Beyond A Million 208: Bootstrapping a $50M/Year Business (And Exiting Twice) with John Arrow
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 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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