In short
A FI (financial independence) roundtable on “Mistakes Were Made,” mixing major financial errors and human life mistakes, arguing that you can recover and learn—especially by using others’ mistakes.
Guests (backgrounds)
Katie Donegan (actuary training at Deloitte; later FI-focused index investing); Alan Donegan (longtime friend/host participant; FI achieved despite early investing setbacks); Brad (host; FI advocate; discusses index funds and “FU money” framing).
Key claims
Smooth paths are rare; catastrophic mistakes don’t prevent FI if you keep saving and learn. “Magic” investing secrets don’t exist—boring index funds do. High fees and active management can quietly derail progress. Confidence and growth mindset matter; comparison and perfectionism worsen learning.
Notable examples
Alan invested £7,000 life savings into a tech managed growth fund right before the dot-com crash, losing ~90% and avoiding stocks for 13 years. Katie was sold actively managed funds with ~2.71% + 3% entry load and heavy bond allocation after a “can you lose money?” risk questionnaire; staying with it would have cost about £1 million. Alan and his brother speculated in North Carolina golf-course properties using interest-only loans and balloon payments; the 2008 glut left them stressed for over a decade, with properties still far below purchase price. Katie also regrets turning down promising netball opportunities to focus only on studies, illustrating “path not taken” and fixed mindset/perfectionism.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Importance of Learning from Mistakes
0:55 to 3:00
Discussion on the value of sharing and learning from financial and life mistakes.
“And with that, welcome to Choose That Fine.”
Alan's Investment Mistake and Its Impact
3:00 to 6:10
Alan shares a significant financial mistake made in his youth and its long-term effects.
“So I would love you to get the value out of my mistake because I've already paid the price.”
Brad's Early Investing Lessons
6:10 to 8:20
Brad recounts his early investment experiences and the lessons learned from them.
“And I thought property was the way for a long time because I was scared of stocks.”
The Myth of Secret Investment Strategies
8:20 to 12:20
Discussion on the misconception of exclusive investment knowledge and the reality of index funds.
“And I think that's really, like I said, the meta lesson here.”
Katie's Introduction to Investing
12:20 to 14:06
Katie shares her initial experiences and thoughts about investing during her early career.
“How did it impact you in terms of your thoughts about the stock market and investing and it didn't make you run away or what happened?”
Navigating the Investment Landscape
14:06 to 18:17
Learn about the initial challenges and mistakes made in investing.
The Cost of Bad Advice
18:17 to 18:39
Discover how poor investment choices could have cost over a million pounds.
“How much would that mistake have been worth?”
The Shift to Index Funds
18:39 to 20:05
Understand the advantages of index funds over actively managed investments.
“And we'd still be working because we would think this FI stuff doesn't work because it's not growing enough to be able to live off.”
Real Estate Speculation Gone Wrong
20:05 to 25:58
Explore the pitfalls of real estate speculation and lessons learned.
“It's speculation, ultimately, is what it boils down to.”
Writing a Book on Business Mismanagement
25:58 to 26:12
Hear an amusing story about writing a critical book on a former boss and the consequences.
“Because we can all laugh at Alan for a little bit.”
Show all 25 chapters
Facing Truth at Work
26:12 to 28:00
Learn about the importance of addressing issues directly in a work environment.
“The boss was a bit unscrupulous, did things that I think were wrong.”
The Challenge of Speaking Truth to Power
28:00 to 29:50
Learn about the difficulties of confronting authority figures and the role of financial independence in gaining the courage to do so.
“embarrassment is around yeah maybe I should have spoken up more at work and told him maybe I I shouldn't have done it on the work laptop.”
Reflection on Mistakes and Growth
29:50 to 31:40
Discover how past mistakes can lead to valuable lessons and insights about personal growth.
“So, I mean, Alan, I don't know exactly how old you were, but I don't know that you would have necessarily had some other option or recourse.”
The Choice Between Sports and Studies
31:40 to 36:40
Explore the impact of personal choices on self-identity and career paths, focusing on sports and academic pursuits.
“And yeah, I think having that power helps.”
The Importance of Confidence and Mindset
36:40 to 42:00
Examine how confidence and mindset shape personal success, using examples from sports and academics.
“And I think it's hard not to go down that.”
Embracing Mistakes and Imposter Syndrome
42:00 to 44:30
Learn how to navigate personal identity and imposter syndrome through the lens of mistakes.
“I'm not, even though you were sporty, as you would say, like you cared about your studies.”
The Value of Making Mistakes
44:30 to 46:40
Understand the importance of learning from mistakes for personal and professional growth.
“So again, Katie, like that's a whole lot of like random little lessons that I gleaned from just your one mistake.”
The Importance of Honesty in Communication
46:40 to 48:50
Discover the benefits of being direct and honest in your interactions to avoid conflict.
“And I just very simply would not have been ready had I not made those mistakes.”
Setting Boundaries and Saying No
48:50 to 52:10
Learn techniques for saying no gracefully and honoring your own boundaries.
“And Alan's like, why are you not just ringing them?”
Speculative Investing Pitfalls
52:10 to 55:40
Understand the risks of speculative investments and how to avoid common traps.
“The classic version of that is always try.”
Building a Valuable Email List
55:40 to 56:00
Learn why capturing email addresses is crucial for business success.
“All right, Alan, what's up next on your list?”
The Importance of Building an Email List
56:00 to 58:01
Learn why building an email list is crucial for business success.
“I never captured people's email addresses.”
Overcoming Fear and Building Confidence
58:02 to 1:00:01
Discover how confidence impacts business growth and the importance of self-worth.
“So like, why would I ever want to enrich Mark Zuckerberg of all people?”
Negotiating Salaries and Self-Advocacy
1:00:02 to 1:02:01
Understand the importance of negotiation skills and advocating for your worth.
“And yeah, I think with confidence, I actually had one which is not negotiating my salary.”
Creating Fun and Positive Relationships in Business
1:02:02 to 1:04:19
Learn how fun and positivity can lead to business success and better relationships.
“one of the interesting things I learned a long time ago was they did an incredible study about why people choose suppliers.”
Transcript
Automatic transcript. May contain errors.0:00Hello and welcome to Choose a Fi. Today on the show we have my great friends Katie and Alan Donegan. This is a roundtable. We're calling it Mistakes Were Made dot dot dot. I think what's fun about an episode like this is the three of us go around and we talk about a lot of the financial mistakes we've made in our lives but also some life mistakes as well. I think what's so interesting about this is you might look at people who are Phi and think that it was just this straight path up and to the right and that everything was easy. That's very rarely the case, but yet people reach Phi and they live these wonderful lives.
0:37That makes this even more interesting. And frankly, you can learn from our mistakes. The wisest thing you can do is to learn from these mistakes. And I promise we're going to keep on making these mistakes. We all are. And we can all learn together. and move forward and enjoy our lives. I think you're really gonna enjoy this episode. And with that, welcome to Choose That Fine.
1:00Before we get started, I keep this podcast entirely ad-free for two reasons. First, this is a five podcast and I don't wanna promote products that I don't want you to buy in the first place. And second, I really like the clean listening experience of a show where you don't have to fast forward ads. To keep it ad-free, all I ask of you as a listener is the next time you open a travel rewards credit card. Go to choosefi.com slash cards. And with that, on to the show.
1:29Alan and Katie, it is good to see you guys. We just spent three weeks together in Richmond and you're in Istanbul now, right? Yeah. And time apart feels like much more elongated after spending that concentrated time. Yeah. We miss you and we miss being in Richmond. Yeah, that was great. It really was. And it makes you realize why we're doing this, right? Like, why are we pursuing FI? It's to live lives that we want to live into, right? To create lives that we want to live into. It was really wonderful to have you so close. Yeah. Future life goals, I think. Definitely. Yeah. And if there's one thing you want to do is buy back time to spend with people you love.
2:03Yeah. Indeed. Indeed. I'm going to paraphrase Alan and his wisdom here. So we are talking about mistakes. Why are we doing this? Because we've made lots of mistakes. The three of us have. Everybody's made mistakes. It's so easy to sometimes to look at people who are on a podcast or somebody famous or whomever and say, oh, their life is so charmed. It must have been easy or it must have been smooth sailing. And we are here to tell you, believe me, it is never smooth sailing. There are always issues. Honestly, that's part of the fun of life. I think that's part of the spice of life. And frankly, again, to paraphrase Alan, you can learn from our mistakes.
2:42and really the wisest thing we can do in life is learn from other people's mistakes. Obviously, the three of us and all of us out there are gonna keep making mistakes and maybe, just maybe, we can learn together. So yeah, we're gonna have a smattering of money mistakes and a lot of life mistakes, et cetera. Alan, I think you want to kick off our little round table here. Well, I think want is a strong word. We had a little pre-chat, didn't we? And I was like, I need to learn. Alan drew the short straw. I've been with Alan 21 years I've known this man over half of my life and yet I read two of the mistakes on his list and I was like I didn't know this this is kind of exciting there's stuff that I didn't know about Alan and it's things that are mistakes so this is exciting to hear so for everyone listening some of these mistakes some of them were just mistakes some of them cost us a lot of money some of them like really impacted our lives and so we've learned these lessons but to rinse the value out of the mistakes, well, it's a lot more valuable if we share them.
3:41So I would love you to get the value out of my mistake because I've already paid the price. So let's give it to you and share the value. Now, first mistake, we're going in with a relatively big one. I was 20-ish, 20 years old. I'd saved up all my summer holiday money, my work money. I had about seven grand. It was my life savings. At that time, quite a few years ago, don't tell anyone, at that time, it was enough for a house deposit. So it was a big chunk of cash. And my dad had the fancy advisor, the financial advisor came around, soft top car, fancy suit, came in, charmed us, talked about stocks and shares that have been going up ridiculously.
4:26and he persuaded me to invest my life savings in a high-tech managed growth stock fund right before the dot-com bubble. So the whole seven grand went all in tech socks because those were what were going through the roof. So if they've gone through the roof in the past, obviously they're going to keep doing that. So I put my whole seven grand in, it crashed a month or two later and my seven grand went down to less than a thousand. So I lost nearly 90 % of my money overnight and I held. But the interesting thing is even if you hold, if it's actively managed, the fund manager isn't holding because they're trading trying to get their way out of it.
5:11And five or six years later, it climbed back up to the heady heights, I think, of£1 ,200 compared to my£7 ,000 that I put in, and I sold it to go travelling and wrote it off. And I think my biggest failure was I didn't learn the lesson from the mistake. I was scared off investing in the stock market for 13 years. That was my biggest failure. It's not the fact I did it, it's the fact I didn't learn the lesson from it until much later. It's so easy to jump to that conclusion though isn't it because of all the stories that we hear of so and so losing their life savings in the stock market and the stock market is so risky and then you have that experience yourself and it's easy to fall into the conclusion oh stock market is risky this is not something i should ever touch ever again because it was so painful yeah that's wild 13 years alan so essentially all of your 20s and your mid 30s you did not invest in stocks because of this one catastrophic thing.
6:11Yes. And I thought property was the way for a long time because I was scared of stocks. So what else is there? There's only property. And I understand that. Has bricks, can touch bricks, has tenants. I get that. Whereas stocks and shares, after that experience, I just wrote off all stocks and shares. And there was actually a book that happened much later that said there are different ways to invest in the stock market. And I was like, what? Different waste. I don't even understand that. And that's when I realized, oh, I invested with an actively managed and basically stock picked in technology.
6:47So sector picked, stock picked. And I didn't understand that if I'd have just bought an index fund and rode out the wave. Yeah. But you learn the lesson a lot later. Should we check what your seven grand would have been worth now if you just we are not going down the opportunity cost scenario because i wonder how many millions of dollars extra i'd have if i didn't make the mistakes that i have and i think about that sometimes but yeah jokes aside that would be interesting to know now some of the mistakes that we've made that we'll talk about today we have gone and worked out what they cost us in order to help other people to say look this can have an impact and to help other people learn from what we did but we don't do it to beat ourselves up we just there is a little bit of pain in the belly when it happens and you look at the number of zeros but you have to explain it to other people to help them understand like this is what it actually cost us in opportunity cost yeah i totally agree obviously i was i was getting there but i think the important part really one of the meta takeaways from this episode is the three of us have screwed up a whole lot And we are doing great, right?
7:58And all three of us are financially independent. We are living these incredible lives that I don't think, I don't want to speak for the two of you, but I know I could not have possibly dreamed that my life would be this great. And yeah, I think if I ran that opportunity cause just based on my first mistake alone, I suspect I would have an extra, like I said, probably seven figures in net worth. But the beautiful thing is you can make mistakes and you can make catastrophic mistakes and you can pick yourself back up and you can move on with your life and you can save money and you can learn the lessons and you can invest in index funds in this case and you move on and you're stronger and you're wiser.
8:35And I think that's really, like I said, the meta lesson here. Yeah, you've teased us with your first one, Brad. I feel like I want to know now. What is this? Tell us. I'm going to go to that in two seconds because I did have two others. It's funny. What's so amazing about an episode like this is as you're saying your first mistake, I literally jotted down two that I would not have remembered. I suspect my list is going to be dozens long by the time this hour is up. So as a, I think it was 19 year old, I had a summer internship at a investment firm as Solomon Smith Barney, which was a famous name back then.
9:11And I think they had their top stock picks. This was like 1999, so right before the dot-com implosion. I'm going to kick myself because I'll think of what the second one was, but I know WorldCom was one of the stocks. I didn't have a lot of money, needless to say, but I invested a little bit, maybe$300 to$500 in each of this WorldCom and this other stock because, oh, it's Smith Barney. These people know what they're talking about. It's one of their top 20 stock picks for the year. this has to be a slam dunk. And literally they both went bankrupt and they were gone within a year. So worth$0. There's a lesson there about a lot of people think there's some secret to investing.
9:52There's some like person behind the curtain who's pulling strings and who knows more that like, once you become wealthy or once you get to a certain echelon of knowledge or friends or connections or whatever that the magic unfolds to you. And I don't think that's true at all. Like now the three of us certainly like we're fairly wealthy. We're certainly very comfortable. Have you guys come across any magic investment secret that isn't altogether obvious of just basically invest in index funds? There's nothing that's come to us other than the standard like here's a bunch of get rich quick schemes.
10:30Like you always get those. The top stock picks do this, do that. They're always there, but there's no magic new doors open. And I think that bit of like the network and the friends, it sounds a bit like insider trading to me. Like you get to a certain level and then. And then someone like pulls you to one side and says, well, now that you've hit this certain net worth, now like we're going to reveal the secrets to you. It's so ridiculous. And it's funny because even intelligent, well-meaning people fall prey to this. I know I was chatting with one of my friends from my mastermind group and he was saying he lives in a little enclave that's a fairly wealthy enclave.
11:09And he was talking about like meeting these guys, I guess he was saying, these guys who used to be like, quote unquote, high level in finance in New York City. And it's like they have investment clubs and all this other stuff. And I'm like, oh, God, like my spidey sense is going off. I'm like, run as far and as fast as you possibly can. Like high level only means to me that they are high level salespeople. That's it. End of story. Because nobody can outperform the market over any appreciable period of time. Like it just means they probably were their college fraternity, like rush chair or something like they're the popular people and they're good salesmen and they're good at getting a lot of money for their firm.
11:48And that's what high level means. It doesn't mean they have some grand information because it simply doesn't exist. it also means they have more money to be able to lose so quite often the people who don't have any money want to aspire to do that but then they don't realize these people lose a lot of money as well and it's like a gamble up a gamble down and you just don't need it i am so excited by the lesson that boring index funds is the way to go i'm curious brad you said you'd even forgotten that that happened. So it didn't scar you. How did it impact you in terms of your thoughts about the stock market and investing and it didn't make you run away or what happened?
12:29It didn't. And it's funny because I had another lesson around the same time, which was I went in to another firm. It was like Chase Bank or something. And I don't even know if it was Chase. To be honest, it was the bank in the bottom of our office. And I had dutifully saved$2 ,000 to max out my Roth IRA. and I got sold a mutual fund that had this like horrible load. It was like a five or eight percent load or something crazy like that. Like ridiculous. Like it was just basically they saw me as prey. Here's like some 22 year old kid who walks in and it's just prey. I invested this money. I couldn't get it out.
13:05It was, you know, it was a nightmare. But I have to say on Lake Allen, I didn't get scared of investing. I think I just wanted to learn more. It did take me a long time to feel like I learned. It took me until I found JL Collins and the stock series. So it was probably almost 10 years later that I felt comfortable. I don't think I ever felt comfortable investing until I found out about, really found out about index funds. That doesn't mean I wasn't investing along the way because I was trying to put money into my 401k. I almost have like a, I can't remember what I did in my twenties and thirties.
13:38I really can't, which is hilarious, but it doesn't make for great podcasting. But yeah, I wasn't scared off from investing, but I just never felt comfortable. I really never did. Kitty, what about you? The two of us have talked about our, and I will get back to my big money mistake. Obviously, I still haven't mentioned that. But where were you in terms of like the mentality of investing in your 20s? The thing that comes to mind that happened in my 20s was I just started working at Deloitte. I was training to be an actuary and I felt probably quite nervous in general as to like figuring out my place at work and what was going on and I got a phone call whilst I was at work and this never happened like I'm junior the phone does not ring there's no one trying to talk to me and it was this guy and he said Katie have you ever thought about investing and the answer was yes I had because Alan and I had started trying to figure out we'd had this idea in our heads of buy an asset you need to buy assets and we were like how do you buy an asset where is the asset shop where do you find these things how does it work it's not next to Walmart there's no asset shop corner in Walmart if there was it'd be a lot easier so this guy rang me and said have you thought about investing and I was like yes yes I have and he's like okay like this is going to sound weird the way I say it was like come to my office and let's chat about it and he was a financial advisor and looking back I was just so naive that you know the first person that happened to ring me I was like okay cool let's go like I didn't think about vetting him I didn't look up who he worked for I just was like okay I'll like come along to your offices it's a 20 minute walk from where I work in London let me go and see what this guy is talking about and I think I was so trusting and so like okay tell me what to do and I do remember actually asking a couple of questions because Alan and I talked about investing in property so I was like oh what about property and of course he had his standard response to any of these sorts of objections of what he was going to suggest and I also remember I had read somewhere this idea of active versus passive investing and I remember raising that and being like oh what about the passive investing thing but I had no real understanding or concept of what that actually meant so it was very easy for him to convince me that his way of investing which was in actively managed funds was the way to go I didn't really know and I was like oh what about this and he's like no this is the way to go.
16:12Yeah you want the professionals you want someone choosing and the fees were outrageous they were 2.71 % plus a 3 % entry charge. So you lose 3 % just putting the money in. Then it was like 2.71 % ongoing through the advisor fee, the fund fee, the platform fee. No one knows this when you start. It's just like, oh, okay, a couple of percent. Surely that's okay. How or why would you know what a reasonable fee is? So I was like, okay, like, off we go. Let's Start with like£300 a month and we'll see what happens. Well, he gave you a survey first. Oh, yeah, the risk assessment questionnaire. Basically he asked, how comfortable are you with losing money?
16:54And I said, no, thank you very much. So I believe I was like 24, 26, something like that. He put me in two different funds. One of them was 50 % bonds and the other one, I can't even remember what it was, but I was heavily in bonds in my mid-20. because I'd said I didn't want to lose money, which he takes to mean, OK, this person is not going to be able to cope with any volatility. Let me put her more in bonds. And we see that with people so, so often is that advisor asks, are you OK with losing money? They say no. They say, OK, the stock market isn't for this person. They don't understand volatility.
17:34They're going to panic and sell. So let me put them heavily in bonds. We see that time and time and time again. and we just wish there was a way that I think that in their defense they're trying to follow the regulations and they have to ask your risk tolerance and they have to do all this stuff but is there an opportunity for them to educate their clients and say okay this is a feature of the stock market if you want long-term wealth over the decades you need to understand that these things are volatile but as long as you hold on for a good chunk of time you'll be fine That's what no one tells you because they just want to sell their funds, don't they?
18:14That's their objective. So what's the big reveal, Katie? How much would that mistake have been worth? Because we did the numbers because we wanted to show actually what it would be. Well, if we had carried on investing with him in the amounts that we did when we discovered index investing and fully went in and accelerated on our way to financial independence, it would have cost us one million pounds. Oh my God. Okay. $1.3 million we would be worse off. And we'd still be working because we would think this FI stuff doesn't work because it's not growing enough to be able to live off. Well, right.
18:49At a 2 % plus handicap each year. That's crazy. Which we were lucky enough that a couple of years after I started investing through him, we did a mini retirement and had a six-month honeymoon. And we were looking at this thing like, well, it hasn't grown. Let's just cash it in. So luckily we didn't continue investing with him and that was very fortunate. Yeah. And then by the time we got back, I read a book that talked about index investing and I was like, oh, okay, that's the way to do it. And then we changed direction. But if we just stayed with that guy, yeah, we wouldn't be financially independent.
19:25We'd be a million pounds worse off. Isn't that amazing? One decision would literally make the difference between living the life that you want and making it impossible. So easy lesson is this is why we talk about index funds. We are in the golden age of investing, all of us now. It is so cheap and it is so easy to invest in index funds. I personally like the exchange traded fund VTI from Vanguard. You can buy it anywhere. There should be no commissions or fees virtually anywhere you buy it. And that's where I put the vast majority of my net worth, just in VTI. And I sleep really easy at night now.
20:00So yeah, I think that's a hard fought lesson learned for all of us. So my big one, actually it's two. It's interesting. It's speculation, ultimately, is what it boils down to. So that's the umbrella. But the big one was in my mid-20s, a good friend of mine, my brother and I basically bought the speculated in buying real estate. We thought we were going to be real estate investors. I know now, of course, there are any number of ways to invest in real estate. But I think the way that I look at real estate investing now is think of it as a business. So I'm going to buy properties that I can rent that are cashflow positive, that are going to have net income.
20:40And over time, I'm going to grow my wealth. It's a get rich slowly thing. At that time, there was this crazy boom in these golf course communities throughout the Southeast of the United States. There were like these country club style golf course communities. They were popping up everywhere in North Carolina, Virginia, down South into Georgia and such. And we wound up going down to North Carolina and buying a couple of these pieces of property in this community. I still remember I bought the one piece of land. It was like around$90 ,000. The other one was around 80. I got interest only loans, five-year balloon payment, interest only loans.
21:21It's like the worst case scenario. And in and of itself, that would have been whatever$170 ,000 mistake, which would have been fairly easy to deal with. but what actually happened was maybe the worst possible scenario was we actually sold one of these things because it was this speculative fervor. We wound up getting in early, just like the typical speculation. We got in early. We're so smart. We know something. And this is all dripping with sarcasm. Of course, we're so smart. And then we were able to sell it. It's the greater fool theory, right? Just try to find some greater fool who's going to pay more for it.
21:55That's literally what speculation is and sold it for like some crazy profit. I forget. It was like 40, 50,$60 ,000, something like that in fairly short order. So what do we do? We buy more of these things. Of course we're geniuses. I think we wound up selling two of them at that time. And I don't remember exactly how many we ultimately wound up owning between the three of us. And I owned one or two just myself. So it was like, this was a compounding issue that I mean, it wound up being probably six or seven of these properties that we owned. And again, interest only loans with a balloon payment after five years.
22:30So impending doom. And then there was a glut of these properties on the market. It was right around the 2008 crash. It was like literally everything that could have gone wrong went wrong. And I mean, we deserved it, frankly, we just absolutely stupid speculators at the absolute wrong time. But I don't know if this smart or not, but I'd never foreclosed on these things. I just kept dutifully paying them. I mean, for years and years and years, well over a decade, probably 15 years, we were making the payments on these things. We eventually refinanced and got et cetera, et cetera. But I finally paid them off.
23:06I forget exactly. Sometime after Choose a Vi existed. I mean, this literally was like into like 2020 or beyond. And I lost a lot of sleep over this, guys. Like this was maybe the biggest stress in my life for a solid decade or more. It was horrible because I mean, frankly, I was saving money. Obviously I was on the path to fi, et cetera, but this was looming over my head. And also it was, man, I made this really stupid mistake and I can't believe I did this. There were some positives. I'm like, I'm going to find a way out. I'm going to figure this out. I'm smart enough to figure it out. But this was something that stressed me out for a very long time.
23:42so what happened did you end up selling them like what happened to these places yeah i wound up paying them all off the stress at least was stopped i think frankly we actually still own a couple of them i sold the two that i owned from one of these kind of like again to their credit these like vulture companies who like send you a postcard in the mail like hey we'll buy this from you for x and i hadn't been able to sell them for as long as i can remember and i just wanted to wipe my hands of it and just be done. And I think still to this day, those properties are still down like 70 % off of what I bought them for.
24:19It's like the land that time forgot down there because this property, they sold a thousand of these lots in this middle of nowhere place in North Carolina. And there are a couple of hundred houses and they're beautiful and it's this nice golf course, but it's just this supply glut that I think will never, never clear like in a hundred years, probably. So it was about the worst case of speculation, as you can imagine. So you spent 10, 12 years paying these things off to only get a 30 % return, plus the interest you paid. Well, you say return, no, it's not return. Return is very interesting. It's the wrong word.
25:00Yes. Had I invested that money, again, I've never run the numbers because I fear it would compounded, especially over those years, right? We're talking about like a 15 year run. So I suspect at minimum, there would have been over a million dollars that my net worth would have been positive when it basically was neutral or negative on that particular item. So yeah, I mean, it's, that is about as catastrophic of a mistake as you could possibly make. And yet I still reached FI in my late thirties. So it's not all doom and gloom, but it's pretty interesting. I love that because I really would love everyone listening to this to hear how many mistakes we've all made and how much we've struggled with this stuff.
25:41And then you can still come out on top. If your savings rate is good, if you just learn a few simple lessons, you can still come out on top. Yeah, indeed. So that was a very long-winded one. But yeah, that without question is my biggest mistake of all time. Unbelievable. I love it. I'm going to go for a life one next. Because we can all laugh at Alan for a little bit. Is that how we treat people when they make mistakes? No, we should be kind to them. But I don't think I've really told that many people. So I was working for a firm, didn't like the boss. The boss was a bit unscrupulous, did things that I think were wrong.
26:19And I couldn't really tell anyone or do anything with it. So I decided to write a book called How Not to Run a Business. and I decided to write that book about him and my dad and like a bunch of other people I'd worked for with all the things that I thought they did daft running a business and can you guess what laptop I used to write oh no the company laptop I used the company laptop like what an idiot I They used the company laptop. They found it. They fired me. They realized that they couldn't fire me for having an opinion because I hadn't done anything with it. So actually then they had to unwind the firing and I got paid to leave and like paid some go away silence money.
27:10Oh, wow. So I wrote a book called How Not to Run a Business on the Work Laptop and based it on my boss. Oh, my God. what happened to the book yeah where's the book i don't know i probably could dig around in my old files somewhere i don't even know whether i had it or whether it was just on the computer laptop on the work laptop and then got deleted we gotta find it do you feel embarrassed about this yes i am perspiring i've gone red i am uncomfortable because i feel like an idiot because of doing it on the laptop not the fact that you wrote it no kind of the fact that I wrote it my plan was to anonymize it and then publish it and no one would ever find out who it was but I was sharing the lessons I'd learned and I do think that the things that he was doing was daft but I think my embarrassment is around yeah maybe I should have spoken up more at work and told him maybe I I shouldn't have done it on the work laptop.
28:11There's a whole bunch of stuff that I probably haven't really unpacked over the years because I haven't talked about it. So feeling that you should have been just said directly to him what you thought that he was doing was wrong or? Probably should have stood up a bit more and spoken directly to him because I know if that was me, I would want someone to tell me, like, you're making mistakes. And I might not agree with them, but at least they've given me a chance to learn. I mean, that is one of the hardest things in the world is to speak truth to power. And I mean, we see that in the real world nowadays, certainly like there are people who should know better and yet they sit in meek silence and it doesn't make it better that it's hard.
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28:54But I think we have to all know that it's like one of these quirks in the human operating system that we're real bad at that. It's really hard. And not for nothing, but that's another benefit of FI is, like we say, F you money. It's not to literally go out in a blaze of glory screaming and cursing at people. It's to be able to stand up when you see something. I've used this in theory so many times. And I've said this in theory so many times. But this is a perfect example of it is you actually had an unscrupulous boss. You had someone who probably asked things of you that you didn't want to do.
29:32And it's pretty darn hard to stand up and speak truth to power when they're paying your paycheck. You need to pay whatever it is, the rent, the car bill, the mortgage, whatever. And your life's going to fall apart. I think this is why we pursue FI is to have FU money in this exact instance. So, I mean, Alan, I don't know exactly how old you were, but I don't know that you would have necessarily had some other option or recourse. I don't know that you could beat yourself up, but it's like, hey, would the Alan of today do that and sit meekly by? No, you would stand up. Exactly. Yes, I would stand up.
30:07100%. I would stand up. I would communicate. I would say, I don't think this is acceptable. But then that's from a position, if they fire me, I don't care. That's almost like you have the power, isn't it, to what Brad was saying, speaking truth to power. I was like, well, I have power now, so you are more free. What's the consequences now? They fire me. Oh, well, never mind. I'll do something else. Whereas I think I was 26, something like that. Which you've got the power financially. You've got the power in terms of you and your confidence. Confidence makes the biggest difference you could imagine.
30:44the confidence that comes from age from experience from having worked things out the confidence is unbelievably powerful and the ironic thing is that actually when you speak up to people they probably respect you more you actually get more power by doing that because well you can do it in a nice way it depends who it is for sure but i think you said the most important thing in there katie which is you are more free. And maybe, maybe, just maybe that is exactly what we're doing on the path to five is like every day we get a little more freedom. We get some more options. We get more power and you're a little more free.
31:25And hopefully the takeaway or people aren't listening to this and saying, oh, they're just talking about mistakes they made in their twenties. Like, and you just learned. I think what's beautiful is this can help a whole bunch of people not make mistakes. And it's not just about your twenties. I think these are human mistakes. These are very human mistakes. And yeah, I think having that power helps. And I think also not getting yourself into financial situations where you're dependent on somebody else. I think that's one of the many benefits of FI is we have financial space. And if you cannot build up a life that just, it's a house of cards, like you don't want a fragile life.
32:01You want an anti-fragile life. You want a life where if one bad thing happened, there isn't a cascade. It's not fragile. You want to be able to persevere through, hey, just the normal ups and downs of life, which happen, right? Sometimes you lose a job. Sometimes you want to leave a job. Sometimes there's a shock. Sometimes you need to spend more money in a given month or a given year than you would have anticipated. Sometimes life just throws you a curveball and that's normal. I think we're all kidding ourselves if it's just going to be like unicorns and rainbows all the time. The world doesn't work that way.
32:35It really doesn't. And just to be clear for everyone listening, this podcast idea was my idea. So we'd love to know if it worked or not. Tell us, did you enjoy sharing all the mistakes we made? Did you get value out of this? Tell us, if it didn't work for you, then it's my fault, not Brad's. I don't care. Blame it on me. That's fine. This is a great episode as far as I'm concerned. Katie, you're up next. when I was making my list of mistakes in preparation for chatting to you there was one that made me think about the path not traveled or the choice not taken and when I was a kid I was very focused on my studies I was very academic I was very school and getting good grades is the only important thing I wonder where that came from that might have come from my family we're not quite sure yet.
33:28But I was also sporty. And I was also musical. So I played the piano and clarinet and later the saxophone. And I played just about every sport under the sun that you could ever imagine. Every lunchtime at school, I was in some different sports club and after school. And there is a sport played in the UK called netball that most American listeners probably will never have heard of. But shout out to the Kiwis and the Aussies and the South Africans and the other countries where netball is played. It's basically basketball, but you can't run with the ball. I mean, I'm going to offend a bunch of people here.
34:07It's like a boring version of basketball where you are confined to certain areas of the court, depending on your position. You can't run with the ball. You can only be three feet away from your opponents when they have the ball. I think you told me it's take all the fun aspects of basketball away and you have netball that doesn't sound like something I'm saying so I'm back out of this now when I was a kid this is the sport I mean it's very like gender stereotype and I don't know if this has changed now but girls played netball boys played football now or soccer so I played football as well like outside of school and because I played in a really good football team I thought I was no good at football whereas in netball I felt like I was actually quite good because my method of knowing how good I am and my self-worth was comparing myself to everyone else in netball I came out on top in football I didn't for a good while netball actually preferred to football and I played at school and I played for like the grades above I knew that I was good and one time there was a guest coach at our school.
35:20She was amazing. She played netball for England and rugby for Wales. She was a powerhouse. She was amazing. And she said to me, Katie, promise me that you will continue to play netball. Like you really got some talent here. You could really go far. And I remember so clearly without missing a beat saying, no, I can't promise you that. I have to focus on my studies. I didn't even think, I didn't even go, oh, okay, that's an interesting idea, or how might that work that, you know, I think studies are important, but you know, there's an opportunity for both, like it's not binary, which is now one of my famous sayings, but at the time, I had not discovered that.
36:00It just got me thinking about different paths that you can take in your life. If I had thought, okay, let me pursue this netball idea. I mean, there's no money in netball, I wouldn't have made money, but I could have had, you know, an athletic career alongside working, you know, like that different path that I could have taken. So you look back and I was thinking, well, was that a mistake? Things have turned out pretty well. You know, I did focus on my studies, it did lead to me getting a well-paying job that meant that we could accelerate our path to fi I'm just really curious on both of your thoughts of you know it's obviously no you can't look back and have regrets but well you can well you can many it's very easy to look back and go I regret that help me make sense of this Brad and Alan yeah it's like the counterfactual thinking it's like what would have happened in that alternate scenario or I know we're all fans of movies like the sliding doors aspect of like, hey, what would have happened had I chosen that other path?
37:02And I think it's hard not to go down that. Because interestingly, you wound up actually being a professional footballer. I don't know, professional is the word, but you played for Chelsea, right? Yeah, it was before there was professional women's football. So I was never, I was a little bit too early. Okay, okay. But nevertheless, you played for Chelsea Football club which is not nothing yeah which if i jumped in there katie's being modest she played for chelsea she played at the top of the game she's an incredible footballer she's broken world records in football like she is phenomenal so she went on to have an incredible football career even though she didn't follow that route right i think the more interesting bit is the confidence and the comparison that to me because even if you had that career well there's no guarantee that that would have actually come to anything right like I could have been like okay great and then the main thing that has held me back in my sporting career has been my confidence and the comparison and you know I was a good player in my school if I'd have been thrown into netballers from other schools and the areas and then suddenly I'm like oh actually I'm not any good and would have crumbled confidence wise like it was quite an interesting thought experiment but that is another one of my mistakes that I jotted down was about my confidence and how I didn't have it as a as an athlete as a footballer as a I was about to say as a netballer but I did because I came out on top in my comparison in my head and how fragile that is because then I did that in my studies as well I was like oh I'm on top of my class I feel good about myself then I went to university suddenly I'm not top of the class because you know you go and it's a cliche but I went from being a big fish in a small pond to a small fish in a big sea I thought I could mix my metaphors there no that sounds about me and small fish in a big pond that has definitely been a recurring mistake that I'm still working on is comparison we have a famous phrase at rebel finance school don't compare your pineapples.
39:18I still do. And that's something I'm definitely working on. And it's a massive mistake, because there's no good that can come. There is always someone better than you. There is always someone worse than you. Yeah. And if your confidence comes from comparison, you're constantly looking outside yourself to see your value as a human. Whereas if your confidence comes from inside, well, then it can't be shaken and you just feel good about yourself. There's so much here. I just jotted down like five different things. So first, forgive me for the next four minutes of talking nonstop. You're my therapist, Brad.
39:53Okay. We humans are relative animals. We're not absolute animals. Everything is about comparison. So interestingly, Katie, right? Like you were great at netball amongst people who, and I know this from also conversations that we've had, not just from the last five minutes, but on a relative basis, you were head and shoulders above the people you played in netball. Whereas with football, so soccer, but we're going to call it football, you were playing with the best teams. So on a relative basis, you didn't feel like you were spectacular, even though on an absolute basis, you probably were one of the better or best players in England.
40:34And it's interesting because I saw this with my daughters and their swimming, which was they both went to swam year round when they were younger for one of the best swim clubs in America. They were never one of the top, even five or so girls in their age group at this swim club Nova. So on a relative basis, they were always looking at somebody better. But on an absolute basis, they both were at one point top 50 or 100 in the country in certain events. So like, again, they looked over their shoulder at the next lane and saw this girl who was always beating them. But on an absolute basis, they were pretty darn good.
41:17So that is tough to get over. I think we need to, again, it's just arming ourselves with knowledge, right? Like we have to understand sometimes you need to take a step back. This is like keeping up with the Joneses also, right? Like it's easy to look next door. Like Alan was saying, you need to be sufficient inside. It's easier said than done. Right. But another thing, Katie, also it's like fixed mindset versus growth mindset. Right. Like you definitely were stuck in the fixed mindset of I am X. Like as soon as this amazing netballer who played for England and rugby for Wales, I think you said.
41:49So, I mean, it absolutely incredible athlete said this to you. I mean, she was saying something from point of view of real knowledge and you just immediately dismissed it. I'm into my studies. Like that is what I am. I'm not, even though you were sporty, as you would say, like you cared about your studies. And like, I think that to me is the big takeaway is like, you didn't even open your aperture to say like, Oh, maybe I just got let in on a little secret here. Maybe I should think about this. It was just, okay, I am X. And like, anytime we have any kind of aspect of I am X, like I am smart, I am whatever, like you get locked in on that and you can't see out of it.
42:31And I think a lot of us, I mean, Katie, I'm going to use you as an example. And me also is like, I know one of your mistakes I think is similar to this in university. I know you went to one of the best universities in the world, Oxford at first. And I think it's easy to build your mindset around, I am smart. I fell prey to this too. I got accepted into Duke and Cornell and two of the top 15 schools in America. And I wound up going to the University of Richmond, which was a fantastic school. It's still an amazing school. But I had this mindset of, I am intelligent. And man, life smacks you upside the head real quick when you realize how deep the intelligence pool is.
43:13And if you ever build your worldview around, I'm the smartest person, I promise you, you're not, you're not even close and that's okay. Like it's just okay. Like you don't have to be, you don't have to be like, to me, it's what's your unique value. And this is where I think the imposter syndrome is something that a lot of us fall prey to. And I've actually really come to peace with that imposter syndrome, which is like, who the heck am I to talk to literally millions of people on this podcast that's been around for nine years? Like, why do all these people look to me? And I'm not a world-class expert on personal finance or, you know, I have all these negative limits or I had all these limiting beliefs.
43:53And I think I've really come around to, I have a unique value add in terms of I can simplify and synthesize information better than just about anybody in the world of personal finance, literally in the world. And I don't say that lightly. I have a very hard time, as you both know, talking nicely about myself. So when I say that out loud, I just know this is like a long time coming. Like that is what I do. I simplify things. I make it easy and I embolden people to take action. And that is a unique value add. And you don't need to be the most knowledgeable person in the world. And I think that to me is one of the big takeaways.
44:30So again, Katie, like that's a whole lot of like random little lessons that I gleaned from just your one mistake. But this is what we're doing here, right? We're trying to like, just really talk through this and how do other people move forward from that. So that's my little, I don't know if we'll go therapy session, but any thoughts? One overriding thought I had as you were talking was like, Oh, I've completely hijacked this and got Brad to like help me with my demons. But there is definitely like the fixed and the growth mindset, something that I'm still working on because whilst talking to all the people listening about my mistakes I really hate making mistakes and part of the reason I hate it is because I beat myself up when I do it and this is small mistakes medium-sized mistakes I just get really embarrassed and then find it really hard to learn from it because I'll go into like cover-up mode and not wanting anyone to know that I made a mistake and perfectionism and all the fun stuff.
45:32So it's actually quite cathartic talking about this stuff. I think I learned many years ago that your success in life is directly related to how many mistakes you can make as quickly as possible and learn from them. It's not making the mistake and stopping, it's making the mistake and learning from them. And if you do that at speed through your 20s and 30s and 40s, make a ton of mistakes and learn, the speed and growth you will go through is phenomenal. Now, one better than that is if you don't make the mistakes yourself, you learn from other people's mistakes, which was the whole point of the episode, because then you save all that time, all that energy, all that money.
46:11That's one better than that. But if you can just make the mistakes, apologize, say you were trying your best, learn and keep moving, your success is virtually guaranteed. Totally agreed. And I think that's in every aspect of life. I know I've seen it in the small businesses that I've created and failed over and over and over and over and over again for almost a decade. But just small failures. But I learned every single time. I don't look at those as failures. Those were the building blocks to help me create something successful. And I just very simply would not have been ready had I not made those mistakes.
46:48So, I mean, it's almost cliche. It's like the Thomas Edison. I tried a thousand times and I learned something every time. but like it's cliche for a reason because that's actually how life works if you think you're going to get it right the first time that's not it it really isn't i love that alan it's like make as many as you can as quickly as you can because and i think katie and i both might have been embarrassed about our mistakes and such but like i know i picked up and i moved on i kept going and i don't know where that internal fortitude came from frankly but like man am i happy that that brad that version of brad just kept moving forward kind of don't have an option either you just well you either pick yourself up and get on with it or you give up yeah that's the option it is but that's not a very good option obviously looking at your stare it's not exciting the allen stare doesn't come across on podcast it really doesn't work on podcast tell us one of your mistakes i think there's minor ones along the way like i remember there was someone who wanted to talk to me and i dodged what they were doing told them that i was out and couldn't talk.
47:55And then they turned up at my house to drop something off and saw me in the window. And it was the most embarrassing thing ever because I'd lied to them. And it was a white lie to protect my time. But the embarrassment and the pain, it damaged the friendship. And then the other person thinks, well, how can I trust that person when they lied to me with that stuff? And I obviously can still feel it to this day. If you're listening to this, Paul, I apologize. I was young and I didn't know how to say the honest stuff but now I think the biggest lesson I've had of that is if you don't want to go you have to say I don't want to go and you just have to own it you just have to be straightforward you have to do it and it's the best thing you can do is the honesty of saying I really don't fancy it tonight thank you for the offer I'm not coming and it's actually really as bad as you think right he'd have probably gone okay yeah he would have accepted it like what an idiot why did I make up a lie it's just that trying to avoid conflict that just comes back to bite you in lovely wonderful different ways and create more conflict it's tough though isn't it that's a hard lesson to learn to just be direct because it's scary like how are they going to react what they're going to say even yesterday I spent an hour composing a text message to someone of something that I wanted to talk to them about.
49:22And Alan's like, why are you not just ringing them? I was like, oh. And then I felt really embarrassed like I'd spent an hour wasting my time. I messaged like, are you around to chat? And he said yes. And then my heart was thumping. I was like, it was scary. And then I chatted to him and he was really nice about it. And we resolved what it was that I wanted to talk about. And I was like, oh, why did I torture myself for an hour beautifully crafting this message when the right call all along was just ring them talk them actually that was an opportunity to feel courageous and actually the thing that I got from it was I was scared I did mess around a little bit and avoid doing it but then I did do it and I was scared but I did it so there's always a chance to redeem yourself as I was saying that I was like that's not actually true but I took that one and another one along the lines of just being honest.
50:18I think when someone asks you to do something that sometimes the easy answer instead of no is maybe it's just about like people usually almost always. And I know I had a conversation with my daughters about this recently, because I think one of them, I don't think it was about me. I think they were saying about some other adults in their life was like, Oh, anytime you say maybe it really means no. And it's like, why can't you just be direct and say no? Because you don't want to hurt somebody's feelings because whatever, there's always that easy answer, but you have to become okay with that because oftentimes the answer just simply is no.
50:51And it's also about your own boundaries and honoring your time and your energy. And like, that's important too. You don't owe anything to anybody. I think that's another thing. A lot of us people pleasers fall prey to is, Oh, I owe it to them. You don't owe anybody anything. You owe the world basically like to show up the way that you want to show up. And I don't think you owe anything to any particular person. And if it means you need to not say yes to that plan 99 times out of a hundred, you got to do you. And actually it reminds me of a book, a member of our community, a really wonderful woman named Elizabeth Andrews wrote a book.
51:28It's a really short book, but it's a really impactful. It's called 50 ways to say no, go to phrases to honor your boundaries and why they work. And you could probably read this book in under an hour, but it's fantastic. It's like 50 of these phrases and situational things of just how to kindly, but forcefully say no. And I know I needed it. I flipped through it. I love the book. It's almost like having an investor policy statement for when things go terrible. It's like in good times when you're not faced right there with that moment of Katie, the heart pounding and whatever, like, Oh my God, what am I going to do?
52:05Like you have to have a couple of phrases that work for you set in your mind, it just makes it easier. I would highly recommend that book. The classic version of that is always try. When you say, oh, let's go out to friends and they say, oh, I'll try and make it. You know they're not coming. Try is just a polite way of saying no. And we have to actually get used to saying no. But also on the other side, if you see someone say, I'll try, that actually is a code word or a point for you to say, sounds like it doesn't work. Would it be better to do it another time? And you can actually hear that and do something about it yourself.
52:47So I don't think the responsibility is 100 % on the person saying it. I think we can live with that and say, oh, maybe. You said maybe. Sounds like maybe it doesn't work. Is there something I can do to help you? Would it work better at a different time? You can hear those trigger words and do something about it. And then you can actually uncover what the reason is rather than just guessing like, oh, they don't want to hang out with me and making it about yourself or making up a bunch of stories about what the reason is. Yeah, you can even make it easy for them. Like, I know things are busy or I know this is happening.
53:22Like, just tell me and I'm happy with it because I've got plenty to do or I can do this. So you can make it easy for them to say no. And I think sometimes it is a benefit to make it easy for the other person to say no. I like it. All right, let's keep going down. So I've got another speculation one. This is mortifying. And I've never said this out loud before to literally anybody. I invested in that horrible Cathie Wood arc investing mutual fund. It wasn't a lot of money, but it was not insignificant. I forget exactly what it was, 10 or$20 ,000, maybe even a little more, but it was everything I counsel against.
53:58And this was in the truths of our years. So let's be clear, Like anybody can fall prey to this stuff. And not like I'm some infallible person by any means, but it's easy to get wrapped up in things, to get wrapped up in narratives and stories and genius and blah, blah, blah. And I know better and I still got wrapped up in it. So luckily this was not a catastrophic mistake. But yeah, hopefully that's a lesson of like, okay, look, we can get caught up in speculation. We just can. And we just have to know better. It's happened to me now multiple times. I've said it just in the last hour with the investing in North Carolina and this, it's just, it really is easy.
54:33So there's no secret. There's virtually no genius. I mean, there's maybe Warren Buffett and Charlie Munger and maybe a few other people over the last hundred years, but you're not going to just happen upon them. And frankly, if you've already found out that the person is wildly successful, like quote unquote, you're probably a little bit too late. So don't get caught up in wild speculative behavior is my takeaway. It's definitely that thing of as soon as everyone's talking about it, it's too late. So if you hear it from everyone, recently until the drop, it was gold. Everywhere, everyone was talking about gold.
55:07And I just knew as soon as that happened, it's like you hear it from the people that you're just next door. You hear it from people all over the place and they're like, oh, you should invest in gold. It's doing really well. As soon as you hear that, just do the opposite. Just walk away. Sell all your gold. to do it. You shouldn't have any gold anyway, but that's a whole different discussion. But it's the excitement and the fervor of the general population should be a sign that you shouldn't get involved, not that you should do it. Yeah, agreed. All right, Alan, what's up next on your list? Bear your soul.
55:44Bear my soul. Thinking about which ones are most valuable for you who are listening. I think I created a fairly successful business. One of the mistakes I made was never building an email list. And I did years of work. I never captured people's email addresses. I never had a way to go back to the marketing. I'd never started a newsletter. I never did any of that stuff. And I regret not building a mailing list from the very start of my business. and I'd love everyone to avoid that if you're launching a business if you're building a business build a list it's the most valuable thing you can build I think actually even more so nowadays when people have their followers on YouTube or their whatever the other thing is Instagram TikTok I mean even something as old school as our Facebook group but keep going Katie I want to I want to talk about that in a minute.
56:43Well, yeah, just that you're so fragile, aren't you? You talked about fragility earlier, Brad. You're so fragile to that platform saying, no. And then you've got no way of contacting all those people that want to hear from you. So especially nowadays, if your whole thing is on social media to get the email addresses outside of that. Yeah, I would agree. I think to me, the lesson is control your business and don't outsource it to some other platform because you never know what that platform is going to be. I mean, frankly, a lot of people who built their livelihood around Twitter and then it got bought by Elon Musk, you know, who ran it into a cesspool.
57:25I mean, I know people who had hundreds of thousands of followers there. They spent years and years and years, and now they're part of a cesspool. You never know. Sadly, we're seeing a lot of these social media platforms just become run by malevolent actors. And Facebook is where we built all of our local groups. We have a choose a Facebook group with 120 ,000 plus people. And we have no control over that. And that was just a strategic mistake. If I put a post in quote unquote, my Facebook group, I'm lucky if 1 % of people see it because it's an algorithm. That's not a partner. That's an antagonistic relationship, right?
58:03Like that's, that's crazy. So like, why would I ever want to enrich Mark Zuckerberg of all people? Again, I want to stay away from malevolent actors. I don't want to enrich them. You have to build your own platform. Sadly, even today, 2026 email is the one reliable way to get in touch with people. So Alan, I totally agree. Even in this age, you have to have a way to directly contact your customers. There are plenty of people who sell on Amazon. It's the same thing. It's like, you're just looking for all these malevolent actors. Like they do everything they can, Amazon, to raise fees constantly, to make it impossible for you to contact your customers, quote unquote, because they're not your customers, they're Amazon's customers, right?
58:43Like, let's be clear, you've built a business on the most fragile of fragile sands. It's ridiculous, but yet this is what people do. So power, right? And it goes back to that. It's like, try to get as much on your side of the court as you possibly can. Yes. And to highlight, I didn't even build on one of these platforms. I just didn't even build a list. So that's how bad my mistake was. I didn't even make that mistake. So I wanted to share that one because I think it will help people. And if I could build a second one on that, I was so scared of sales, cold calling, putting myself out there, rejection that I did not put myself out there to scale.
59:23I did not go all out when I started my business. I let fear, embarrassment, and being a scaredy cat stop me from putting myself out there. And coming back to the conversation you had with Katie about comparison and different things, if I could give everyone a sentence, the sentence I would give you is spend as much time building your confidence as you do your net worth because it is so powerful in everything you do going forwards. So just spend time building your confidence and your happiness and it will create magic in your life. And yeah, I think with confidence, I actually had one which is not negotiating my salary.
1:00:09And I think a lot of us, a lot of us do this. We just think we should accept whatever it is. Because again, it's like we're getting some gift of this job. And even if you're in a position of power, if you don't know it, then you're not. And if you're not confident in yourself, then you're not. So I know when I left the big public accounting firm and went to work for one of my clients, I did wind up getting a raise from my public accounting salary. But I knew that really in my particular case, when you work for a big public accounting firm, if you stay and become a senior manager or certainly a partner, the carrot of doing that is a massive salary.
1:00:52Now at my client, I was moving for essentially a lifestyle play and I knew the top salary was capped. And the only time I would get a big bump was when I moved because then otherwise I would just be getting the normal two, three, 4 % raises. And I did get a bump, but I knew in my heart of hearts, I should have asked for more. And I didn't, I was just too scared and I didn't have the words for it. And I think that's another thing I've picked up just from doing this podcast for nine years. We had two incredible women on the show. Tori Dunlap was on episode 147 and financial mechanic who was on a couple of times, most recently in episode 454.
1:01:34And they gave like very specific scripts for salary negotiation and making it a win-win. And had I listened to both of them before that, I would have done better. I didn't know better and I was scared. And I think practicing, having these skills, having this knowledge and knowing that I should be doing this, I think I would have made a better decision. So yeah, that's a lot of lessons all wrapped up in a one, but that was a pretty good one. It is a fantastic one. I think what we're all saying is work on your confidence because it will have a force multiplier effect in every area of your life, whether that is playing the sport you play, asking for a raise, turning up at work happier.
1:02:21one of the interesting things I learned a long time ago was they did an incredible study about why people choose suppliers. And you would think people choose suppliers because of the quality of the product, because of the price of the product, all of those different things. Is it quality? Is it price? Is it the thing? Is it timing? What do you think the number one reason was people chose a specific supplier of a product. I don't know, probably they liked the person they were dealing with or something? Yeah, the person they were dealing with was more fun. The word that came up specifically was fun.
1:02:57It's like, I like working with this human. They are fun to be around. And I just couldn't believe it when I heard that, but I've experienced it. People like to have calls with us because we're uplifting, because we're inspiring. They enjoy being around us. and if you could just have more fun if you were just happier in life people would gravitate towards you more and it is amazing how you almost can't imagine this like the universe said if you're happier and have more fun you'll be wealthier and more successful it's like where's the downside yeah really do i really have to do this like no you can stay grumpy if you want to you're welcome to be grumpy all you want to but you're not going to attract all the fun and happiness around you.
1:03:42And when I saw that study, it just shocked me. Why am I competing on price? Why am I competing on quality? Yes, I have to have a good price. Yes, I have to have good quality. But if those things are equal, they're going to choose the person that's more fun to be around. I was just imagining a universe where everyone in a particular industry had read that report, and then they're all trying to out-fun each other. Out-competing on fun. Showing up in a clown suit and like a, I don't know, trying to fit as many people as they can in a mini. It's not happened in accounting yet. Probably not going to.
1:04:24I had this theory that one of the most valuable gifts we could give to you was by sharing our mistakes so that you don't have to make the same mistakes that we've made over the years. That was my theory. but I want to know I genuinely want to know did you enjoy the episode did you get value out of it what did you think do you have mistakes that you're like I want to tell the whole world about my mistakes now so I can save everyone else pain yeah tell us yeah I love that and this is super fun it's great when we uh just randomly brainstorm an idea and bring it to fruition right what's fun now is in our community platform, we now have the ability to comment on these podcasts.
1:05:08You can always get there by just going to chooseify.com slash and then the episode number. Actually, when we're recording this, I'm getting ready to go to Japan for a couple of weeks. So I'm not 100 % sure which episode number this is, but it'll be something like 594, 595, et cetera. Chooseify.com slash 594, for instance. And it'll take you right there. If you're not a member of the platform, sign up. It takes 30 seconds. You can actually join your local group. So you'll get email notifications of all the local group events, which is again, going back to the getting away from Facebook and malevolent actors.
1:05:41You're not subject to their ridiculous algorithm. You now just get the email and it just shows up and it's really simple and you don't have to do anything else. Even if you just want to sign up 30 seconds for your local group, do it, but otherwise go to that and then leave a comment. Also leave your biggest mistake or a couple of them. And we can do a follow-up episode to this. I know we all have a bunch more, I suspect, and we could probably brainstorm for hours again. That's the fun part of making this the ultimate crowdsource personal finance show. This is a living document. Now we have the ability to really discuss it.
1:06:14I know the two of you will be in there. I'll be in there. We'll be commenting on everyone's comments. That'll be a lot of fun. It'll be a lot of fun. And I'm really excited that we can share this with everyone because it is the most valuable gift you can give helping someone to learn from your mistakes wholeheartedly agree all right friends where can people find you i know there's multiple places but where would you like to send people uh if you want to read about our content and what we do then it's rebel donegan's.com and you can see all about rebel finance school the blog and all the different things we're doing on the blog that's kind of where we share most of what we do.
1:06:50We do have a mailing list as well because I learned my lesson and you have to build a list because you actually want to be able to communicate with people. Here's what we're doing and here's what the plans are. And we're gearing up to run Rebel Finance School 2026. So get yourself on the mailing list and you'll be first to know when we launch sign up for that. And if you're good with your finances, then tell your kids about it. Because if we can save them whilst they're young, we will create an incredible impact. Totally agreed. And also you can get on the email list for our extraordinary events, which is great.
1:07:22We are probably 99 % going to have one February of 2027. Again, here in Richmond. Yeah, if you get on that email list, you'll be the first to know when tickets go and sale. Yeah, we will be back to Richmond. We absolutely loved hanging out with you. It was fantastic. Indeed, indeed. All right, everybody. Well, hope you had fun hanging out with the three of us today and really lean into this. We really can all learn from others' mistakes. We can learn from our own mistakes and it's never catastrophic. I mean, take it from me. I've obviously passed along some catastrophic ones and I'm doing great.
1:07:56So that's the fun part about life. That's the fun part about the Paptify is we can pick ourselves up, we can learn from our mistakes and we can move on and we can live wonderful lives. Thanks for being part of the community and thanks for listening to the podcast.
1:08:11Thank you.
From the publisher
Even financially independent people have lost fortunes to bad investments, high-fee funds, and speculation. Brad Barrett, Alan Donegan, and Katie Donegan lay bare their most expensive mistakes—from Alan's 90% dot-com crash loss to Katie's near-£1 million fee trap to Brad's decade-long real estate nightmare—proving that catastrophic errors don't prevent you from reaching FI if you learn the right lessons. Key Topics Discussed [00:00:00] Introduction: Why Share Mistakes? Brad introduces the episode concept, explaining why sharing financial and life mistakes can help others avoid similar pitfalls on their FI journey. [00:03:30] Alan's Dot-Com Bubble Disaster Alan shares how he lost 90% of his £7,000 life savings investing in high-tech managed growth stocks right before the dot-com crash, and how this scared him away from stock market investing for 13 years. [00:08:45] Brad's Early Investment Mistakes Brad discusses investing in WorldCom and other 'top picks' that went bankrupt, plus getting sold a mutual fund with horrible loads, highlighting that there's no secret investment knowledge reserved for the wealthy. [00:13:20] Katie's High-Fee Fund Trap Katie reveals how a financial advisor convinced her to invest in actively managed funds with 2.71% ongoing fees plus 3% entry charges, a mistake that would have cost her and Alan £1 million if they hadn't discovered index investing. [00:18:50] Brad's Real Estate Speculation Nightmare Brad shares his biggest mistake: speculating on golf course community properties with interest-only loans right before the 2008 crash, causing over a decade of stress and significant financial loss. [00:28:15] Alan's Career Mistakes: The Book Incident Alan reveals how he wrote a book called 'How Not to Run a Business' about his boss on the company laptop, got fired, and learned about speaking truth to power and the importance of FI for workplace freedom. [00:32:40] Katie's Confidence and Comparison Struggles Katie discusses how her fixed mindset and comparison with others held her back from pursuing opportunities like netball and football, and how building confidence is as important as building net worth. [00:42:30] The Power of Saying No and Setting Boundaries The trio discusses the difficulty of being direct and honest, the importance of saying no, and how people-pleasing can create more problems than it solves. [00:48:20] Business Mistakes: Email Lists and Sales Fear Alan shares his regret about never building an email list for his successful business and letting fear of rejection prevent him from scaling, emphasizing the importance of owning your platform. [00:54:10] Salary Negotiation and Final Thoughts Brad discusses not negotiating his salary when changing jobs, the hosts wrap up with reflections on learning from mistakes, and encourage listeners to share their own mistakes in the community. Notable Quotes Brad Barrett: "You can make mistakes and you can make catastrophic mistakes, and you can pick yourself back up and you can move on with your life. You're stronger and you're wiser." Alan Donegan: "Your success in life is directly related to how many mistakes you can make as quickly as possible and learn from them." Alan Donegan: "Spend as much time building your confidence as you do your net worth, because it is so powerful in everything you do going forwards." Katie Donegan: "To rinse the value out of the mistakes, it's a lot more valuable if we share them. I would love you to get the value out of my mistake because I've already paid the price." Brad Barrett: "There's no secret. There's virtually no genius. Don't get caught up in wild speculative behavior." Key Takeaways Invest in low-cost index funds like VTI instead of actively managed funds or individual stocks to avoid high fees and poor performance Build an email list from day one if you're starting a business—don't rely solely on social media platforms you don't control Always negotiate your salary when changing jobs or getting promoted Wor…
