Hitting it big doesn’t mean you’ve crossed the finish line. Bo Bennett, a guy who sold his first major company for $20 million, could’ve stopped right there, but instead, he launched into one reinvention after another. We talked about his journey on my Never Been Promoted podcast, and the stories he shared weren’t about the big dollars he made but rather about what came after, the messy parts, the pivots, and how he kept that entrepreneurial fire burning. Let’s dive into two big insights from Bo’s path—and why they might matter to anyone with a bit of entrepreneurial grit.
Knowing When to Cash Out—and Why Timing is Everything
The first thing that strikes you about Bo’s story is how he made his big break during the internet boom. Back when “dot-com” was still a shiny, new term, Bo was building a web-hosting business. Demand was wild; companies everywhere needed to get online, and Bo was right there to catch the wave. But unlike a lot of folks at the time who got swept away in the hype, Bo kept his eyes open. He saw the writing on the wall.
“I knew the bubble would burst,” Bo told me. “People were throwing insane money at companies with no revenue. It didn’t make sense, and I saw it couldn’t last.” Instead of riding it out and hoping for the best, he decided to sell—$20 million in his pocket right before the dot-com bust left so many others empty-handed.
The lesson here? Timing isn’t just luck; it’s about paying attention, trusting your gut, and knowing when to get out. Bo’s not saying everyone should sell their business the minute things look good. But he saw a frenzy for what it was, and he got out when he knew he could secure a big win. Not everyone does that. Most folks hold on, hoping things will just keep going up. Bo didn’t let the hype blind him. He saw an opportunity, cashed in, and secured a big chunk of change that let him do what came next.
Key Takeaways from Our Discussion:
- Be honest with yourself about market conditions; hype isn’t a reason to hang on.
- Cash deals offer security—sometimes, stock-heavy deals are more risk than reward.
- Trusting your gut can save you; Bo saw the risks and made the leap, and it paid off.
The Real Power of Reinvention: From Business to Psychology
So what do you do after a huge payday? You’d think Bo would have hit the beach, right? But instead, he went back to school and earned a PhD in psychology. Not exactly the next logical step for a tech entrepreneur. But for Bo, it made sense. He’d always been interested in how people think, so he used his time and money to dive into it.
“I wanted to make money early on, and I knew business was the way,” he explained, “but I had this love for psychology I’d never pursued.” Instead of jumping right back into business, he took the time to explore his interests, which actually paid off in unexpected ways. Bo’s understanding of human behavior, the way people think and act, ended up helping him later when he returned to tech and business.
Bo’s story reminded me of something I think a lot of entrepreneurs miss: Sometimes, the best way to grow isn’t just doing more of the same thing. It’s about stepping back and exploring what you’re genuinely curious about. That curiosity led Bo into AI, where he now runs a publishing company that creates books using AI—another tech-driven venture, but this time with a very human touch.
What I Learned from His Experience:
- Exploring interests outside of your field can give you a fresh perspective when you return.
- Real growth isn’t about doing the same thing again; it’s about stepping back and taking on new challenges.
- Curiosity isn’t just a luxury—it can be a real driver for your next big idea.
Reflections from the Interview
Talking with Bo gave me a fresh take on what it means to be flexible and keep pushing forward, no matter how many wins you’ve stacked up. Bo’s path isn’t about just making money; it’s about continuously challenging himself and staying curious. And for anyone looking to do more with their lives, he’s a prime example that there’s more than one way to keep climbing.
Here’s What I’m Taking Away:
- Keep the bigger goal in mind: Bo’s ultimate aim was growth, not just hanging onto his first success.
- Don’t get too attached to any one idea: Bo’s willingness to leave one business behind for another made his career so varied and interesting.
- See failure as just another step: Not every project Bo took on was a win, but he kept moving forward.
- Stay curious, always: His dive into psychology was unconventional, but it fueled his later ventures.
- Know when to walk away: Selling his first business at the right time gave Bo the freedom to experiment, try new things, and take risks most of us only dream of.
Final Thoughts
Listening to Bo’s story, I realized that his journey isn’t a one-size-fits-all playbook. It’s a reminder that success doesn’t mean stopping; it means staying curious and hungry and letting yourself explore what excites you next. For Bo, that’s been everything from psychology to AI publishing—and who knows what’s next? For anyone out there who’s reached a milestone, ask yourself, “Is this it?” Because Bo’s story shows that there’s always a new frontier.
CONNECT WITH BO BENNETT:
Website: https://www.archieboy.com/ | https://bookbud.ai/