In this interview, the host (Speaker A) and guest Colin discuss how founders and high‑net‑worth individuals transition from merely accumulating wealth to actively defending it. They stress the foundational “don’t lose money” rule, explaining the math of loss recovery (losing 50 % requires a 100 % gain to break even) and how this mindset should dominate decision‑making. The conversation references historical market shocks—oil price swings, the 2014 “Black Thanksgiving,” and COVID‑19—and notes that many of these events saw rapid V‑shaped recoveries, underscoring the importance of resilience. They critique the echo‑chamber culture of tech and shale bro communities, where discussing money is taboo, and argue that vulnerability and peer advisory boards can dramatically improve outcomes. Personal anecdotes illustrate costly mistakes, such as over‑allocating to alternatives and making outsized checks without external feedback, which the speakers claim could have been avoided with a small group of smarter peers. The dialogue also explores a perceived cultural shift: more founders now openly share financial losses and scars, believing that sharing painful stories shortens others’ learning curves. The interview concludes with reflective questions about the meaning of wealth after experiencing both riches and near‑ruin.
Chapters
What I teach people is fundamentally we all start as accumulators of wealth, but at some point you have to shift your mindset to being a defender of wealth.
And again, I don't even know when— I don't know, I got Instagram, what, like 4 years ago because some snowmobiling brand wanted to feature me and I didn't have— they're like, what's your tag? I'm like, well, I don't have one, so I've got to get one, right? I don't know when Ray Dalio spooled up his account. I'll tell you right now, 10 years ago I was not following Ray Dalio on Instagram and it's the old like, don't lose money, right? Because if you lose half, then what do you have to do? You've got to double it to get back to par. A friend of mine from high school, she blew through and stayed with me last year and she was like, Colin, like, like, you know, my family is like really rich, right? I was like, yeah, like, you know, this was the '90s. It was high school. I couldn't really look you up. Like, I kind of figured your last name was on a building at Harvard and also at our high school. Okay. Like, I kind of figured. And, you know, come to find out, really rich. Really rich. Like, and she just talked about how they do it. She's like, yep. You know, at 27 you get invited behind the curtain. I mean, it's like Rockefeller type stuff, not the Rockefellers, but similar, right? At 27 you get invited behind the curtain, you get your piece. The principal's not yours to play with. The proceeds are, and you get a vote. And I guarantee like a lot of these, you know, just probably a bullet list of a dozen aphorisms like the Ray Dalio don't lose money, right? That's in many ways like that playbook, just a dozen bullets I think would elevate people so much in some of these instances we're talking about. Doesn't need to be full-blown MBA, doesn't need to be a, you know, a book this thick, but just 10 or 12 guidepost points I think would go a long way.
Yeah, totally. I mean, the don't lose money is one of my fundamental lessons, you know, for exactly that pesky math problem you just talked about, right? Is if you lose half, now you have to double to get back there. I think especially because you and I both came up in a gold rush, there is a tendency to believe that the good times are never going to end. And there was a couple of, you know, quick price crashes and stuff in there. But I mean, it was almost just a pure gold rush for nearly a decade.
Do you listen to this guy Arjun Murthy at all? Great dude. He's a— he's at Veritown. He used to be at Goldman. Did a bunch of great work on like V-shape versus U-shape price recovery. Right. And it was like, all right, great financial crisis. The contagion came from the mortgage market. Oil went from over $147 to $40 and back to $110 in 5 months.
Blink of an eye.
Then, you know, the Black Thanksgiving of '14, right? Like that was contagion within our industry. It lasted for a long time. COVID, snip snap, right? Came from without. So yeah, you had a bunch of these instances of like, sure, you had price excursion, but you had very rapid price recovery.
Almost can't lose. I mean, in many cases, printing money, we almost couldn't have forecasted the writing on the wall because it's— I mean, it was almost like you can't lose.
We talked about like Northeastern liberal academic echo chamber earlier.
Yeah, right.
We were all living in like Texas shale bro echo chamber, right? Which is probably not too different from, you know, Palo Alto tech bro echo chamber, right?
Right.
Everyone's making so much money. I was skiing with a buddy of mine who was sort of roughly in the Silicon Valley Bank ecosystem the day that they failed. Yeah, right. And I think for a lot of these people in tech, you know, they had never— when interest rates started going up and all of a sudden their future cash flows were worth less and so their valuations deflected down, these guys were like What do we do? Right. That's a fragile— that's also— that's a fragile business model. So just, I think, being deeply interrogating what you're doing and stress testing it in your own mind and doing it in a way that puts a floor under the outcome. It's not sexy, it's not fun, it's not bro-y, right? You're not talking about that at the bar at 2 a.m. about like, look at my allocation to muni bonds. But it's pretty cool to be sitting on a lake when you're 50. Yeah.
And that's it. And that's, you know, when I look at some of my worst investment decisions, If I had, you know, a peer advisory board and I went and laid out my net worth and the decisions I was making, they would have laughed me out of the room.
Sure.
And if I really think about it, right, I get quiet with myself. I knew, I knew that I was writing checks that were outsized, but I couldn't stop.
Dude, I had a, I had a mid, you know, mid to upper mid seven-figure net worth. Okay. And I had a 60% allocation to alts, not just alts, but one alt.
Right. Right?
Like, that wouldn't pass muster with anybody.
Totally. There is, for me at least, there was like a voice in the back of my head saying, this probably isn't it. And I didn't justify my decision to anybody, right? We operate in a vacuum, you know, we're not supposed to talk about money. So I didn't go to anybody and lay out my portfolio because it's almost like, you know, being naked in front of someone. Oh, it's not, it's not something that we discuss. Man, like, if I could just go back and go, if I gathered, you know, you know, 3 guys that were smarter than me in the room and said, hey, this is what I'm thinking about doing. Does this make sense to you? That one inflection point would have changed my life. Like, I hate to, I hate to do public math here. I went through with a wealth manager friend of mine, and like, if I had just made a few better decisions, like, I'd be sitting on $50 million liquid now. Newsflash for anybody listening, I'm not, right? Right. And, and there's decision points. This is not a wildly different path.
I'm 44. You're also being in my 40s or if it's just being in the year 2025, I can't separate the two variables. You know, it feels like my buddies are a lot more open to talking about their losses, personal, financial, emotional, all that. Right. And to like starting to do that peer advisory board kind of process informally over a cup of coffee or whatever. But I don't know, you seeing something similar? Yeah.
I mean, this is— I mean, this is what I do. This is why I started.
But has there been a cultural sea change or is it just because I'm coming into that time of life where people have enough scars, they're willing to talk about them? One of my core values is vulnerability.
And there's always an opportunity to go first, right? And so my thought is like, if I share my story and if I tell people about, you know, look, it's way more interesting to hear about the time that I lost $1.5 million than it is, you know, no one cares how much money we made, right? Ultimately, I think there is something so sacred about sharing those scars. It invites other people to open up. And I do think there has been sort of a cultural shift with shows like this one. And, you know, if I, I mean, kind of like we said earlier, if I can help one person, don't just be like, Hey, man, you know, I can't guarantee that, you know, you'll skip all of the pain, but hopefully we can shorten that learning curve just a little bit.
Sure.
Right. So, you know, I do think there is a trend toward— number one, I think, I think 10, 15 years ago, at least my perception when I was starting out was everyone else has it all figured out. And I'm, and I'm learning as it turns out, you know, the more I meet guys like you, not everybody has it. In fact, most of us.
And that's true in their family lives, true in their professional lives as well.
For me, really comforting to know, like, oh man, here's a guy I just met a year ago. We came up in the same path and our stories look really similar. Sure.
Cool.
Turns out there's a lot of us, right? And the more entrepreneurs I talk to, the more folks I realize, like, we're kind of all the same. And the first time I shared my story was a few years ago on a stage at Baby Bathwater. And like 25 people lined up and were like, oh my God, me too. I've been rich and broke so many times. And I've never told anyone, right? And so I do think there's a cultural shift.
Yeah, and I think if you can, you know, if you're talking Rich Bro, if you just think of a sine curve, right? If we can just truncate the bottom of the sine curve, sure, maybe you're still going to have losses, but they're not going to go as deep.
Totally. You know, now having been through this, right? Having stood on the top of the mountain and watching it slip through your fingers, what does wealth mean to you now? And And how do you think about that?
Really? I mean, it's not because he said it, but I think he said it really nicely. I mean, it's the Scott Galloway definition, right? It's that your asset does the yield from your assets cover your burn. And I was talking with a dear friend of mine over coffee the other day. He's one of my biggest investors as well. And, you know, his, his sort of mythical number is bigger than mine because he's got wife and kids and bigger ecosystem to deal with. But it's, it's can we start working on things for their intellectual stimulation rather than for a need to plug a financial hole?
