#22 - (Solo) Lessons from Losing £16,000

Dean:

I do not care who you are. Losing 16 k, that's not a good time. Welcome to episode 22 of Work Worth Doing with your boy, Dean. Today, we're gonna dive into a shortcoming of mine where, as you might guess, I lost $16 and two lessons that we can extrapolate from my particular failure in this instance. You might be joining because you are looking for inspiration to help you with leaving your 9 to 5.

Dean:

You might be already on the way and you want practical advice for handling some of the crazy shit that comes your way when you are a business owner. It's a lonely, hard, difficult road at times. Wherever you are on that spectrum, I think today's episode is gonna be very helpful for you. As you may know already if you've listened to a previous episode, my goal is to help anyone who is in the same position I was which was stuck in a 9 to 5 with dreams and aspirations of living a different life. I really do believe that all of us, all of us have it within us to, at the very least, create a cash flowing business that can sustain us.

Dean:

That is what I believe at the very least. And in this particular episode, we're gonna talk about a particular setback that I had at the beginning of my business and it was a 16 k setback. So not exactly particularly nice setback nor is any setback. But this one, it definitely stung. And what I plan for you to take away from this is how to prevent and handle the inevitable setbacks to come your way.

Dean:

Because believe me, they be common. You might remember if you've listened to the previous solo episode that it was when I was 32,000 feet in the air on the way to Egypt with a beer. This particular one I'm recording back in London, I have actually decided to go back to Egypt and it is truly the luxury of being your own boss and I try and share this type of thing to encourage you if you're on the way to that that good things will befall you if you stay this course. You will be able to go on holiday as and when you please. And it sounds like a small luxury to be able to do that And there's a whole list of other things you can be grateful for in your life, for sure.

Dean:

But believe me, waking up with the choice to do as you please on any day, that, to me, is worth fighting for. It's worth grafting for. It's worth sticking through some of the crazy setbacks that will come your way. So let's get into them. Let me tell you the story of how I lost 16 ks and what you can take from this story to both prevent and handle setbacks that come your way.

Dean:

So very quickly, the story. As you may have known if you've listened to episode 1 or really know anything about my story or followed me on Instagram at all is that the vehicle that I chose to leave my very high paying comfortable sales job was property Now how did I get into property? I bought a course I walked in to an event and got sold a course. Amazing. And when somebody is selling you a course, what is their intention?

Dean:

Their intention is to make a sale. And so, naturally speaking, they may only illuminate some of the more positive aspects of what will befall you should you buy this course. Now, this is totally understandable. When you are an education company, your goal is to sell courses. And spending too much time on all of the negative aspects and what the road ahead is truly like can be detrimental to the sales that you need to make.

Dean:

So naturally, I don't begrudge them for doing that. Although I think my issue with these course selling machines is that they unfortunately find their way into the hands of people who are very, very desperate. People working in very low paying jobs who are eager to get away from that and eager to find a new life, and they're willing to do anything to get it. But they just don't know what to do in steps the course seller. And so, I think it's a it's a good industry.

Dean:

It does change lives, but unfortunately, when there's a lot of capital that needs to be put upfront to buy the course, as in this case, it can leave a trail of dead bodies behind, metaphorically, of course. So why am I saying this? I'm saying it because when I bought that course, what happened to me was I had very very misaligned expectations. Now, this this is not to lay all the blame at the foot of these people selling the course because I am where I am now because of it. The blame also sits with me, to some degree.

Dean:

Why? Because I would say one of my weaknesses is that I am somewhat impulsive and somewhat impatient. When I want something, I want it yesterday. And this is both good and bad in the realm of entrepreneurship. And so, when I bought this property course, I was expecting to make loads and loads of money straight away.

Dean:

Now, this was always going to take longer than that, but the combination of them telling me pretty much predominantly the outlier stories of somebody who has smashed it after buying this course, combined with my impatient impulsiveness led to my expectations being all over the place. So what happened was I bought the course, got the information, went to get my first property deal. Now what did I do? I bought it off a sourcer. Now sourcers are people who sell deals.

Dean:

They find a deal, they don't want to invest the capital and take the risk themselves, so they sell it to other people. Insteps, a hungry, impatient Dean Riley looking for freedom beyond his 9 to 5. So when you buy a deal, it costs you money. You have to pay upfront for the sourcing fee. You have to pay for the staging of the property so you can use it in your Airbnb business.

Dean:

1st month's rent, deposit, and 1,000 and 1,000 and 1,000 on the staging. All the furniture, the cushions, the blankets, the lampshades, it adds up. And so, I bought all this after buying the course speaking to the sourcer with my impatience and I spent all this money it totaled to 16 ks now What could possibly go wrong from there? I'm gonna make that money back real soon according to the sourcer all this is going to feed its way back to me in the course of about 9 to 12 months. Month 1 rolls around.

Dean:

Another month's rent is due to the tune of I think it was 1200. How much did they earn from me on the management of the property through Airbnb and Booking dotcom? Means £600. So what does that mean for Aldine 16 k? Instead of going down closer to 15, it actually goes up to 16.6 k.

Dean:

I'm now in more deaths. Month 2 rolls around. The same thing happens again. Dean starts to freak out at this point. Dean starts to realize that he's fucked up.

Dean:

He done fucked up. Why? Because of the reasons I mentioned earlier about my misaligned expectations and my eagerness to get away from my 9 to 5. So naturally, at this point I was heavily fearful. I was worried as to what the coming months ahead held for me.

Dean:

And I was also very critical of myself in this period, in this January February period of 2023. This is not that long ago, you know, this is very recent memory for you and for me that period of that winter. And it was scary. It was it was really scary. I I would not recommend this to anyone, to be in a position where you've invested a good chunk of your own money into what you believe to be something that will make you not only that money back but more money, to then only see it, not even just break even, but go the other way.

Dean:

That's a very scary place to be. And so before I kind of tell you how that panned out, I wanna just zoom into lesson 1 of 2, which is what you can take from this. What could we learn from this particular shortcoming that I had? And when I look back on this, the biggest thing that I got wrong here was not expecting any failure. You've probably heard a 1000000 times that, like, 90 something percent of businesses fail within the 1st 12 months or 3 years or whatever.

Dean:

I don't know what the exact statistic, but you've heard. You know what I'm talking about. Businesses fail. Ideas fail. And me not expecting the failure was lesson 1, lesson 1 of 2.

Dean:

And as you'll see when we get to lesson 2, lesson 2 is more about the aftermath of the failures. So let's just stick on lesson 1 for now, the expectation of the failure. With having an investment, like, investments go wrong sometimes, you know. And I was I was a little bit green around the ears, let's just say. And as I've mentioned to you, I am impatient and impulsive, at least I was to a larger degree at that point.

Dean:

And I wasn't expecting anything to go wrong. All I was expecting was, This is a great strategy. This person who sold me this deal, of course has done the numbers accurately. I don't need to do the level of due diligence that I think and that I know I probably should because I have this sorcerer who sold me this deal, why would they lie? And it was a melting pot of misaligned expectations on my side and slightly inflated numbers on the side of the sourcer.

Dean:

And had I been going into this whole venture expecting that, 'look, shit goes wrong. Shit doesn't always go as you think it will go.' Had I truly understood that and carried that with me, this not only would this loss not have hurt as much but I probably wouldn't have even got into the deal to begin with. Because when you're investing capital, you know, you look at senior investors, hedge funds, trust funds, all these institutions where their sole purpose is to allocate capital in a way that's going to increase over time. Like, they don't they're very calculated with where they allocate those funds. And I needed to be a bit more like that.

Dean:

I don't need to be, like, super stringent, but Jesus, I should have been more thoughtful about this. And on top of that, just expecting that like any investment, like any business, there's a huge chance that it might not work. And so had I ever remembered those, I might have been in good stead. And my expectations could have saved me some heartache here and also could have saved me some money. Let's be real.

Dean:

So if you think about it in the lens of sales, something that's carried me through a lot of the harder times of trying to get clients in property was my ability to take a no. You know, you've probably heard the phrase, every no gets you closer to a yes. It's fucking true. You have to be able to just take those noes on the chin. And in the same breath here, you have to just be able to take those failures on the chin.

Dean:

They're gonna happen. Look at any business owner who's ever done anything. They've made failures. They are where they are now. Elon Musk, right, he is where he is now because of all the shortcomings that he's had.

Dean:

All the ideas that he's probably had within Tesla, within SpaceX, you know, that didn't work out. All the initiatives within there. You just see the big company on the outside, the big roaring success. But that is a company that, like every other company, has a backlog of failures. There's just no way around it.

Dean:

And so, that's lesson 1: expecting that you will make failures and being ready for them. Being ready for shit hitting the fan and not being so surprised by it like I was. So lesson 1 of 2, what is lesson 1? Expect that you are going to fail. You will have things that won't go your way.

Dean:

It is inevitable. So, expect them and then when they land and they do arrive on your doorstep they will not carry the same level of punch as they might have initially and therefore you won't be as clouded emotionally when they happen. Sounds obvious but Jesus Christ when I've kind of walked through my business with this type of approach something comes across my desk, something happens on a day, I kind of just take it in my stride a bit more now. I'm like, okay, this is business, this is the price of entry, Things fuck up. So lesson 1: Expect you will fail.

Dean:

So where are we at now in the story? I have been tormented by my mistakes. I am now waking up daily. You know, I would wake up in the morning, and it would be as if this cloud of fear, regret, judgement, panic would all wash over me. From the moment I would rise, by the way, every every morning I would wake up and just immediately be consumed by this financial hole I had dug myself in.

Dean:

I've mentioned this before, financial stress is a very unique, all encompassing type of stress. It's not particularly pleasant. So I wouldn't recommend it. Definitely wouldn't be recommending it. I was heavily critical of myself.

Dean:

I wasn't being very kind to myself or being very self compassionate, which is understandable when we make a big mistake that usually our inner critic tends to come in and give its assessment of the lay of the land and our decisions leading us to that point. But in hindsight when I think back to that period it reminds me a lot of a book that I had read. I'll come back to this story quickly but I want to explain to you this book and what I took from it and how it relates to this. The book is called The Four Agreements. If you've never heard of it, it's an incredible book.

Dean:

I would recommend the audiobook version, which I listened to on Audible. The Four Agreements are four agreements that you make with yourself to effectively live a better life. What the author, Don Miguel Ruiz, talks about in the book is the concept of this thing called 'Judge'. Now, the Judge is this all knowing, all seeing voice that lives inside your and my head that gives its assessment on every single thing that transpires in your life. What somebody has worn today in the office, what your neighbor on the bus sitting beside you was listening to on their ipod, what you were thinking last night, what you said to a friend, what your friend said to you, what your friend ordered for dinner, what the weather is like, what that neighbour's car looks like, and everything in between.

Dean:

It gives this continuous narrative, this continuous assessment of how the world is, how people are, and above all else how you are. And the George is very often very negative. And my George, as it relates to this particular part of my life, was heavily critical of myself. Heavily critical. So I would recommend that book, the Four Agreements', if you haven't read it.

Dean:

But the judge, in my head, at that period was brutal. So on top of the feeling of all this financial stress, I was very scared. I was very in my own head. I just didn't want to be there anymore. I remember being with a friend in Hackney, Sean and I.

Dean:

We were in a bar called the 3 compasses and at this point I was very low. I was a few months into continually losing money and showing no signs of getting it back. I was in this bar called The Three Compasses having a Guinness with Sean and I was crying. I was in tears because it was all so much and I hadn't really quite shared just how much I was going through at that period. And I was in tears just being like, 'man I can't do this anymore.

Dean:

I don't wanna I don't wanna keep doing this. I'm I'm scared. I'm I'm lost. And I I really meant it, you know. I wasn't looking for sympathy.

Dean:

I was, well, you know, in hindsight, I I was looking for I was just looking to be rescued. I wanted to get out of there. But through conversations like that, one I had with him that night, and through having a strong mentor with me as well, I realized that this was just a dip and that this was a point that I would look back on if I continue. I'll round this off with another particular poignant call I had with a mentor around that time. And I kind of said the same thing to him about my feeling of, 'I just want to stop.

Dean:

This is too much. I fucked up.' And he said, you know those phrases that somebody says and for some reason it just always stays in your mind? Like a phrase, like a that they probably said off the cuff. And he said to me, Justine, stay in the fucking game. That's how you win.

Dean:

And it just stuck with me. I was like, all I have to do is zoom out and stay in the game. Zoom out and look at this over the course of the year rather than the shit week. And and as I weathered the storm then I started to realize that, hey, this is actually part of my story. And as it relates to this specific property what I did was meticulously went through every single facet of this property as to how we could market it better, how we could increase the prices, how I could decrease my costs, all up until the point where I could give back the lease.

Dean:

Because I didn't wanna keep this property. It was a dud. Shouldn't have done it. So all I needed to do was just ride it out until the lease was over and give it back, and minimise my losses along the way. And so I did.

Dean:

And I as January February turned into the summer and we got ourselves closer to September, I finally got to get rid of that bad boy. Give it back. Thank the Lord. And so, as I think back now recapping this story, what lesson 2 is to me what I took from this is how important our reaction is and how we react along with expecting the failure to begin with and trying to prevent it, they will happen. And so how we react is the important takeaway here and lesson 2 in this particular story.

Dean:

Because in that phase of my entrepreneurial journey, I could have quit, I could have tossed in the towel. And it was I mean, believe me, that option was ripe and ready for the taking. But I just knew that it wasn't the right move. I knew I couldn't stop. I wanted to.

Dean:

I wanted to rid myself of the pain I was feeling, but I knew I couldn't stop. And thanks to the support of my friend and thanks to the support of my mentor and my subsequent reaction and handling of the situation, we got out of there. And so what I would say to you as you enter a rocky period, which you will inevitably come into because, like I said, you can prevent them and expect them to minimize how they feel when they come, But ultimately they will come and your reaction to them is what will determine where you end up. So again, just to recap, you can expect that these things will come and so you can mitigate, prevent, get in the way of things happening. But invariably, business is unpredictable, life is unpredictable, and things will happen anyway, so you have to be prepared to take a deep breath and react as the situation requires you to.

Dean:

And that's it. Crazy little lesson, 16 ks down to Suwanee. Not ideal, but we got it back. We got it back. We're back.

Dean:

We are back. Looking ahead to 2025, the way I've been doing this show is probably a little bit more overproduced than it needs to be at the size it's at. You know, you see podcasts and long form audio and video, and it can be cool to do it in a studio, and it's fun to do it in a nice setting. Do not get me wrong. But ultimately, I would like to just do more and have more conversations and make them more conversational.

Dean:

I think what I've been guilty of is trying to make them very precise and structured. I just want to have interesting conversations with interesting people that you can either just simply enjoy listening to or, at the best case, probably walk away with 2 or 3 things that you can put in your back pocket for when you need them. That's what I can realistically hope with a podcast. A podcast isn't going to change someone's life. It can just be something nice that you listen to, and that gives you 1, 2, maybe 3 things to walk away with.

Dean:

So thank you for being along the journey so far. I do appreciate it, no matter how long you've been here. If you are enjoying it, my ask to you is to rate it. That's a huge way to help. I'm trying to accumulate some more ratings, so if you haven't done that, please do.

Dean:

Up in the top left, go on, Give it a go. Click it. And then on YouTube as well, if you're ever watching them on YouTube, subscribing there is a nice way to help me in return as well. To round things off, I wish you the very best for the Christmas period. I wish you the very best for the New Year.

Dean:

I wish you the very best for 2025. It's gonna be a good year. It's gonna be your fucking year. Let's go.

#22 - (Solo) Lessons from Losing £16,000
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