Accidental T‑Ball Coach and Lessons Learned

Caleb describes becoming head coach, focusing on fun over competition and managing chaotic practices.

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Caleb Avery is the Founder and CEO of Tilled. He started his first company at 19 and has spent the last seven years building Tilled while raising three kids with his wife, Kelsey.

In this episode, Caleb shares what it really looks like to build a startup and a family at the same time. We talk about the trade-offs founders need to be honest about, his regrets around paternity leave with his first child, and why bedtime became his most important non-negotiable as a dad.

We also get into the little-discussed challenge of making parent friends, what coaching his son’s T-ball team taught him, how he and his wife think about screen time and technology, and why he believes work-life balance is less useful than clear boundaries. We discussed:

Starting a company while raising young kids: How Caleb thought about the trade-offs of building a startup and growing a family at the same time.
Paternity leave regrets and what changed: Why Caleb still thinks about working from the hospital after his first child was born, and what changed with his second child.
Why bedtime is his top parenting priority: How Caleb built his schedule around being home for bedtime and why it became his most important non-negotiable as a dad.
Boundaries over balance: Why Caleb does not chase perfect work-life balance and focuses on a few clear non-negotiables instead.
The little-discussed challenge of making parent friends: Why it is so hard to find families where both the kids and the parents actually click.
Honest advice for founders thinking about kids: Caleb explains why aspiring startup parents need to be brutally honest about the trade-offs before signing up for both.

Where to find Caleb Avery