Why You Must Love the Problem You Solve - Caleb Avery - S6 - E11 episode artwork

EPISODE · May 13, 2026 · 16 MIN

Why You Must Love the Problem You Solve - Caleb Avery - S6 - E11

from A Founder's Life · host Leo Gestetner

This episode of A Founder’s Life is brought to you by Thankz, helping founders scale with reliable remote talent. Get $1,000 off your first month by emailing [email protected] with the subject line Founder’s Life.🌐 Follow A Founder’s Life • YouTube:   @AFoundersLife   • LinkedIn:  https://www.linkedin.com/company/a-founder-s-life-podcast/ • Instagram: @afounderslife   • Spotify & Apple Podcast: https://linktr.ee/afounderslife👤 Connect with Today’s Guest – Caleb AveryWebsite: https://tilled.comLinkedIn: https://www.linkedin.com/in/caleb-avery/Building a successful startup isn’t about finding the perfect idea—it’s about choosing a problem you’re passionate enough to solve for the next decade.In this episode of A Founder’s Life, Leo Gestetner sits down with Caleb Avery, Founder and CEO of Tilled, to discuss his entrepreneurial journey from selling payment solutions door-to-door at 19 years old to building one of the leading embedded payments platforms in the fintech industry.Caleb shares how years of consulting software companies revealed a common problem: businesses were leaving millions of dollars in payment revenue on the table. That insight led him to found Tilled, a company pioneering the concept of “PayFac as a Service” and helping software platforms monetize embedded payments more effectively.But this conversation goes beyond fintech.Caleb opens up about launching a startup during the uncertainty of COVID-19 while raising two young children, the importance of having a supportive family, and why entrepreneurship is less about balance and more about being intentional with your time.Throughout the conversation, we explore entrepreneurship, founder mindset, business leadership, resilience, family, and what it really takes to build a company that lasts.Whether you’re considering launching your first business or scaling an existing startup, Caleb shares practical lessons every founder can apply.In this episode you’ll learn:• Why solving the right problem matters more than chasing trends • How embedded payments create new revenue opportunities • Why startups require long-term commitment and patience • The importance of being intentional with your time as a founder • How to balance entrepreneurship with raising a family • Why passion is essential for long-term business success • The value of staying focused during uncertain times • How COVID shaped both Caleb’s business and personal life • Why founders should build businesses they’re excited to run for the next ten yearsCaleb also shares how his wife encouraged him to continue building Tilled during one of the most uncertain periods of his life, why being present with his children matters more than chasing the idea of perfect balance, and how consistency compounds into entrepreneurial success.If you enjoy conversations about entrepreneurship, founder mindset, fintech, business leadership, startup journeys, business growth, and personal development, you’ll enjoy this episode.LinkedInlinkedin.com/in/leogestetnerWebsiteleogestetner.com/leoSubscribe Now!youtube.com/@afounderslife?sub_confirmation=1

Episode metadata supplied by the publisher feed · Published May 13, 2026

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This episode of A Founder’s Life is brought to you by Thankz, helping founders scale with reliable remote talent. Get $1,000 off your first month by emailing [email protected] with the subject line Founder’s Life. 🌐 Follow A Founder’s Life • YouTube: @AFoundersLife • LinkedIn: https://www.linkedin.com/company/a-founder-s-life-podcast/ • Instagram: @afounderslife • Spotify & Apple Podcast: https://linktr.ee/afounderslife 👤 Connect with...

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Why You Must Love the Problem You Solve - Caleb Avery - S6 - E11

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