Caleb Avery
Founder and CEO of Tilled, an entrepreneur who started his first company at 19 and has built Tilled while raising three children, sharing insights on startups and fatherhood.
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Apr 16, 2026 • 1h 3min
Either the Kids Suck or the Parents Suck | Caleb Avery (Dad of 3, Founder of Tilled)
Caleb Avery, founder and CEO of Tilled who started his first company at 19 and raises three kids, shares candid stories about building a startup while parenting. He talks trade-offs of time and energy, paternity leave regrets and course corrections, why bedtime became a non-negotiable, the struggle of making parent friends, coaching T‑ball, screen time rules, and choosing boundaries over balance.
