Friend lost $10 MILLION selling Bitcoin to rebuy cheaper – hear his story & avoid the same mistake!

Published May 11, 2025

  • YouTube Video Transcript

    00:01 Hey everyone. A friend of mine missed
    00:03 out on $10 million by trying to sell his
    00:07 Bitcoin when it felt like it was high
    00:10 and then planning to buy it back uh when
    00:12 it was lower. So, here’s the quick
    00:14 story. So, I’ve got a friend who was in
    00:16 Bitcoin from very early on, very, very
    00:19 early on. And um ultimately he he had
    00:23 somewhere between 3,000 and 4,000
    00:25 Bitcoin. Uh but ultimately traded
    00:27 virtually all of them in for Dogecoin.
    00:30 Uh and obviously Dogecoin did not
    00:32 perform well. He ultimately sold all of
    00:34 the Dogecoin for I don’t know something
    00:36 like $100,000 or something like that. So
    00:38 obviously starting out with close to
    00:40 nothing and ending up with $100,000 is
    00:43 great. except had he held on to that
    00:45 Bitcoin, it would have been worth right
    00:47 now between $300 million and $400
    00:51 million. So, you know, but that’s not
    00:53 the that’s not the main point of this
    00:55 story. Um, that’s the main point of the
    00:57 story. Don’t ever trade your Bitcoin for
    00:58 something else and don’t ever buy
    00:59 anything in crypto other than Bitcoin
    01:01 because that that cost, you know, $300
    01:04 million plus
    01:06 uh in this case. But what this story is
    01:08 about is uh $10 million. the story of
    01:11 $10 million because when he swapped his
    01:13 Bitcoin for Dogecoin, he kept 100
    01:16 Bitcoin. And uh his thought was, I’m
    01:18 always going to have 100 Bitcoin. If
    01:20 Bitcoin ends up being worth a lot one
    01:22 day, I’ll always have 100 Bitcoin. But
    01:24 he noticed that the price went up and
    01:25 down a lot as it always does because
    01:27 Bitcoin is a volatile asset early in its
    01:30 price uh cycles, uh early in its
    01:32 lifespan where we are right now. And and
    01:35 back then when the story took place, it
    01:37 was even earlier in Bitcoin’s life
    01:39 cycle. and Bitcoin was $100 a coin. So
    01:43 he was looking at the price of Bitcoin
    01:44 and it was $100 a coin and Bitcoin had
    01:47 become worth a penny. That was a big
    01:48 deal when Bitcoin was worth a penny. And
    01:50 then it was a much bigger deal when
    01:52 Bitcoin was worth a dollar. And here it
    01:54 was up at $100 per coin. So his 100
    01:58 Bitcoin at $100 per coin was worth uh
    02:03 $10,000. And he thought, well, I want to
    02:06 have more than 100 Bitcoin. Um, I know
    02:08 what I’ll do. I will sell them for
    02:11 $10,000 and then I will wait for the
    02:14 price to drop and then I’ll buy them
    02:16 back at a price less than uh less than
    02:19 $100 per Bitcoin and then it’ll be
    02:22 great. Um, the challenge was uh, of
    02:26 course, $100 seemed high because
    02:29 everything seems high when you’re
    02:30 hitting it for the first time. So he he
    02:33 thought $100 a bitcoin, how much higher
    02:34 can it really go? like $100 a bitcoin is
    02:37 really high. Um anyway, and it seemed
    02:39 like it would go back down lower. So he
    02:41 sold it for 10. He sold 97 of his 100
    02:44 bitcoins. So he only had three left. He
    02:46 sold 97 for
    02:47 $10,000 planning to buy them back. Well,
    02:50 you know, life got bit got busy and
    02:52 people get distracted and all that sort
    02:54 of stuff. And by the time uh he was
    02:57 checking sort of judiciously to see if
    02:59 it was time to buy the Bitcoin back, the
    03:02 price instead of going down, enabling
    03:05 him to buy more Bitcoin for cheap, the
    03:07 price had instead gone up to $300 per
    03:10 Bitcoin. Uh so now this $10,000 of
    03:13 Bitcoin was now worth $30,000 of
    03:16 Bitcoin. Well, he didn’t want to buy a
    03:18 100 Bitcoin back or in this case 97. He
    03:21 did not want to buy the 97 bitcoin back
    03:23 for $30,000 because he had just sold it,
    03:27 I don’t know, 6 or eight months prior
    03:29 for 10,000. And of course, if you just
    03:31 sold something for 10,000, it seems
    03:33 ridiculously expensive to turn around
    03:36 and buy the same thing back for triple
    03:39 what you uh what you just sold it for.
    03:41 So, he decided not to do that. that he
    03:43 decided just to sit on his three bitcoin
    03:45 and not buy the 97 bitcoin back uh for
    03:49 $30,000 because again he had just sold
    03:51 it, you know, earlier less than a year
    03:53 prior for $10,000. So, as a result of
    03:57 all that, when all the dust settled, he
    03:59 had the I don’t know, I’m guessing
    04:01 $100,000 uh something, you know, low six
    04:04 figures, whatever, uh from the Dogecoin,
    04:07 which again would have been worth $300
    04:09 million had he kept it in Bitcoin. and
    04:12 then uh he could have had and would have
    04:15 had the $10 million had he not sold it
    04:19 um and with the intention of buying it
    04:21 back. So what could we learn from that?
    04:24 Uh what we can learn is don’t do that.
    04:26 So right now $100,000 seems like a lot
    04:28 of money per Bitcoin. So, there are a
    04:31 bunch of people who are looking at the
    04:33 price of Bitcoin and thinking at
    04:35 $100,000 exactly what my friend thought
    04:38 at $100, which is, wow, this seems high.
    04:42 It seems to go up and down a lot. How
    04:44 high can it really go? Maybe this is as
    04:46 high as it’s going to go for the time
    04:48 being. Maybe I should sell my Bitcoin
    04:50 and buy it back at a lower price. And I
    04:53 can just about promise you if you go
    04:55 down that road, you will have the same
    04:57 experience that my friend had. Um, I
    04:60 don’t know how much money you’ll end up
    05:01 losing. Hopefully not $10 million or in
    05:04 the case where he converted his Bitcoin
    05:06 to Dogecoin back in the very early days
    05:08 of Doge, he was one of the first people
    05:10 uh to own Dogecoin. Um, but regardless,
    05:14 you know, that first ma mistake cost him
    05:16 somewhere between 300 million and $400
    05:18 million. And the second mistake of
    05:20 selling the Bitcoin and planning to buy
    05:21 it back at a lower price cost him an
    05:24 additional $10 million. So, don’t make
    05:26 that mistake. on its way up. Every price
    05:30 Bitcoin hits seems high. I remember when
    05:34 $35,200 I remember when I looked at my
    05:37 watch and I saw
    05:38 $35,200 and thought, “Wow, that is
    05:41 high.” Like, how high is it even going
    05:43 to go? Like, that’s really high. I
    05:45 remember looking at my watch and seeing
    05:47 $62,000 and thinking, “Wow, that is
    05:50 really high.” Like, how much higher is
    05:52 it going to go? Like, that’s really
    05:53 high. I remember looking at my watch
    05:56 where I tracked the price of Bitcoin and
    05:58 seeing a price of
    05:59 $92,000 and thinking, “Wow, that’s
    06:02 that’s high.” Like, Bitcoin’s high right
    06:05 now. I look at my watch, it is
    06:08 $104,000. And I think, “Wow, that’s
    06:10 pretty high.” Like, that’s
    06:12 high. If I sold my Bitcoin every time it
    06:15 felt high, I would have sold my Bitcoin
    06:18 back when it was $20,000 and not had any
    06:21 anymore. I’d be sitting around waiting
    06:23 to buy my Bitcoin back and it would just
    06:25 leave me behind at that point. I really
    06:28 would miss the boat. I really would be
    06:30 late to the party. Um, but you’re not
    06:33 late to the party and you didn’t miss
    06:34 the boat as long as you buy Bitcoin and
    06:36 hold on to it. Uh, the only way you can
    06:38 really miss the boat is by not buying
    06:40 Bitcoin at all or buying it and then
    06:42 selling it and then, you know, look back
    06:45 in the future and you could have made 10
    06:46 times your money or 100 times your money
    06:48 or whatever it ends up being. uh maybe
    06:51 more than 100 times your money. Uh
    06:52 Michael Sailor is predicting $13 million
    06:55 per Bitcoin, which is roughly a$130
    06:58 times your money. Um and he’s predicting
    07:01 that in the next 20 years or so. So um
    07:04 we don’t know what the uh uh
    07:07 upside of Bitcoin is. All we know is
    07:09 that I believe it will outperform every
    07:11 other asset. And if it outperforms every
    07:13 other asset, then that means that’s
    07:15 where you should keep money that you
    07:17 want to outperform every other asset.
    07:19 And um and on its way up there will be
    07:22 numerous prices that feel high. Uh and
    07:26 then you’ll be tempted to sell your
    07:27 Bitcoin and don’t do it. Don’t sell your
    07:30 Bitcoin. Everybody who does that ends up
    07:32 regretting it. And people plan to buy
    07:35 their Bitcoin when it’s low, but when it
    07:37 when the price goes down, everybody gets
    07:39 scared because when the price is down,
    07:41 there’s reasons it’s down. and
    07:43 everybody’s freaking out and it’s going
    07:44 down and everybody’s not they don’t have
    07:46 the courage they thought they were going
    07:47 to have when it was going up to actually
    07:49 buy it when it’s down. So even people
    07:51 who think they’re going to buy Bitcoin
    07:53 when it’s down tend to not do that
    07:56 because by the time it is down, they
    07:57 freak out. And they’re freaking out for
    07:58 the same reason the whole market’s
    07:60 freaking out, which is why the price of
    08:01 Bitcoin is down. So very few people have
    08:04 the courage and conviction to actually
    08:06 buy it when it’s down. And a lot of
    08:09 people screw up and sell it when it
    08:11 feels like it’s up. So hopefully that
    08:13 won’t cost you $10 million like it cost
    08:15 my friend uh and it’s cost many other
    08:17 people lots of lots of other money. Um,
    08:20 so another friend of mine, uh, we had
    08:23 dinner a while back, uh, or lunch, I
    08:25 guess it was, lunch, and they were
    08:26 telling me that they had bought a bunch
    08:28 of, uh, or not, I don’t know if it was a
    08:30 bunch, they had bought Bitcoin, some
    08:32 meaningful amount of Bitcoin at a price
    08:33 of
    08:34 $5,000. And, uh, they had, you know,
    08:37 bought it because, uh, other people at
    08:39 their CrossFit CrossFit gym were buying
    08:41 Bitcoin, etc., etc., and they bought it
    08:43 at 5,000. I was like, “Oh, well, you
    08:45 know, what happened next?” They were
    08:46 like, “Well, it went up to 20 and I sold
    08:48 it.” I was like, “Well, why’d you sell
    08:51 it?” And they were like, “Well, because
    08:52 like like 20 is like four times as much
    08:55 as five.” Like, so it seemed to be way
    08:57 up. So like why wouldn’t you buy it at
    09:00 five and then you sell it at 20? And the
    09:02 answer is because one day it’s worth 105
    09:05 and one day it’s worth 200 and one day
    09:07 it’s worth 500 and one day it’s worth,
    09:10 you know, a million dollars a coin. Like
    09:12 that’s why you don’t sell it at 20,000.
    09:14 So they made four times their money.
    09:16 They could have made, you know, four
    09:18 times five. They or uh they could have
    09:21 made 20 times their money between $5,000
    09:24 and $105,000. They could have made 21
    09:27 times their money. 21 times your money.
    09:30 Now, how often in your lifetime do you
    09:32 get a chance to make 21 times your money
    09:35 in relatively few short years? The
    09:37 answer is rarely. That that opportunity
    09:39 rarely comes along. So, they locked in a
    09:42 win at 4x, which is insane because they
    09:46 didn’t really lock in a win at 4x. They
    09:48 locked themselves out of an additional
    09:51 500% return. A 4x could have been
    09:55 21x, but it wasn’t because they sold
    09:58 their Bitcoin. So, don’t sell your
    10:00 Bitcoin. Um, I mean, well, don’t sell
    10:03 unless you’re, you know, using Bitcoin
    10:05 to make your life better. Um, and that’s
    10:08 the point of money and that, you know,
    10:10 at that point it is what it is. But, uh,
    10:12 anyway, don’t sell your Bitcoin. You’ll
    10:14 regret it. It will probably the Bitcoin
    10:16 you sell will be unaffordable to buy
    10:19 back later. Like, you literally will not
    10:20 be able to afford to buy back to get as
    10:23 much as you have uh, if you had before
    10:25 you sold Bitcoin. So, and certainly
    10:27 don’t sell it with the plan of buying it
    10:28 back later at a cheaper price because
    10:30 you’re probably going to get, you know,
    10:32 uh, left in the dust. And plus, what is
    10:34 a what does a cheaper price even mean?
    10:37 Does that mean it drops from 104 to 98
    10:40 or 94, 92? Are you going to only buy
    10:43 Bitcoin if it goes back to 85? What if
    10:45 it goes back to 75? You know, what if
    10:48 we’re in a massive worldwide recession
    10:49 and it goes to 75? Are you going to
    10:51 freak out and say, “Well, I can’t buy it
    10:53 now because the whole world’s on fire.”
    10:55 Like, there’s no there’s no way of
    10:57 knowing what high is. There’s no way of
    10:59 knowing what low is. And if you let
    11:02 yourself be tricked into believing that
    11:04 you can time the market or time the
    11:06 price, I promise you’re gonna just cheat
    11:08 yourself out of Bitcoin. Don’t do that.
    11:11 You can’t do that at stocks. You can’t
    11:12 do that with bonds. You can’t do that
    11:13 with commodities. It, you know, they all
    11:17 work the same way where it, you know,
    11:19 every price that’s high feels high.
    11:21 Every price that’s low feels low. And
    11:24 then you only realize in retrospect that
    11:26 the lows were not low at all and the
    11:27 highs were not high at all. And you
    11:30 totally got it backwards. you got left
    11:31 in the dust and you cheated yourself out
    11:33 of financial freedom. So, don’t do that.
    11:35 Uh, just buy as the the same advice I
    11:38 always give and that I’ve given for
    11:39 years. Buy as much Bitcoin as you
    11:41 possibly can and hold on to it for as
    11:43 long as conceivably possible. And the
    11:45 only reason you should part with your
    11:47 Bitcoin, like I do when I buy stuff with
    11:49 my Coinbased debit card, is to improve
    11:51 the life of me and my family. But even
    11:54 then, every two weeks when a paycheck
    11:55 shows up, I buy more Bitcoin. So over
    11:58 time I am accumulating Bitcoin even
    12:01 though I’m also spending it. But if you
    12:03 are in the mode that you uh you know if
    12:07 if you’re not spending it for living
    12:08 expenses but only for things that make
    12:10 your life better in a significant way,
    12:12 well that’s fine. That’s the point of
    12:13 money. Just realize whatever amount
    12:15 you’re spending is going to be really
    12:17 hard to get your hands on that much
    12:18 Bitcoin in the future because in the
    12:20 future it’s going to be worth a lot more
    12:21 than it is now. So don’t sell your
    12:23 Bitcoin. Do not sell your Bitcoin and
    12:25 plan on buying it back at a cheaper
    12:26 price. uh buy as much Bitcoin as you
    12:29 can, hold on to it as for as long as
    12:30 conceivably possible. That is the
    12:32 formula. That has always been the
    12:34 formula. Have a great day, everyone.
    12:35 Thanks.

A friend missed out on $10 MILLION by trying to sell his bitcoin and then buy it back later at a cheaper price. Here’s the story. Don’t make the same mistake!

**Originally Recorded 5/11/2025**

Share this content

Disclaimer:

The content provided in this post is for educational purposes only. It should not be considered financial, investment, or trading advice. I am not a licensed financial advisor, and all opinions expressed are my own. Always conduct your own research and consult with a qualified financial advisor before making any investment decisions. Investing in Bitcoin or any other assets carries risk, and you should never invest more than you can afford to lose.

Post category:

  • Facebook Live

Subscribe to Joel's Friday Roundup ✉️

Stay current with the latest bitcoin insights with the Friday Roundup newsletter –  Joel’s latest posts from the week, wrapped up in a single email for easy viewing. 

Global Email List Subscription Form

NOTHING for sale. No SPAM ever. Unsubscribe anytime.