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.

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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.