I was giving a presentation to a group of entrepreneurship students at a nearby university. As I was sharing the story of my personal entrepreneurial journey, I mentioned I’d launched my first startup when I was 20. Since I recently turned 40, it meant I’ve reached the point in my life where I’ve been building companies longer than I haven’t.
“Gosh,” I said after the unexpected moment of realization, “I guess I’ve been building companies for more than half my life. When did I get so old?”
Everyone chuckled politely, and I went back to giving my presentation having completely forgotten about the moment. However, the next day I got an email from someone who’d been in the audience. She thanked me for speaking with her group, and then she asked the following question:
“You mentioned you just turned 40 and that you’ve been building startups since you were 20. If you could get in a time machine and travel back to your first day as an entrepreneur, what piece of advice would you give yourself?”
I’m ashamed to admit I didn’t respond to the email for nearly two weeks, but it wasn’t for lack of trying. In fact, I drafted responses at least a half dozen times, and none of them seemed right because the question turned out to be much harder to answer than I’d expected.
In one draft, I wrote that the most important piece of advice was a lesson about working with other people. In another draft, I focused on not taking things too seriously. In a third draft, I gave some hackneyed advice about enjoying the journey.
Everything I wrote felt cliched. The person who’d asked the question would have gotten better advice asking ChatGPT.
Eventually, however, I felt like I hit on a useful piece of startup wisdom that the 20-year-old version of me might actually find useful. I was even proud of myself for coming up with it until I remembered I can’t actually travel back in time to share the advice with my younger self. I can, however, share what I wrote with all of you, so that’s what I’m going to do.
