By the time I was 16, I had already sold my first businesses. They were a series of professional wrestling websites, including Wrestler Zone, Wrestling Inc. and AWW Wrestling, which I had promoted through IRC chat channels on mIRC. They went to CraveOnline. For a teenager, that should have felt like the end of something. It felt like the first day of the next thing.
That pattern has repeated for my whole career. I have written about the philosophy behind it before. This piece is about the practical side: what I have actually done the day after a milestone, and what I would tell someone who just hit one.
Decide Where the Win Goes
By my late teens I had made more than a million dollars. My first company, Emblaze, was an advertising business: I worked with several ad networks and had high-traffic sites under me, earning on visits, clicks and time on site. But making money and keeping it are different skills. The first million I actually had saved came at 21.
I was living in Vancouver then. My first real money went into cars, and into savings and inventory for the business. I am not going to pretend the cars were a strategy. The savings and the inventory were. They let the next business start from a stronger position than the last one.
The practical lesson: before you celebrate, decide what part of a win goes back into the work. A milestone that does not fund the next step is just a nice memory.
Let One Business Build the Next
My best transitions came from building the next thing out of the last one. In 2010 I opened Winny’s Vitamins & Supplements, an online store and eBay shop selling the major nutraceutical brands. In 2011 it led directly to KORE Fit Living, a Canadian supplement and fitness franchise.
Winny’s taught me the products, the suppliers and the customers. KORE turned that knowledge into a system other people could own. I sold the first franchise before our first corporate store opened, and in the first year about 30 people applied for franchises. None of that would have been possible if I had treated Winny’s as the finish line.
Know When to Walk Away
Not every next step is a bigger version of the last one. Sometimes it is an exit. From 2000 to 2002 I was a partner and the lead technologist behind Best Player Casino and Best Player Sportsbook, among the early online casinos and sportsbooks. Then I left. Incredible Entertainment, the satellite television business I launched in 2001, ran until 2014.
An ending is a decision like any other. The question worth asking is whether the business still deserves the hours I give it, or whether those hours would build more somewhere else. Leaving well is part of moving forward. Staying too long out of pride is how a milestone turns into a ceiling.
Treat a Big Milestone as New Obligations
In 2022, Limitless X became a public company through a share exchange with Bio Lab Naturals, Inc., and was renamed Limitless X Holdings Inc. I am its Chairman and CEO. People sometimes describe a listing like that as arriving. In practice it adds obligations: a board, public filings and a standard of disclosure that a private company never faces.
That is true of most big milestones. A promotion, a funding round or a first major client does not reduce the work. It changes the work, and usually adds to it. The sooner you accept that, the sooner you can plan for it.
A Short List for the Day After
If you just hit a milestone, this is the list I would hand you:
- Write down what the win actually proved, and what it did not.
- Decide where the proceeds go before spending any of them.
- Hand off the parts someone else can now run, so my time goes to what comes next.
- Pick the next level while the energy is still there.
Sleep is the part I still struggle with. My mind does not stop, and I am always thinking about ideas and work. That is exactly why a list helps: it turns restless energy into a next step.
The longer version of how I think about this is in The Pursuit Never Ends. The early ventures mentioned here are profiled under Best Player and KORE Fit Living. Every one of those milestones felt like a finish line for a day. None of them was.
