The Hardest Lesson from 25+ Years of Failed Experiments

I started hustling as a teenager back in 1998 with a website design side gig. My biggest client was the local computer store where I hung out, tinkering with hardware while building templates for their “build-your-own-site” tool. After that, I assembled custom PCs for friends and random customers.

None of these made serious money, but they stacked skills and scars I’d cash in later.

My most profitable teenage venture? Hemp jewelry. I bought a huge lot cheap on eBay, started selling at school, and bombed until I recruited Amy. She was a fearless, unapologetic closer who moved more in a day than I did in a week. That taught me early: sales ability trumps everything else when you’re starting out.

The Pattern of the Next Two Decades

For the following 20+ years, I kept experimenting: wrote books, ran blogs, consulted, launched digital products. Some flickered, none caught fire.

The common thread? I tried to serve everyone. Too broad, too vague, too scattered.

What I’m Doing Differently Now

This time, I’m slowing down and niching deeply.

I’m not chasing quick wins from massive audiences. I’m building proven, sustainable residual income streams for tightly defined groups, starting with people exactly like me.

This blog is a perfect example. Personal finance is brutally competitive, so I’m not here to compete on generic advice. I’m writing to connect with driven professional men who want to stack residuals intelligently… and open doors to partnerships, deals, and investments down the road.

Future projects will follow the same rule: solve painful problems I’ve lived myself.

• Recruitment process outsourcing (RPO) for high-turnover hospitality businesses
• Specialized accounting and FP&A for real estate developers
• Outsourced sales teams for service-based companies
• Custom digital interfaces built on top of clunky platforms (ATS, accounting, CRM)

These aren’t hypothetical. They’re itches I’ve scratched (or still am scratching) in my own career.

And yes, there will be new experiments along the way, like ice vending machines, real estate syndications, and whatever makes strategic sense. Some will pivot the entire trajectory.

The Guiding Principle

Pick a specific customer with a painful, well-defined problem. Offer a clear, high-value solution. If the market isn’t big enough to support real income, walk away fast. Don’t force square pegs into round holes.

That’s the hardest lesson from decades of swings and misses. Everything I’m building now follows it.