We Lost Millions in Crypto (Here’s What It Taught Us)
16 Dec 2025 · 26 min
Podcast episode (Wealth Shift by Ben and Berg) in which Ben Simpson and Aaron Berghober recount multi-year personal losses and missed gains in crypto to teach practical investing lessons. They describe mistakes from 2017 ICO chasing (~$20–30k invested across ICOs that were later written off), trading-follow mistakes that cost about 0.6 BTC, selling a conviction position in Synthetix (formerly Haven) before it later rallied, missing bitcoin buys in 2020–2022, and emotional round-trip sales of a Moonbirds NFT (entered at ~USD 6k–10k, brief peak to ~USD150k). Core lessons: adopt a simple, documented investment plan (buy/sell rules), avoid influencer-driven fear/trading, don’t overtrade against institutional algo/quant edges, prepare legal/tax structures early (mentions Australian marginal tax context), and pause when feeling rushed to avoid scams. Episode ends with CTA to Collective Shift’s seven-step training.
Questions this episode answers
December 16, 2025
Ben Simpson and Aaron Berghober
2017, 2018–2019, 2021, 2022
About US$20,000–US$30,000
Approximately 0.6 BTC (described as today’s-equivalent ~US$60,000+)
Chapters
Welcome back to the Wealth Shift by Ben and Berg. The Go to playbook for busy investors building real wealth in the digital era. I'm Ben Simpson, high school dropout turned eight figure entrepreneur, investor and founder of Collective Shift, a global crypto research platform. With clients around the world. And Aaron Berghober, an mba, qualified financially free investor and business leader. The show dives deep into strategy, shaping the next generation of wealth builders. Together, we unpack the exact frameworks used by sophisticated investors to grow and protect wealth across crypto, business property and macro markets, which with no fluff, hype or jargon, Whether you're managing $100,000 portfolio or 5 million plus, the wealth shift delivers timeless strategies, investor psychology and actual insights for those serious about playing the long game. This is your playbook for building wealth in the digital era. Every single week we release new episodes breaking down exactly what's going on. Make sure you hit subscribe to get the episodes as they come out. If you're on the podcasting app or if you're on YouTube. And today we're talking about the, the millions of dollars we've lost in crypto, what it taught us, and how you can take these lessons and experiences and implement on your own. Because crypto is volatile. We're going through a volatile period right now. Bull markets always like this. Fear is high, greed is high at the pendulum swings, and you tend to make the worst mistakes on the way down. All right, when the market's volatile, you know, we've seen a number of corrections this year already in crypto. Back in April, you know, altcoins were down 65, 70%, Solana, Wicked, $90. Bitcoin was at $75,000. We saw huge corrections across the board. We saw the biggest liquidation in 24 hour history for crypto a few weeks ago in October, more than three or four times the FTX liquidation. Crazy amounts of volatility. And Bergs and I have been investing in crypto for a long time now, 2017 for both of us and man, we've made some bad decisions. And mad.
Oh, isn't it, isn't it just wild where when the number's going up, you're like, I'm investing. This is what I expect it to do. But the second it starts retracing and you look at that little number and your wealth is going down. And bro, the classic 30% drawdown in a bull market just, oh, straight in the heart, bro. Like the emotions just start flaring up. You're like, I'm losing money. This isn't the way it's supposed to go, it's. It's up only, like, I put my money into this thing. This is crazy. And this is where we have made our worst mistakes. Mate. I'm going to kick us off and let's start right at the beginning. 2017. Biggest mistake was thinking I was very smart. Chasing the current trend of the time and investing shed loads of money into ICOs. And at the time, it probably wasn't shed loads of money. It might have been all together over that ICO period. 20 grand, 30 grand, something like that. Right. But every time I would enter an ICO, I would buy new ETH at $80, some of it was $50. And I would buy that ICO and it will go up maybe 10x. And of course I wouldn't sell because everything's going to the moon. Why not wait for the 100x that everyone else has? And all of them went to zero and I had to write them all off. And yes, it was only 20 to 30k, but if I would have just listened to myself, back myself and kept that eighth, that's probably like a $3 million mistake.
Yeah, man. The chasing, the. Chasing the hot thing on the, on the block, ICOs, NFTs, metaverse, whatever. It is like looking back at what you would have had if you just held. And this is a lot of people, they trade and try and do different things to get more returns faster. You look back and you go, wow, what would I have done if I've just held and not panicked and not done these crazy things? I was the same. So much money just barreling to ICOs and what ICO is around to date, I don't know.
That's exactly it. It's like the 1 or 2% that is still around. And you had this as well, mate. You had a very, very big trade on. Not a big trade. You. You bought something and then you got rid of it because it was doing nothing, mate.
Yeah, Synthetics. This was. It was called Haven before renamed to Synthetics. So Synthetix was a, you know, huge altcoin that had a massive run in the 2021 altcoin season. I got into this around 2018, 2019, from memory, it was called Haven. Held onto it for a long time, had conviction, but it didn't do anything. And. And I wasn't paying attention, I wasn't focused. I had too many old coins and I sold it. And I was sold all of it, a hundred percent of it. And I remember looking back a few months later, after I Realized that it renamed to synthetics, it had new token economics, it had a huge launch and this thing did tens 20, 30x returns.
I think it was a lot more than that. I think previous pod, I think it was like close to a 9 million dollar mistake. It was like it was a ridiculous amount of money. And the lesson here is exactly the same where you've looked at a company, I'm pretty sure that the interviews with that company, talking to those people, you knew it was legit. But then getting that kind of, you know, it lost a bit of momentum and there's other shiny things and trying to chase those instead of staying with the project that you've researched and you know well about. Even though the price isn't reflecting how good you know it is. Just having that conviction and sticking to your plan.
Yes. And that's, that's probably the biggest takeaway for you guys listening at home is having a plan and sticking to it. When we're in periods of, you know, uncertainty and you, you know, you're worried and you're concerned and maybe altcoins aren't doing as what you would have hoped. Having the strategy and having patience and remaining in the market without throwing the towel in is, is important, you know, conviction on assets but without a structure or a plan is just chaos and it's going to lead to poor decisions. You need to learn to wait, have the confirmation and understand what your altcoins are doing. This is another lesson as well, is like if you have so many different altcoins and you have no idea what any of them are doing at any period of time, well then you have no ability to make a good decision because you have no idea what the altcoins are doing. And this is about having a simple strategy, not trading out too early and not being impatient and being able to weather the storm. Super important.
Absolutely man. Let's, let's continue with 2017 mate. So what a time mine was. Oh man, it's so brutal to admit these. Hey, it's just like oh geez. So this was in 2017 and I had a trade on thinking I'm a very smart trader. I made one or two trades, made a little bit of money. Like there was a flash crash. I remember with Iota, went down to 50 cents and within a couple of minutes went back up to like a $50, made like 8k US. I'm like oh I'm the best, let's go. So I had a trade on and I was following a trader and this was a BTC ETH paired trade.
Yep.
And I had 0.6 Bitcoin on the trade. Right. Imagine how much that is worth like 60k USD plus at the time it was like maybe worth $3,000. And I've got this trade on and they're like no, no, no, just keep adding to the trade. Like a few days goes by, a week goes by and they're like no, no, no, like it's coming close but you know this pressure will happen. So I added more, added more up to 0.6 BTC and I ended up going on a holiday with my mates because I had a trip to Japan booked. So of course here I am sitting in this hotel room stressing out about this fucking trade while I should be enjoying myself, adding more money into it, setting my like time zone. My phone is not working for my little two factor authentication to get into the exchange and all this sort of crap. And at the end of the day I just cut the trade and went it like, you know, it's not worth my time in Japan but that cost me 0.6 BTC. And, and if you zoom out from now, like in five years time, even from now, most people in the world won't be able to afford 0.6 BTC. But by following that trader, believing the bullshit, thinking I was a trader, I've now lost in today's terms US$60,000 plus just from that one thing. And that's the only trade I can remember. What about all the other bloody trades?
I can't remember. And also as a trader as well, like, or trying to become a trader. How many clients do we speak to that join us going, oh shit. I tried trading, man, that, that's just.
Like they tell you. Yeah, they tell you it's so easy. You sit in front of a screen for seven minutes a day is. I was constantly looking at that. I remember I had another trade on and it was actually the anniversary with my wife and we were out and we went to the place we got married at and then we're going to a hotel and my phone literally bricked while I was there and I had like, I don't know, a significant trade on and I was like, oh. And for the next probably four or five hours it just ruined like our anniversary. And to the end where I was just like it, whatever happens, happens. I was lucky I could get into that mindset. But just doing those things and trying to live a normal life and be a trader, they don't go together. You need to turn your emotions off, you need to be in front of the screen, you need to be very active. You cannot do in seven minutes a day.
Just think about that at home, listeners. Do you think that these core sellers of trading can literally make you money? When you spend 10 minutes a day that they sell sitting by the pool, you are coming up against quant funds, AI algorithms, huge institutional platforms, and you think you can sit by the pool drinking a cocktail to beat them? No fucking chance. Absolutely not. Does exist.
And, and this thing that we're talking about with trading ICOs, oh, even NFTs. I didn't cut my losses. I probably lost 30k in NFTs. I was in discords. We're all going to make it. That was just. This whole thing is a distraction.
Yeah, right.
Getting distracted is the main point here. Thinking you can move faster, you can make more money, you're smarter than the other people on the other side of the screen.
Yeah.
You're not unless you've dedicated years of your life to it and you've got some serious competitive advantage.
Yeah. What is your edge?
Yeah.
And, and I think to that point, you know, my, another big mistake that I made early on in my, you know, journey back in 2018, 2019 is that I, you know, was following a guy on YouTube that seemingly knew what he was doing. He put out a lot of TA content. He had this sort of like proprietary algorithm that he created. And you know, I bought into that and, you know, thought that he knew exactly what he was doing. And you know, I outsourced my decision making to him solely and I had no idea, you know, of how wrong he was going to be. And you know, he, he had this prediction that bitcoin was going down 60, 70%. The, the theory that he had. And I sold out a huge chunk of my bitcoin at like $20,000 because I was scared it was going to go down. And you know, long story short, didn't go anywhere near where he said and bitcoin ripped. And I was sidelined there for a little while and that was a big learning lesson for me is like, you know, getting into these fear mongering, like based, you know, content, you know, loopholes where you just end up like spiraling and listening to people and you get scared and worried and you sell out is the absolute worst thing to do. And that is kind of what we see every single bull run. And all you guys listening at home probably know this. When your portfolio goes down, you see this corrections, you get fearful, you get panicked. You know, usually at the time where you want to Sell and, you know, reduce your risk is usually when it's peak, fear, when it's peak, you know, bloodbath. In terms of the market, that is usually the time that everyone capitulates and a bottom's formed. So remember that when you're feeling something and everyone else is feeling the same thing, it's usually close to a pivot point. And you know, for me that was a huge mistake that I made early on. And also just listening to influencers on YouTube that are like, you know, realizing that their incentives are not in line with you, they just want to get your views.
You raise a great point about youtubers and influencers where investing is deeply personal, your goals are personal, the way you like to live your life, how much time you want to spend with it, your time horizons, how much money you have already, all of those need to be factored in. But these YouTubers, they specialize in hooking you in and, and selling you something or using their trading link or they get paid some way and the equivalent of this is like a YouTuber going, oh, I'll get you a house. And that's like, well, great, but you don't know me. Where's the house going to be? Is going to be a tiny house? Is it a mansion? You don't know if I've got a family. You don't know my requirements, you don't know all this stuff. Do I need one next month? Do I need one in five years time? Do I need one in five months? What are all of these things that go into, into your makeup and then that informs the type of investor you are and how you like to actually run things? It's just, I've got 100k, what do I put it in? It's like, well, what are your goals? Like, you know, what do you want to achieve? What's your time horizon? What's your risk tolerance? How often do you want to be in front of the screen? How often do you want to monitor these things? And I got sucked into the exact same thing where I think investing is all the same. These guys have made money, they know what they're doing. Ben, you've been over to the States recently. You've seen how the source is made with these people, how they hire all the Lamborghinis, everything else to try and convince you that they know what they're doing and they are going to make you money. And this is the well known trodden path.
Yeah, it is. People sell the dream and the lifestyle, not the information and the knowledge. You Know, you guys don't listen to us because we're good looking. You listen to us because we're, you know, we're good at what we do and we have the information and knowledge. And yes, I may not get the views or the downloads, but that's the, that's the insight, right? That's the quality of the content or the quality of the insights versus someone that's primarily focused on buying Lamborghinis. And you know, Richard Mille watches to sell you that dream. It's usually the wrong way around.
And this is what got in my head in 2017 and 2022. So 2020, I didn't buy enough bitcoin. Fair enough. First cycle, got distracted by ICOs. 2022, I should have known better at the end of the year. I was actually working for Collective Shift at this point. Spent hundreds of hours understanding bitcoin and I'm pretty sure Bitcoin dropped below 30k on one day. I think it dropped 5 or 6k. You and I were meeting up for breakfast, we're like, oh, mate, it's dropped. I got to buy some. Never bought it, got distracted, thought about other crap. Oh, don't worry, I've got these other investments. Listen to YouTubers still. And if I would have just bought some bitcoin, I would have more than tripled my money already within three years. The simplest thing, just click, buy, go to sleep, wake up three years later, I've tripled my money and just getting distracted by the noise and not listening to myself. With the hundreds of hours of research I've done, being able to explain it to other people and having that conviction to just press, buy and go to sleep. Hugest mistake. That alone would have cost me upwards of 500k, I reckon.
Yeah, yeah. Because you overthink it and it becomes complex. And I had a similar position when I my first bull market. I had all these old coins, I had all this stuff going on, I had complex strategies, I had to do all these things and I made a lot of money on paper, but then round trip, the entire thing because I had had too much going on.
This is it. So people think that the more you put in with investing, the better investor you're going to be. Actually, the opposite is true. It's knowing your preferences and sticking to a plan, adopting that plan and executing against it.
Yeah.
That is what will bring you success. And I think back to similes like cyber security. It's not like you learning everything about cyber security. Adopt a framework and you go and implement that framework, you come in with, where you're at, what you want, how you want to run things, and you pick up a framework, you make a plan and you go and execute against that. That is the way you don't spend every single day on YouTube, what happened this week, or interest rates, this, that, whatever. Yeah, fair enough. There's a couple of inputs you need to know about, but not every day because that's just going to influence your information diet. The way that you think people are going to get in your head, other people speaking in your head instead of what you know inside the plan that you've made and executing against that.
Yeah, yeah. And, and that's the, the, what we saw on our client side. The, the clients that we work with. Primarily, the best results always come from people that aren't spending time in crypto. 50 to 70 year old women in our group probably outperform most people because they have a simple strategy, they're not driven by ego and they don't really know a lot about crypto and they're making a lot of money because they have a very simple strategy. And that's ultimately where we can all take lessons from that and what we work with, you know, and what I see on the, on the client side is simple wins.
Yeah, yeah. And it's, it's amazing. Like you see people come in and they're very like fired up. We work with them, we kind of help them out and it takes a while for their psychology to kind of catch up. And you see that like kind of months later and they're like, tried all this stuff, had a plan, didn't work, adopted the plan, and now I've just got these gains and it's like when people are like new to the group and they're still, you know, somewhat losing their minds because, you know, they, you know, they, it takes a while to, you know, adopt this kind of psychology and framework. And other people that have been in there for a little bit, they're just like, yeah, it doesn't even faze me. I'm going fishing and I'm executing against my plan and here are my gains and I'm living a great life.
Yeah, I literally had a, a guy that signed up recently. He's been in Bitcoin since 2013. He joined a couple of days ago, had my welcome call with him and I'm like, oh, how are you finding, you know, the corrections and the dips and you know, the fear that's going around, like, ah, I don't even look anymore. Been Doing this long enough to know I don't care. Right. Versus someone brand new to crypto that's been in maybe three or four months that came in and bought the local top. Because that's where most people do. You know, it's fear, it's worry, it's concern, it's all these sorts of things. Emotion takes over.
That's a good point. We're here for the volatility. And volatility goes both ways. And when you start buying crypto, just know that's your start date. You're going to experience a lot of volatility. The number one thing that's probably going to happen is you're going to buy and you're going to experience a correction. It might go up 10% and then down 30 and you're like, whoa, this is not the thing. But if you stay the course over time, you're going to get those swings both ways. They're going to be much easier and easier. It's like going skydiving the first time. By the hundredth time, you're like, whatever, I don't care. But you understand how this works. You're prepared for it and you're taking advantage of it.
Yeah. Great. I've got a quote for you, Bugs. Shakeouts don't destroy wealth. They transfer it from the reactive to the resilient. Oh, this.
That is one of my favorite quotes. And I think the simplified version is wealth transfers from the hands of the impatient to the patient.
Yeah, that was another one. That was another version of it. True wealth isn't lost. It is transferred from the impatient to the patient.
And that's it. Like, if you literally took all the money in the world and you divided up equally among everyone within whatever period of time, 10 years, 20, 50, 100, it will be back in the hands of the wealthy.
Yeah.
Because it's their psychology and they know what to do with it. Rather than having this kind of new thing and having to learn those lessons and all of these painful mistakes that cost you a lot of money.
Correct. And that. And that is. But that is another lesson. It's just short term thinking versus long term thinking. That's. That's a big one. You know, not getting angry, frustrated. It doesn't help. You know, checking your portfolio every 10 minutes, getting emotional, having notifications on all these sorts of things does not help. If anything just aggravates you. And I know it personally. Like, you know, when we have a big market dip and you load it up, you get that little, you know, the little twang of anxiety. It's like, oh, is this time different? You know, if you're doing that consistently, it's not helpful, it's not going to help you in your life, your partner's not going to like it, you're going to feel like shit, you know. You know, to play the game of crypto you've got to be emotionally, you know, what's the word? Probably emotionally ready for what crypto brings. And it's not just up only forever. In fact, it's the opposite.
You need to be robust, resilient, durable.
Yes.
And, and mate, I'm going to call you out on one. Not having a sell strategy with a certain nft mate, I just want to.
Have a sales strategy in general. But my worst round trip, well, you know, I round trip my first cycle lost hundreds of thousands, but on a single investment, Moonbirds for Those around in 2021 got in on the Moonbirds pre sale. NFT got in at like 6,000 or $10,000. Literally ran to $150,000 in about 3 days. I remember I was in New York at the time and I was, did the literally the same shit that everyone does. Looking at it, showing my friends, look how much money I made. Oh, it's going to go to 500k, it's going to go to 700k. All this just ridiculousness that happens when you make a lot of money. Really quickly, the euphoria takes over and I round trip the entire thing. Now it's probably worth about a buck fifty. You know, I sold it I don't know how long, ages ago. But it's just another, another lesson Burges is to don't get caught up in the mania. The mania is not helpful and if.
You start to experience that mania, that's a good signal. I was livid at this one. So, mate, I was, I was down south with the family. It was 2022, I just joined Collective Shift. I'm pretty sure it was around April time. And I just set up my new structures so I had to write a loan agreement, transfer to my trust, get on the pre sale, sign all this stuff, all this nonsense and in and out of cell reception because I'm on a farm in the middle of nowhere. Internet's not really working. And then this is the one time I had a sales strategy where I said, great, I'm putting in 10k. If it gets to 150k, I will sell instantly. Emotionless wrote it down. Everything I actually would have done, it didn't get in the pre sale. And I was furious because I had no attachments to Moonbirds, didn't give a shit about the creator or what it looked like or anything. I was in it for the money. And this is one I would have executed against with a sell strategy and it would have been epic. But no, you and Matt got it, we're all going to make it and you both wrote it to zero. And I'm just, I'm still filthy about it, mate. I could use 150k, bro.
Oh, yeah, yeah. Hindsight's a wonderful thing. It's very easy to look back and go, this was what I should have done. You know, this is what I could have done. But in the moment, it's difficult. That's. That's a lesson learned. Like you've got to be able to act and make decisions and logical decisions. And I think that's probably my final lesson that I just want to leave everyone on is twice I've nearly gotten scammed on online and it was both because I was rushing, I was in a hurry and I was not emotional emotional. I was not thinking straight. The best one that nearly got me was a full blown Coinbase esque, you know.
Phishing email or something.
It was a. No, it was a WhatsApp message that I received from a Coinbase employee that knew everything about me that then wanted me to get access to or was offering me because they heard who I was and like, I was a sophisticated investor. They wanted to see if I was interested in a private sale that Coinbase were doing on a new investment and they were going to introduce me to their head of investments if I was interested. So then they did.
You told me about this one, didn't you?
Yep. So then they did. Crazy. Then I did an introduction.
Yeah, you were like, this is like Brian Armstrong's like, right? Or something like that.
Next door neighbors, fucking cat's brother, you know, is interested. And they did an introduction to me on WhatsApp to some other person from Coinbase, and all the names and all the numbers were legitimate and these people were actual people on. You could, you could verify online. Obviously it wasn't them. And then it got to a point I can't remember the exact way they were trying to get the investment, but I think it was like, you know, just that sort of the basic stuff. But long story short, I was in a hurry, I was in a rush, I wasn't thinking, I wasn't logical, I was emotional and I was just, you know, in a hurry. It was in the peak of a bull market. So money was flying everywhere and, you know, you felt like if you didn't do something, you're going to miss out. You know, luckily I, you know, at the final hour, you know, actually switched on to what was actually happening. But it's, it was, it was very sophisticated. And it just goes to show again, anytime that you're rushing things and not being logical, you're most likely going to make a poor decision.
Scams happen when you're weakest. So this is, think about this. Let me, let me just set the scenario here, Ben. You've got a, maybe a trade on, or you're heavy in alts, or you put a bit more money in more than you should have. You're not sleeping well, you're seeing the number go down, you're stressed, you've got anxiety loops going, your head, your eyes are burning, you're on your fifth 15th coffee. You're trying to make it right. You can't explain to the Mrs. How much money you've lost and think about that emotional state. And when you're trying to act quickly.
Yeah.
And your cognitive ability is just like, it's, you're about six or seven beers down. You're not the greatest. Yeah, you're rocking it like.08. And honestly, that is where the mistakes happen. And you'll click the wrong thing, you send it to the wrong address, you won't do your normal checks because you want to act fast and you want to correct the mistakes you think you've made. And that is where you get.
Got 100. Every single time. Every single time. So lesson there, folks, listening at home, if you are rushing into something, you feel you've got fomo, you need to do something quickly before you know time's running out. Stop, pause, take a breath, put the phone down, go for a walk. That's anything.
Yeah, you never need to do anything quickly. In crypto, there was one thing maybe you needed to do quickly and that was FTX where we alerted everyone like, hey, this is a bit. And we told everyone like, hey, like, move your stuff now. But apart from that, that like in the last seven, eight years there hasn't been anything like that. And mate, I've got one more. And we talked about hindsight, let's talk about foresight. So this cost me a lot of money as well, having poor structures. And this is tax and legal structures.
Yeah.
So I haven't necessarily needed the legal side yet, but I've set it up anyway. But having bad tax structures, so having everything in your personal name, if You're a high income earner, you're going to pay a lot of tax. In Australia, it's 47% and if you haven't held things for more than 12 months, you don't get the 50% discount on that. That's huge. So think about your structuring and also think about not just tax minimization but also asset protection. So these are things like companies or trusts where they have lower tax rates and you also have that asset protection. Setting that up now and investing in through those vehicles will save you so much money, hassle and time in the future. It's easier to transfer wealth as well. There's things like, you know, when wheels and everything come into play, if you've got that all set up, you don't have to go through probate, those kind of things. It's just an amazing thing to set up that no one thinks about until it's too late. And I know so many people that like, I made a few million bucks in crypto, great, I'll just put it in a trust, I'll pay less tax. Like, well, buddy, it doesn't work like that. You should have done that at the start. So those are the things you want to watch out for. Have a chat to your accountant. It's not expensive at all. Everyone's like, oh, it costs millions of dollars. It's not to get this set up. It is so, so cheap. And then a few hundred bucks each year to do a tax return and you will save thousands, if not hundreds of thousands per year.
Love it. That's our, that's our lessons, folks at home. Maybe you've, you've been through some of these already. Maybe we can save you from not falling the same traps wherever you are on your journey. Hopefully you can learn some from our war stories there. If you want to see exactly how sophisticated investors are growing their crypto portfolios without all this time wasting on charts and influences and guesswork, check out the link in the description. We've got a free training that we put together. It's a proven seven step system that we use at Collective Shift with all of our clients across the world. Whether an executive, business owner, serious investor, no matter where you are, it can help and also understand how we work with our clients. If you are interested in jumping on board, that is in the link below. Otherwise we release episodes each and every week. We'd love for you to subscribe. If you're on YouTube, if you're on your podcasting app, leave us a follow it's how We Grow the podcast each and every week. And we'll see you on the next episode.
Thanks, champions.