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
Guest Links
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Junaid Ahmed is a multi-passionate creator, storyteller, and home studio architect who believes your voice can change your world. As the host of Hacks and Hobbies, he dives deep into the journeys of people turning passion into purpose — from garage inventors to global entrepreneurs.
The podcast began as a simple idea: record honest conversations about side projects, creativity, and the hustle behind the scenes. Years later, it’s become a movement — showcasing the real, raw, and inspiring stories of everyday innovators.
Whether he’s building pro-level studios or geeking out over podcast gear, Junaid’s mission is clear: help people show up with confidence, clarity, and character.
🎧 New episodes weekdays. New perspectives in every story.
