Flying With Founders

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

09/04/2026

A founder told me: "As soon as we hit the next milestone, I will finally slow down."

There is no as soon as.

The next round, the next hire, the next quarter. There is always another one. If you do not build health into the business now, you never will, and you burn out before you ever get to enjoy what you built.

You can grow and stay whole. We show founders how.

09/03/2026

JD Audena invests for a living at Connetic Ventures. Here is what he said about the other side of the table:

"Founders have it so hard. It is much easier to be a VC. You are trying to bring a vision to life for so long, and thinking about the exit can feel demoralizing or off-plan. But it is important."

A VC with that much respect for the founder's road is rare. Worth listening to.

09/02/2026

Steven Plappert's first startup cost him almost everything. Not just the money.

"What I gave up at that company was my physical and mental health, and almost my relationship with my wife. It all almost fell apart. And the company still failed. So it just was not worth it."

When he started Forecastr, he set his boundaries first. He was not going to work himself to the bone again.

09/01/2026

Tim Tweet thought Proper Pilots was booming when the waitlist hit 200.

Last he checked, it was 6,200.

Not all of them are decision makers at flight schools. But every one is an instructor or student who felt the same gap Tim did and wanted it fixed.

That is what real demand looks like. It finds you.

08/31/2026

The fear never fully goes away. You just stop letting it drive.

Lindsay Joseph on the quiet cost of playing it safe: the opportunities you miss because fear made the call for you.

Every founder feels it. The ones who grow feel it and move anyway.

08/28/2026

Steven Plappert's first company was a daily fantasy startup holding people's money. When it collapsed, he had to go dark for eight weeks while quietly negotiating a soft landing. He could not tell anyone what was happening.

So people assumed the worst.

He was a 24-year-old kid trying to survive it. The business was survivable. The story is a reminder of how much weight founders carry that nobody ever sees.

08/27/2026

Last year they took 89 flights.

Madhav and Tanvi were traveling every third day and completely lost sight of their health. No workouts, no breaks, always on.

This year they drew a line. Move every day. And the hardest one for a founder: it is okay not to answer that email in five seconds.

You cannot build a lasting company on an empty tank.

Healthy founders, healthy exits.
→ flyingwithfounders.com/program"

08/26/2026

"The challenge never goes away. That can be exciting, or it can be daunting."

Justin Scott on the choice every founder makes over and over. The problems keep coming and they get bigger. You can see a threat, or you can see a challenge worth chasing.

That reframe, plus a handful of small wins, is what keeps you in the game.

08/25/2026

JD Audena's firm built an AI platform to evaluate founders no matter where they are. Why? Because great founders are not only in the Bay Area.

"There are amazing founders in Kentucky, in Kansas, in Michigan, and everywhere. If you are not in the Bay Area or New York or Austin, it is hard to get noticed by capital. Every early stage investor is making a gut instinct on whether this is the team. We are trying to quantify that gut instinct."

08/24/2026

When Kalob Hagan started Luigi Solutions in 2020, he did the work for free. On purpose. For three years.

The bet: stack up enough testimonials and get good enough that charging later becomes the easy part.

"That three years was brutal. I was working a full-time job and doing free work just to get good at it."

Every overnight success skips this chapter. The unglamorous years are where the company actually gets built.

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