Tech Brew Ride Home - (BNS) Susan Lyne Part 2

Episode Date: November 28, 2025

We're back again with Susan Lyne, to talk about running Martha Stewart's company when Martha went to prison, her startup career with Gilt Groupe, and her investing career with BBG Ventures. Learn more about your ad choices. Visit megaphone.fm/adchoices

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college PC. And by that, the only way she was going to put it behind her in the near term is to go and serve the five months in prison and five months of home arrest. So she did it. She sucked it up. And she went off to Alderson, West Virginia. And she was a model prisoner. She made a lot of good contacts down there.

She became a fan of and grew up. new fans while she was in prison. And she came out five months later, Rarin to go. She had the ankle bracelet on, but we started doing dinners probably two or three times a week for advertisers up at her house in Bedford so that she could start to kind of resell the company. If you are watching the video of this conversation, you might realize that Susan and I look a little bit different. I don't know if I left this in the edit or not, but we ran over time in the first half of our conversation. Susan was kind enough to come back to finish what is one of the most amazing careers I've ever had the privilege to interrogate. Susan, thanks for coming back.

Very happy to be here. We were leaving off talking about when you were Leco at ABC, despite the fact that the slate of shows that you had helped Shepard were huge hits and kicked off what I called the beginning of the Golden Age of Television. We were talking about... Well, not the Golden Age of Television, but maybe a more golden age at A.C. The modern golden age. But what we were talking about specifically was this idea of the Internet is coming in and changing how fandom works and how creators of media

have to engage with fans. I'm curious if you were producing shows, movies, whatever, today, how would you feel about that fact that you have to engage with the audience in a way that perhaps you didn't in the old days? Do you feel like it's a better era or for creators, is it more complicated? Well, it's definitely more complicated, but I think that there's also no question that people have a deeper connection to the shows that they love and a deeper connection to characters. And not just for new shows, but old shows, too. You know, this has enabled a lot of series to either have a second or third bite at the apple or to just continue to be. loved by millions of people. So in that sense, I think it's great. And I also think that there's such value in getting immediate feedback. It doesn't mean that you take all of it instantly,

but there's just a huge advantage when you understand. and what's playing and what's not. You know, you get that in a live theater. You don't get that when people are watching on a screen someplace. Well, now you do because the comment, the Reddit boards are immediate. Yeah.

Okay, so you were Lego from ABC. Can you just speak briefly for people that it's, when you have a career setback and a public career setback, we should say. What did you learn about picking up the pieces and, hey, I'm going to move on and do something else? Yeah. You know, when I called my husband to tell him what had happened, and he was back in New York, he said, after listening to me and sympathizing, he said, hey, you've got two days to really wallow in this.

and then I'm coming out and we're going to go to this book festival that was taking place in L.A. And then you're going to come back to New York. And you've got to look at this as a huge opportunity to kind of reset and think about what you want to do next. He was always a glass half full person. And I am too, to be honest. So as crushing as it was, I did not. spend a ton of time in wo-me phase. I did, as he said, spend a couple of days being really pissed off and very sad. But at the end of the day, I was relatively young. I was healthy.

I knew I had learned enough about different work streams and aspects of culture, and that now I got to rethink it and see where I could apply my skills next. So the lily pad you settle on is Martha Stewart Living Omnamedia, which you're on the board first, I believe, and then you become the CEO later that you're up. Tell me the story of going there. So the first thing I'd say is I took the summer off, and I had not taken the summer off since I was in high school.

So that was great. My kids were in high school and middle school, and it was for a period of time, it was really fun for them to have me home. I think by the time I went back to work, they were very happy I was going back to work. I think my older daughter was terrified that I was going to. become one of those mothers who hung around school. But by October, so immediately, I went on to the board of the Martha Stewart Company, then known as Martha Stewart Living Omnamedia. I knew Martha a bit. Like you know, a lot of people in New York City, you know, you see them occasionally and

say hi how are you but I really admired what she had built and I admired it significantly more after I went on to the board I'm not sure people realize how unique that company was in terms of the way it was organized and how they operated but she had a very unique idea I think that that covering living would allow her to create a lot of evergreen content. And so she hired, instead of hiring editors and copy editors and the kind of typical content company set up, she hired people who had expertise in certain areas. So she had a large food team. She had an entertaining team.

She had a weddings team. She had a crafts team. She had a holidays team. She had a home decorating team. They were incredibly gifted people who loved producing things. And at her story meetings, it was not editors who pitched what was going to go into the magazine three months from now, it was these sector experts who came up with projects and those became the stories that filled out issues of Martha Stewart Living. And every single one

of those stories would then become part of the law. library that they could tap into to create products, to create books, to create one-off issues, and ultimately to create the fantastic line that they did for Kmart. So it was a virtuous circle, right, but all based on her instincts about what American readers, wanted to see and wanted to learn. She's a teacher at her core. Let me point out something too, though, that this is a, I mean, Martha wasn't the first to do this, but it was a pioneering time in the sense that an entire industry slash company built around a personality, built around what you would call an influencer or whatever. So I'm thinking of the Kardashians. Right. Goop, even what Mr. Beast does.

So you were doing a lot of experiments at this time, right, with new partnerships and digital and stuff. And so what was that a – what did you learn about, like, crafting sort of what a modern media company is around a person? So what I would say is I took this job when Martha was going off to prison. Right. I was going to get there, but yes, yes. Let's set the time frame. Yes. She had built this incredible company.

she had used both the Martha Stewart Living, which was the anchor publication, which she had originally done as a co-venture with Time, Inc. She bought it back and then combined that with an extraordinary deal at Kmart that allowed her to create products in all these different arenas where she produced content, kitchen, home decorating, tabletop, entertaining, holidays, all of it.

If you went into a Kmart in those early days, the product was extraordinary. It was priced for mass market. And it really changed the way people thought about what was possible to produce and to sell to every American instead of to just people who had the money to outfit their house as well. Then she was indicted. Interestingly, James Comey was the prosecutor in that case.

She was indicted for insider trading, which she had absolutely not done. But she got caught up in the case against Sam Waxel and Imclone. She had been a friend of Waxil's. She had bought stock. And she called her a broker one day, or he called her. And the message was, hey, looks like the Waxel family is actually selling pretty big. chunks of stock. And she said, do you know why? And he said, I have no idea. And she said, let's sell. So it was not that she had been given a heads up. What was actually happening is that he knew that

the big drug that they were going to market with was not going to be approved in the near term. It was ultimately, but this freshed the market for M-Clone for a period of time. And Sam was indicted for having tipped off his father and daughter. They both sold stock, and Martha got caught up in it. And the case, they actually dropped the insider trading case pretty early, but it was her sort of cover-up or not wanting to look like she had done something wrong that ended up being her downfall here. Now, if she had been another person,

she probably would have appealed, and I think she had a really good case to potentially overturn this. But her company was in free fall, not because customers left. Actually, quite the contrary. People were buying more product at Kmart, We were even seeing subscribers to the magazine subscribing for two years instead of one year.

So there was a little bit of, I think she got a raw deal and I'm going to support her, but advertisers fled. And the company went from being highly profitable to being unprofitable and churning through cash. So advertisers were very clear. that they were not going to come back until this was behind her. And by that, the only way she was going to put it behind her in the near term is to go and serve the five months in prison and five months of home arrest. So she did it.

She sucked it up and she went off to Alderson, West Virginia. And she was a model prisoner. She made a lot of good contacts down there. She became a fan of and grew new fans while she was in prison. And she came out five months later, rare and to go. She had the ankle bracelet on, but we started doing dinners probably two or three times a week for advertisers up at her house in Bedford so that she could start to kind of resell the company. Ready to soundtrack your summer? With Red Bull Summer All Day Play, you choose a playlist that fits your summer vibe the best.

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The next thing you know, it's a thing. Canva, the thing that makes anything a thing. There were several things we had to deal with at the same time. One was that Kmart had been sold to Eddie Lampert, who was not going to make as good a deal with her next time round. And she had... had been dropped by her former television network, CBS. So we made a new deal this time for a live morning show. So instead of taped half hour, she was going to do a live hour of television every morning,

something she had never done. Honestly, I think that the combination of prison and doing live television set her up for what has been a... huge, I would say third act for her. She is very much an influencer now. She's got something like six million followers on Instagram, TikTok. She's got multiple accounts on on Instagram. She's beloved. She has a very diverse audience at this point. She made a bunch of friends who were not like her old Bedford friends by any means. And Snoop being one of them, they're a fantastic pair together.

And she's created a great, great business that is now really her, not the old company. But some of the pieces that went into that transformation, were the live television show. And instead of resigning with Kmart, we signed probably a half dozen maybe more deals with different retailers at different price points so that we could sort of make up that bundle that used to be the Kmart revenue. And it was challenging.

There's no question about it. There was definitely a rebuilding period. I was there for four years. I learned a ton from her. Did she sometimes butted heads? I was going to say, did she give you any specific orders, maybe when she's going to prison or whatever, like, hey, this is crisis management,

keep the brand to float. Like, what was your remit to, like, sort of stabilize the brand while this is happening? So her biggest note was, don't settle. Don't think that you should sign off on anything that isn't fantastic. We can't let our standards down during this period of time. So when I would go visit her at Alderson and I went probably every three weeks while she was in prison.

And she wasn't allowed to ask me about the business. And I wasn't allowed to kind of tell her how the business was doing. But we could have conversations about things I'd seen and things I had done, all in a very public room where prisoners were meeting their families. And I remember on one occasion having told her that I'd seen the, the prototypes for a new betting line, higher-end betting line. And I told her they looked great. And she said, no, would you buy them?

Do you covet them? And it's that, both attention to detail and demand that things be excellent, that I think both made people crazy, but also were really. really the core of why she built such an extraordinary brand. I'm not entirely sure of the chronology, but around this time your husband passes. I give you the opportunity to say anything about that that you want, but also if there is any sort of learnings about navigating personal crises while being a leader. Yeah.

he got pancreatic cancer, which is a horrible disease and very fast, I will say. It was only six months between, six and a half months between the time he was diagnosed and the time he died. And the first thing I'll say is that Martha was extraordinary. She, you know, was clear about the fact that I should take whatever time I needed. And I realized two things. One, all my daughters and stepdaughters all came home. And it was a terrible period of time, but it was also extraordinary. I think all of them felt like they really had time with their father.

to talk and to not leave things unsaid. And that is a gift. And I realize that with friends who've lost either spouses or parents very suddenly and felt like, oh my God, what was the last conversation I had with them? But that was not the case here. And work for me became the one place in my life where I felt like I actually had control. So George did not want me to stop working. He wanted me to come home every day and tell him what had happened. So one of his nephews moved in with us and became a kind of homemade during that period of time and stayed another couple of years afterwards.

And we had a full household, and we had dinner every night around a big table. And one time a week, I would go to the hospital with him, and we would do chemo overnight, and I would stay with him, and we would sleep there. but he wanted as much normalcy in his life during that period of time as he could possibly have. So I would not wish it on anyone, but he was amazing and I won't spend a lot of time on it, but he was an extraordinary person. I fell in love with him for a reason. He was an adventurer, and he always felt that every day was a gift and not something to be expected. He was a reporter and a producer for 60 minutes, and he wrote Charlie Wilson's War,

which was published a couple of years before he got pancreatic cancer. He did not live to see the movie. movie made, but he did live to see Mike Nichols hired to direct it, and he knew it was going to happen. So, you know, I think he felt he had lived, and that's absolutely true. He was, he had friends all over the world, and especially all over the Middle East, where he did a lot of reporting. and he is missed by so many people. Sometimes you don't realize how connected you are until too late. I think too late for him to see just how many people reached out.

I have volumes of letters from people I've never met about how important George was. their lives. And I know my daughters feel the same way. I do too. Big gift. In 2008, you go to guilt group, a pioneering flash sale e-commerce. But I want to point out that, you know, you've worked in studios, you've worked in magazines, and you, with Martha Stewart, it's an existing company. This is your first time working with what is essentially a startup, right? Well, not exactly, but certainly a tech-enabled startup. But Premier was a startup. Oh, that's true. That's true. We had five full-time staffers and a bunch of freelancers for the first issue, and it grew with the magazine. But this was the first time that that I was at a high-growth startup, and that is a very different animal.

Well, tell me the differences. What did you learn about? Like a hyper-growth company versus, yeah. I will say it was a cultural shift for me. When I was at Martha, I had an office at the Starrett building, and I had an office on 40, I think it was 44th Street. but overlooking Brian Park where you had to go through my assistance office in order to get into my office. Now I'm at Gilt.

I'm sitting at tables like this, right, where, you know, it's just a whole lot of people cheap to general. Yeah, yeah, yeah. And no one thinking twice about the phone call they're making or. who can overhear it. And I was in my 50s, so definitely a culture shift for me. But really exciting. I mean, it was every single day was a learning experience. Gilt was imagined by Kevin Ryan, who had seen a similar model used in Europe, in France.

and he thought that something like that could really work here. And the whole concept was, can we simulate the excitement and the conversion that takes place at a sample sale, right? Where you have to have an invitation to get in. It's a great brand, amazing prices. and you are fighting other people in order to get access to this stuff, right? It can go very fast. Someone can literally take it right out of your hands.

And early guilt was very similar. We claimed a time period. Noon every day is when the new sales launched. The brands were extraordinary. You could get the most amazing deals of any place on. the internet. By the way, I was a heavy user. I love the guilt. Can I tell you it is very rare that I meet someone who was alive and at least 20 when guilt launched, who does not say they were a huge guilt user. People are passionate about it. And I mean, I still have a lot of stuff that I

bought on guilt that I still wear today. So, It struck a nerve. People looked, reached out to find out how they could get an invitation. It was actually pretty easy to get an invitation. And after a certain point, we, we let go of that invitation concept, and you just had to register in order to be able to buy. But three great early engineers, including Mike Brzeck, who was an amazing CTO and built large parts of that site, literally, as it was live.

And it grew so fast that it became clear pretty quickly. It was built on Ruby, which was great for the early days, but ultimately it had to be rebuilt on a more stable platform. We started with check-in and then went to add to cart. And literally it was being rebuilt as people were outgrowing each of these different parts of the process. And barely, barely making it in many instances. In fact, the first Christian Lubutan sale we had, which are the shoes with the red soles on them that are extremely expensive. And I think we had 1,200 pairs of shoes maybe to sell that day. And like tens of thousands of people who were trying to put them into their carts at the same time.

And it essentially broke the site. But that would happen occasionally as the members, was growing so fast. Daily users were growing incredibly fast and the sales were growing incredibly fast. So for a period of time, it was just incredibly fun. I'm going to squeeze something else in before we get to BBG, but was being at Gilt the best education for you in terms of how you invest now in understanding what founders of the earliest stage companies go through? I will say it was incredibly valuable for a number of reasons. Guilt became a kind of clubhouse for a lot of young women founders at the time.

I met a ton of young women who were building companies. This was 2008 that I joined. So it's really the dawn of the mobile era. It was the year the App Store launched. And so all of a sudden, if you had an idea, you could actually launch an app and see if you could get traction. and a lot of women were doing that who could not raise capital, right? So it was a way to test and see if you maybe had product market fit

without being able to raise an institutional round. And remember, this was still when the VC world was even more homogeneic than it is now, significantly more so. So a lot of women would go in and pitch. an idea that was really imagined for a female customer and would get blank stairs and essentially show me, right? Not, hey, I get this. I'm going to give you some early capital. So for me, it was a combination of meeting a lot of women who were building companies. and I started breakfast for female founders during that period of time.

So I think the first one had eight founders and some more senior people who I thought could be helpful to them. And within six or seven months, it was like a hundred founders who would come to these breakfasts. So there was an early and growing community of women who were who were, building companies and that I became an angel investor in many and an advisor to some as well. So it was a combination of what I saw at guilt and what I saw in this burgeoning ecosystem. Own it all. Pay off your home, travel for life, drive a Ferrari. In celebration of the world premiere of the Monopoly Big Board Buckslot Machine by Aristocrat Gaming, Yamava Resort and Casino at San Manuel is giving one person.

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Let me ask you a delicate question, which is you're looking at, I'm assuming you're seeing that this opportunity to go at seed for women-led but also underrepresented, what you call polycultural founders from day one. When you go to raise from LPs and you say whatever year this would be, no, our thesis is this. This is a systematically overlooked opportunity. What is the response? Like, was that a difficult raise that first? fund? So the first thing I'd say is that we didn't raise an institutional round until 2019. We actually launched my partner, who was 30 years my junior, worked with me at AOL, and we actually convinced the then CEO of AOL, Tim Armstrong, to put up balance sheet money to see if we could

find good deals, could get into good deals, could, was this possible? You know, was this thesis that a broader ecosystem of founders could build for many consumers who felt underserved? So we were initially very much a consumer fund. It was a $10 million fund. We put up anywhere from $100 to maybe $250,000,000 initially. And there were a lot of great companies in that mix. Companies like the Wing and Hopskip Drive and Spring Health later, lots of companies and founders who've gone on to do great things.

but ultimately AOL was sold to Verizon. Verizon had a different point of view on kind of where the world was going, and they were very supportive, but it was the right time for us to see if we could actually spin out and raise an institutional fund, and that was 2019. So I would say the first fund, And there were enough people by then who understood that the world was changing and that tech founders could come from a lot of different places, not just from Silicon Valley and from Stanford or UC Berkeley. and so we were able to raise a $50 million first fund.

And then three, three and a half years later, a $60 million second fund. I will also say the LP base has changed some too. Definitely still see all the same pension funds, endowments who, love to get into the sequoias and the NEAs of the world. But an increasing number who are also looking for emerging managers who are doing something interesting and who may have a point of view and access to a founder that is different. Let me ask you an inside baseball question

because I invested the precedence seed level. level two. So the obvious question for anyone that invested that stage is how do you evaluate founders? Like, what are the signals that you're looking for? Is it market insight? Is it like, well, this is just a good person that's going to make anything work? Is it velocity of what's happening already? What do you look for? You know, we talk internally about both lived and learned experience. So the founders we like best are founders who, have some unique insight into either the customer that they are going after or the sector that they are going after. And that can often come from the way they grew up, their parents,

their unique community. And then the learned experience. can come from a combination of things. You know, it can be having worked in dealmaking at some financial institution, or it can be that they have deep health care roots and understand what's missing. But it's that combination. It's who are you as a human being and what's the unique insight you have to have or you have into an unmet need. And then do you have the grit and the,

the sector expertise in order to make it work? BBG is New York City-based, right? I'm not saying you only exclusively invest in New York City startups. No, we are New York City-based. What makes New York City-based? unique as a startup slash tech community? I think one of the things is that so many industries called New York City Home, so there's a whole lot of people here who have deep understanding of some sector so that when the time comes

to begin building for the application layer of mobile or now AI, you know, you know, have a lot of people who really understand what's possible, what people need, how to create something unique in that particular sector. I think that the foundational talent often comes from either Boston or the valley, but the application layer, New York City is great. Finally, and kind of dealer's choice on this one, what are you most excited about investing in now? I think we've gone an hour and a half and we just mentioned AI. I don't know. That could be the answer.

But also, even if it's not investing, like, what are you most excited about today professionally? Well, there's no question that AI has just transformed everything. Look, I felt this way when I first got into this world because mobile was changing everything, right? It was one of those moments where you thought, oh, my God, this literally is going to change the way we do everything from communicate to buy to discover, right? you had a store in your pocket for the first time. And with AI, I think, I honestly believe that every major consumer area, you know, think about the dominant players in job hunting, indeed, monster, travel, Expedia, house hunting, Zillow, all of these big consumer platforms are 20, 25 years old.

And while they will continue to be able to spend at a level that keeps them somewhere in that market, there's no way they're going to be able to create the kind of personalized, even agentic experience. that I think is now going to be possible. And that's exciting. That means that there's going to be a huge amount of turnover in companies, and certainly in the way we do things, right? You see that, I'm sure. We use AI for a lot inside our company.

Like everybody else, we're experimenting with it. all the time. And every founder we meet with, or let's say 75% of the founders we meet with, are building something new that would not have been possible three years ago. Susan, I said this to you offline, so I'm going to say it online as we end here, which is that I've done probably 250 of these style interviews in my podcasting career. I have never encountered someone who had such a varied career that was just so goddamn interesting that I was like, we need to give this time. So I so much appreciate you coming on and remembering all that for us.

Twice, by the way. Yeah, I really appreciate you giving me the time. You know, I've been working for 50 years now. And I say that because I think a lot of people think a lot of people, think their work is over, their career is over, their best years are over when they're 40 or 50 or, you know, there's all the shoulda, coulda stuff. And I am a deep advocate of the fact that we have chapters and you can do an enormous amount at any age as long as you stay engaged, as long as you still get excited about what's possible.

And so I love doing this. And I hope there's going to be a whole lot more people like me who continue to do it for 50 years or more. Summer is here, and Ralph's is your destination for hot savings. Find unique items at low prices with a wide assortment of products from our exclusive brands. Fire up the grill with cookout classics like burgers and brots, and don't forget, delicious produce like fresh melons,

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