CANNABIS MSB I EST. 2013

From Chaos to Clarity: How My Cannabis Journey Sparked the Creation of HighDay

In 2013 I jumped headfirst into the cannabis industry as an operator. This was before legalization in most places, when just running a delivery service meant dodging government raids, making deals in parking lots, navigating shady banking, and praying your text platform didn’t get shut down overnight.

The Reality Check – The $45 Problem

One night around 2 AM I sat slumped in my office chair staring at a spreadsheet. We were spending $45 to get a new customer who’d maybe spend $65 one time… then 70% of them ghosted. Poof.

I could feel my future wife and kids sleeping in their rooms, my responsibilities weighing down on me. Every day I was risking everything, working 80-hour weeks, and actually losing money on most customers.

The Tech Handcuffs

I Couldn’t use Facebook Ads, they banned us. Email platforms? Shut down. Texting? Constant compliance worries.

So what’d I do? Cobbled together a stack of random tools. CRM over here, a clunky text tool over there, email buried in a corner. Nothing talked to each other. It was chaos and a time suck.

The Spark

One thing stood out. The few customers who did come back again and again? They got personal follow-ups; from me. Not generic blasts. Not discounts. Real, human connection.

But I couldn’t scale that. There weren’t enough hours in the day.

At the time, I didn’t have the tools, clarity, or time to build a full system. I knew what wasn’t working. But the solution? I wouldn’t crack that until much later.

What I had was the seed of an idea: loyalty is personal. And it can’t be an afterthought.

From Hustle to High Times

Fast-forward to 2018, rec legalization in California. We scaled hard and became a multi-state operator, then took the company public in Canada in 2019.

Retention was a piece of the puzzle, but not the reason we made it. It was timing, strategy, partnerships, grit. AND having great products that people came back for.

Exit + Next Chapter

I exited that business in 2021. It had been an almost 10-year journey, and I was ready for a new chapter. We had some wins, but the full picture was rough; Covid, partner graft, internal corruption, and the kind of industry chaos that chews up good people. In those years, I knew many operators who folded or were driven to suicide. After I left, the company completely imploded.

Looking back, we never fully solved the retention and reputation puzzle. That became crystal clear once I stepped away.

So I made it my mission to fix what broke us. I took everything we learned; the pain, the false starts, the near misses and turned it into something real.

That’s why I built HighDay.

Enter: HighDay

I started consulting, but kept seeing the same problems. Different brands, same pain.

So I built a team and the thing I wish I’d had back in 2013.

HighDay isn’t another CRM. It’s your unfair advantage.

We built it to:

Bring customers back 5x or more
Keep it 100% compliant
Sync SMS, email, wallet loyalty, social, reputation, chat and more all in one place

That’s when I finally created the High Five Method™

5 key visits that matter most
5 distinct milestones in the customer journey
Powered by 200+ automated, personalized touchpoints via email, SMS, and push messages

Every purchase has its own flow. Every message is engineered to feel human, timely, and relevant. Because loyalty doesn’t happen by accident; it’s built on purpose.

This is what actually worked. Not a bunch of incohesive tools. Not luck. A smart system built for cannabis, from the ground up.

Why I Keep Coming Back

I’ve been an entrepreneur since 1986. Built my first company with a fax machine and a dream. Over the years, I’ve launched businesses in tech, fitness, finance, and more.

But nothing’s tested me like the cannabis industry. Not even close.

This industry’s a beast. The rules change weekly. The platforms don’t want us. The banks play games. And yet… I keep coming back.

Why?

Because building in cannabis is more than business, it’s personal. It’s rebellion, it’s healing, it’s legacy. And even after everything I’ve done, I still believe with all of my heart that cannabis should be accessible to anyone who needs it.

The difference now? I don’t have to do it alone.

HighDay lets me help other dreamers build too. Operators who deserve better than what has been available. I know you’re hustling hard, feeling stuck, understand that there’s got to be a better way.

Now, I get to be part of their growth while continuing my own. And that, to me, is the real win.