How Jim Cregan Turned £50k Debt Into A National Coffee Brand

5 Dec 2025 · 9 min

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In short

Podcast Episode Summary: How Jim Cregan Turned £50k Debt Into A National Coffee Brand

Podcast Information

  • Title: Screw It Just DO It
  • Host: Alex Chisnall
  • Guest: Jim Cregan, Co-founder of Jimmy's Iced Coffee
  • Release Schedule: New episodes every Tuesday and Thursday

Episode Overview This episode features Jim Cregan's inspiring journey from being £50,000 in debt to building Jimmy's Iced Coffee into a nationally recognized brand. It emphasizes the hard work, creativity, and resilience required to succeed in entrepreneurship.

Key Themes and Concepts

  • Momentum in Adversity:
  • The episode highlights that significant momentum often occurs when financial pressure is highest.
  • Jim outlines that many founders give up when the situation becomes challenging, but he found success by taking action during tough times.
  • The Power of Personal Outreach:
  • Direct, personal communication was fundamental in opening doors that larger marketing campaigns could not.
  • The anecdote of Jim writing to a coffee brand he admired while in Australia showcases this point.
  • Simplicity and Quality Over Branding:
  • Jim emphasizes that product quality and authenticity build trust faster than flashy branding claims.
  • The importance of creating enjoyable experiences for customers is also discussed.
  • Resilience vs. Planning:
  • The significance of resilience is highlighted as more essential than having a perfect plan, especially in the early stages of building a business.
  • Jim’s journey illustrates that adaptability and perseverance can lead to unexpected success.

Key Takeaways

  • Entering the Market:
  • Jim's approach involved starting without a clearly defined exit strategy or end goals, focusing instead on creating a quality product and enjoying the journey.
  • The Emotional Connection:
  • The thrill of seeing someone choose and enjoy your product in public is a significant motivational factor for entrepreneurs.
  • Jim expresses joy and pride in seeing real-life instances of consumers enjoying Jimmy's Iced Coffee.
  • Evolution of Business Vision:
  • Initial visions evolve over time; Jim reflects on how his aspirations shifted from handing the business down to his future children to understanding the business landscape and aiming for scalability.

Personal Anecdotes

  • Jim shares a story about an unforgettable road trip in Australia, which helped him find inspiration for his iced coffee brand. This journey served as a personal and professional awakening, showcasing the importance of experience in shaping entrepreneurial ideas.
  • The initial rejection from the brand he admired eventually turned into a recognition of his success, highlighting the unpredictable nature of entrepreneurship.

Conclusion The episode serves as a motivational reminder for entrepreneurs that the path to success is often fraught with challenges. It illustrates the importance of taking proactive steps, maintaining resilience, and staying true to one’s vision. Jim Cregan’s journey with Jimmy's Iced Coffee stands as a testament to the idea that momentum can often be found right at the edge of quitting.

Follow-Up

  • For more insights and real stories from entrepreneurs, follow the *Screw It Just DO It* podcast on your favorite platform.
  • Stay connected with upcoming events and updates through the Festival of Entrepreneurs website and social media.

Hashtags

  • #ScrewItJustDoIt
  • #FestivalOfEntrepreneurs
  • #StartupLife
  • #Entrepreneurship

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Transcript

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0:00The first thing was just to get out of the hole, literally the hole, digging holes, doing festival work, and giving myself a new purpose that I knew was going to grab me by the horns and take me to get to go to go. do something and actually prove to ourselves that we can do something amazing. Today's Bite Sized episode features one of my favorite people, Jim Cregan, founder of Jimmy's Ice Coffee, the Dorset born brand that became a household name. We didn't change any tact or change our marketing or just go for sales or anything just to win that. In the end, we made sure the journey was fat and juicy and fun.

0:40And then if it turned out that they liked us and we'd reach that milestone of that turnover, then that would be great. And that's essentially what happened. Welcome to this special bite-sized episode of Screw It, Just Do It from our back catalogue of over 550 past episodes. For those who are new to the story, they might have seen stories back in July when you exited the business. Yeah. Tell us briefly what happened in Australia and what inspired you to come back to the UK and literally start Jimmy's Ice Coffee. It was one of those hungover. We bought a Holden Jackaroo, which is a, what would it be called over here?

1:20An Isuzu Trooper. It's like an old school, land cruiser-y style thing. It's a bit bogan, as they call it, over there. But it was rad. We ripped the back seats out and put a bed in the back and roof rack and water tank and logs and stuff. It's the kind of thing you see on Instagram and go, I wish I did that. And we did that, and we did it for like five months. and it was so sick. And we basically just met really cool people. We worked in surf shops and surf schools. I remember working in surf schools as an assistant and there was an English lady and she was just like, and I was like, hello. And she's like, oh God, I was kind of hoping for some like Aussie hunk to push me out in the water and I'm getting you from Bournemouth.

1:57And I was like, sorry, love, look at the draw. And she's like, so, but yeah, no. So we just had like a really properly, properly cool time. And this is without kids, which was just, the best i love my kids but my god it was so much fun yeah so we really hung over and we just went into a petrol station and i was like i'm hung over i want something cold i need some energy i don't want red bull i don't want water i don't want tea that's boring i then just stumbled across ready to drink ice coffee and this product called farmer's union it comes in a carton and it's the best thing to open because it's like cardboard and you can feel it on your like lips and it's just aesthetically just this most amazing thing and i was just like hooked on it immediately and then wrote to the company while i was in oz not knowing that we're even going to go back to the uk and i was like i'm a laborer from the uk i've just found your product and i need i need to basically when i do go back to the uk in 100 years i want to i want to license or brand your your um license or franchise your business no like mate you're you're mental and i was like please and they said no it's still not happening and then after doing about four or five years of business at jimmy's the like adelaide times or herald or something got in touch with us because they'd been speaking to farmers union which is the company i fell in love with and they said um did you realize the guy who um who emailed you has now started up a nice coffee company and is actually doing okay so the brand manager sent me an email saying mate i'm so sorry we didn't listen to you that's brilliant i mean you're too late yeah but it was really cool to have that to have that chat with him um so yeah it's been such a wild like amazing yeah insanely fun journey that's definitely one of those screw it just do it moments then to get a hundred percent yeah yeah yeah if you've got that email frame somewhere i have it on i think i've still got my hotmail because it was jimbo creagan at hotmail.com and you know it should have been like i'm great at importing brands into the uk at gmail um and uh yeah it's there somewhere and there's actually the there's the reply so you can actually see the thread and it is literally like oh go on in this in the second email oh come on mate and it's just like god if i was restructuring that email i'd be like do not write an email like that in fact don't write an email do something else to get their attention because that's just ridiculous um yeah loads of fun though and when you did launch uh jimmy's iced coffee between you and suze did you map out a specific vision or when you look back now is it just a pipe dream that you might get there one day i think these the first thing was just to get out of the hole of literally the hole of digging holes um and doing festival work and giving myself a new purpose that i knew was gonna like grab my grab me by the horns and take me into a new place whatever that looked like from a value perspective or how big it would be or how many employees you'd have or how many like gun shows you can do in your company with it it doesn't really matter it was more a case of like let's go and do something and actually prove to ourselves that we can do something amazing what that looks like i have no idea but we're going to be proud of something that we're going to make and then i remember kind of by year year one and two people were like well where do you want to this is quite exciting where do you want it to go and i'll be like i want to hand it down to my kids i hadn't even had a kid by then i was like handed down to my kids and then after year three i'd be like if i had kids and handed down to them they would have have me killed because it's the worst business in the entire world.

5:22And then you see, you read in the grocer and you're like, oh, this tiny brand has sold to this big company. And we're like, that sounds quite cool. This is a scalable business that, you know, that's it. It's something that we could do. And then come year five, six, seven, you kind of try and understand what you need to look like as a company that becomes attractive to a potential buyer. And it never really, we didn't change anything apart from, We just knew that you had to get to a turnover of about 10 million quid before a big business looks at you and goes, okay, you've been in the game for long enough.

5:56You're large enough to make an investment into. But we didn't change any tact or change our marketing or just go for sales or anything just to win that in the end. We made sure the journey was fat and juicy and fun. And then if it turned out that they liked us and we'd reached that milestone of that turnover, then that would be great. And that's essentially what happened. So I remember like interviewing Richard Reid from Innocent Smoothies and like someone like an Al Barrett from Grenade. And like both of them were like, never thought of an exit strategy when we were starting. I'm assuming you weren't more cunning than they were, but you were the same.

6:34It just threw out that journey. It was just the buzz didn't wear off for literally just seeing someone drink your product. I mean, initially you had to give someone the product for them to try. and if they liked it, that was all you needed to go to the next day. And then you find out or you see people in the wild drinking your products and that's still... In the wild. Honestly, I froth when I see people do that. I froth. I remember seeing this dude at Pokes Down Hill, there's a Tesco Express, and this mush came out and he cracked open a mocha. And he must have had it before because there was no hesitation.

7:11It was just like a full gun show. and I was like I nearly crashed the car because I was hands off the steering like what out the window and I got and it's just so cool to see that you've done all this work and what's so nuts is they'll they would have gone into that Tesco Express and their like drinks fixture will have I don't know how many maybe 80 120 products in there and they've chosen arse over someone else's and you're like what have I done to persuade them is it the branding the packaging the ingredients is it funky marketing is it all this kind of shit that you have I have no idea. And you're not going to go and ask them because they'll probably call the police.

7:48And it's just really cool to see that people have gone. I like that product. And you've, that's all of your blood, sweat and tears. It's not all of the other stuff. It's actually seeing people enjoy your thing that you've made. And you're like, this is, this means something to someone. And it's so cool. And when you saw mush, did you then think my work here is done? Yeah, essentially. And it's, it's rare that I do see people drink our stuff, but when you do, it does make you like really kind of stoked about you've done, you've done something proper. And it's not like it's the only, it's the only kind of scenario where it's, it's you haven't asked them to drink it or anything.

8:26They've just gone and done it off their own back. And to catch someone at that particular moment, see it happen is really cool. So those of you who followed the show for a while now will know all about Jim. My first live event was hosted at Jim's HQ, at Jimmy's Ice Coffee HQ. And we've done a number of things over the years together. And look, Jim's story for me is all about being authentic, about building something you actually believe in. Definitely having fun whilst you're doing it and not being afraid to stand out. If you love this one as much as me, please follow Screw It, Just Do It.

From the publisher

Jim Cregan built Jimmy’s Iced Coffee from a simple idea into a national brand. This episode captures how he pushed through debt, setbacks and doubt to create real momentum.

Speaking with Jim Cregan reminded me how often founders underestimate the grind behind a brand that looks simple from the outside. Jim described the early days of Jimmy’s Iced Coffee when he was £50,000 in debt, unsure of the next step and carrying the pressure of keeping the business alive. What shifted things was not luck. It was action. Handwritten letters, direct outreach, relentless product sampling and a refusal to step back when the numbers looked bleak. This Bite sized episode is a sharp reminder that momentum usually starts at the point where most people quit.

Guest: Jim Cregan, Co founder of Jimmy’s Iced Coffee

Key Takeaways:

  • Momentum often begins when financial pressure is highest.

  • Personal outreach can open doors large campaigns cannot.

  • Simplicity and product quality build trust faster than branding claims.

  • Resilience matters more than perfect planning in the early stages.

 

🎧 New episodes of Screw It Just DO It drop every Tuesday & Thursday, so make sure you follow wherever you listen. You’ll hear real conversations with founders who’ve taken a risk, built something from scratch, and figured it out along the way.

FOE returns to NEC Birmingham on November 3-4, 2026. Stay connected at www.festivalofentrepreneurs.co.uk and follow @festivalofentrepreneurs for news, updates, and future events.

 

Real entrepreneurs. Real stories. Real strategies.

 

👉 Follow the show. Keep showing up. Screw It Just DO It!

 

#ScrewItJustDoIt #FestivalOfEntrepreneurs #StartupLife #Entrepreneurship


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