Caleb Avery, CEO and Founder of Tilled, After 18 Months of Bootstrapped Growth, Has Gone on to Raise Over $40M and Become a Category Leader

In this episode of Bootstrap Ventures - The Scalepoint Podcast, I interview Caleb Avery, CEO and founder of Tilled—a category leader in the PayFac-as-a-Service space. Caleb shares insights on Tilled’s phenomenal growth in 2024, achieving over 500% year-over-year growth, and highlights the company’s strategic move into enterprise. Caleb recounts his journey from bootstrapping the company in 2019 to securing venture capital and scaling significantly. He discusses the challenges and advantages of bootstrapping in the early stages, their approach to securing funding, and the importance of customer validation. He also explains the enterprise strategy and the significance of their partnership with North in reshaping the payment processing landscape. 00:00 Introduction and Guest Welcome 00:47 Excitement for 2025 and Tilled's Growth 01:31 Industry Trends and Market Shifts 03:13 Pivoting to Support Traditional Incumbents 04:06 Founding Tilled and Early Challenges 06:04 Bootstrapping and Delaying External Funding 09:31 First Round of Venture Funding 16:04 Impact of External Funding 26:16 Enterprise Strategy and Recent Funding 35:06 Future Vision and Product Enhancement 38:46 Advice for Aspiring Entrepreneurs 41:11 Closing Remarks