EE 333 - The Biggest 5 Lessons from 5 Years! Pod Anniversary Special

I'm going to chat to you for the next 10, 15 minutes about the five years, about the journey, and I'm going to give you five lessons from the five years. We are approaching one million downloads on the podcast, so when that hits, I'm going to do a full hour long interview with myself. Obviously, I'm going to get someone to do it with me, but I'm going to get someone to interview me about the whole journey of the podcast in true narcissistic fashion of hitting one million.

What a better way to celebrate it? I'm going to do a full hour long episode with me my journey to the podcast, my journey, entrepreneurial journey, my backstory. First, I'm going to give you five lessons on the podcast of our five year anniversary. So before we start that, I want to say a quick thank you to our partners, because without our partners the podcast does not exist. I'll touch on more of that when you come back from this message.

So welcome, welcome to our five year anniversary special. I've made some notes because I'm a professional and this is an important episode. So I'm going to do five lessons because why not? I'm going to cover what I've learned over doing the podcast in the last five years and kind of like bring you up to speed on kind of how the podcast started. Because if you haven't gone back in this episode one, the podcast was not designed to be an interview podcast.

The podcast was originally designed for me to explore startup ideas. I've always been fascinated by kind of experimentation. That is why the podcast is called the entrepreneur experiment and I still believe that to my core. I believe all good businesses are built on experimentation and I thought, hey, don't be cool, I'll do an experiment whereby over the next 12 months, I build MVPs, minimum viable products of five businesses. I'll test which one works and then I'll pursue the one that works.

Now, that would have been a good idea, and it actually is a great idea for content, but I was also running a business at the time which was doing quite well. So I used to run a company called host spotters which was an Airbnb management company. So I'd started that with 500 quid. I'd bootstrapped it, starting with 500 quid, literally, ran some Facebook ads, tested the market to see where people into Airbnb management they were.

I built it from zero properties up to 70 properties all around Dublin, built it to a staff of three people contractors and quite a big business who were turned over about half a million a year. So relatively good business, considering it was bootstrapped and I said I do the podcast on the side because I was just interested in it. It was an experiment, I thought it'd be cool.

I also knew the Airbnb management business was never going to be a longterm business because when you build on some else's platform, you're always at risk of that platform changing or of the kind of the something happening and that's something happened to be COVID around, clean off. So it wasn't the platform. Airbnb has actually gone from strength to strength and I'm still extremely bullish on that platform as a business. But what happened was COVID.

So essentially the business was a middleman business or middle person business and we would act as the middle broker between the landlord, which would in the host and the guest so we would kind of smooth, we can look after the property for them. We'd manage all the bookings, we manage all the communications, the check-ins, the check-outs, the cleanings and incredibly intense business.

And when I started, just from an experiment, I literally had just kind of I'd run many startups over the years and I'll cover that in the millionth download episode. But I just love being my own boss. I'm kind of agnostic about the idea but I love my freedom. I love my time freedom and the authority to do what I want when I want and not in a kind of a blasé, oh I'm gonna work 20 hours a week and live on the beach, not in that kind of way, more so than I value my time. I always have done so.

The podcast was meant to be exploring kind of new ideas. But I underestimated it greatly how difficult that would be. Because when you're running a business, obviously you've stakeholders, you've staff, you've customers and when they kind of see you doing a podcast but exploring other businesses, I hadn't really thought that through. It doesn't really send the best signal to people when you're exploring other business ideas, when you're running a business.

So that was a massively massive oversight. The other thing I massively overlooked was, to be honest, I do have the work ethic to launch and simultaneous businesses. What I didn't have was the ability to scale that out and do content at the same time, to be honest, underestimated how hard content is. I didn't really understand the podcast content game. So as soon as I started doing it, I'm like I need a publishing schedule. I need to publish this every week, I think.

Do I need to do it every week? I don't know. When I started podcasting, I had in the clue what I was doing. I did not have an absolute notion. I literally bought the equipment on Amazon, connected it to my laptop and a couple of months later, had the guts to actually take it out of the wardrobe, sit down, connect my laptop to it and hit play. And I just started. I did not know what I was doing.

So I edited it all down to the first 30, 40 episodes myself, removing all the mmms, us, maybes, ous, removed all them. Nothing gets you to be a better speaker than editing your first 40 to 50 episodes. And I also wanted to get new mentors right. If I was gonna start new businesses and to improve my existing business, I needed new mentors, and the best way to do that was to add value and bring value to them. I always say this to people when I'm teaching them how to network.

I was like don't go into networking as like the old, traditional way of going to events. Bring something of value and do it one to one. So I was like, right, I'm gonna reach out to all these amazing entrepreneurs. What am I gonna give them in value? I'm gonna give them a podcast. And that worked really, really well. And do you know what else I discovered? I really enjoyed it. I really enjoyed sitting down with other entrepreneurs and hearing their story.

I'm just so curious about other entrepreneurs, business, business models. I'm a business nerd. I just love learning about founders and how they think, how they approach their business, because from a psychological point of view, but also just from a story point of view, I love stories. I'm a massive nerd. I read so many books, fiction, nonfiction, whatever I can get my hands on, and to me, this was like stories come to life. I get to sit there and ask them any question.

I like under the sun and get to be really nosy. And then I discovered people are super open and willing to help other people. And it honestly snowballed from there and I was like, oh, I'll just reach out to people I know. And that was the first kind of like first 10, 20 episodes I did. And then I was like, oh, I'll reach out to people that they know and ask them to introduce me. And honestly, it's snowballed from there. I still do that. I still ask every single guest okay, who should I chat to?

That, you think, is really good. And we're here 334, 335 episodes in and we're still going strong and, to be honest, this really is only getting started. For me, this is something I will do indefinitely into the future because I absolutely love doing this. It's a fascinating business. It's a fascinating and I'll explore that as well. People, still people said it two days ago. People said to me podcasting. But that's it. Is it Like what do you mean? What do you do?

And I was like I have a podcast. And now, to save that nonsense, what I say now to people is I have a business media company. They're like oh, okay. Whereas if I say I have a podcast, they're like they almost look down there, nose that out and go a podcast, is that your job? Like, yes, yes, john, that is my job, so I'll explain that as well. Explain the monetization piece. So five lessons Think slow, act fast.

And I've been able to kind of like come up with that in the last two weeks right out of the book um, how big things get done. That was a book I read a few weeks ago and that was his whole thesis was to think slow, act fast. And I've learned that over the years, serial founders and serial entrepreneurs the second and third time they do it, they're much more methodical about how they approach the business.

So when host butlers was in the midst of lockdown, we lost literally half a million four weeks. I was like, right, need to move on to the next thing. Let's act real fast. I started building five tiny homes, five tiny cabins, to build them and put them on a site in the country. That way I could still operate in the cities in Dublin and cities all around the world.

Airbnb is now getting regulated so tightly that it's very, very difficult to do Airbnb and do it at a level that actually makes financial sense. And so I was like, right, I'm going to start my own site. I'm going to do tiny homes, because I'd seen this concept in the States. They were really taken off. I was like that is something I can do. So I acted super quick, too fast. In hindsight and this is a big lesson which I want to share with everybody I thought fast and acted fast.

I didn't add in the thing slow peace. So I invested a massive amount of money. I invested about 150,000 euro into these tiny cabins and I built them during lockdown. I got, I teamed up at a great company in Tupirary and we got five of them because that's how much money I had. I budgeted completely wrong. I didn't think slow enough to think through what might happen, and this is a big lesson you have to have a contingency in anything that you do.

I had run the budget too tight because, as COVID snapped we all remember what happened here Land prices went through the roof. So I was trying to bid on and buy land all across Ireland for these tiny homes. I must have looked at, I'd say, a couple of hundred potential plots of land, talked to 50 to 60 different partners trying to get it off the ground and what happened was land prices and house prices and property prices went through the roof and I literally got squeezed.

I got squeezed so tight because I wasn't able to then purchase the land to put the cabins on. So I ended up with five beautiful tiny homes and nowhere to put them. And then what happened was, as I was going through that process it was during COVID and lockdown I had all this time on my hands from like right, I'm not just going to sit around, I'm going to do more podcasts.

So I started publishing more and more podcasts and, as it started as I, weirdly, here's the lesson huge lesson as you focus on something more, the better it gets. How weird is that? Huh, when you put in more work, things get better. So I started working at the podcast almost like a job. Well, it was.

I approached it as a job during lockdown and I would reach out to all these people and I'd reach out to people I would never reached out to before because it was during lockdown and people had loads of time to chat to me. And it just started getting better and better guests and bigger and bigger guests and I started enjoying it more and I started to get a little bit better at it and people started to like it, enjoy it and start to message me and go this is really good, I enjoy your podcast.

I was like, oh, okay, might be something here, and that's lesson number two Trust your gut and play your own game. So I was like, I think there's something here. My gut was telling me right, there's definitely something here, but I didn't fully go into it yet. I kind of held back because I think it. Subconsciously, I was like, no, I need to make this cabin business work because, you know, going from the Airbnb management business, I need to translate that into something.

I can't take another hard left into a brand new industry where I don't know anything about it. But in hindsight, if I had literally transitioned from the Airbnb management business straight into the podcast, I'd be much further along than I am now. Hindsight's 2020. I don't regret anything, but you have to trust your gut and when your gut starts to tell you something, listen and that is something I've heard off so many guests you have to trust the gut and go with it.

The biggest thing is to play your own game. Stop looking at other people and going, oh well, they did this and they did that. And what happened was that I was like, oh, I'm going to play my own game. And once you start to walk the path, the path appears. That's a quote from Rumi and it's so true that, like you can see where it's going at the start, because I was like, oh, the podcast is fun and I honestly just viewed it as fun.

Then, during covid, and we got our first sponsor and curie's car store came on board and supported us, and I never forget that. So it's like, wow, this is, this is huge, and they were fundamental to my journey and they're a big part of my journey. I'll always be thankful to them for that, because they come on board and I was like, okay, this is a way of making some money. And during covid as well, we wasn't.

You know, the business was essentially shut down and surviving on fumes, so it was a massive help at the time. So you have to trust your gut and start playing your own game. I was still too focused on what other people were doing. I was looking at other property management companies, was looking at other property companies. I was like, oh, I need to be doing what they're doing.

And then, during covid, obviously everything exploded and people that had sites already in place suddenly started knocking up tiny homes like they were going out of fashion. So I ended up with the supply of tiny homes, but not the land and not the distribution channel, and this is why I learned so much. Now, on the podcast from founders, you'll hear me ask this question all the time as a second time founder what have you learned?

And what I learned is the first time, founder focuses on the product, the second time, founder focused on distribution. I made that mistake again. I was not a first time founder, I was not second time founder. I've found it many businesses, but I made that mistake of overlooking distribution. In my rush, in my haste to build this cool product, I overlooked distribution. And the distribution was well. The distribution was going to be Airbnb. I knew that like the back of my hand.

I knew Airbnb like no one else in Ireland and I let that kind of hubris override the fact that I didn't actually have the distribution arm at the base, which was land. So you always have to make sure that you're looking at the distribution of your product, not just your product. Thirdly, lesson number three experimentation is the future of business building. I am 100% sure of that. Everything that has happened since COVID has proved this out.

Businesses are now able to be much more agile, much more nimble. Businesses that are stuck in the past with large legacy systems, are having monumental issues now as the world is rapidly, rapidly changing. When I look around, I speak to founders who are still living in the 2019 era in their head. I realized they're not long for this world. Their businesses will not be here in five years time because they are thinking like it's 2019. The world has fundamentally changed. We live in a new era.

Remote working whether you love it or hate, it is here to stay. The world is fundamentally changed. The work week has fundamentally changed. People are now working different. They are in generally, they're at home Mondays and Fridays and they're working in the office Tuesday, wednesday, thursday. What does that mean for cities? What does that mean for commuting? What does that mean for transport?

What does that mean for city center businesses who, on a Monday and Friday, have no supply of people? Who knows? But it means a lot and you now have to experiment and see right. What do we do on a Monday and Friday? Do we flip our premises into something else? When I rock around Dublin now, I see a very, very different city. Something is changing in the world. A lot of things are changing, but a lot of people are still living like it's 2019.

So you need to start experimenting and this is why I constantly run experiments. Now, on the podcast, you'll hear me change up the messaging. You'll hear me try a different platform. You'll hear me try different episodes lens You'll hear me try releasing on different days. You'll hear me increasing the frequency. So this season we've increased the frequency to three a week. That's all done to test, to test, check, see what the result is, test again, check, see what the result is.

Experimentation is the future of business. I am 1000% sure on that. Lesson number four Live goes on seasons. Sometimes it's spring and summer, sometimes it's winter and autumn. You have to recognize that life is constantly in flux and you have to understand and be self-aware enough to know what season you are in. So in my last business, I built it to be a very, very good business and I had entered the summer season. I had incredible staff. I wouldn't even call them staff.

I called them like partners Claire and Rafa. They were super at what they did and they had become essentially partners in the business. They ran 50% of the business each and essentially I got to the point where it was just running perfectly. But you never know how long those seasons will last. And when those seasons are there, you need to work like hell. You need to double the intensity, not relax, not get distracted.

You need to double the intensity and work with an intensity and an urgency that befits your good fortune, because you finally got it to a place whereby now is not the time to rest. Now is the time to double down and go all in and start working even harder, and then, when it is spring and summer, you must recognize that will not last forever. There will come a time where you will enter an autumn and a winter. For example, in COVID, a lot of businesses went into autumn and winter.

My business went into a winter. A lot of people's businesses went into a winter. I personally went into a winter through a number of tragedies that came into my life at that time, and a lot of these things can compound on top of each other. If one of these things happens in isolation, you're able to deal with it and you're able to bounce back much quicker. But unfortunately life is like that. Sometimes Things do compound in a way that can make it hard to take. There's a number.

I won't come to it now, but there was a number of massive life traumas that I experienced during that time and, on top of losing the business, it definitely did shatter my confidence completely, and I think it's really only now, I would say in the last six months, where I've got that confidence back, and that comes honestly through hard work and through working on yourself and through being able to be honest with yourself and be able to shut down things and be able to go.

Now is the time to move forward with full, maximum intensity, and that can be very, very difficult to let go of the past. It can be very, very difficult to let go of what's worked for you. Previously. I was constantly in the mode of like, how can I get back into the property game? I love the property game. I love property. I still watch so much property content on all the time and I will go back into the property game at some time, but not in the way I was.

That was an incredibly grueling, tough business. That is not something you do for a very long time, but I held on too long and didn't move on. I went into the cabins business, which was just essentially a slight tweak on the same idea. Could I have pulled it off? Yes, but should I have entered it? No, and it's all about being able to be honest with yourself and to be able to look at things from a very, very, um, unemotional standpoint. So life goes in seasons.

You look at autumns and winters, but you also spring and summers, and now you're entering a spring. I feel I'm entering the spring season of my life whereby things are good, energy is there, things are starting to happen in a really positive way, the sun starting to come out, and it's just things are happening. I feel like I am on the right path. And that brings me on nicely to point number five. You have to survive to thrive.

At no point did I think about quitting being an entrepreneur, at no point did I think about maybe it's time to get a job, despite all the pressure, despite the financial pressure, despite the societal pressure, despite all the like, just the general pressure you put on yourself and your head, of all the internal narrative, internal monologue that you bring into your head, that it's the founders that survive, that thrive. And I never thought about quitting.

I never thought about giving up the entrepreneurial life. I know this is what I want to do for the rest of my life. My businesses will change and what I do will change. But I know I will always work for myself and I know just by being in the game long enough, you increase your luck surface area so that the timing is right. I feel something happening in this media space that I'm in now. There's something different happening. I can't put my finger on it right now.

I can't tell you exactly what it is. I have strategies and plans. I'm a very tactical person now, compared to before. I have a 10 year plan, a five year plan, a three year plan, a one year plan, and that's broken down into quarters. I am methodical. That will change fundamentally. That is not going to go in a straight line. Business and life does not go like that. It is not realistic.

But you have to have plans and you have to have goals and visions of how you want to get there, because otherwise how do you know where you're going? It's like driving to an end destination with no Google Maps on. You're just driving randomly. If you're going on a journey, no destination, how do you even know when you got there? How do you even know if you're going the right direction?

So we have to have plans and you have to be able to just stay in the game, that I cannot stress that enough for founders. You have to be able to stay in the game. You don't leverage yourself so much. That's why, on the podcast I know, talk about the brain, the body and the business, in that order, because you got to have your brain in the correct state, and by your brain I mean your mental health, how you think about it, how you talk about yourself, your mental fitness.

We don't talk about mental fitness enough. We talk about going to the gym, doing 5Ks, doing high rocks, doing track lines, all that kind of stuff, but very rarely do you think of someone going. Yes, I'm mentally training, so I train mentally. I go to a psychologist, therapist, call it whatever you want, every second week and it is massively beneficial and I have done that over a year and it is hugely beneficial, and I went to someone during COVID as well and when I started doing that.

It just gives me the perspective and the ability to work on myself and work on what I actually want, and it is hugely, hugely beneficial and, to be honest, that is helping me to survive, to thrive, because you have to have everything in sync this day of the founder being this person who works for 14 hours a day and just grinds themselves to a halt. You hear these stories all the time. They worked all the time and I hear this from founders still.

You know, I worked for the last 10 years at this business and then I sold it and I always asked them the question how do you feel now? I don't feel anything. They've just lost themselves to the game. They've lost themselves to the business of just building a business Along the way. They didn't check in with themselves and go is this what I want to do? Am I building this? Because I want to, and it's such a cliche, but you have to enjoy the journey.

This is one of the big cliches and as you do, as I've spoken to hundreds of founders now, you realize that so many of the cliches are true. But enjoying the journey is the goal. That is the goal. The goal is to be happy more days than you're not. It's not realistic to say you're going to be happy every single day. Being a founder, working with yourself, is immensely difficult, but the alternative is immensely difficult as well. So you've got to know what your win is.

You've got to play your own game. You've got to know what is my win. What does a win look like? And that's why I always ask that people that question what's the long term goal here? And that always kind of baffles me. When people are like, oh, I don't know, just keep doing it. That is an answer, but to what end? Is always where I want to go with it. That's where I always want to figure out, like, where do people want to take their business?

Because if you're just doing it to do it, how will you know when you've won? How will you know when the success is there? It's very, very hard for you to be able to actually say what the success is. When you get to that point, you have to know what success is. If you're wondering what the noise is, it's quite late and I'm recording this when someone just came in to try and clean the building, so excuse the slight noise interruption. So there are my five lessons.

That's kind of my cue to wrap it up, because I'm going to do a full. It's probably been an hour long. We might actually do a live event. Actually, you know what? We will do a live event for it. I will do a live pod with myself. It will more than likely be late April, early May, so chalk that down in your diaries as an event. We'll do it here in Dublin and we'll invite like a live studio audience to come and listen to that as well.

We'll have me and we'll probably bring in a great founder as well to talk to me. So that is it. That is my five lessons from five years of doing the Entrepreneur Experiment podcast. Thank you to so many people who reached out this week and sent me incredible messages. It's cool, it's really cool. I love this now because five years is quite a long time. In the founder space there's people I've chatted to five years ago.

I chatted to one founder today, luke Mackie, and he was building a completely different business five years ago and now he's one of the hottest prospects in Ireland with his company, koda. That raised over 7 million euro and they are on a rocket ship trajectory and it's beautiful to see that journey evolve over the last five years. It also shows you what's possible. It reminds you what's possible. So that is five lessons from five years of doing the Entrepreneur Experiment podcast.

I will be sitting here with you in five years time and we will be recapping the last 10 years of the Entrepreneur Experiment podcast. What I think I might do as a novelty I think I'll record an episode in the next couple of weeks projecting into the future. I'll record an episode that we release in five years time and we'll see how close I am to predicting the future.

I will record an episode to say what I'm going to be doing in five years, where the podcast will be, and I think it will just be a little bit of fun. If you're not having fun, what's the point? There you go. That is five lessons. Remember survive to thrive. I'll see you back here in a couple of days for a brand new episode.