How to Retire from Your Business Without Killing Its Growth (AI, Startups & the “Gray Hair” Advantage) - Steve Endacott

2026-02-04

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What if you could build a company you never have to run again—yet it keeps growing, thriving, and changing lives? In this episode of Hacks and Hobbies, Junaid sits down with entrepreneur, investor and mentor Steven Endacott, who sold his travel and insurance businesses (including Holiday Taxis for $60M) and then chose a new game: helping the next generation of founders build AI-powered companies he never has to operate. Steven reveals the model behind his incubator, where experienced “gray hairs” and young AI natives

What if you could build a company you never have to run again—yet it keeps growing, thriving, and changing lives?

In this episode of Hacks and Hobbies, Junaid sits down with entrepreneur, investor and mentor Steven Endacott, who sold his travel and insurance businesses (including Holiday Taxis for $60M) and then chose a new game: helping the next generation of founders build AI-powered companies he never has to operate.

Steven reveals the model behind his incubator, where experienced “gray hairs” and young AI natives build disruptive B2B products together. He breaks down how to find people you can actually trust, how to structure equity so it doesn’t trap you later, and why most founders get “replacing themselves” completely wrong. If you’ve ever dreamed of stepping back from the day-to-day without stepping away from impact, this conversation is your blueprint.

In this episode, you’ll discover:

How Steven sold his companies and rewired his identity from operator to chairman
The powerful model pairing “gray hair” experience with young AI talent
Why you should never lock in all your co-founder equity on day one
How to find, test, and keep the right people in high-speed startups
Why most AI opportunities are B2B, not B2C—and how to think like a real disruptor

Timestamps

[00:00] The setup: building a business you never have to run again
[01:59] Selling Holiday Taxis for $60M and choosing a new game
[02:40] The Newer River model: gray hairs, young AI grads, and shared equity
[04:32] Engines vs cars: how to actually win with AI in business
[06:57] Who can you really trust? Building teams that move ultra fast
[09:26] The biggest mistake founders make when replacing themselves
[11:11] Why most AI startups fail—and how Steven recycles top talent

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