
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.
Latest episodes

Aug 23, 2024 • 1h 9min
#107: Brothers Sold Their Bootstrapped Software Company for $40 Million – David and Chris Sinkinson
David and Chris Sinkinson, co-founders of the successful mobile safety app AppArmor, share their entrepreneurial journey from college campus to a $30 million acquisition. They discuss the innovative features that set their app apart and the challenges of scaling without outside investment. Insightful reflections on ignoring detractors resonate as they emphasize market validation over peer approval. The brothers also introduce their book, 'Startup Different,' aiming to debunk common startup myths and inspire future founders.

6 snips
Aug 16, 2024 • 1h 3min
#106: SaaS Pricing Expert Shares Useful Strategies for Practical Founders – Dan Balcauski
Dan Balcauski, founder of the SaaS pricing consultancy Product Tranquility, dives into the art and science of pricing strategies. He emphasizes the critical role of CEOs in shaping these strategies and highlights the need for structured pricing conversations with customers. Balcauski discusses common pricing pitfalls and the impact of customer segments on pricing models. He also explores how AI is transforming pricing in the SaaS landscape, urging founders to view pricing as an evolving process rather than a one-time decision.

Aug 9, 2024 • 1h 17min
#105: Husband and Wife Team Built Popular Software for Wedding Planner Pros - Rob Farrow
Rob Farrow, an experienced marketing executive, and Christina Farrow, a professional wedding planner, co-founded Aisle Planner to address the lack of suitable software for wedding planners. They share their journey of innovation, highlighting the challenges they faced and the importance of aesthetics and functionality in their product. The couple discusses navigating the pandemic's impact on their business, strategic funding hurdles, and their emotional experience during a significant acquisition, demonstrating resilience and commitment to their vision.

Aug 2, 2024 • 1h 3min
#104: Turning VC-Funded Startups Into Profitable, Thriving SaaS Companies – Krista Morgan
Krista Morgan, CEO and General Partner at Stage Fund, specializes in revitalizing struggling SaaS companies. She shares her journey from one startup's failure due to excessive growth funding to creating a successful model for distressed firms. Key highlights include the pitfalls of 'growth at all costs' strategies, the importance of sustainable growth, and the advantages of acquisitions over organic expansion. Krista emphasizes the need for practical decision-making while keeping a strong vision, turning challenges into opportunities for profitability.

Jul 26, 2024 • 1h 5min
#103: Healthcare Software Startup Sold to VC-Funded Competitor During COVID Era – Ian Manners
Ian Manners, a former consultant turned entrepreneur, co-founded healthcare software company Vivor to bridge patients with financial assistance for prescriptions. He shares insights on the startup's journey, helping over 100,000 patients access $2 billion in aid. Ian reflects on the challenges of merging Vivor with competitor TailorMed during COVID-19, discussing the emotional and strategic nuances of such a sale. The episode also highlights the complexities of integrating healthcare solutions and the evolving landscape of startup funding in this sector.

Jul 19, 2024 • 1h 6min
#102: Practical VC Shares Advice for SaaS Founders From Over 2000 Investments – Dave Lambert
Dave Lambert, a venture capital investor at Right Side Capital Management, has funded over 2,000 startups since 2009, specializing in early-stage SaaS companies. In this discussion, he unveils why traditional VC routes may hinder a successful exit and emphasizes capital efficiency. Lambert also sheds light on the effective use of AI in startup growth and the current state of acquisitions in the SaaS space, revealing valuable insights for founders aiming for smaller exits but significant impact.

Jul 12, 2024 • 1h 2min
#101: Bootstrapped SaaS Founder Has No Intention of Selling Even as They Grow Big – Todd Watson
Todd Watson is the owner and CEO of Showit, a popular no-code website builder and platform for designers and photographers. Todd is a native of Phoenix, Arizona where he started as a videographer before joining a friend in 2007 to create a scrappy software business that made inexpensive photo-presenting and sharing tools for photographers. The Showit company was created when Todd took one of their two products and half the small team in 2010 to spin off Showit as an independent business. The small revenue from the small customer base and his own savings allowed them to rewrite Showit for the cloud and then continue their fanatic customer focus to keep growing every year—without any outside funding. Now Showit is used by 50,000 designers, photographers, and small businesses as their website platform using its elegant “Photoshop-like” no-code visual builder. The Showit company is growing quickly every year and is profitable, yet Todd has no interest in taking outside funding or selling his beloved company. Links Todd Watson on LinkedIn Showit website Showit website design marketplace: Showit on LinkedIn 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 the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

Jul 5, 2024 • 1h 5min
#100: She Scaled Her Software App as a Successful Franchised Service Business – Erin Fletter
Erin Fletter had a long career in the restaurant business before starting an after-school enrichment program to teach kids how to cook at her daughters’ school in 2011. Her cooking program became popular, and she improved and expanded it to become a paid program called Sticky Fingers Cooking. Soon, she had a sizable business with over 100 chef-instructor employees who conducted engaging classes daily in Denver. Her team created custom software to help manage their complicated operations, from enrolling students, coordinating instructors, and building relationships with schools to handling payments and payroll. The software grew slowly initially but eventually became a powerful system that helped them scale their business and run efficiently. Erin considered turning her business into a software company, as many tech-powered businesses do. Instead, they kept improving the software and expanding operations, serving over 100,000 students and thousands of schools and venues. Now Sticky Fingers Cooling is a fast-growing and successful franchise business with a software superpower. Quote from Erin Fletter, CEO of Sticky Fingers Cooking “Our business has a lot of logistics, coordination, and operations. Our own custom software, we call it the Dash, it takes about 85% of all operations off the table for humans. This enables our chef-instructors to connect with their students and our franchise owners and regional directors to focus on building relationships with schools and parents. “Over the years, we have been contacted by very large organizations like YMCAs, Boys and Girls Clubs, and other after-school enrichments about our software. They would see our automatic rosters getting texted and emailed at the venues that we were teaching in, and they asked, What are you using? What is this? And we told them, Well, it’s our own software, sorry. “We had talked for years about selling our software as a white-label solution because the demand is there. We’ve had inquiries for the last 10 years. That was a direction we could have taken. “But I’m just laser-focused on Sticky Fingers Cooking. It’s a very simple business, and our technology helps us do it incredibly well. We want to be the best at what we do. I didn’t really want a diversion from the path of taking our business national through franchising.” Links Erin Fletter on LinkedIn Sticky Fingers Cooking on LinkedIn Sticky Fingers Cooking 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 the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

Jun 28, 2024 • 32min
#99: What VCs Don’t Tell Founders About Raising Funding (Part 2 of 2) – Greg Head
Entrepreneur and Practical Founders Podcast host Greg Head delves into the realities of VC funding for SaaS founders, stressing the need for big wins and high valuations. He sheds light on the challenges, risks, and pressure associated with raising venture capital for startup founders.

Jun 21, 2024 • 28min
#98: What VCs Don’t Tell Founders About Raising Big Funding (Part 1 of 2) – Greg Head
In this episode, Practical Founders Podcast host Greg Head discusses the most important things venture capital investors don’t tell new SaaS startup founders. He emphasizes that VCs invest in very few businesses and are looking for big wins. Greg highlights the importance of understanding the game of venture capital funding and the alternatives available to SaaS founders. Quote from Greg Head, Host of the Practical Founders Podcast “If you’re thinking about raising VC investment, do your homework so you know what you are signing up for before. VCs are not evil people, and it’s not a bad business model—for them. “The world has changed for SaaS founders in the last 5-10 years, and it’s still changing. You no longer need VC funding to start most B2B SaaS software companies. It’s 10 times cheaper to create a sellable SaaS product and go to market now. And founders can get higher multiples earlier when they sell their companies. VC funds are also much bigger, so it’s riskier for founders to play that game. “You just don’t need to make a crazy all-or-nothing bet that your company will create a billion-dollar exit in seven years, which VC investors require to win. The best case scenario for 80 to 90 % of software companies is NOT to raise big institutional venture funding.” Links Greg Head on LinkedIn Practical Founders website Practical Founders Podcast Greg Head’s blog 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.