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.
Shalin Jain is the founder and CEO of HappyFox, a successful bootstrapped company that provides modern help desk management software for customer service, support, and IT management organizations. Shalin and his small team in India built many successful products from 2000-2010, then focused on HappyFox and moved to the US in 2011. HappyFox is a mid-market product that sells across industries and departments with an efficient product-led growth (PLG) approach. The product has matured with success...
Brian Kesselman is cofounder and now CRO of Skematic , a compliance management and workflow software for financial services firms. Brian was a lawyer for major financial services companies who helped manage internal compliance in this highly regulated industry. He took a job selling compliance software and broke sales records before starting Skematic with a coworker and launching in September 2022. Skematic grew quickly by solving an acute problem for lawyers and compliance execs just like him i...
Rebecca Shostak is co-founder and chief brand officer of Flodesk , the popular email marketing software for small businesses that care about beautiful branded emails. After prototyping the product and validating the problem, they launched in 2019 with a viral explosion that still powers their bootstrapped growth. Six years later, Flodesk has over $30M in annual recurring revenues with 75 employees and over 100,000 paid customers. They have been profitable since the second week after launch, driv...
Brian Dosal was the founder and CEO of BrightGauge, a software company he bootstrapped and grew to almost $10M ARR with his brother before successfully selling the company in 2019. BrightGauge was a business analytics and dashboard for key metrics for the Managed Service Provider (MSP) industry. After his intense 9-year journey at BrightGauge, Brian “retired” to spend more time with his growing family. He enjoyed his free time but eventually returned to the software startup game with his second ...
Dave Yuan is the founder of Tidemark , an active growth equity investor focusing on vertical SaaS companies with outsized advantages that can become “control points” in their markets and grow very big. Dave and Tidemark have invested in successful companies like Toast, ServiceTitan, Karbon and Dutchie. In this episode, Dave shares some of the most useful strategic growth frameworks for vertical SaaS companies to grow through winning market share, expanding with additional products, and even exte...
Dori Yona of Simple Closure discusses the often-overlooked topic of startup shutdowns, highlighting the complexities and emotional challenges involved. She explains how Simple Closure streamlines the shutdown process, offering software and expert support to founders. The episode explores reasons for shutdowns, managing investor relations, and the importance of a well-managed closure for future opportunities.
Howard Gottlieb started Read-A-Thon in 2012 as a reading-based fundraising platform that helped students raise money while boosting education. Their easy platform and simple fundraising approach created amazing results. The Read-a-Thon business grew steadily and profitably without any outside funding. Read-A-Thon helped over 4000 schools and students raise over $30 million in donations. Their platform has tracked over 30 billion reading minutes by students who have used it to earn donations. Rea...
Richard Change is co-founder and CEO of PFA Solutions , the provider of FirmView software. FirmView® is the leading carry and compensation management platform for private equity investors to manage their internal compensation from fees and carried interest. Richard was a senior architect for a large private equity firm when he discovered this complex problem that was being managed on spreadsheets. He left to start PFA Solutions and bootstrapped the development of FirmView with consulting revenue...
Rachit Khator is the founder and CEO of Stackby, a no-code spreadsheet and database app builder that allows business users to create powerful spreadsheet-like applications with data links, automations, and workflows. Rachit and his team of 34 employees live in Surat, India, north of Mumbai. Stackby started when Rachit was working for a corporate venture firm in Michigan, doing repetitive manual data imports and analysis in Excel. He hired a developer to build a better tool and started to sell St...
Joe Hyrkin is the former CEO of Issuu, a content publishing platform for interactive marketing content. Issuu allows you to easily publish printable and PDF materials in various formats to websites and social media. It’s a global product-led success story with millions of customers and a successful and sustainable business. Issuu was started by four Danish founders before the company was moved to Silicon Valley in 2013 when Joe was hired as the CEO. Joe ran the company for almost 12 years, growi...
Brian Hamilton is one of America’s most successful entrepreneurs and a leading expert on entrepreneurship. Today, Hamilton serves as chairman of software company LiveSwitch . He is known for his pioneering work in fintech, his advocacy for small businesses, and his commitment to criminal justice reform. As the founder of Sageworks (now Abrigo), America’s first fintech company, Hamilton developed technology that translates complex financial data, empowering millions of small business owners. Sage...
Scott Desgrosseilliers is the founder and CEO of Wicked Reports , a leading multi-touch marketing attribution software for SMBs who use paid online advertising. Scott is a data and analytics expert who saw the costly limitations of simple performance reports from popular ad platforms. Wicked Reports was started as a bootstrapped software company in 2016 to serve smaller companies that spend millions on digital ads and other marketing, including email, SEO, and digital events. Determining which m...
Bryan Forrester is CEO of Boostlingo, a leading on-demand platform for language live interpretation services that is growing quickly and can become a very large company. Boostlingo now has 160 employees and over 17,000 language interpreters who use their software to manage jobs, coordinate schedules, deliver interpreting services, and get paid. Bryan raised some practical funds from angels to start the company in 2016. The company grew 50% or more every year since then. In 2021, Boostlingo raise...
Jason Fried is the co-founder and CEO of 37signals, makers of the popular Basecamp project management software, which is still growing and very profitable after 20 years. He is going long and still having fun as an engaged CEO, building great products with great marketing that stands out. Jason has long advocated for software founders to avoid VC funding and build sustainable businesses that are great for customers and generate healthy profits for the owners. His best-selling book, Rework , shar...
Quote from Russ Perry, founder and CEO of Design Pickle “The game for practical SaaS founders really comes down to recognizing that there is a large market size for very boring niche companies. Finding that niche is the fastest path to success. Don’t be afraid to be boring and specific. “If I were to do Design Pickle all over again, I would have just picked a vertical niche, like we are the graphic design provider for feline mobile cutting trucks or something. There are easily 10,000 mobile pet ...
Sunando Bhattacharya spent 13 years as a business leader in managed IT services companies in India before starting his own cloud tech services business. This company grew slowly and an opportunity arose to create a software product for one of their clients. Two years later, in 2019, they had a few more Apiculus product customers and focused more on the product. Apiculus is a complete "cloud-as-a-service" software platform for data centers to offer, sell, deploy, and manage cloud data services fo...
Steve Wolfe and Nate Grossman are co-founders at Growth Street Partners , a growth equity firm focused on investing in early-stage B2B SaaS companies between $2M-$6M in ARR. They discuss how growth equity funding works for SaaS founders and how it allows entrepreneurs to maintain control while still benefiting from investment and liquidity. In this expert episode, Steve and Nate get specific and share real examples of how SaaS founders use growth equity to win bigger, when it can be a good fit f...
Raj Bhaskar is a successful two-time practical software founder with one exit. In 2000, he started his first software company, VisualHOMES, to provide a comprehensive financial management software to public housing agencies. With no outside funding, the business grew to serve 65 regional providers serving 2 million residents before Yardi Systems acquired the company in 2010. After he left Yardi two years later, Raj and his brother launched Hurdlr to reach the wider small business market with a s...
Vince Hsieh is a two-time entrepreneur who has started, grown, and sold two industrial tech companies that included software and either an RFID or GPS device in the solutions. His second venture, Geoforce, raised a non-dilutive funding round to accelerate global growth before being successfully acquired by private equity investors LLR Partners in 2019. Their royalty-based funding round allowed Geoforce to skip a VC funding round, preserving founder equity and fueling their growth. After their ac...
Bill Spruill had a successful sales and executive career with two exits before he and his cofounder struck out on their own in the location verification market serving financial and e-commerce companies. Sales grew slowly for several years as they scraped by and kept going. Eventually, they pivoted the company to focus on identity verification and know-your-customer (KYC) with a new approach, and sales grew steadily every month. Global Data Consortium (GDC) partnered with data providers and fint...
Troy Munson has been a successful enterprise SaaS sales rep for several years, but he wanted more control over his life—and eventual financial independence. So he launched his own small startup on the side. He learned a lot and sold it before launching his second side gig software company, which he sold for a little bit more. He started his third side-gig startup, Dimmo , in 2023 to allow enterprise software buyers to watch product demos without talking to sales reps. With the help of co-founder...
Wes Bush is CEO of ProductLed , a coaching and education company that has helped almost 500 serious SaaS founders to succeed with product-led growth strategies, tactics, and execution. These include freemium products and free trials, where the product itself creates the awareness, engagement, and enthusiasm to buy before any human intervention (aka “the required sales demo”). Wes has written two successful books, Product-Led Growth and The Product-Led Playbook , describing key ideas, frameworks,...
Michael McAllister is the founder and former CEO of The CE Shop , the leading provider of pre-licensing and continuing education for real estate professionals in the U.S. Michael started The CE Shop in 2005 by distributing existing training materials from a continuing education provider. They quickly created their own online education solution and proceeded to expand with specific content and compliance elements for each state. The CE Shop grew steadily without outside funding for 15 years by bu...
Last year I interviewed three-time software founder Matt Watson on this podcast about his successful practical founder journeys. Matt leveraged offshore software development talent in his last two SaaS companies to staff up quickly and grow efficiently. His top developers and designers were offshore in the Philippines, but they weren’t one-off contractors or difficult-to-manage outsourced agencies. He found an endless supply of top tech talent who became savvy members of his team, working hard e...
Eric Dill was a successful mortgage broker in Sydney, Australia, who struggled with the same painful problem as every other broker: manually checking with multiple banks to validate and price mortgages for homeowners. Eric and his good friend Angus Keatinge resolved to create a software product to solve this complicated and chronic problem. Quickli was launched in late 2021 and it immediately gained happy customers and fans without any proactive marketing or sales. Three years later, more than 1...
Guy Rubin is the co-founder and CEO of ebsta , a revenue intelligence platform that works with Salesforce and Hubspot to automatically analyze existing data to improve sales performance. Started in London in 2012, ebsta found success in the early days of the Salesforce marketplace and addon economy as a data tool integrated with customer emails. ebsta has since become a complete revenue intelligence platform, serving sales teams with 10-100 sales reps. With 400 customers, 30 employees, and no VC...
Stuart Draper founded Stukent , an innovative ed-tech company that provides simulated internships for business students. Stukent started by focusing on high-quality digital marketing education for colleges and universities using up-to-date digital textbooks and content. They then added a simulation system for students to practice their digital marketing skills. Stukent grew steadily with less than $1M in outside funding, which helped them bridge the long and seasonal buying cycles of big schools...
John Stewart created and sold an engineering services business, then grew a Salesforce integration services company before building some early software products. One of their software experiments allowed Salesforce customers to see and interact with their customer data on a map. When customers paid for it and revenue grew, he and his co-founder wound down services and focused on their mapping product. MapAnything grew quickly to over $2M ARR as a bootstrapped software company, with some revenue-...
Landon Taylor created two successful digital marketing services businesses before starting a product-powered business with recurring revenues. His first agency drove traffic to its customers, which led to his second business, Best Company, which produced qualified leads for large home services businesses through its bestcompany.com consumer review site. Their work in consumer reviews led them to his latest business, Snoball , a word-of-mouth marketing platform they use to predictably and efficie...
Kyle York was the Chief Revenue Officer of Dyn, a bootstrapped cloud infrastructure that he helped grow and sell to Oracle for over $600 million. He then led product strategy and acquisitions in Oracle’s cloud infrastructure group before going out on his own to invest in SaaS startups and help them grow. York IE is both an advisory firm with tech-enabled services to help early-stage B2B SaaS companies grow and an investment firm that has invested in over 60 practical SaaS companies. In this expe...
