May 14, 2025
4
min. Reading Time

The Loneliest Ambition

The Loneliest Ambition

The Loneliest Ambition

Mike Shai

Founder, Founding Fathers Club

For most of my adult life, I thought building something meaningful, a company, a product, a vision, would feel like enough.

And in some ways, it has. I’ve had late nights where I felt unstoppable, brainstorm sessions that left me buzzing, and quiet moments where I realized, "We actually made this real."

But here’s the part nobody tells you: even when it is working, it can still feel incredibly lonely.

I co-founded a startup that I poured everything into. I had a small team I loved, product-market momentum, and a calendar that was somehow always full. I was also navigating being a dad to three kids and trying to show up at home with the same energy I brought to product calls.

And yet, despite doing "the thing" – the dream, the hustle, the build – I found myself realizing that I didn’t really feel known. Not deeply. Not consistently. Not in the way you crave when the adrenaline wears off and you’re left with silence between meetings.

Remote work didn’t help. I was working from my home office in a hoodie while Slack pings and Zoom links simulated connection. There were no water cooler chats, no lunch break decompress sessions, no spontaneous "dude, I feel that too" moments. And outside of work, making new friends as an adult dad founder? Good luck.

The startup world rewards output. Parenting rewards presence. But very few things in my life were rewarding connection in a way that filled me back up.

What I started to realize was that the problem wasn’t what I was building. It was that I was building it alone.

Not without people, but without true peers. Without people who got the weird pressure of raising kids while chasing funding. Without others who knew how it felt to want to provide stability and take a wild bet at the same time. Without friends who could hold the messy middle with me.

That realization is what led to the earliest seed of what became Founding Fathers Club.

It wasn't about mentorship or networking. It was about having people who could sit next to me on the bleachers, have a beer after bedtime, and ask how it actually felt to try and build something while staying connected at home. It was about not needing to translate every part of myself depending on who I was with.

Because the truth is: the work is important. The family is sacred. But the friendships — the deep, real, ride-or-die, "I see you" friendships — those are what make all of it sustainable.

You can build something great and still feel like something's missing. And you're not broken for feeling that. You're just human.

The loneliest ambition is the one pursued in silence.

But it doesn't have to be that way.

Questions?

Whether you're a curious dad, a potential collaborator, or someone who stumbled here and thinks this sounds awesome, we're glad you're here.

Drop us a note below and we’ll get back to you faster than a toddler can spill a full cup of juice.

© 2025 Founding Fathers Club. All rights reserved

Questions?

Whether you're a curious dad, a potential collaborator, or someone who stumbled here and thinks this sounds awesome, we're glad you're here.

Drop us a note below and we’ll get back to you faster than a toddler can spill a full cup of juice.

© 2025 Founding Fathers Club. All rights reserved

Questions?

Whether you're a curious dad, a potential collaborator, or someone who stumbled here and thinks this sounds awesome, we're glad you're here.

Drop us a note below and we’ll get back to you faster than a toddler can spill a full cup of juice.

© 2025 Founding Fathers Club. All rights reserved