I recently listened to three podcast episodes, all with bootstrapped founders over the age of 40:
It's interesting to see how differently this stage of life is compared to our 20s and 30s. (I'm 44). An Evolving Definition of Success:"I've been at Summit for 5 years. My last company took 15 years, and I didn't want that again. At 43, with three kids in high school and one in college, I need something that works on my timeline. I've had success before – doing it again at the same scale doesn't make sense; time matters more now. So, it became logical to find something that better capitalizes on my talents and time. It's bittersweet, but it makes sense." – Matt Wensing
Life Stage Considerations:"My oldest is 12, and I have certain financial goals that I want to accomplish before they go away to college. It's this 6-year window in my mind, and I do a lot of my planning and thinking around that time frame." – Jordan Gal
Different Decision-Making:
Leveraging Wisdom and Experience:"In your 40s, 50s, and 60s, your wisdom is higher, your pattern recognition is higher, your teaching ability is higher." – Arthur Brooks
A few thoughts from me:Something changes once you turn 40. Your definition of success evolves – it's not just about "replacing your salary" anymore. You want meaningful outcomes that justify the time and energy investment for you and your family. I'm still ambitious, but I have a clearer understanding of what different paths require. I've learned what things cost (in time, energy, and personal life) Jon and I started Transistor in our late 30s. We knew it would be at least 1-2 years of intense work to bootstrap a profitable business. And we got lucky: our "calm company" phase came right when we turned 40. Could we do it again at 44? I'm not sure we could do it the same way. If we started again, we'd need more resources and a different approach. There's a saying: "Youth is wasted on the young." But maybe experience is wasted on the old! We have all this accumulated wisdom; it's time to use it as leverage. One final thought: I greatly admire folks who "know when it's time to move on." We don't talk about "retirement" or "post-founder life" enough in our circles.
Links: I'm curious: if you're over 40, what's your take on being a founder at this stage of life? (If you're under 40, does this change your thinking about your future?) Cheers, 🗣️ Talk about this newsletter on Bluesky |
I'm the co-founder of Transistor.fm (podcast hosting and analytics). I write about SaaS marketing, bootstrapping startups, pursuing a good life, building calm companies, business ethics, and creating a better society.
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