In this informal YouTube discussion, Sam Parr, Sean, and Steph dissect the rise of Ryan Cohen—founder of Chewy.com—and his recent activist investments in distressed legacy retailers such as GameStop, Bed Bath & Beyond, and Express. They trace Cohen’s early aggressive fundraising, the massive exit from Chewy, and his strategy of buying sizable stakes in struggling brands to revitalize them, noting his $76 million investment in GameStop that grew to $1.1 billion. The conversation expands to broader market conditions, highlighting the current deep discounts on many growth stocks (Zoom, Fastly, etc.) and invoking Warren Buffett’s “be greedy when others are fearful” mantra as a rationale for opportunistic buying. The panel then debates personal portfolio construction: equity‑bond allocations (90/10 split), cash reserves, and the pitfalls of “buy‑the‑dip” versus chasing losses. They share personal experiences of ignoring daily market noise, the psychological challenges of staying disciplined during drawdowns, and the need to generate active income when portfolio returns stall. Steph proposes a “distressed‑stock ticker” concept for a podcast that would spotlight heavily discounted large‑cap stocks and crowdsource turnaround strategies. Throughout, the dialogue blends admiration for Cohen’s boldness with cautious reflection on risk, liquidity, and investor behavior.
Chapters
Sean, you and I were sent something from our friend Jack. Steph, I'll fill you in. So basically, there's this guy named Ryan Cohen. Ryan Cohen, he started Chewy.com, which is like Amazon for pet stuff, when he was young, right? Sean, I think he was like in his early 20s. And he was aggressive when he started it. He raised a ton of money. He started out of Florida, so he is very much like an individual thinker. He was like, no, we're not doing Silicon Valley. We're going to do this out of Florida. He raised like $1 billion, a huge sum, ended up selling it for $3, $4, $5, $6 billion. I don't know the exact amount. Then it goes public worth many billions. But after doing that, he made, I think, around like $600 million, like a huge amount of money. And after he made that money, there was an article written where he goes, I pretty much put all of my money into two stocks, Apple and Wells Fargo. So he put like all of it in there. And since that article went live, that means that the money that he put in there has gone up 361%. Then about a year and a half ago, he noticed that there was a brand that he loved that wasn't doing so well. And he thought these guys can totally revolutionize the game, but they're just really like getting— they're getting crushed right now. I'm going to buy 10% of the company, which he did for $76 million. And that company was GameStop. And when he bought GameStop, that's when this whole like meme stock thing went down because everyone was like, Brian Cohen bought it. And he actually— it worked. He turned the company around, or at least it's in the process, but it's being turned around. And his $76 million, he turned into $1.1 billion. And he currently still owns like 13% of the company, is on their board of directors. Now, just this morning it was released or announced that he just bought 10% of Bed Bath Beyond. So he's doing the same thing. And this guy is a madman. I think— I'm almost positive he's still only 34, 35 years old. I also researched on LinkedIn. I'm almost positive that it's just him. Like he doesn't have an employee, maybe as an assistant, but it's like just him, like searching around for stuff. So this man's crazy and I love him.
Up 60%.
So his money's already up.
Yeah. Okay. He's amazing.
I feel like there should be like a ticker for just like stocks that aren't small that have fallen like 80+% from their highs. It's like, what crazy operators want to like come in here and totally turn this thing around? I feel like you could also have a podcast about that where you just like you find a stock like Bed Bath Beyond and you're like, look, highs were at $80. It's now at— what was it before this? Like $6. Like, what would you do if you were operating this business and have people like come on and battle like Jeopardy style and see who comes out with the best strategy?
That's kind of cool.
Yeah. Right now there's like a whole bunch of growth stocks that are down, you know, somewhere between 50 and 80% from their all-time high. And, you know, stocks like Zoom and, you know, Fastly and a bunch of others and there's, you know, there's like kind of that Warren Buffett phrase, you know, be greedy when others are fearful and fearful when others are greedy. And it sure does seem like now is a good time to be greedy when others are fearful, right? Like there's a lot of, you know, opportunity everywhere in the market. And so, you know, if these are things that you believe in on a 10-year timescale, then like this is a fantastic entry point.
Uh, here's another interesting one. So I have, I was thinking about this Bed Bath and Beyond thing and GameStop, and my friend Joe sent this to me. So have you guys remember Express?
Yeah.
I don't know if they, if they have that in Canada, Steph, but Express, mostly women's clothes. It's like, it was like fast fashion before that was like even called a thing. So look at what their market cap is. I think their market cap is $250 million right now, but their EBITDA is $150 million. So I think Express is an interesting one too.
Yeah. But you gotta look at like the debt and all, all these other obligations.
They have a, they have a ton of debt.
Yes.
They have a ton of debt. That's the problem. They've got a ton of debt.
What I told Jack was, I go, Ryan Cohen is basically, he's doing the Tai Lopez playbook of buying old retailers and spinning them into like, you know, e-commerce and sort of rejuvenating these big old brands. You know, he's doing the same playbook as Tai Lopez just without being Tai Lopez, which is actually, A great idea in general. That's a great business plan to follow. Do the Tai Lopez playbook without being Tai Lopez is like a, a, a great, great idea.
When people talk about buying, when the, like buy, buy the dip, I hate that. I'm, cuz I'm like, I don't, I don't have any money to buy.
It's like chew the dip.
Yeah. Yeah. That's what I gotta do.
I don't know.
Whenever people say buy the dip, I'm like, with what? I, I don't own anything. What do you, what do I do?
Well, you don't keep any, uh, dry powder. I feel like you always, you're always Mr. Like save safety net with cash and other things. You have dry powder. Why aren't you buying the dip?
I have $100,000 in cash.
Oh wow. Okay. I thought you used to have way more in cash. Now that, now that you're a short-term real estate mogul, you've deployed everything or what?
I've deployed everything. Yeah. I don't, I, yeah, I, I don't have that much cash. I don't have enough. What do people just hold, like keep cash in a checking account?
Yeah, certainly people do that. They do CDs, they do, you know, different, like different versions of like a market-neutral, like, you know, cash position?
I own bonds. I own a ton of bonds, 7 figures of bonds. But I guess—
why do you do that? Who told you to do that?
Uh, it's 5% of my net worth is in bonds.
Who told you to do that? Don't— nobody buys bonds on their own. Everybody gets told to buy bonds.
My, my— a lot of my portfolio is 90/10, so 90% equities, 10% bonds. You know, you don't— like, do you own a bond?
I don't own a single bond.
Steph, do you?
I don't own a single bond.
Really?
But I feel like Sean's right. Like, what rate are you getting on these bonds? Aren't interest rates at like zero?
Yeah, nothing. Like 2%. Yeah.
You're losing money.
It's just like traditional—
You've locked yourself into a money-losing position. Congratulations.
Well, actually, that's a good question. With Havoc going on right now, Sean, from one— is your net worth down from one year ago today? If assuming you did not add any new cash?
Yeah, for sure. One year ago, 'cause one year ago was like a market high, right? Like if you're talking about right after the COVID bounce. So like let's say COVID crash, the COVID recovery all happened in like a 3-month period or 6-month period basically. So let's just take the all-time high last year to today. I gotta be down 25, 30% easily, easily 30%.
I would've thought it would, would've been a lot more because of you have more high-risk stuff.
Yeah. But like a lot of my stuff's in Amazon stock and Amazon stock has done fine. You know, it's down a little bit, but yes, that one's not so bad. And I would say like, you know, that's a, that's a pretty large position. So that's not super, that's not very risky in my opinion. And you know, crypto, Crypto's, you know, down whatever, 30%, 35% from last year, most of it. But I have a few like altcoin bets that have done really well. So like, I was on here talking about Luna not long ago. Luna's up 100%. So it's like, you know, that doubled while other stuff went down 30%. So it's okay, you know, we do all right.
All right.
But Sean, where's your psychology at? Because I feel like, you know, everyone knows the strategy, like, yeah, buy low, sell high, but when this actually happens, when all your stocks or all your investments go down, it's like so hard to actually maintain that psychology and be like, oh yeah, I'm totally gonna put more money in the market. So are you like, is your conviction still as strong as it used to be? Are you like, yeah, this is like awesome, I'm gonna buy the dip, or are you struggling?
Can I, quick interruption, do me a favor, scroll down and you're gonna see a link to The Hustle. So if you wanna stay up to date on the tech and business news you need to know, Check out The Hustle. It's a daily email. I used to help write it. I love it. So check it out. Scroll down below. Let me guess. Don't talk, Sean. Don't talk yet.
Okay.
I have a feeling that this means nothing to you and you're totally cool.
Yes.
About this.
It's actually even better. I don't even look, like I don't look at it 'cause I'm like, oh, why would I look? It's just gonna be down. So I just don't look, which means I don't think about it, which is actually like the correct way I should have been doing it altogether. Like waking up and seeing green, put a lot of nice little pep in my step, but was sort of this like false positive. And, and now I just don't look because I'm like, oh yeah, of course I'm down 5% again today. Like what? I just lose 5% every day or 2% every day. That's just like an average day now. So I just don't even look at it. And because I'm not looking at it, it doesn't matter because I wasn't selling. I wasn't selling when it was going up. I'm not selling when it's going down. So it doesn't really matter the day-to-day fluctuations of it. So now it's just, I just get some time back because I don't like want to go look at it 'cause I don't want to see any carnage. So I'll just like kind of ignore it and just go about my day. And you know, I kind of ask, I'll pause, I'll ask myself, you know, has anything changed? Meaning do I view these investments differently now? Do I no longer believe that these are good investments to be in over like a 5 to 10 year period? No. Okay, so then, you know, what am I thinking about? There's nothing to think about essentially at this time. Do I buy the dip? That's one where, you know, sometimes I do like to just chill and just like sit on the sideline for a bit because I'm a pretty like— I've spent a lot of time in my life gambling. Like I literally played a lot of poker, a lot. Like I've spent so many days in a casino. And so I know the feeling of chasing a loss, trying to win it back. And, and so I just like to make sure that I'm not doing that. So there's a difference between buying the dip. And chasing a loss and, you know, throwing good money in after bad. And so just trying to differentiate between the two, like, am I on tilt or do I actually believe that, you know, this is a good, good entry point and, you know, whatever else. So I would say the one thing this does do is it heightens my focus on earning money because like, oh, I need to like earn money. I can't just rely on my investments, you know, completely. So like, what do you know? I got off my ass, I taught my course and I like submit my invoice for the podcast and I like, I do things that will bring cash in because otherwise, you know, it's easy to get lazy when everything's just going up so much. There's many days where you could just look at your portfolio and just be like, wow, that was a whole year's worth of salary just today. Swing up. So that kind of makes you kind of lazy to do the work that day in a way, right? Because it's like, oh, well, if this just could earn that much money just doing nothing every day, why do I need to go hustle for that? That next dollar. I feel you.
Yeah, I feel like a lot of people are feeling that way. They're like, oh right, I have to work. Like, this doesn't last forever.
Yeah, which is great. Very healthy, very healthy position to be in.
