Alexandra, why don't you give us a little quick background about your career, your history as an entrepreneur, and just a quick background so our audience gets to know your story.

Sure. So I am a serial entrepreneur now turned growth equity investor. I am most known for being co founder of Guilt, which we launched back in 2007, really the leader in flash sale ecommerce in the US. And after that went on to be co founder CEO of Glam Squad in the on demand beauty services arena when there was the uber of everything I had to get my fix of on demand. Went on to do another two startups. Partnered with a man named Michael Klein. One of those, it was called Fitz. We sold to Tradesy, a peer to peer luxury reseller.

The other one we sold to Google before it launched. And then I spent two and a half years leading everything digital and consumer at the pharmaceutical company Allergan, which was a lot of fun to be in big corporate with pharma budgets learned a lot. For those that don't know Allergan, you might know botox or juvederm. So they had a big, exciting aesthetics portfolio, and I hired and led a team of 70. And then after Allergan got acquired by aBVI, I finally went down the path I knew I would eventually go down, which was investing. So I partnered with a woman named Lisa Myers and we launched a growth equity fund called Clarity. And it is consumer and tech zoomer focused and growth equity stage. So for us so far, that's been series B, and we've made three investments.

It's an $84 million fund and we are having fun with our fund, let me tell you.

It's so exciting to be able to apply all that experience operating and not just in one specific sector, but across multiple different types of companies and being able to apply that again as an investor. So I think that's really cool. I definitely want to cover a lot on the growth investing side, especially in the consumer and tech sumer sort of space. But why don't we go back a little bit further to Guilt and maybe even before Guilt, right? Like, I think today a lot of people who are listening know Guilt and it's like an icon in ecommerce. It was like one of the big sites that popped up. It was actually even for me, it was one of the first places, it.

Was my first ecommerce shopping experience. My sister invited me and I think we should also double click on that one. It was one of the earliest referral invite programs that took the Internet by storm. I'm curious, where did the idea for Guilt get sparked from? I guess that attaches to your career previously from Guilt, where did sort of all of this it was sort of the perfect storm that came together. Where did all of that come from?

So, lots of questions. Let me see, because I could talk for hours. We actually wrote a book about building Guilt, alexis Maybank and I, my co founder, and she's still one of my very best friends. We wrote a book by invitation only. How We Built Guilt and Changed the Way Millions Shop. So if anyone really wants to learn more, definitely check the book out. Guilt's idea was really a series of AHA moments. So part of the concept was to take the excitement of a New York City sample sale online.

So prior to Guilt, I worked at Bulgari running retail stores in the US. Before that, I was at Louis Vuitton in their management and training program, which I did after getting my MBA. So super humbling on the sales floor, wearing a uniform and an LV pin, putting shoes on people's feet at the flagship store and at the Shop and Shop in Saks Fifth Avenue and really learned the nuts and bolts of retail. Guilt, for me, 2007 was my first ecommerce experience. Never went back to brick and mortar, really sort of stayed in ecommerce. But we took a lot of, I think, clever marketing tactics and approach back then that wouldn't necessarily apply today. So one tactic was the $25 give get referral. So if I invited the two of you the first time you actually spent money shopping on Guilt, if you became a member, I would get $25 for each one of you and you would get $25.

So that really helped us grow initially. I mean, it was by invitation only. And the idea for that was really two ideas. One was like, you think of a really hot nightclub that has a velvet rope outside. The reality is, when it's brand new, it might actually be empty on the inside, but you want to create that magic and that hype. So that was one idea. And while I was in business school, I was there 2002 to 2004. I was really into something you guys probably never used before your time, but it was called a small world, and it was kind of like a Facebook concept.

It was a social network. It was very international, really popular all over Europe, a little bit in Latin America, and it was a way to connect with people online. And you had a limited amount of people that you could invite. And I was really into it, had a big network there. And my business school days were the days of traveling nonstop around the world. And it was fun because if I was landing in Istanbul or in mykonos or in, you know, you name it, Croatia, I could look and see were there members, friends with members that I was friends with who could kind of guide me and give me local advice. And so that was very much by invitation only. So we liked that idea.

Also, Gmail had just started around then, a little before I forget what year. But that idea, the early beta testers of inviting people. So we figured, let's start guilt by inviting everybody we know, encourage them to invite everybody they know. And this was really before any kind of SEO SEM. We didn't even want a footprint online. We wanted everything to be behind a registration wall. So very different from today's DTC strategies.

It was likely very the technical component of the business was very important because you didn't have the out of the box tools that you have now for referral programs. Now there's like hundreds of choices for running referral programs, even payment processing, probably. It was fully custom built. How much was the technical component part of the success of the company? And how should founders think about that side of their business today compared to then?

So again, for your listeners, this was 2007. So very different time and world. And as you say, we didn't have amazing tools that you have today, like a shopify. So two of our co founders, mike Brizick and Fong Nguyen, they were incredible engineers. We were very much building a tech company with an engineering core. And that was fun, actually bringing people from the world of fashion and retail with people who were hardcore engineering talents and just kind of merging these very different worlds and cultures, literally. There was language barriers, so to speak. The engineers didn't know taxonomies like hosiery when we were buying products, and many words that the fashion side of the business did not understand on the tech side.

So that was really fun, building a combined culture. But as you say, we built everything internally. And I think when you work with great engineers, they almost get insulted if you were to get something off the rack. They want to build, they want the challenge, they want the excitement. So, of course we built our own referral program and inventory management system and we had this really complex admin portal that we could all access. And we were building the business while we were driving at what felt like 500 miles an hour. So sometimes that can lead to just chaos and craziness and you have to every day prioritize what's urgent, what's important, what's nice to have, but we can live without it. And so we always prioritize the site, the front end of the site, and sometimes the back end.

The admin wasn't maybe as beautiful or as well organized as what the consumers saw, but you always prioritize the consumers.

And then also on the business side for guilt. I think one of the things that was really exciting about the product at the time was you would see all these brands, like luxury brands and retail brands that you hadn't seen in this sort of shopping environment. So you guys did a really good job of taking something that felt very premium and you were giving also like insider prices. I guess my question there is on the business side, because all those things that you were doing and those relationships that you were forging, a lot of those principles, I'm sure, are pretty applicable today to entrepreneurs building out different sort of marketplaces or partnership led businesses or everything like that. So how did you guys go about starting getting some partners, getting your first retail partners and building out that side of the business? On the supply side? Yeah.

I mean, a lot I think back then is applicable today. So if you're starting a business that's doing something that's never been done before and you are pitching to partners who have to scratch their head and Understand, like, wait, what are you talking about? What is web three? What is the metaverse? What is an influencer? I mean, whatever it is that your company is all about, you have to educate the people that you're trying to convince. So in our case, my role was traveling around the world convincing brands to trust us with their most prized possession, their inventory and their brand and do it in a way that felt appropriate and that was really uncomfortable for a lot of these brands. They did not feel comfortable selling online. And the idea of online and at a discount was just terrifying for many of them. Many of them didn't even have full price Ecommerce. So you got to remember 2007 or even 2008, 2009, as we really got scaling was just a different time. So how did we convince them? I mean, it started with our existing network.

And I love networking, I love meeting people, love keeping track of people really use LinkedIn and tools like that constantly. And I would reach out to. I would make lists. I'm a big list maker, so I'd make lists by product categories. So let's say within women's fashion, it would be by category. So you'd have like ready to wear accessories, jewelry, beauty, et cetera, and then you'd bucket it maybe by price point and then every brand I could possibly find. So back then it was less about I mean, I would look online at what the department stores like Neiman Marcus and Saks had online, but it was really combing the racks at all these stores, writing down, keeping lists, what brands do they have, what new brands do they carry? And then I would see if I knew anyone there or if I knew someone who knew someone there. And for me, I get a crazy rush from cold calling.

I have no problem cold calling. I don't take rejection personally. If I send ten emails and nowadays my hit rate is better. So let's say today maybe I send ten emails and seven write me back. I'm like, yes, seven people wrote me back. I'm awesome. Whereas someone else might be like, oh my gosh, three people rejected me. And you just can't live life that way if you're an entrepreneur and you're hustling and all ODS are against you as a startup.

I mean, when we started Guild, everyone in the fashion industry told me it was a terrible idea, it was never going to work. And they had all these reasons why brands don't need you. They have sample sales, they have outlet malls, they have the Lomans and TJ maxes and finally basements of the world. Why would they need you? And the fact that you're online? No way, no way, no way. So you got to hustle as an entrepreneur and you have to have really thick skin.

I think the same happens to founders that might not be focusing on problems that might be big enough, that might not have challenges that are big enough or problems that are big enough. And the reason I'm saying this is because the same could happen with team building. So say you hire ten people and then three of them are unbelievable talent, and then now you have two of those or one of those that it just isn't meeting the bar and the performance, and you could obsess over that one person. They're not here on time, they're not doing this, when instead you should probably be focused or excited that these three people are doing the 80 20, they're driving 80% of the impact. Do you see the same applying in teams? And is it the same principle and mindset? Can you look at it that same way with teams as well? Or should you always push for the absolute?

I have a lot to say about hiring and building teams, and we all know you guys have lived this yourselves. When you're building a startup in your early days and you don't have a lot of money to pay people, and you have to motivate them, incentivize them with the vision, the mission, maybe some equity. And it's not just the bi weekly paycheck that they're getting. There's other reasons that you want to convince them to be there. I think that it's so important to hire the best athletes. So for all the roles, if one were to hire me specifically for the role that I did, let's say at Guilt or at Glam Squad or even Argan, I did not have the exact experience I had never done before when I started Guilt, I had never done online. Just I think I work really hard. I have an incredible work ethic.

I will not take no for an answer. I like building teams. I'm super driven, for example. So when I'm hiring someone, I mean, it depends on the role, and it depends how big the team is too. So this is take it with a grain of salt. But I'm more excited to hire someone potentially with less experience who's just hungry, hungry, excited, passionate, is going to wake up every morning potentially without the alarm clock, just super excited to get going on whatever the task is at hand. And I think sometimes when you have someone who is negative toxic, brings the culture down, it never gets better. It just doesn't it gets worse.

And you really got to nip that in the bud. If it's not so much like a negative toxic situation, but maybe just a low performer, that's not as bad. But I think you really want to hire people who you can trust and who are going to take on, who are really just hungry and thirsty and always want to take on more, as opposed to maybe what you would find more in stereotypical corporate America. Which isn't true, by the way. I really did love my allegan experience, but it might be more like a nine to five attitude and turn my phone off on the weekend and I'll turn it back on 09:00, a.m. Monday morning. That does not work in a startup, as you guys know.

Well, a lot of that can be you can set the stage as a founder in the hiring process and be transparent and set the expectations right in the beginning. I think it's really encouraging that you say that because for first time founders, even if they wanted to hire super experienced, they might not have the network, they might not have the pool to attract that kind of talent. So it's really encouraging for them to hear you say that, that you might be at an advantage with people that are just really hungry and might have the ignorance is bliss approach to a market that hasn't been proven or anything like that. And then what are the attributes of teams that create magic? Because you build teams in all of these different sectors. You then went to Services Marketplace outside of Ecommerce. Yeah, what are the attributes that create magic?

So I think diversity within teams is super important. So diversity not only on the outside, but also in well, certainly in experience, but for us, we did this early on at Guilt, and then I used the same coach for Glam squad and even brought him into Allergan. If you take a personality test like a Myers Briggs, it's really important that not everybody has the same profile and thinks the same way. You don't want everyone 20 person team or ten person team. If 50% of the team members have the same profile, that's not good because that means people are thinking the same way. It's really important to have different perspectives. It's good to have some team members who love data and want to analyze every aspect of data they can possibly get, and that's really important. But then you also need some decisions to be driven by gut instinct.

Everything about Guilt that we did was fast. We built it fast. You shopped on the site fast. The sales were on and off quickly. We received inventory. It always felt like going a million miles an hour. We hired, we grew fast. There was a two year period where our team went from 25 employees one quarter next quarter, 50 employees next quarter, 100 employees next quarter, 200, 400, 800 employees.

Like doubling every quarter. That's crazy growth, which is exciting, but also puts a huge amount of pressure on so many aspects of the business, from physical space this was back when we worked in offices together, to just thinking through ORC charts.

And whatnot I do want to ask about through that, since you brought up the timeline, I think you guys also powered through a potential consumer economic downturn. That period was around what year? Specific?

2008.

Right. So how did you navigate that? And the reason I'm asking that is because we're starting to see some of this now. How should founders think about operating in a market like that with consumer goods?

Sure. Well, I'm definitely not an economist, and the reasons for what happened in 2008 versus what's going on now were very different. So in 2008, and I hate to say this, but I do think that the recession back then, which kicked in after Guilt already started, I mean, we didn't create the business because there was a recession, but the recession accelerated our growth in a few ways. One was on the inventory side, which is what that was kind of focus number one for me. Although, as a founder, you wear a million hats, as you know. But brands that initially maybe didn't were nervous to partner with Guilt or hadn't quite said yes. But for me, if a brand says maybe or no, I would just interpret that as not yet. I'm going to go back and convince them.

So a lot of brands that had been on the fence all of a sudden as the recession got really bad. And they were getting returns back from their retailers, like department stores. All of a sudden, they were calling me and saying things like, okay, we had one luxury brand, Valentino. I'll tell you, I used to have to be secretive about this stuff, but I guess enough time has passed. And the CFO Valentino is like, I have $400,000 at cost of inventory that I'll sell it to you for four hundred k, and you need to tell me by end of day today. And $400,000 at that moment in time for us was a huge amount of money. Like, we had never made an inventory purchase anywhere close to that. But it was Valentino.

It was an incredible brand, and it was sight unseen. Usually when we bought and chosen, they.

Reversed the flash sale on you.

Totally. And then they create this FOMO for me. Well, if it's not you, I'm calling Century 21 next. I'm calling Lomans. And I'm like, anyway, so we made the decision, we went forward, we purchased the inventory on the inventory side. Definitely a lot more opportunity became available. It put pressure on us because we needed more capital to fund that inventory. Initially, we thought we could consign it, but in the troubling times, these brands needed cash for their own future and stability and for them to be able to buy fabrics and materials for their future seasons.

Consumers were still shopping. One was a lot of consumers, let's say New York City, which is where we were based, they liked the feeling that guilt was more secret and they could buy online. And they weren't necessarily walking around Madison Avenue in New York City with a big shopping bag. But it came discreetly to their home, and it wasn't like, as conspicuous consumption as retail shopping in stores. And then people felt good about getting a deal. Everyone loves to get a deal. It doesn't matter how many zeros you have in the bank. It still feels great to get a deal.

And so for one person, that could be a Rebecca Minkoff handbag, 50% off feels great. And maybe you're getting it for, I don't know, $100 or something like that. And for someone else, it could be you're getting a $20,000 Valentino gown on sale for whatever, $2,000. And that feels great. So it can happen at all price points.

Yeah. And then I want to move over to sort of the other businesses you built. But one last thing is how did the magic come about? The flash sale component? I feel like that is probably one of the largest key ingredients for Guild, being such a success of the timeline of the urgency of each deal. I think, for example, Hotel Tonight is an app that I use a lot that has an element of that. And you could have just done it every now and then, but it became a core of the business, which was probably very counterintuitive to what advice must have been, or how traditional discount deals work.

Yeah, well, there's so many things we did then that were different from today's world. So, first of all, and it's changed, but when we launched, there was no search bar within Guilt. You were not going there with intent to be able to find a black T shirt. You were going, you'd see? Okay, are the brands or product categories that I'm interested here? Great, okay, let me look really quickly. If not, let me leave. But you weren't searching white sneakers in your size, for example, which that was really different when you think of other.

You weren't collecting data, you didn't know what they wanted.

Well, no, Gilt definitely collected a lot of data, and we were really far ahead with personalization, depending on what purchases someone had made, what clicks they had made, what had been put in their cart, even if they hadn't purchased it. So everyone's home screen, everyone's emails were completely personalized to their behavior. And we were doing that, like, 2010, so a long time ago. But wait, your question the deals, the timeline. Oh, the timeline, yeah.

What was it going to the flash sales?

Yeah, so we didn't even use the word flash sales. That became the word for the industry later. We just were like, let's make it online in 24 hours or 36 hours. And I think what we did well was genuinely create urgency, and especially the first brands we ever sold, like brands like Zach Bozen and Alvin Valley and Rachel Roy and Quiat Diamonds. There was urgency because we didn't have that much inventory, and it was really hard to forecast. When you have a brand new business, are people actually going to buy anything? We have no idea. Are they going to show up? So we opened up our membership November 1, 2007. And we had a goal.

We wanted 25,000 members to join between that date and November 13 when we were launching. And we thought, yeah, 25,000, that sounds like a good number. So we ended up getting 13,000. We didn't pay a penny for those people. We did not use any digital marketing, zero. It was purely our networks, and it was purely I would invite everyone I know and encourage everyone I know to invite everyone they know. And there was the $25 get, and we were maniacal about it. I mean, we kept sending emails and emails and emails, but very different from how a business today gets launched.

And we were actually really disappointed with that 13,000 number, which is funny, because when I tell this to founders today, they're like, oh my gosh, 13,000 registered members with emails and passwords, and you didn't pay for it? I'm like, no, but we wanted 25K anyway. So the urgency came about from day one because the inventory just sold out really fast. And I think that in just about everything related to startups, whether it's fundraising, hiring people, selling products or services. Urgency is really important and I think if people feel like an opportunity is going to be available forever and there's nothing that really pushes them to pull the trigger, that's not know. If anything, we had so much urgency, it was stressful for people. I mean, Alexis, my co founder, and I, we would travel around the country meeting with our top shoppers and some of the stories we heard over the years were crazy. For example, an emergency room heart surgeon would tell us stories that she was so addicted that she would duck out in the middle of surgery to shop at 12:00. And we were like, oh, my gosh, are you kidding me? Well, she wasn't quite a surgeon, but she was in the Er.

We definitely heard all kinds of fun stories.

The reason I ask is because nothing works for me more in sales than urgency. And I don't see it implemented enough in innovative enough ways today in commerce. I think, for example, NFTs sort of have an element of urgency, which is limited supply, and then if you don't buy the initial run of the limited supply, well, there's going to be more supply, but at secondary market rate. And so I think there's a lot of opportunity for companies to continue innovating in commerce, in urgency pricing. But what I find well, the thing.

With NFT, so I totally agree with you on NFTs having transparency, sorry, NFTs having urgency. The challenge is there's transparency there. So you actually know, usually as a potential consumer of an NFT, you know how many NFTs are in an actual drop, so you can see what percentage.

Are actually the supply.

The supply, exactly. And that can make you feel like, well, then I don't need to make a decision that quickly because it's only 20% sold out, whereas in our world, we rarely ever showed the supply. So you had no idea if there are like three dresses available or 30,000.

And there was just the timer there. So you as the consumer, you don't know what's going on. And I've even seen in NFT sales, you know exactly how it's going and you might be like, oh, wow, things are really picking up. If I don't buy it now, it's obviously going to be gone. Whereas what you're saying is for guilt.

It was you didn't know. And in brick and mortar, let's say you guys are going shopping for some hot new cool sneaker you want. If you go into the store and you see thousands of boxes, you're going to be like, oh, I guess it wasn't so hot and not so cool, whereas you'd rather go in and the sales associate says, like, wait, I might have one left in your size. And you're like, please. Whereas online, in normal ecommerce, you don't know the depth, which is interesting.

Did you see the same in restaurant reservations? To me, it's so bizarre that there isn't still. Dynamic pricing for restaurant reservations based on seating inside the restaurant. Because sometimes I'm like, I want that seat and I would have paid for getting that location. Just like a stadium, like a Sea Geek or something. How does that not exist for restaurants? How are people not paying dynamic pricing based on availability and location within?

There's just so many variables, right, from every restaurant is obviously different. And not only that, then you have to do every party is different. So different party sizes. So they have their table management software where they're moving things around and then a lot of times then they'll have the reservation service. So it's a tricky problem to solve. And where we wanted to do for the dynamic pricing proceeded, we came in with a similar model to something like Gilt was doing, where we were like, okay, we want to help sell the unused inventory, provide a discount and a reason to go. But to really get to that level, I think it's a little tough against the nature of hospitality. So another question.

Well, one thing just going back to the Flash sale, I think it's really cool because it's like, you see this concept of drops these days where commerce brands or creators, everyone has their drop. And this was like the OG drop right on Guild. I remember even going onto the site and being like, oh, what brands are dropping this week? So that's really cool to see how things evolve. But those concepts still say the same, right? Like people like Scarcity.

I mean, when you have a consumer that's putting in their calendar an appointment for something that's not really an appointment, an NFT drop, a guilt sale I mean, I would hear so many consumers would tell us funny stories of like investment banking partners or consultants like senior level people. They would put standing blocked meetings on their calendars from twelve to 1215 Eastern Standard like every every weekday.

So if anyone listening has a company that their customers do that reach out to Clarice, those are the dynamics. But what I find really interesting about Dan is the fact that when you went from that into Glam Squad, it's like, it's such a completely different business. If I was in your shoes at that time, it definitely a risky bet in the sense that, okay, now we're going to be dealing with real people interacting with each other in the physical world where it's like the dynamics of a marketplace, say, with Glam Squad it was sorry. With Guild, well, these are established businesses that you can rely on for the inventory. In glam squad. Was it personal hairdressers? Was it individuals or was it businesses? How did you calculate the risk of going in to make that decision?

So if you look at the arc of my career, it's really always except the very beginning, which was investment banking, but that was so long ago, but beyond that, it was always about the consumer. And in an interesting way, all the consumer businesses I've touched, in theory, it could be the same consumer, just different market share of her or his wallet. So going from guilt to Glam Squad, it was literally the same consumer, at least the woman. So it was a time starved, busy, urban woman who appreciated the convenience of having a hairstylist, makeup artist, manicurist come to them, whether that was their home, their office, hotel, if they were traveling at a relatively affordable price point for what those services are. So it was historically, the rich and famous were people who would have drivers, la Uber.

It's democratizing access for what was previously unaccessible for mid level America or whatever. It was just access to the previous rich. So it's the same thesis, basically, and.

The same ICP in both cases, just different services that you're giving them.

Yeah, totally different businesses, platforms, unit economics, supply demand challenges. But I like that. I don't think ever in my career I'll do the same thing twice. I find that boring. For me, I like the challenge of something new, and then I like being able to apply things I've learned previously in a totally different context to something new. And that's one of the reasons my business partner in Claricey and I get along so well. She's been an investor the majority of her career, I've been an operator the majority of mine, and we've both done it across consumer. So we can get just as excited about a consumer health care concept to a pet concept, to a beauty, whether it's you might have some beauty people who are like, well, I'm really an expert in skincare and other people.

Well, I'm a color cosmetics expert. And I'm like, oh, wow, that's super specialized. I'm like, I love it all. I like hair color, skin aesthetics tools. It's all health and wellness ingestibles supplements. It's all interesting. And potentially, it's all targeting the same consumer.

B to B.

I've been an advisor to some B to B businesses, and I definitely understand it probably B to B to C is even more relevant for me. But the businesses that, let's say, I co founded were B to C. The.

Reason I'm asking is because the differences I noticed between B two B and Consumer is that B two B go to market. It almost always has a safe plan of the outbound sales led approach, whereas consumer is very dependent on unit economics, and those can change throughout time. Just how we're seeing now with Facebook ads, customer acquisition et.

So to that point, business development, relationships, deals were really important for all the businesses I've been a part of. So, for example, at Gilt, we had a BD team, and we did this to a much smaller scale at Glam Squad, where we would be for your entrepreneurs. Now, hopefully this will spark some ideas, but if you have a business with consumers and you have certain things that other brands might find valuable, you can pitch that guilt. By the time I left, which was 2014, they had 13 million members. That was a really coveted audience. So there were a lot of brands with deep pockets, whether they were car companies. We did things with Lexus infiniti Audi, Jaguar, where car companies, airlines that had deep pockets would pay big dollars to do cool partnerships that were very creative, had a press angle, had a purchasing angle, and you could kind of bring a lot of factors together and even some glitz and glamour with celebrities like.

What to wear on a flight or something like that.

No, I don't know.

For their employees to wear, like we.

Did some fun things. So one was a specific car model was being launched with Infinity, and Infinity leveraged Gilt to help launch the car. So Gilt brought on two fashion designers. One was Tom Brown. One was Zach Posen. Each designer designed the interior of the know. I think one of them had really cool Stingray and certain colors and very customized. And then we got a lot of press around these cars.

The cars traveled to different markets and we would do events. Miami was one of the cities, I think, where we would have Guilt city events. People could get in the car, pretend to drive it, take social media imagery, and then ultimately, we sold those two cars. I mean, there were only two. There wasn't depth at all, but we sold them on Guilt. So that was exciting buzzworthy pressworthy. And the car companies paid Guilt serious dollars. Other things that maybe an entrepreneur listening to the podcast might find easier would be the equivalence of I'll write about your company in my email newsletter and on my social media, if you do the same on yours.

And so kind of email list swapping, putting inserts into boxes that's been around for a long time, but you can do it in a cool way and maybe an unexpected way. Clever partnerships. We did a cool partnership with Virgin America at Gilt, where we branded an opportunity and sold a whole flight worth Know. People could buy it, and I don't even remember all of it, but it ended up getting an insane amount of press in terms of all ended up. One of the flights we sold was New York to Miami. And then a whole Miami weekend of fun nightlife, as you can imagine, was organized for the group.

Yeah, it's just cool to see as a company grows and you have a really specific customer audience, then more and more brands and more and more partners want to get involved with you. I think it's something like we've even seen with the podcast. First you started out and then you're able to bring in more collaborators and be able to whether it's putting on events or like you were saying, shout for shout, there's so many different things. And I just think being mindful of partnerships all the way up as you're.

Growing your business, I really love partnerships. I think there can be three objectives. So one can be to drive revenue. So is there a partner that will pay your company money? Another is customer acquisition. Is there a way to get more consumers shopping your company? And then the other could be a halo effect. So maybe you're not making money, maybe you're not actually getting any new customers per se, but the adjacency of being able to say that your brand is somehow partnering and collaborating with another brand.

Could just be great for especially and all brands are at different stages. So even when you were saying when you guys did that inventory purchase of all that Valentino sort of merchandise, probably at that stage in the business, this could have been a really transformative thing because you're constantly battling the thing and you're thinking about all the other luxury partners that you want to sign on. You're like, wait a minute, if we have this massive merchandising from Valentino, then we're going to be able to know parlay that into all these other sort of partnerships and initiatives that we want to be able to do. So I think that's the other fun thing about partnerships is everyone's looking at different opportunities and everyone's at a different place in their own business. So as a brand, you always have some leverage and you can always leverage a partnership to push you in the direction that you're trying to move.

Exactly.

Yeah. So why don't we move on to a little bit of Glam Squad stuff? So you'd been super successful with Gilt. You built out that business and then you move into the service businesses. And again, we said similar consumer base, but again, it's a whole new problem. Right. It's a marketplace. You actually have service providers providing a service. So when you got there, having had all your learnings from Guilt, what were you thinking about in terms of the business? What were your key initiatives and what was really exciting to go after and optimize when you started?

I mean, there were so many things to think about and prioritize, but at the end of the day, for any startup, you need to have product market fit or product service fit, and Glam Squad had that. So consumers appreciated having the convenience of someone. Glam Squad started with hair, so a blowout in the convenience of your home or office or so then once we got really positive feedback and encouragement of yes, consumers wanted this. On the supply side, the hairstylists really liked having flexibility over owning their schedule. So whether it was they would open up their we called it their books, their schedules for Glam Squad, at certain times of day, certain days of the week, if you had maybe a mother with small children who didn't really want to be every day with the same schedule in a salon. They liked the flexibility that Glam squad offered them. And then Glam squad also had really weird. So take New York City.

A really popular time slot in New York City to get a blowout was like 06:00 A.m. Or 06:30 a.m.. Whereas Miami not so early, not nearly as early. So behaviors in different markets were different. And so we got that product market fit right and then it was a question of how do you prioritize expansion going into other services? So we chose makeup, then we chose nails. But we evaluated all kinds of other possibilities also from spray tans to facials to massages. And we didn't, but we still went through the process of considering it. And then it was also going to other cities.

So after New York, the next city was La, which was a totally different dynamic. If you compare from a supply perspective how the Stylists navigated a driving city versus a city that's very much public transportation. So these were all things we had to understand. And then as we were thinking about raising future rounds, we wanted to be able to prove that we had a playbook for different kinds of markets. And some markets were you have a city like Washington DC or a Chicago, they're kind of hybrid markets where parts of the city you can navigate with public transportation, other parts of the city you need a vehicle of. Some.

Were, I guess those were the complete opposite spectrums. And so that made it really easy to then expand to not necessarily very easy, but.

Easy for the record.

Well, La is just like the infrastructure is so opposite polar opposite from New York and then so everything else outside of that probably sits in the middle between those two. Right?

Yeah.

So when you're building a business, you always have to go back to the initial question and root of what problem are we know in order to keep that North Star and keep the focus aligned on the business? How did you look at that with a marketplace and a supply and demand? Was it always the supply is first? Above all, was it the demand first? Or is it always we're here to satisfy both sides, both needs, they both have different problems and reasons why they're there.

Yeah, any business that has supply and demand always in this tug of war has to become I live it, you live it. I know. Just think of literally a tug of war. It's always going to be pulling a little bit one side versus the other. And I think you need to do everything you can to keep it in balance. And so maybe there's seasonality, maybe certain times of the year in certain markets, there might be less demand. There could also be less supply. Sometimes it's just less demand.

But the supply is the same. But yeah, many learnings for sure, a lot of creative marketing that I think in all the startups I've been involved in, we try to think about how we can create some excitement for as little money as possible. So, for example, Glam Squad, we did a fun stunt in I forget what year it was. Maybe it was it 2014 or 2015 around Fashion Week in New York. Myself and a woman named Amanda Rosenberg, we took a meeting with Uber and said and it was the time where Uber was doing a lot of clever stunts in different cities. And so we said, could we pull off a stunt around Fashion Week where consumer could book an Uber and also maybe get their hair and or makeup done in the car on the way to a fashion show? Which is not really practical. You don't want a hot tool in a moving vehicle. But that's a partnership.

Yeah, it was a partnership. It was gimmicky. And Uber was basically like, sure, happy to do it. We can add the little icon onto our app. Yes, we can pull this off in three days, but we will not give you the car. We will not put any money into it. So if you can make everything else work, we're happy to put the icon on the app. So we made it happen.

Didn't know how we're going to do it, but I think that's what you find in startups. It's like, okay, how can we find a car? How can we wrap a car? How can we do this as frugally as possible? And I think in the end, we paid $10,000 and it was buzworthy, and we got a lot of press around it. Just glam squad partners with Uber. And Glam Squad was an itty bitty company at the time. We were not a big company. We were just kind of getting going and pulled this off. So I think startups, sometimes I hear founders be like, well, I don't have budgets to do creative things. And you can be guerrilla marketing, tactical boots on the streets doing clever things with fewer dollars than one thinks they might need.

You just have to pick a lane, right?

Yes.

If you're trying to do that, the gorilla marketing and try to figure out Facebook ads, that's probably where the timeline gets.

And I guess they're different sort of channels and different ways you prioritize and think about doing things. And I think the cool part about what you're saying is even when you guys, as Glam Squad did the partnership with Uber, it's like, it takes some creativity, right? Because you're never going to outspend Uber on a specific campaign. But if you can, huh, this would actually bring some value to Uber, right? They'll let us do this, they're going to have a lot of reach. We're going to have a lot of demographic overlap. This is going to be great for our brand. It's pressworthy and all these things. But that takes ingenuity, because that opportunity. Not everyone can suss out and it's a very specific to the I mean.

Also in all fairness, that was a hyper local business.

Exactly.

So if you're trying to build a business nationally overnight, maybe you're not going to want to prioritize in person stunts the same way. That made sense for us. You might want to do something that's more online or it could be through social media platforms or something that could go national versus we were really focused on a specific local audience.

That's why I started with that question because from that dynamic, it's such a completely different business when you go into it. And I guess this bleeds into what you do at Clarice. What are some of the first things you look at in order to just get a full picture of how is this going to grow? Is it a financial model? I mean, it was probably like you probably didn't even know unit economics of the business yet to even play with that. What are some of the tools that you use to really then bring it to that hyper growth and scaling? How do you know it's ready? There's like four questions there again.

Well, so why don't we bring it to today, to our fund clarity, how we look at businesses. So first, what is the business? Is it in a category that we believe has potential that isn't too crowded? And is this company solving a problem or fulfilling a need in a unique way that is not being done by five other companies also doing something almost exactly the same? So it has to really have a differentiated approach then. Tell me about the team and the founders. Are they remarkable, extraordinary? Are they going to kill it and put in their blood, sweat and tears? Do they have track records of success? Doesn't mean they have to have been a founder before. But do they show achievement in their time on this planet? Then this is where my partner and I start to kind of diverge in terms of where our brains go immediately. So she is incredibly numerate, financially oriented. So as soon as possible she wants to dig into the numbers and the KPIs and the metrics. I know that that's really important too.

But my first instinct when someone tells me the name of a brand, I'm looking at their instagram, I'm looking at their website. If I can taste it, try it, feel it, smell it, put it on me in some way, shape or form, I want to do that right away. I can attest to that because that's also how I understand something and I want to understand the flow of if I have questions as a consumer, what tools are available online or in a store or it depends what the business is because we really look across so many different consumer categories, which is part of the fun. I really love the variety that I get to experience now on the investment side that as an operator, there can be a variety, but the variety is different. You're still in one company, and maybe your priorities are shifting or new revenue streams are shifting or new markets or whatever it is, but it's still one company. So I really do love the variety of our day to day.

Well, yeah, and also having all that operating experience, having operated these different sort of companies and understanding the consumer, and now you're in a role where you can actually add a lot of leverage without all the time, and you can kind of get in there, help. Founders really kind of understand what the key things that they might maybe thinking about as they're scaling up and dealing with their own business problems.

Right, yeah. And startups are so hard and so emotional and so many ups and downs. And I think that one on one, founders often open up to me and confide in me and for whatever reason might start crying to me. And I smile because I'm like, yeah, I've been there. I remember when I had migraines every day for six months in the early days of guilt because I was so stressed. Yes, I remember that. It's very real. And so I think founders appreciate that I've spent more time in my career on their side than the current side.

But that also sometimes makes me tougher because I'm like, wait, what do you mean you're going on vacation all the time? Or, what do you mean you're turning your phone off? Or you're not hustling, you're not working hard enough? Or why aren't you doing more things to improve the company culture? So, on the one hand, I'm very empathetic because I do know how hard it is. And on the other hand, I think that sometimes you know what it takes. Yeah, lazy not okay. Many things are okay, we all make mistakes, but I cannot handle a lazy founder. So if I get any sniff of lazy on an introductory call.

And that's one of the, unfortunately, I guess, sadness of a bull run. It's like people get so comfortable, especially startup founders. We've been having such a crazy bull run, especially you add remote on top of that. Yeah, money is flowing like crazy into the market, but people are like, I don't want to go into an office, I just want to work from home. People are choosing their times to work. You don't know where most I mean, we've seen it on the pod and everything. And so I think I'm not excited for an economic downturn, but I do think sometimes it's good to feel the pressure and know what it's like to actually just have to work way beyond what you thought you had to put in initially.

I mean, look, a lot of founders and teams over the past six months that I've spoken to, they'll tell me things like, yes, we cut our burn dramatically. We cut the team. We cut our spend. We cut cut. And I guarantee that at the time when they were making those decisions, like, what fat can we trim? There is no fat. They probably felt, the majority of them like, how are we going to do the same with a fraction of what we had? And you know what? People figure it out. They do because you have to. You make it work.

It's like you're back against the wall. Your survival instincts are going to kick in.

I remember even when we were starting seeded, it took so long to raise. As a first time founder, coming out of college with no experience, it's not easy to raise, right? So for us, we probably lasted like two or two and a half, three years just on well under 2 million. And we were like scrappy. We had like 30 people. Everyone was working for us. We had every restaurant in Boston. And then we went to New York, and then we started to scale up. And then obviously we got all the backing.

But in the early days, it was crazy. I remember the first check we raised, it was like a $50,000 check. We're like, oh my God, this is going to last us forever, right? And then it's just easy to see when you see bigger numbers and you see other founders spending money different ways, it's easy to lose sight of that. But like, you can I love I.

Love what you're saying. I love that it's a little naive tale, a little innocence of these wins that are so meaningful and motivate a team. And you can have that rah rah. We're in this together. I think that's really special. And sometimes I think what you were saying, Ramon, with bull market and so much money, people maybe do get a little complacent. And it's important to have humility and be grateful for all the wins and recognize your team for being overworked, underpaid. So important to celebrate milestones and make the people who have chosen to dedicate their careers for you, your founder, your vision, your mission, make sure that they know how grateful.

So you talked earlier about the traits in employees that make great teams create magic. What are some of the dynamics between co founders when you look at those teams that also create magic within a startup from a co founder relationship?

Yeah, I've advised a lot of companies and then I've been a co founder now three times and have always, for me, always done it as part of a team. Well, actually now a fund, which would be the fourth one as a team as well. So I don't know how to do something, not as part of a team. I think it's super important where nobody's good at everything. And it's so important to know what are your superpowers, what are you good at, what do you enjoy doing? And answer that question for your co founders. Or your early team members. And so one of the reasons guilt worked really well, for example, and all my partnerships, I think because there was clarity, it was just obvious who does what and who's in charge of like at Guild in the you know, one of my best friends then she still is. She was the she was she was in charge.

Kevin Ryan was our and for the day to day decision making, I mean, we were very collaborative. We were a small team, but Alexis was the CEO. We had two engineers. They knew what they had to do. My number one role was to get inventory and then the building the consumer audience. Alexis and I shared that. We didn't have a CMO for a long time.

So there's accountability and ownership and there's.

No questions about I've definitely seen some examples where you have, like, co founders, co CEOs, but I think that would be really hard. Unless it's so clear what that means, that one CEO maybe is forward facing and the other one's operational, or however they're going to divide it, which is.

Sort of a COO.

I know. So then why do you call it Ego? Why does it have to be two CEO? I just think it's a little OD. I haven't actually seen it kind of a company that we've seriously dug into for clarity. I haven't seen that dynamic yet, but if I do, you can be sure I will ask a lot of questions.

So are you guys looking at a specific vertical?

We're really open minded, so across consumers. So we would look at something in beauty, in pet food and beverage. We've made three investments so far. So the first one was in a company called Dormify. So everything related to the dorm or college experience that you can imagine and that's predominantly ecommerce and a mother daughter founder team. We love them. The second business is a fintech B to B play called Union. So actually in your world, Brian, a little in the hospitality, it's an inventory management system as well as an ordering platform where consumers in high volume hospitality can order drinks and food through QR codes and on an app.

And spirits companies, food and drink companies can market directly to the consumer through the app. So totally different. I get to do a lot of B to B thinking for them. And then the most recent investment was a company called CleanCo, which is a non alcoholic spirits company. So that's a big trend in health and wellness, which we like overall. So you have a non ALK, tequila, gin, vodka and rum version. So that's a lot of fun. Check it out.

Clean co that's awesome. And then as we just wrap up here, I want to talk a little bit about Miami, right? Like you'd started your companies in New York and now you're down here in here. Have you been here for a little while or.

What was the story? So my mom is Cuban my entire life. I would come since I was a baby to Miami, specifically to Biscayne, which has always been my happy place. But I grew up in New York City, so as a young girl went to school in, you know, now I'm married with two children. We were raising our kids in New York, and we would come to Miami to Kibiskane to play for vacation. And when the pandemic started, my husband and I just reevaluated a lot of things in our lives and what we wanted and the world now Zoom enabled, made it possible for both of us to do our careers from and you.

Want to stay here?

Absolutely.

Yeah.

Definitely want to stay here. No, I'm really bullish on Miami. I think amazing people are moving here and getting involved and supporting many aspects of the city. For example, I'm on the board of the Paris Art Museum. The Pam really involved in kind of tech and entrepreneurship here. It's exciting. And I think Web Three and crypto are definitely making a foothold in Miami. And I think part of it maybe being the warm weather, the Latin undertones, everyone is very welcoming, friendly people, love introducing newcomers to the old timers and lots of tech happy hours, which I think is awesome.

And Latin food. Oh, yes, that's one of my know. I'm born and raised in Puerto Rico, and I didn't have much of that in Denver or in Austin. Oh, my God, I have a Cuban restaurant literally right below my Apartmentas all day.

Well, anyway, Alexandra, just want to thank you for joining us on DTC Pod. And for our listeners who might be listening in, where can they find you and connect with you? Are you on Twitter? LinkedIn. Like, where's the best place to follow?

Yeah, all of the above. LinkedIn, for sure. Love it. Instagram Twitter. And my name is Alexandra Wilkes Wilson. I know it's a mouthful, but if you type it all in there, you'll.

Find we'll link you.

So thank you so much for coming on the Pod. We had a great time.

Thank you.

Thanks for having me.