Easter 2021, my mom’s kitchen table. Somewhere between dinner and dessert I mentioned, casually, that I’d crossed a million dollars. One of my sisters asked what that even means. So I explained net worth at the kitchen table, everybody nodded, and the conversation moved on to something else.
Nothing was celebrated. To be fair, I hadn’t given anyone much to celebrate with, because I’d told almost nobody what was happening on my phone screen. Not even my dad.
I was 23. My position was on its way to about $2 million. And over the next stretch I watched it ride all the way back down to roughly $150,000 without ever selling the core of it. Not on the way up. Not on the way down.
So if you got here searching when to take profits, I’m the cautionary tale, and I’ll give you the answer my tuition paid for up front: take them on the way up, exit the way you entered (slowly, in pieces), and treat any gain you haven’t converted as a loan the market can call back whenever it feels like it. Everything below is what it looked like to learn that with my own money.
The kitchen table
What I remember most about that Easter isn’t the number. It’s how alone the number was.
A private win you can’t explain to anyone is a strange thing to carry around. I was living an ordinary life in northern rural Wisconsin, at my dad’s place, an Escalade and an old Lincoln in the driveway, and meanwhile my phone was showing me a life-changing figure that nobody around me could see or would’ve believed. I didn’t hide it out of strategy. I just didn’t know how to say it out loud without it sounding made up. Looking back, I think part of me knew it wasn’t real yet. Money on a screen is a screenshot until you sell.
Six figures in, slowly
I started buying crypto steadily through 2017 and 2018. Not one dramatic bet. Just consistent buying over time, until roughly six figures had gone in, which was basically all my money. I was young, my expenses were low, and I believed in the thesis more than I believed in anything else I could’ve done with it.
I’d already learned by then that every trader touches the stove eventually. What I hadn’t learned is that the stove has a second burner, and it’s reserved for the people who were right.
The plan was $7 to $9 million
The position was XRP. I had a technical target of $7 to $12 on it, built off a Fibonacci extension (the 4.236, for the three people reading this who want the detail), and at my size that penciled out to seven, eight, nine million dollars after taxes.
And I have to be honest about what that number did to my head, because this is the part that actually matters. The money was already spent in my imagination. Houses, real estate, bonds, trusts for the family. I’m not exaggerating when I say part of my daily routine was dreaming about what to do with it. I’d visualize the whole thing down to the scratches in the chrome. That habit has served me well in every other area of my life. Here it did something sneaky: it converted a target into a certainty. I wasn’t holding a position anymore. I was waiting for a delivery.
Notice what’s missing from that plan. There’s no line in it that says what I’d do at $2 million. Or at $1 million. Or at any number that wasn’t the destination. I had an entrance strategy and a fantasy. That’s not the same thing as having an exit.
The top
Then the timeline got weird. On December 22, 2020, the SEC sued Ripple. That should’ve been the end of the story right there. Instead XRP ran anyway, all the way to about $1.96 on April 14, 2021, and somewhere in that run my position peaked at right around $2 million.
I was 23 years old with two million dollars on a phone screen, standing in my dad’s driveway in rural Wisconsin.
Here’s what the money actually bought me at the top, and I want to be precise about this: you drive around with the windows down, the sun was brighter, the music was clearer, and I smiled a lot more. That’s it. That’s the whole list. I didn’t buy a house or a watch or a table at a club. What I bought was a mood.
And was I grateful? No. Not gonna lie, gratitude wasn’t in the building. I was extrapolating. Two million wasn’t an outcome to me, it was a checkpoint on the way to eight. When your plan only has one exit and it’s four times higher than the price, every green day reads as confirmation and every red day reads as a discount.
The ride down
May 2021 broke it. Not all at once, which is the part people who’ve never lived it don’t understand. A crash you could react to. This was slower and meaner than that. It constantly kept you thinking we’re gonna go back up. Every bounce looked like the turn. Every month there was a reason to wait one more month. The lawsuit had put a ceiling on my token’s cycle while the rest of the market went and made new highs without it, and I sat there holding, right through all of it, watching $2 million grind its way down toward $150,000.
I’ll tell you the strangest thing about it, and I’ve thought about this a lot: it was worse in hindsight than it was living through it. Living through it, there was always hope, which is exactly what made it impossible to act. The full weight only landed later, when the hope was gone and the math was just sitting there being the math.
I never sold the core position. I rode the entire thing. There’s a whole essay on this site about why traders give back everything they made, and I wrote it the way you write about a scar.
The one thing I bought
One purchase came out of that whole era. A flagship Cadillac, paid in cash.
When I was a kid, my cousin had a toy concept Cadillac, dark blue over cream, and I never forgot it. The car I bought is that exact colorway. On purpose. Twenty years between the toy and the title, and I’d be lying if I said signing for it didn’t feel like closing a loop.
Now the honest part. To help pay for it I sold about $40K of XLM, a smaller position, and at that token’s later peak those same coins would’ve been worth around a quarter million. So even the one time I did sell, I managed to do it wrong in the other direction. I sometimes think of that as the car’s true sticker price. And I still told no one what was going on. My dad watched me buy a Cadillac in cash and I just let it be a mystery.
Here’s a stat about me that took years to understand: I spent more recklessly making $10K to $30K a month than I ever did with millions on the screen. Income feels like permission. A portfolio feels like a scoreboard you don’t want to touch. Neither feeling is telling you the truth, but only one of them was buying rounds.
What I’d do differently
This is the spine of the piece, so I’ll keep it plain.
Take profits. Actually take them. Not because the thesis is wrong, but because you being right about the thesis was never the only variable. An SEC lawsuit landed on my position out of a clear blue sky. Sound thesis, uncontrollable circumstance. Risk management, in plain English, is just the admission that stuff you can’t predict is allowed to happen to trades you researched.
Exit the way you entered. I bought in slowly over two years, and somehow expected to sell in one glorious moment at the top. Nobody sells the top. Selling in pieces on the way up is what that actually looks like in real life.
Pull an insurance policy off the table early. If I’d taken even a few hundred thousand out on the run up, everything after changes. That money is options: it keeps you calm, it keeps you patient, and it means the worst case is a disappointment instead of a restart. You need to keep your options open. I didn’t, and for a long stretch of my twenties the options stayed closed.
Stay cheap while you wait. My low expenses were the one thing I got right in this whole story. They’re the reason a 92% drawdown was survivable at all. And know what you’re signed up for, because this asset class runs very long and very aggressive roller coasters, and being built for that emotionally matters more than any chart.
My best pick of that era makes the same point from the other side. I put $5K into XDC and watched it touch roughly $500K at its peak. A hundred-to-one winner. Same story, same ending, same guy who hadn’t learned the lesson yet. Being early twice and paid zero times should tell you the problem was never the picking. I’d already sold 300 domains too early as a kid, so apparently I needed to learn the timing lesson from both directions before it stuck: a windfall without an exit framework isn’t wealth. It’s a loan, and the market decides the terms.
A cheap lesson, praise God
All of this happened before I knew Christ. I want to say that plainly, because it explains the ending better than any trading lesson can.
At the top I wasn’t grateful, and honestly I wasn’t ready. Not for the money and not for what the money would’ve made me. Looking back now, I see the whole ride as part of becoming someone who could actually steward that kind of number instead of being dissolved by it. A cheap lesson, a few million bucks, that will save me, hopefully, hundreds of millions, praise God.
That’s not me putting a bow on a loss. The loss was real and I hated it. But I’ve watched what happens to people who catch the number before they build the character, and I no longer think I got unlucky. I think I got tuition. Some of the best money I ever made is money I watched disappear.
Take the profits. Keep your options open. And if you’re currently somewhere on your own ride down, holding and hoping, I’m not going to pretend I’d have listened to this piece at 23 either. I just know somebody in that kitchen finally deserves a straight answer about what the number means: nothing, until you sell.
Tyk Sullivan
Serial entrepreneur in Tampa, Florida. Founder of Plutus Capital and NUMEN. More about Tyk →