#137: Her Amazing Story of 0-$30M ARR with No Outside Funding - Rebecca Shostak

Andrew Gazdecki is the founder and CEO of Acquire.com, a marketplace of buyers and sellers of smaller, profitable SaaS products with revenues between $100,000 and $5,000,000. Andrew sold his own software company and learned how little support and information was available to sell a software product for under $5-10 million in deal size. Acquire.com has helped over 2000 entrepreneurs sell their software products for a combined value of more than $500 million. Acquire offers additional support to help founders package, promote, negotiate, and close their transactions. Potential buyers are vetted for financial viability and identity confirmation before getting confidential details for any deal. In this episode, Andrew describes their typical seller and buyer profiles, the typical process for a founder to sell a small and profitable SaaS company, typical multiples of profit that financial buyers offer, and founder transition periods. Quote from Andrew Gazdecki, founder and CEO of Acquire.com "There are three buckets of active buyers on Acquire.com. The first is below $100,000 net profit. That's going to be an individual buyer looking for something with maybe a little bit of product market fit. They want to take the product, grow it a little bit, see what they can do from there. They're buying a very, very early startup. So some buyers will actually start small and then work their way up. "From $100,000 to $1 million in net profit in our middle range, the buyer will a blend of "micro PE firms" and holding companies that want to get their hands on a business where there's a lot more going on. And then a $1 million in profit and above is going to be for the more traditional private equity or strategic buyers." Links Andrew Gazdecki on LinkedIn Andrew Gazdecki on Twitter Acquire.com on LinkedIn Acquire.com website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

Seth Hassell and Clint Ethington are the co-founders of Genius Monkey, a programmatic ad tech platform with proven targeting, tracking, and attribution for optimized results. Seth and Clint were childhood friends who worked on many business ventures before launching Genius Monkey in 2009, leveraging their experience in digital ad technologies.  Genius Monkey grew steadily as a bootstrapped company, with the founders and team working hard for years to improve their platform, prove results to clients, recruit agencies, and grow their team. Most ad tech peers took VC funding and are no longer around, but Genius Monkey is still growing and getting more profitable every year.  In this episode, Seth and Clint talk about their unusual long-time partnership, the power of profits, competing with giants, building a strong company culture, and leveraging non-dilutive funding to grow faster. Quote from Seth Hassell and Clint Ethington, co-founders of Genius Monkey "Don't be afraid to fail with the smaller stuff. A lot of times, people don't take the chance of seeing, "What if we do it this way?" What happens? And all those little things that could become something big, they never pursue because they're comfortable with where they're at." "Fail fast. Try stuff out. If you see it's not working, shelf it and go to the next thing. Move on until you find that one that's doing better than where you're at right now. Then, I will put the determination and the motivation behind it to see it through. Clint and I tried through lots of things that just didn't work out."  "If it wasn't working, we were okay. We wouldn't say, "It's all over, close the doors." It wasn't like that. It was like, "Okay, we know that doesn't work. What's our next thing we're trying?" And we always had different ideas in the background." Links Genius Monkey on LinkedIn Genius Monkey website Cypress Growth Capital website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

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 successful add-on products for live chat, AI support, business intelligence, and workflows. The company has over 2200 customers, 110 employees, and now $20 million in revenue. Shalin plans to keep growing and leverage modern AI technology to become a much bigger company based on the disciplined product culture they have created. Quote from Shalin Jain, founder and CEO of HappyFox “I think software and its pricing need to be deflationary, just like hardware, where memory prices, hardware prices, and server prices have all been deflationary. But we are now going through a phase where software is actually getting more and more expensive. “With the advent of AI and automation, software will become cheaper and more usage-driven. So, the best survivors in that phase would be the efficiently run companies that have not bloated themselves by charging more today to have more employees and spend more on ads. “I believe software needs to get cheaper because it's getting cheaper to run software every day; it's getting cheaper to outsource to AI and build stuff with the help of AI as well. So software cost should not go up; it should go down.” Links Shalin Jain on LinkedIn HappyFox on LinkedIn HappyFox website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

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 in his industry. The company became profitable quickly as Brian focused on outbound selling with cold calls and savvy demos to busy compliance executives. They grew fast, were profitable in just over a year, and attracted attention from potential acquirers.  In June 2024, Financial Recovery Technologies, a fintech legal software company, acquired Skematic for an undisclosed amount, including some cash and incentives. Brian and his cofounder still run Skematic and enjoy being part of a bigger software company owned by a private family office that is highly aligned with their culture and values. Quote from Brian Kesselman, cofounder and CRO of Skematic "My co-founder Charles and I had worked at a number of PE-backed software companies. And we had our own opinions about what it's like to work at a PE-backed company." "The family office structure is very different from a private equity firm across the board. They're looking typically to build profitable cash-producing assets. And so that enables our team to think long-term, which benefits not only the founders and the people that are still participating in the upside of the business." "That also means that the clients will benefit because you are going to do things that will benefit the clients every step of the way, one year, two years, five years, 10 years. And that was paramount to us, given that we've grown up in this very niche industry and our reputations to us are pretty much everything we have." Links Brian Kesselman on LinkedIn Skematic on LinkedIn Skematic website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

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, driven by great product design, the email footer “viral loop,” and referrals from customers and influencers.  In this episode, Rebecca shares her insights on product design, their unlimited pricing model, working with her co-founder/CEO, Martha Bitar, why they haven’t taken outside funding, and where AI is showing usefulness in their products. Quote from Rebecca Shostack, co-founder of Flodesk “The reason you hire is never to solve a problem. You need to be sharp and figure out how to solve the problem on your own. Then, you hire people once you've proven something.  “When you want to hire someone to run your paid ads, for example, you first need to figure out the basics. Then, you can hire someone to come in to own that so they can scale that operation.  “But it doesn't work to hire someone to come in and figure out something that you can't figure out yourself. How can you hire someone to manage something you don't understand?” Links Rebecca Shostak on LinkedIn Flodesk on LinkedIn Flodesk website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

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 company, Strety.   Strety is a fast-growing SaaS business with a popular app for small businesses using the EOS® approach to manage their businesses. It has 10 employees, hundreds of customers and partners, and no outside funding. Brian brought back some of his previous team to build another sustainable and valuable software company. Links Brian Dosal on LinkedIn BrightGauge website Strety on LinkedIn Strety website Entrepreneurial Operating System (EOS) website Traction book by Gino Wickman Anything You Want book by Derek Sivers   The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

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 extending through an industry ecosystem serving new markets. We also talk about the impact of AI on established vertical SaaS players and how it’s both an opportunity and a thre Tidemark supports the global community of practical vertical SaaS founders by publishing their strategic growth frameworks, their annual Vertical SaaS Benchmarketing Report,  and they host the annual Vertical SaaS Collective Live conference for founders.  Quote from Dave Yuan, founder at Tidemark “Vertical SaaS founders should not be asleep with AI. You can wave it off, view it as a toy, and say that no one’s going to trust that outcome or use it. That may have been the case, but things are changing really quickly. “Lots of smart people are making it better every month, and you have a massive opportunity to improve it with your data and workflow. “Jump into it to control your destiny. Don’t get caught sleeping without AI in your product in a useful way.” Links Dave Yuan on LinkedIn Tidemark on LinkedIn Tidemark website Tidemark Vertical SaaS Knowledge Project  VSaaS Collective Live 2025 conference Vertical SaaS Benchmark Report 2024 The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.

Dori Yona is co-founder and CEO of SimpleClosure, a technology- and people-powered company that helps founders wind down and dissolve a startup or business that is no longer viable. Shutting down a business can be complicated, costly, and risky for founders. SimpleClosure manages the unique processes with automation and expert support.  SimpleClosure has helped tech startup founders wind down over 500 startups, businesses that closed or have gone through a sale of assets. It manages the important steps of a winddown, including legal, regulatory, employees, investors, intellectual property, customers, data, and more.  In this episode, Dori shares the key considerations for SaaS founders who have run out of VC funding or need to shut down their companies for other reasons.   Quote from Dori Yona, CEO of SimpleClosure “The biggest thing for software startup founders and CEOs is to move fast. Your time is your biggest resource in life as an entrepreneur, whether you’re venture-backed or bootstrapping. You’re spending your time,  you’re spending your energy, you’re spending the best years of your career. “So move fast, learn fast, test fast, iterate quickly, grow fast, fail fast. Ultimately, when you’re building your own business, you’re sacrificing an easy, convenient, cushy job anywhere else to take this risk. “The faster you can grow, learn, build, and fail, the better. It’s ultimately to your advantage to make the most of your time. Our time is our most expensive resource.” Links Dori Yona on LinkedIn SimpleClosure on LinkedIn SimpleClosure website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.

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.   Read-A-Thon was successfully acquired by private equity investors in early 2023 for an undisclosed amount. The business has continued to grow and expand with a new CEO and key executives, with Howard on the board as an advisor and now a minority investor in the company.  Quote from Howard Gottlieb, founder of Read-A-Thon “I have been very blessed and very lucky in my journey with the success of Read-A-Thon. Everyone should realize that and have some humility. “If you succeed at the game, you can be the smartest guy or the smartest woman with the most brilliant idea, but it still will take 50% or more luck for everything to align correctly to succeed. Just realize that. It takes a lot of good fortune. “At Read-A-Thon, our lucky moment was COVID because online fundraising was only in its infancy. When COVID hit and schools were out, Read-A-Thon was almost the only viable option. Our growth went from 40% a year to 100%, then 150% a year. So that was luck after all these years.” Links Howard Gottlieb on LinkedIn Read-A-Thon on LinkedIn Read-A-Thon website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.

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. From inception, through growth and ultimately acquisition, Richard never took any outside funding. FirmView adoption grew steadily, serving large private equity firms. PFA Solutions eventually grew to 34 employees before being acquired by Allvue Systems in 2024. Allvue is a private-equity-backed software company that serves the alternative investment industry. Quote from Richard Change, co-founder and CEO of PFA Solutions "Once you're in it, once you've decided to start a company, own it. No regrets. No one's going to save you. There's not a fairy godmother that will come and wave all your problems away. You have to own it. "There's no magic wand that will come and wave a wand and say, OK, all your problems are solved. And that magic wand in my mind wasn't outside capital; it wasn't VC funding. That wasn't magic because what do when the money runs out? "Is your product generating revenue? That's the real problem. If there's a problem to be solved and you have a great idea or solution, you can generate revenue from it. Prove to yourself and the world that this is viable and has product-market fit." Links PFA Solutions on LinkedIn PFA Solutions website Allvue Systems website Vista Equity Partners website Podcast Sponsor - Cypress Growth Capital This week’s podcast is sponsored by my friends at Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast. Message Cliff Sentell at Cypress to have an open discussion about your options.  The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.