddenly it doesn’t. When positioning becomes crowded, markets become fragile. (See: BETA SCARES THE FUCK OUT OF ME.)

The result is what traders call “air pockets” where the leading narrative holds everything together until it cracks. And once it does, it simply snaps—often in both directions.

Convexity cuts both ways. While most investors focus on explosive moves higher, we’ve seen plenty on the downside as well. Banks during SVB, UnitedHealth last year, and software this year are a few that come to mind.

Violent moves. Sudden factor unwinds. Massive deleveraging on the way down, and almost chase-like behavior on the way up.

The magnitude of those moves isn’t new.
The speed is.

4/YOU ARE NOT HUMAN

Finally, there’s another layer to this thesis that investors often underestimate: the marginal investor today is increasingly non-human.

ETFs. Robo-advisors. Quants. Fixed-allocation strategies. Risk parity. Trend followers. Now add in AI, and the list goes on and on.

By some estimates, more than 80% of market activity is no longer human. Capital is deployed by systems designed to hug benchmarks, minimize tracking error, and avoid career risk. The result is forced concentration and crowd-like behavior that can appear stable for long periods of time—until it suddenly isn’t.

From experience, what I see is that machines, their mandates, and their mismatched capital now dominate the system. These “mechanical” investors don’t operate the way discretionary investors do. They may have conviction in their frameworks, but from a security-selection standpoint they don’t really care what’s inside the portfolio.

They care about the scaffolding, not the bricks.

Similarly, the remaining human pros amplify this system. These narrow sector pods operate with enormous leverage and are under constant pressure to stay fully invested. They don’t ask whether a sector is attractive—they simply are forced to allocate within it. (Insane if you ask me, which I repeat constantly to close friends who are some of the best pod PMs in the world.)

And because everyone operates similarly, their collective behavior is defined by triggers. Volatility thresholds. Drawdown limits. Momentum signals. Factor controls. Covariance matrixes.

When those triggers fire, the response is mechanical. Positions are cut. Leverage is reduced. Exposure is rebalanced. The dial is turned down.

And because so many of these strategies rely on similar signals, they tend to move at the same time.

The result: a system where repricing happens instantly. Can you feel it?

5/THE FUTURE PIVOT

With the VIX today around ~30, we’re probably nowhere close to peak fear. That said, we’re just about the area where the market starts looking for a pivot.

Historically, that pivot almost always comes in the form of more liquidity. Whether it’s bailing out the banks and credit during GFC and SVB, or bailing out the equity during COVID and the Tariff Tantrum—it always comes back to more liquidity in the system.

This time—however—it’s murky.

My base case is that the system resolves itself the same way it always has. Wars and geopolitical shocks are expensive. Worse, Middle America—the administration’s main audience—is about to get its balls squeezed in ways markets may not fully appreciate yet as oil screams higher.

And when the bill comes due, the easiest way for policymakers to stabilize the system is the same lever they’ve been pulling for the past fifteen years. PRINT MOAR FIAT.

My view is that the next round of liquidity simply might not look and feel the same way—whether it’s UBI, or cost curve controls, or AI bailouts. Which in my mind is a matter of when, not if.

6/LET’S BRING IT HOME

I certainly don’t know what tomorrow brings, but I’m highly confident in a few key themes that sit in the background as I deeply focus on specific-company transformations over a defined duration. Which in some cases, is forever.

So to wrap up this SESH, here my key take-aways:

1. Time is compressing, fueled by transformational AI;

2. Convexity is mispriced, exacerbated by capital structure convergence;

3. Market structure is increasingly non-human, forcing mechanical shifts; and finally

4. Liquidity always arrives, until it doesn’t.

Hard to tell where we end up. For you and me, just focus on buying right. And if you must hedge, hedge stupidity.

Onward,

SUNDAY SESH

I worked my way through inches of printed paper—yes, printed—highlighter in hand, two cups deep, flagging which analysts I needed to speak to before the bell.

It was ritual. And it was—by far—my least favorite part of my day. Peaceful sunrises over the Hudson River and later Lake Michigan frequently turned into violent storms.

Why? Because of the power those early morning notes carried.

In that old regime, sell-side wasn’t commentary. It was oxygen. If you were on the right side of the note, you felt false validation. Wrong side? You prepared for war.

For a Type-A investor whose team mantra was “no surprises,” nothing was more frustrating than getting surprised by the Street. My team and I knew the business and industry cold. We took pride in our relationships with management. We were not always right, but if it was in the book we had a variant view.

So on these mornings—like when a random analyst downgrade came out of nowhere—we braced for pain. That day and for weeks after, hundreds of millions—and often billions—of market value would move. Conviction was tested. Pretenders got swayed. And if your thesis hadn’t changed, you were forced to hold the line.

Like I said, my least favorite part of the job. War sucks.

Fast forward to 2026. If you’re still relying on public sell-side as your edge, you’re wasting your time. This isn’t about the quality of the work—much of it is still valuable. It’s about market structure, which I’ve deeply discussed in past Seshes.

Like today’s mainstream media that simply “summarizes” yesterday’s news, today’s sell-side is often “noise” highlighting yesterday’s “signal.”

If you’re reacting to the sell-side, you’re the liquidity.

Now here’s the twist. In cannabis, there are barely any sell-side analysts left. Limited morning notes. No consensus guardrails. So if you want conviction, you have to build it yourself. For most investors, that void is disqualifying. For us, it’s the juice.

If few are going to cover this space rigorously and consistently, then we have to. Which brings me to Part 3 of our rolling GTI / RYM narrative. This time, we focus on the big dog: GTBIF. In Part 4 (soon!), we’ll focus on its Brandco RYM—my favorite name to cover in the space and still missed by many (even if it’s more binary today as the intrinsic value skyrockets).

I’ve said before these SESHES are written for an audience of one: me. So I’m going to give you a lens into how I dissected both GTI’s quarter/year, the implications on GTI’s securities and by extension RYM, and what I think it means going forward.

If you’re investing in the space, this is worth the entry fee. Don’t feel the need to pay us—honestly—but if you’re simply relying on FinTwit rumors don’t expect good outcomes. Hard truth. Know what you own.

So roll up a fat J, let’s get weird and dive into the Thumb.

Read more

A few SESHES ago I unpacked what I mean by “WATCH THE PERIPHERY.” If you took anything from that post, it should be this: the signal starts at the edges. I’ll never go backwards, but now I’m widening the aperture.

In the past, a <insert sector> investor or operator only had to focus on the <insert sector>. For example, if you invested in insurance, you had to know the universe cold: what drivers matter, who’s beating, who’s inflecting, what consensus thinks, and where your edge lives. And if you were an insurance operator, you focused on underwriting discipline, capital strength, and protecting the combined ratio.

Stay in your lane. Execute. Repeat.

Don’t get me wrong—that work still matters. It’s just no longer enough. If you run that same playbook today with blinders on, you’re going to get decimated.

Do you get it now?

I promised more experimentation in 2026. This is part of that promise: showing you the inputs shaping my view of the world. With that framing, here’s WATCH THE PERIPHERY: VOLUME 2. In this piece, I’m sharing the podcasts I never miss. Don’t focus on timestamps. Focus on platforms. These are my weekly inputs. Yes, weekly. When information moves this fast, podcasts are one of the few places you still hear signal before it migrates to the center. I’m constantly refreshing the stack because fresh voices begin before they’re widely recognized.

This won’t be a weekly digest. You don’t need more homework. But in future volumes I’ll highlight the articles, podcasts, reports, and tweets that stopped me in my tracks. You decide what to do with it.

So with that, pack a fat bowl and let’s dive into it. SUNDAY SESH is in session.

1) HIGHER EXCHANGES PODCAST: TerrAscend at a Turning Point: Federal Reform, Capital Strategy & the Path Forward

I’m going to be honest—I do most of the heavy lifting in cannabis myself, talking to industry peers across the value chain regularly. That said, I rarely miss a Higher Exchanges podcast—especially when they bring on great guests who rarely speak. Sure, there are points of disagreement, but Jesse and Morgan provide another on-the-ground lens that complements what I’m seeing in real time. They consistently bring on guests who help pressure-test what’s actually happening beneath the headlines.

This episode features Jason Wild (Chairman) and Ziad Ghanem (CEO) from TerrAscend. While I don’t often talk about TerrAscend, Jason and Ziad are operators I know well and deeply respect. Jason embodies the investor-turned-operator. Ziad embodies the operator-turned-investor. In my judgment, they’re a formidable duo that clearly have their hand on the wheel on a bumpy road.

One core takeaway from this episode: Unlike many of TerrAscend’s peers, Jason doesn’t fear interstate commerce, which is inevitable as cannabis stages stack. It might be “5 to 10 years away,” to quote Jason, but investors NOW need to understand how their horses will run on this open field.

To be clear, there are multiple paths for existing bifurcated winners to thrive in an interstate world. The easy example is Glass House. The harder example is how MSOs like TerrAscend position for it. We’ll unpack this in 2026, but my view is that when “Big Everything” inevitably enters, they will need a dedicated clean, tested, proprietary source of biomass.

Most investors assume interstate commerce just means MSOs fighting each other on a bigger map. That’s thinking too small. A scaled cultivation network can become vertical integration infrastructure for a non-cannabis entrant that understands branding and distribution but not production. That’s how global tobacco works. Alcohol too. Cannabis will rhyme. And once again, that’s why the GrowCo vs. DistributionCo vs. BrandCo analogy was previously discussed.

2) MOONSHOTS PODCAST: Overcoming Job Loss, Purposelessness & the Coming AI Disruption

I’ve mentioned Moonshots before, as it’s one of my “go-to” podcasts I never miss. I met Peter Diamandis at Goldman Sachs’ Builders & Innovators conference in 2013, and since then he’s been an invaluable guide for thinking about transformational technology. He and his Moonshots co-hosts consistently highlight—in real time—where compounding breakthroughs are headed long before they become obvious, investable, or broadly understood.

I strongly suggest you put this podcast on your watchlist—it’s starting to move markets like we saw last week with the release of Opus 4.6. And from the conversations I have with C-suites, they largely ignore what’s coming. Hard truth.

This episode from January brings in Tony Robbins — another deeply influential figure in my life. Together, Tony and Peter unpack how AI won’t just disrupt jobs, but meaning itself, forcing a shift from survival-based work to purpose-driven contribution.

The core takeaway from this episode: in an AI-abundant world, the real edge won’t be intelligence or efficiency, but adaptability, creativity, and a clear sense of why you do what you do.

3) JORDI VISSER: The SaaS-Pocalypse, Bitcoin Crash and Why Understanding Palantir is Now Important for Both of Them

Another weekly must watch: ’s Sunday YouTube. I know talent when I see it, and Jordi is about to have a breakout moment. (Hard to believe he only joined X in March 2022 and still has fewer than 50K YouTube subscribers. Let’s revisit this in a year.) About a decade older than me, Jordi is one of the few who reinvented his Wall Street career by actually deploying transformational technology.

You don’t have to agree with everything he writes, but man, you are doing yourself a disservice if you’re not taking it all in. For the past 18 months, I’ve been on the same side of most of his themes. And it’s working.

The core takeaway from this episode: The AI bubble didn’t burst—it rotated. SaaS is experiencing a historic relative unwind as capital shifts toward hardware, infrastructure, and real-economy scarcity. Position accordingly.

4) INVEST LIKE THE BEST" PODCAST: Gavin Baker

This one is a double-header. First, I absolutely devour Patrick O’Shaughnessy’s "Invest Like the Best” podcast as he brings on exclusive long-form interviews with top-tier execs you simply can’t get anywhere else. In my judgement, he’s one of the best interviewers in the game. Second, this episode happens to bring on Gavin Baker. Gavin runs Atreides Management, and is one of the most thoughtful investors in semiconductors and AI economics. Having covered the computing stack for over two decades, Gavin’s truly an encyclopedia and an investor I closely watch.

The core takeaway from this episode: AI progress isn’t slowing. It’s compounding, and the constraint isn’t ideas, it’s compute, power, and economics. Scaling laws still work, post-training breakthroughs are extending the curve, and the real investment question isn’t “who has the best model,” it’s who controls the infrastructure, drives cost per token down, and captures value as intelligence becomes abundant and electricity becomes scarce.

5) THE POMP PODCAST: Jordi Visser

Anthony Pompliano is one of the most persistent evangelists of Bitcoin in institutional circles—not because he shouts the loudest, but because he’s spent the better part of a decade translating crypto from fringe ideology into capital allocation logic. I’ll be very honest—I don’t take everything Anthony says as gospel—especially his views on inflation where he continues to pound away at CPI (or Truflation) as the basis to lower rates. He’s not entirely wrong—yes rates are likely going lower—but I find his humility and ability to distill complex subjects into simple insights admirable. And while I don’t know him personally, my gut tells me we have a ton in common. Persistence. Discipline. Humility. Reinvention. Focus.

The core takeaway from this episode: Visser’s point is simple but profound: in a world where AI is commoditizing intelligence and eroding software moats, true scarcity becomes the only durable growth attribute— and Bitcoin is one of the very few large-scale asset classes that offer it. For now it trades tethered to the venture-SaaS complex because both are “built on code,” but once software beta exhausts itself and capital starts searching for growth without fragility, Bitcoin becomes the natural rotation target. I tweeted about this yesterday.

WATCH THE PERIPHERY isn’t about chasing noise—it’s about understanding where signal is born. Volume 2 is me showing you the inputs I regularly consume before ideas get sanitized by committees and re-packaged by the Street. By the time traditional research publishes the “story,” the edge is already priced. If you want to win in this environment, you cannot rely on legacy gatekeepers—you need true situational awareness.

Edge doesn’t start at the center. It always starts at the margins.

Onward,

SUNDAY SESH

I’ve been very clear in Sunday Sesh that I’ve been highly skeptical on software as these transformational forces move from the “periphery” to the main stage. On X, I left chunky breadcrumbs. For paying subs, I gave you the entire loaf. Some examples you hopefully digested:

• In late 2024/early 2025, I completely exited my largest position in Spotify. Despite a clear winner in an expanding digital music TAM, I saw exuberance and “nothing can go wrong” attitudes from the same skeptics that called me crazy for buying Spotify before it went vertical. Today, Spotify is 35% lower than my exit.

• By mid-2025, I made it clear I was tilting the book away from technology and software in favor of healthcare, and later PMI-sensitive sectors like energy and industrials. Since June, XLV (Healthcare) is up +21%, XLE (Energy) +25%, XLI (Industrials) +15%….and the IGV (Software) is now down roughly -25%.

• Then in Q3 2025—since Beta scares the shit out of me where software + communications comprise 40% of Beta—I shorted software and the MAG7 directly tied to this unfolding AI catalyst. Not because they aren’t great companies. They are. But because everyone thought they were great companies. Since November, the IGV is now down ~30% while the MAG7 is -9%.

As always, Zig when they Zag.

While I’ve spent decades investing in software—especially consumer software across the capital structure, both public and private—I’m humble enough to know definitively I simply can’t compete with a Citadel software PM playing their game. That just means I must play a very different game, one they structurally can’t express.

So what am I doing now? Am I picking up diamonds? Covering shorts? Are there cannabis software names caught in the downdraft that deserve a look?

So roll up a fat J—maybe reach for something cerebral—and let’s get into it. SUNDAY SESH is in session.

2/WHAT THE F*CK IS GOING ON

Software’s re-rating is highly symptomatic of other secular “oh shit” situations I’ve lived through firsthand. Big-box and physical retail vs. online and Amazon, fueled by software and related APIs. Physical newspapers and linear media vs. the digitalization of content, powered by edge devices (like Apple) and software-native platforms like Meta, X, TikTok and Snapchat. To me, what’s happening in software right now isn’t new. History doesn’t repeat, but it sure as hell rhymes.

So let me give you a no-bullshit situational awareness of what’s going on:

• Software didn’t sell off this week because demand collapsed. It sold off because certainty did. For over a decade, high-quality SaaS was treated like a bond: predictable, long-duration free cash flow streams that justified lofty multiples fueled by the narrative that “software will eat the world.” AI shook that thesis. Not by breaking the current model (yet?), but by injecting a fog of war into what those future cash flows look like. When investors can’t model duration, they reprice it hard. That’s why stocks got cut in half without earnings imploding. The implication isn’t “software is dead.” It’s that generic, seat-based SaaS just moved into the “too-hard” bucket. And the path to re-rating now runs through proof, not promises: accelerating core revenue, AI-driven expansion, and durable free cash flow in an AI-augmented world. Narrative alone doesn’t get you paid anymore. My variant view: those lofty 8-10x revenue multiples are likely never coming back.

• The more unsettling take goes further. AI doesn’t just compress multiples. It may suppress the total software spend itself. For decades, enterprises bought SaaS because building in-house was expensive, slow, and risky. AI flips that equation. When workflows can be created, modified, and orchestrated by agents at near-zero marginal cost, the market for buying software shrinks rather than rotates. Add in the speed mismatch, where AI iterates continuously while incumbents ship quarterly, and emerging compute constraints, and you get a regime shift. Value migrates away from bloated application layers and toward infrastructure, energy, hardware, and the small set of software platforms with real data moats, deep workflow lock-in, or unavoidable network effects. This isn’t a blanket call. It’s a redistribution of hundreds of billions in market cap. Selection, not sector exposure, is everything. My variant view: SaaS earnings won’t implode, but sales cycles will lengthen, pricing pressure will intensify, and every scratch in public markets will turn into a hemorrhage as nervous investors question everything.

There’s a ton of super intel out there—again, don’t wait for the slow-moving Street. Your job, as always, is to curate it. Here are two must-watch conversations this week that best informs how I’m thinking about software .—Jordi Visser (as always), and Brad Gerstner on All-In podcast.

3/WHAT AM I DOING

What am I doing now?

First, Credit leads Equity. Always.

Before you can even get your arms around software equities, the debt capital markets have to stabilize. That’s where I’m focused first—SAFETY—especially as I watch BDCs implode that have “modest” software exposure (see below chart). In case you’re wondering why, I helped launch and scale Solar Capital ($SLRC) while at Magnetar that we eventually took public in 2010. I know the game and the players. While I’m definitely stale, I’m now hand-sifting BDCs that throw off healthy double-digit dividends with ample coverage and debt capacity; trade at meaningful discounts to book; have limited software exposure; and sit in perfected senior-secured, first-lien position across highly cash-generative, well-diversified portfolios. Blackstone’s is the cleanest expression of that for me today—I’ve already bought some. Premier sponsorship, sub-30% software exposure, larger and more durable portfolio companies than peers, and a capital stack where Blackstone sits at “dollar one” within businesses that still trade at mid-teens free cash flow multiples. If software companies hit the wall—not my base case anytime soon—I’m comfortable Blackstone is likely money-good.

Below is a good overlay of how much destruction we’ve seen in this small pocket of the capital markets.

Second, Cover Shorts.
I’m doing this now. The short worked. It’s been a very productive tilt, and I know when I’m overstaying my welcome. I’m not here to play the “pro game” once the same trade I identified a year ago starts becoming consensus thinking. And firms like Citadel and Jane Street will pounce crowding folks like me out. I’m also contemplating covering more of Palantir in the STUPIDITY sleave.

Third, Prepare To Catch Falling Knives.
This is the hardest part. There are businesses I’ve owned before and still have enormous long-term conviction in like Netflix, Spotify, and Shopify. There are also SaaS names I’ve previously owned like Monday, and cybersecurity names like CrowdStrike that I believe will actually grow through this AI fear. I’m sharpening the pencil on all of these in my downtime and will likely pick a few over the next six months as the dust settles. I don’t care about catching the bottom tick, I care about catching the bottom multiple. I want to see the “white in the eyes” from core investors—not sure I’ve seen it yet. But we’re definitely due for a bounce. So traders, get ready.

It’s worth mentioning Weedmaps (MAPS). Now down 40% from December, it has been thrown out with the rest of software and cannabis. It’s not on my must-have list in the sector, but the stock is getting stupid cheap relative to what the business actually is. This is a cash-rich, category-defining platform that still sits at the center of consumer discovery and retailer workflows, yet it’s being priced like it has no future. When things get indiscriminately sold, you don’t need perfection. You just need the downside to be wrong. Don’t own it yet, but on my very short cannabis list.

Fourth, Press The MAG7 Short.
That’s an entirely different bet. I’m pressing it, as I get bigger in some of the MAG7 like Amazon. Flip back to my prior Seshes for more reasoning behind this.

4/END

This isn’t about calling a bottom or forcing a narrative. It’s about positioning for a regime shift in real time. Credit first, discipline second, patience third. Software will produce incredible businesses again, but the entry points will be earned, not gifted. Until then, I’m getting paid to wait, cleaning up what worked, and preparing for what’s next.

Big ideas take time. So does capital.

Onward,

SUNDAY SESH

In the past, change moved slowly where disruption felt theoretical and “on the come”—a distant risk that often took decades to matter. I lived this firsthand early in my career. As a example, Netflix was founded in 1997 with a day-one vision of an internet distribution model. Yet, it still took fourteen years to finally kill Blockbuster. Along the way, investors had ample time to react. Time to debate. And Blockbuster’s management had a lifetime to pivot. Sadly, it never did.

Today that luxury no longer exists. Ten years now collapses into ten months.

Transformational change is accelerating, and the forces driving it don’t ask for permission. Change is no longer incremental—it’s compressive. The distance between signal and outcome has collapsed, and the forces that matter most now often sit outside the company’s control. Whether you’re allocating capital as an investor or deploying it as an operator, outcomes are increasingly shaped by what starts at the edges. Industries and business models are no longer evolving at the margin; they’re being reshaped outright. Some opportunity sets expand. Others compress. Entire paths quietly disappear.

The hard part? Much of what we see is truly noise. Innuendo. FUD. But much of it isn’t. Those forces might be early, but dismissing the winds of change because the storm seems too far on the horizon is a death sentence. Eventually—and likely faster than you think— that storm is gonna land. Your job is to truly identify whether it’s simply noise in the distance that’ll dissipate, or a rich signal that’s about to blow your door down.

In this environment, while excellent company-level underwriting is still mandatory, it’s no longer decisive on its own. This is especially true in the public markets. What determines outcomes now is structure. Who sets the rules. Where capital can and can’t flow. Which behaviors are subsidized, constrained, or quietly made obsolete. These dynamics don’t show up cleanly in stale 10-Ks, models, or sell-side notes. They emerge at the edges—and by the time management and analysts fully engage, it’s often too late. If the Netflix–Blockbuster battle were playing out today, Blockbuster would’ve hit the wall before it even knew what hit it. See software today.

Since this Substack will always apply the subject at hand to cannabis, it’s worth level-setting why the periphery matters here too. Washington matters—clearly—and the firehose coming out of D.C. often preludes downstream impacts to our sector. Unlike AI or robotics, cannabis isn’t an exponential technology story. But to reemphasize a foundational part of my thesis, cannabis is a consumer story. And that consumer is being reshaped by transformational forces that start at the edges: greater control over personal health and longevity is driving substitution away from alcohol and certain Rx alternatives, while distrust of institutions and the rise of populism reinforce cannabis’ long fight to get government out of our lives. Different forces, same direction. You get the idea.

Last Sesh, I said I’d go deeper on the peripheral assumptions shaping how I deploy capital. Whether it’s investing across cannabis and CPG professionally, or allocating active capital through my SAFETY, SPIFFS & STUPIDITY framework personally, think of this as the “sausage-making” behind those decisions. This is the periphery work. And in this market, it’s no longer optional. It’s table stakes.

So grab your tray, roll up a fat J — and let’s go thru the assumptions that matter.

To be clear, each assumption could be their own SUNDAY SESH—perhaps I’ll dive deeper—but if you’ve been following me for a while across platforms you’ll understand how I’ve come to these conclusions with hard-data—and lived experiences—to back them up:

1. Beta (Still) Scares The Shit Out of Me

Passive investing works over long arcs, but market-cap-weighted beta has quietly become a concentrated trade where ~40% of the S&P500 continues to plow more capital into the Mag7 driven by one singular AI narrative. When narratives wobble, the same machine that forced capital in will force it out—and crowded momentum won’t absorb shocks gracefully.

Yes, beta still scares the shit out of me. That was on full display last week. That doesn’t mean I don’t own it. I do—mostly in passive 401Ks and long-duration vehicles that are structurally hard to move. But for the foreseeable future, every incremental dollar of capital at risk will not be invested in beta. You can do better.

2. Humans Can’t Think Exponentially

Markets consistently misprice exponential change because humans anchor to linear intuition. We rely on forward earnings multiples to assess “cheapness,” but when businesses compound (or shrink) exponentially, there will always be moments when companies look stupidly cheap and stupidly rich at the same time. I said it last Sesh, but I stand by my high conviction that this year we’re going to see constant paranoia and exuberance. Often, this will occur in the same sector. That’s why I firmly believe that calling quarters vs. years will matter a lot more this year. Result? More nimbleness. More volatility. And by extension, that often means more mispriced convexity.

3. Convexity Perpetually Mispriced

Convexity simply means non-linear outcomes—small inputs producing outsized results. Textbooks reduce it to options and volatility math, but that misses the point. I’m talking about structural convexity, created by incentives, positioning, and narrative risk. Professional investors aren’t paid to be early or last out, so capital clusters around consensus until it doesn’t. The result is “air pockets”: companies left for dead alongside companies that can’t do anything wrong. When the narrative breaks, price doesn’t adjust smoothly — it snaps, violently, in both directions. That’s why I’m drawn to “spiffs” that behave like an “option on an option” — where the cost to hold is trivial relative to the potential payoff. I’m fine owning something that does nothing for two years if there’s a real chance it eventually rips faces off. Opportunity cost in investing is simply overused. See cannabis.

4. Don’s Running It Hot

Yes, Don is still going to run it hot. Been saying this forever. Let’s not forget why: we can’t outrun our debt, we can’t balance our budget (regardless of who’s president or in Congress), and we can’t afford to take our foot off the AI gas to compete with China. Hard truths. Therefore, policy is pulling demand forward — and near-term growth will likely surprise to the upside, especially in infrastructure, re-shoring, and national security. That’s why I’ve tilted heavier on industrials, energy, materials and mining as you saw last Sesh. Don’t let the new Fed chair confuse you.

The irony? Much of what’s being funded is structurally deflationary. The cost of information, services, and eventually labor is collapsing. Moreover, parts of “GDP” will start to disappear. Like paying your lawyer $750/hr to read an NDA that can easily be digested in seconds. Similar to inflation (see below), our archaic GDP benchmark blasted on CNBC won’t be the future benchmark. Be careful of this narrative in 2026.

5. Scarcity Beats Abundance

Technology keeps deflating information and services, but the real constraint isn’t software—it’s physics. Energy, chips, land, water, permitting, metals, housing, and healthcare can’t scale exponentially. Capital flows where supply can’t respond overnight, because scarcity, not narratives, sets the clearing price. In 2026, you MUST focus on bulletproof, scarce assets. Anything that can get replaced will be, or will be questioned. While there will be "air pockets” especially in left-for-dead companies (see #3), the hurdle rate for structural losers will remain exceptionally high. Quality first, always.

6. Inflation Isn’t Gone — It’s Mismeasured

I’m tired of economists and officials hiding behind CPI like it’s gospel. Has your life gotten cheaper? Housing? Healthcare? Energy? Insurance? Services? CPI misses the inflation people actually feel. Yes, Trump’s agenda is trying to lower costs—credit card caps, housing relief, gas at the pump. Some of that helps at the margin. But zoom out and the picture is clear: the cost of the things that matter continues to inflate relative to wages and the dollar. Similar to point #5 above, it’ll be critical to focus on the companies that outrun and outprice inflationary forces.

7. The U.S. Is No Longer a Frictionless Safe Haven

This is the uncomfortable one. Global investors are slowly—but visibly—re-pricing U.S. risk assets. Not abandoning them. Not panicking. But questioning the assumption that the U.S. is the default safe harbor.

Look at the dollar last year. Look at U.S. equities versus other markets. The cracks aren’t catastrophic. But they’re real. Layer on protectionist approaches, then it becomes increasingly clear that every country’s priority is looking out for itself.

When confidence erodes at the margin, capital looks for alternatives. Capital isn’t fleeing the U.S., but it is questioning it. Exploding debt, long-duration risk, and diminishing returns mean confidence is eroding at the margin—and marginal capital sets prices. I standby my high conviction view that bulletproof dividends paid by bulletproof, growing companies are safer than 30 year treasuries. See XOM.

8. Fiat Is Dying

Global money supply is expanding again. You can argue about M2 as a tool, but directionally it still tells a story. While off to a horrendous start, it wouldn’t surprise me if Bitcoin is the best-performing asset class in 2026. And if it isn’t, I’m still comfortable allocating dollars to it over time. As AI becomes more agentic and tokenization accelerates, Bitcoin isn’t just a bet on the future. It’s a bet that the dollar’s purchasing power has seen its best days. It’s also a hedge against narrative whiplash in risk assets. I’ve said it before and I’m not bluffing: I buy Bitcoin every day. Not because it’s a trade. Because it’s duration.

You don’t need to agree with these assumptions. You just need to be honest about whether you’re underwriting them—intentionally or by default. In markets like this, structure decides outcomes long before narratives catch up.

Watch the periphery.

Onward,

SUNDAY SESH