Flying With Founders

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Flying With Founders Authentic and fun conversations while flying with founders, entrepreneurs, and investors.

10/16/2026

Monsters Inc. taught us a killer GTM lesson and we probably never realized it until now...

The monster wasn't winning by being the scariest — he was winning by having the best distribution, more doors, more scale.

10/15/2026

We're helping founders connect the dots of all the eight things you need to build into your company so it's attractive to buyers. But then we're also talking about what are the eight things we need to build into YOU to make sure you can do that. It's incomplete with just one or the other.

10/14/2026

Founder wellness isn't just a soft topic anymore. Some investors are asking about it directly in diligence now — does the founder take care of themselves, or is the business the only thing they're focused on. Not every investor asks. The ones who do are asking earlier every year.

10/13/2026

Not a therapist. Not a co-founder. A specific set of friends whose only job is to listen to a voice memo and text back "got it, good processing." No advice, no fix needed — just proof that saying it out loud to someone landed. Small habit, does a lot of quiet work.

10/12/2026

Here's how Reuben catches his own burnout before it catches him: "If I'm going to have a week or two of no achievements, I notice I start to feel down. So maybe I've got to go get to the gym, or play some pickleball, or get a quick win." Not a framework. Just a founder who's learned his own pattern.

10/09/2026

Reuben uses the Enneagram with founders on retreats, and he's got a theory for why it actually lands: "First, they have to care. And once they've experienced some burnout, they do care. And when they hear that investors like us care too, it's okay to care." It's not the assessment doing the work. It's the permission.

10/08/2026

A VC once said this to Reuben about founder health...

10/07/2026

"The only thing that kills portfolio return that I never see coming is founder burnout." A VC said that, word for word, relayed here by Jeff Baxter. Not a bad market. Not a competitor. The thing that actually blindsides a fund is the thing founders are least likely to bring up on a call.

10/06/2026

Emily Breunig's method for finding your next chapter starts somewhere nobody expects: your own bathroom cabinet, the stuff you already recommend to friends for free. Not a personality test. The stuff you recommend unprompted, because you actually believe in it, is usually the clearest signal of where your next thing lives.

10/06/2026

63% of the time, a startup fails because of people problems, not the business itself. Co-founder conflict. Burnout. Depression. Broken relationships. That's the actual list behind probably the largest study of failed founders ever done — and it's not about product-market fit.

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