S5E8: Alexandra Wilkis Wilson, Co-Founder of Gilt Groupe, Is Sharing Her Experience With New Founders as the Co-Founder and Managing Partner of Clerisy

Welcome to The Room Podcast. I'm Claudia Laurie, co-CEO and founder of Pryve.

And I'm Madison McIlwain, partner of seed stage investments at Defy VC. Claudia and I are friends first and and business partners second. Living in the heart of Silicon Valley, we know what it's like to be on the inside of innovation, having worked at flagship companies like Gap Inc. and Uber. Now in our roles as a founder and a funder, we're changing the face of technology through our mission to bring more people into the room where it happens.

With past guests such as Shikshir Mehrotra of Coda, Michelle Zatlin of Cloudflare, and Grammy Award-winning Ciara, our past guests' companies are currently valued at over $73 billion. If you're a first-time founder or emerging funder who wants tactical insights into starting a company, venture capital funding, hiring, and more, this is the podcast for you.

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Happy International Women's Day. We're so honored to be releasing our 50th episode of The Room Podcast today and highlighting the incredible achievements many of our female-identifying guests have accomplished. As we wrap up season 5, we're delighted to sit down with Alexander Wilkis-Wilson, a 3-time founder turned funder who's helped to build iconic businesses such as Gilt and Glam Squad. A born and bred New Yorker with Cuban roots, Alexandra opens up about her early career in investment banking and retail. These roles and her double degree from Harvard laid the foundation for her first company, Gilt. Many of you may remember Gilt from their iconic online sample sales, which established the company as the player for buying luxury online during the late aughts. Alexander had officially caught the entrepreneur bug and went on to found Glam Squad. A local service marketplace for on-demand beauty and hair care. We unpack some of the learnings Alexandra has taken with her from these two unique founding experiences. My own friendship with Alexandra began over 4 years ago when I had the incredible opportunity to intern for her in college. Since then, Alexandra has launched an exciting new growth equity fund named ClearSea alongside investment veteran Lisa Myers and now lives full-time in Miami. On today's episode of The Room Podcast, we explore key themes and insights such as guilt and the original drop model, what's next for Miami's tech scene, and omnichannel 3.0. Let's open the door.

Alexandra, thank you so much for joining us here on The Room today.

Thank you guys for having me. I'm so excited.

We're excited to have you here. For our listeners, I've had the pleasure of knowing Alexandra for 5 years now. She's been both a mentor and a friend and a former boss. As we like to start with all of our guests, we always go back to the beginning, just asking a little bit more context on where you grew up, Alexandra, and how did that experience shape your view of the world?

I am a born and bred New Yorker. I grew up in New York City. New York is an incredible city that is such a melting pot of diversity and interesting people and people who walk quickly, talk quickly. They're goal-oriented. They're, not afraid to go after what they want. And I think that's very much a part of my DNA. With that said though, my mother is Cuban and I used to spend, and I still have continued to spend a lot of time in Miami in an island called Key Biscayne. And we actually moved here full-time. COVID gave me the confidence and my husband and our children to make a dream decision, something we only thought would be possible when we were empty nesters and kids in college, and now we live full-time in my happy place, which is awesome.

I think we're all just trying to live in our happy place.

Claudia and I talk a lot about if we didn't live in SF, where would that be?

And we're similarly excited that COVID has opened that opportunity up for the evolving ecosystem where tech can be, and excited to actually touch a little bit more on the Miami ecosystem later today. But many of our listeners will know you because you are a multi-time success successful founder with and CEO, including experiences building Guilt and Glam Squad. Did you always think you were going to become a founder?

No, I did not always think I would become a founder. I would say that I always was an entrepreneurial person and a multitasker and always excited to think of new and innovative ways to approach things. I was that little girl in New York City who thought the best version of a playdate is having a lemonade stand that would also sell homemade bracelets and anything that we could turn into a profit. I say that jokingly, but it's true. I think I've always been entrepreneurial by nature, but no, I didn't know that I would be an entrepreneur and a founder 3 times over. 2007 is when we took the plunge and launched Gilt. So that was the first time I went down the founder path and As I'm sure other guests on your podcasts in the entrepreneurial space have shared, it does become addictive. There's a phrase or a title called serial entrepreneur because it is so exciting. You really do experience some of the highest highs and the lowest lows you can possibly imagine from a professional context, but it's hard to go back to the corporate world for many people once they've had that taste of entrepreneurship and being a founder.

It's so interesting when we get different feedback from guests on, you know, I've always wanted to be a founder since I was 10 years old versus I've always had entrepreneurial tendencies, but it wasn't really obvious until later in my career. Prior to actually going down that path of founder, you attended Harvard for undergrad and business school. I'm curious what the entrepreneurship environment was like there at the time you were at Harvard. Because just a few years ago when I was graduating, it almost seemed like being a founder was a tracked career path that people were prepping for. I'm curious to learn a little bit more about the startup ecosystem at your alma mater at the time.

When I was at Harvard undergrad, entrepreneurship was really not something on my radar at all. It was not talked about as a viable career path. Instead, it was so much more about investment banking and consulting. And I did go down the investment banking path for 3 years. And then came back to Harvard and went to HBS, which was a totally different experience from Harvard undergrad. The curriculum, the friendships, the mindset, totally different. At HBS, I would say I was on a very targeted mission to get out of finance and get into the consumer sector. So I was pretty open-minded. Was it going to be fashion or retail or beauty? I spent as much time as possible just immersing myself in learning about those categories and Ultimately, when I graduated HBS, I took my first job at Louis Vuitton, then I was at Bulgari. So 3 years in luxury. Then we started Gilt. Once I went down the entrepreneurial path, I felt like, oh, what a shame that I didn't take more entrepreneurial classes. I just took the basic first year, what was required. I spent so much more time my second year when the curriculum is flexible, studying as much as I could about marketing and operations and those types of classes versus entrepreneurship. But the funny part is I am still very connected to HBS as well as Harvard undergrad. And when I get called back to do anything, it's always about entrepreneurship. It's always about being a founder and talking about building companies and scaling them and all the ups and downs that come with it. So I feel like my entrepreneurial path within the Harvard ecosystem happened after graduating, but not while I was there.

One of our investors is incredibly connected with Harvard and was always there on campus doing like coffee chats and all of that. And I would never really go because I was so fixated on the classes I was taking that semester and the immediate things that I was doing, making sure that I was getting good grades. And now I'm trying to learn how to sell a product. I wish that I paid a little bit more attention to all the resources that were there. Madison McIlwain and I are fans of e-commerce. I'm curious, could you orient our listeners to the retail climate after you were doing luxury in 2007 when you were starting Gilt Groupe?

2007 was a really long time ago and the world looked very different back then. If you think about luxury e-commerce and fashion, there were definitely not as many options as we have today. And the fact that we were launching an e-commerce site that was behind a registration wall, you had to be a member to access what we sold. Every single day we featured new brands, new product assortments. We made it very exciting. I don't think I even knew the acronym FOMO back then, but really so much of the secret sauce of Gilt was around creating this FOMO. People had to check the site every single day, just in case there was something they might like because they would regret it later if they hadn't gone to check it. And we really created a very new behavior in consumer shopping and we were selling really high price point items granted at a steep discount, but still even at a steep discount, a $10,000 item MSRP on a steep discount might be $2,500. That's a lot of money to be shopping online back then. Back then, a lot of our consumers and my co-founder Alexis Maybank, who's still one of my best friends in the world, we would travel the country and other countries as well and spend a lot of time with our top shoppers and consumers. And they would always say things to us like, Gilt was the first place I ever bought X type of item online. And it was like a dress, a pair of shoes, a handbag, diamonds, things that now are just for you guys, you probably can barely remember when there wasn't e-commerce. It's probably funny to hear these things, but the world changed a lot and changed very quickly. Later when the iPad launched, the iPad launched, I remember when I was on maternity leave with my son and Gilt was invited. It was like a whole super stealth, cool, secretive thing. I didn't even know it was happening. Our engineers, a few of them got invited by Apple to go in total secrecy. They had to sign their life away or something like that to be able to design the app so that when the iPad launched, Gilt was on it. It was very exciting. And then we created this whole excitement of not only being online but also having apps in both iPad and iPhones, etc.

My mom was a big Gilt shopper back in the day, and I honestly think Gilt was probably one of the first salient memories that I have of e-commerce and online shopping because I would remember we would be having a conversation or we were about to do something and the trip like, hang on, what time is it? And then she would check Gilt because she was looking for something specific, whatnot. And then I then quickly converted to being a major Gilt kind of ogler, adding things to cart, not really buying things because I was a kid then, I didn't have a credit card, but I just loved the experience of new things that you could discover, even if they were aspirational and you couldn't buy them.

I can't believe how much this mirrors what today is so commonly referred to as drops, right? Today, Amazon drops, streetwear brands drop. That's really what you were doing in 2007 was these drops.

I totally agree. And I think I only learned the word drop 6 months ago, so didn't use FOMO and didn't use drop, but that is what we were doing back then. Every single day there was a drop, so you had to just check the site. You could literally, as you're describing, I mean, Claudia, your mom might've checked it for 3 minutes to just be like, oop, boop, boop, boop, boop, not interested. Everything about Gilt, whether it was creating the company, building it, the shopping experience, everything was about speed. Consumers had to make shopping decisions, sometimes expensive ones, very quickly, or they would miss out. And I'm getting pretty into NFTs and the metaverse and Web3, and there's a lot of similarities too of when a new NFT drops and, you know, you have to mint as quickly as possible. Oh my gosh, someone else is gonna beat you to the punch. There's a lot of fun similarities now in 2022.

What actually was the aha moment that birthed Gilt's core product? Because now it seems like a stroke of genius that took off. Now it's morphed into many different things like Drops, but what inspired you to structure Gilt in the way that it was?

We were a team of 5 co-founders with diverse experiences, backgrounds, and roles within the company. So, um, I was a product manager. 2 engineers, Mike and Fong, who are amazing. Kevin Ryan, who you guys probably know of. He was initially our chairman and, and got us started. And then Alexis, who was our CEO. And then I was in charge of the merchandising, even though let's be very clear, I did not have a traditional merchandising background. I had to learn retail math. I'm not bad at math, but I did not come out of a traditional federated merchandising program. So I'm an open-minded hirer sometimes, depending on what the role is. If the person shows signs of being an all-star athlete, then maybe they can hustle enough to make something happen.

Especially at that time, Alexandra, for our listeners who maybe aren't as familiar with the fashion ecosystem, merchandising has these tracks like Lord Taylor merchandising, Gap merchandising, and you go through these programs where you really learn to, quote, become a merchandiser. And that really opens a lot of doors into the rooms where you can be buying these types of clothes that you were able to purchase for Gilt. For you to not have that background, that is a handicap at the time to actually be respected and able to purchase some of these larger purchase orders that you would have had to for Gilt.

Totally. But I was very upfront about what I knew and what I didn't know. And then I hired people around me who could teach me what I didn't know and who were excited about taking this entrepreneurial journey. I didn't totally answer your question, which was about that aha moment. I'd say really it was a series of aha moments. Initially, in my mind, the idea was let's bring online the excitement of a New York City sample sale. I still am a sucker for a good sample sale, but we recreated online a lot of the behaviors that you would find in a kind of brick-and-mortar environment. You initially might just grab everything in sight 'cause it might be a frenzy and chaotic and you grab everything into your arms and then very quickly irrational behavior might start to set in of, does this product fit me, suit me? Would I actually use it or wear it? What's the price point? Even though it's a discount, can I really afford it? And then little by little, in a sample sale, the person might not actually buy everything that was initially in their arms. So we would mimic that behavior from a cart perspective. You only were able to put items into your cart for 10 minutes, and then after that, someone else could snatch them. We had so much fun creating the product for the experience. And what was so fun is that every day we were tweaking it. We would learn from behavior. I will tell you that the first sale we ever did, which was November 13th, 2007, it was the Zac Posen sale. Zac Posen was one of the hottest, most desirable brands. And we were so excited to sell him. We started the sale 9:00 AM Eastern time, assuming that behavior would be a physical sample sale where yes, some people would line up, of course, in advance when a physical sample sale would start, but people might trickle in throughout the day. They might sneak out during their lunch break or whatever it was. We assumed that purchasing would happen. Throughout the day. And what we learned basically with our first sale, and then consistently as we started doing many more sales, was that the behavior was the floodgates open the minute it went live. Everyone went crazy and tried to shop as quickly as possible. So we didn't expect that. What that taught the consumer was that if you're interested in something, you gotta make a decision quickly because if not, it'll be too late and someone else will snatch that particular item.

It seems like it was pretty clear early on, especially as consumers were digitally lining up for the sale that you were seeing inklings of product market fit, and ultimately it was a very clear product market fit. We chatted a little bit about building the team, building the product, coming up with the model, but then you successfully raise a lot of venture capital from a number of investors, including NEA, SoftBank, and General Atlantic. Would love to chat a little bit more about your early fundraising journey. Who was the first person to say yes? To you and Gilt?

Nick Byme, who was at Matrix Partners at the time, he was our Series A investor. We were so lucky to have him. He understood the vision very clearly and was really a terrific partner in the business. I will say that we definitely had some meetings where the investors, not all male, I remember actually pitching a whole group of women, they just didn't get it. I would I would talk about the merchandising and I would explain if you could get a normally retail $500 shoe for anywhere between $200 and $250, that's incredibly exciting to a consumer. And in the beginning it was just female-focused. And then 6 months later we launched Gilt for men as well. A lot of these VCs who were, I'm sure, incredibly wealthy themselves, they would just start laughing and be like, my wife would never buy a $500 shoe. What is a $500 shoe? And I was chuckling I would say to myself, yes, I'm sure she does, but maybe you don't know. And if you want to go for a walk at Saks Fifth Avenue or Bergdorf or Barney's at the time with me, I'm happy to walk you through the shoe floor. And actually a lot of the shoes are even more than $500. So a lot of them just didn't understand that and thought, oh, this is some cute little girly project, but that's okay. We showed them and Nick Baim was an awesome Series A investor and a critical part of the story and the journey. So it's so important to get those early investors who really understand what you're building.

It's invaluable to have someone who maybe even if they aren't the core customer for your product and your experience, who believe in you and the team and the vision of what you're going after. Sounds like Nick was that at the earliest stages for you all. A lot of the points you're making tie back to a key theme of ours at The Room, which is around access. You were unlocking access to luxury fashion at a much more mass scale than was traditionally available at the time, given sample sales are often hyper-local, usually in New York. Curious about the supply chain challenges or opportunities that you faced in getting this access open for the retail partners to ultimately have a meaningful and robust catalog of items to purchase for your Gilt customer base.

I would say there were two main challenges, many more, but let's just stick to two for now. The first one was convincing the brands brands to partner with us and convincing them to be comfortable with selling online and online at a discount. Many of these brands didn't sell online at all at that point, and that was not easy. I was obsessed with just going to every trade show I could, leveraging every contact I had. A funny story I've shared before is my eye doctor, her sister was married to the brother in the Judith Ripka family, and I was like, hey, can you connect me Hey, can we talk to them? We'd love to sell Judith Ripka, which was a beautiful jewelry brand, and they were one of our early fine jewelry brands. I would shamelessly reach out to anyone that I could think of who might be able to open a door for me. And then I had no problem cold calling. I got a sick pleasure from cold calling. Back then when I was at the beginning of my journey, if I sent out 10 LinkedIn messages or cold emails, back then I was guessing email addresses sometimes, I would take one response as a success as opposed to 9 rejections. And I am, as a person, very organized, so I would keep track of every conversation. And I remember one brand being like, "Come back to me when you convince Marc Jacobs." And so lo and behold, we convinced Marc Jacobs to partner with us and be featured on Gilt. And you can be sure I told that other brand that said, "Let me know when you have that brand." I would send them screenshots of the Marc Jacobs sale. I said, "Look how beautiful this is. You could do it too." I did not take no for an answer and just kept trying and trying with a smile, trying to be charming, but also I would say pretty relentless. The other main challenge that we started to realize probably 6 to 12 months into the business was we were building a business that was basically based off the mistakes that brands were making, mistakes in forecasting. And of course then 2008 came and the world changed very much, and there actually was a lot more excess inventory available. But we were relying on the leftovers, and it's very hard to build and scale and forecast and plan a business that's relying on the mistakes of others. So we strategically had to get ahead of supply chain with a lot of these brands. It was easier to do with American brands than European brands just because we could get access to the top decision makers much, you know, more easily going into the New York headquarters or LA headquarters. But we came up with really creative solutions to earmark inventory for us that would not aggravate the full-price retailers like the department stores. There was a lot of complexity. We don't have time to get into it in terms of how we paid for product, who stored the product, when we could sell, when we could break price. But we learned it and we navigated it. And you have a good question of how do we think about supply chain? And it was really just trying to be as creative as possible. And in many cases, we came out as a really creative solution for brands to actually make a lot of money in partnering with us. And we grew very fast. Probably shouldn't be sharing the numbers on the podcast. We got to $25 million in our first full year, and from there it was a rocket ship. The growth was exponential. It was hypergrowth like you rarely see. That was exciting.

That is so exciting and fascinating to hear about some of the complexities behind the hood, especially given old guard of retail and their perspective on what is value and how can you be generating it for their brand. I know we talked a lot about that when I was at Rent the Runway. It creates this opportunity for the younger generation to purchase in at a price point that they perhaps can do in rental. Obviously it's much more affordable, but it still creates some stigma because the brands don't necessarily want that access. And so you're almost trying to open a door that that they don't necessarily always want opened. As we talked about at the beginning of the podcast, you are a multi-time successful founder, serial entrepreneur, and after Gilt Rocketship, you went on to found Glam Squad, which for those who might not know, is an Uber-style business providing in-home hair and makeup and nail services for that busy woman who's on the go. This business model actually is quite different than Gilt's in the sense that it was reliant on a local service market. Marketplace. Claudia knows those very well, given her time at Uber. We're just curious about the evolution of the gig economy. And personally, as you look towards your investment strategy today and just reflect on your time at Glam Squad, are you more or less bullish on the gig economy than you were when you initially founded Glam Squad in 2014?

2014 was a different time too. There was so much excitement around the gig economy, on-demand economy. I was fascinated. I wanted to learn as much as I could. There was the Uber of everything and Uber competitors, and then there was Airbnb, and the list goes on and on. And so it was really exciting to build a business that could capture a lot of that momentum and excitement and desire from a workforce that really valued flexibility. It was a great experience, and I loved my 2 years at Glam Squad and still use the product nowadays. I now have a growth equity fund with an amazing partner. Her name is Lisa Meyers. And our fund is called Clarity, and we're a growth equity stage fund investing in consumer and techsumer companies. And we have not really looked at any gig economy businesses very seriously. We've had a few pitch to us, but it has not been a priority for us in terms of what we're excited about at this moment. So does that mean we'll never invest in one? No, but I would just say that none of the opportunities where we've really dug in have been in the gig economy.

That really dovetails well into our next question, which is diving a bit more into Clercy and the investment strategy that you have looking forward now to the future of backing the next generation of entrepreneurs.

I have to tell you, I'm having so much fun now on the investing side of things, knowing how hard it is to to be an entrepreneur and the blood, sweat, and tears that it takes. I'm really enjoying being an investor and partnering with a woman like Lisa Meyers, who's been an investor her whole career. So I'm learning a ton from her and hopefully adding a lot of value to not only the portfolio companies that we have, but every single day I'm talking to founders and we have a pretty concentrated portfolio strategy. So our intention for Fund 1 is to invest in anywhere between 6 to 8 companies. But we meet with probably 10 companies a week. In all those conversations we have, it's more often that we're not going to invest in a company than we are. And so in all those conversations, if I'm able to share any nuggets of learnings from the 3 businesses I co-founded or other roles that I worked in, or the 70 startups that I've been either an angel investor in or an advisor in, I'm happy to share with those founders. And sometimes I'll say to them, look, have you thought about XYZ, or have you been introduced ABC, it takes me 30 seconds to write a quick email and making an introduction. I don't think about it like, I'm not going to help them if one of our competitive investment funds is going to— I don't think that way. I'd love everyone to be successful on all levels. So we're loving it. We are growth equity stage. So for us, we're looking at the two investments we've made so far have been Series B. We're looking for businesses that have found product market fit. They've found product service fit. They're scaling. They need some capital. But in addition to the capital, they need help. And so Lisa and I really partner with the founders and their management teams. We'll help them grow their teams. We'll help make sure all the right people are in the right roles, think about different growth strategies, revenue streams, partnerships, and of course, thinking through what do we need to achieve in the timeframe that we're targeting to get to an exit that that makes all parties happy. And so I'm loving it. I'm sure you're loving it too.

Yes, it is so fun to be on this side of the table and to your point, getting to really be that thought partner and door opener for the entrepreneurs. And they're doing the hard work, honestly, Claudia, you're the one in the fight, but it's a pleasure to get to be that confidant that I think you get when you're sitting a little bit outside of the fray that comes with being an investor. It's so exciting, Alexander, to see you in this this role as an investor and the evolution of your incredible career as both a founder and an operator. You mentioned you recently made a personal move to Miami, which has always been a place you've loved and a space that has seen a lot of innovation and disruption from where we're sitting in the past few years. Really curious if you could give our listeners an insight into the evolving technology ecosystem down there.

Oh my gosh, it's so fun, and I feel like the tech scene here almost feels like summer camp. I'm not even joking. My kids find it hilarious that every day it feels like I come home and I'm like, I made a new friend. And they look at me like, I didn't know grownups made friends. And I'm like, of course they do. And not only did I make a new friend, but I learned a new thing. There's so many interesting people moving here too. And so I really feel like crypto and blockchain are so important here. So there's a lot of interesting people, companies, investors, creators, coming together here. I can't even tell you how many WhatsApp and Telegram chats I'm on that have to do with tech or Web3, and people are just super inclusive and collaborative, and it's so easy if you have a question, an idea, an invitation, you just share it and get flooded with responses. Yeah, I think everyone's excited to be in this moment together. Mayor Francis and also Mayor Daniela have done a lot lot for attracting new types of people to the city. I recently joined the board of the PAMM, the Pérez Art Museum, which has also been interesting for me to get involved in the arts and not only benefit from all the great things happening in Miami, but also hopefully contribute. It's amazing. And I think that anyone who comes and visits, people who visited during Art Basel, for me, Art Basel felt just as much art as tech-oriented. There were so many tech-oriented gatherings. There was a conference, NFT Basel. The city has changed so much, and I think for the better.

Just a few years ago when I was coming out to San Francisco because I felt I was going to miss out if I didn't. Now I'm sitting in San Francisco seeing all of the Instagram stories of my friends in Miami, feeling like I'm missing out. So it's really cool how that's changed.

Come visit.

Maybe Madison McIlwain and I will both make a trip down together. I'm curious a little bit more about the macro landscape. Of the shifting models of consumerism. You've been at the front row to sample sales, online shopping, gig economy, and beyond. What does the next 5 years hold for commerce?

Omni-channel was a word that had been thrown around a lot over the past several years. Now we don't hear it maybe as much. And so omnichannel, when it started getting used, it was like a brand needs to think about Bricks and mortar and online and mobile commerce, if they have an app or whatnot, and social media. And that was this omnichannel experience. And I think that over the next 5 years, omnichannel will also add on one extra dimension, which is the metaverse. And that is exciting and perhaps terrifying. And the brands that really just dive in there and figure it out sooner rather than later, I think will really differentiate themselves.

I work with a lot of D2C and CPG brands, and just this past week I was in a Zoom call with 10 different CPG founders all discussing NFTs and launching NFTs backed by physical products that they sell. And it was just amazing how quickly so many of these founders are are innovating on what their business model is, even though they historically are not deep in the Web3 crypto community. That resonated with me because I just saw how much enthusiasm and energy there is to explore Web3 as just a new channel crossing the border between those online experiences and their physical products.

I agree. And it's still so early. We're really in the early innings of this. So I think a lot will evolve in the next 5 years.

Just in that vein, we are so early and a thing that I'm struggling with is separating the hype from the real innovation and the real evolution of what will become omnichannel 3.0 into the metaverse. Alexander, how are you thinking about evaluating projects, evaluating technology opportunities that unlock the infrastructure and unlock the experiences without getting caught up in the hype that maybe perhaps won't stand the test of time?

I think about it two ways. So one is in terms of Clarity and our portfolio, trying to think of the companies that we partner with and invest in. Does an NFT or some form of Web3 strategy make sense? And it might not make sense for every single company, and that's fine. That's okay. So just thinking through different strategic approaches. What would be meaningful? What could be differentiated? What could be buzzworthy? What could be lucrative and profitable? And we're at the early innings of figuring that out, but definitely just trying to speak with as many experts as possible. Actually, yesterday we held a webinar for our Clarity LPs on the metaverse, and the idea was just to educate them. So some of them are pretty knowledgeable. Some had probably have no idea what that is, maybe at all, and I think it was enlightening and exciting for them. Again, we as a fund, we're a little later stage, Series B, targeting companies that are ideally profitable, over $10 million in revenue. A lot of the Web3 companies are still in their early innings and might not be a target for us, but looking to partner. And then on a personal level, I've gotten really into NFTs and learning that through the Miami Tech community. And I've been into crypto as an investor for the past 5 years. Lots of learnings. It's so fun. And I'm the type of person who, if I don't know something, I'm not ashamed and not afraid to ask. And I don't care if people think I look dumb. I may look dumb in one group and one context, but compared to a lot of my friends, they don't even know what DeFi is.

I so relate to that. And I just had the biggest blunder. I will expose myself.

I got my first NFT and I was all excited to make it my profile picture on Twitter.

And I posted and said, oh, new PFP.

I'm so in the know, and I tagged the wrong artist.

I totally put the wrong person, which is such a faux pas, because obviously you want to honor the beautiful art that they've made. And I just felt like such a silly goober on Twitter. But yes to learning as we go.

It's all about learning. But you can also delete that post and—

I did delete it.

So all good. No one needs to know. Now you shared it with all your fans.

Madison McIlwain, I did not notice. We have our last question that we ask all of the guests. Asked on our podcast. It's our hero question for the show, and that is, who is a woman in your life that had a profound impact on yourself and your career?

You told me I can't say my mother, so I won't, I won't say my mother, although she would have been who I would say. I'll pick two women. I love building things with other people, not alone, and so I've had two amazing partnerships in my career with other women. The first one was with Alexis Maybank at Gilt. I had a really fun catch-up chat with her early this morning. We learned so much from each other. We built something incredible together. We had each other's backs. We wrote a New York Times bestseller together. We are godmothers to each other's children. We're still very close, having gone through a lot, a lot of amazing moments from meeting Madonna to various challenges, et cetera. So she is the first person I would say. And then the second person I would say is Lisa Meyers, my current partner. I am learning so much from her. From what we are building together in Clarissy. It's just the beginning. There's so much more to come, and we really are a very well-suited dynamic duo for the type of fund that we are. It's an investor-operator combination that we have, and I think it's the right way to approach the category of investing that we're going after, consumer and techsumer, this stage. And I'm really loving working with Lisa now in this next phase of my career.

Thank you so Thank you so much, Alexandra, for coming on the podcast today, sharing all of your stories. We are so excited to keep watching everything that Clericy does, and just incredibly excited to share your story. So, thank you.

Thanks for having me.

Thanks for listening to this week's special 50th episode of The Room Podcast. To get The Room in your inbox every week, subscribe to our newsletter at theroompodcast.com/newsletter. /newsletter. We'll be back soon with more guests who are opening the door to all sorts of possibilities.

Support for The Room comes from Silicon Valley Bank. Silicon Valley Bank understands these questions can keep founders up at night like Claudia. For over 35 years, Silicon Valley Bank has helped high-growth companies through scalable financial solutions, plus insights and expertise that many other banks just can't, which could be why 50% of US-based venture-backed tech and life science companies bank with SVB. Learn more at svb.com/next. Silicon Valley Bank, built for what's next.

Cooley is a global law firm built around startups and venture capital. The firm has been devoted to entrepreneurs and investors, partnering with both to transform breakthrough ideas into successful companies. Cooley works with thousands of entrepreneurs and newly formed companies to ensure that they are structured for growth and long-term success. Since 2005, Cooley has been ranked the number one most active law firm representing VC-backed companies going public. Learn more at cooley.com and cooleygo.com, Cooley's award-winning free legal resource for startups.

All opinions expressed by Claudia and Madison and podcast guests are solely their own opinions and do not reflect the opinion of DefyVC. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.