Flying With Founders

Flying With Founders

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

10/28/2026

Who are you when the sport ends? Emily Breunig built Athletepreneur around a question nobody prepares athletes for. The playbook for the sport itself is airtight. The playbook for what comes after almost never exists.

10/27/2026

6,000 pounds to 125,000 pounds. Megan Alexander's first rule for growing Carter's Compost: change nothing. She spent her first season just doing the work exactly as it already existed, learning the business from the inside before she touched anything.

10/26/2026

Carter's Compost was started by an actual kid, on a bike, with a crew of friends he called "bucket slingers," composting food scraps around Traverse City for ten years. Megan Alexander runs it now, but the company's DNA was set before it was ever really a company.

10/23/2026

Chris Gustafson's secret to staying sharp isn't more discipline. It's having something on the calendar that isn't work — a half-day trip, a flight booked for February. Sounds small. Isn't. The grind gets survivable by having a reason to look up from it, not by pushing harder through it.

10/22/2026

Julie Holton spent 12 years as a TV executive producer before she walked away, with no plan waiting on the other side. She wasn't chasing a startup idea. She was chasing her life back. Her honest twist: she doesn't actually work less now, it's just work she chose instead of work that chose her.

10/21/2026

A steady paycheck feels like control. It usually isn't. You don't see the balance sheet, the board meetings, the quiet decisions that eventually show up as a layoff email. Julie Holton on the trade nobody talks about when they take the "safe" job.

10/20/2026

Pilots run a check before every flight. Reuben runs the same kind of check on founders — borrowed straight from real aviation and turned into a five-part self-awareness tool: physical, intellectual, relational, emotional, spiritual. Not a mood ring. A pre-flight checklist for the parts of running a company that don't show up on a P&L.

10/19/2026

How Reuben got into flying!

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.

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