#129: On Freedom and Ownership With Software Entrepreneur Brian Hamilton
Release Date: 01/31/2025
#141: Inside Acquire.com's Process for Selling Sub-$5M SaaS Companies - Andrew Gazdecki
Practical Founders Podcast
Andrew Gazdecki is the founder and CEO of , a marketplace of buyers and sellers of smaller, profitable SaaS products with revenues between $100,000 and $5,000,000. Andrew sold his own software company and learned how little support and information was available to sell a software product for under $5-10 million in deal size. Acquire.com has helped over 2000 entrepreneurs sell their software products for a combined value of more than $500 million. Acquire offers additional support to help founders package, promote, negotiate, and close their transactions. Potential buyers are vetted for...
info_outline
#140: The Anti-Silicon Valley Playbook: How Genius Monkey Built a $100M Ad Tech Business on Their Own Terms - Seth Hassell and Clint Ethington
Practical Founders Podcast
Seth Hassell and Clint Ethington are the co-founders of Genius Monkey, a programmatic ad tech platform with proven targeting, tracking, and attribution for optimized results. Seth and Clint were childhood friends who worked on many business ventures before launching Genius Monkey in 2009, leveraging their experience in digital ad technologies. Genius Monkey grew steadily as a bootstrapped company, with the founders and team working hard for years to improve their platform, prove results to clients, recruit agencies, and grow their team. Most ad tech peers took VC funding and are no...
info_outline
#139: Bootstrapped Founder is Getting Ready for the AI Wave at $20M ARR - Shalin Jain
Practical Founders Podcast
Shalin Jain is the founder and CEO of HappyFox, a successful bootstrapped company that provides modern help desk management software for customer service, support, and IT management organizations. Shalin and his small team in India built many successful products from 2000-2010, then focused on HappyFox and moved to the US in 2011. is a mid-market product that sells across industries and departments with an efficient product-led growth (PLG) approach. The product has matured with successful add-on products for live chat, AI support, business intelligence, and workflows. The company has over...
info_outline
#138: Achieved Strategic Acquisition Just 2 Years After Launch - Brian Kesselman
Practical Founders Podcast
Brian Kesselman is cofounder and now CRO of , a compliance management and workflow software for financial services firms. Brian was a lawyer for major financial services companies who helped manage internal compliance in this highly regulated industry. He took a job selling compliance software and broke sales records before starting Skematic with a coworker and launching in September 2022. Skematic grew quickly by solving an acute problem for lawyers and compliance execs just like him in his industry. The company became profitable quickly as Brian focused on outbound selling with cold calls...
info_outline
#137: Her Amazing Story of 0-$30M ARR with No Outside Funding - Rebecca Shostak
Practical Founders Podcast
Rebecca Shostak is co-founder and chief brand officer of , the popular email marketing software for small businesses that care about beautiful branded emails. After prototyping the product and validating the problem, they launched in 2019 with a viral explosion that still powers their bootstrapped growth. Six years later, Flodesk has over $30M in annual recurring revenues with 75 employees and over 100,000 paid customers. They have been profitable since the second week after launch, driven by great product design, the email footer “viral loop,” and referrals from customers and...
info_outline
#136: Practical Founder Has Big Exit and Un-Retires to Build 2nd SaaS Success - Brian Dosal
Practical Founders Podcast
Brian Dosal was the founder and CEO of BrightGauge, a software company he bootstrapped and grew to almost $10M ARR with his brother before successfully selling the company in 2019. BrightGauge was a business analytics and dashboard for key metrics for the Managed Service Provider (MSP) industry. After his intense 9-year journey at BrightGauge, Brian “retired” to spend more time with his growing family. He enjoyed his free time but eventually returned to the software startup game with his second company, Strety. is a fast-growing SaaS business with a popular...
info_outline
#135: Vertical SaaS Investor Shares Proven Paths to Scale Up Big – Dave Yuan
Practical Founders Podcast
Dave Yuan is the founder of , an active growth equity investor focusing on vertical SaaS companies with outsized advantages that can become “control points” in their markets and grow very big. Dave and Tidemark have invested in successful companies like Toast, ServiceTitan, Karbon and Dutchie. In this episode, Dave shares some of the most useful strategic growth frameworks for vertical SaaS companies to grow through winning market share, expanding with additional products, and even extending through an industry ecosystem serving new markets. We also talk about the...
info_outline
#134: When It’s Time to Close: Helping Founders Shut Down Right – Dori Yona
Practical Founders Podcast
Dori Yona is co-founder and CEO of SimpleClosure, a technology- and people-powered company that helps founders wind down and dissolve a startup or business that is no longer viable. Shutting down a business can be complicated, costly, and risky for founders. SimpleClosure manages the unique processes with automation and expert support. has helped tech startup founders wind down over 500 startups, businesses that closed or have gone through a sale of assets. It manages the important steps of a winddown, including legal, regulatory, employees, investors, intellectual property,...
info_outline
#133: Bootstrapper Sells School Fundraising Platform to PE Investors - Howard Gottlieb
Practical Founders Podcast
Howard Gottlieb started in 2012 as a reading-based fundraising platform that helped students raise money while boosting education. Their easy platform and simple fundraising approach created amazing results. The Read-a-Thon business grew steadily and profitably without any outside funding. Read-A-Thon helped over 4000 schools and students raise over $30 million in donations. Their platform has tracked over 30 billion reading minutes by students who have used it to earn donations. Read-A-Thon was successfully acquired by private equity investors...
info_outline
#132: Bootstrapper Serving Private Equity Firms Acquired by PE-Backed Strategic – Richard Change
Practical Founders Podcast
Richard Change is co-founder and CEO of , the provider of FirmView software. FirmView® is the leading carry and compensation management platform for private equity investors to manage their internal compensation from fees and carried interest. Richard was a senior architect for a large private equity firm when he discovered this complex problem that was being managed on spreadsheets. He left to start PFA Solutions and bootstrapped the development of FirmView with consulting revenue. From inception, through growth and ultimately acquisition, Richard never took any outside funding....
info_outlineBrian 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.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.