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-founders, Dimmo is now live and revenues are growing fast. With a little angel funding, Troy was able to go full-time to make Dimmo successful quickly.

Troy is a fast-start SaaS founder, testing ideas and launching companies when traction starts. He and his cofounders don’t think about running this forever, but they do want to create a valuable company and achieve financial independence as successful practical founders.

Quote from Troy Munson, CEO of Dimmo

"I'm like this fast-starter person. I built Vocul and Refurl, my first two side gigs, from an immediate thought: This is annoying, this should be solved. Let me solve it, let me sell it. And then let me see if there's any interest.

"With Dimmo, I just wanted to create extra income on the side. The hope for Dimmo was to pay my mortgage with a side gig. I knew software buyers just wanted to watch software demos. So let's just make it like a YouTube for software demos and then we'll just take some sort of revenue.

"It blew up on LinkedIn when we launched and grew faster than expected. I had to go full-time and I'm so happy I did. It feels great. I hope I never go back to the side gig guy. I also hope I never go back to any sort of any sort of W-2 work. I'm buying my freedom."

• Troy Munson on LinkedIn
• Dimmo on LinkedIn
• Dimmo.ai website

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.

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.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

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, approaches, and examples for SaaS founders. In this expert episode, Wes shares his expertise for SaaS founders, including these topics:

• Defining product-led growth
• Transitioning from sales-led to product-led
• Common mistakes in product-led growth
• Identifying challenges and solutions for user experience
• Pricing strategies in product-led growth
• The future of product-led growth in SaaS

Quote from Wes Bush, CEO of ProductLed

“The PLG model you choose doesn’t matter. Not a bit. Freemium, free trial, credit card up front, whatever. You can make any of those work. That’s not the question. What matters in PLG is the actual outcome that we hope somebody will get from our product-led experience?

“Does your free motion actually have a transformation in it where they can feel they will grow bigger, save time, and do cool stuff? Because if you don’t have that, it’s literally just, “Hey, look around, see for yourself, see what you can do in this product. That’s not real value.”

“What is your PLG outcome that creates that transformation for the user? There has to be tangible value for the user before they ever consider buying. That’s what customers want when they buy software now–Show me value first before I think about buying from you.”

• Wes Bush on LinkedIn
• ProductLed on LinkedIn
• ProductLed website
• Free Product-Led Growth book
• Free Product-Led Growth audio book
• The Product-Led Playbook book

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.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

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 building a 5-star team, adding partner channels, expanding to new states, and providing more content for the pre-licensing of new real estate agents. The company grew to over 130 employees and expanded faster during COVID.

Michael successfully sold the company to private equity investors in 2020 for a “9-figure exit,” meaning more than $100 million, to Waud Capital. On this podcast, Michael shares the realities of their growth journey, including their special emphasis on culture, people, and practical expansion as a bootstrapped technology business.

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.

Quote from Michael McAllister, Founder of the CE Shop

“When founders sell their companies, I'd suggest they need to do it when they hold all the cards. During our first experience with a serious potential buyer, we asked for a lot of information about their business. It was reverse due diligence since I’d be the biggest private investor in their company.

“We were two weeks before closing, and I called our banker and said, this is really frustrating that we’re asking for all this information and not getting it back. Unless we do, we may need to pull the plug on this deal. We held all the cards. We had a great business. We didn’t need to sell like we were completely in the driver’s seat.

“It was really difficult but we decided to pull the plug on the deal. The biggest thing was that there was a real mismatch in core values. Our core values were foundational to who we were and who we are as a company. One of them was doing what we said we’d do. And it was a $100 million question. It was a big deal.“

• Michael McAllister on LinkedIn
• The CE Shop on LinkedIn
• The CE Shop website
• Waud Capital website (acquirer)

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.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

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 every day to get things done fast.

So, for his fourth venture, Matt created Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who augment and extend your core dev team.

In this expert session with a Practical Founders Podcast sponsor, Matt shares what works and doesn’t work for practical SaaS founders who want to offshore some or all of their software development.

• Matt Watson on LinkedIn
• Full Scale on LinkedIn
• Full Scale website
• Startup Hustle podcast
• Product Driven video channel

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.

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 funding, ebsta competes with a focused approach to play in the massive Salesforce ecosystem and against huge competitors.

Guy talks about their many pivots, running the business with his wife as cofounder, and the benefits and challenges of not being in San Francisco with VC funding. With deep data across thousands of sales reps, ebsta publishes an annual ebsta Sales Benchmark Report with specific data about close rates, quota attainment, and data-driven factors to improve sales performance.

This week’s podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io.

Quote from Guy Rubin, CEO of ebsta

“We found ourselves in a place where we had some amazingly talented, very driven, very focused doers, and they were happy to work together as a common goal and get stuff done.

“What moved the bar for me as the CEO was bringing on board advisors. I’ve now got four board advisors and a chairman sitting around me. We also brought on a CTO, CPO, and CFO, who are very experienced.

“So bring in those experts around you, people independent of those doing the doing. Don’t get me wrong; you need the doers. They’re absolutely vital, but I also needed experts to help me at the running stage.

“That was the best thing I ever did: bringing those expert advisors in. And if you’re small, I would encourage founders to ask different people to be advisors to give you an outside perspective. You’d be surprised if people love being asked for help and ask you some difficult questions.”

• Guy Rubin on LinkedIn
• ebsta on LinkedIn
• ebsta website
• 2024 ebsta SaaS Sales Benchmarks Report

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.

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. The team grew to over 100 employees and nearly $10 million in revenue serving marketing professors and their students.

In 2021, they engaged with Vista Point Advisors, an M&A advisor firm, to shop the company to prospective buyers and investors, eventually getting a majority investment from Tritium Partners. Stuart describes the M&A process, what worked well, and how he transitioned out of the company after two years of continued growth.

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.

Quote from Stuart Draper, founder of Stukent

“When we officially sold a major part of our company to investors, we had a brief celebration. My CFO and I called each other and screamed as loud as we could on the phone in a fun moment. We got there, we did this. My family also took a big trip and I got a break.

“But then it was back to work. I was still the CEO and I still run this thing and I’ve got new investors that also need returns. I’m going to go deliver for these guys. They gave me a big payday, so I’m going to make sure they have a win too.

“After the second board meeting with our investors, I realized this is way harder than I thought. After eight board meetings and doubling the business again, I wasn’t enjoying this as much anymore. The board meetings were hard for me. Prepping for them was super stressful.

“So we found a new CEO for Stukent, and he’s doing great. Now I get to sit back in my chair at the board meeting, listen in, share my advice and opinions and come back in three months.”

• Stuart Draper on LinkedIn
• Stukent on LinkedIn
• Stukent website
• Tritium Partners website

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.

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-based financing from Lighter Capital to help test their growth plans. When they focused on field service route optimization and grew quickly, MapAnything raised several rounds of venture capital to grow even faster by focusing its sales and marketing efforts within the Salesforce ecosystem.

MapAnything reached $22 million in ARR before Salesforce acquired the company for $250 million. John stayed on with Salesforce for six months before moving on. John and a co-founder launched Fastbreak.ai three years later, a sports schedule optimization platform for professional and amateur sports leagues.

Quote from John Stewart, former CEO of MapAnything

“I tell founders most often that you really need to focus on sales and distribution. As a CEO of a startup in the tech space or SaaS, the only thing that really matters is revenue growth. Technology is technology. Even if you have unique IP right now, it won’t be unique soon enough.

“So you need to figure out your go-to-market motion. That’s the single most important thing. Revenue cures all ills. It doesn’t matter what’s going on in the company as long as revenue is growing. It’s all about revenue growth more than anything.”

• John Stewart on LinkedIn
• MapAnything on LinkedIn
• Salesforce website
• Fastbreak.ai website

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.