Ben, really enjoyed this. Thanks for pulling together such a strong take on founder archetypes and the bias we carry into backing them.
As someone who founded my first company at 41 and have since gone on to start others—while also stepping in as a hired-gun CEO for two turnarounds with multiple exits along the way, I can’t help but lean into your “age doesn’t matter” thesis. It absolutely doesn’t, at least not in the way many assume.
I’m also caught, in today’s world, by the sheer pace of technology and the pervasiveness of AI shaping virtually every aspect of industry. At a recent investor forum, I watched brilliant young founders pitch their ideas, and the enthusiasm in the room was contagious. However, what I couldn’t help but reflect on was the other side of the equation: how often these founders lack leadership maturity. Not in a malicious sense, just the natural naivety of not yet having lived through the complex cycles, crises, and recoveries that ultimately shape resilience and judgment.
A few reflections:
* I often think about Colonel Sanders launching KFC’s franchise business in his 60s, a vivid reminder that meaningful startup success can come later, not just in your 20s or 30s.
* Starting later gives you advantages: lessons learned, resilience built up, and a network you didn’t have in your 20s. Those pay dividends when the roller coaster hits.
* The “young founders are fearless” narrative undervalues mature confidence. Fearlessness isn’t the absence of fear; it’s knowing how to act despite fear.
* Sometimes the very investor hesitancy around founders who are “too old” becomes a filter; if you can get past that bias, your conviction and execution shine brighter.
So yes: there’s no perfect founder. But count me in as someone testifying that there is power, clarity, and brilliance that come with founding (or serial-founding) later in life, especially when combined with the perspective to recognize both the genius and the limits of youth.
Cheers for this + looking forward to more of your essays.
Thanks Ben. I also think Silicon Valley has demonized lifestyle businesses, they're not deserving of the "startup" title, and unless you're 22 and eating pizza and beer for breakfast, sleeping 2 hours per night under your desk and haven't seen the light of day in 7 months, you're not worth investing in. That narrative still runs very strong, despite the data you share. Reid Hoffman is a huge offender in this narrative. I also find the bias against people with families is fascinating, even though what you have to do to work full time AND manage kids, sleep deprivation, competing schedules, etc makes people phenomenally good at time mgmt, efficiency, and prioritization.
Ben, really enjoyed this. Thanks for pulling together such a strong take on founder archetypes and the bias we carry into backing them.
As someone who founded my first company at 41 and have since gone on to start others—while also stepping in as a hired-gun CEO for two turnarounds with multiple exits along the way, I can’t help but lean into your “age doesn’t matter” thesis. It absolutely doesn’t, at least not in the way many assume.
I’m also caught, in today’s world, by the sheer pace of technology and the pervasiveness of AI shaping virtually every aspect of industry. At a recent investor forum, I watched brilliant young founders pitch their ideas, and the enthusiasm in the room was contagious. However, what I couldn’t help but reflect on was the other side of the equation: how often these founders lack leadership maturity. Not in a malicious sense, just the natural naivety of not yet having lived through the complex cycles, crises, and recoveries that ultimately shape resilience and judgment.
A few reflections:
* I often think about Colonel Sanders launching KFC’s franchise business in his 60s, a vivid reminder that meaningful startup success can come later, not just in your 20s or 30s.
* Starting later gives you advantages: lessons learned, resilience built up, and a network you didn’t have in your 20s. Those pay dividends when the roller coaster hits.
* The “young founders are fearless” narrative undervalues mature confidence. Fearlessness isn’t the absence of fear; it’s knowing how to act despite fear.
* Sometimes the very investor hesitancy around founders who are “too old” becomes a filter; if you can get past that bias, your conviction and execution shine brighter.
So yes: there’s no perfect founder. But count me in as someone testifying that there is power, clarity, and brilliance that come with founding (or serial-founding) later in life, especially when combined with the perspective to recognize both the genius and the limits of youth.
Cheers for this + looking forward to more of your essays.
Thanks Ken - I really appreciate your comment and the experience you've shared.
Thanks Ben. I also think Silicon Valley has demonized lifestyle businesses, they're not deserving of the "startup" title, and unless you're 22 and eating pizza and beer for breakfast, sleeping 2 hours per night under your desk and haven't seen the light of day in 7 months, you're not worth investing in. That narrative still runs very strong, despite the data you share. Reid Hoffman is a huge offender in this narrative. I also find the bias against people with families is fascinating, even though what you have to do to work full time AND manage kids, sleep deprivation, competing schedules, etc makes people phenomenally good at time mgmt, efficiency, and prioritization.