Practical Founders Podcast

Thomas Brown creatively bootstrapped his software company and ran it as a very small "lifestyle" business before committing to growing his SaaS business with a larger team. Thomas was an independent insurance claims adjuster in the 1990s in New Orleans, Louisiana before quitting his job to start one of the first insurance claims management software companies called ClickClaims. It grew slowly and profitably as a very small company for over 10 years before Thomas sought help from advisors to see how he could grow to the next level and learn to be a real CEO of a bigger SaaS company. E-Claim is now a steadily growing vertical SaaS business with 18 employees and over $4 million in ARR. They have helped independent insurance adjusters and insurance carriers process over 2 million claims with their ClickClaims product since he started the company in 1999. "I know this sounds cliche, but I didn't get into this for the money. I got into it because I'm a guy from South Louisiana who's been through a bunch of hurricanes and knows the horrors that people go through. And I wanted to make it better. So you reach a point in the business where you start to think about not what it means for you, but what it means for others. What can you do for your employees and their careers? What other charities can I go and support with this money someday? And then you think about it, and you say, you know, hell, I want to double it, because I could do a lot of good with a lot more money." In this episode, Thomas explains: How he started his company and built a software solution after experiencing a massive industry problem himself How he grew a $4M+ ARR SaaS company without funding with just 50 customers Which creative side businesses he started to generate enough cash to build and start his software company How trusted business advisors helped him gain the knowledge and the confidence to be the SaaS CEO and team leader required to keep growing his company Why he is inspired to make a bigger impact with his employees and in his community by continuing to grow his business

Nick Santora bootstrapped Curricula for 4 years with his co-founders before raising $3M in practical funding and then getting acquired in 2022 for $22 million. Nick and his co-founders quit their jobs to build innovative story-based education courses and a single-purpose learning platform for cybersecurity security awareness training. Nick had found a big hole in the cybersecurity market while working as a cybersecurity trainer in the electric utility industry. Curricula features fun and engaging training content, which was the opposite of the typical "death by Powerpoint" training that users ignored. Now Curricula is a powerful platform that allows companies to create their own engaging content and then measure custom training results. When they almost ran out of cash before revenues grew, Nick says. "I would do anything I could do to keep this heartbeat going instead of getting an investor to run our future. Once that starts happening, I knew it was going to start cascading into desperation. And I wanted to hold the cards in our hands as long as we could." In this episode, Nick explains: How he saw this problem as a cybersecurity trainer in the electric utility industry How he and his cofounders quit their jobs to build this platform while living on savings and no salary What happened when they ran out of money three times while pivoting and experimenting to find their growth path How they used freemium PLG tactics to compete with an aggressive competitor who had raised $80 million in VC funding How his last-ditch promotion test with LinkedIn advertising created their primary efficient customer acquisition tactic Why he didn't raise money from VCs but instead raised from a practical investor who had grown and sold a bootstrapped company Check out all our podcast episodes at https://practicalfounders.com.

Jeremy Clarke created, grew, and sold his software company in a most unusual and successful way: He grew WebMerge to $4M revenue by just himself in 6 years before hiring his first and only employee, a strategic sales rep. It's an incredible "bootstrapped unicorn" success story that ultimately was worth $100M when he sold WebMerge in 2019. WebMerge was an online service that automates document creation to automatically fill in any documents with merged data from any source. WebMerge automatically generates PDF and Microsoft Word documents. Think of it as "mail merge for the web." Jeremy's first employer, Formstack, ultimately acquired WebMerge to bring Jeremy back to the Formstack team and renamed the product to Formstack Documents. In this episode, Jeremy explains: How he came up with the idea and pitched it to his employer before building it on his own How he grew revenues to $1M ARR before he quit his day job as a full-time software programmer What it was like to grow a $5M+ ARR SaaS business without any other employees or Slack groups or constant meetings How many years in a row he raised prices before he found the right price How he grew awareness and conversion efficiently by integrating with other apps and appearing in their add-on marketplaces What it was like to sell his company to a private equity (PE) buyer in two phases Check out all our episodes and articles at https://practicalfounders.com.

Luke Hohmann was an engineering and product management leader at Silicon Valley startups before he became an acclaimed author and speaker in the enterprise software development world. He used funding from his consulting business—plus revenue from his first big customers—to build a new software product called Conteneo. Conteneo was enterprise collaboration software that enabled the biggest companies to engage their leaders in new ways to make much better decisions about product portfolio investments. Started in 2010, this idea came out of several of the gamified collaboration exercises Luke used in his consulting business. Conteneo software customers include Adobe Systems, Cisco, Emerson, HP, Rackspace, and Reed Elsevier. As the Conteneo software business grew, their consulting business shrank. Eventually, Conteneo was acquired by a strategic partner who was also a leader in enterprise software development and innovation, Scaled Agile. Conteneo was rebranded as SAFe Collaborate. "One of the important lessons for any practical founder is this: Instead of thinking of investors as your first source of funding, look to your first customers," Luke says. In this episode, Luke explains: How his biggest consulting client asked him to build their proven collaboration process into a SaaS software product. How he funded the initial development and subsequent features with creative customer contract commitments. Why his little, bootstrapped company was successful in selling to the largest software companies in the world in the heart of Silicon Valley. The bet he won with a funded founder friend about who would end up with the biggest prize when they sold their companies. The crazy story of how a well-known business author offered to invest in his company over a handshake at a conference. Why he thinks founders should have a structured advisory board and pay them instead of just having informal advisors. Check out all our episodes and articles at https://practicalfounders.com.

Steve Gelley created two successful businesses and learned important lessons before he and a cofounder self-funded a third startup that was acquired in only 18 months for a big prize. Steve started his entrepreneurial journey by buying, improving, and then selling CPA accounting services firms in the Eastern U.S. Then he grew his first VC-funded tech startup, Xendoo, to innovate in the small business accounting services space. He exited Xendoo and worked with a partner to fund and create a new startup called wemlo to automate the manual process of processing mortgage loans for mortgage brokers. Only 18 months from starting, including four strategic pivots, Steve and his cofounder, David Rogove, sold wemlo to a strategic buyer owned by RE/MAX. Steve says, "Nobody tells you that founders end up spending so much time on funding and the optics of the dog and pony show that no one's running the business. It's actually counterproductive." In this episode, Steve explains: Why he sold his interest in his first startup when the company achieved its first VC funding How he and his cofounder built a market-leading solution for a massive industry with a small team What the true opportunity cost of raising VC funding is for founders growing vertical software companies The simple math that showed him raising big funding would not be better for the founders What it takes to design revolutionary software with automated processes that revolutions Why he says "timing is the luck factor in a business," especially when you exit a business Why money from investors won't solve all your problems and often make things worse Check out all our episodes and articles at https://practicalfounders.com.

Hamid Shojaee is a technical founder and serial entrepreneur who created several software companies and dozens of products in the last 25 years. He sold his two software companies in 2021—Axosoft and Pure Chat—and now is an active investor and has a new startup to keep him busy. Axosoft was popular project management and bug-tracking software for developers that he bootstrapped to launch in 2002. It grew profitably for years until it met stiff competition despite active efforts to grow. Dozens of product experiments finally produced a hit, the popular software GitKraken. In this episode, Hamid shares some hard lessons learned: How he and his team experimented to test new product ideas and don't invest until they prove real user traction (DAUs) The challenges of raising money from investors who want faster revenue traction too early in the product-led growth cycle The challenges of not being the dominant leader in your market in the long-run Selling one business to a strategic buyer without help: selling the other business to a financial buyer using M&A investment bankers The modest changes in his life after selling two companies for life-changing wealth in 2021 Why he's starting and building another software company Check out all our episodes and articles at https://practicalfounders.com.

Dan Jaffe is the founder and CEO of LawLytics, a popular website marketing platform for small law firms. Dan was a practicing lawyer before he became an internet entrepreneur with his first venture, which he sold before he started LawLytics in 2012. LawLytics was acquired by the Australia-based Smokeball-LEAP-InfoTrack Group in 2021. Dan is still growing LawLytics as its leader of the acquired company. LawLytics is a website platform for small law firms who want a successful website but don't want to overpay an agency or struggle with software that isn't built for them. LawLytics has templates, designs, and lead-generation tools specifically designed for lawyers to generate business efficiently. In this episode, you'll hear how Dan: Transitioned from being a practicing trial attorney to an internet entrepreneur and SaaS founder Created and sold his first business, an online law firm directory Self-funded LawLytics then added small investments from angels and a local seed fund Found a technical co-founder by networking in San Francisco Competed with bigger competitors to deliver a successful website marketing platform for attorneys Grew to over 30 employees and contractors, then successfully sold the business in 2021 with the help of an M&A investment banking firm Check out all our episodes and articles at https://practicalfounders.com.

Rafael Zimberoff was CEO of ShipRush, a software company he founded in 2001, then grew, and eventually sold in 2017 to Descartes Systems Group for $17 million. Rafael started ShipRush as an add-on product for popular CRM and accounting software and was a pioneer in shipping technology for small businesses. ShipRush is now a comprehensive shipping platform for small ecommerce providers so they can easily process shipment orders and carrier labels for USPS, Fedex, and UPS. ShipRush integrates with popular ecommerce and accounting platforms, including Shopify, Amazon, eBay, Quickbooks, and more. In this episode, you'll hear how Rafael: Boostrapped his tech services company to fund their first software product then grew without outside investors Created a popular add-on software product for bigger software ecosystems as an efficient way to find customers and grow revenues quickly Managed complexities of being an early pioneer in shipping technology working with large carriers like Fedex, USPS, and UPS Ran a profitable software company for more than 15 years with a small and amazing team Learn hard lessons then succeeded in working with M&A investment bankers to sell his company Check out all our episodes, articles, and resources at https://practicalfounders.com.

Jonathan Cronstedt, also known as JCron, was the president of Kajabi software from 2016 through 2021 as he helped the company grow past the early startup years. JCron is a savvy entrepreneur, digital marketer, and sales leader who shares the story of the bootstrap founding of Kajabi through getting $550M in venture capital funding in 2021. Kajabi is a leading "knowledge commerce" platform for experts and entrepreneurs to market and sell their expertise as online content. Started in 2010 to help early internet marketers and small business experts deliver videos and training, Kajabi has helped over 30,000 creators to sell their expertise and expand their businesses. In this episode, you'll hear how Kajabi: Had $1M+ annual recurring revenue the moment the product launched after coding on nights and weekends for a year to create the first product Founder and CEO Kenny Rueter grew revenues ahead of expenses to stay profitable from day 1 to over $50M in revenue 10 years later Grew as a modest software business for the first 5 years, then rebuilt the product to grow the business much bigger as the market eventually grew up in the next 5 years Kept a fanatic focus on their target customer (called "Kajabi heroes"), a powerful and easy-to-use product, and a well-defined culture More than doubled in size in 12 months during the COVID crisis when online courses and content became a global focus Waited 10 years to take any outside investment in 2020 that helped bring the expertise to scale, then raised $550M at a $2B valuation from VC investors in 2021. Check out all our episodes, articles, and resources at https://practicalfounders.com.

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 2006 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 small revenue from the small customer base and his own savings allowed them to rewrite Showit for the cloud and then continue their fanatic customer focus to keep growing every year. Now Showit is used by 35,000 designers, photographers, and small businesses as their website platform using its elegant "Photoshop-like" no-code visual builder. The Showit company is growing quickly every year and is profitable, yet Todd has no interest in taking outside funding or selling his beloved company. In this episode, you'll hear how Todd and the Showit team: Spun off Showit from a small software company, then rewrote the software from old Flash technology to new cloud software Serve and love their customers to create a fanatically loyal community that is expanding quickly without expensive marketing Recruit, engage, and empower their employees in creative ways that no funded software company ever would Never think about external funding or selling the company despite the company's extraordinary value and potential Started with a fanatic niche focus on an underserved community and then expanded its market as the community grew Check out all our episodes, articles, and resources at https://practicalfounders.com.