I recently listened to three podcast episodes, all with bootstrapped founders over the age of 40:

• ​Paul Jarvis has retired from Fathom Analytics​
• ​Matt Wensing steps down from Summit, takes job with Customer.io​
• ​Brian Casel and Jordan Gal talk about building SaaS at this stage of life​

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:

• All three episodes showed how founders over 40 are evolving their definitions of "success."
• Your definition of success at 20 often differs from how it looks at 40.
• As you age, you're more judicious about where you put your energy.
• 40+ founders are ready to have more time outside of work and be with their kids, especially before going to college.
• Any time investment at work has to feel worthwhile and meaningful.
• There's less of a willingness to "grind it out."

Life Stage Considerations:

• Family obligations and priorities are prominent (kids in high school/college).
• Almost everyone (myself included) thinks that their kids' going to college is a significant milestone.
• Financial responsibilities are different - 40+ founders seek more stability and predictable income.
• Time horizon perspectives have shifted - founders over 40 think in 5-10 year blocks rather than indefinite futures.
• In your 40s, you realize you don't have an indefinite runway. Several people mentioned not wanting to embark on another "15-year bootstrap journey" at this stage.

Different Decision-Making:

• In your 40s, you have some accumulated wisdom: you recognize patterns faster and are more willing to change course.
• Less emotional attachment to specific business models/approaches.
• More emphasis on pragmatic decisions vs. proving yourself to others.
• Better at calculating the "expected value" of different paths and a better understanding of what different growth paths require.
• Willing to consider alternative paths (acquisition, joining larger companies)

Leveraging Wisdom and Experience:

• It's time to leverage our skills effectively rather than proving they can do everything
• Founders at this stage are willing to join larger organizations where their skills can have more impact
• Understanding that sometimes being part of a bigger system can create more value

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:

• ​Listen to all three episodes on Huffduffer​
• Or, add this RSS feed to your podcast player​

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,
Justin Jackson
​
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