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.   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.

Dori Yona, co-founder and CEO of SimpleClosure, specializes in helping founders gracefully shut down startups. He discusses the emotional and logistical challenges of winding down a business, particularly for those with venture capital. Dori emphasizes the need for swift action, advising founders to prioritize time and learn quickly from failures. He also explores the complexities of financial planning during closures, the role of automation in legal processes, and the global perspective on entrepreneurial churn. A must-listen for anyone facing the tough realities of startup life.

Howard Gottlieb, founder of Read-A-Thon, launched a reading-based fundraising platform that has helped over 4000 schools raise over $30 million. He discusses the explosive growth during COVID, which propelled his company from 40% to 150% yearly growth. Howard shares insights on selling to private equity, focusing on effective negotiation and the emotional challenge of transitioning leadership. He also reflects on the vital blend of luck and hard work in entrepreneurship, emphasizing the importance of humility and strategic wealth management in his journey.

Richard Change, co-founder and CEO of PFA Solutions, shares his inspiring journey of bootstrapping a software company that revolutionized carry and compensation management for private equity firms. He discusses the complexities of private equity integration post-acquisition and reflects on key operational changes. Richard emphasizes the shift from consulting to SaaS, illustrating how trust and credibility were crucial in navigating the private equity landscape. The conversation highlights the importance of strategic support beyond funding and the challenges of maintaining independence in a larger organization.

Rachit Khator, the founder and CEO of Stackby, shares his inspiring journey from working in a corporate venture firm to launching a successful no-code platform that empowers users without technical backgrounds. He discusses the strategic decisions that fueled Stackby’s growth to 75,000 customers while competing against well-funded rivals. Rachit reflects on the entrepreneurial spirit in India's smaller cities, the importance of customer feedback, and innovative growth strategies, all while navigating the challenges of building a sustainable business in a competitive landscape.

Joe Hyrkin, former CEO of Issuu, shares insights from leading the content publishing platform to $30 million in revenue before its acquisition. He discusses the balance of profitable growth and debt management in the tech landscape. Joe highlights the transformation from print to digital marketing, and the importance of building long-term relationships over chasing venture capital. Additionally, he emphasizes sustainable practices and strategic planning needed for success in an evolving market, showcasing how to thrive through challenges.

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.

Scott Desgrosseilliers, founder and CEO of Wicked Reports, shares insights from his journey in building a bootstrapped SaaS company focused on marketing attribution for SMBs. He discusses the complexities of identifying effective marketing strategies, the importance of high-quality data, and the potential pitfalls of VC funding. Scott emphasizes resilience and strategic decision-making in overcoming challenges like near-failure moments, navigating SaaS financing, and fostering sustainable growth while enhancing customer engagement through data-driven insights.

Bryan Forrester is CEO of Boostlingo, a leading on-demand platform for language live interpretation services that is growing quickly and can become a very large company. Boostlingo now has 160 employees and over 17,000 language interpreters who use their software to manage jobs, coordinate schedules, deliver interpreting services, and get paid. Bryan raised some practical funds from angels to start the company in 2016. The company grew 50% or more every year since then. In 2021, Boostlingo raised a growth equity round of funding from Mainsail Partners to provide capital for efficient growth and buy out some early investors. Boostlingo has since made several small acquisitions.  Quote from Bryan Forrester, CEO and co-founder of Boostlingo "Our customers love our software, and our NPS is very high. So when we have customers who love our software, we have high retention and low churn, and our customer costs are really good. When all of that is combined, why would you slow down the growth? "Why would you take your foot off the gas pedal and be very profitable? And we raised a growth equity investment from Mainsail and started spending more on efficient marketing. And it worked. It worked. "What would have happened if we didn't take that small investment with our growth equity partner? We could still have had a positive outcome. We may have already sold the business. But we wouldn't have grown as big as we have become in this very big market." Links Bryan Forrester on LinkedIn Boostlingo on LinkedIn Boostlingo website Mainsail Partners website 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.