208: Bootstrapping a $50M/Year Business (And Exiting Twice) with John Arrow
Release Date: 12/25/2025
How High-Performers Decide What to Ignore (Behind the Scenes with Stu McLaren)
Beyond A Million
For a long time, being in rooms (masterminds, events, paid groups) were incredibly valuable for me. That’s where relationships were built, perspective expanded, and a lot of growth came from. But lately, I’ve been wrestling with whether that value still outweighs the cost—time, energy, relationships, broken routines, stepping away from the business, and more. And I know I’m not the only entrepreneur who struggles with this. That’s why I’m sharing this unreleased, behind-the-scenes footage from my interview with Stu McLaren. In it, Stu explains the exact rules he’s put in place to...
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212: The Recurring Revenue Model Used by 20,000+ Entrepreneurs with Stu McLaren
Beyond A Million
If your revenue resets every month, growth is harder to predict, and harder to scale. That’s why so many companies are moving toward a membership model. A lot of businesses assume recurring revenue doesn’t apply to them. Today’s guest has spent nearly two decades proving that assumption wrong. Stu McLaren has helped more than 20,000 entrepreneurs to launch, grow, and scale membership-based businesses across nearly every industry imaginable—and in this conversation, he breaks down how to identify where recurring revenue already exists in your business and how to structure it into a...
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211: How a “Boring” Business Sold for 2x Market Value with Will Duke
Beyond A Million
Physical security is a brutally competitive, commoditized industry. Most companies look the same, act the same, and sell for the same. Will Duke did things differently. And when it came time to sell, buyers lined up. He didn’t just exit the core business. Along the way, Will built an internal software platform to manage and track thousands of security devices for customers. That platform eventually became its own SaaS company, and both businesses were sold as part of the same exit, at roughly double market value. In this episode, we break down how he differentiated in a crowded market, what...
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210: How to Build a Luxury Brand That Attracts the Ultra Wealthy with Larry Walshe
Beyond A Million
Today, I’m sitting down with Larry Walshe, founder of , a global event design firm producing large-scale, luxury weddings and private events for ultra-high-net-worth families, celebrities, and royal households. While Larry’s roots are in floristry, his work goes far beyond flowers. His studio designs fully customized experiences—shaping the creative vision, transforming spaces, and defining how guests experience an event—while bringing together specialized artisans from around the world to execute complex, high-stakes productions. In this episode, Larry breaks down what it actually...
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209: How Amy’s Ice Creams Became Austin’s Most Beloved Brand with Amy Simmons
Beyond A Million
Amy Simmons is the founder of Amy’s Ice Creams—a beloved Austin institution with 19 locations built over 41 years—not through franchising or rapid expansion, but through deep community roots, creative culture, and an unshakeable commitment to people first. In this conversation, Amy shares how she grew the company without franchising, avoided national rollout, and even allowed each store to operate with its own personality. We get into the role theatrical customer service plays in the brand, how open-book management teaches financial literacy and strengthens decision-making, and why...
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208: Bootstrapping a $50M/Year Business (And Exiting Twice) with John Arrow
Beyond A Million
Most founders dream of selling their company once. John Arrow sold the same company twice. He bootstrapped a mobile product development firm (Mutual Mobile) in college, scaled it to 300 people, and pushed nearly $50M a year in revenue. But the real unlock came from one bold decision: moving upstream into enterprise clients. Prior to that, his model was unsustainable. He and his co-founders made the decision to fire all of their customers and only work with companies with a spend of at least $1M/year. That’s when their company took off. In this episode, John breaks down the decisions...
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207: How HighLevel Scaled to 2M+ Users Without a Sales Team with Robin Alex
Beyond A Million
Robin Alex is the co-founder of HighLevel, a marketing automation and CRM platform that has grown to more than two million users since launching in 2018. The company scaled rapidly—doubling and tripling year after year—largely through a white-label model that allows agencies and implementation partners to resell the platform under their own brand. HighLevel now operates with roughly 2,000 employees worldwide and continues to ship new features, including AI-driven tools, at an unusually fast pace. In this conversation, Robin talks through the real reason HighLevel gained traction, how...
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206: How Pat Flynn Turns Content Into Multiple 7-Figure Businesses
Beyond A Million
For nearly two decades, Pat Flynn has been creating content. What’s interesting is how that work has fueled multiple 7-figure businesses. Over the years, he’s launched and scaled companies across education, media, software, community, and physical products—from and to niche websites, podcasting tools, and more recently, a that pulls in 10 million views a day. What ties all of these ventures together is the way Pat builds them. Through his philosophy, he’s able to use content to test ideas, reduce risk, and explore a wide range of opportunities while still staying super...
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205: How 8-Figure Founders Use AI & Automation To Scale Faster with Matt Leitz
Beyond A Million
Too many business owners are trying to use AI as a shortcut to fire people instead of using it to multiply the output of their best people. And that mindset is killing their growth. Matt Leitz has been building automation systems for 7- and 8-figure companies long before AI went mainstream. He’s seen inside the machines powering 9-figure brands… and the truth is simple: automation isn’t optional anymore. If you want to scale, you need a business that compounds output without requiring more of your time. Matt breaks down how to use AI as leverage — not as a crutch. He shares where...
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Land High-Level Clients with This Simple 3-Thing Rule
Beyond A Million
This is a clip from the Beyond A Million podcast where I talked to Steve Sims – entrepreneur, speaker, coach, and bestselling author, best known as the creator of the world’s first luxury concierge service. Here Steve shares a killer strategy for getting the attention of high-level people (like billionaires or big-time investors). His approach is simple, but a bit unexpected… and it definitely doesn’t involve pitching or pretending to be someone you’re not. He also tells a wild story about how this exact move led to a long-term consulting deal with a serious player in Silicon Valley....
info_outlineMost founders dream of selling their company once. John Arrow sold the same company twice.
He bootstrapped a mobile product development firm (Mutual Mobile) in college, scaled it to 300 people, and pushed nearly $50M a year in revenue.
But the real unlock came from one bold decision: moving upstream into enterprise clients. Prior to that, his model was unsustainable. He and his co-founders made the decision to fire all of their customers and only work with companies with a spend of at least $1M/year. That’s when their company took off.
In this episode, John breaks down the decisions that unlocked explosive growth, the typical traps most founders never see coming, and why selling a services company is far more about timing and terms than topline revenue.
You’ll hear why he and his co-founders turned down a $100M offer, the minority deal that allowed him to take chips off the table, and how John was able to come back as CEO years later to orchestrate an 8-figure exit.
Key Takeaways
00:00 Intro
01:05 How He Started & Scaled Mutual Mobile
02:55 Why Shifting to Enterprise Clients Changed Everything
07:48 What Uber Taught Him About Testing Ideas Fast
09:34 The Pros & Cons of Using AI and No-Code to Prototype
11:04 The Life-or-Death App That Validated Their Model
14:20 How Mutual Mobile Found Its Identity Along the Way
16:47 The 2nd Dumbest iPhone App of All Time
20:22 An Unusual That Attracted Enterprise Deals
24:56 Why Austin’s Tech Scene is a Recruiting Goldmine
29:22 The Real Economics of Owning a Private Plane
44:47 How He Ended Up Selling the Same Company Twice
53:06 The Earnout Terms That Actually Matter
55:43 Creating AI Software with Zero Censorship
57:42 Why Operators Make Better Investors
58:57 When (And When Not To) Invest in Side Ventures
01:01:50 John’s Advice for Entrepreneurs in the AI Era
Watch on YouTube: https://youtu.be/zHnqoPxen0k
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