The Story of Scott’s Career

23:07It 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. That's what I was just going to say. It sounds like that was your longest commitment to any company. It was a very stressful time.

23:40About the time I had gotten divorced, which was financially very stressful. I lost everything in red envelope. And then the Great Recession came. And about the same time, my oldest son had the poor judgment to come marching out on my girlfriend. That was probably my most stressful. I've had a pretty charmed 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.

24:22And 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 Brown for? So I was living in San Francisco, and I always thought, I don't like it here.

25:00Everyone, 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, I've never enjoyed San Francisco. I think it's a beautiful city, but I've never wanted to live there.

25:30And I got to New York and Ed, the bars are open till like 4am 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 going to 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, Maveron, Howard Schultz's venture capital firm.

26:16I 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, BidShift. And I closed Room 12 because there was no leadership there.

26:54And I went to Gold Violin. And Gold Violin was basically products for seniors run by Connie Halkwist, who I had worked with at Profit. And Connie had kind of built Profit. Typically, at all these companies, I've started this 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 of profit, help me get it sold. And ultimately, we did sell it to Dentsu for about$28 million. 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.

27:23And I went to them when Brandfarm was, there was no more capital available for any e-commerce incubator. And I said, I will, if you cut your burn by 50%, I'll double the investment. 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 had some muscle memory. I was starting to get, I think, a little bit more mature from a business standpoint. The thing is, Brandfarm was around less than a year, and I see it as a victory because I failed, but I failed fast.

27:53and 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 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 the Third is failing fast. What you want to avoid is failing slowly. And then the sixth business was Firebrand Partners, which you started in 2005, which was an activist investment firm.

28:33Take 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 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 Pangaea 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.

29:08And 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 in the aughts, whatever you want to call it. but I was 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 at Red 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.

29:47Basically to kick people out. Yeah. Your job is to unlock value, which back then essentially meant go in 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 in the world. 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.

30:18The 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, blazed the 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.

30:50and but we ended up selling to Acer I think for like two dollars and fifty cents so turned 70 million into 90 million I struck a deal with a hedge fund to get 10 percent of the upside so I made I ended up making like a million bucks I remember thinking wow this is fun it foots 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 dollars 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 100 in about 14 months.

31:25The 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 was 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 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.

32:08and at NYU, the dean said, you either 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 got to 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 1 ,200 data points across digital, social, mobile, and e-commerce, and then would apply those 1 ,200 data points, currency conversion, Multiple languages, how many clicks to product, ease of checkout, customer service, and all this shit.

32:41Just measure everything. And I measured it for the 100 biggest luxury brands in the world and then issued a ranking. And I thought, this will be a center. I'll run the luxury and retail center at NYU, and I'll have credibility 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 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.

33:15And 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 or six hundred thousand dollars to my name which is a you know a lot of money by most people's standards but I said I'm going to 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.

33:57And 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, okay, 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.

34:28I 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, 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 katherine 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 and we moved to a recurring revenue model instead of charging consulting fees like profit we charged a recurring revenue model and said i'm just collect data on you png and then i'm gonna show up every once in a while or my team is, I'm going to tell you what Tide needs to do.

35:23And 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 own niches, right, which were more defensible. They were known for kind of dominating a niche.

35:56Two, 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 up front,$15 on the back end. They gave me like a 400-page indentured servitude contract that said, at any point in the future, if Martin Sorrell decides to sue you, he can for any reason.

36:34And 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 revenue.

37:09So I knew at the outset, I want to sell a company at an irrational multiple. We'll be right back.

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39:05We're back with Prof 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 it's called a way the luggage company and someone from rent the 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.

40:08I 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 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.

40:44And I was very focused on economic security. And I don't think you're going to 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. I didn't want to bank on. I know I'm not the latter, and 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.

41:19I 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 going to almost get there. And it's going to haunt me the rest of my life that I'm going to 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.

41:57It was just so meaningful. And the people around us 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. 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.

42:39That'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, journalists are writing stories about you replacing people on boards and fighting with Sequoia guys, and then 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. I was like, okay, I'm the guy who went to Davos and was on the cover of Inc.

43:24Magazine, but I can't buy my mom a house. You know, 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'm like, 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.

44:09But 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 it 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.

44:49And I mean, I'll give you an example. 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.

45:22Do 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.

45:54They just don't have that risk tolerance. 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, and 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 going to 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.

46:28And 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.

47:06Why 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.

47:37And 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 the time sheet 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 want to do next? I want to say EdTech startup. They invested. I got some other people to invest.

48:05And the idea was, again, kind of 80 % of an elite school elective 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 overhired 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.

48:45And then in 2020, you started Profit 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 investor is in town, I have to have dinner with him.

49:23There'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. 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 it 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.

50:01And 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 muscles that I didn't get a chance to stretch and talk about things that are important to me. And it's been lucrative.

50:38We'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.

51:15We 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. I'm not driving towards a nine-figure investment at the same time. 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 fun. I mean, you guys may not realize it. 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 want to talk about. I get to meet super interesting people.

51:55I 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 you know i used to get up some mornings and you know at l2 and a red envelope and a prop and think fuck this is going to 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 you know thursday night at 2 a.m when i'm trying to turn the chicken shit you and stavards have thrown over the wall with no mercy malice into chicken salad.

52:33Sometimes 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, 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 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.

53:17I 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 supportive of it. But no, you need to be crazy. You need to be able to work 60 hours, 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 list for who they want in a mate, and then they fall in love and they tear up their list.

53:53At 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 could write out a million scenarios. I guess some people grow up, they don't know they want to be a doctor their whole life. But yeah, I just ended up sitting here at the one hotel, having just spoken to Live nation heading to F1, knowing I'm going to 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 like so many, like, everything's a fucking shock.

54:34I 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. That question sort of overwhelms me. It's all like Ben. Shocking. In a good way. I'm also shocked at how much fucking vacation time you take, Ed.

55:16That'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.

55:38intern Drew Burrows is our technical director, and Catherine Dillon is our executive producer. Thank you for listening to Prof G 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 Aswath de Motoren, only on Prof G Markets.

56:08In kind reunion As the world turns And the dark flies In love

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