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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