You might not believe me, but at one point in my trading career, I was holding 70 positions overnight.
Not 2, not 5, not 10… 70.
If you’re newer to trading, that many positions probably sounds insane. And honestly? Looking back, it kind of was.
But it made me a ton of money…
And, more importantly, it taught me some of the most important lessons I’ve ever learned about the market.
Even with all the green that came from that time in my trading career, there’s a lot I would have done differently…
P.S. Wanna know what I’d do if I had to start over from zero?
I was recently asked this question.
How It Started
It wasn’t something I planned.
It grew organically out of what was happening in the Over-the-Counter (OTC) market in late 2020 and early 2021.
My mentor, Tim Sykes, had been saying it was the hottest market he’d seen since the dot-com bubble in 2000…
And he was right. Everything was running. Weed stocks. Electric vehicles. E-sports. Every sector you could name had names underneath it that were waking up and running hundreds of percent.
I was watching a trader I respected who ran what I’d call a shotgun approach. He was buying a vast basket of low-priced OTC stocks that were building bases with volume, letting the winners run, and trimming along the way.
I watched his alerts. I watched his process. And I noticed something that caught my attention right away.
Pretty much every single stock he bought kept going up.
Not some of them. Most of them.
And it wasn’t just his picks. It was the entire OTC market. Everything was rising together, moving like one giant sector. If one name was running, the sympathy plays were right behind it.
So I started building positions. Sector by sector. Name by name. And before long, I had 70 overnight positions in my account at the same time.
What Worked
The approach made me a lot of money.
Because when an entire market rises together, a wide net catches a lot of fish.
I had names go five hundred, a thousand, even five thousand percent. I put ten grand into some of these stocks and turned them into fifty, sixty, seventy thousand. I had a handful of swing trades that cleared six figures on their own.
The math worked because the market worked. When the tide rises, everything floats, and I had a boat in every corner of the ocean.
The key for me was that I didn’t just hold blindly…
On my biggest winners, I locked in gains into strength. I’d sell the majority of the position into the run and hold a small piece, a quarter of my shares, just to let it ride.
That discipline protected most of my profits even when things eventually turned.
What I’d Do Differently
Here’s where I have to be honest with you.
When the market shifted, I held on too long.
I saw it coming. The signs were there. One morning, I woke up, and every single one of my 70 positions was in the red. Every single one.
The whole OTC market had rolled over at the same time, like someone flipped a switch overnight.
That was the moment. That was the exit.
I slowed down my day trading fast… That part I got right.
But my swing positions?
I held. I told myself they’d bounce back. I told myself the sectors were still good. I told myself to be patient.
What I forgot was that a lot of what I owned was OTC junk, which is usually why they trade on the OTC in the first place.
These were companies that weren’t worth the market caps the mania had given them. And when the mania ended, those valuations fell back to earth, and hard.
I gave back a lot of gains I didn’t have to give back if I had gotten out of those names earlier.
The lesson isn’t that the shotgun approach doesn’t work.
It absolutely worked. Guys, it made me hundreds of thousands of dollars during one of the greatest OTC runs in history.
The lesson is that the same discipline you use to get in has to be there when it’s time to get out.
When your entire portfolio panics in a single morning, that’s the market telling you something. Listen to it.
Lock in the gains. Exit into strength when you have it.
And never ever fall so in love with a position that you forget why you got in.
70 overnight positions taught me that.
– Jack Kellogg
