The Entrepreneur’s Timing Problem: Why Your Best Idea Might Just Need Better Timing
As an internet entrepreneur with over 30 years of experience launching products, building companies, and learning through failure. I’ve sold six businesses and launched everything from apps to podcasts to publishing ventures. And the single biggest lesson I’ve learned isn’t about having the best idea—it’s about timing.
Timing is what separates the home runs from the strikeouts. It’s the difference between being too early, too late, or landing perfectly on the wave. I’ve experienced both sides of this equation, and I want to share what I’ve learned so you don’t have to waste years figuring it out.
The Cost of Bad Timing
Back in the late ’90s, I partnered with a programmer to build a multiplayer game site. We were ahead of the curve, which sounds good in theory. Except we were too ahead of the curve.
We spent time and money acquiring users, adding features, and trying to sell the concept to major search engines. Yahoo, AOL, everyone said no thanks. And then suddenly, after I’d given up pitching, the right buyer showed up. But by then we’d left performance on the table.
Then there was Virtual-Whassup.com, my greeting card site built around the viral Budweiser “Whassup?” campaign. The campaign hit in December 1999 and took off like a rocket. I jumped on the trend in 2001 and built a site where people could email funny animated greetings.
Except I was two years too late.
The momentum was gone. The novelty had worn off. I kept the site online as a humbling reminder that not all ideas are bad ideas—sometimes they’re just mistimed.
What Good Timing Actually Looks Like
Then came The Bad Crypto Podcast. My co-host Travis Wright and I launched it because we were fascinated with Bitcoin. We felt there had to be others like us who wanted to understand it, learn about it, and explore it in depth. And the timing was perfect.
That podcast led to a book deal, speaking opportunities, and years of growth. Not because the idea was original—there were plenty of crypto podcasts. But because we struck at the moment when curiosity was at its peak and the audience was hungry for perspective from someone experienced in online business.
The difference between those failures and that success wasn’t luck. It was understanding how timing works and learning to recognize when the conditions are right.
The Practical Playbook for Timing Your Moves
Watch the trends, but don’t chase them blindly. Before I dove into viral ideas, I learn to watch what’s heating up in my industry. Check social media, industry news, Google Trends. But here’s the key: you’re not looking for what’s trending right now. You’re looking for the wave that’s forming, not the one that’s already crashed.
Test small before you bet big. I released an AdSense Secrets ebook before committing to a massive second edition. That small test showed me what worked and what needed improvement. Try a limited launch, run a poll, get feedback from your network. If it clicks, you scale. If it doesn’t, you pivot without burning resources.
Build anticipation before launch. We teased the podcast’s evolution with early access for committed listeners. The key is announcing early, then delivering when momentum peaks. Let the idea simmer in people’s minds before you ask them to act.
Know when to pivot when the timing’s off. If sales are flat or feedback is cold, that’s not necessarily a death sentence. It might just be poor timing. Adjust the angle, the price, the positioning, and try again.
Trust your gut, but verify with data. Travis and I felt Bitcoin would resonate with people like us. That hunch was right. But we also watched the numbers—engagement, download growth, listener feedback—to confirm the timing was working.
Learn from the misses. My book pitch during a publishing slump taught me to watch for the right season to pitch. Every timing failure is data if you’re willing to examine it honestly.
The Real Payoff
Good timing opens doors you can’t predict. My AdSense ebook success led to a New York Times bestselling book, which led to an international speaking career. But none of that happens without the timing piece in place.
I’ve watched a 40-year-old hold off on a tech startup until funding became available, then thrived. I’ve seen a 50-something artist time a gallery show with a local festival and sell out. The pattern is consistent: those who master timing turn risk into reward.
Here’s what I want you to walk away with: timing is not some mystical thing that either you have or you don’t. It’s a skill. You develop it by watching trends, testing early, learning from failures, and trusting your gut while paying attention to the data. It’s the difference between having an idea and having a successful product.
The question isn’t whether you have a good idea. The question is: when is the right time to bring it to market?
If you want to explore this further, check out my upcoming book AI Made Simple, where I dig deeper into how to position your business and ideas for maximum impact. Or tune into my podcast for ongoing conversations about building in the real world.
