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. read less

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

#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 approachHow PeakSpan and other growth equity investors support bootstrapped and capital-efficient SaaS foundersWhy founders should be taking money off the table with every funding or transaction eventWhen can growth equity investment be a good fit for practical SaaS foundersWhy founders should be thinking about the risk-adjusted odds of successful exits at multiple milestones Quote from Phil Dur, Managing Partner of PeakSpan Capital “It’s a big deal to bring an investment partner into your business because now you’re now collaborating with someone on your big decisions. Some founders only need to look themselves in the morning mirror to decide what will happen in their business this year. When you have investor partners, you will have more dialogue to align around important decisions. “Unfortunately, I frequently see entrepreneurs picking their first investor partner without much time getting to know them and experience working with them. That’s why we start actively helping our founders 6 to 12 months before they make a final decision on a transaction. “We want our founders to get a free trial of what the full experience is going to feel like before we work with them. Founders should be doing that with every other investor they are interested in. “Don’t bring someone into your business with eight figures of capital at risk when you just met the partner two weeks before term sheets are due. That’s not a smart strategy for founders.” Links Phil Dur on LinkedInPeakSpan Capital on LinkedInPeakSpan Capital 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.

Episodes

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

#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 approachHow PeakSpan and other growth equity investors support bootstrapped and capital-efficient SaaS foundersWhy founders should be taking money off the table with every funding or transaction eventWhen can growth equity investment be a good fit for practical SaaS foundersWhy founders should be thinking about the risk-adjusted odds of successful exits at multiple milestones Quote from Phil Dur, Managing Partner of PeakSpan Capital “It’s a big deal to bring an investment partner into your business because now you’re now collaborating with someone on your big decisions. Some founders only need to look themselves in the morning mirror to decide what will happen in their business this year. When you have investor partners, you will have more dialogue to align around important decisions. “Unfortunately, I frequently see entrepreneurs picking their first investor partner without much time getting to know them and experience working with them. That’s why we start actively helping our founders 6 to 12 months before they make a final decision on a transaction. “We want our founders to get a free trial of what the full experience is going to feel like before we work with them. Founders should be doing that with every other investor they are interested in. “Don’t bring someone into your business with eight figures of capital at risk when you just met the partner two weeks before term sheets are due. That’s not a smart strategy for founders.” Links Phil Dur on LinkedInPeakSpan Capital on LinkedInPeakSpan Capital 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.

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

#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 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 LinkedInChapterSpot on LinkedInChapterSpot websiteBillHighway 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.

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

#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, Niche Academy struggled at first but eventually grew into a profitable and growing software company with 20 employees that is almost ten years old. Jeromy and his co-founder have no intention of selling the company or raising big VC funding. They are focused on serving their customers, developing their employees, and living great lives with their families right now. Quote from Jeromy Wilson, CEO of Niche Academy “Early on, I idolized VC-funded founders. Why aren’t I growing as fast as that funded company? But now, I say thank goodness. I’m not dictated to like they are, have the problems that they have, or have these massive crashes that some of them end up having. I don’t idolize them as much anymore. “I love the freedom that I have now as the CEO of a profitable software company that didn’t take big VC funding. When you don’t have tons of outside funding, you make different decisions and choices. You do things in a way that is going to make a difference for the customer rather than how we can make more money today. “I’m a real believer in being in charge of your own destiny, having this control, and being able to grow with your profits because you know it’s valid. Your solution is something that your customers see as valuable rather than something that some VCs see as valuable. Links Jeromy Wilson on LinkedInNiche Academy on LinkedInNiche Academy website Learn more at practicalfounders.com.

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

#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 resource planning) software platforms for machine shops. The software manages every aspect of a machine shop business, from orders, finances, inventory, and shop floor operations. The company grew quickly with no outside funding as happy customers spread the word in their industry. Their software company focuses on processes, customer service, and company culture. In 2024, ProShop received a $32 million growth equity investment from Mainsail Partners, which allowed the founders to take money off the table and fund new growth. Links Paul Van Metre on LinkedInProShop on LinkedInProShop websiteMainsail Partners 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.

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

#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 platform used by thousands of small and mid-sized business customers. The company experienced typical internal challenges with leadership, culture, and focus as it grew to 80 employees by 2015. In 2017, Chris and his cofounder Brendan received several significant offers to buy the company. They decided not to sell the business, and the company made a tender offer to buy out their angel investors’ shares and some employee options. Wistia got back to profitability the following year by refocusing on its core business and aligning its team around efficient long-term growth. Wistia is still growing, with 180 employees, tens of thousands of customers, and millions of users. It is very profitable. The founders still love what they do and have no intention of selling the company any time soon. Learn more at practicalfounders.com.

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

#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 popular book about his difficult startup journey, “Lost and Founder: A Painfully Honest Field Guide to the Startup World.” He described in detail the growth of Moz and the exciting growth years, but he also revealed the painful challenges he and the company faced in their later years. In this podcast discussion, he is frank about the pitfalls and brutal realities of big VC funding for founders and the companies they created. Rand created his second software company, SparkToro, in 2018 with an approach that was opposite to the funding, growth, and staffing he used at Moz. We discuss the benefits of practical funding and sustainable profits to create healthy software businesses that support the goals of founders, employees, customers, and investors. Learn more at PracticalFounders.com.

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

#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 assisting with matching and customer service. FreeUp achieved success through organic marketing strategies, niche focus, and great customer service. The business grew to $12 million in revenue in four years before being acquired by The HOTH in 2019. Learn more at practicalfounders.com.

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

#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 marketing industry, working with Amazon, and the importance of building credibility and confidence as a young founder. He also discusses his experience of successful selling his previous company, Grovia, an affiliate partner recruiting services company that was acquired by Acceleration Partners in 2022. Learn more at practicalfounders.com.

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

#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-stage B2B SaaS founders in Phoenix, Arizona. Unlike the traditional VC approach, PHX Ventures supports startups that are growing fast with a capital-efficient approach. PHX Ventures also helps the larger software community in Phoenix with educational events and networks to connect founders, talent, experts, and capital. In this expert episode, Gregg answers common questions about when practical venture funding can be useful for founders and what it means to be capital efficient. Learn more at practicalfounders.com.

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

#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 acquired in a $60 million deal, supported by Beamer investors Camber Partners and other investors. Esben told the Userflow story on the Practical Founders Podcast in episode 42 last year. This is an update about the recent acquisition and his thinking behind selling the company. Learn more at practicalfounders.com.

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

#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 using iPads at their front desks. They also started tracking visiting contractors and vendors with their mobile app, allowing automatic check-ins and tracking for operations managers. Sine grew quickly with global customers and large deals, eventually growing to 100 employees, mostly in Adelaide, with no VC funding or institutional investors. Sine was acquired by Honeywell in 2020 and became a critical product in their property management technology suite. Antony speaks openly about the benefits and challenges of working with institutional investors and why he avoided raising VC funding with Sine. Learn more at practicalfounders.com.

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

#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 on this Podcast How he used SEO to grow his previous software companiesThe basic concepts of search engine optimization (SEO) for SaaS foundersSimple tactics for identifying search terms that would create qualified trafficHis favorite tactic for gaining authority from Google for your organic website contentWhich search engine marketing tools are most useful to maximize your time and investmentThe simple ROI math that founders can use to measure their investment return with SEO Learn more at practicalfounders.com.

#78: Fast-Growing K-12 Education Software Company Will Be Profitable This Year – Justin Hewett

#78: Fast-Growing K-12 Education Software Company Will Be Profitable This Year – Justin Hewett

Justin Hewett started in the software business as a territory sales manager for an education software company in Utah. The company grew and Justin eventually led the sales team as the senior executive. When the company was acquired by PE investors, Justin moved on in 2020 and thought about ideas for a new software business to serve K-12 schools in the US. Flashlight Learning helps K-12 teachers in the US to quickly assess the speaking and writing progress of multilingual students who are learning English. The software captures data for teachers to provide students with improved feedback to accelerate language development. Flashlight Learning grew 300% in 2023 to $4 million in revenue, with a growing team and an outsourced development partner. Justin raised some angel funding to get started and move fast, but they are expecting to be profitable this year with continued growth. Learn more at practicalfounders.com.

#77: Bootstrapped and Winning in Season Ticket Management Software – Morgan Katz

#77: Bootstrapped and Winning in Season Ticket Management Software – Morgan Katz

Morgan Katz is the founder and CEO of Ticketnology. Morgan was an enthusiastic athlete with a degree in sports management who started her career in ticket sales for sports teams and front-line venue management. Morgan saw how companies with season tickets had difficulty managing their digital tickets after COVID, so she started her own company to solve it with a software solution. Ticketnology is a fast-growing leader in the new category of season ticket management software. Started with a mix of hands-on concierge services and a software solution, Ticketnology is now a complete platform that helps season ticket holders manage and distribute tickets to maximize the value of their season ticket investment. Ticketnology is a bootstrapped and profitable software company with just over $2 million in revenue, four full-time employees, and an outsourced development team. They doubled revenues this year and expect to double each year for the next few years. Morgan is a member of a Practical Founders Peer Group. Learn more at practicalfounders.com.

#76: Real Estate Investor Built Her Own CRM Solution and Created a Market Leader – Stephanie Betters

#76: Real Estate Investor Built Her Own CRM Solution and Created a Market Leader – Stephanie Betters

Stephanie Betters was a practicing Nurse Practitioner in heart surgery and an active real estate investor when her frustration with disparate real estate CRM and marketing solutions hit a boiling point. Salesforce and a development partner proposed a project so expensive that Stephanie hung up and decided to build the solution herself. She learned to code and build a useful real estate CRM on Salesforce in three months. Her business thrived with her comprehensive software. Other real estate investors heard about her software and encouraged her to launch the company in 2019 and start selling the software, now called Left Main REI. Word spread in the industry and hundreds of real estate investors signed up in the first year, transforming their businesses. In just over three years, Left Main REI now has hundreds of customers, 20 employees, and nearly $3 million in annual recurring revenue. The company has been bootstrapped and profitable from the first day. Stephanie has a big vision for the company and loves her founder/CEO role; she will no longer be practicing as a Nurse Practitioner as of 2022. Learn more at practicalfounders.com.

#75: Bootstrapped Their Digital Health Platform to Global Scale with 200 Employees – Shameem Hameed

#75: Bootstrapped Their Digital Health Platform to Global Scale with 200 Employees – Shameem Hameed

Shameem Hameed created several companies, including a medical billing services company, before starting ZH Healthcare in 2008 to provide billing and EHR software to innovative healthcare providers. Their BlueBriX software grew into a comprehensive and customizable platform used by hundreds of healthcare organizations around the world. ZH Healthcare now has almost 200 employees in the US and India. The company has been profitable every year and has not taken on any outside funding.

#74: Practical Holding Company Acquires Profitable SaaS Companies – Kevin McArdle

#74: Practical Holding Company Acquires Profitable SaaS Companies – Kevin McArdle

Kevin McArdle spent 15 years working in large software companies before becoming a practical investor and acquirer of smaller SaaS businesses. Kevin is the CEO and co-founder of Big Band Software, a holding company that buys and holds small, profitable, and growing SaaS businesses—with no intent of selling those businesses. Kevin has acquired over 40 businesses in the last 10 years with this buy-and-hold model. As an expert guest on the podcast, Kevin answers common questions from practical founders about the holding company approach as an exit path. Holding companies are common in other industries, including Warren Buffet's Berkshire Hathaway, but relatively new to the software industry. Learn more at practicalfounders.com.

#73: Bootstrapped to successful $67 million exit with medical billing solutions – Harry Hopkins

#73: Bootstrapped to successful $67 million exit with medical billing solutions – Harry Hopkins

Harry Hopkins is co-founder and CIO of Viewgol, a medical billing technology software and services company based in Dallas, Texas. Viewgol was started in 2017 by three founders who got the product and revenues going before hiring additional staff. Their revenue cycle management (RCM) analytics software reveals medical billing problems and missed revenue opportunities at physician offices in the US. As the company expanded its service offerings, Viewgol grew very quickly, from three employees in 2019 to almost a thousand employees at the end of 2023. Viewgol was acquired in October 2023 by CPSI, a public medical billing solutions company, for a reported $67 million in cash and earnouts. Learn more at practicalfounders.com.

#72: Serial entrepreneur funded his biggest idea yet from other businesses – Hamed Mazrouei

#72: Serial entrepreneur funded his biggest idea yet from other businesses – Hamed Mazrouei

Hamed Mazrouie owned a security monitoring business and other businesses for many years before he started his first software and services business called Vivant Corporation. Vivant provides a complete multi-site internet phone system to thousands of restaurants and law firms across the US. Vivant grew steadily and profitably for 10 years and is now a maturing business with 50 employees. In the last four years, Hamed and his growing team have been building Milagro, a complete restaurant management system to increase repeat customer business. They now have happy paying customers who use their powerful software which includes advanced data analytics. Their vision is expanding based on early customer results. Learn more at practicalfounders.com.

#71: Bootstrapped the core software that runs complex manufacturing plants – Subramanyam Kasibhat

#71: Bootstrapped the core software that runs complex manufacturing plants – Subramanyam Kasibhat

Subramanyam Kasibhat has created dozens of products in many different industries. He and his wife were contracted by a friend to build a software solution for a manufacturing plant for a German company. Seven years after they started with their first customer, they rewrote the software to serve other customers and the Vegam Solutions business started to grow. Vegam Solutions is smart factory software for digital optimization and control of complex manufacturing plants. Vegam now has 180 remote employees, primarily in India, with almost $10 million in revenue. They have grown without outside funding by selling to large customers with complex needs. Learn more about practicalfounders.com.