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Startup DadAdam Fishman (author of a top business newsletter on Substack with 11K subscribers) interviews executives, entrepreneurs, and company leaders in technology companies who are also fathers. Author: Adam Fishman
Adam Fishman (author of a top business newsletter on Substack with 11K subscribers) interviews executives, entrepreneurs, and company leaders in technology companies who are also fathers. They discuss the tough aspects of work, parenting, family, the mistakes made and lessons learned along the way. All episodes at www.startupdadpod.com. Language: en Genres: Kids & Family, Parenting, Technology Contact email: Get it Feed URL: Get it iTunes ID: Get it |
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Either the Kids Suck or the Parents Suck | Caleb Avery (Dad of 3, Founder of Tilled)
Thursday, 16 April, 2026
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 AveryLinkedIn: https://www.linkedin.com/in/caleb-avery/ Where to find Adam FishmanFishmanAF Newsletter: www.FishmanAFNewsletter.com LinkedIn: https://www.linkedin.com/in/adamjfishman/ Instagram: https://www.instagram.com/startupdadpod/ X: https://x.com/fishmanafIn this episode, we cover:(00:00) Welcoming Caleb Avery, Founder/CEO of Tilled(02:50) Starting Tilled while raising young kids(05:12) The time and energy trade-offs of startups and parenting(07:53) Paternity leave regrets after his first child(10:53) How COVID unexpectedly gave him the leave he wanted(14:19) Why it is so hard to make parent friends(17:43) What fatherhood taught Caleb about nature versus nurture(19:19) Becoming an accidental T-ball coach(28:03) His advice to founders thinking about having kids(30:23) How becoming a dad made him a better CEO(32:22) Why bedtime is Caleb’s top parenting priority(35:04) Family time boundaries and being fully present(37:41) Redefining work-life balance as a startup dad(40:36) Kids, iPads, and setting screen time boundaries(48:15) Lightning round: Snoo wins, dishwasher rules, and a toy assembly nightmareResources From This Episode:Tilled: https://www.tilled.com/ The Snoo: https://www.happiestbaby.com/products/snoo-smart-bassinet The Sandlot (Film): https://www.imdb.com/title/tt0108037/ Diehard (Film): https://www.imdb.com/title/tt0095016/ Golf Cart for Kids: https://a.co/d/0hVZwx85 iPad: https://www.apple.com/ph/ipad/ Lincoln Navigator (Car): https://www.lincoln.com/luxury-suvs/navigator/ —Support Startup DadFor sponsorship inquiries, email: podcast@fishmana.com.For Startup Dad Merch: www.startupdadshop.com
