

Practical Founders Podcast
Greg Head
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.
Episodes
Mentioned books

Nov 11, 2022 • 57min
#20: Grew on-demand marketplace out of a search marketing agency – Joe Griffin
Joe Griffin recently left his job of 8 years as co-CEO of ClearVoice, a company that he and co-founder Jay Swanson started in 2014 out of their digital marketing agency business in Phoenix, Arizona. ClearVoice was acquired by Fiverr in 2019 and has been operating as an independent subsidiary since then. Fiverr is now a large public company with a global reach. ClearVoice was created in the fast-changing web search marketing industry in 2014 out of the need from larger companies for high-quality content to drive their organic website traffic. Joe and Jay previously ran their search marketing agency iAcquire and used profits to self-fund the first ClearVoice platform. They eventually raised a small amount of practical outside funding, including a seed funding round of $1.5M and venture debt of $2M. ClearVoice is now a leading platform for brands to hire industry-savvy experts to write useful content that is branded for their communities and customers. Thousands of brands and over 10,000 industry specialist creators use ClearVoice to drive organic marketing efforts with high-quality content. In this episode, Joe explains: How he had created and sold previous internet marketing agencies and technologies before creating ClearVoice The difficult transition of creating and funding the ClearVoice marketplace out of an existing services business The acquisition by Fiverr before they went public in 2019 and how they operated as an independent subsidiary after that Their practical funding with self-funding from their services business, a little angel funding, a small $1.5M seed investment round, and then venture debt before being acquired How he led ClearVoice with a co-CEO and how they worked on all big decisions together Find all the episodes and resources at practicalfounders.com.

Oct 28, 2022 • 51min
#19: Practical VC seed investor explains the institutional funding game – John Francis
John Francis is a general partner at Stout Street Capital, a venture capital fund based in Denver, Colorado. Stout Street has made 70 small seed and pre-seed investments in software startups outside the big tech centers in North America. Unlike big Silicon Valley VCs, almost half of Stout Street's investments are in practical startups that have reasonable valuations, sustainable growth models, and won't need more outside investment before they exit. In this in-depth interview with a "practical funder," John explains the ROI math of professional venture investors and reveals how they think about investing. John also has great insights on how founders should think about raising money, or not, in the first place. In this episode, John explains: The basic investment math that a seed-stage venture fund manager needs to deliver the expected return to their "limited partner" investors What kind of investment valuation and eventual exit outcomes are required to raise institutional capital When a practical founder shouldn't raise VC funding and how they should be thinking about taking outside investment capital How "practical VC investing" is different than traditional moonshot VC investing and why founders need to be clear about which kind of funding they want What's happening in valuation for investment and acquisitions in 2022 compared to 2021 Find all the Practical Founders Podcast episodes at practicalfounders.com.

Oct 21, 2022 • 52min
#18: Bootstrapped a podcast recording platform to scale in Silicon Valley - Zach Moreno
Zach Moreno, CEO and CTO of Squadcast, a podcast recording platform, discusses their journey from idea to 10,000 customers. He talks about the importance of timing and technological advancements, their participation in bootstrapped accelerator TinySeed, and their approach to learning and experimentation.

Oct 14, 2022 • 50min
#17: Creatively grew and sold a threat intelligence product with practical funding - Karl Swannie
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.

Oct 7, 2022 • 50min
#16: Growing from scrappy startup founder to scaling-up SaaS CEO - Brad Redding
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.

Sep 30, 2022 • 50min
#15: Scrappy startup founder changes the way cars are bought online - Daniel Yuabov
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.

Sep 23, 2022 • 52min
#14: Created her second software company around her world-traveling life - Melissa Kwan
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.

Sep 16, 2022 • 1h 1min
#13: Founder with 2 exits shares how he achieved real product-market fit twice - Seth Radman
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

Sep 9, 2022 • 55min
#12: Practical investor provides savvy help for vertical SaaS founders – Dougal Cameron
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.

Sep 2, 2022 • 51min
#11 - Bootstrapped to exit in 6 years against funded competitors - Sean Meister
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.


