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I started a new commerce company.
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I wanted to be the William Sonoma pet supplies.
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I put a million bucks my own money in I sold it for like a million and a half.
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So I made some money, not a lot.
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Um I invested or I started another e-commerce company. I started a travel site.
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Sold that for a little bit of money.
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money. I started a company called Red Envelope which went public on the NASDAQ in 2002 and because I was young and dumb, I kept investing and then I got in a war with the board and I did a proxy fight and I took over the board and put more of my money in and then 2008 came and there was a lot Charmin strike and a software
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malfunction at the warehouse where we sent 10,000 gifts to the wrong addresses over the holidays and then a Wells Fargo analyst who was like 14 decided the credit crisis was coming and pulled our line and my stock went from seven bucks a share to zero in about 11 days and when the company had declared chapter 11 and I lost you know, I lost pretty much everything. Do you remember how much money
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Do you remember how much money when you felt that tipping point where you did feel financially secure?
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Not like bulletproof where nothing will ever will happen, but do you remember the inflection point where you're like, okay this feels different than I've felt on the climb.
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I still don't I still haven't hit that point.
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I'm still very anxious about money.
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You know, I had and I like to be very open about money cuz I think that not talking about money is basically a decorum that is promoted by the incumbents and the wealthy such that you don't understand how much money wealthy people have to keep poor and middle class people under the illusion that oh you you should be paying 45% taxes while I'm paying 17.
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And I think I think it's important to be very I think it's helpful to be transparent and I talk about how many much money I've lost all my investments, how much money I've gained, my tax rates, etc.
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But you know, I'm I'm still I'm not obsessed with money.
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I think about it all the time.
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I'm trying to get a lot more. I'm I'm giving it away.
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I I five year from five years ago I decided I was going to give away every dollar I made in current income um cuz I want to start catching up to the non-philanthropic Scott for the first 45 years of his life, but I'm still trying to make a ton of money.
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I still feel financially very insecure.
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I still worry about a recession becoming a depression and I'm the guy who lost it again.
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I've lost it all a couple times and so I don't feel I'm at that point where I don't have financial anxiety.
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I do sleep with one eye open.
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You know, I sold my first company for 28 million bucks by the time I split it with my ex and my partner and taxes I ended up with a few million dollars.
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Red Envelope I got a few million there, but I always seem to figure out a way to lose it, but I was able to start again cuz I never had debt.
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I've always lived below my means but I would say the big win was probably selling L2 when I like that oh wow, I can buy a plane.
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Like that was not in my reach before.
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So that was kind of the big one.
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That was like all the moons aligned. the price? What did it sell for?
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200 or 300 million dollars?
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No, it sold for 158 million, but we'd only done one round of venture capital.
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So the you know, the common shareholders, you know, I was the largest equity owner.
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Um So the top you know, between me and the top six employees we probably owned 70% of it.
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Um so that was that you know, that was a lot of money for me.
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I'd never had that kind of money before.
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I'd always done well but I'd never had that kind of that kind of capital and then getting to invest that in the midst of a bull market. We sold in 2017.
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I've made more money investing actually than I've made from my small from my businesses.
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You know, the ability to create an army of capital even if it's only 50 bucks a month or 100 bucks a month, put it in a tax deferred or tax efficient vehicle, diversify it and then let time take over again see above you don't know how fast time is going to go.
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That's where I've built real wealth.
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This doesn't this doesn't make sense for Sean because Sean is not worried about money at all.
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He's got this thing that I like to call like good emotional health.
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He's very emotionally healthy.
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His his parents did did him well and he's talked to me about this.
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I sold my company two or three years ago and I made a fair bit. What did you make?
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I'm Sean I'm like I'm naked here. What did you make? Yeah. Let's go. Let's go Sam.
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You got to say He's hesitant.
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He's hesitant cuz he's worried people are listening. Okay, go ahead.
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Uh at the end of the the process I walked away with about 20 million dollars.
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That and how old are you?
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Uh I was about 30 I was 31 or 32.
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So you should be extraordinary you should be unless you really screw up, you should be much wealthier than I am by my age cuz to get that sort of capital feel shitty.
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I feel the same like I still like I felt awesome for a minute and then I felt shitty where I was like like when I see these world events right now when I saw like whatever happens every six months I'm like the world's going to end and I and I do like an I'm boring. Sean makes fun of me.
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I do 80/20 index and bonds.
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That's the That's exactly what you should be doing right now.
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I think so and I and then I own HubSpot stock still and then I own Airbnb stock.
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That's basically basically my portfolio and Sean makes fun of me.
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He's like, how are you feeling insecure?
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I'm like, dude, I'm broken. Like I'm broken.
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Like I it doesn't matter how much therapy I go to.
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I'm just a I'm a broke when it comes to money I have a scarcity mindset and I'm broken. Yeah, I'm the same way.
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And when you talk about how you're worth you know, 100 million plus and you don't feel secure and Sean said he's like what a little Like you know, like you talk about masculinity man up. You know what I mean?
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Like I and I have the same thing. I'm like I I can't. I'm weak.
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All right, if you like that clip, there's a full conversation with a lot more just like that. Just follow my finger. It is right here.