Practical Founders Podcast

Mike Trasatti, the former CEO of DealerBuilt, shares insights on bootstrapping an auto dealer software business, revolutionizing the industry with their DMS, selling to private equity, navigating COVID challenges, and the CEO's role as the 'Chief Believer Officer'. The podcast covers lessons learned, growth strategies, and the importance of confidence and humility in leadership.

Brian Abernethy, payments expert, discusses integrating payments and monetization for SaaS businesses. Topics include when to monetize payments, adding profitable offerings, and lowering payment bills. He highlights misconceptions, investor values, and key steps for SaaS founders. The conversation also explores the impact of payments on customer experience and software growth strategies.

Jeff Corn, former CEO of Virtuance, shares the journey of bootstrapping, scaling, and selling a tech-enabled services business for real estate. Topics include launching a software-only solution, growing with a service model, achieving SaaS-like margins, and navigating the sale process. Insights on the importance of feedback, pivoting business models, adapting to market shifts post-COVID, and the emotional rollercoaster of M&A. The podcast celebrates the challenges and victories of practical entrepreneurship.

Adam Haynes, a managing director at GLC Advisors, shares insights on SaaS valuations and acquisition trends. Topics include factors affecting software acquisitions, valuation ranges for practical SaaS companies, key areas for founders to focus on pre-acquisition, and the role of M&A advisors. Haynes emphasizes the importance of having a remediation plan for tech debt and highlights potential deal-breakers like IP ownership issues.

In this discussion, Matt Wolach, a seasoned SaaS sales coach with a rich background in sales leadership, reveals game-changing insights for B2B SaaS founders. He emphasizes the importance of understanding one's sales process before hiring. Matt also highlights the need for emotional engagement with buyers, illustrating how effective demos focus less on the product and more on addressing customer problems. Learn about the significance of follow-up communication and the structured Three C's Model to boost demo success rates while navigating the unique challenges in startup sales.

Charlie Alsmiller, Founder of APIWORX, shares insights on bootstrapping software companies by niching in on specific customer problems. He emphasizes the importance of focusing on superpowers as a startup CEO and delegating other tasks. Topics include challenges faced in his first VC-funded venture, transitioning to a services business for funding, and the strategy of growing faster by narrowing down on key vendor ecosystems.

David Evans, managing partner of Sentiero Ventures, discusses the role of AI in software development and revenue models for AI-powered companies. He highlights the challenges and opportunities of AI, the importance of clean data for training models, and balancing AI in the go-to-market strategy. The podcast delves into the impact of AI on various industries and the evolving revenue models for AI-powered companies.

Phil Dur, co-founder of PeakSpan Capital, discusses the benefits of growth equity for capital-efficient software founders. Topics include differences between venture capital and growth equity, the importance of partnering with the right firm, and the advantages of focus and specialization for business success.

Joe McMenemon and his college roommate, Brendan, knew they wanted to start a business together. They had run their college fraternity chapter and saw the problem of managing members and collecting payments. So they lived frugally and built a software solution  for fraternities and sororities to solve this problem. ChapterSpot grew slowly over several years as they sold to local chapters. Eventually, the national associations came calling, requesting an enterprise solution to manage hundreds of chapters in one system. They rewrote the platform to run on Salesforce and grew faster with more employees.  ChapterSpot grew profitably to over 30 employees, with 40 large organizations managing thousands of chapters and millions of members on the platform. ChapterSpot was acquired in early 2024 by BillHighway, a strategic acquirer with a payments platform. Quote from Joe McMenemon, CEO of ChapterSpot "Long shots are probably not as crazy as you may think they are, but they're just going to require time. If you think you'll make a bunch of money in three years, it's probably very unlikely. But if you're willing to put in the time and work at it every day, you're most likely going to be able to figure out the right path to success. "My favorite quote is from James Clear: It's the courage to start, a few lucky breaks along the way, and a ton of hard work. That's the formula. "Once you get started, are you putting yourself in a position where you can do it at a level that's best in the world for the problem you are solving? If you're the only one trying to solve the problem and you do it long enough to catch a few lucky breaks, well, eventually, you'll get there." Links Joe McMenemon on LinkedIn ChapterSpot on LinkedIn ChapterSpot website BillHighway 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. Get weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

Jeromy Wilson, Founder of Niche Academy, discusses his journey of founding a profitable software company for libraries without VC funding. He emphasizes the benefits of independence, customer focus, and work-life balance in building a successful business in a niche market.