The Entrepreneur Experiment
500 Episodes Later: Gary Fox on the Experiments That Changed His Life
21 May 2026
Chapter 1: How did The Entrepreneur Experiment podcast begin?
Hello and welcome to episode 500 of the Entrepreneur Experiment. I kind of giggle when I say that because this started as a complete experiment. This was the experiment. So I'm going to fill you in if you're a new listener or you haven't gone back to episode one, which is back in 2019. I'm going to give you a quick overview. How this whole thing started. And then we're going to do an AMA.
I put this up on my Instagram and my LinkedIn. and a few different other places for people to ask me any questions they have because I think it's really interesting that people can kind of just interact with me and ask me questions based on this whole wild journey of the podcast. So how did this all start? This is just a question. I think it's a very important answer first.
This started as an experiment. So back in 2019, I was running a property company called HostBullers and we did Airbnb management. So we had nearly 70 properties under management back at various points throughout the journey. And I was thinking I wanted a new network, but I also thought, you know, I could launch another business. I thought, you know, Host Futures is going well.
I can now launch a second business. So the podcast actually started as I was going to start multiple businesses, test them and then launch another business on top of the one I was already running. This was a terrible idea on so many levels. So the podcast was never intended to be this like main career, this main business, which is interesting in itself.
It was just literally an experiment within an experiment.
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Chapter 2: What was the pivotal experiment that changed Gary's life?
So I started HostBullers as an experiment. So I started HostBullers just by testing the idea. I put up a website. I had the idea a while back and then I was like, right, I'm going to test it. I was doing various other bits and pieces at the time. I was like, right, I'm going to test this and see if it gets traction. Then I'll put more focus on it.
So I put up a website and then I put up targeted ads. It was around the time that the Web Summit was coming to Ireland. I think it was in the early stages. This was back, obviously, 2019. The Web Summit was probably going about three, four years. It was the ticket in town. It was the hottest ticket in town. And there was massive demand.
There wasn't as many hotels in Dublin, obviously, as there is now. So there was always massive demand. And Airbnb was this kind of hot new platform. I'd used it a couple of times in the previous year. So I'd used it in Washington for a friend's wedding. And then me and Michelle went and did the run with the bulls in Pamplona.
So I did the run with the bulls and we stayed there because it was kind of a notion. Like most things I do, I got a notion. We were in Barcelona. I was like, I'd love to run with the bulls. I don't know why. And then we got a bus, an overnight bus to Pamplona.
the only place to stay was an airbnb a room in some lad's house did that i was like oh this is kind of cool so it kind of had the idea from airbnb it was a really new platform and it was totally different how it is now so tested there the airbnb property management idea it took off so i said you know what that worked once let's do it again let's run multiple businesses
And then after about a month, I realized that was a terrible idea, probably less than a month. I was like, right, that's awful. So I had two ideas, two reasons for starting the podcast. I was going to use it to get mentors to help me with this new idea. And then I was going to document the business idea as I developed it and as I launched and tested them.
So after about a month, I realized this is a terrible idea, but I actually enjoyed the podcasting and actually enjoy having new mentors and talking to people. And I kind of snowballed from there. So that's how the podcast started. And then I focused exclusively on talking to other people. I documented my own journey in parts, especially during COVID.
I shut down the property management company for various different reasons, which I'll actually get into in today's AMA. and then went all in on the podcast. So about 22, 23, went all in on the podcast. So I'll talk about that as we go through the journey today. So AMA number one. What experiment, what one experiment completely changed your life? That's from Pete. There was multiple.
And I think the one that changed my life most recently was definitely Hostballers, probably the podcast as well. But then the one that changed probably my personal life was we bought a barge 10 years ago, actually 10 years ago or 10 years ago, a month ago, we bought a barge in Athlone. renovated it, sailed it to Dublin and lived on it for four years.
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Chapter 3: When did podcasting shift from a side project to a serious business?
And that was one of them. And I looked at like camper vans. I looked at tiny homes, which became a side business later on. And then I looked at boats and boats is the quickest, easiest, the most straightforward, not the most straightforward, but definitely the one that could get going fastest. I have a real impetus to action. I'm impatient. That's a fancy word to say and I'm impatient.
So that was how I, we lived on a boat for four years. That was probably the best experiment. We bought it, renovated it, made it really cool.
Chapter 4: What is the biggest lesson learned from 500 episodes?
I'll put up some images on my Instagram in the next week. I'll actually coincide with this, the release of this. If you go to my personal Instagram, Mr. Gary Fox, I'll show you pictures of the boat. So head over there now and follow me there. And I'll put up pictures of the boat 10 years ago, how we renovated it. And then as we lived on it. So I think it's a pretty cool story.
So that was probably the experiment that had the most impact on my life. Okay, next question. What was your most difficult interview to date? And that was from Ruth and why? Two spring to mind. One was on the podcast, one was at an event. So one on the podcast was a guest I'm trying to get on for a very long time, quite a high profile person. And the night before, they'd canceled twice already.
And then the night before I got an email, I just had my spidey senses were tingling. I just sent a double confirmation email going, hey, look forward to seeing you in the morning. Any questions, give me a buzz on this number. And then I got an email saying, oh, just we have a number of conditions you'll have to meet if we're going to do the podcast. Now, we'd already arranged this.
This was arranged like ages ago. There can be no paid spend behind the podcast. You can only put out one social clip to promote the episode. And there was another one which I won't reveal. And I was like, well, that's not how we do it. You know, we can't if we don't promote the podcast. It's in neither of our interests. So, you know, we put out like as many social clips as we can.
It's in your interest and my interest, because then we both the podcast gets more exposure. The paid spend is fine.
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Chapter 5: How can young founders earn a seat at the table?
We don't use paid ads. And the third one is. It was a bit of a problem as well, but I was okay to get around it. And the person's assistant emailed back and was like, well, if you don't agree to conditions, we're cancelling the interview. This was 12 hours before. Studio set, videographers booked, everything booked. So I kind of thought about it.
And in the end, I went ahead with the interview because I knew the person would agree.
have a huge draw i was very keen to get them on and it would be it was odd that i hadn't had them on already try not to identify the person anyway so i did it really awkward uh beforehand really awkward after on the pod they were all perfect they were had their pr game face on and people often reference going that was one of my favorite podcasts ever and i was like good yeah good good
So anyway, that was one of the most difficult. And then there's a couple of podcasts that never went out. They were exceptionally difficult for different reasons. They just never went out. And then the other one was at an event I was booked to do. So I was asked to host a big event. As part of that, there was someone quite famous coming in from another country.
And we'd done a deal that we'd do a podcast as part of that. They refused to do the podcast, a separate one. And I said, well, look, we'll just record the chat we do on stage and then that could be a podcast. And then the person refused to do that as well. And then on the day they refused to do any prep. So they refused. I always try to have 30 minutes with the person at least.
And this was a big deal. It was a big event. It was the highlight of the whole conference. And this was the keynote speaker. A lot of people had come to see. So it's on me as a professional to make sure people get as much from it as they can. If they paid attention. If you've paid harder money for your ticket, I am going to do the very best I can to make sure that that exceeds your expectations.
That comes from being a professional. That comes from preparation. That comes from building a rapport with the person and getting them comfortable with you and you get comfortable with them. And it just leads to an all around better chat, right? It's more natural. My style is quite conversational. It's quite natural. So they refuse to do that.
And in the end, I got like one of the people that were in the conference came over and they're like, they'll give you two minutes. I was like, well, what the hell? So I went in into the green. They were sitting in a separate green room. They wouldn't come into the main green room with the rest of us. They were sitting in a separate green room. I went in. They were sitting there with their PA.
And it was such a chilly atmosphere. I went in. They were sitting at a table, like a long table, quite on their side of the room. So I walked over, introduced myself to both of them. Neither of them stood up and they kind of like just looked at me as I stood there in front of them. I was like, so just want to kind of run through a few bits and pieces.
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Chapter 6: Will AI replace the personal touch in coaching and mentorship?
I'm really a strong believer in that, in that we always think, oh, they got knocked out by the rival, you know, Adidas came and took over Nike and blah, blah, blah. There is an element to that, right? But I think most of it is
we fail to innovate we fail to keep going we fail to execute at the right time so that's the belief i have is that you can you can have it all i suppose that's what i'm trying to say i think you can have it all you can't have it all at the same time but you can't have it all if you're willing to take a long-term horizon knowledge okay next question what skills do you think ireland's youth need to keep up with the pace of change that's from kim mckenzie doyle
That's a really good question. And I was only talking to someone about this last week in that I think it's an incredibly turbulent time for younger people coming out. But again, we always think this. We always think everything is changing forever. The internet was the change that changed things forever. Smartphones were the things that changed things forever.
Remote work were the change that changed things forever. The only thing constant is change and chaos and being comfortable in the chaos. The skills... I think are the same as they've always been. The ability to take action, the ability to make decisions, the ability to be decisive and getting experience. What I think people lack now is experience. They lack work experience.
They lack real world industry experience. Again, I had a couple of experiences recently where I was trying to hire someone to help me out on specific days for specific jobs. And they wanted like a rate that you'd pay someone who's at the gig five or 10 years. it's just not there. Like, you know, when I started in the phone shop in Nina, I was so happy to be working.
I didn't expect to be paid the same as someone who's there five years. It just doesn't work like that. So I think there's an element of social media has kind of skewed people's reality of, You know, you have to pay your dues. You really have to do the years of hard yards. And I think apprenticeships should be utilized far more in all industries, not just like the trades.
I think apprenticeships are massively underlooked. Like if you want to become an entrepreneur, go work with an entrepreneur is kind of how I think about things. Yeah, college is good and important. That can teach you a lot of life skills and teach you a lot of social skills. But I would love it to be 50-50.
I think if you really want to succeed, if you want to be a great writer, go study under a great writer. So that's kind of my core belief in that. And I'm actually thinking about taking someone on for the summer as an apprentice or taking someone on for 12 months as an apprentice. So that's kind of my belief. Am I doing any more retreats this year? I didn't get in last year from Fiona.
Sorry, Fiona. Yes, I am. I am going to do a retreat. I'm probably going to do an Irish retreat and then I'm probably going to do one in Spain or Portugal towards the end of the year, probably Q3, Q4, so probably September, October time. Again, if you're on my newsletter, you'll get access to those first. So go to mrgaryfox.com and you get your newsletter there.
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Chapter 7: What does success look like for Gary now?
Tammy's going to laugh because she gave me her answer and I'm going to kind of more or less mirror it now. I think they're pretty much the same in terms of the traits. Obviously, the social entrepreneurs are doing it for a very strong reason. I think they have a very strong passionate reason for doing things. Most entrepreneurs have a reason.
They're solving their own problem or they really want to build a life for themselves. But I think social entrepreneurs really want to make a broader impact. They're obviously... I think you have to be doing it for a profit. I mean, everything I teach on a climate entrepreneurship class in Trinity and one of the first things I get into in the morning is you have to survive to thrive.
And what that means is generally if they're working in a climate entrepreneurship space, they're extremely passionate and that can be problematic because you can think too big. And that sounds kind of weird in that, well, why would you not want to think big? You have to be able to survive first. You have to be able to get through the initial 12 to 24 months. And that requires thinking small.
That requires how can I make an impact very quickly while still making money and being profitable? Because there's still an enterprise, right? The clue is in the name social enterprise. You're doing it for a social good, but you are an enterprise. So I always try and make sure that they understand that it's important to be able to be sustainable.
If you are relying on grants and you're relying on good people's nature, you mightn't survive long enough to make the impact that you want. So I think social entrepreneurs are the same as entrepreneurs. It's the same thing, right? You're an entrepreneur. It doesn't really matter whether you're in the social space or the private sector. not private sector, you know what I mean?
You're doing it for profit. Both are doing it for profit just for very different reasons. What does success actually look like for you now? That's from Sarah. I kind of alluded to this earlier. It's the long journey.
It's being able to design a life that I love around my body, business, my brain and my family, and that I'm never answerable to anyone, that I'm able to build this machine that is giving me a life that I absolutely love. I don't mind that it might take me an extra 10 or 20 years longer.
It's that I'm able to have the freedom to make the choices that I want and to be able to do not do good, but do good by doing good, if that makes sense. As in, I want to put out stuff into the world that is a net benefit that people learn from, they enjoy, that they help them build the life that they want. I don't mean to sound like a bleeding heart here or like a goody two shoes.
I like putting out stuff that people enjoy. I think there's so much negativity. There's so much garbage on social media. There's so much toxicity, especially in the world right now, that I feel a lot of my content is long form and it's quite It mightn't get the impact or the reach because I deliberately don't go after the controversy.
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Chapter 8: What are Gary's predictions for the future of The Entrepreneur Experiment?
Gary, love your pod. Can fitness and purpose solve male loneliness? That's from Andrew Desmond. It's a big question. I don't think one thing can solve modern male loneliness. I think it can definitely be a foundational part, though. For me, I train every single day for my health and my mental health, being honest. My mental health wasn't very good during COVID.
Various different reasons play a factor in that. But training is the outlet that I adore. It changes my life. It changes my mood. It changes how I feel. It changes my confidence levels. If I don't train, I'm not very confident. So I think it has a massive ripple effect. Nothing can change one big problem on its own. But I do think that's why we're seeing such a rise in the wellness space.
I love the wellness space. I was at Wellfest a few weeks ago to see the amount of entrepreneurs building in the wellness space. I love it. I think it's absolutely class. So I think... That's why you're seeing such a spike in running, in High Rocks, in gym memberships, in boutique gyms, in like Pilates, yoga, you know, Saints Studios, Back to Basics. All these places are absolutely thriving.
I think that's because people are searching, male and female. They're searching for connection and community, especially after COVID. We live in a bit of a disjointed world because that was definitely a massive trauma event. And I think we didn't really process that properly. There was like a war, essentially. And when you think back on it, it's absolutely wild.
So I think we're still processing that. I think people's lifestyles have fundamentally changed. They're not drinking as much anymore, which is excellent for your health. But going and being around other humans is incredibly good for your mental health. So while that had a massive, massive negative impact on your physical health, being out with other humans helps your mental health.
So I think we're still in the early stages of figuring all this out. I love to see like run clubs. I love to see like, you know, Hirox clubs and Hirox gyms coming together because it's That's what we need is to be more connected. And I think social media is poison when it comes to that. I think social media is the biggest driver of loneliness. I think men are struggling.
This is why we did the well man tent a few weeks ago at Wellfest because men are struggling to find their way in the world. And I'm not saying boohoo men here. Women have had it much tougher than men for much, much longer. So yeah.
um it's not an isolationist bubble thing either i think nothing gets solved in a bubble i hate when i see people like all men going off together all women going off together i just think that doesn't help you need both because both are exceptional in helping each other so i think it definitely is huge and finding competitive outlet is very important for men men need competition where primitive urges need competition in terms of you need to be able to like
satisfied that caveman urge of going out and fighting and competing. I think you do need that to be in one way. From Anthony Kelly, who did Wellman and Wellfest with me, founder of Wellfest and Glowfox, who is your ultimate dream interviewer? In the short term, it's John and Patrick Collison from Stripe. I would love to interview them because I think they're the master experimenters.
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