Practical Founders Podcast

Phil Stern, Operating Principal at Mainsail Partners, specializes in growth equity for bootstrapped vertical SaaS companies. He shares insights on hiring the first head of sales to transition from founder-led to scalable sales. Phil highlights the importance of operational support and establishing trusting relationships with founders. He discusses the need for effective customer profiling and the transformative role of AI in SaaS. The conversation emphasizes how targeted investments can accelerate growth while ensuring product-market fit and a focus on key performance indicators.

Sean Hoban, co-founder and former CEO of Kimble Applications, shares his journey from professional services to building a $30M SaaS business. He discusses the strategic shift needed to grow in the SaaS market and his experience using the Salesforce ecosystem. Sean also dives into challenges like customer onboarding and navigating funding dynamics, including insights on the EIS scheme for angel investors. He emphasizes the importance of engaging with ideal customer profiles and the impact of private equity on transitioning to a successful SaaS model.

Josh LaSov, founder of Cauzzy.ai and former CEO of Satori Reporting, shares his entrepreneurial journey, highlighting the transition from a service-oriented model to scalable software solutions. He dives into the challenges of the NetSuite ecosystem, the benefits of bootstrapping, and the significance of strategic angel investors. After a brief retirement, LaSov found fulfillment in launching his AI-powered startup, which aims to revolutionize financial analysis. He also discusses innovative team-building methods and the evolution of accounting software into advanced tools.

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 founders package, promote, negotiate, and close their transactions. Potential buyers are vetted for financial viability and identity confirmation before getting confidential details for any deal. In this episode, Andrew describes their typical seller and buyer profiles, the typical process for a founder to sell a small and profitable SaaS company, typical multiples of profit that financial buyers offer, and founder transition periods. Quote from Andrew Gazdecki, founder and CEO of Acquire.com "There are three buckets of active buyers on Acquire.com. The first is below $100,000 net profit. That's going to be an individual buyer looking for something with maybe a little bit of product market fit. They want to take the product, grow it a little bit, see what they can do from there. They're buying a very, very early startup. So some buyers will actually start small and then work their way up. "From $100,000 to $1 million in net profit in our middle range, the buyer will a blend of "micro PE firms" and holding companies that want to get their hands on a business where there's a lot more going on. And then a $1 million in profit and above is going to be for the more traditional private equity or strategic buyers." Links Andrew Gazdecki on LinkedIn Andrew Gazdecki on Twitter Acquire.com on LinkedIn Acquire.com website 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.

Seth Hassell and Clint Ethington, childhood friends and co-founders of Genius Monkey, delve into building their bootstrapped ad tech empire without relying on venture capital. They discuss their unique partnership, the significance of profitability over rapid expansion, and how they compete with giants like Google. The duo shares insights on fostering a strong company culture, innovative marketing strategies, and the value of non-dilutive funding. They emphasize the importance of adaptability and learning from failures in the ever-evolving ad landscape.

Shalin Jain, the Founder and CEO of HappyFox, discusses his journey in building a $20M ARR bootstrapped company focused on help desk management software. He delves into the transformative role of AI in reducing software costs and enhancing efficiency. The conversation highlights the evolution of customer support and the importance of a product-led growth strategy. Jain also emphasizes the need for user-centric design in software, the pressures of entrepreneurship, and the impact of ethical practices in business.

Brian Kesselman, co-founder and CRO of Skematic, shares his journey from lawyer to tech entrepreneur in compliance management. He discusses the rapid growth of Skematic within two years, focusing on solving core problems for legal and compliance professionals. Brian emphasizes the importance of proactive sales strategies, customer feedback, and independence in startup culture. He contrasts working in private equity with a family office model, and highlights the successful acquisition of Skematic, reflecting on the pivotal decisions that led to their remarkable success.

In this insightful conversation, Rebecca Shostak, co-founder and chief brand officer of Flodesk, shares her impressive journey of growing the email marketing platform to over $30M in annual recurring revenue—completely bootstrapped. She delves into vital topics like product design, the innovative unlimited pricing model, and maintaining profitability without outside funding. Rebecca also highlights the significance of understanding challenges before hiring and discusses how AI is enhancing their services. Prepare for an inspiring tale of entrepreneurship and creative problem-solving!

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.   Strety is a fast-growing SaaS business with a popular app for small businesses using the EOS® approach to manage their businesses. It has 10 employees, hundreds of customers and partners, and no outside funding. Brian brought back some of his previous team to build another sustainable and valuable software company. Links Brian Dosal on LinkedIn BrightGauge website Strety on LinkedIn Strety website Entrepreneurial Operating System (EOS) website Traction book by Gino Wickman Anything You Want book by Derek Sivers   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.

Dave Yuan, founder of Tidemark Capital and investor in successful vertical SaaS companies like Toast and ServiceTitan, shares invaluable insights on scaling strategies. He discusses the significance of control points in thriving markets and the evolving landscape shaped by AI. Dave emphasizes the importance of community among founders, innovative growth frameworks, and adapting to challenges posed by new technologies. He urges vertical SaaS entrepreneurs to harness AI thoughtfully to enhance their offerings and stay competitive.