Greg Head

Practical Founders Podcast

Business EN ↓ 203 episodes

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.

Author

Greg Head

Category

Business

Podcast website

practicalfounders.com

Latest episode

Jul 10, 2026

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Episodes

#154: 2nd-Generation CEO Modernizes Mom's Legacy Software Business - Brian Forbis 25.07.2025

Brian Forbis is the CEO and president of Blood Bank Computer Systems, Inc. (BBCS), a business his mother created in the 1980s to serve the non-profit blood bank industry in the US. Brian started in sales, then transitioned to run development, and assumed the role of CEO in 2019 when he bought the company.  BBCS rebuilt its entire mission-critical ERP software as a modern cloud solution over the la...

#153: Bootstrapper Killed His First Company to Scale Up Bigger - Chris Brisson 18.07.2025

Chris Brisson is the CEO and co-founder of Salesmsg, a conversational two-way texting platform that enables businesses to engage with their customers through opt-in SMS. When his first software company stalled, he shut it down and developed the Salesmsg product for a different SMS use case that served his previous customers.  Salesmsg now provides secure SMS texting across all departments in the c...

#152: Practical SaaS CEO Stays On After 100% Cash Sale - Tracy Larson 11.07.2025

Tracy Larson is President and CEO of WeSuite, a vertical sales automation platform designed for larger integrators who sell complete security systems for commercial and residential real estate. Tracy and the cofounders were in the security systems business before launching a sales software company for this market in 2008.  WeSuite is now a comprehensive solution that addresses the complex industry...

#151: Facial Recognition SaaS for Casinos to Almost $10M in Revenue – Henry Valentino 04.07.2025

Henry Valentino is the founder and CEO of EConnect , a leading provider of facial recognition software for casinos and stadiums, ensuring venue security and compliance. He founded EConnect in 2009 and pivoted several times before focusing on a security platform utilizing AI for casinos during the COVID-19 pandemic. The Econnect platform offers facial recognition surveillance software that integrat...

#150: Grew an Unsexy Small Software Biz Into a SaaS Powerhouse - Josh Turley 27.06.2025

Josh Turley is CEO of RTA Fleet Management , a fleet management software company that his grandfather started in the 1980's and ran as a small family business for decades. Then Josh's father ran the business until 2015, never growing this slow, old-school business past $2 million in revenues. Josh had worked in the business before, but in 2016, Josh bought the business, to over as CEO and slowly b...

#149: How Partner-Led Sales Built A $7M Bootstrap SaaS Business - Sameer Narkar 20.06.2025

Sameer Narkar is the founder and CEO of Konnect Insights , a global SaaS company based in Mumbai that provides an omnichannel customer experience platform to consumer brands in 100 countries. Sameer created Konnect Insights in 2015 to help customer service teams respond to customers who mention their brands on social media. The product and company have expanded from a slow start working through ma...

#148: These Bootstrappers Sold Modern Digital LeadGen to Conservative German Businesses - Chris Erler 13.06.2025

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 re...

#147: How a Philadelphia Insurance Agent Built the Uber of Surety Bonds - Aaron Steffey 06.06.2025

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 b...

#146: This European SaaS Bootstrapper Raised $22M in Growth Equity Without Losing Control - Roy van den Broek 30.05.2025

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...

#145: Making Big Bold Bets with Patient Execution as a Bootstrapped Founder - Gopal Krishnamurthy 23.05.2025

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 integrat...

#144: From Founder-Led Sales to Scalable Go-To-Market in Vertical SaaS - Phil Stern 16.05.2025

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...

#143: From Professional Services to a $30M SaaS Business with a PE Acquisition - Sean Hoban 09.05.2025

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 f...

#142: Why This 3x SaaS Founder Couldn't Stay Retired to Launch His New Al Startup - Josh LaSov 02.05.2025

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...

#141: Inside Acquire.com's Process for Selling Sub-$5M SaaS Companies - Andrew Gazdecki 25.04.2025

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 sof...

#140: The Anti-Silicon Valley Playbook: How Genius Monkey Built a $100M Ad Tech Business on Their Own Terms - Seth Hassell and Clint Ethington 18.04.2025

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...

#139: Bootstrapped Founder is Getting Ready for the AI Wave at $20M ARR - Shalin Jain 11.04.2025

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 d...

#138: Achieved Strategic Acquisition Just 2 Years After Launch - Brian Kesselman 04.04.2025

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...

#137: Her Amazing Story of 0-$30M ARR with No Outside Funding - Rebecca Shostak 28.03.2025

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 employee...

#136: Practical Founder Has Big Exit and Un-Retires to Build 2nd SaaS Success - Brian Dosal 21.03.2025

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...

#135: Vertical SaaS Investor Shares Proven Paths to Scale Up Big – Dave Yuan 14.03.2025

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...

#134: When It's Time to Close: Helping Founders Shut Down Right – Dori Yona 07.03.2025

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 ove...

#133: Bootstrapper Sells School Fundraising Platform to PE Investors - Howard Gottlieb 28.02.2025

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 pl...

#132: Bootstrapper Serving Private Equity Firms Acquired by PE-Backed Strategic – Richard Change 21.02.2025

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...

#131: No-Code SaaS Platform Bootstrapped to 75,000 Customers – Rachit Khator 14.02.2025

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...

#130: Profitable Product-Led Growth to $30 Million Before Big Exit – Joe Hyrkin 07.02.2025

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...

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