Practical Founders Podcast

Karl Swannie was a geographer working in the scenic city of Victoria, British Columbia, Canada, when he started analyzing social media data based on location. He quickly saw there was valuable real-time information that was not being used, so he started Echosec Systems to find a practical use for those insights. After several years of experiments and hard startup lessons learned, Echosec finally shifted from being an inexpensive news/insights tool to a comprehensive threat intelligence platform for large organizations. Echosec Systems is now a leading open-source intelligence service (OSINT) that uses publicly available information (PAI) from social media and other sources. They help public and private organizations improve situational awareness and identify threats using geographic insights with real-time data. Echosec was partially sold to a "search fund" called The Tusker Fund in 2020 and Jeff Oldenburg came in as CEO to scale the company, which he did. In 2022, Flashpoint acquired Echosec completely and the business continues to grow. In this episode, Karl explains: How they started as an inexpensive B2C solution and then pivoted to large B2B deals with big organizations What it's like to be a Canadian software company selling a threat detection service to large organizations around the world How they finally started to scale when they focused on the largest customers with the biggest needs How he worked with a private investor to start the company but used venture debt to grow it when they were profitable What a "search fund" is and why this was a great fit to partially acquire the company and bring in an experienced CEO What it was like to sell the company and not be the CEO-in-charge any more What he learned about himself in this journey that he is applying to his next venture Find out more at practicalfounders.com. 

Brad Redding, previous startup founder and successful CEO of a scaling SaaS company, talks about his experience with his first startup and the important lessons he learned. He then discusses the challenges of finding product-market fit and growing a profitable SaaS business. Brad emphasizes the value of investing in himself and his leaders for personal and professional growth. He also shares insights on the importance of data tracking, customer validation, and building a global team. Overall, the podcast highlights Brad's journey from a scrappy startup founder to a scaling-up SaaS CEO.

Daniel Yuabov, a scrappy startup founder, revolutionized the car buying experience with his company Carvoy. He shares his journey of quitting his job to build an online solution for car buyers. After various pivots and experiments, they found success by automating every step of the car buying process. They shifted from a marketplace to selling as a SaaS product to dealers. Eventually, Carvoy was acquired by a major car-financing lender. Listen to hear Daniel's inspiring journey and practical advice for fellow founders.

Melissa Kwan, founder of a software business, shares her experiences in starting and growing her companies. She discusses the challenges of the real estate market, the concept of a lifestyle business, and the power of defining personal success. She also talks about funding, growth, and balancing work and life in software companies.

Seth Radman created, grew, and sold two music app startups in his twenties. A saxophone player in his college marching band, Seth was passionate about helping musicians and school band directors to improve how they learn music using technology. Seth was the founder and CEO of Crescendo, an interactive music trainer that provides real-time performance assessment feedback using acoustic pitch detection and machine learning as a mobile app. With a little angel funding, Crescendo grew to over 1M users and 7,000 schools before being acquired by Ultimate Guitar in 2018. He was also co-founder and CEO of Upbeat, a bootstrapped startup providing a virtual music collaboration platform for school music departments. When schools shut down during COVID, Upbeat allowed musicians to rehearse and perform music virtually with others in real-time without sound delays. Upbeat grew to over  200,000 users in 12 months and was purchased by 5,000 schools before being acquired in 2021 by MakeMusic. "Having a company acquired seemed like this big elusive goal that every founder wants to achieve. And then I did it. And then I wasn't sure what to do next at all, I was completely shocked on the first day," Seth says.  "I say it was one of the happiest days of my life when I saw the money hit the bank. And then the day after, that was probably one of the most depressing days of my life, because I was like, whoa, what do I do now? I definitely thought there was a little bit of loss of identity for me going through that. "And I spent the next several months kind of doing nothing. I was honestly just depressed. I just felt super lost and was not sure what to do. And that was a really tough period. " In this episode, Seth explains: How he had hundreds of product ideas, did hundreds of customer interviews, and ran dozens of experiments to eventually find problems that customers would actually pay to solve What product-market fit really means to him and why it's so important to experiment before you invest lots of time and money Why he felt that he wasn't the right person to scale up his first company and the deep anxiety he felt when he successfully sold it How he's managing the emotional ups and downs of being an entrepreneur now after experiencing mental health challenges How he leveraged an existing customer base and channel to rapidly grow his second startup as COVID lockdowns created an acute problem in the music teaching industry How he developed a strong persistence habit as a musician that helped him do hard things every day that he didn't want to do

Dougal Cameron created Golden Section to provide support and practical funding to SaaS founders with deep experience in select vertical markets. Their founder-first approach is different than the traditional VC or private equity investment model which often doesn't work out well for founders in the end. Dougal's family had been investing in software companies for over 20 years through their Houston-based family office. Now Golden Section includes a founders studio for venture development, a world-class software product development service, and optional equity funding for B2B SaaS founders with deep domain experience in their industries. This is an example of one of many possible ways that funding can be practical and helpful for founders who want to accelerate growth but don't want to play the unicorn-hunting grow-or-die game required by most venture capital investors. "Our capital needs to look very different than the traditional venture capital side, where 66% of the time venture-backed founders make nothing when their company sells. And that's companies that get to an exit," says Dougal. "I think that's a horrible statistic that really reveals some of the problems in the venture capital industry. It doesn't make a ton of sense for founders who see a clear problem that they know very well and they know people are going to buy their solution." In this episode, Dougal explains: Why traditional venture capital investment is not a good fit for certain kinds of software businesses The hard lessons he has learned from years of investing in software companies and running software companies himself How they have designed their investment model to support founder-friendly exits where everyone can win: founders, investors, employees, vendors, and customers How they provide deep support for the founders they partner with, including software development services, growth advisory, and execution advice in every aspect of the company What Golden Section does to support the brutally hard emotional journey that all founders go through as they grow their companies Find the show notes for this episode at practicalfounders.com. 

Sean Meister was a sales professional and leader with a successful career selling hospital and medical supplies before he left to join his long-time friend who had a vision for a new software company serving smaller trucking fleets with simple GPS-tracking fleet management software. Sean was a co-founder and COO of M2M in Motion, a self-funded software company based in the Chicago area. Sean wasn't the trucking industry expert, the crazy entrepreneur, or the visionary salesperson. He provided the savvy help to get the company started and the operational leadership to build a scalable sales team, reliable product development, and quality customer operations. M2M in Motion was bootstrapped with founder funding, then customer funding (revenue), to grow to over $5M in revenues before being acquired in 2021 by a larger vehicle telematics company, AAMP Global. M2M in Motion allowed small and mid-sized fleets to track their vehicles with a simple software solution and GPS-tracking devices. "I think another reason we were successful is that we identified our ideal customer profile early, and we owned it, and then we really targeted that. In the beginning, you're just so desperate for anything, that you don't realize you're actually hurting yourself," Sean says. "I think that was a big lesson for us. When you can start saying NO is when your trajectory starts taking off." In this episode, Sean explains: Why he quit his successful sales career to join his long-time friend who had an idea for a software startup in the transportation technology industry How long it took to get to breakeven revenue after spending their personal savings to get the company started How the US "ELD" government trucking safety mandate helped them grow fast How they introduced device financing to bundle the GPS-tracking hardware and software for a simple monthly fee How they successfully competed in a very active, well-funded industry as a small, bootstrapped company by keeping things simple and narrowing their focus How their multi-channel growth strategy included "white-labeling" their software to strategic reseller partners and how one of those relationships led to their acquisition Check out the show notes and links for this episode at practicalfounders.com. 

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.