

Practical Founders Podcast
Greg Head
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.
Episodes
Mentioned books

Sep 19, 2025 • 1h 1min
#162: Practical Investor - What’s Working Now in AI-Driven SaaS Growth - Dave Yuan
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 vertical software companies like Toast, ServiceTitan, Jane, and CCC. Tidemark hosts its annual VSaaS Collective Live Event, featuring experienced speakers for hundreds of vertical SaaS founders, on November 5, 2025. In this episode, we discuss the practical opportunities and risks of AI as it is currently developing in 2025 for vertical SaaS companies. Dave explains several powerful examples of how AI is being used in his portfolio companies and the new strategic questions that are being discussed. Dave also shares: Why software companies are getting real results with AI and are not waiting for the AI revolution--it’s here now. How AI-powered “systems of action” have undue influence with important users and can potentially displace entrenched systems of record software. How fast-growing practical software company grow efficiently with well-timed product, channel, and regional expansion. Quote from Dave Yuan, founder of Tidemark Capital “There are a handful of examples where software companies with AI-powered solutions are getting two to five times what they got on a software seat with new outcome-based pricing. They are providing real hard to ROI that's measurable, oftentimes associated with revenue. “And arguably, they're only getting started because the outcomes that they're measuring are relatively low value and they can increase the value of the outcomes and price accordingly. “To capture that value, it depends on competition. Because you can add a lot of value to your customers, but you can only charge for that value unless there's not a lot of competition vying for the same thing.“ Links Dave Yuan on LinkedIn Tidemark on LinkedIn Tidemark website VSaaS Collective Live event Podcast Sponsor – Designli This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical. 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. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Sep 12, 2025 • 54min
#161: When Co-Founders Need Relationship Therapy - Dr. Matthew Jones
Dr. Matthew Jones is a licensed clinical psychologist who specializes in working with co-founders to help manage critical conflicts that threaten their success. He is the author of the book, "The Cofounder Effect: How to Diagnose, Fix, and Scale Healthy Communication for Startup Success." Matt has worked with hundreds of bootstrapped and VC-funded co-founder teams to help them repair and manage their relationships in the context of their growing business. In this episode, we discuss a wide range of co-founder relationship topics, including: Why co-founder alignment sets the floor and ceiling for entire company culture and employee performance. How most co-founder conflicts aren't about surface issues but deeper psychological needs for recognition and power. Why research shows companies founded by friends are more unstable than those started by strangers. The three communication languages of cofounders: operational (business), psychological (feelings), and archetypal (the vibe). Quote from Dr. Matthew Jones, a clinical psychologist “And those differences can start off and be quite positive. If we can manage that tension effectively. That's the magic of co-founders, right? Is the complementary skills and ways of operating that allows you to land somewhere even more effective than you could have individually. “But those same differences that give you that magic sauce also can be sources of friction, like an arthritic knee that just aches every now and then, and sometimes gets worse and worse, right? And so that's where the tensions really have to be managed. And so that's why I advocate for making those differences as conscious and explicit as possible.” Links Dr. Matthew Jones on LinkedIn Cofounder Clarity website Book: “The Cofounder Effect: How to Diagnose Fix and Scale Healthy Communication for Startup Success” 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.

Sep 5, 2025 • 1h 8min
#160: CPG Founder Turned Failure Into a Profitable SaaS Business - Yuval Selik
Yuval Selik is co-founder and CEO of Promomash, a software platform and managed service for Consumer Packaged Goods (CPG) brands to manage their trade promotions and field marketing activities. Yuval is a former CPG founder who encountered the expensive, complex, and crucial process of managing trade promotions with stores and distributors. Promomash launched in 2015 to serve mid-sized CPG companies that don’t have custom software and their own teams to manage promotion spend and budget compliance with retailers. With 125 employees, they now serve over 500 customers with their software and optional analysts who can perform complex sell-through reconciliation and spend analysis. Yuval and his co-founder raised under $1 million from angel investors to get started, and the company is now profitable and growing steadily. Yuval also hosts The 7 Hats Podcast, which helps entrepreneurs master the seven key areas of their lives, ensuring both success and fulfillment. Quote from Yuval Selik, the founder and CEO of Promomash “That's really the reason why we did not raise funds from big investors, because I don't want to have the pressures of somebody on my board telling me that I have to grow 50%, 80%, or 100% year over year. “Sometimes you need to pull back in order to fix your product. Sometimes you need to push forward and step on the gas a little bit. But that decision needs to be my decision, not a VC investor’s decision. “Others in our market that raised big VC funding, in our competitive landscape. They are not run by their founders; they're run by their investors” Links Yuval Selik on LinkedIn Promomash on LinkedIn Promomash website The 7 Hats Podcast 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.

5 snips
Aug 29, 2025 • 1h 4min
#159: Co-Parenting App Reaches $10M ARR Through Pure Bootstrap Growth - Vince Mayfield
Vince Mayfield, cofounder and CEO of TalkingParents, discusses the journey of creating a co-parenting app designed to enhance communication between divorced parents. He shares insights on achieving over $10 million in annual recurring revenue through bootstrap funding. The conversation highlights the app's role in reducing conflicts and improving accountability. Vince emphasizes the importance of customer feedback in refining pricing strategies and evolving the company as it grows. He also reflects on the need for adaptability and lifelong learning in the startup world.

16 snips
Aug 22, 2025 • 1h 12min
#158: $33M Growth Equity After Friends/Family Funding to $10M ARR - Alan Miegel
Alan Miegel, co-founder and CEO of BetterComp, shares his journey of launching a leading compensation management platform. He discusses moving from founder funding to raising $33 million in growth equity, emphasizing the importance of community among B2B SaaS founders. Alan highlights the challenges of maintaining control while securing investments and shares how he prioritized his co-founders over his earnings. The conversation also touches on scaling from $1 million to $10 million in revenue, emphasizing customer relationships, innovation, and strategic funding for future growth.

Aug 15, 2025 • 1h 7min
#157: Seven Years In Survival Mode: A VC-funded Founder's Warning - Zvi Band
Zvi Band, co-founder and former CEO of Contactually, discusses his tumultuous journey through VC funding and the emotional toll of startup life. He candidly reveals the survival mode he endured, often neglecting to celebrate successes along the way. Zvi shares insights on building lasting business relationships, the challenges of modern connection in a digital age, and the delicate balance between bootstrapping and seeking funding. His reflections illuminate the tension between ambitious growth targets and personal well-being, offering valuable lessons for aspiring founders.

10 snips
Aug 8, 2025 • 1h 11min
#156: Bootstrapper Built Vertical CRM to $10M ARR with Co-founder Dad - Shoanak (Sean) Mallapurkar
Shoanok (Sean) Mallapurkar, Founder and CEO of RecruitCRM, shares insights on building a successful family business with his father. They highlight the challenges of managing a remote team while achieving nearly $10 million in recurring revenue. The duo discusses their innovative approach to CRM solutions tailored for staffing agencies, emphasizing performance-based compensation. Sean also explores the transformative role of AI in business operations and their vision of creating a billion-dollar company without venture capital, focusing on sustainable growth and family legacy.

Aug 1, 2025 • 1h 9min
#155: SaaS Founder's Crazy Ride: Boom, Bust, Strategic Sale - Jesse Burrell
Jesse Burrell, CEO and co-founder of BatchData, shares his journey from real estate investor to software entrepreneur. He discusses the explosive growth of his company, reaching $35 million in revenue, followed by the challenges of market shifts and regulatory changes. As they pivoted from B2C to B2B, he highlights the importance of strategic partnerships and innovations in data analytics. Jesse reflects on leadership struggles, maintaining company culture, and the emotional rollercoaster of entrepreneurship, providing valuable insights for aspiring founders.

4 snips
Jul 25, 2025 • 1h 1min
#154: 2nd-Generation CEO Modernizes Mom's Legacy Software Business - Brian Forbis
Brian Forbis, CEO of Blood Bank Computer Systems, Inc., shares his journey of modernizing his mother's legacy software firm. He discusses the critical transition from outdated systems to cloud-based ERP solutions in the blood bank industry. Challenges such as regulatory compliance, data migration, and customer relationships are tackled head-on. Brian emphasizes the unique collaboration within the blood donation sector and the transformative role of AI in enhancing operations. His commitment to saving lives while navigating the complexities of the business shines through.

10 snips
Jul 18, 2025 • 1h 5min
#153: Bootstrapper Killed His First Company to Scale Up Bigger - Chris Brisson
Chris Brisson, CEO and co-founder of Salesmsg, shares his transformative journey from shutting down his first company to launching a successful SMS platform. He emphasizes the shift from one-way to conversational texting, enhancing customer engagement. Chris discusses the importance of reinvesting profits for growth without outside funding, navigating business transitions, and driving innovation. He delves into sustainable strategies for thriving in the SaaS industry, highlighting the benefits of SMS communication and strong partnerships, all while maintaining control and fostering a robust team dynamic.