Caleb Avery, Founder & CEO of Tilled

“Don't sleep on culture. The culture you create is hard to measure but if you can create that healthy culture within the business you'd be surprised at how effective the business can be.

Caleb Avery is the Founder & CEO of Tilled, a PayFac-as-a-Service company helping software companies monetize their payments. Tilled raised a Series of A of $11M in May of 2021 and raised another $11M in the beginning of 2022 as they quadrupled their team and tripled their valuation in just over 6 months.


Key Takeaways:

  1. Social Media Matters: In the beginning stages of the company, nearly 100% of the lead generation came through Caleb's social media following on LinkedIn. Even with their rapid growth, 45% - 50% of their lead gen still comes through his social media.

  2. Preparation: Tilled had been preparing for over a year on their go-to-market strategies so that when the time came, they were able to execute and 3x their valuation in six months.

  3. Priorities: "What you define as important in your life determines how you set-up your calendar and spend your time." Caleb makes sure to prioritize what's most important first - Dropping off kids at school, going to a ballet recital, etc., to ensure life doesn't get out of balance on what really matters.

Topics Covered:

  • Founding Story

  • How the macro environment can be a competitive advantage for Tilled 5:10

  • Why Tilled raised a Series A extension rather than a Series B 7:08

  • How Tilled quadrupled the team and 3x'd valuation in just over 6 months 9:00

  • Caleb's social media strategy 11:25

  • How should a founder get started with social media 16:20

  • What were the early days of the company like when it was just 5 people 19:25

  • How has Tilled been so successful in retaining people 20:54

  • What is work life balance at a startup 23:23

  • Where does Caleb spend his time as a CEO 25:40

  • Productivity hacks 28:26

  • Best advice for others 30:20


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