- Max Levchin founded PayPal with Peter Thiel in 1999, and it grew with the help of Elon Musk and Reid Hoffman.
- PayPal went public and was sold to eBay in 2002 for $1.5 billion.
- He is now the CEO of Affirm, an online lending service.
- Levchin grew up in Ukraine in a family of scientists; he learned how to code using pen and paper.
When PayPal was sold to eBay in 2002, Max Levchin didn’t know what to do with himself. He had cofounded the company with Peter Thiel and built it into a Silicon Valley success with the help of Reid Hoffman and Elon Musk.
After the sale, all four left the company. But Levchin couldn't totally let go.
"I had the embarrassment factor of having our HR head, who was still there, take me aside and say, 'Hey, I just want to remind you: You quit, right?'" Levchin said in an interview on Business Insider's podcast, "Success! How I Did It."
On this episode, Levchin talks about his failures before PayPal and how he stumbled into a product that fit the market. He also really struggled to find himself after the acquisition, so much so that his girlfriend dumped him. He has since gone on to launch a bunch of startups — and his girlfriend got back together with him.
He now spends most of his time at Affirm, which offers small loans but doesn't charge any penalties or fees.
Listen to the episode:
- NBC News host Megyn Kelly
- Author and investor Tim Ferriss
- LinkedIn founder Reid Hoffman
- And a "Master Class" episode on leadership advice from our guests
Following is a transcript, which has been lightly edited for clarity.
Alyson Shontell: The story of Max Levchin starts in Kiev, Ukraine, where in the mid-1980s life was about to change. Levchin was 10 years old and his family was full of scientists. That gave him a strong interest in science, which led to a passion for coding. But it also meant his mother saw some early signs that something was very wrong.
Max Levchin: So her job was at, randomly enough, the National Institute of Food Hygiene. And she manned, or womaned, the giant spectrometer/radiation meter. And so she would test foods produced all over Ukraine for radioactive poisoning, which, of course, 99.9% of the time were not at all radioactively poisoned. Except some time in April of 1986 they started becoming a little bit more concerning. Even before we knew that Chernobyl had a nuclear explosion. Chernobyl is somewhere between 100 miles and 90 miles North of Kiev, so it's quite close.
As they figured out that the government was engaging in a cover-up, my parents and my grandmother basically shipped me and my younger brother to Crimea, which is the southernmost point of Ukraine — now no longer Ukraine but part of Russia — and I spent the next year and a half there.
When I came back, life began remaking itself. I went to a new school. But my mom, now her job was extremely important. She was constantly testing foods and there was all sorts of new data coming out. And so her research primary investigator told her, "Hey, you need to learn how to code, because writing down all these results by hand just isn't cutting it. We need to start storing data using computers."
And so I think I was 11 or 12 when I got back to Kiev. My mom said, "Hey, they gave me a computer at work. I need to learn how to program this thing and you're coming with me." And so my exposure to programming was actually instigated by my mother, who said, "This is gonna be a lot faster if the two of us learn in parallel, and then you help me and I'll help you." At some point, I actually talked my way into having one of these really garbage-y, Eastern bloc-manufactured computers home with me. And that was the pinnacle of my life, where I was, like, "Now I will do nothing. I'm just going to write code all day long on this East Germany-made equivalent of a Spectrum ZX, with a slightly nicer screen.
Shontell: You were writing code by hand for a time there, right? With pen and paper?
Levchin: Actually, before I was able to get my hands on this computer occasionally at home, I just couldn't get enough of it, so when I wasn't able to go hang out in her lab, I would just write code on a piece of paper.
Shontell: More incredibly, though, you would then plunk it into a computer and it seemed to work.
Levchin: Yeah, it actually did. I would debug it by hand, too.
Shontell: So you all moved to the US when you were a teenager, which I imagine was hard, and probably a bit shell-shocking. What was that like?
Levchin: I think I took it in stride. I made a very conscious decision to become an American with a capital A, as quickly as possible. So I think I was very busy trying to Americanize or assimilate and spend a lot less time trying to realize how difficult it is. There's plenty of cultural shocks where the idea of not buttoning your shirt all the way to the top was something I had to learn first day of school. Or learning what deodorant is for. Things like that.
Why Levchin moved to Silicon Valley after a few companies failed in Champaign, Ill.
Shontell: So you graduated from the University of Illinois and promptly head to Silicon Valley?
Levchin: I actually hung around campus for a little while longer, because one of my companies was failing and I didn't feel like having it fail in transit. I let it fail while stationary, but once it failed I moved to Silicon Valley. I was on company No. 3 or 4, depending on how you count, all of which had failed. And right between failure No. 4 and PayPal, I finally said, "This would be good opportunity to go to Silicon Valley, since that's where all my friends go, and sometimes their companies don't fail."
Shontell: How did you meet those people and what lured you there? This was late '90s, right?
Levchin: This is 1997, 1998. I kind of figured out that I wanted to code, and I hadn't really changed my plan since I was 12. By the time I was in college I just coded a lot more because I finally had my own computer and I could go to labs. I don't think I slept a lot. Certainly ate Snickers bars for lunch and dinner, and was coding in this lab all the time when these two guys stopped by and said, "Hey, what do you do here all day long, and night. You should come with us. We're gonna start a company." And we started a company, and it failed about a year later, in '95. It didn't work primarily because we were based in Champaign, Illinois, and it's very hard, and we're basically trying to mooch off university resources to do things, and that really came to a crashing halt eventually.
But, in that process, I became friends with these two guys. One of them is Luke Nosek, who was just, until very recently, a partner in Founders Fund, and since left to start his own fund. The other is Scott Banister, who has a whole bunch of interesting accomplishments to his name. So I've stayed friends with these guys forever, and the one thing they did after our first company failed, is they moved to Palo Alto, because they knew the lay of the land. I was still three years off the boat, and so I was, like, "Well, my grandma told me to graduate college, so I'm going go back to graduating college." They would send me emails and tell me, "Hey, Palo Alto is, one, warmer; two, has more venture capital; three: all the cool kids are here." I said, "Well, I'm going to graduate college, but as soon as that's done, I'm going to come join you guys." And so that's why and how I did that.
Shontell: So you head out. How do you get your footing?
Levchin: Yeah, I got there by car. I didn't really make any arrangements, so I just crashed on Scott's floor. And it was really hot in Palo Alto in 1998, which was when this was. And so I had a habit of hanging out at Stanford on campus during summer school because it was all air-conditioned. So I could sneak into a lecture, go in the back, pass out, and sleep a little.
And then, Luke, who had just started another company, which was funded by Peter Thiel, said, "Hey, Peter's giving a lecture at Stanford one of these days. You should go meet him because he's a really cool hedge-fund-manager-type guy, who is investing in startups." And so I had him in the back of my mind. I saw his name on the pinboard, wandered into a class that was taught by him, which turned out to be more like seminar with six people in the room. So it was a very small group of people. One: I couldn't sleep because it would be obvious, but two, he was actually pretty interesting. So I stayed awake and chatted him up afterwards.
In the inimitable Peter Thiel fashion, we basically spend about 20 minutes talking after his lecture, and he said, "Well, what are you doing in Silicon Valley?" I said, "I just got here two weeks ago. Probably gonna start a company." He said, "Oh, great. We should meet for breakfast." We met the next day. He said, "All right, so what companies are you thinking of starting?" I had two ideas that I was concurrently thinking about. I described No. 1., No. 2. He said, "No. 1 is better; you should do that." "OK." "I'd like to invest." It was less than 24 hours later. Peter was a committed investor in my new project.
And the next month or so, we were brainstorming. Obviously, I had started four companies prior. They all, to some degree, failed, largely because I had no idea what to do in terms of raising capital. So my original deal with Peter was, "Hey, I have to go raise money, it's great that you want to invest, but reality is, it's probably gonna need to be more 'Help me learn how to raise money.'" And so, for a time, he was still running his fund, and I was trying to put together a pitch deck, and I think within a day or two, he's like, "All right, you have no idea what you're doing with this stuff. Why don't I help you?" And so he started coming with me to the pitches. Over time, it became very clear that my role in these pitches was always to answer different technical questions, while Peter was painting the picture. And at some point, my agenda became, "Hey, he should be the CEO of this company. I shouldn't be the CEO. I should just go write the code, which is what I know and enjoy doing." And so, sometime by December of '98 is when I remember I called Peter up and said, "So, what do you think about this whole CEO idea?" He said, "I thought about it. OK." And "All right. Sounds great." And so we incorporated what became PayPal.
How PayPal became a hit payments after pivoting 6 times
Courtesy of Max Levchin
Shontell: So you guys get started. Was it a payment company right from the get-go?
Shontell: So you pivot into that?
Levchin: We pivoted six times by my count, but you can probably find more pivots if you wanted to. The original idea was actually the idea that I pitched Peter, which was, in retrospect, a brilliant idea before its time, or asinine, or both. But my thesis was that, at some point, mobile computers will be in everyone's pockets. This wasn't entirely from the moon, because PalmPilots had just launched a couple years prior, and everybody was toying around with one of those things. My theory was, very soon people in trucks will be taking notes about their cargo, and people in offices will be doing inventory, so this will be a device that has a place in enterprise.
What I was going to have a PhD in — which of course never materialized — was cryptography. And so my interest was in computer security. I really wanted to develop products in that space. I wanted to come over from being an academic to being an entrepreneur in computer security. So the pitch to Peter was, "Hey, all these PalmPilots are going to be very important in the workplace. This data is gonna be pretty sensitive. There's no security on these PalmPilots right now. You store a piece of data; it's a text file. Everybody can see it. If I steal your PalmPilot, I can log in; the passwords are trivial to break. So let's build a full framework of secure everything. Secure storage, secure communication. You can plug this thing into a serial port so you can transmit data. Somebody's gonna have to encrypt it end to end. So I had this expansive vision of security in a workplace on mobile devices. Of course, that is what we're all now expecting today from our iPhones and Android devices, but 20 years ago it was probably way too early. So, within a few months, Peter and I were essentially pretty clear that, while it's a cool idea, it's probably from too far in the future. And we started boiling down. So what do we have? I'd already recruited a couple of engineers from Illinois who I knew were all writing code all the time. Some of the things we were writing we weren't really exactly sure why, but we kept on building more and more sophisticated security infrastructure. Part of it involved something that Peter called "digital IOUs," where you could say, "I promise you $10," and I would digitally sign it. I think it was Reid who —
Shontell: Reid Hoffman, who was the cofounder of LinkedIn.
Levchin: Yeah, he was our second board member, I think. Scott was first; Reid was second. But Reid eventually became executive vice president of PayPal. He said, "Well, IOU is really cool, but how about invoices, so you can actually settle the invoices, and so you need a way to pay them, but then you can close the loop. You don't have to rely on some other channel to pay the IOU." I was not particularly excited about it, but then I thought it would be really interesting to integrate credit-card processing because I had never done it before. And so one thing led to another. I built a way of settling transactions from PalmPilot to PalmPilot using, on the web, you could log in and pay using your credit card with this haphazardly put together interface.
But in the process of having this demo live, I started noticing that people were transacting through it. And then, I got an email from someone saying, "Hey, do you have a logo? I need a logo, ideally scaled down so I can embed it in my eBay auction posting." And up until that point, I had a really peripheral understanding of how eBay worked and what it did. And so, I just looked it up and thought, "Oh, my God — this is like a den of illicit commerce. I need to block them from touching my product." So I actually spent a fair amount of time trying to push eBay users away from PayPal. At some point, Peter asked me, "What are you spending your time on?" I said, "There's this eBay user; they're just trying to use our product like crazy. They're like cockroaches; you try to block them off and they keep on coming in through a different entrance." He said, "I think that's what they call market pull. I think all these people trying to pay online, they don't have any better choice than your haphazardly put together demo." And so the last pivot of PayPal was pulled into its final shape by the eBay public.
Shontell: And so around 1999 your path crosses with Elon Musk. He had something called X.com, which merged with PayPal.
Levchin: The merger was consummated in 2000, but we knew of each other by '99, for sure. We didn't really realize that X was basically a direct competitor. Over time, it became very much an open race, and it was kind of a rivalry to the extreme. And then at some point, we realized that we're doing exactly the same thing, competing with each other as aggressively as we could. At some point, Elon and Peter and I met up and basically said, "We should probably consider merging companies given the fact that we're just gonna beat the crap out of each other in the market, and some third party is gonna come in and take it all away from us." And so, by May 2000, we merged.
How Levchin decided to take PayPal public then sell to eBay for $1.5 billion
Courtesy of Max Levchin
Shontell: So PayPal goes on to do great things. You guys eventually take it public and then sell it to eBay too. I think the price was something like $1.5 billion. You're in your 20s at this point, you've done a couple companies before, and finally, you're tasting real success. What was that process like of those two different types of exits?
Levchin: First of all, we decided to go public, not quite on a whim, but it was not a multiyear "When do we possibly get big enough to go public?" We were very focused on getting profitable. We were very focused on this march to profitability, or march to scale of payment, and then somewhere in that, we said, "Oh yeah, we're probably gonna go public at some point after." And that wasn't such a big deal at all. The business goals were much more important. As we started getting really close to going public, all kinds of crazy stuff started happening. We would get sued by patent trolls. Every other day you would find "We filed a lawsuit against you; you're infringing on this patent" in our fax machine over the weekend because it would get faxed in Friday night. And Monday morning, we're like, "One more lawsuit. Apparently we're infringing on a telephone-network patent that was rotary dial. How is that possible?"
So all this stuff was just a constant cacophony of things conspiring to keep us from being public. And so by the time we finally got there, the night before the last printing of the perspectives, half the company seemed to have moved to the printer's office. I slept on the floor of the printer's office and then was awakened by a lawyer's boot, who kicked me in the ribs, not very hard, but we got sued again. And the underwriter's counsel basically said, "I we have to reprint again; we don't think we can take you guys public. The market window is going close.” Whatever that really means. It was one of these bizarre moments where I had to run to some law office and the underwriters flew in their own lawyer, and I realized he really had no idea what he was talking about in a technical sense. And so I fired him in the middle of this conversation. It was extreme drama.
And finally we were allowed to go public, and it was this giant release. We opened and we closed, and we closed up, and it was a big deal. And then, the next week everybody was just very busy watching the price. The takeaway that I had was, "Oh my God, the run-up was so much better than being public. Why don't we go back to work? We were so hammering at it four days ago. Why is it OK now to just spend a lot of time staring at the price?” And we were all locked up for six months anyway. Anyway, so it was a huge run-up and, to me, a big downer afterwards.
Every time we'd get a bid from eBay, I would gather the team and basically say, "Hey, tell me how tired are you? I know we're all tired, I know we've all been working seven days a week, four years straight. Do you want to sell the company? Or do we fight another day?" And every time, the team was like, "We fight another day. We have plenty." After the IPO, I think it was six months in or something like that, it was another one of these meetings where I said, "All right, eBay is back. This is definitely, maybe the last time they're ever gonna bid. If you're tired to the point where you don't want to handle another fight. Another year of just beating each other up, maybe this is the right time to sell the company." And I didn't actually hear anyone say "Let's do it" but as I looked around the room, I was, like, "Wow, these people have been just dragged through a competitive mud over and over again. And they survived every time, but it's gonna get harder and harder." And so, to me, that was the point where I said, "I think we should take this offer seriously as opposed to all the other ones where I was sort of, like, ‘We can do so much better than this.’" And so, that was the beginning of the sale process.
Shontell: Wow. That's some radical transparency there, because most founders don't go to their teams, I don't think, and say, "How do you guys feel about this sale?"
Levchin: It wasn't the entire team, but it was basically my direct reports, and their direct reports, I think, so it was a pretty big group. But I really wanted to get the sense of commitment, because the competitive dynamic between us and X, and then us and eBay was pretty brutal. Payments in general is a very competitive space, and so it's always been.
How Levchin found himself again after "wandering through the wilderness" after leaving PayPal
Courtesy of Max Levchin
Shontell: And so you do go through with the deal, they acquire you, and I think you were the last founder to stick around, the last of the original gang. And then it seems like you left, but then felt a little bit lost after. I think you might be the only person in history who has quit and then returned to work for a couple weeks just to hang out with your old coworkers.
Levchin: That's not a very well known fact, but yes. I had the embarrassment factor of having our HR head, who was still there, take me aside and say, "Hey, I just want to remind you: You quit, right?" Like, "Yeah, yeah, but I kind of miss it." "You may be better off hanging out with your work friends outside of work, maybe you should hang out in nearby cafés instead of in the office." So I end up hanging out in the nearby cafés for a little while, and then I realized, "Maybe I should just take myself away from this for a little while." But for a time, my key card still works, why don't I just come back to work?
Shontell: But then why quit?
Levchin: It was definitely the time to go. It was very clear to me that eBay really wanted to make PayPal their own, and PayPal in many ways was a cult of personality built around the founding team. There were a lot of people in the early days that were outsized personalities, certainly Peter, and Luke, and I'd like to believe that I'm somewhere in that pantheon, but maybe not.
Shontell: So it is, I think, an emotional decision for any founder to step away from what they've created. And it sounds like it certainly was for you. And it sounds like your wife, you were dating at the time, and did she break up with you during this period?
Levchin: She broke up with me very briefly. I think, if you listen to her, she always had a plan to take me back once I got my head cleared out, but at the time it seemed terrible. But she basically said, "Look, you seem like a mess. You need to go spend a little time on your own," which, I think we were actually apart for about four and a half weeks, but it seemed like eternity.
Shontell: I'm glad you guys found your way back to each other, and you found a new mission. How did you find that? How did you figure out, "What do I do next? What do I do with myself next?"
Levchin: I didn't actually spend a lot of time figuring out what to do next. I really wanted to go back to work. I've basically always worked on stuff since my mom gave me that computer. And so this period of wandering through the wilderness was not healthy for me at all, and I dove in on a billings company called Slide, had a hand in a bunch of little companies, one of them called Yelp, and other companies that you have not heard of. It got me my now wife back, because she was like, "You seem very busy. Great! You're a human being again." But more to the point, I was engaged, and I had lots of interesting things and people and ideas going around me. And spend the next bunch of years, five or six years, I think, building this company called Slide, ultimately acquired by Google. And all throughout, I wasn't really focused on a depth of decision. I was just enjoying the fact that I had something that kept my brain fully engaged.
After Google acquired Slide, which was not really what I had planned for it to do at all, but there's a variety of good reasons for it — not all worth getting into — and the biggest one was I realized that I wasn't ultimately ever going to be thinking of Slide as my long-term future. It was not really ever the thing for me to do. After Google, my wife and I sat down, and she said, "Look, after PayPal, I've seen you. You're a wreck. You should not be left alone without a plan. So let's just make sure we don't go through that dip." And I said, "It sounds like a wonderful idea. What do you suggest?" She said, "You were so happy at PayPal. " We met the first year of PayPal, and so she had seen the entire growth, fall, and growth, and fall again. And she said, "You should just go back and look at financial instruments. All these ideas that you put on the shelf back then." And I was like, "No, no, no, no, I've done that." She's like, "Well, look what happened. You loved it a PayPal, you love security, you love serious problems, you want to solve things that matter."
And she's completely right. I love difficult, serious problems. I actually called up a bunch of my old PayPal friends and said, "Hey, what did we leave behind during the PayPal years that we should have gotten on top of and didn't and we were too busy doing PayPal stuff." And the best answer I got was from Nathan Gettings who had since gone on to cofound Palantir, and was my chief risk guy at PayPal. He said, "You know, one of the most amazing things that I always thought we should have done, and never did, was lending, because it's such a mess. FICO score is so old, and it's so inaccurate, and there are so many people who are excluded — immigrants and people who dropped out of school, and all these groups of people that are just completely misrepresented by it, and therefore are getting terrible terms. And if you look at the products, they've just been perverted into harvesting machines for fees, and no one really does lending honestly anymore. And you could get so much interesting data out of payment information, so they can do lending better."
And that conversation and a couple of other similar ones in the old PayPal crew really triggered me to go back to look at payments, and ultimately lending, and start Affirm. And Affirm originally was really a math exercise to see if we can do a better credit-score product. By the time we got really deep into how lending really works in the US, we took it from a cool math problem to a moral mission of fixing what became, short of certainly amoral and maybe worse industry of lending money to people who shouldn't be borrowing. Lending it on terms that keep them in debt. Lending them in ways that are not obvious to the borrower or not transparent. And so we can do it right with math is what Affirm's mission and point of view has evolved to.
Shontell: You glossed over Yelp, but you were the very first investor in Yelp. Which ended up actually being, of course, a huge and awesome deal. And you also sold a company to Google in there, which is something that not many people get to do. So I wanted to go back into those two life moments really quickly. First, talk to me about selling Slide to Google. I think it wasn't quite the exit that you had hoped for, like you said. It was about half the valuation when you sold it, even though it was over $200 million when you did. So, talk to me about figuring out, "This isn't what I'm supposed to be doing, this isn't working," and how do you then turn that, and sell it to Google?
Levchin: So it was actually one of these very fortuitous moments where Google was just realizing that Facebook completely outstripped them in the social realm. And they were looking around for a team of people, and a set of products. From what I can tell, they really did not have a fully big strategy, but they knew that they needed to catch up very quickly. I had a team of 128 people and the team was one of the better teams that I've assembled. And so, my commitment was primarily at that point, or solely to the team. And when Google came knocking saying, "Hey, you guys are a team full of people that really understand social media. We're trying to catch up. We want to bring you on to help us get into social." We were like, "This is kind of a marriage made in heaven. I have a team of people that really love social. I'm the only one who's kind of an imposter here. I will come and help and I will transition it in, but this is my way of helping everyone in this group of people."
Levchin built a healthy company culture by focusing on his values
Getty / Steve Jennings
Shontell: At all these places, you've built a really strong culture, you've gotten a group of really smart people and friends together, how do you build this culture up? It seems like you have some unique tactics. I know in PayPal there were some interesting interviewing tactics. Something around IQ, you had to have a certain IQ to work at PayPal. Do you still do those things?
Levchin: I certainly evolved my approach to building teams over the years. I try to learn from people whose company's culture I admire. And with Affirm, I'd realized that we're taking on an industry, with lending in particular, where morality and sense of right and wrong have given way to the sense of return of equity, which is the No. 1 metric that everybody cares about in lending.
And building a culture at Affirm, was front and center from the very, very beginning. At PayPal, the culture was incidental. It was more "Work really, really hard. Be really, really smart.” And it worked fine — the company was obviously successful, but probably could have done more. At Affirm, it was definitely something that day one, I said, "I'm going to write down my core values. I'm going to make sure that these values are in giant print on the wall of every office we ever have. And every year, I'm going to review them and make sure they're as crisp and as clean, and as memorable, so that every member to the team can recite them from memory, and know why we're here.” because if they can't, we have a real chance of falling into the same trap as what the industry did, where you dehumanize your customers and just think of them a source of income, as opposed to what credit was supposed to be: helping people invest in a better future. And so, at Affirm, we actually obsess over culture.
How Levchin measures his data and self-improvement
Shontell: I know that you use data in all sorts of parts of your life. And you have in the past, and I think maybe you still do, try to make your life and your health as efficient as possible. You are a big biker, you really watch what you eat. So what's your health routine like? And what have you learned from all the self-experimenting that you do to optimize?
Levchin: These days, having fairly demanding start-up career as a CEO, a family with two little kids, and a few other obligations in life, I do less experimenting, but I try to ride my bike every day. I try to be pretty healthy as an eater. But I basically find a routine that I like, and I just stick to it obsessively. If I skip a day, it's extremely uncomfortable. The No. 1 power in any behavior is in turning it into a default. So long as you make those defaults healthy, it's very easy. You can just exist in a fairly healthy universe. So long as your daily default is "Be on the bike," some days you'll miss because you're traveling or you're sick. But most of the time, you'll just get up, and get on a bike first thing in the morning, which is what I do.
Shontell: And so, you've had this long, great career, you figured out a lot about life and business, and everything along the way. What's the best advice you can give, looking back on your career, the things that you really did right, and the things that you wished you had learned sooner?
Levchin: My grandmother once told me that the only difference between somebody with a failed life versus somebody with two PhDs is perseverance. There's nothing else. And she really stressed that point. You just have to have enough grit to go through the parts where you want to quit and don't. So I think perseverance, grit, tenacity — you fill in your favorite word for that. I think that is the No. 1 success factor for entrepreneurs. And my No. 1 internal "Hey, get going already" motivational line to myself is "Don't be lazy. Just go do it."
And the other one I think I should have thought of 20 years ago, but I think I'm better at now — just take more risks. The younger you are, the easier it is to take risks. And I think once you get in the habit of taking risks, it becomes easier, then you just sort of know that it's OK. Failure isn't really that big a deal, and it's helpful to fail a few times early on in your career, because you know exactly how the bottom feels. But you get in the habit of not always failing, and that becomes the good default.
Shontell: Great. Well, Max, thank you so much for your time.
Levchin: Thank you.
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