#129: On Freedom and Ownership With Software Entrepreneur Brian Hamilton

8 snips

Jan 31, 2025

Brian Hamilton, a fintech pioneer and founder of Sageworks, shares his compelling entrepreneurial journey. He discusses the evolution of Sageworks from struggles to success, emphasizing the importance of bootstrapping and innovation. Hamilton highlights the impact of location on entrepreneurial spirit, contrasting Chicago and North Carolina. He also advocates for entrepreneurship as a pathway for ex-inmates, urging for systemic changes to support reintegration. The conversation delves into the emotional challenges of business ownership and the balance between financial success and personal fulfillment.

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ANECDOTE

Humble Beginnings

SageWorks began in a small incubator office in Research Triangle Park, North Carolina.
It grew organically to hundreds of employees and remained cash flow positive for 10 years.

ADVICE

Freedom and Funding

Bootstrap your business to maintain control and learn from mistakes.
Avoid institutional funding unless absolutely necessary for scaling.

ANECDOTE

SageWorks' Genesis

Brian Hamilton's idea for SageWorks came from teaching financial courses and realizing the need for automation.
A conversation with a PhD who struggled to understand financial numbers solidified the concept.

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Brian Hamilton is one of America’s most successful entrepreneurs and a leading expert on entrepreneurship. Today, Hamilton serves as chairman of software company LiveSwitch. He is known for his pioneering work in fintech, his advocacy for small businesses, and his commitment to criminal justice reform.

As the founder of Sageworks (now Abrigo), America’s first fintech company, Hamilton developed technology that translates complex financial data, empowering millions of small business owners.

Sageworks struggled and grew slowly for 10 years before pivoting to serve local banks and credit unions with financial tools to assess the creditworthiness of their small business loans. The practical SaaS company grew steadily and very profitably to more than 400 employees when it was sold in 2018.

Through Inmates to Entrepreneurs and the Brian Hamilton Foundation, he encourages entrepreneurship as a means to economic opportunity. Hamilton’s work has been showcased by major media outlets like CNBC and Good Morning America, and he starred in ABC’s Free Enterprise TV series, an award-winning show based on Inmates to Entrepreneurs.

Quote from Brian Hamilton, founder and former CEO of Sageworks

"Being the founder of a tech company is like this: You're in a tunnel, it's dark, you're on your hands and knees, you're going through that tunnel, you're groping your way through, keep moving forward.

"I know it sounds like such a BS, but we've all been there. I'm telling you, that is the picture: you're in this huge sewer tunnel, it's dark. You just gotta keep moving. Just keep chipping away. You do that, and you will get momentum somehow.

"It's like compound interest. You start with a dollar and how does it turn into $10? You build momentum a little at a time. I've got to listen every day. I'm knocking off making the product better. You develop the physical property of compound interest and things will get better."

Links

Podcast Sponsor - Cypress Growth Capital

This week’s podcast is sponsored by my friends at Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast. Message Cliff Sentell at Cypress to have an open discussion about your options.

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