Greg Head

Practical Founders Podcast

Business EN ↓ 203 episodes

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.

Author

Greg Head

Category

Business

Podcast website

practicalfounders.com

Latest episode

Jul 10, 2026

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Episodes

#103: Healthcare Software Startup Sold to VC-Funded Competitor During COVID Era – Ian Manners 26.07.2024

Ian Manners was a successful consultant for pharmaceutical companies in the US when he discovered a major problem that needed a software solution. Big pharma companies provide financial assistance funding for patients who require their drugs but struggle with high costs, but these funds are difficult to access and manage for patients and healthcare providers.  Ian and his cofounder created  Vivor...

#102: Practical VC Shares Advice for SaaS Founders From Over 2000 Investments – Dave Lambert 19.07.2024

Dave Lambert and the team at Right Side Capital Management are the most active venture capital investors, having invested in over 2,000 startups since 2009. Right Side Capital is a "pre-VC" institutional investor that operates very differently from traditional VCs: investing when SaaS companies have just a little revenue using a submission form on their website, then responding quickly and making...

#101: Bootstrapped SaaS Founder Has No Intention of Selling Even as They Grow Big – Todd Watson 12.07.2024

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 the...

#100: She Scaled Her Software App as a Successful Franchised Service Business – Erin Fletter 05.07.2024

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...

#99: What VCs Don't Tell Founders About Raising Funding (Part 2 of 2) – Greg Head 28.06.2024

In this second of two episodes, Practical Founders Podcast host Greg Head discusses the next five important things venture capital investors don't tell new SaaS startup founders. Greg emphasizes that VCs invest in very few businesses and seek big wins. He highlights the importance of understanding the game of venture capital funding and the alternatives available to SaaS founders. Check out last w...

#98: What VCs Don't Tell Founders About Raising Big Funding (Part 1 of 2) – Greg Head 21.06.2024

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, Hos...

#97: Bootstrapped Auto Dealer Software and Sold to Private Equity Buyer – Mike Trasatti 14.06.2024

Mike Trasatti spent 10 years in the automotive dealer software business before he found an auto dealer in Iowa who had built is own complete software system. They partnered up in 2008, and Mike became the first CEO of the spinout software company, DealerBuilt. DealerBuilt  grew slowly as a bootstrapped startup in a market full of large incumbent competitors. They had a better approach to managing...

#96: Expert Explains Payments Monetization For Your SaaS Business - Brian Abernethy 07.06.2024

Brian Abernethy, founder of  Utopaya , is an expert in helping SaaS leaders navigate the complicated process of adding payments monetization to their product offerings and business strategies. With a long history in the payments industry, Brian has worked with hundreds of early-stage SaaS leaders and their investors to optimize their payments strategies. In this expert podcast interview, Brian exp...

#95: Bootstrapped, Scaled, and Sold a SaaS-like Tech-Enabled Services Business 31.05.2024

Jeff Corn is the co-founder and former CEO of Virtuance , one of the US's leading real estate photography and marketing providers. In 2010, Jeff was in the real estate investment business and wondered why it took $10,000 and nearly a month to get professional photos for new listings. He and a cofounder started taking photos to serve busy real estate agents to learn what was needed and improve the...

#94: Practical M&A Advisor Explains SaaS Valuations and Acquisition Trends – Adam Haynes 24.05.2024

Adam Haynes is a managing director at  GLC Advisors , an M&A advisory firm that helps bootstrapped founders to successfully sell their companies. The software advisor team at GLC has been working with practical software founders for over 15 years and has completed over 100 software transactions.  In this expert interview, Adam shares: What has changed in software acquisitions in the last 20 years...

#93: SaaS Sales Coach Shares How to Improve Your Demo Close Rate – Matt Wolach 17.05.2024

Matt Wolach spent 15 years as a successful SaaS account rep, sales leader, and software founder before becoming a  SaaS sales coach  for early-stage B2B SaaS companies. He has worked with over 250 SaaS founders and sales leaders worldwide to improve their close rates and create repeatable sales systems quickly. In this episode, Matt shares: How B2B SaaS founders need to learn to sell and understan...

#92: Bootstrapped Integration Platform Growing Faster by Niching In and Doubling Down – Charlie Alsmiller 10.05.2024

Charlie Alsmiller is the founder and CEO of APIWORX , a powerful integration platform for mid-sized ecommerce companies. He is an experienced practical founder who has created and grown several software companies. His first venture was VC-funded and shut down quickly in 2001. His next software ventures were bootstrapped with funding from services revenue and his own savings. APIWORKS is a powerful...

#91: How AI Is (and Isn't) Changing the Game for Practical SaaS Founders – David Evans 03.05.2024

David Evans, the managing partner of  Sentiero Ventures , a seed fund focused on AI-focused software startups. David discusses the role of AI in software development and the opportunities it presents for practical SaaS startups. He shares his journey with AI and predictive modeling in his previous companies and the key factors he looks for when investing in AI-powered companies. In this expert pod...

#90: Why Growth Equity is Practical Funding for Founders Who Are Scaling Up Efficiently – Phil Dur 19.04.2024

Phil Dur is cofounder and managing partner of PeakSpan Capital, a growth equity investment firm that works with bootstrapped SaaS founders who are scaling up to become sizable market leaders. Phil has been funding capital-efficient software founders for over 20 year and has served on 45 boards with those companies. In this expert podcast interview, Phil explains: Why the practical growth equity ap...

#89: Scrappy Bootstrappers Grew Up to Be the Enterprise Leader in Their Market - Joe McMenemon 12.04.2024

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. Eventual...

#88: Persevered to Find a Scalable Niche in a Crowded Software Market – Jeromy Wilson 05.04.2024

Jeromy Wilson spent over ten years in the software business as a product management leader working for PE-owned and VC-funded software companies. When he decided to start his own software company, he focused on serving public libraries, like his father, who had created a successful library automation software company called Dynix. Jeromy is the founder and CEO of  Niche Academy , the leading learn...

#87: Created Software for Their Own Business that is Now Changing the Industry – Paul Van Metre 29.03.2024

Paul Van Metre was the co-founder of a successful machine shop that manufactured custom parts for the aerospace and medical device industries. Over 15 years, they created and improved software to run their entire business, which created huge efficiencies and helped them manage their growth. They sold that business in 2014 to focus on selling their complete software platform, called ProShop, to oth...

#86: Growing Profitably and Getting Big with Happy Founders After 18 Years – Chris Savage 22.03.2024

Chris Savage is the co-founder of  Wistia , a leading video marketing platform for businesses. Wistia was started in 2007 by Chris and a college friend when inexpensive cloud hosting and easy web video encoding became available. They created the first easy way to host and share videos with deep analytics and no ads for marketers to use on their websites.  With a bootstrapped approach and just $1.2...

#85: Moz Founder Rand Fishkin Reveals the Pains of VC Funding and an Alternative Funding Approach 15.03.2024

Rand Fishkin is the founder and former CEO of  Moz , a leading SEO software for marketers created in 2007 that grew out of the active followers of Rand's popular SEOmoz blog. Moz grew quickly to over $30 million in revenue by 2013, having raised $30 million in venture capital investment. When growth slowed in 2014, the company faced many internal difficulties and Rand dealt with mental health chal...

#84: Scaled and Sold a Marketplace of Pre-Vetted Freelancers – Nathan Hirsch 08.03.2024

Nathan Hirsch, co-founder of  FreeUp , shares his journey of building and selling the company and his other business adventures. FreeUp provides clients with pre-vetted virtual assistants (VAs) and freelancers in an online marketplace.   Nathan discusses the importance of niching down and targeting specific industries, such as e-commerce, to attract clients. He also highlights the combination of s...

#83: Second-time founder grows Amazon affiliate marketing platform to $3M ARR in one year – Ian Brodie 01.03.2024

Ian Brodie, the co-founder and CEO of Levanta, shares his journey of building a successful SaaS company in the affiliate marketing space. Levanta  is an affiliate marketing platform for Amazon sellers, enabling them to connect with content creators, publishers, and influencers to drive sales and traffic to their Amazon storefronts. The company has experienced rapid growth, with over 700 brands and...

#82: Former SaaS Founder Launches Seed Fund for Capital-Efficient Growers in Phoenix – Gregg Scoresby 16.02.2024

Gregg Scoresby founded CampusLogic in Phoenix in 2021 to provide software for colleges and universities in the US to make it easier for students to apply for college loans and grants online. Initially self-funded, CampusLogic raised investment and grew faster, becoming a leading provider of software to universities with $50 million in revenue. In 2022, CampusLogic was acquired by Ellucian for an u...

#81: Bootstrapped Founder Sells His Profitable SaaS Company with $4 Million ARR – Esben Friis-Jensen 09.02.2024

Esben Friis-Jensen and his cofounder, Sebastian Seilund, teamed up in 2021 to create  Userflow , a no-code user onboarding product for SaaS companies. This week, it was announced that Userflow has been acquired by  Beamer , a maker of product user engagement software that also used product-led growth strategies just like Userflow.  Userflow is profitable and growing, with over $4 million in ARR, 7...

#80: Second-Time Founder Wins Bigger with Bootstrapped SaaS Company – Antony Ceravolo 02.02.2024

Antony Ceravolo is a successful two-time startup founder from Adelaide, South Australia. He started his career in investment banking but left in 2002 to start a DVD rental business in London that raised funding from big VCs and Amazon. It grew into Lovefilm.com, which was later acquired by Amazon in 2011 to become part of their movie streaming service.  He moved back to Adelaide and started Sine i...

#79: Practical Founder with 3 Exits Explains How SEO Can Drive Efficient Growth – Raj Khera 26.01.2024

Raj Khera is an experienced  practical SaaS founder  who has used search engine optimization (SEO) to grow businesses very efficiently. Now he coaches entrepreneurs at  MoreBusiness  on how to use organic SEO as a core part of their marketing engine.  In this expert interview, I ask Raj to explain the basics of SEO for SaaS founders, what tools and techniques are most useful, and how SaaS founders...

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