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PODCAST

Practical Founders Podcast

Tune into the Practical Founders Podcast with host Greg Head for weekly in-depth interviews with founders who have built valuable software companies--without big funding.

business entrepreneurship

All Episodes

55:44

#148: These Bootstrappers Sold Modern Digital LeadGen...

Practical Founders Podcast ·

2025/06/13

Chris Erler was co-founder and COO of ComX, a sales pipeline generation for mid-market B2B companies in Germany and Europe. Chris and two other founders started the company in 2018 to conduct turnkey modern digital marketing and lead generation solutions for traditional German companies. As a tech-enabled service that combines technology, data, and people-powered solutions, ComX delivers proven results through subscription and outcome-based pricing. They grew quickly to approximately $20 million in

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01:04:44

#147: How a Philadelphia Insurance Agent Built the...

Practical Founders Podcast ·

2025/06/06

Aaron Steffey is the co-founder and co-CEO of Propeller, an online platform that enables insurance agents and brokers to issue surety bonds instantly — without the lengthy paperwork or back-and-forth typically involved in bonding. Aaron was an insurance agent, and his co-founder cousin, Chris, was a surety bond underwriter before 2019, when they set out to revolutionize the way surety bonds are bought and sold. They initially bootstrapped with a software development partner who accepted equity

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01:00:46

#146: This European SaaS Bootstrapper Raised $22M in...

Practical Founders Podcast ·

2025/05/30

Roy van den Broek is the founder and CEO of Rentman, a rental business management software platform for event and media production companies. Roy built software for his event equipment rental business in the Netherlands. He had over 100 software customers in Europe before selling his rental equipment company in 2015 to focus on growing his Rentman SaaS company. Rentman grew slowly and profitably as word of mouth spread in the industry and their product evolved. In 2024, after growing to nearly 100

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59:50

#145: Making Big Bold Bets with Patient Execution as...

Practical Founders Podcast ·

2025/05/23

Gopal Krishnamurthy is the founder and CEO of Lumel, which has a suite of products focused on enterprise performance management (EPM). Their apps allow users to plan, report, and analyze data using the modern native app framework vs. traditional SaaS on top of modern cloud data platforms such as Microsoft Fabric, Snowflake, Databricks, and others. Lumel’s products provide a full stack of integrated Planning, BI & data apps on the customers' data platforms. He grew his enterprise services company,

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58:20

#144: From Founder-Led Sales to Scalable Go-To-Market...

Practical Founders Podcast ·

2025/05/16

Phil Stern is the operating principal of Mainsail Partners, a growth equity firm that invests in bootstrapped vertical SaaS companies. Mainsail offers deep operating support to the leaders in their portfolio companies to help them grow more efficiently. Phil leads the GTM operations team, helping their founders scale sales, marketing, and success teams. Phil was an experienced SaaS sales leader at several companies before joining Mainsail to focus on helping their portfolio companies scale up to

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01:04:53

#143: From Professional Services to a $30M SaaS...

Practical Founders Podcast ·

2025/05/09

Sean Hoban was co-founder and former CEO of Kimble Applications, a leading professional services automation (PSA) software for organizations to manage their professional services business's entire operational and financial lifecycle. Sean and his co-founders had already started, grown, and sold a pro services organization before creating a PSA product and building a SaaS business. With a little funding from the founders and a few angel investors, Kimble started efficiently and grew steadily,

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58:37

#142: Why This 3x SaaS Founder Couldn't Stay Retired...

Practical Founders Podcast ·

2025/05/02

Josh LaSov is the founder and former CEO of Satori Reporting, an advanced reporting and business intelligence (BI) solution for mid-market businesses that use NetSuite financial software. Satori provided pre-built reports and dashboards, a tailored data warehouse, and detailed data models that leveraged the popular Power BI software. Josh launched Satori, his second NetSuite solution, in 2019 and grew quickly in the NetSuite ecosystem, with a savvy team and no outside funding. Satori was sold it to

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55:39

#141: Inside Acquire.com's Process for Selling...

Practical Founders Podcast ·

2025/04/25

Andrew Gazdecki is the founder and CEO of Acquire.com, 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

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01:04:34

#140: The Anti-Silicon Valley Playbook: How Genius...

Practical Founders Podcast ·

2025/04/18

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,

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01:07:35

#139: Bootstrapped Founder is Getting Ready for the...

Practical Founders Podcast ·

2025/04/11

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. HappyFox 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

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01:00:15

#138: Achieved Strategic Acquisition Just 2 Years...

Practical Founders Podcast ·

2025/04/04

Brian Kesselman is cofounder and now CRO of Skematic, 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

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01:04:57

#137: Her Amazing Story of 0-$30M ARR with No Outside...

Practical Founders Podcast ·

2025/03/28

Rebecca Shostak is co-founder and chief brand officer of Flodesk, 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

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01:11:26

#136: Practical Founder Has Big Exit and Un-Retires...

Practical Founders Podcast ·

2025/03/21

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

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55:49

#135: Vertical SaaS Investor Shares Proven Paths to...

Practical Founders Podcast ·

2025/03/14

Dave Yuan is the founder of Tidemark, 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

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44:27

#134: When It’s Time to Close: Helping Founders Shut...

Practical Founders Podcast ·

2025/03/07

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. SimpleClosure 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

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58:47

#133: Bootstrapper Sells School Fundraising Platform...

Practical Founders Podcast ·

2025/02/28

Howard Gottlieb started Read-A-Thon 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.

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01:09:35

#132: Bootstrapper Serving Private Equity Firms...

Practical Founders Podcast ·

2025/02/21

Richard Change is co-founder and CEO of PFA Solutions, 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

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01:03:43

#13`: No-Code SaaS Platform Bootstrapped to 75,000...

Practical Founders Podcast ·

2025/02/14

Rachit Khator is the founder and CEO of Stackby, a no-code spreadsheet and database app builder that allows business users to create powerful spreadsheet-like applications with data links, automations, and workflows. Rachit and his team of 34 employees live in Surat, India, north of Mumbai. Stackby started when Rachit was working for a corporate venture firm in Michigan, doing repetitive manual data imports and analysis in Excel. He hired a developer to build a better tool and started to sell

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01:07:58

#130: Profitable Product-Led Growth to $30 Million...

Practical Founders Podcast ·

2025/02/07

Joe Hyrkin is the former CEO of Issuu, a content publishing platform for interactive marketing content. Issuu allows you to easily publish printable and PDF materials in various formats to websites and social media. It’s a global product-led success story with millions of customers and a successful and sustainable business. Issuu was started by four Danish founders before the company was moved to Silicon Valley in 2013 when Joe was hired as the CEO. Joe ran the company for almost 12 years, growing

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01:06:34

#129: On Freedom and Ownership With Software...

Practical Founders Podcast ·

2025/01/31

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

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167 results

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