Practical Founders Podcast Greg Head

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 equity investors support bootstrapped and capital-efficient SaaS founders Why founders should be taking money off the table with every funding or transaction event When can growth equity investment be a good fit for practical SaaS founders Why 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 LinkedIn PeakSpan Capital on LinkedIn PeakSpan 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.
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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 LinkedIn ChapterSpot on LinkedIn ChapterSpot website BillHighway 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. 

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 LinkedIn Niche Academy on LinkedIn Niche Academy website Learn more at practicalfounders.com. 

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 LinkedIn ProShop on LinkedIn ProShop website Mainsail 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.






 

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.

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.