Chris Joseph had less than twenty dollars in his checking account.
Not during some cautionary tale about what happens when you don't plan. During the building of what would become Wyld — 12 of the top 13 cannabis edibles SKUs in the country, every recreational state, Canada, and a beverage line still expanding. The twenty bucks in the account came after he sold the house. After he maxed out the credit cards. After he'd gone so far past the point of comfortable retreat that retreat stopped being a real option.
"When your back's against the wall, you have to make it work. We didn't have another option."
I've thought about that sentence since we recorded. Not because it's the romantic version of startup risk — it is, and everyone loves that story. I've thought about it because the thing he's actually describing isn't recklessness. It's a very specific kind of strategic clarity that most people never access because they never get uncomfortable enough to need it.
The difference between Chris at twenty-something with an empty checking account and the version of that story that goes wrong isn't luck. It's the thing underneath the bet — whether you genuinely believe the category you're entering can support what you're building, or whether you're just willing to lose everything on a feeling.
Chris believed the category. And his belief wasn't emotional. It was structural.
The bet wasn't cannabis. It was the gap in the shelf.
When Chris and his co-founders decided to get into cannabis around 2015 and 2016, they didn't know exactly what they were going to build. Dispensary, grow operation, packaged goods — the model wasn't obvious yet. So they did what smart operators do before they commit: they looked at the regulations, projected forward, and eliminated the options that had structural problems built in.
Farming was out. An agricultural category that can't export — that has supply trapped inside state lines — will produce surplus, which drives down price, which kills margin. That's not a risk. That's a math problem. Retail was out too, for its own reasons.
What they had from Cascade Spirits, Chris's craft liquor company, was packaged goods experience. They understood how to take a raw material, build something around it, package it so a consumer trusted what they were picking up, and put it on shelves. They understood distribution, regulatory relationships, the difference between revenue that builds equity and revenue that just moves money around.
So when they looked at cannabis, they didn't ask what should we build. They asked what can we build that the market doesn't have yet — and what nobody had yet was a cannabis edible brand that looked trustworthy on a shelf. That didn't require shame at the register. That a person who'd never bought cannabis before could pick up and understand.
"I didn't know what I was buying when I went to a dispensary before we launched."
That sentence is the entire product thesis. If the founder was confused as a non-consumer walking into a dispensary, the average first-time buyer was lost. The packaging wasn't welcoming. The products weren't consistent. The experience sent you home uncertain about what you'd actually taken and what to expect. Chris looked at that shelf and saw exactly what Mike Cessario saw when he looked at the water aisle — a commodity category where brand and trust would do most of the deciding.
Wyld was the bet that someone was going to build a reliable, clean, fruit-forward edible brand that made cannabis feel accessible. Might as well be them. So he sold the house.
Going wide teaches you to go deep
The lessons from Cascade Spirits weren't just operational. They were strategic, and the most important one almost cost him the spirits company before it became useful in cannabis.
On the spirits side, Chris went wide too fast. Wild Roots Marionberry Vodka is a great product — marionberry is a cross between two blackberries developed at Oregon State, and if you've had one, you know there's nothing like it — but try explaining what a marionberry is to someone in New Jersey. You can't just sell the product. You have to sell the category, the fruit, the Pacific Northwest identity, the whole context. Which means you're spending education dollars in markets that aren't ready to receive them, while your own backyard still has room to grow.
"We were spending extra money on education and it still wasn't clicking the way it needed to. And where if we spend that same dollar here, we get much more of a return."
This is the lesson that transferred directly into how Wyld was built — methodically, state by state, building genuine velocity and pull-through before expanding to the next market. Not first to market everywhere. First to win deeply somewhere, then carry that brand equity to the next state. They weren't in the Northeast when we sat down. They're entering it now, after the West Coast, after Colorado, after proving out the model so many times that the brand walks in with momentum already built.
I've seen the opposite play out in my own investing. I've watched founders — and been one of the investors cheering them on — expand geographically before the core market was actually saturated, because "national presence" looks good on a deck. The costs compound fast. The per-unit economics in the new market underperform, you burn cash to maintain momentum, and you come back to your home market to find a competitor has taken share while you were gone. Going wide before you've gone deep isn't ambition. It's impatience dressed as ambition.
PULL QUOTE: "Revenue is only as great as the profit it brings. And that profit is really only as meaningful as the impact it makes." — Chris Joseph
The regulation is the moat, if you survive it
There's something about this industry that separates it from almost every other CPG category I've looked at, and it's the thing that made Chris's bet both riskier and, ultimately, more defensible.
Every state Wyld operates in is, operationally, a different country. You cannot cross state lines with THC products. Which means every new market isn't a distribution expansion — it's a new manufacturing plant, a new regulatory relationship, new compliance filings, new supply chain. The CapEx to enter a state is real. Most brands, especially early-stage ones, can't afford to build the operational infrastructure in five states simultaneously. So they don't.
What that creates is a compounding advantage for whoever survives it. Wyld has 12 of the top 13 edible SKUs nationally not just because the product is good — though it is — but because they have manufacturing infrastructure in enough states that their brand has national recognition while competitors are still trying to figure out state three or four. The barrier to entry looks like regulation. The moat it creates is operational scale that took ten years of disciplined CapEx allocation to build.
The Delta-9 beverage line is the most interesting next chapter of this, because it ships across state lines under the farm bill. Chris wouldn't say it directly, but what Wyld is becoming in that space — production infrastructure across the country, brand recognition, relationships with retail and distribution partners — starts to look a lot like what the spirits distributors built before anyone realized that was worth building. I have a conversation to finish with him offline about exactly that.
What I'd do with this if I were starting from zero
Three things from this conversation that I think apply beyond cannabis — to any founder going into a heavily regulated or nascent industry, and to any athlete thinking about where to put real money:
- Understand what you're actually buying when you back an operator in a regulated category. With Chris, the spirits experience wasn't incidental — it was the unfair advantage. He already had OLCC relationships, existing supplier contacts he could route through Cascade before cannabis vendors were willing to sell directly, and a working model for building a packaged goods brand from scratch. The $150K seed round went as far as it did because the founders already knew how to spend it. When I'm evaluating a cannabis deal, or any highly regulated category, I'm looking for founders who've navigated a comparable regulatory environment before. The product often matters less than that.
- Don't confuse going all in with not having a thesis. The house and the credit cards are the dramatic part of Chris's origin story, and they deserve to be told. But what made that bet survivable wasn't courage — it was the structural analysis he did before committing. Farming would have supply surplus problems. Retail was thin margin and execution-heavy. Packaged goods in a category with no trustworthy brand was the gap. He sold the house after identifying the gap, not before. I've seen athletes and investors go all in on passion without doing that analysis, and it looks the same at the starting line. It looks very different two years in.
- The frugality compounds the same way the brand does. Wyld never took VC money. Never did a SPAC. Never needed outside capital to prove the model, because they grew within their means — and I know how rare that is, because I spent from 2010 to 2012 sitting in cash because I didn't have the right team yet to invest intelligently. That cost me real money in a missed rally. But the flip side of not having the right team is also what I watched a lot of early cannabis companies do — raise institutional money, lose control of the cap table, lose the ability to make long-term decisions because someone with a three-year fund horizon is now in the room. Chris kept the cap table tight. That means Wyld's long-term decisions are still Wyld's to make.
The other thing Chris said that I want to sit with: "If Wyld can be looked at as more than edibles, we've made it." He means it from a community and brand perspective — the expungement work, the sustainability commitments, the equity initiatives in an industry that has a real and documented problem with who gets to build wealth inside it. But I think it's also the right business instinct. The brands that last aren't the ones with the best product in one category. They're the ones that become something people trust broadly enough to follow into the next one.
He started with a dream of selling a million dollars worth of edibles.
Now he wants to be the InBev of cannabis.
The gap between those two sentences is what a sold house and twenty dollars in a checking account buys you, if you've done the work to know exactly what you're betting on.