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

In this episode, Matthew Steinbrecher, VP, Revenue at Reach shares insights into the intricacies of the merchant of record model, discussing common misconceptions and the inherent value it provides, particularly in cross-border transactions. The conversation also delves into the dynamic payments ecosystem, highlighting the importance of partnerships, how to identify and nurture effective collaborations, and the evolving nature of sales strategies in a competitive market. Matthew emphasizes the critical need for product market fit, listening to customer feedback, and the significance of focusing on scalable, high-value partnerships.

Tom Voaden, VP Commercial at Bridge (formerly Visa), discusses leading sales and partnerships at a high-growth fintech.

Listen and watch the full episode on Spotify & You Tube

Key Topics:

• The reality of 4x team growth - balancing startup speed with process

• Building enterprise partnerships vs. traditional networking

• Maintaining culture through rapid hiring

• AI in payments - opportunities and risks

Notable Quotes:

"Culture isn't ping pong tables - it's letting your junior engineer challenge the CEO's assumptions."

"We had to play chess with our growth. Each hire, each customer changed our trajectory."

Background:

Bridge helps enterprises modernize payments infrastructure. Under Tom's leadership, they've shifted from broad market approach to focused enterprise partnerships.

Tech Focus:

Bridge cautiously explores AI for payment optimization while prioritizing transaction accuracy and security.

Leadership Lessons:

Success came from empowering all levels to shape company direction, not top-down decisions.

Links:

https://www.linkedin.com/in/tomvoaden/

http://www.br-dge.to/

00:00 Introduction and Guest Welcome

00:39 Tom Voden's Background and Role at Bridge

01:10 Challenges and Growth at Bridge

03:06 Maintaining Company Culture

10:17 Balancing Growth and Sustainability

13:20 Customer Focus and Market Strategy

21:59 Visa Experience and Industry Insights

29:59 Commercial Strategy and Partnerships at Bridge

40:30 AI in Payments and Future Prospects

43:10 Conclusion and Farewell

In this episode, Karl Lillrud shares his insights on how advancements in AI, automation, and no-code tools have transformed the startup landscape, making bootstrapping more accessible than ever. He discusses the importance of prudent capital use, prioritizing simplicity, and building products that solve real customer problems.

Karl emphasizes the value of learning quickly, iterating based on feedback, and avoiding feature overload. He explains how AI is a game-changer for startups, enabling faster operations, smarter decision-making, and reduced costs. From autonomous AI agents to breakthroughs in healthcare, Karl highlights the vast potential of AI to revolutionize industries.

The episode also explores funding strategies, advocating for delayed VC funding until startups have validated their ideas and built a strong foundation. Karl discusses alternatives like private debt, revenue-based financing, and crowdfunding, offering insights into navigating the high-pressure environment of venture capital.

Gain actionable advice on leveraging AI tools, engaging early adopters, and maintaining flexibility while scaling. With a focus on strategic growth and innovation, Karl provides a roadmap for founders to build smarter, more resilient startups.

Ozan Ozark is a serial entrepreneur who founded and successfully exited Norway's most popular social media platform before going onto found a portfolio of 5 fintech companies, including OpenPayd, without any external funding. In this first episode of the Fintech Ventures Podcast, he explores his remarkable journey with your host Martin and discusses important topics along the way.

00:00 Introduction to the Fintech Ventures Podcast

00:56 Ozan Ozark's Early Life and Tech Beginnings

02:20 The Rise of Social Media in Norway

04:53 Transition to FinTech and Founding OpenPaid

06:49 Understanding Embedded Financial Services

11:40 Challenges and Opportunities in the FinTech Ecosystem

16:41 Founding European Merchant Bank

18:26 Exploring Eurotrader and the Future of Cross-Border Payments

22:01 Introduction to BitBase: A Web3 Business

22:47 Managing a Diverse Portfolio

23:17 Segregation and Culture in Business

25:26 Involvement and Strategy Across Companies

26:28 Criteria for Selecting Ventures

27:33 The Role of Regulation in Business

28:35 Financing and Market Timing

31:06 Views on FinTech Regulation

33:55 Open Banking: Current State and Future

37:13 Advice for Aspiring FinTech Founders

40:49 Conclusion and Contact Information