jeff lee is the co-founder and ceo of dibs beauty, the makeup brand built for women in all 50 states, not just new york and la. he joins sean to trace the road from corporate law to running a-rod corp, including two seasons in alex rodriguez's ear producing sunday night baseball. he gets into visiting an ulta beauty in every state, working retail shifts to stay close to a customer he isn't, making 15 to 25 decisions a day, and bringing the team back to the office. plus how he hires with case studies, why he deletes his own job every year, and how ai is separating talent. for 10% off dibs beauty, use code READRECEIPT.
In this episode of Read Receipt, Sean sits down with Jeff Lee, co-founder and CEO of DIBS Beauty, the makeup brand that promises it will never be the brand that says "beautiful before, beautiful after," and builds for women in all 50 states, not just the coasts.
Jeff traces his path from Stanford, Yale Law and corporate law to running A-Rod Corp as COO, where he says he learned how to be a CEO from Alex Rodriguez and spent two seasons producing Sunday Night Baseball from the seat next to him. He gets into the gap DIBS filled, visiting an Ulta Beauty in every state, and working the retail floor because, as he puts it, he is not the customer.
He also digs into the CEO job itself: 15 to 25 decisions a day, hiring with case studies instead of rehearsed interview answers, bringing the team back to the office, and deleting his own job every year. Plus how AI is separating talent, and what happens to critical thinking for the next generation.
For 10% off DIBS Beauty, use code READRECEIPT.
Jeff Lee: At your fingertips. And so a sea of sameness and, and of asking and low effort thinking. You're just gonna be dumber than ever. Sorry, it's not very politically correct.
Sean: I am super excited to have you back for another episode of Read Receipt. It's a deep dive into the how and why of the brands we love and the creatives behind them, from blueprints to launch day, customers as community, and the detours in between. Big lessons and easy listening. Read Receipt is hosted by Antidote, the email and SMS marketing agency by people who hate boring emails.
Jeff Lee: We say that DIBS will never be the brand that says beautiful before, beautiful after. Because the fact is you buy our stuff to make yourself feel more beautiful. And from there I then was like, "Okay, it's time for me to really, really focus on beauty beauty," and I met my co-founder Courtney Shields, and the rest is history. Full-time is close to 30 and, you know, over 100 on our part-time and retail sales force, right?
Sean: Um, so you're, you're in New York. What, what brought you to New York originally?
Jeff Lee: I think I'm wired that way. I think Californians tend to be of two kinds. Like one is like they get the curious itch, and then they go out east, and then they come straight back for the rest of their lives. And others are just like, "No, I'm constitutionally incapable of being in California for the long term." Like I, I'll definitely go back to California to retire, but I think the way I walk, the way I talk, all of it, I have a little bit of vocal fry, I think. But other than that, I'm New York. New York energy.
Sean: Did you, um... I think I saw that you went to Stanford, so-
Jeff Lee: Yes, twice.
Sean: Yeah. Yeah. I think, I, uh... Yeah, what, what was your background before launching the brand?
Jeff Lee: Yeah. So I was a corporate lawyer, actually. So I went to Stanford for my undergrad in international relations. I'm very interested in politics, actually nuclear disarmament, um- Mm or armament, depending on your perspective. Then went to law school at Yale, and immediately after went into a corporate law career for actually quite some time. I was in law for six years. Decided I w- really wanted to focus on being in beauty, which was like my, my real passion in life. Went back to Stanford, got my MBA, met A-Rod as I was graduating. Um, he was with Jennifer Lopez at the time. And just we had a mutual friend, a lecturer at Stanford named Allison Kluger. Um, you know, she connected us and she said, "Jeff, A-Rod would love to meet you. And, like, there's not necessarily a job opportunity, but, you know, he's interested in someone with a strong comms and strategic background." I was like, "Who?" And I actually, like, deferred the meeting for a couple weeks so I could do my research on him. And then, uh, you know, I said, "Hey, I don't even know why we're meeting, but, like, this is what I think your current public persona is like and where you can take your career next." And he goes, "Well, you know, what do you currently do?" I said, "I'm trying to start a men's skincare line." He starts cracking up and he goes, "Well, if you work with me, you'll be able to work with Jennifer as well, and we are very heavily invested in beauty." And that's what got me there. I was their COO for three years, uh, two years of... And then an extra year as president of A-Rod Productions.
Sean: And A-Rod's company was doing investments. It's like a venture, venture firm?
Jeff Lee: Yeah. So A-Rod Corp is a combination of real estate, venture investments in a whole bunch of joint ventures. At the time, he did a lot with both Jennifer and himself. We invested in Hims & Hers. I actually helped work on his own men's makeup line with him. Um, and then we did quite a bit with her many ventures in beauty as well. So there was just a lot of crossing-
Sean: Wow. Incredible. Um, what was it like for you getting to work with so many different brands in different spaces?
Jeff Lee: Yeah, I mean, I think you see some commonalities, right? Um, really great brands are kind of built on-- It's not always-- As a founder, I'm actually biased against, like, the founder mythology. I think that can be really overrated. Um, they're built on teams, right? And so y- you can pretty much suss out very quickly beyond, like, the opening pitch and, like, the mythology and the persona and, like, the charisma of a founder, like, is that second layer of people making the brand happen for real, right? Are they substantive? Are they knowledgeable? Are they competent? Are they, you know, able to push the ball forward, um, in the real ways that aren't very sexy in the pitch meetings? And you-- When you're in that world where everyone wants a celebrity's involvement, like, you're, you're a hot commodity, like, your investment is valued not for the money but for the association, you have to be able to spot that
Sean: Do you feel like that is like a natural gift of yours? Um, yeah. How did you, how did you learn to, to kind of spot that? Or was it just over time that you started noticing the, the trend in maybe the investments or pitches that were coming your way that you didn't end up moving forward
Jeff Lee: with? Like, there's pattern recognition. One thing that I'm really good at is I'm able to do my homework really quickly, right? And, um, you know, like sometimes you have no opportunity. I literally have my phone open while I'm sitting down with someone I have-- we literally have met for the first time five seconds ago, furiously texting 14 people or looking through the Google, um, search results, right? Triangulating, is this someone we should be meeting with or not? And there have been times where I've terminate- I've, like, basically said, "No, let's end this meeting now. It's, there's nothing here." Um, and others where... You know, I t- I also try not to be Mr. No, right, in that position. Um, and it's very interesting now as a CEO to have the team members who advise me, you know, in their respective roles, um, and to kind of see it from their perspective. Because I'm a lawyer, it's really easy to shut out anything I veto as, "Oh, you- he's just super cautious," right? And, like, really creative investors and, and that's what A-Rod is, that's what a lot of people are in this space, are really truly focused on the exciting, and it can be really tough, right, to have somebody constantly be like, "No." And, and your focus isn't on just being no, but rather, like, this is why or this is, there's a better path forward or being creative about it. And that, I think, is a skill that a lot of lawyers lack.
Sean: And were you identifying and, um, evaluating all new deals for them?
Jeff Lee: There's a lot of inflow. Yeah. I
Sean: could only imagine.
Jeff Lee: Yeah, especially, you know, at the time when, you know, both of their careers were at extremely high level prominence, right? Like you had two plus two equals 1,000 there. Um, the kind of opportunities that are opened are, are almost inconceivable, right? Like everyone from heads of state, and you have a direct line to the head of every major bank or private and, um, equity firm to startups that have one person and an idea are coming at you.
Sean: Wow, that is so crazy to think about, uh, the access level.
Jeff Lee: Yeah. Yeah. But like at the same time, I would also say, you know, uh, after a while, right, it's, it's about the substance, right? And this is something I do admire about working with people like Alex Rodriguez, who has tremendous history, right, in substance. Um, he's actually one of the most intellectually curious people I've ever met or worked with, right? And I would never work with someone that I didn't deem to be intellectually curious. So the ability to really suss out whether there is a there there, and whether it's of interest to you from a financial or an entertainment purpose or whatever, it is pretty rare. Um, you're not just saying yes to everything that looks cool or fun or lucrative. You're saying yes to the things that are worthy of your time and where you're at. And I, I would say like, you know, he's, he's also a master at building great teams, which is something I learned from him. I, I like to always say I learned how to be a CEO from Alex Rodriguez, and, um, I think that still holds true today.
Sean: What, what, uh, what about him did you feel like was special in terms of building teams? Did he just have a knack for spotting interesting talent that other people would overlook? I guess like team sports.
Jeff Lee: Team sports. Yeah. You know, you know, team sports versus, for example, being a solo performer, right? And so I think that that's one of the things that, you know-- And I, I'm a big believer that kids should play sports because I didn't as a kid, right? And I watch how my sister raises her children, and team sports are really huge for them. Um, I think when you have that DNA and appreciation, it bleeds over into how you run your business, of course. But, uh, at the same time, um, there's a willingness, right, for example, to take somebody who barely knew who he was, right, maybe heard of him once or twice, and have him come in. I actually produced for two years, two full seasons of Sunday Night Baseball with him, where I was sitting-- I would sit next to him in the booth every Sunday, no matter where we were, St. Louis, Seattle, or Yankee Stadium, and I had the mic and I was in his ear. And at three or four games in, the producers go to him, they're like, "Okay, like, no offense, man, but why would you have this guy telling you what to say," right? And stuff. Right? And, and, and trust me, no offense, I was about like 85% sure when I met him that they ran counterclockwise on the field, right? And he goes, "Do you think I have Jeff here to teach me about baseball? I know, like everything I need to know about baseball is up here," right? "I have him here so I can help explain this sport to people like him," right? Because the single biggest challenge that you, ESPN, and the MLB face as a whole is growing your audience, right? Out of all of the major sports, you have the most stagnant customer and viewer base. And I mean, that put an end to it. And also, again, you have to do your homework really rapidly. I mean, there's so much BTS footage that the stations even have of-- I would follow him into the bathroom and we would print out gigantic score, like, like cards showing all of the players, 'cause you don't know the starting lineups until basically right before the game starts. There's a million players in reserve, and a whole bunch of them have crazy names. And sometimes I would be like-- And some of them have come from total obscurity, like, like barely, you know, um, ever seen this person in the major leagues before, right? So I'm like listening to minor league broadcasts sometimes on YouTube, trying to figure out the right pronunciation for this person's name, following him into the bathroom, and then reading the whole roster down at him and having him read it back to me to make sure he got the name right. And that's the kind of perfectionist that he is, right? And that's something that mattered to him enormously because When you're that public, you're under a lot of scrutiny.
Sean: That's incredible. Were you-- You were doing, like, the background homework on stats and feeding him-
Jeff Lee: Yeah ...
Sean: information?
Jeff Lee: Yeah. I learned what a review was really fast. I mean, a war, all that. Yeah. I mean, I, I have, like, all this footage of me, and you could even see a sense when the camera pan over me scribbling furiously, like, you know, crossing out a number here and there. He was intensely interested in the biographies of each player, so, you know, we had to have that, what the wife's name was, you know, if they were married, if they had kids, where they, he went to school. If this guy has something interesting going on in the background, you know, for him, that, those were the things that were key to making a compelling broadcast.
Sean: Did you see others in the broadcasting space do this or no?
Jeff Lee: No. No. Uh, I mean, there's a team of, um, stats, um, rabbis that, you know, are really amazing at what they do that service the entire group. But, you know, he wanted to bring a very different perspective, and I, I think that that's great because you could talk all day about when I was a Yankee or when I was a Mariner or when I was a Texan and I did this and that, and this is what they're feeling. Great, but I think he really also wanted to bring an informed approach to s- um, sports broadcasting. It's also why he's such a great analyst. I mean, he's still on Fox and has won multiple Emmys for it. So, um, this was the same, for example, when we would go on Shark Tank, and the guy does his homework, right? I mean, uh, that's something very commendable about that.
Sean: Yeah. I also feel like it's interesting to invest in areas like that that other people don't, and you can obviously see it. Like, uh, you know, I feel like that's interesting though to go into, like, a new job basically, and then almost do, like, the opposite of what the tenured people who know what they're doing are-- is, like, standard looks weird. And to be comfortable-
Jeff Lee: It has the permission structure, I will say, right? Like, you have- Obviously, yeah if you are, like, one of the greatest athletes of your sport- You could do
Sean: whatever ...
Jeff Lee: so yeah, you, you got more permission structure than the average person, but there's a lesson in there for all of us, for sure.
Sean: Yeah. Did you always know that you were gonna move on from that and launch something on your own?
Jeff Lee: Yeah. I mean, I think launching something on your own is something a lot of people that go to Stanford in particular, 'cause it's a school that really prioritizes entrepreneurship, um, have. But I actually- Didn't know for sure 'cause the path to entrepreneurship was so convoluted. And, you know, I, I do view myself as, you know, enormously adaptable, so it's been a lot of fun. It's a different set of challenges. But, um, I get very skeptical of the people that kind of draw the straight line through their entire career in a very beautiful way, 'cause you can do that in a million different ways after you've lived it, right? Like at the time, I didn't know what I was doing, and I was waiting for the opportunity to fall into my lap. And by waiting, I meant knocking on 8 million doors, but I couldn't have played it out the way it did. And there are a million times when I look back where it could have been that I never did this, or that I went and did this 10 years earlier.
Sean: Yeah. Did you-- So, so you didn't necessarily know you were gonna launch your own thing. Were there, were there aspects of businesses that you were getting exposed to that you, that you knew you liked and wanted, uh, would want in a venture if you did end up doing something? And what, what would you look for back then?
Jeff Lee: I think consumer mattered a lot to me because, like, that's something I have deep resonance for and, and that was a reason why I left Wachtell, was that I found that my consumer goods clients were the most interesting, and retail also. Um, I represented Sears, actually, in many of their final transactions as, you know, the business was being pulled apart and reshaped and, and some parts of it were kind of meeting their end. And I, uh, I think fundamentally the thing that drives me to this day, even in the DIBS business, is consumer mentality and consumer mindset is really fascinating to try to unlock. Um, and that's the aspect of this business that is interesting. A lot of these businesses are not-- CPG businesses to me are not structurally that complex, right? Like the supply chain, right? Performance marketing, great. You know, uh, whatever your, um, channel is, your retail partnerships, et cetera. You put those together and they're all mappable in some way, shape, or form. But what you're trying to solve for constantly is changes or getting ahead of the changes in consumer behavior. And that is what makes what we do so interesting. Like we just finished, not even an hour, but we just had a product development meeting here with my co-founder, Courtney, and our team, and it was two and a half hours like, you know, really racking our brains for what does the data tell us about where the industry is headed, about a category we're entering? But at the same time, what are our brand principles? What do we know about the existing customer? And when the two are in complete tension with one another, what's the right solution? Understanding that this is a product coming out in 15 months. Where do we think the bar is going to be? Where do we think the customer's gonna be, and which channels it's gonna play on 'cause we have a different approach for all of them. And that's a-- Those are the pieces that are really fun 'cause there's a lot of psychology that goes into any consumer business, whether you're selling VMS or, you know, cosmetics.
Sean: What was the initial gap and, and where was the ball headed when you guys were working on the brand, and what was the, the vision for filling it?
Jeff Lee: It's very easy, which is the idea that makeup had become ma- this was the pandemic, so people had stopped wearing makeup in a lot of ways. But there's a belief always that makeup will come back, that it's a cycle. For me, I'm-- I firmly believe that people can say the end of beauty all they want, but some of the earliest objects that we find in the archera- archaeological record was in pr- predynast- predynastic Egypt. They opened the tombs and they found two things. Well, one, uh, makeup. So people have been obsessed with makeup since 3000 BCE. And they also found, by the way, like some evidence that they may have killed the early pharaohs who couldn't finish a marathon on their fir- 40th birthday. So we have, as a species, also been quite obsessed with physical fitness, and, uh, both of these things are highly relevant today in consumer. Uh, so I would say at the time, the single biggest obvious gap was that there were no beauty brands speaking to women that wanted makeup but also did not wanna go all the way into an artistry level 20-step program, and also, uh, th- were not interested in the no makeup makeup, like very clean com- cosmopolitan look. And that ties into our customer base, which is what I think makes us so unique, which is I always say every day we are a 50-state brand. So Courtney, my co-founder, had built this incredible influencer fandom of women across the country. But she lives in Austin, Texas, which I just arrived from, and her base is heavily Texas, in the middle of the country, in the South, you know? And that's a really powerful customer who is totally unaddressed by all the makeup artist brands in New York and LA, and that's really been foundational to everything we do. Um, I'm very proud, like we're, I believe, the only makeup brand that has activated in Indiana three times. You know, in our five years of existence, three times we've gone to Indiana. We go to Nashville every year. We do Texas like every quarter. Um, I'm the only founder who has gone to all 50 states actually to visit an Ulta Beauty with my brand. And so from Alaska and Alabama to West Virginia and Wyoming, I have in the last two years gone to every single state in the union. Um, and that's something that people know about our brand, is that they will very likely see a founder in Idaho or Wyoming or a Dakota. Um, and we pay a lot of attention to that regional customer even more than any other brand, I would argue, out there does.
Sean: I saw you-- I saw on your Instagram you at the Ulta- Event
Jeff Lee: Yes. All thousands.
Sean: Yeah. And I, I was thinking like, wow, so tapped into the energy of uh, a retail partner, like I think it's one thing for people to go, but like the way that you were interacting with people and drawing, like, drawing people into the, the brand and what you're interested in, I could tell, like, how connected you are to that team and also just to, like, the brand and how it shows up to people in retail, but also who's working on the retail floor.
Jeff Lee: 'Cause that- I mean, they can tell, they can tell. That's what they tell me, right, is that they can tell when a founder is genuine. And, you know, I get a lot of energy from it for sure, and I'm very proud to be a CEO that knows every team member of ours. Every freelancer I try to meet as well when I'm in store. And, um, I will work the retail shift at times. On weekends, I will go in when I have time and do the eight hours with my team and like, you know, clock in, clock out, and sell on the floor. Um, it's very important because I'm not our customer, right? And one of the things that is so important in, uh, for us as a brand is to always stay close to the customer. And we've had people that were unable, for example, to separate their own preferences, desires, and, you know, predilections from what our customer wants. And it helps actually in my mind, I think, to... On the one hand, I have the expertise. I know what beauty is. I know what good beauty is. I know what great formulation, what great products are. But I'm also not using most anything that we make. So I'm not making anything to my personal preference. I'm instead obsessing all the time about what a woman sitting in Nebraska that I've met wants from our brand, and what she wants in life in general, right? So I'm stalking her Instagram if I, you know, haven't talked to her in person. I'm looking at who she's following, what she's commenting on, and then I'm generally making business decisions out from that information.
Sean: What initially started your, uh, interest in beauty?
Jeff Lee: Yeah. I think it's, uh, really hard to pin down. I mean, I'm also a beauty pageant coach, as you may know. I'm one of the best in the world, so for 20 years I've coached Miss Universe winners and, um, you know, at my level it's... And, and I do this entirely pro bono and it, and, and it's on my schedule, right? Which allows me to tell the countries that come to me, "You will fit my schedule and my work schedule and my personal life schedule because I'm doing this because I believe in your candidate and what she represents." So I was a kid and I watched the Miss Universe pageant, and for me it was like the Olympics except about beauty, and I thought it was kinda crazy and cool that people could compete on this basis. And here in the US obviously we look at pageants and it's like Toddlers and Tiaras and just really kind of gross and weird. Um, but elsewhere in the world- Well, this is a national sport. Um, eight Venezuelan Miss Universes, like, you know, have gone on to major careers. One ran for president, some are governors. A dear friend of mine was the first, um, Black congresswoman in Colombia after she won Miss Colombia. They have a postage stamp in her honor. And, um, yeah, like, like these titles are taken the same way that a country approaches an Olympic gold medalist or a World Cup winner. But I do think that on top of, like, loving this competition and everything about beauty that flows from it, you basically have to be of the mindset of there's something about what you're doing that fundamentally you enjoy and are grav- like, gravitate to you, and you don't need any more explanation. Um, one thing I'm pretty unapologetic about is that we work in beauty, right? Like, like, like there's so much political correctness around the phraseology of the categories and all of it, and like, at the end of the day, I always say, look, I am somebody who-- uh, my thesis in college was how do we elect more women to presidencies in Latin America? I actually teach the first session of a Chicago Booth class every year about how we advance more women to CEO roles and positions of corporate leadership. But at the same time, what does every woman want to be on her wedding day? Well-spoken? Like, you know, charismatic? No, she wants to be beautiful, right? Like, like, he- right? Like, that, that is what she wants, right? Why does she w- spend so much on the photographer and on the makeup artist and on the hair, et cetera? 'Cause she wants to be beautiful, right? And there's nothing in my mind wrong with that because that is something that we are coded for, and as long as you approach it in a healthy way, and, and how you define that is also open to debate. But, uh, I take the view of if we're selling you $30 blush and bronzer sticks that make you feel more confident about yourself, put yourself in a great mood, then we're doing the world a service.
Sean: What do you, what do you view as your core, core jobs as CEO learning from, from A-Rod and now applying it in your own
Jeff Lee: Yeah, I mean, I, I have a lot more sympathy for him now sometimes. Like, I, I was telling him, like, the other day, I was like, "Damn, Alex," you know. Um, I... And it's funny 'cause there was a documentary that came out recently called Alex vs. A-Rod, right? And it's kind of crazy 'cause I really call him Alex, right? Like, and so, um, I used to joke that I would call him A-Rod in the third person because it was a persona, and it, it became the, the whole basis of this documentary how there are two kind of identities for this guy. But I told him, I said, "Alex," you know, "God," you know, "there were so many times I was so frustrated with you, like, because, okay, like the direction wasn't clear or, you know, so, so." I'm like, now I totally realize, like, I'm that person in my seat, and my team has every right to be frustrated with me. I think you need to have a really, really clear idea of your vision and where you're going and where the company is going. You also need to obviously make really, really tough decisions very quickly. Um, it's your job, right, to create the best possible team. So that means making really tough decisions and also being a great recruiter as well, right? And also possibly helping shape the skill sets that make somebody better or, um, at their job, right, that they might not have had before. Um, and then the other, uh, really key item is ultimately you have to make a lot of decisions, and you have to make them really quickly. One thing I'm very proud of is that I am known, I believe from my 360s here on the org, as being very decisive, right? Um, the worst thing is to not have a decision. And I really subscribe to the philosophy, right, of what the math is 50% plus one of your decisions have to be right as CEO. Like, you have to make sure the big ones are part of that 50% plus one. But every day, right, I would say I average about 15 to 25 decisions on top of the things I have to do, and there's no time to second guess a lot of them. I would rather do and be wrong and then do so- do it differently or retool than not do, and that's something I learned.
Sean: Are you naturally gifted in moving quickly? It seems like.
Jeff Lee: Yeah, I'm deeply impatient. I think deeply impatient people move fast, and they expect that from their teams, and so that's a, a key piece of it, right? Um, and I, I, you know, I really respect actually the Ulta CEO, um, Kecia Steelman, right? And she is known for being- I, I love the sentence that was said about her by one of her execs, which was in a very complimentary way, "Kecia is not a patient woman. If it works, it works amazingly well. If it doesn't work, she will pivot so quickly." Um, you don't in this day and age. No company operates in any sphere where they can afford to do things the same way that they were being done a quarter ago. I don't care if you're in SaaS, I don't care if you are in, you know, fertilizer manufacturing. Like, there is some kind of disruption happening or the pace of your business environment is shifting so quickly that if you are holding to the same strategy every quarter, you're asking to go the way of the dinosaur.
Sean: Are you-- It sounds like you do, you're doing a lot. Do you think that helps you in terms of moving quickly and making decisions and seeing patterns? Like, um, in the coaching, in, uh, I, I feel like you have your hands, even though you are running the business, you have your hands in many interests and projects.
Jeff Lee: Yeah, uh, but I can, you know, really zero in and out, right? Like, for example, this year has been all about, like, truly been, I mean, 24/7 of DIBS at times. And it's, like, almost to the point where I need a side hobby, and I do have one, which is gardening. Like, I actually garden a lot. So, um, even 10 minutes outside has really helped alleviate, like, the constant sh- um... I think that pattern recognition is a key skill that obviously we as a species have mastered, but it can be really, really tough if you start to pattern recognize yourself into the same routines over and over again. And that's something that we see a lot in beauty. Like, people love to calibrate against what's been successful before. Playbook to get from zero to 25, 25 to 50, 50 to 100, 100 and beyond has been ripped up a million times in the last five years for us.
Sean: I might, uh, this might sound like a dumb question, but, um, you talked about routine and not getting wrapped up too much in the same routine for pattern recognition. How do you, uh, how do you push yourself to keep, like, visiting the 50 states? Uh, you know, like getting out into the world, moving, taking in information while working on big projects, running a team. Is that, like, something that you have to push yourself to do? Is that something that you've always kind of been doing? I kn- m- you mentioned with, uh, Alex going to all the different cities to do broadcasts, maybe that's part of, like, the training to keep m- moving. Basically,
Jeff Lee: yeah. Yeah. I mean-
Sean: Yeah ...
Jeff Lee: you-- That's a skill. Some people travel well and some people travel poorly, right? Like, our retail team, for example, are incredibly good at traveling. Like, like they are so efficient. There's s- like we had a, a brand manager in the early departs of, uh, early days of the brand who knew everything about, like, how an airport worked, right? Like, you know, you could trust this woman, Monica, that like, you know, if she would be like, "No, the flight's gonna be canceled. We, we need to get you to Philly airport now," right? But the point of it is there are some people who travel well, some people who don't. I travel really well, right? And so that's a piece where, um, having that is so fundamental to doing what I do. Like, brand builders are required to travel. You cannot, in this industry, not show up, right? It's not just, "Oh, I decided to go to all 50 states." There are a million rooms that you need to be in that you cannot delegate out, right? And also as a CEO, like, there are times when you understand when your time is really valuable. I am very protective of my desk time, like of my office time, of my thinking time. I'm also very protective of the times when I need to allow members of my team to shine and to take the lead, right? And to negotiate the things I trust them to do. There are many of our team members who have a lot of autonomy because I just understand, like, I don't need to be in your neck of the woods. When I do come in, right, then I'll be there to serve the interests of the business, and there's also the push and pull. Early on, you're the only person working all the time, and you have to touch every part of the business. Now you have to understand, okay, when you do come in, there's different weight to it. How are you gonna apply it, like, judiciously? So there's, there's a lot back and forth. I do joke that I'm an introvert. I meet thousands of people a month, right? And like, like I-- my social battery drains really quickly, but I'm really good at hiding
Sean: You do not seem like an introvert- Yeah ... at all.
Jeff Lee: But- And there's a- a lot of us, there are a lot of us actually that are, like, really good at, like, ev- and actually go home and are like
Sean: Yeah. Yeah. I mean, I, I would consider myself an introvert, but you seem like an extreme, extreme case. It's just- Especially watch- watching the Ulta videos. Yeah. Oh my God. There's no way.
Jeff Lee: Yeah. Like, you know, like, like here's the thing, right? My default setting is literally just, like, sitting at home, right, and stuff. I think, like, people are generally shocked, right? Like if a lot of people who know me well, like, think that I'm, like, in the club and stuff, and I'm just like at home. Like, like, I hate crowded places. Like, I eat alone, and actually, I... One of the things that I used to do is I used to go to the movies alone too. Um, I had to do that when I was a big law lawyer, and I could not find any time to go see a movie. It was, like, Batman Returns or whatever. Dark Knight Rises. I wanted to see it so badly, and each time we would go, like, something at work would call at, like, 8:00 PM. So I ended up seeing it at, like, 12:30 AM at the AMC on 34th Street, and then after that, I just learned to watch movies alone.
Sean: I mean, kind of incredible, though. Having a meal alone or going to the movies alone, it's like a vacation.
Jeff Lee: It's great. I, I... Like, it's funny because I think people are... There, there's almost, like, a shame to it or something, right? People feel, like, the embarrassment. Once you do it once or twice and you're just like, "Oh, no, this is great," you know? Like, I-
Sean: Yeah.
Jeff Lee: Oh my gosh, it's amazing.
Sean: Yeah. I, uh, I don't really watch sports documentaries, but there was one that I watched recently and, uh, one of the quarterbacks in the NFL had a family and he was in a different city, and he's like, "I al- I always used to look at the people eating alone and I felt bad, and now I just... It's, like, the best thing of all time."
Jeff Lee: That's fantastic.
Sean: And he's like, "I obviously I love my family, but, like, oh my God, eating alone is so great."
Jeff Lee: And there's, like a, like, a, I think a TikTok went viral the other day of, like, some five-year-old kid who went on a cruise for, like, ins- like, like, it was just like, oh, he decided he was going to, like, on the seventh day of the cruise, like, have dinner alone and had his back facing his family and everyone, all the comments were like, "This kid is absolutely crushing the game of life."
Sean: Yeah. So early. Um, how, how do you, uh, how do you recruit great people?
Jeff Lee: You be upfront with them, right? I think like there ha- there has to be a real level of transparency around what you're offering them. Because first and foremost, right, getting them in the door is only part of the battle, right? And the battle is about putting them into the mosaic of people and the interlocking skill sets and everything that allows the team to build itself greater leverage. And you can't do that without being super upfront about what all the other people are like, who's strong where, where you expect their strengths to be, and what it's like to work with you directly if they're someone who's reporting to you. Now, I interview every FTE hire at DIBS, right? Like, like every potential candidate, and we've done a large changeover in the last quarter b- because I'm asking folks to return to office here in New York, so that's created a lot of organizational shift. A lot of-- And we're also growing as a business, so a lot of new people have come in. And no matter your level, I'm always the final interview, right? Um, I, I really believe that that's incumbent on a founder. I don't know that every C- certainly not a CEO, but on a founder, that you should be touching everyone that you recruit. I, I don't make bones about, like, what it's like to work here. We work hard, but I don't think we're unreasonably hard. But we are definitely a place where people work hard because they love what they do, right? Like, you really, really love, you view it as a privilege to work in a industry that is glamorous and beautiful and makes a product you can touch and use. And you work hard because you care, right? Like, there's a difference between punching out at 4:50 or, you know, spending an extra hour to perfect something. And the people that really ace it here spend that extra hour to learn and perfect, because the fact of the matter is that's how you get good at what you wanna do. Um, the other piece that goes into recruitment is you guys kind of understand that interviews themselves are like pageants. You're calibrating against a lot of internal biases You are calibrating against whether or not you met somebody and the tenor of their voice or their eye contact instantly made you feel confident in their ability to do a job. But as my old law firm mentor actually said to me, he's like, "Okay, if I asked you, tell me about a time where you overcame adversity at work, or what was the toughest problem that you, you know, navigated, and how did you navigate it? You're not showing me anything other than that you prepared for the interview, that you rehearsed for the question." So you have to add in a bit of a case study, no matter the size of the role, right? You have to-- A- and the case study's not gonna tell you how confident they are necessarily, but it'll tell you how they think and if they think quickly. And in every position here, you have to be able to think well, think logically, and think quickly. So there's that, that piece, which is, to me, it's more interesting to know, "I'm gonna give you $20 million of budget. These are the three things that I need you to spend it on. How are you allocating that budget? What happens if X or Y happens? How would you change your thought there? Go."
Sean: That's an incredible-
Jeff Lee: Initiative. Yeah.
Sean: Yeah. What, uh, what drove you to, to make the jump to go back in office?
Jeff Lee: Couple things. One is I think culture. Uh, people actually do wanna be around each other. I think that's super important. Number two, I think the younger team members, many of whom have perhaps never worked in an office setting before, would benefit from that time. Three is efficiency. Having to schedule Zooms or a side chat, et cetera, is crazy to me if you're all in the room. A- another CEO friend of mine said to me something that I love repurposing from her, which is, "Bad ideas take root in the corners of the Zoom." Like, a bad idea can find its way, its own life, and percolate through the organization before it reaches a decision maker, right? And, and like you're losing efficiency, time, and focus. Similarly, a good idea can quickly die on the vine if it's in the wrong corner of the Zoom. And so having people in the room can take a mediocre idea and keep it from becoming bad and take it to the next level to be a business changing strategy. And the last thing is there is a lot of interpersonal dynamics that go into the written word that people just can't handle. Like, if you don't write an exclamation mark now, halfway- ... the recipients are thinking you're mad at them. Whereas for s- others, like, they're like, "No, like, I'm just never gonna write with an exclamation mark or an emoji."
Sean: Yeah ...
Jeff Lee: a lot of meaning gets lost, right, through just Slacking each other or texting
Sean: Yeah. W- uh, knowing that you're growing at the same time, how do you make a hard decision to make a huge change like that knowing that you're gonna lose good people? Was that a quick- It wasn't
Jeff Lee: that hard
Sean: Wow, incredible.
Jeff Lee: It wasn't that hard. I was just like, "We're gonna change," and I recognize that half the company is in ano- are in other states, et cetera, and like this is happening, and obviously this is the schedule for it, which is very fast, and, you know, we will assist, you know, obviously, and, and take a lot of pride in, in making sure everyone is set up for success, whether it's with us or elsewhere, but this is fundamentally important to the company, therefore it must be done, right? And, and that was where, you know, it, it was at a place where I could see for us to reach the next level, we must see each other in person regularly. It doesn't have to be five days a week, but we have to be interacting across departments in person. And when there's a decision like that, it is the same level of thought that should go in, and commitment that should go into it as I have to go to this meeting across the country tomorrow with no notice, like it is mission critical. I'm just gonna get on the plane
Sean: Yeah. I mean, incredible. Most people have a hard time separating, uh the decision from the act of doing, though
Jeff Lee: Yeah, but you can't have a job like the one I have and have that problem, right? Like, you really can't. And you're not doing anyone a dis- a service by, by, by stretching it out, right? Like my co-founder Courtney loves to say, she's like, "You're kind," right? Not necessarily nice, because I'm also super direct, right? And, and I, I pride myself on my directness. You know exactly where you stand with your work product with me at all given times, right? You know I like it or I don't, and if I don't like it, I don't like it for X, Y, and Z areas that can be improved. And if I like it, I like it for these things that should be continued and magnified. And if there's a disagreement, we'll talk about it same day, right? Because I don't want people sitting at home wondering where they stand on something. I want them all working, you know, to the best possible outcome. And if I'm wrong, I say it right away. If I'm right, then move on, right? Um, I don't keep score. So I th- although I do sometimes, like I will say I, I, I try to sometimes calibrate against things that I maybe pattern recognized too much and made an error on. But the point of it, right, is It goes to the decision-making piece of it. The worst leaders are the ones that can't make a decision or slow down in implementing the decision, and that's, that's not a way to operate in this environment.
Sean: How do you g- how do you get your team to move at the pace that you want with a, a change like that? Do you just set the, set the date that it needs to, to happen by?
Jeff Lee: You get buy-in from all the o- other decision makers, right? 'Cause like it's not, like at the end of the day, it requires a lot of shifts across departments and leaders have to be aligned, but like as long as they, uh, understand the thinking behind it, and this is for any major business decision, right? I would argue some of the products we launch, like those are probably most mission critical. Having the buy-in is all that it takes, especially when your leadership team is comprised of fast movers and of doers as well. Then you can trust in them to make those moves really quickly
Sean: How quick do you think you know if you made a correct hire or a bad hire?
Jeff Lee: Hmm. That's a really good one. I think you know pretty within 30 days.
Sean: Yeah.
Jeff Lee: You know. Right. There's a, there's so-
Sean: I feel like you, I feel like you know within, like, three days.
Jeff Lee: Yeah. Yeah. Some people, now, some people will surprise you, and there's so many truisms, right? It's like you've never... No one has ever regretted firing somebody like, like, you know, um, too, too soon, right? Like, like, and then there's also- Yeah ... the kind of like, if they're a B player, they're a B player, they're always gonna be a B player. I actually will disagree. There are some B players that can become A players, absolutely, and then revert to B in other contexts. There are sometimes people, and you cannot have all A players, right? Organizations need B players interspersed with A from cultural element. So, and also it's a talent war. Some people just simply opt into that, and that's fine, right? As long as you're getting your work done and it's at the standard that we expect. We understand that you're here to punch in and punch out. What's more important, right, is when you think about your hiring decisions, right, and you know, whether or not they're right or wrong, et cetera, it's also remembering some people can carry the company through any number of different crises, stages, opportunities. I delete my job every year and do it differently every year. Sometimes twice in a year. I don't do the same job I do this year that I did last year or the year before or the quarter before that. Before that, I've been able to stay here. Um, and similar, same thing goes for some of my execs who've been here from, for the last three, three plus years. Others are just simply never gonna be able to be a part of that journey beyond the stop that they, you know, get off at, and that's fine, right? Like, like it's some people are gonna ride the one the entire way up Manhattan, others will come on board for a period and then get off at Times Square. Um, but you have to be confident in your ability to suss out whether they can take you to the next level.
Sean: How do you know if you're making too much change versus trusting your gut, like on changing your job? I'm assuming that you just know the time when your old job doesn't work for the new needs.
Jeff Lee: Yeah. Yeah.
Sean: And you make a decision and then change the job and your approach.
Jeff Lee: Yeah. I mean, like- Do you- ... like by job, I mean, like what I'm doing, right? Not my- Yeah, yeah, yeah ... title, right? And so look, like this has been a year where, for example, we're establishing Ulta now, right? And, um, right now, this past year, TikTok has been a major focus for me. I've spent much of my time flying to LA there, working through the strategy. I've been on a million TikTok Lives selling myself, and there will be more challenges already on the horizon. So- The, it's validated by basically, like, the fact that I don't have a counterfactual. Like, like it's anything other than, like, it's been effective at driving us through the challenges that we have in the environment. To answer your question more specifically, how do you know? You don't until you see it working, right? And if there's a question-- I think the worst thing though is you pull out of something because it's not working immediately. But you have to be very disciplined, right, about how many, how much time and money you're gonna put into a certain focus before you pivot
Sean: All right. Do you, um, who do you go to for advice on the business outside perspective?
Jeff Lee: I would say everyone should have a personal board of directors, right? And so, you know, for me, I have-- I always joke it's like a little WhatsApp group, right, of other CEO founders in the space. But there's also a cautionary piece to that, which is, yeah, it's therapeutic to hear if they're dealing with the same things that you are, but then it can become a venting board where you're just projecting your own things onto them and they are to you, and no one leaves happy or resolved or more productive. Big believer in coaching, right? Like, I'm actually a certified personal trainer, and I will go out and hire trainers who fix my form and my approach to working out every year, and they themselves have trainers, right? So having a professional, like coach or guide is super helpful. Um, and I would say-
Sean: Do you have a coach?
Jeff Lee: Mm-hmm. Yeah. It's like great to have someone that sits outside of the business, right? That, like, can just kind of help you think through discrete problems on a day-to-day and larger ones, right? Whether they're professional, interpersonal, or business related.
Sean: How do you find good coaches?
Jeff Lee: You kind of have to date them. Like, like you have to kind of go and meet with them to see their methodology, 'cause there's a personal chemistry, um, element to it. Um, but-
Sean: Are coaches- Are co- are good coaches doers?
Jeff Lee: Not necessarily, right? Because, like, you don't need them to-- There are great coaches who have done it themselves, right? That have been CEOs and major execs and know what it's like to sit in your seat and can advise you there. But then they-- sometimes they're just pattern recognizing. In my case, right, I have an academic, right, who has a PhD in, in sociology studies, right? And so I mean, maybe hasn't done this job, but has a strong didactic framework and, and a way of unpacking things that make, gives me confidence in what she's done. Similarly, on a different vein, when I coach people for Miss Universe, some of the greatest coaches are former winners, but many of them are terrible at it. Many of the former winners that go in, like they go and say, "Oh, I wanna coach future winner," they're just projecting themselves into the shoes of that. Or they're calibrating against the way the contest was run. Like, the contest itself shifts every few years of what it's looking for. If you don't have that ability, then you're, it doesn't matter that you won yourself. Like, you're not gonna be able to help someone else succeed.
Sean: Yeah, I always, uh, coaches are incredible. It's always-- I always think it's interesting to find great coaches, 'cause when you have a great coach, it's like an incredible, incredible experience. But they are hard to find.
Jeff Lee: Hard to find, yeah. Yeah. And once again, right, like different coach for a different time and, and place, right? Like that's also the thing. It has to be the right person to help you move to the next phase of your career or, or for the business. I try to keep it lean actually in terms of, of people. I really believe and do-- for our revenue size, et cetera, we're probably small and that's because I'm like, I'd rather have fewer people who are doing more, right? Able to learn more, cross over more than have a bunch of specialists. You can only do-
Sean: Uh, where do you see the biggest changes happening right now in the industry? Like in terms of how teams work together or overall
Jeff Lee: I think the ability level of people to use AI effectively is really key, even more than occ- everyone will talk about the organizational changes AI can run on your org and all of it, and I think we're very well ahead of the curve. I'm being told constantly by our investor that we are. But there's a very clear divide between the people that use AI effectively and the people who are using it almost gratuitously, and that depends on your job and your function. We have creatives who use it really effectively. Like the, it's like it does the first draft in ChatGPT, and then they're photoshopping over, and then they're adding in the real asset, and it's indistinguishable, and they've saved time. For me, that's an effective use. Similarly, on the business side, you have the people who kind of accept what Claude spits out as gospel, and then that, in a way, requires you to like train them to do an extra layer of quantitative analysis behind what they're putting in front of you. Then you have the people who can wield it really effectively to eliminate repetitive tasks or to at least provide the first layer of ef- you know, efficiency of what they're doing. Those people are really powerful. As a lawyer, right, like I'm not that great of a lawyer anymore because I don't practice, you know? Like I'm out of practice. I still do all of our contracts. It's different than being a lawyer 24/7. But having Claude on my side, like it gives me a leg up, but I would still be totally wrong if I didn't know what to look for and cross-check or how to use it in that setting. Um, and so that's where it's really separated talent. Like if you're grading on a new rubric, it's like are you able to use this to the next level, and also able to think ahead of use cases? Um, there are certain talents out there I'm looking for right now with a strong statistical ability that can use the AI tools that we have to deliver data insights that were totally unthinkable of like a year ago, right? And like that's deeply interesting to me versus everyone else just being able to ask queries and they're a little chatbot.
Sean: Yeah. Yeah. I mean, I, I also feel like the AI stuff is, um- A revealer of learning rate. Like a fast rate of learning, you can just, like, go through deep rounds of iterations on how you're doing stuff, how you're working, what it's spitting out, what you're giving it, uh, what you would prefer it comes out like. And I think when you work with AI or other people with AI, you see how quickly they learn and change behavior based on the learnings versus other people who might just get, like, frustrated with the output or trust it first time and not go through cycles like that hundreds of times. I mean, I could imagine if you had AI back when you were doing the broadcasting, it's like how many cycles of research would you go through in like a 30-minute period to feed the machine before it needs it?
Jeff Lee: Only as good, by the way, as the input's provided, so there's that piece of it too. But yeah, I-- The thing that drives me craziest about it in our world is that it's just created this never-ending cycle of sameness in a way. I joke to everyone, like I-- my, my brain just starts rotting when I read something like this. This isn't a product, it's a masterclass. This isn't X, it's Y, right? And like, so that's a very surface level irritation you have, but then you start to see in creative assets too, where you-- there's like a super repetitiveness that's happening and shitification, right, of the internet and all of it. But there's a lot of really, really cool stuff that's being done, both in like a quantitative and qua- qualitative level. And for us in beauty, the ability to tell us insights about the customer over time, that's really interesting, right? Um, again, I don't know about the predictive capability of AI. There are a million services out there that are trying to get ahead of the development curve and tell you, okay, in 2027 this color is trending. 2028, this format of blush or bronzer or lip gloss will be in based off of the AI and all of it. I don't know that I have a data set to support or-
Sean: Yeah. Interesting So interesting. Well, um, I mean, another thought comes to mind, like, the, the other thing I feel like I see is that now everyone can output something faster. So it's also like the gap between an average player and an A player. The average player can put out more work output, but you still have to like sift through it if the quality is not at the level that you want. So I think like even that affects how efficient your team can be. I think that goes back to like, I feel like teams are gonna have smaller numbers of incredibly good people, and the gap, the gap will widen between how effective an average player is and an A player, and how much they can impact the business.
Jeff Lee: I mean, it's a little scary to think about in the next generation because-
Sean: I know ...
Jeff Lee: as that gap widens, right, y- you're getting people that move to the top because they had the training early on, and whether in education or through their own self-improvement, to be able to rise to that level. They didn't derive it from the shared AI s- you know, um, landscape that we're operating in. If you're coming up through school now, right, but like, you know, like when knowledge is handed to you in that way, right, in, in such a commodified way and your brain isn't forced to process and find, like, you know, to think critically, how will you ever gain that kind of level of second order analysis or, um, intelligence even to operate the system? And that's the scary piece, 'cause that stuff I think is not, to get really deep on a podcast about beauty entrepreneurship, right? Like that level a lot, like, uh, it's not biological, right? Like I don't think it's gen- I think it's trained. Same way, right? Like, I mean, I started studying for the SATs at age nine. I started studying for the LSAT when I was a college freshman at 16, right? And- It train-- like those tests train my brain in a certain way. Like people like crap on standardized testing all the time. I'm a big believer in it, right? Because it does force your brain to operate in very uncomfortable ways that are deeply helpful later on. In the same way that law school is so proud of training you to think critically in a certain way. Like some of that's overrated, but there's a lot of value in the way that your mind is ordered. And like you never get that anymore because your whole education's been replaced by you just asking questions, um, to whatever's next after ChatGPT. Yikes.
Sean: Yeah. It is also like the lack of difficulty or like uncomfortableness is odd for sure. And I don't think you can replace that. Like I, I think the impatience and bouncing around that comes from that is... I, I do miss that about like pre-AI world too, you know? Um, I have, I have been curious, like I wonder what it would be like if you had a company that fully rejected working with any AI next to everyone working so hard to implement it. I guess that's already happening, uh, probably. But, um, I mean like if you had people who are interested in it and as capable and they decided like, we're not gonna, we're not gonna take part in it. We're gonna be super focused and do things in a, a manual way that forces your brain to think critically about everything. Like I wonder what the, the outcome would be outside of all of like the automation aspects of things.
Jeff Lee: Depends on your industry
Sean: I know
Jeff Lee: Right? Right.
Sean: I-
Jeff Lee: Like, like there are a lot of creative, I think consumer industries where that company might be the lone survivor. Um, because right, like if when everything else is in the ca- uncanny valley, like... Look, you know, we're not complicated. We're marketing machines selling things that are based off of emotion and opinion and, like, you know, your ability to calibrate what the customer reacts to is deeply emotional and can never, in my mind, be fully automated at the same success rate as, you know, humans doing it themselves. But if you're in software, yeah, I don't know. I mean, I, I think you might be screwed, for lack of a better word. I think you already are in some ways, right, if you haven't fully adopted it. But, um, in more quantitative fields, it's hard to say. But, you know, if you think about it this way, right, human intelligence has always been forced to morph itself into different ways, right? We were hunter-gatherers then, you know, we were focused highly on construction, irrigation, stone masonry. Then now, you know, then we enter like the Industrial Revolution, and now we're all white collar workers at the top of the ec- those of us who are lucky enough, present company included, to sit at that part of the economic chain. The skills that have been valued by society have changed dramatically. So if being a human computer, which is a mathematician or, you know, a quant, or being a human dictionary, which is like a securities lawyer, is no longer valued in society, it's gonna be a different set of skills in the next generation.
Sean: Yeah. I have, I have, uh, young kids, so it is a wild thing to think about. I mean, you honestly can't go down that rabbit hole too much with not knowing what is gonna unfold. Um, thank you for hanging out. I loved- Sure ... talking, uh, and learning from you. I need to, I need to find coaches.
Jeff Lee: I, I do believe in it. I really believe in it. It can be humbling and everything, but look, life is nothing if not self-improvement, right? So, um, that's the most- Yeah ... exciting part of life, right? So.
Sean: Well, I have, I have coaches, but right now I have a coach in, uh, jujitsu and a martial art, so which is so, so helpful in and of itself. But, uh, I've always loved the idea of getting coaches in multiple areas of life.
Jeff Lee: Absolutely. Y- I mean, and again, right, sometimes they're fantastic, other times it might be blind leading the blind, but you never know until you actually experiment and go out and search for it. Yeah.
Sean: Well, thank you again. I will-
Jeff Lee: Pleasure, Sean.
Sean: Read Receipt.