Practical Founders Podcast

Jesse Welch runs Midcap Global , a boutique investment bank advising companies with $1 million to over $10 million in profits. He came from film production, AI startups, a real estate private equity firm and a crypto hedge fund sold in 2021, and he now teaches founders on his Capital Love Letters YouTube channel . His core point: the headline exit price is a vanity metric; it's the other terms tha...

Jerry Nettuno started Schedulicity in Bozeman, Montana, in 2009 after struggling to book his own haircut as a single father. He recruited his first developers from Denver, paid for the build himself, and launched online scheduling for hairstylists, trainers and other small service businesses at $29 a month, starting with about a hundred customers around Bozeman. To fund a bigger team and faster gr...

Rob Walling has been publishing Startups for the Rest of Us every week since 2010 — he recorded episode 855 the morning of this interview — and has written five books on bootstrapped SaaS, with a sixth on the way. He started five companies before turning to investing, all of them bootstrapped, and sold Drip in 2016. In 2018 he and co-founder Einar Vollset launched TinySeed , the first accelerator...

Josh Allen is founder and CEO of Tratta , software for debt collection agencies and creditor rights law firms that gives consumers self-service payment tools and gives agents modern back-office tools. He started in merchant services, hired contractors to build a payment portal, and found out the hard way that nobody was waiting for it. That first platform landed five clients in about three years w...

Shawn Boyer is founder and CEO of goHappy , a frontline employee communication and engagement platform for companies with a thousand or more hourly workers in restaurants, logistics, manufacturing, and retail. Before that he started Snagajob in 2000, a job marketplace for hourly workers, funding it with credit cards and family money until it reached profitability after four years. Then he raised t...

Riccardo Pisano grew up in Rome, started coding at fourteen, and came to the US for a master's in e-commerce. After a venture-chasing startup called Proximity stalled, he and co-founder Roy turned an internal LinkedIn outreach script into Growth-X in January 2016. Riccardo refused to write a line of code until customers had paid, unlike his previous startup attempt. Growth-X started as pure Linked...

Steve Wolfe co-founded Growth Street Partners in San Francisco about ten years ago with his partner Nate Grossman, after a career in software-focused private equity. The firm's name is the point: they don't invest on Sand Hill Road, Wall Street, or even Main Street, but a street or two behind it, where the rent is lower and practical founders put their earnings back into the business. Growth Stree...

Heath Adams is a military veteran in Albuquerque who started posting ethical hacking videos on YouTube under the handle The Cyber Mentor. The videos found a large audience, consulting clients started showing up, and he launched TCM Security as a penetration testing shop. Then he put a course on Udemy in December and it did six figures in its first week. TCM became a training company quickly. By th...

Lynn Burghardt is a fifth-generation owner of Burghardt Sporting Goods — the oldest family-owned sporting goods store in the country, founded in 1881. Chipply grew out of that business: after years of hacking together their own tools for team apparel orders, Lynn and two brothers built the software solution the decorated-apparel industry didn't have, funded by a $250,000 angel check from their fat...

Jay Maharaj built TeamLinkt in Saskatoon, Saskatchewan, a place not known for software. He saw the problem while coaching his own kids: the hockey team had a budget for a team communication app, and the soccer team didn't, so he either paid for it himself or went without. He launched the TeamLinkt app in 2018 and its back-office platform in 2020. TeamLinkt now powers more than 3,500 organizations...

Ajay Gupta founded Stirista in San Antonio after helping with micro-targeting a presidential campaign. His first product identified people who spoke a second language for multicultural marketing — built from scanned baby-name books, a hundred thousand first names, and 107 sales calls before Dish Network became the first big client at $100,000. Stirista now helps brands find new customers using dat...

Vic Levitin is a serial founder who built companies in Israel for two decades before fleeing the war with his young family to the island of Koh Samui, Thailand. His first SaaS company, CrazyLister, grew out of his own e-commerce business where he needed a simple way for eBay sellers to build professional listings without knowing HTML. CrazyLister raised about $700K, then a similar second round, an...

Steve Oriola isn't the founder of Unbounce — he's the CEO that Crest Rock Partners brought in to run and transform it. A sales-and-marketing software veteran who spent a decade at Constant Contact, and even ran Act! for a spell (ACT! is the product and company I helped grow and run myself 10 years earlier!). Steve joined Unbounce in January 2024 and acquired the Insightly CRM six months later, mer...

Mike Lyon is the founder and managing director of Vista Point Advisors, a boutique sell-side investment bank he started almost sixteen years ago. A former chemical engineer at Exxon and BP who later joined Citigroup's tech M&A team, he built Vista Point to solve a conflict of interest he watched play out on Wall Street: bankers quietly working both sides of a deal. Vista Point Advisors represents...

Wayne Cartmel grew up on a small farm in the Lake District region of northwest England and was selling chickens by the age of four. He trained as a maths teacher in Bedfordshire and could not believe the process he had to go through to apply for jobs — hours of Word-based application forms, one after another. He asked why nobody had digitized it, and then decided to do it himself. Funded by a £5,0...

Eran Galperin is a Brazilian jiu-jitsu black belt who had already had one VC-backed marketplace failure when he started Gymdesk . Originally called Martial Arts on Rails, it launched in 2016 as a naive version of what he thought a gym needed. He was training five or six times a week and every gym owner he knew hated the software they used. For four years he couldn't acquire customers, so he took a...

Cliff Sentell co-founded Compass Professional Health Services in Dallas in 2005, where he and two partners each put in $20,000 and bought a single server. They started in healthcare price transparency, reverse-engineering the cost of specific procedures on specific plans out of billions of insurance claims. The first idea, selling to consumers, flopped, because frustrated patients wouldn't pay $20...

Matthew Bullis grew up in a mud-brick hut with no running water on a small island off South Korea, was adopted to the US at 11 speaking no English. After a dot-com near-miss, he took over his brother's struggling concrete-pumping software — down to about $20,000 a year — for 90% of the company. He taught himself to code and rebuilt it from scratch. From 2016, Bullis built RapidWorks into the opera...

Nick Olsen is the Head of AI Innovation at Mainsail Partners , where he works hands-on with 25 scaling vertical SaaS companies helping them adopt AI in engineering and product. Before joining Mainsail, Nick spent 20 years helping build ResMan from a 3-person startup into a scaled software company serving the multifamily property management market. Today, Nick leads a team of engineers who embed di...

Paul Hoeper founded InvoiceASAP after spotting a simple but painful problem in 2009: home service businesses couldn't easily create invoices or collect payments from the field using mobile devices. He started in New Orleans, launched during the earliest days of mobile apps, and built one of the first mobile invoicing products integrated with both Square and Clover. He also suffered through several...

Jerry Alderman is the co-founder and CEO of Valkre Solutions , a SaaS platform built specifically for key account managers who oversee the largest and most strategic customers in global B2B companies. After careers in engineering, sales, leadership, entrepreneurship, and customer value consulting, Jerry discovered that key account managers were still managing critical customer relationships with s...

TJ Joosten is the co-founder of RevFixr , a pricing and monetization consultancy that helps SaaS companies improve pricing, packaging, and revenue growth. Before starting RevFixr, TJ spent a decade building and selling software, helping early-stage companies find customers, refine product-market fit, and navigate pricing decisions from small startup deals to multi-million-dollar enterprise contrac...

Rupert Mayer is the founder of IPfolio , a vertical SaaS platform built for corporate intellectual property teams to manage patents, trademarks, renewals, and innovation workflows. Originally from Austria, Rupert stumbled into IP software while helping a patent law firm solve Y2K risks, then moved to Silicon Valley to build a modern cloud-based product on Salesforce for smaller in-house IP teams....

Eric Ries is the entrepreneur and author of The Lean Startup , whose work helped software founders validate ideas faster and build companies without making huge bets upfront. After years helping startups, large companies, and governments apply Lean Startup principles, Eric built the Long-Term Stock Exchange and turned his attention to a bigger question: Why do so many successful companies lose the...

Marc Sanderson is the founder and CEO of INNERGY , but he didn't start as a software founder. After earning his MBA and searching for a company to buy, he and partner Walter Wilkie acquired a small architectural woodworking business in Minnesota in 1997. Running that business revealed a deep operational problem: there was no software built for how custom woodworking shops actually operated. So Mar...