Practical Founders Podcast - podcast cover

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.

Episodes

#108: He Grew His Vertical SaaS Business for 5 Years and Sold It for a Big Prize – Mike Kovarik

Mike Kovarik is the founder and former CEO of Attribytes, a software company he started, grew, and successfully sold in just over five years. Mike was a data analytics leader at large food distributors, where he discovered a chronic challenge with low-quality product data in their massive e-commerce systems. He quit his job, built a product with a friend, and his former employer became his first customer. Attribytes grew steadily in the next few years, serving food distributors and retailers in ...

Aug 30, 20241 hr 8 minSeason 1Ep. 108

#107: Brothers Sold Their Bootstrapped Software Company for $40 Million – David and Chris Sinkinson

Brothers David and Chris Sinkinson attended Queen’s University in Ontario, Canada, when David learned of the problems maintaining the blue emergency phones on campus. He proposed a location-aware mobile safety app, so Chris built it himself, and it worked great. AppArmor grew steadily to become the most popular university mobile safety platform in Canada and the US, and over 250 universities use it. With no outside investors, they bootstrapped the company to $6 million ARR with serious profits b...

Aug 23, 20241 hr 9 minSeason 1Ep. 107

#106: SaaS Pricing Expert Shares Useful Strategies for Practical Founders – Dan Balcauski

Dan Balcauski is the founder and principal consultant of Product Tranquility , a SaaS pricing consultancy. Dan shares the core building blocks of SaaS pricing, including customer segments, value, competition, and positioning strategy. Dan also describes the common mistakes in pricing and the importance of having structured pricing conversations with customers. In this expert interview, Dan shares his perspectives on key SaaS pricing challenges: Why CEOs need to be involved in pricing decisions a...

Aug 16, 20241 hr 3 minSeason 1Ep. 106

#105: Husband and Wife Team Built Popular Software for Wedding Planner Pros - Rob Farrow

Rob Farrow was an experienced marketing executive and his wife Christina Farrow was a successful professional wedding planner. They discovered there was no good software for wedding planner pros, so they decided to build software themselves. They invested their savings, built a loyal team, and started Aisle Planner to serve other wedding planner pros with a complete solution to power their businesses. Aisle Planner grew slowly as they overcame huge obstacles, listened to their customers, and bui...

Aug 09, 20241 hr 17 minSeason 1Ep. 105

#104: Turning VC-Funded Startups Into Profitable, Thriving SaaS Companies – Krista Morgan

Krista Morgan started her first tech company by raising funding and trying to grow very fast. When the company faced a big issue and failed, she learned that big funding was more of a problem than a help in the growth and wind-down processes. Krista is now CEO and General Partner of Stage Fund , an early-stage private equity fund that makes control acquisitions of venture-funded SaaS companies that are stuck and need an alternative option to continue in a practical and profitable way. In this ex...

Aug 02, 20241 hr 3 minSeason 1Ep. 104

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

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 in 2014 to connect this financial assistance funding to patients through healthcare providers like hos...

Jul 26, 20241 hr 5 minSeason 1Ep. 103

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

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 investment decisions in a week. They also invest in practical SaaS founders with capital-efficient a...

Jul 19, 20241 hr 6 minSeason 1Ep. 102

#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 sm...

Jul 12, 20241 hr 2 minSeason 1Ep. 101

#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 e...

Jul 05, 20241 hr 5 minSeason 1Ep. 100

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

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 week’s episode , in which Greg discusses the first five things that VCs don’t tell SaaS startup found...

Jun 28, 202432 minSeason 1Ep. 99

#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 homewor...

Jun 21, 202428 minSeason 1Ep. 98

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

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 multiple dealers in a group with their dealer management system (DMS). DealerBuilt is powerful softwa...

Jun 14, 20241 hr 1 minSeason 1Ep. 97

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

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 explains the basics of payments monetization for practical SaaS founders, answering questions like these...

Jun 07, 202458 minSeason 1Ep. 96

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

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 quality and speed of delivery with technology. Virtuance started with the vision of a software-only ...

May 31, 20241 hr 8 minSeason 1Ep. 95

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

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 and recently through 2024 What are the valuation ranges and factors for practical SaaS companies under...

May 24, 202456 minSeason 1Ep. 94

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

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 understand their own sales processes before hiring salespeople Why technical founders can their sales using a h...

May 17, 202447 minSeason 1Ep. 93

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

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 integration platform that connects Shopify data to accounting software and other applications. Char...

May 10, 202458 minSeason 1Ep. 92

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

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 podcast interview, David discusses: The new questions about revenue models for AI-powered companies The ...

May 03, 20241 hr 5 minSeason 1Ep. 91

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

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 approach is fundamentally different from the venture investment approach How PeakSpan and other growth...

Apr 19, 20241 hr 4 minSeason 1Ep. 90

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

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 ch...

Apr 12, 20241 hr 5 minSeason 1Ep. 89

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

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 learning and development platform for libraries in the US. With his savings and a little angel funding, Ni...

Apr 05, 202458 minSeason 1Ep. 88

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

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 other forward-thinking machine shops. ProShop is now one of North America's leading ERP (enterprise res...

Mar 29, 20241 hr 4 minSeason 1Ep. 87

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

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 million in angel funding, Wistia grew quickly and profitably, becoming a leading video hosting platfo...

Mar 22, 20241 hr 11 minSeason 1Ep. 86

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

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 challenges, causing him to step down as CEO. Rand left Moz in 2018 and later that year published his popu...

Mar 15, 20241 hr 3 minSeason 1Ep. 85

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

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 software and people in FreeUp’s operations, with software handling recruitment and billing and people as...

Mar 08, 20241 hrSeason 1Ep. 84

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

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 3,000 affiliates on the platform. Ian discusses the challenges and opportunities of the affiliate ma...

Mar 01, 20241 hr 1 minSeason 1Ep. 83

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

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 undisclosed amount. In 2023, Gregg launched PHX Ventures , a $27 million seed-funded supporting early...

Feb 16, 20241 hr 8 minSeason 1Ep. 82

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

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, 750 customers, and just three employees with no outside funding. Techcrunch reported that Userflow was a...

Feb 09, 202425 minSeason 1Ep. 81

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

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 in 2013 to help schools, businesses, and large office buildings manage guest sign-ins more securely us...

Feb 02, 20241 hr 27 minSeason 1Ep. 80

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

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 can make the most of SEO investments to drive revenue faster. SEO for Bootstrapped SaaS Topics Discussed...

Jan 26, 20241 hr 5 minSeason 1Ep. 79