Practical Founders Podcast

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

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.

01:06:34

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Episode guests

Brian Hamilton

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Quick takeaways

Brian Hamilton emphasizes entrepreneurship as a transformative journey that grants individuals freedom and control over their lives.

Hamilton advocates for a bootstrapping approach, highlighting how limited resources can foster creativity and self-sustainability without heavy reliance on funding.

Through his nonprofit, Inmates to Entrepreneurs, Hamilton empowers individuals with criminal backgrounds, showcasing entrepreneurship as a pathway to economic reintegration and opportunity.

Deep dives

The Journey of Entrepreneurship

Brian Hamilton emphasizes the transformative power of entrepreneurship as a means of freedom and control over one's destiny. He recounts his journey from starting SageWorks in a small incubator to growing it into a profitable company with hundreds of employees. By leveraging innovative technology to simplify complex financial data, he empowered small business owners, showcasing the impact of practical entrepreneurship. Hamilton highlights that the journey involves challenges and requires perseverance, ultimately leading to personal satisfaction and a sense of accomplishment.

Intro

2min

The Climate of Entrepreneurship: From the North to the South

2min

The Entrepreneurial Journey: Building and Selling SageWorks

23min

Navigating Entrepreneurship: Misfits to CEOs

12min

The Entrepreneurial Journey: Challenges and Reflections

17min

Understanding Entrepreneurship and Injustice in Prisons

2min

The Paradox of Entrepreneurship and Wealth

6min

Momentum and Growth: Keys to Entrepreneurial Success

3min

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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Practical Founders Podcast

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

Episode guests

Podcast summary created with Snipd AI

Quick takeaways

Deep dives

The Journey of Entrepreneurship

The Importance of Bootstrapping

Navigating the Challenges of Growth

Inmates to Entrepreneurs Initiative

The Paradox of Success

Remember Everything You Learn from Podcasts