Chris Jones built 22 cannabis retail stores by doing the opposite of what the industry rewards. He stayed profitable. He stayed boring. He stayed alive.
My guest on The Scaling CEO is Chris Jones, founder and CEO of Cannabis Express. In an industry full of land grabs and investor-fueled expansion, Chris took the unsexy path. He picked smaller markets, watched every dollar, and let cash flow do the funding.
That one decision shaped everything else.
The Counterintuitive Advantage of Having Less Money
Chris believes the early constraint was a feature, not a bug.
“So I think part of the reason why we’ve been so successful is that we didn’t have an enormous amount of money at the very beginning.”
He started in 2020, raised a small amount once, and then stopped feeding the company outside cash.
Instead, he let the business earn the right to grow.
“So all the growth has been funded through positive cash flow that we’ve had.”
This is a CEO choice, not a financial accident. It forces you to build a machine that can breathe on its own.
The Old Honda Civic Test
One of my favorite parts of the conversation was how Chris ties personal discipline to operating discipline. He does not separate them.
He told a story that explains his mindset better than any spreadsheet ever will.
“I know I was driving a really old Honda Civic for a long time and had almost half a million kilometers.”
It got to the point where his own staff did not recognize it as his car.
“I parked there and I was like we didn’t see any car there so no that’s no that’s that’s my car right”
That is not about humility theater. It is about refusing to confuse optics with progress.
He said it cleanly:
“Car for a thousand dollars or a car for a million dollars still gets you to the same place.”
The “Boring Markets” Strategy That Works
Chris avoids the places that look good in investor decks. He looks for the places that keep making money.
He expanded beyond Ontario into New Brunswick and found that a meaningful chunk of revenue came from there. His takeaway is blunt.
“It’s the kind of boring places that are usually the best places to go long term, right? Where they keep making money.”
This is the Walmart playbook. It is also a lesson many CEOs need to hear again.
Big cities invite big competition and big spending. Smaller markets give you room to operate without fighting someone with 10x your capital.
Hiring Timing Is a Scaling Skill
Chris sees a common mistake in early scale leaders: hiring an executive team before the business has earned it.
He described meeting a retailer with one store who already had the full corporate lineup.
“This is my CFO, my CMO, my person in charge of HR. was know, my legal was looking at them and I was like, you guys have one store.”
Then he delivered the punchline:
“Like, why do you have all your, why’d you hire all your friends?”
His approach is the opposite. He waits until the work is overflowing and then hires under pressure.
What this looks like in practice:
- Scale from 1 to 5 stores with scrappy coverage
- Feel the strain at 7 to 10
- After 10, build layers because the CEO cannot carry the day-to-day anymore
- Hire only when the role is real and the workload is proven
That is capital-efficient scaling. It is also emotionally harder because it demands patience.
Compliance in Regulated Markets Is a Relationship Game
Chris has operated across provinces with different licensing dynamics. He treats regulation like a system you learn, then repeat.
His point about regulators matters in any heavily regulated industry, not just cannabis.
“I think having an open relationship, if you can, with some of the people that are in charge of the regulations, is important.”
He also understands the gap between theory and practice.
“Some of the things that potentially are proposed don’t necessarily make sense in practice.”
CEOs who treat regulators as enemies usually pay for it later. CEOs who treat them as stakeholders tend to keep operating.
Muay Thai, But the Real Lesson Is Disconnection
Chris is undefeated in amateur Muay Thai, but the leadership insight he shared was not about fighting. It was about stepping away from constant input.
“So think disconnecting is very important.”
And he was specific about activities that remove the phone entirely.
“But when you’re doing yoga, Muay Thai, you don’t have your cell phone in your pocket.”
A lot of CEOs pretend they can always be on and still sharp. They cannot. Recovery is part of performance.
AI as a Practical Retail Weapon, Not a Fantasy
Chris is not pitching AI as magic. He is using it to move faster through operational reality.
He said something CEOs should take seriously:
“AI comes up quite a bit and I read a lot about AI and a lot of the companies that have invested a lot in AI haven’t really seen any returns on it as of yet.”
Then he explained what he actually does with it. He uploads real data and asks targeted questions that save time.
Examples he gave include:
- Finding employees who give more discounts than others
- Understanding margins by product category
- Adjusting staffing and store hours based on peak patterns
- Flagging inventory older than six months and deciding discount strategy
He described the old way and the new way simply.
“So it saves like we can do it, you know, manually in Excel, just digging through a length of the tables, but it does save a lot of time.”
This is what I want CEOs to notice. AI is not only a customer-facing feature. In many businesses, the first wins are internal, boring, and profitable.
Listen to the Full Episode
Chris Jones scaled Cannabis Express by acting like cash is oxygen and discipline is strategy. That is a good reminder in any market, regulated or not.
If you are scaling a location-based business, this episode will challenge your instincts in the best way.
I’m Glenn Gow. I coach CEOs who want to scale with confidence and stay in control of cash, people, and execution. On my podcast, I break down the strategies serious operators use to grow faster without burning the business down.
Listen to the full episode to hear how Chris built a 22-store cannabis retail chain without outside capital, why boring markets win, and how he stays composed under pressure as a CEO.
