The Prof G Pod with Scott Galloway - Prof G Markets: The Story of Scott’s Career

Episode Date: May 26, 2025

Follow Prof G Markets: Apple Podcasts Spotify  Starting June 9th, we’ll be publishing a new episode every day of the week, exclusively on the Prof G Markets feed. Be sure to follow Prof G Markets if you haven’t already. For Memorial Day, we’re revisiting one of our favorite episodes where Scott shares the story of his entrepreneurial journey — from launching a video rental business in his 20s to building his latest venture, Prof G Media. He reflects on the lessons he learned, the surprises that shaped his path, and the most meaningful moments along the way. Subscribe to the Prof G Markets newsletter  Order "The Algebra of Wealth," out now Subscribe to No Mercy / No Malice Follow the podcast across socials @profgpod: Instagram Threads X Reddit Follow Scott on Instagram Follow Ed on Instagram and X Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Welcome to ProfG Markets. We are off for Memorial Day. We are taking one last chance to rest up before we go daily. Just a quick reminder, starting June 9th, we will be publishing new shows every day of the week, Monday through Friday. Remember it will be exclusively on the ProfG Markets feed, not the ProfG Pod feed, which has that turquoise icon. It'll be on the ProfG Markets feed. So if you haven't subscribed to that yet, type in ProfG Markets wherever you get your

podcasts and subscribe. That's where you will get the new daily show starting June 9th. For today, we are revisiting one of our favourite episodes where Scott and I discussed his career as an entrepreneur at length. We broke down the nine businesses he started from a video rental company in his 20s all the way to his latest firm, which is of course our very own ProfG Media. If you haven't heard this episode yet, you have missed the Scott Galloway origin story. So here it is, the story of Scott's career. Enjoy it.

And we will be back with a new episode of Profit.G Markets on Thursday. So let's start in 1990. You're living at your mom's house in California and you have an idea for a VHS delivery business. Tell us the story of Stress Busters. So right out of UCLA, I kind of got the brass ring. I got a job at Morgan Stanley by lying about my grades. And it was a two-year analyst program.

It was, I think I was the first analyst hired out of UCLA into the program. Great experience, attention to detail, worked really hard, but I was terrible at it and I hated it. And that's a, that's a blessing when you're in your twenties, you want to workshop kind of what you're good at. I was not good in investment banking. I also realized that I wasn't good at working at big companies that I was. People romanticize entrepreneurship. I went into entrepreneurship because I realized I didn't have the skills

to be successful at a big company. To be successful at a big company, you have to have. I thought every time people went into a conference room, they were talking about me. I couldn't handle all the little injustices you have to endure at a big company. I needed access to all the information. I needed to be in charge.

And so I've always told people when they come to me and ask about being an entrepreneur, I'm like, no, gotta work for a big corporation if you have access because you'll get rich slowly and on a risk-adjusted basis is the way to go. Anyways, left Morgan Stanley was at home, needed to do something. And I walked into the, my video store where I rented videos on VHS. And it was strange.

And I said, what's going on here? And they said, well, the FBI seized the store because they were money laundering and were having a clearance sale and they were selling VHS tapes of cousins and Turner and Hooch and Apollo 11, I think it was, whatever the big hits were, 1990, for five bucks instead of 20 bucks. So I called my friend, Lee Lotus, my closest friend who was also kind of in the midst of doing nothing,

and I said, I have a business idea, and I bought 220 of these videos for $1,100, and Stress Busters was born. Initially, it was home delivery of videos. We mimeographed or photocopied a bunch of stuff, put on doorsteps, and people would call us and say, send me Turner and Hooch, and we'd deliver it to them. And that was difficult, logistically complex,

not enough scale, so I thought, I saw these twin towers in Century City, and I thought, that's the key. And so I had to pay, I bought a Rubbermaid card, stacked it full of 120 videos, and paid off the security guards 20 bucks, and they let me into the offices, and I just went door to door to all the law firms, entertainment firms, and agencies, and accounting firms, and said, hi, we're stress busters, would anybody here like to rent videos?

And about, it felt like 80% of the time, it was probably 50% of the person in the reception would say you need to get out of here I'm calling security And they would literally chase me out of their office and occasionally they'd be like, oh, okay, you seem nice That's a great idea and I give the receptionist a free video or free video rentals and At one point they'd say stress busters is here and people would come to the front and pick their videos and you would hope The business model was you hope they forget to bring it back the next day so you could charge them more money. It was a shitty business, really hard, really stressful, humiliating at times, which is

a decent description of entrepreneurship. And we used to store the videos in my mom's storage locker in her garage. And one day I showed up and I think I forgot to lock it and all the videos were gone. And I'm like, oh, fuck, I don't know how I'm going to tell Lee. And my mom said, well, you know, I'm insured. My mom on a secretary salary bought insurance. And so I think it was Allstate basically said, you know, how many videos did you have? I think I had like 400 at that time.

And they said, we'll give you $8,000. And I'm like, oh my God, I called Lee and I said, our business is being acquired for $8,000 by all state insurance. And we high-fived each other and said, okay, let's apply to business school. And he applied to UCLA and got in. I applied to nine business schools because at a 2.27 GPA, I got into UCLA, Ian Cal, and I went to Cal chasing a woman I was in love with. Anyways, that was the end of Stress Busters. Did you think that Stress Busters was actually going to make you money?

I mean, it feels like such a stupid idea. I mean, I guess you could brand it as like a, some sort of early Netflix, but here's the thing though, Ed, no business before it starts. I would argue it makes sense. Otherwise it would already exist. And I didn't have a lot of skills. I didn't have a lot of capital and it just struck me as something that could be interesting. You know, I wasn't, I wasn't that strategic. I wasn't that well versed. I didn't have a lot of capital and it just struck me as something that could be interesting.

You know, I wasn't, I wasn't that strategic. I wasn't that well versed. I didn't have that many skills. I had, you know, I had $1,100 I could spend on VHS tapes. I had some gumption. The thing I took away from that is that it gave me a sense of resilience.

Being chased out of offices was humiliating and I would, I would recover and then I would go to the next office and go into that office. And I think that if you want to score above your weight class, professionally and romantically, you have to be willing to endure rejection and subject yourself to rejection. So then you go to business school and you have this professor, David Arka, who's this guru of brand strategy, and you have an idea for a consultancy.

Take us through the story of profit. So the myth is that people who go to business school know what they wanna do, and they're there just to get a springboard into what they wanna do. And the reality is the majority of people who go to business school are the elite and the aimless, and that is they don't know what they wanna do.

All they know is they don't wanna do what they were doing and they want to make more money and business school can give you a pivot into something and an abump in salary. Business school is remarkable when you think about it. You meet all the investment bankers in your first year class and they're like, I want out of investment banking and I think I'm going to go into consulting. You meet all the consultants and they're like,

I want out of consulting, I think I'm going to go into investment banking. You think at some point in our first year, we'd all meet and go, hey, it sucks over here. My second year, I took this class with David Ocker and he would talk about the importance of yellow and Caterpillar, heavy moving equipment that would been left in Germany and then it meant rebuilding an American democracy and prosperity and how, you know, Jiffy peanut butter was about maternal love. And I just thought, shit, this is what I want to do

the rest of my life. I just think this is so interesting, an interesting mix of quantitative and qualitative. And I approached David and I said, I'm going to start a business based on the principles that you teach here called profit. And I started in my second year. And for a student project in his class,

we're supposed to find a brand and do a brand strategy consulting engagement. I pitched Yamaha Motors, and they said we'd love it. And then I went back to them and said, you need a real engagement here. I'm going to go out and survey thousands of young people. They wanted to understand how to reinvigorate the

motorcycle market or the ATV market among youth. And I said, I'm going to, using new technology and this thing called a laptop, get thousands of surveys, do some analysis. And they said, fine, write us a proposal. And I said, but it's gonna cost some money. They said, fine. And I wrote a proposal, I called my friend at BCG and he sent me a proposal they had written.

And I basically copied the proposal for brand strategy engagement from, was it BCG or Bayon? I think it was BCG. But they charged a half a million dollars. And I said, okay, I'm not BCG, so I'll charge a quarter of a million dollars. And so I submitted this proposal to Yamaha and I didn't hear back.

And I thought, well, no shit. The guy was starting the business with Ian Chaplin, my business partner, said, well, no shit, Scott. You have no credibility and you just asked Yamaha Motors for a quarter of a million dollars. And I rolled up to my apartment in Rockridge, I was paying $280 a month and I opened the mailbox and there was a check for $125,000 from Yamaha Motors. I was pulled up to my apartment in Rockridge. I was paying $280 a month and I opened the mailbox and there was a check for $125,000 from Yamaha Motors. And I got a voicemail from Matt Takazawa, Yamaha saying,

Scott, sorry it's taken so long. I've been in Japan. We're excited about the project. You should have already received the first installment. And I remember when I saw that check, Ed, I remember thinking, did I just commit fraud? I said, hey, could I go to jail for this? And the lesson there is that nobody is really qualified to do anything they ever do. And that's what it means to be an entrepreneur.

And we worked our ass off. We did a great job for them and that kind of launched. So I launched Profit in my second year. And ultimately, David ended up joining our firm as vice chairman where he still serves. It's now, I think, a 500 500 person firm with offices all over the world. But profit was sort of my first born. I still feel very fond of it. And then eventually you hired a new CEO to come in and run it for you. How did that go down? Yeah, so I've always thought the thing about a services company is it's great in the sense it doesn't take a lot of capital.

It's an incredible test of your athletic skills. You have to be able to present, establish relationships, sell, manage people, analytics, qualitative. You know, it really is an interesting, it's got a lot of positives. The downsides are it's incredibly hard on your lifestyle. I remember commuting, we got our biggest client, I think our third year in business was Audi. And the CMO of Audi would call me and say, can you be in Ingolstadt tomorrow?

And the answer would have to be yes. So I would get on a plane with a team of people, another super talented guy, Sterling Lanier, also by this time, Lee Lotus had joined us. And we'd be on a plane in coach to fucking Munich on this 12 hour flight. And we would be in the back in the galley trying to come up with slides and ideas. And this was back when you had PowerPoint and I'd have to go, they didn't have

projection. I'd then have to go to Kinko's in Munich and print out this presentation. And we would be trying to turn chicken salad into chicken shit to present to the executive management team in a few hours as we were flying over the Atlantic. And then we'd be there a day, go out, have some beers and sausage, and then try and get sleep and get back on a plane back to San Francisco. And it was very hard.

I can't blame my failed first marriage totally on that, but it didn't help. And it was just very stressful. And I've always said, if you want to be in the services business, fine, but just keep in mind, you're always going to be someone else's bitch. They get to tell you when to show up. And I was good at it and I enjoyed it. It's a great way to get wealthy.

It's not usually a good way to get very, very, to get real economic security, because these firms generally don't get bought for a lot of money, because the assets go home in the elevator. But I decided I wanted out. And so I thought, okay, I'm going to bring in a CEO. I think this was 97 or 98. I'd gotten intoxicated with the internet and I took the first floor of profit, the basement, and I started internet companies. I thought I want to monetize the intellectual capital we're garnering helping other companies build internet sites or e-commerce sites. I want to take

some of the profits from profit and put it into these e-commerce ideas. So I kind of created a mini incubator in the basement. And then I would give equity in all of those companies to the brand strategists at profit based on them staying because the problem was all these firms were losing their best people to internet startups. So then in 1996, you start this company called Aardvark, which is like a online pet supplies company. Was that one of those basement brands that? Yeah, Aardvark, I'm crazy about my dog

and wherever I go to retail, it bifurcates into big box, very not aspirational retail, like a Walmart, like a Petco or PetSmart, or small mom and pop pet stores that smell funny. I'm like, there's no whim, no my pets. And so I thought I'm gonna do it online, start at Aardvark and AA for alphanumerics that would come up top in the AOL marketplace,

which was where all e-commerce was done back then. This was way back in the AOL marketplace, which was where all e-commerce was done back then. This was way back in the early days. And then we were offered $3 million for Aardvark and we took it and my partner, Ian Chaplin, who's much smarter than me, said, "'Let's take half in cash.'" And I said, "'No, it's the internet, it's going to the moon.'"

And he said, "'No, let's take half in cash.'" So effectively we got a million and a half cash, a million and a half in stock. 12 months later, I think it was pets.com. It was either pets.com or one of them. Went out of business, but we got a million and a half bucks. I'd invested half a million dollars.

So on an IRR basis to triple our money in 18 months, I think it's probably my most successful startup. Jason was saying something last night, which I found pretty funny, related to, you know, how you, the insurance situation with Stress Busters, where the insurance company pays you $8,000 and then same with this company. It's like you do have a knack for just sort of accidentally falling in piles of money. Well, yeah, I've also had some pretty serious fuck ups.

I mean, we're three into the nine, Ed. Wait, it's coming. We'll be right back. Support for the show comes from the Fundrise Flagship Fund. For decades, real estate has been a cornerstone of the world's largest portfolios, but it's also historically been complex, time-consuming, and expensive. But imagine if real estate investing was suddenly easy. All the benefits of owning real, tangible assets without the complexity and expense. That's the power of the Fundrise Flagship Real Estate Fund. Now you can invest in a $1.1 billion portfolio of real estate, starting with as little as $10.

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and a self-directed account are offered by Public Investing Inc., member FINRA, and SIPC. We're back with Profit.G Markets. So let's do the next one then, which is Red Envelope, but actually started as 9-1-1 Gifts. You started this in 1997. Take us through that. I went to this seminar, Kleiner Perkins and John Doar, who was kind of the god of the internet said that the internet's all about saving time and it's all men. And I thought, okay, how do I save men time on the internet? And I thought, men are terrible gift givers. I'll build a database driven merchandising platform where you type in someone's demographics, how much you wanna spend, the occasion,

and it spits back five or six great gift ideas. You click on, okay, it's a bridal shower. She's 25, I wanna spend 100 bucks. It comes back and says, here's a Nam Bay salad bowl. And I thought, okay, 911 gifts.com. 911 back then didn't mean 911. It meant emergency. And I got Sequoia capital involved.

There is a shit ton of money. How did you have the relationships with Sequoia to do that at that point? I had a shaved head and I was fearless and I was lived in the Bay area. I could get a meeting with anybody. And people knew you as the profit guy or like, I had run a successful strategy firm and was starting e-commerce companies and it was the 90s. And also I was born a white heterosexual male,

which meant I had unfair advantage. But if you were a graduate of the Haas school and you'd started a strategy firm and you had ideas and you had met with a lot of these people or they'd seen you in board meetings and you had ideas for the next big thing on the internet, I could raise a ton of capital. That was the easiest capital raising I've ever done. And about a year into it, we did a survey and we found out recipients hated the brand

because it meant that the giver was thinking about them last minute. I'm like, oh, fuck, I really fucked up here. Because the number one source of referrals and growth is recipients. They get a gift and they're like, I love it. And this was like, okay, you thought of me last minute. So I had to go back to my investors and say that the brand guy really screwed up here. We need to change the name and we changed the name to Red Envelope. A few years later, I sold Profit.

I doubled down. By the time I split it with my ex-wife, pay taxes, I had two or three million bucks proceeds from Profit. I poured all of it into Red Envelope. The market got difficult. Sequoia Capital, the guy who took my job as chairman, was a guy named Mike Moritz, who was arguably the most successful venture capitalist. It was under the impression he really understood retail and brand.

And he and I clashed. I was young, obnoxious, aggressive, didn't know the difference between being right and being effective, and it was just war. And we had just an incompetent CEO who, when we went public, we were the only public IPO of 2002, overestimated gross margins by a thousand basis points and had to announce that on an earnings call and we lost like 40 or 60% of our value.

I got into a war with Mike and Sequoia, it erupted in the New York Times. I handled it really poorly. It was just awful. And I kept putting more money in. I ultimately ran a proxy fight. I'm like, this firm is so poorly run. I wanted to get rid of Mike and get rid of the CEO

and on the way to the airport, I got a call. I forget who it was from saying, we're kicking you off the board and it was one of those moments where I was at the airport I was going back to New York I think I moved New York by that point where I drove up to Hertz and I got out of the car and I was like literally like I don't want to say paralyzed but I did know what to do I remember just sitting there or standing there outside of the car thinking, I literally just have no idea what to do here. Do I call a lawyer? Do I call other board members?

I just didn't know. I was frozen with kind of like indecision. I'd just been kicked off of the board of the company I started. So what I decided to do was get really fucking angry and went and raised, I think another 10 or 20 million bucks became the largest shareholder and began a three year process of kicking the rest of the board off and then taking control of the company again. And effectively I got control of the board, got back on the board just in time for the

credit crisis in 2007, 2008, we had an operational mishap at the warehouse where we had these guns that would spit out addresses. They spit out the wrong addresses on 10,000 boxes. So 10,000 gifts got sent to the wrong addresses. And at the same time, there was a longshoreman strike off the port of Long Beach. All our inventory got caught sitting or floating 10 miles off the Long Beach coast. And a credit analyst at Wells Fargo decided to cut our credit line because he recently predicted a credit crisis. And within like two weeks, we went from a stock price of seven to chapter 11, and I

lost everything in a matter of like two weeks. So people introduced me and they're like, Oh, Red Envelope. I remember them. I really liked them. It was a good concept, a good brand. I hear those two words in the same sentence and the lower part of my back starts to perspire and I feel

nauseous. It was just, I lost so much of my personal wealth. And it was so emotionally trying. And I've always said to people, if you fail and it happens fast, like 24 months or less, that's a blessing. The worst thing that's happened to me professionally was Red Envelope, because I failed really slowly. It took 10 years to play out.

10 years, so I was just gonna say, it sounds like that was your longest commitment to any company. It was a very stressful time about the time I had gotten divorced, which was financially very stressful. I lost everything in red envelope. And then, then the great recession came in about the same time. My oldest son had the poor judgment to come marching out of my girlfriend.

That was probably my most stressful. I've had a pretty charm life, but I was just so disappointed. I thought I've taken all this risk. I've taken a company public. I sold a successful strategy firm that I started at 26. I've had all of this quote unquote, you know, curb success or, you know, retail success, if you will, it looks like I've been really successful and I'm broke. And I mean, I wasn't broke, but I was pretty close to it.

And then when you're your age and you don't have money, it's disappointing, but it's not scary. When you have a kid, it's scary, because okay, it's no longer just about me. And I felt like, I remember thinking, Jesus Christ, it's one thing for me to fail myself, but now I'm failing this kid. Well, a lot of other things happened in the meantime.

So in two years after you started Red Envelope, you started this thing called Brand Farm that was in 1999, I believe. What was Brand Farm? So I was living in San Francisco and I always thought, I don't like it here. Everyone, I can't stand political extremism and it really bothers me. People who are extremists on the right really bother me. People who are extremists on the left mildly bother me. And I thought San Francisco was just, so I don't know, all these people who are washing you out

and are rapacious business people during the day, and then at night wanting to pretend they're saving the whales. And the fog and the weather, and I just thought, I just didn't want to be in San Francisco any longer. I've never enjoyed San Francisco and I just thought I just didn't want to be in San Francisco any longer. I've never enjoyed San Francisco. I think it's a beautiful city, but I've never wanted to live there. And I got to New York and Ed, the bars are open till like 4 a.m. in New York.

And I'm like, I have found my people. It's about money. It's about drinking. I just love, I just came to New York. I'm like, this is it. So I moved to New York and had some credibility, see above shaved head, and I raised $15 million on a PowerPoint presentation to start an e-commerce incubator called Brand Farm. Similar to kind of like an ICG or an idea labs, and I was gonna rent a lot of space, have one business development, engineering,

Corp Dev team, and I would punch out retail e-commerce concepts. And I got JP Morgan, Goldman Sachs, Barry Sternlicht, kind of this iconic real estate investor, AMB, Mavron, Howard Schulz's venture capital firm. I became close to the guy named Dan Levitan. It kind of ended up being sort of my rabbi. Nice man. Raised 15 million, started this e-commerce company incubator.

We launched three concepts within like six months, but then the dot bomb implosion happened Q1 of 2000. And there was just no capital available for an incubator, much less retail e-commerce concepts. So the whole thing was over. We still had some money. So I called the portfolio. We had three portfolio companies, Gold Violin,

Room 12, a travel concept, and a software company started by my former business partner, BitShift. And I closed Room 12, because there was no leadership there. And I went to Gold Violin, and Gold Violin was basically products for seniors, run by Connie Hawquist, who I had worked with at Profit. And Connie had kind of built Profit. Typically at all these companies I've started, there's one person that sort of built it and I get the

credit. Connie was that person at Profit. So I said, whatever you do next, I said to her, if you stay another two or three years at Profit, help me get it sold. And ultimately we did sell it to Dentsu for about 28 million bucks. I said, I'll fund your next venture. She came to me and said, I'm passionate about seniors. She started coming out, Gold Violin, multi-channel retailer. And I went to them when Brandfarm was, there was no more capital available for any commercial incubator. And I said, I will, if you cut your burn by 50%,

I'll double the investment and it'll give you two years to get through this nuclear winter. And I called room 12 down and closed Brandfarm down. And that was the right thing to do. I think at that point I'd sort of picked up on some stuff. I could, I sort of, I had some muscle memory. I was starting to get, I think, a little bit more mature from a business standpoint.

Thing is, Brand Farm was around less than a year, and I see it as a victory because I failed, but I failed fast. And then Gold Violin and Bid Shift both went on to exits. Not big exits, but exits, where the investors who ponied up in the B rounds in those companies actually made money. So I think a brand farm is sort of a, kind of marks the era, but I look at it fondly because a couple of companies survived,

and you know, if you're going to fail, fail fast. There's nothing better than success, but I don't want to say a close second, but definitely well ahead of a third is failing fast. What you want to avoid is failing slowly and then the sixth business was fire brand partners Which you started in 2005 which was an activist investment firm Take us through that. Yeah, so I felt like I had a feel for brand. I was starting to learn about the markets I had some time on my hands. I didn't know what to do I was meeting a lot of hedge fund people and I said by the way

What do you what do you do all day at this point in your career? I joined the faculty at NYU in 2002 and was teaching there, but mostly I would think about how I was going to go to some fabulous scene and try and drink a shit ton of alcohol to give me the confidence to meet strange women at a New York club at Lotus or Pangea or Double Seven. So I was in full arrested adolescence mode, like kind of mild alcoholism meets New York meets trying to figure it out. And I was having a great time.

It was a ton of fun other than the fact I was going broke. But that was a very interesting time, New York and the odds, whatever you wanna call it. But I felt like I understood brand, I understood the markets a little bit and I found some companies that I thought were undervalued. And then I had some credibility because I'd run this activist campaign,

it ran envelope, and even though it wasn't successful, people knew that I kind of knew how to, that I was crazy, but in a crazy good way. And a couple times shareholders would call me and say, we have a large stake here, we need sort of a tip of the spear. Do you want to co-invest and do an activist campaign?

Basically to kick people out. Yeah, your job is to unlock value, which back then essentially meant going and fire the CEO. I raised a bunch of money and bought 17% of Gateway Computer because I'm like, the cow pattern is powerful and we have distribution through Best Buy, we'll go in, the stock had gone from 70 bucks to $1.70. That was a pretty big company at the time, right?

Gateway was the second largest computer manufacturer at the time that we were selling three times as many computers as Apple, but our margins were like 8% and Apple's were 30, but anyways, raised a bunch of money, bought 17% of the company, went on the board. The chairman of the board was a guy named Rick Snyder who went on to be governor of Michigan and Ted Wade had just gotten off the board, and went in, blaze of glory, we need to sell this company for three bucks a share,

we all went, you know, get a 60% pop, stop the consensual hallucination. They were polite, they listened to my pitch, and they said, Scott, we engaged Goldman Sachs two years ago to try and sell this company. And that was a key learning, and that is when you come into a strange situation, you should assume that you're not as smart as you think and they're not as dumb as you'd hoped.

And, but we ended up selling to Acer, I think, for like $2.50. So turned 70 million into 90 million. I struck a deal with a hedge fund to get 10% of the upside. So I made, I ended up making like a million bucks. And I remember thinking, wow, this is fun. It fits to my personality because I'm angry and a bit of the upside. So I made, I ended up making like a million bucks. And I remember thinking, wow, this is fun. It fits to my personality because I'm angry and a bit of an asshole. So I enjoy going in and like stirring things up.

And the most iconic one was I raised $600 million to become the largest shareholder in the New York times company. Unfortunately, our timing wasn't great there. The great financial recession hit and I turned $600 million into a hundred and about 14 months. The stock did recover, but that was a very, very intense time. But that was sort of my kind of five-year adventure in activist investing with Firebrand Partners.

And then you started a new consulting firm called L2 in 2010. I think people know more about that one, but take us through the beginning there. So I had at this time, by now I was expecting my second kid, and I'd about that one, but take us through the beginning there. So I had at this time, by now I was expecting my second kid and I'd made some money, but it was lumpy, expensive to live in New York, two kids. And I thought, well, maybe I'll move to, you know, Chapel Hill or Charlottesville to a lower cost area,

just be full-time faculty, try and write, make a good living, cut my burn, and just live happily ever after. And at NYU, the dean said, you need the need to do research, peer-reviewed research, or write a book, or do something to establish yourself as a credible academic. I thought, okay, I'm not great at anything.

I gotta get back in the game. And I thought, I know I'll start a center on luxury. And I thought, well, the first thing I need to do is research. So I understood e-commerce. So I developed 1200 data points across digital, social, mobile, and e-commerce, and then would apply those 1200 data points, you know, currency conversion, multiple languages, how many clicks to product, ease of checkout, customer service, and all this shit, like just measure everything.

And I measured it for the a hundred biggest luxury brands in the world and then issued a ranking. And I thought this will be a center. I'll, I'll run the luxury and retail center at NYU and I'll have credibility as a, as an academic. And the head of the marketing department at the time came to me and said, we don't think of this as really like genuine academic peer reviewed research. I had no interest in writing academic research

for peer-reviewed academic journal. I was like, this is mental masturbation. It has no impact. I don't see anyone making any money here. That's not for me. So I said, I'll start a center. And the head of the department said, this isn't what we consider traditional academic research.

They said, but you can have the IP. So I spun it out and that was the birth of L2. We issued a ranking and I bet 30 or 40 of the 100 companies called me within 48 hours and said, who are you and why are you doing this? And right then I knew there was a company in this. And at that point, I think I'd had about four, $600,000 to my name, which is a lot of money

by most people's standards. But I said, I'm gonna take most of this money and start a business intelligence firm called L2 that benchmarks companies digital performance. And we went kind of category by category. First we did it in luxury, then we did it in retail, then we did it for CPG. It was called Luxury Lab initially and then Procter & Gamble called and said would you ever consider doing this for a CPG company? And I said yes and I hung up And I went to Catherine Dillon, who now runs this company,

and said, and Maureen Mullen, who really helped build L2. And I said, OK, we're changing the name of the company from Luxury Lab to L2, because we want to go after bigger fish and bigger companies. And that company, kind of all the moons lined up. We just had incredible human capital. The best time to start a company, I started in 2010, is in a recession,

because I got office space in New York for 34 bucks a square foot. I hired people at 20 bucks an hour. I think I hired Maureen for 20 bucks an hour. She had her consulting offer rescinded. She was a second year at Stern. I hired a bunch of students. She joined us, and I gave her 10% of the company.

And you know, the company ultimately got sold for $160 million, so she did really well. But we had this core group of just incredibly talented young women who really built this firm. And it was a combination of analytic rigor, and then Catherine bought sort of the creative juice. And that peanut butter and chocolate of kind of the academic rigor of academic research

coupled with the aesthetics of like an ad agency, the market just loved it. peanut butter and chocolate of kind of the academic rigor of academic research coupled with the aesthetics of like an ad agency, the market just loved it. And we moved to a recurring revenue model instead of charging consulting fees like profit. We charge a recurring revenue model and said, I'm just collect data on you P&G and then I'm going to show up every once in a while or my team is and going to tell you what what tide needs to do. And I had read this report from Deloitte. I thought this is my chance here. I'm going to tell you what Tide needs to do. And I had read this report from Deloitte. I thought, this is my chance here.

I'm running out of time. I need economic security. And I got this report from Deloitte that had evaluated exits of private companies. And they looked at the mean, the average mean of a analytics company or something was like two and a half times revenues. But there were some that were up six or eight times revenues.

And it analyzed the companies that had outsized returns in terms of valuation. And it said they had a few key components. They were, they own niches, right? Which were more defensible. They were known for kind of dominating a niche. Two, they had recurring revenue and three, they were international. And that kind of dictated our strategy around L2. I went to a recurring revenue.

We were going to own kind of luxury and retail as our niche and consumer brands. And I opened a London office almost right away. And ultimately, I think about seven years in, we raised some capital from General Catalyst. We were about to be sold for 30 million to WPP only four years into the business. They were going to give me 15 million upfront,

15 on the backend. They gave me like a 400 page indentured servitude contract that said at any point in the future Martin Searle decides to sue you, he can for any reason. And I'm like, I'm not signing this. And my friend Paul Sagan had just joined General Catalyst. I was calling him for advice and he said, don't sell the company.

I'm joining General Catalyst as a partner. This will be my first investment. They invested 17 million, I think, for a third of the company, or 12 million for a third of the company, I forget. And we invested a ton of money in technology such that we could expand the number of sectors we were in. And then 10 years in, in about, shit, I don't remember that, like 2016, 17, we sold to Gartner for, I think 160 million for eight times revenues. So I knew at the outset, I want to sell a company

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about your business needs. That's Vanta.com slash Vox. The Hot Honey McRisbee is so back at McDonald's. With juicy 100% Canadian-raised seasoned chicken, shredded lettuce, crispy jalapenos, and that completely craveable hot honey sauce, it's a sweet heat repeat you don't want to miss. Get your hot honey McCrispy today. Available for a limited time only at McDonald's. We're back with Proff G Markets. I've heard about the L2 days from Catherine and others, and it sounded super intense.

And it sounds like your approach to management was, for lack of a better word, also just intense. And, you know, you're intense now, but it sounds like the pressure was on. What was your management philosophy like and what was your mental health like at that point? I think my mental health was probably how most of America lives, and that is they're just really worried about money. My management philosophy, I was on a panel with I think the CEO of a way, is it called a way the luggage company and someone from Rent-A-Rent?

I forget who it was, two other unicorns. And they said, what's your management style? And one person was, well, it's about finding the right role. The other person is I want to model good behavior. And I said, my management style is I'm all fucking over everyone all the fucking time. And you know, the whole audience gasped because everyone wanted to hear about balance and

bringing out your inner child or whatever. I wanted people who like me wanted to build something great and build economic security and do great work. We were doing great work. There was no balance. We were working all the fucking time. I'm not exaggerating. I used to go into the office all day Saturday

and go in on Sunday for moral support of the people who showed up to the office on Sunday. And I'd walk into the office on Sunday and there'd be a dozen people in the office. We were all signed up to build something different and then you know hopefully recognize the upside and I was in a position to do it. It cost me a lot of time with my kids but they were very young and I was very focused on economic security and I don't think you're gonna build a company that gets sold for eight times

revenues in seven years without that kind of attitude, unless you're incredibly lucky or a genius. And I'm neither, you know, I didn't want to bank on, I know I'm not the latter and I didn't think I couldn't count on being the former. You know what, my fear, Ed, was I'd been blessed with so many opportunities. I'd been born in California at exactly the right time. Through no fault of my own, the world wanted me to win because of my sexual orientation, my race, and my gender.

I had all the advantages. I had all the wins in my back. I was talented. I had great certification from the University of California for no money. And I was right there about to get to the brass ring and I wanted to do the right things with it. I paid my people well, I've always wanted people to be economically successful, I wanted to give money away and I thought, fuck, I'm gonna almost get there and it's gonna haunt

me the rest of my life that I'm gonna be the guy that got there, was right there, and fell flat on his fucking face. So when we sold L2 and kind of rang the bell, if you will, it was like I had a year-long exhale. It was just so meaningful. And the people around us, you know, at L2, we all signed up for the same thing. And we liked each other. I gave away a lot of equity. I wanted people to do well. You know, it's a ton of fun to bring a 24-year-old into your office who has worked their ass off for two years and say, oh, your stake is worth $600,000 or your stake is worth $140,000. And these were kids that just weren't expecting it.

They didn't really understand equity. You know, that was hugely, and I've always been very crass about capitalism. I don't, I'm not here to build organizations that save the world. I'm here to build organizations that provide economic security for you and your family. That's what I've wanted to do. And we did it there.

That was your biggest exit. And I look back at your career and it's like, in terms of your reputation, you've had bigger wins. Like people, journalists are writing stories about you replacing people on boards and fighting with Sequoia guys. And then you were, you know, you went to the world economic forum and you were a leader of Tomorrow. Like you've had a lot of glitzy success, but that was the biggest financial success, it seems like. Was that more rewarding

than all of the reputation building in the past? Yeah, again, it was a fear. It was like, okay, I'm the guy who went to Davos and it was on the cover of Ink Magazine, but I can't buy my mom a house. A key algorithm to being happy in a capitalist society is to be rich but anonymous. I didn't want to be famous and struggling economically.

I don't, that was one of my fears. I moved to Florida because I can't afford the burn here to raise two boys in Manhattan. You know, the lifestyle I was used to, you have to make high six figures a million bucks a year. And I thought, I'm going to be that guy and it's going to haunt me because I'm naturally hard on myself.

I struggle with anger, I struggle with depression. I'm like, okay, I'm going to be the guy who was given every opportunity, worked really hard, incredible blessings, and didn't get there. But that was, since 2017, I've decided to give all the money I make away, because I'm now at a point, I don't believe in hoarding wealth, I'm now economically secure. But entrepreneurship has been,

I mean, it's been rewarding, but if I had to do again, I don't advise people to do it. It's on a risk-adjusted basis. If you have the skills to navigate a big company and put up with the bullshit, it's a better offering. The greatest wealth generator in history is the US corporation.

So I don't romanticize entrepreneurship. I think it is really difficult and really taxing on you personally and professionally. And I mean, I'll give you an example. The majority of people just aren't entrepreneurs. At L2, we were a year, we had been offered 30 million for the firm, the firm was just jamming. And we gave options to everybody.

And you could exercise your options, but you'd have to cut a check to the company. And that way, and then if you held onto the equity for more than a year, you'd get much more favorable tax treatment. You know how many people actually wrote a check to exercise their options such that they can, and this is a company that was doing really well, such that they could get capital gains in a year instead of paying 47% current income. Do you know how many people actually wrote a check of say like 60 or 80 people with options?

How many? Zero. I was willing to sign the front of checks, not the back of checks. I went to work 60 to 80 hours a week such that at the end of the month I could go home and tell my partner we needed to put 50 grand into the business. Very few people are willing to do that. And even when they're faced with the possibility of a bigger outcome, people are not willing to reach into their own pockets to fund a company. They just aren't. They're not used to that. They're just not wired that way.

They can't show up to work and put their own money to work. They just don't have that risk tolerance. That's not, you know, that's, that's what it means to be an entrepreneur and a founder and it creates sleepless nights. But the difference is the upside, if it works in only one out of seven small businesses do work. But then when they work, you get an irrational upside. But the closest thing I have to kids,

I would say the closest thing you're gonna have to kids before you actually have kids, is companies where you either start them or you're on the ground floor. Because this podcast looks, smells, and feels like you, Ed. This thing is the closest thing you have to a kid that's not your kid right now. And when these things do well, they surprise and delight you.

They are emotionally very rewarding, also emotionally very disappointing when they don't work. But you become irrationally fond of them. You become emotionally invested in them. And that's the key to building value, is you become irrationally passionate about the well-being of this inanimate thing called a company and you recognize that the other parents taking care of this kid are your co-workers and you become fond of them because they like you love this thing and

are trying to make it work. And your second to last company was Section. Why did you start Section? I actually don't know this. I think that higher education in the United States has become morally corrupt. I think we've adopted a luxury positioning where we artificially constrict freshman seats such that we can raise tuition faster than inflation, which has resulted in a transfer of wealth of a trillion and a half dollars

to middle-class households to university endowments, and I think it's morally corrupt. So I thought that starting an ed tech company that was sort of 80% of a graduate elective at a world-class business school for 10% of the price, that there'd be a big market for it. And initially I was right, and I raised a bunch of money from General Catalyst. I have everything I've done for the last 10 years,

General Catalyst is back. They're wonderful people. We don't even talk about valuation. I just trust them 100%. They made a bunch of money at L2 and some of the other stuff I've done. You don't discuss the valuation, they just gave you them 100%. They made a bunch of money at L2 and some of the other stuff I've done. You don't discuss the valuation,

they just gave you the timesheet and you were like, sounds good. Yeah, pretty much. I knew they'd be generous with me and I'd be generous with them. They said, what do you wanna do next? I wanna say, a tech startup. They invested, I got some other people to invest.

And the idea was again, kind of 80% of an elite school elected at 10% of the price, got off to a very strong start. COVID hits, people have a ton of time, company ran to 10 million in like no time flat. And once COVID ended, our revenues, we found ourselves, we'd over hired and our revenues were off 40, 50% kind of overnight. And we've gone, we went from zero to 120 employees

back to 30. And it's been, quite frankly, it's been very painful. But now we're growing again, we're focusing on AI and we're growing revenues again and we've right-sized the company. But yeah, it's been really, really difficult. And then in 2020 started Profit.ly Media. And when you talk about why you started it and what you wanted to do,

generally the theme that I've heard from you is that you just wanted it to be fun. You didn't want to go raise outside capital. Talk us through your approach to this company and why it's different to others. Well, Barry Rosenstein, the founder of Janet Capital, said something really profound to me. He said, the key to economic security, once you have it, is the following. Life is about three buckets professionally. There's things you have to do.

And Barry said, if my biggest investment is in town, I have to have dinner with them. There's things you want to do. He's like this rock and roll aficionado. He goes to see the cars be inducted into the Rock and Roll Hall of Fame. That's, you know, he wants to, and there's things you should do.

Well, I should go to my coworker's daughter's wedding. I should go to this fundraiser and get FaceTime with some other powerful people. He said, the thing about being economically secure is that you get this incredible luxury and that is you can eliminate the should bucket. And so now I'm like, okay, there's things I have to do, but there's things I want to do. And I want the want bucket to get

much bigger because I've spent a lot of my professional life doing things that were rewarding, but I didn't necessarily want to do. And I thought, okay, what do I want to do? I want to do stuff that's fun, that's creative, really trying to extend and damage and build back stronger some creative muscles, and also have a positive impact specifically around some of the issues I'm passionate about, struggling young men, income inequality, what I would describe as the war on the young. And the podcasts have been a ton of fun. Writing the newsletter has been a fantastic way to talk about relationships and express some creative,

creative muscles that I can get a chance to stretch and talk about things that are important to me. And it's been, it's been lucrative. We've built a really nice business. I don't think this business gets sold. I think it's the kind of business that can be very profitable and do well, and we can enter into really great,

lucrative long-term relationships with distribution partners. But basically we have our podcast revenue, we have our revenues from books, and then we get revenues from speaking and there's sort of a flywheel effect there. And this is hands down the most profitable business I've ever been involved with in terms of just right away, it started churning out capital, but we're sort of monetizing to be blunt, my brand in the marketplace, brought together some incredibly talented people. We pay, you may not feel this way, but I think we pay people exceptionally well,

do stuff we enjoy, but have fun and do something. You know, I'm not driving towards a nine-figure investment at the same time, or I realize young people want to build economic security. So we're trying to figure out a way to share more of the profits, if you will. But this is, this is fun. I mean, you guys may not realize that what we're doing here is I think incredibly, not only rewarding economically, but we have a big impact. It's fun. media is interesting. We get to talk about the issues we wanna talk about. I get to meet super interesting people.

I think some of our content resonates with people on a deeper level in terms of emotion, in terms of the relationships. So yeah, this is me rounding third. These are the salad days. This is incredibly rewarding. Nothing comes close in terms of, I used to get up some mornings at L2

and a red envelope and a prop and think, fuck, this is gonna be a hell of a day. And I don't discern between the weeks and the weekends any longer. I just love, I love what we do. Thursday night at 2 a.m. when I'm trying to turn the chicken shit you and Stavros have thrown over the wall

with no mercy malice into chicken salad, sometimes I get stressed out. But for the most part, everything we do, I like it. I think it has importance, I think it has relevance. You know, this is, these are the salad days, Ed. You're the tongs in the salad of the days of the dog. Is this the last one? I think so.

I want to, I want to really enjoy myself. I want to spend a ton of time with my kids and friends. I want to spend a lot of money. I want to give a lot of money away. And I don't think I have the tread on my tires to start another business. I just don't, I don't, I don't want to make that sort of sacrifice or commitment again. It takes a real toll on your relationships, on your mental and your physical health. I think it's a young person's game. I'll back people. You know, if you came to me and don't

get any ideas and said, or if anyone here came to me and said, I want to start a business, I would, you know, write them a modest check just to be, just to be supportive of it. But no, this is, you need to be crazy. You need to be able to work 60 to hour, 80 hours a week and just go so hard at something and I'm just not willing to make those trade-offs anymore. As you look back at your career, what has surprised you most? It's all been a surprise in the sense that I remember my grandmother telling me everyone has their lists for who they want and a mate, and then they fall in love and they tear up their list.

At 19, I thought I was going to be a pediatrician. At 22, I thought I was going to be an investment banker. At 34, I thought I was going to be an activist investor. And you just, you could write out a million scenarios. I guess some people, you know, grow up, they know they wanna be a doctor their whole life. But yeah, I just ended up, you know, sitting here at the one hotel, having just spoken to Live Nation, heading to F1,

knowing I'm gonna have to edit No Mercy No Mouse tonight after doing this podcast. You know, I wouldn't have guessed that I'd be divorced. I mean, I just, I just like so many like, everything's a fucking shock. I think the key is to put yourself in a position to be lucky because I think luck is perfectly over the long term, pretty symmetrical. And that is, yeah, I've had some bad luck, but I've also had some really

good luck. And you just want to put yourself in a position to be lucky. And how do you do that? You endure. Your company goes out of business, you don't give up, you go raise more money, and you keep trying. You get divorced, you don't give up, you go out and you try and meet another mate. It's all been, that question sort of overwhelms me. It's all like been It's all been, that question sort of overwhelms me. It's all like been shocking in a good way. I'm also shocked at how much fucking vacation time you take, Ed.

That's what really surprises me. Anyways, I'm sort of, the bottom line is, I'm very grateful. That would be the word I would use. This episode was produced by Claire Miller and engineered by Benjamin Spencer. Our associate producer is Alison Weiss, Mia Silverio is our research lead, Isabella Kintzel is our research associate, Dan Shalon is our intern, Drew Burrows is our technical director, and Catherine Dillon is our executive producer.

Thank you for listening to Profgy Markets from the Vox Media Podcast Network. If you liked what you heard, give us a follow and join us on Thursday for our conversation with the one and only Asswath Demodrin, only on ProfGMarkets. Life time You held me In kind Reunion You held me in kind reunion As the world turns

And the blood flies In love, love, love, love