Podcast Episode

EE503 - Mentor Moment: Bobby Kerr - How to Scale Without Letting Ego Get in the Way

The Entrepreneur Experiment

Jun 1, 20268 min

Who’s talking

2 speakers
Bobby Kerr6 min · 70%
Gary Fox2 min · 30%

1Transcript21 turns · 8 min

GF
Gary Fox0:00

Welcome to this week's Mentor Moment. This one is with Bobby Kerr, someone we all know and love. He's the former CEO and founder of Insomnia Coffee and a former Dragon on Dragon's Den. This is packed with hard-won founder lessons. Bobby breaks down exactly what nearly took him out in the early stages and the simple strategy through all his successes. Here is your mentor, Bobby Kerr.

BK
Bobby Kerr0:21

What was your biggest mistake in the early years? Not having enough capital. Uh, Underfunded. Basically, I never spent too much in shops, but I probably went in too tight on the basis of what something was going to cost. Well, I didn't have it. So I was underfunded, which meant it was very stressful in the early days. We were close to the wall on a few occasions. So that can be... It can spur you on as well, but it can be challenging.

GF
Gary Fox1:03

And then how, you briefly alluded to it earlier, you went from one business to two business to three business. How does that merger come about? Was that a buyout? Did you buy them out? Did you join French? I actually

BK
Bobby Kerr1:14

sold my business to Insomnia, believe it or not. And then I did a kind of a really weird thing. The money I got, I put it back into the business and became the CEO. So it was like... I was a seller and a buyer almost on the same day, believe it or not.

GF
Gary Fox1:33

How does that come about?

BK
Bobby Kerr1:34

Well, it's just the way it came about. There's more to that. Well, they needed someone to run the business, and I was the person. Okay. So I said, I'll run the business. I suppose I didn't really want to sell the business, but I knew that if I didn't collaborate, I'd never get scale. So to me, I was much better off with say 30% of something that was far bigger than 100% of what I had. And that was probably one of my smartest moves, believe it or not, to actually see that there was more value in owning 30% of something that could grow rather than 100% of something that was, who knows where it was going to go.

GF
Gary Fox2:22

That's quite strategic. Like, I mean, you can see strategic decisions in your journey here. It shows, again, the lack of ego, but it's quite strategic to let go of something you've spent a lot of time and you've remortgaged your house on to then even take a bigger punt.

BK
Bobby Kerr2:37

Yeah. Yeah. Well, you know, I think a lot for me in business, you know, you start off with something, you grow it, you grow it, you grow it. There's only one payday. That was the way I looked at it. Okay. There's only, you build this, you build it, everything that you generate goes back into it. And then hopefully one day you get an exit.

GF
Gary Fox3:01

Okay. So you were happy to play the long game here. Absolutely. You were like, I'll play the long game and have one day there. No,

BK
Bobby Kerr3:06

absolutely. And I was never in it for a short term. And all up, you know, I was there between Perk and Insomnia, I was there over 20 years. Hmm. Yeah.

GF
Gary Fox3:19

So when you went and you joined all the businesses together, talk to me about that because I'm sure that is difficult.

BK
Bobby Kerr3:26

Well, it is, and you've got personalities and you've got different people from different businesses. But, you know, you've got to, again, see what the best – You know, the best name was Insomnia, without a doubt. It looked good, it looked good on a sign. It

2Episode notes

In this Mentor Moment, Bobby Kerr - former Dragon and former CEO of Insomnia Coffee - shares the strategic lessons that helped scale Insomnia from a small coffee business into a recognised national brand. Bobby breaks down why underfunding was one of his biggest early mistakes, how letting go of ego helped him choose the right brand name and structure, and why partnerships with companies like Spar, Easons, Penneys, and Meadows & Byrne became key routes to growth. This is a practical lesson in playing the long game, building multiple revenue streams, and making the kind of strategic decisions that give a business more ways to survive and scale. Listen back to the full conversation in Episode 439 of The Entrepreneur Experiment - and subscribe/follow so you don’t miss the next Mentor Moment. *Our Sponsors * Nostra: https://bit.ly/nostra26 Azure: https://bit.ly/azure26  Follow The Entrepreneur Experiment: Instagram: https://www.instagram.com/entrepreneurexperiment/ TikTok: https://www.tiktok.com/@entrepreneurexperiment

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