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March 23, 2023

From a 10-Figure Aviation Business to eComm Agency Owner with Lolita Petrossov — EP 018

Episode 18
Lolita Petrossov

Ten Years In The Making is a weekly podcast on how to effectively grow a startup.     

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Adam Robinson: Lolita Petrossov, thank you for joining us. Lolita is the founder of Evestar Marketing. Did I say that right?

Lolita Petrossov: Yes, Evestar Marketing.

Adam Robinson: And was the co-founder of JetSmarter, of which I was a customer, and I really enjoyed the service and I really enjoyed watching this thing unfold that I feel like I can sort of relate to probably some of the beginning stages of it because I'm in the middle of this crazy moment where it's like all of a sudden, it is very clear that this is going to be so much bigger than it is. There is no question that that is happening. I know that you lived it and you were playing as big as you could possibly play and then there was this moment at which it's like, “Oh, sh*t,” which I want to get into also. And you had to make changes that you knew the customers were going to hate and you had to live through them, and then you ended up selling the business, and your husband apparently still works there so it wasn't a disaster. So, yeah, but first, I love the immigrant woman founder story. Half of my leadership team is women. So, can you tell us how did you get here? Childhood? And do you attribute how you got here to the fact that you're a founder?

Lolita Petrossov: Of course, it did. Well, first of all, thank you so much for having me. It's pretty incredible that JetSmarter got sold in 2018 and I got into your studio not even knowing that you're a customer but this is like the story of my life, right? I will get on the call and the people are like, "Oh, my God, JetSmarter founder. I used to be a customer.” I can't even explain to you the extent of that happening still on a daily basis and, usually, like right now I don't really talk much about it because Evestar is doing really well and I get prepared to come in to talk about Evestar. But JetSmarter, yeah, it's been, I would call it today was a cultural phenomenon as a company. To get that question of my childhood, I was born in Uzbekistan. I don't know whether most of the people even know where it's located. It's the Soviet Union country. Middle-class family. My father was a lawyer, mom a teacher. I was actually playing tennis. So, I started playing tennis at the age of seven, realized that I have this incredible talent. So, my parents started investing a lot of money in my tennis. And at about 13, there was a dream that if you want to continue playing tennis and turn pro, you got to come to Florida at Nick Bollettieri Academy, IMG Academy.

So, my family actually applied for a green card dreaming about my professional career already. I was already like about 11 years old and my father wins a green card in Las Vegas. It was just like the chance we played, we won, and it's like, what do we do? And this is how we ended up. It happened very quick. And it was a ticket to Bradenton, which is I don't know if you ever been to Bradenton. It was very small. It's like a village in Florida and the only thing that they had was this Bollettieri Academy. We immigrated in 2000. I was 13 years old. And, yeah, I remember it was just before IMG bought Nick Bollettieri Academy. So, I come in, no English. All I know is how to play tennis. My family, all-in on my tennis career. I turned pro at the age of 14, did pretty well, had some ups and downs with some sponsors. And then you kind of got an opportunity to go play for University of Florida and University of Florida, full scholarship. They were number one ranked in NCAA Division 1. So, a lot of people, athletes would get in, play for a couple of years, get education, and then turn pro. So, that's what I did but I met my husband at University of Florida in my junior year, and we fell in love and got married on campus.

Adam Robinson: Wow.

Lolita Petrossov: Yeah. I graduated in 2008, which was I think that obviously recession, the worst time to graduate. No jobs out there. And we're like talented people, very eager to start our adult life. No jobs out there. And then my husband is very entrepreneurial and we kind of had an idea to open this JetSmarter to start it. So, JetSmarter was our first job, to be honest with you, and it's an amazing experience that it took off, you know.

Adam Robinson: That is incredible that it was your first job. Was your husband an athlete also?

Lolita Petrossov: No. He was not. He always dreamed to build a big business, very smart, very wise soul. Very entrepreneurial. Studied finance. Yeah. And it was just like what do you do in 2008, right? No jobs.

Adam Robinson: Oh, yeah. It was a mess.

Lolita Petrossov: It was like circumstances but I think that he got exposed to the industry actually work for a broker, comes home, and he says, “Lolita, there's a massive opportunity.” I started working as a jet broker. They still fax the airplanes. They’re a mess. Nobody can find airplanes. And he was always very into tech and he's like, “I think that we can do something, and if we can go…” That was the time actually when we started building an app was already like it was 2011. Yeah. So, we started building it and putting some data into it and it started taking off, gave it to some friends and people were like, “Oh my God, there are some legs behind it.” So, we kind of went all in on that and then hit some challenges with the name. We had to change the name like two times. First, we were called UJet then we were called SmartJet then JetSmarter. Anyways, but it did take off because I'll tell you that that was in the time when apps were becoming popular. One thing that we did very well is that we started the company at the right place at the right time that we were the first app for private jets and we were the first company that tried to digitize the industry.

So, we came in as kind of the leader and we ran into this whole space and kind of claimed that it's ours. I think that's what happened because we understood the power of technology and that industry just was very archaic. And I know that there are other companies right now saying that they digitized that or not but we were actually the first ones.

Adam Robinson: Everybody's going to say that. I'm sure a lot of people have no idea what JetSmarter is or was. You saying it was a cultural phenomenon I think really captures it well. By the way, I worked for Lehman Brothers so 2008 resonates very deeply with me. I can't imagine graduating at that time but I have these Wall Street friends and hedge fund guys, and whatever else. Some of my very rich friends were using it, and I just assumed that it was inaccessible to me because they were almost using it as the status symbol, like, "Oh, let's go to the…” You know, it was like you'd be sitting at a dinner table and then a guy would whip out his phone and he'd be like, “Do you guys want to go to Vegas tomorrow morning? Like, we can go, like on a PJ.” And it's like, “Yeah. Actually, that sounds amazing.” And then I remember when I found out it was only like a couple of thousand dollars a month and I could fly for free from New York to Miami or Chicago. There was a time where I was like single and traveling a lot and it was like this feeling that I got of like, "Wow. I can actually fly private, too.” I understand in the status that I got, it became part of my identity, you know?

Lolita Petrossov: Exactly. Yep.

Adam Robinson: You were deliberate and, I mean, I think that in terms of creating… Say what you want about the business model, the arc, or whatever. And by the way, so how much money did you guys raise? Like a billion dollars or something?

Lolita Petrossov: No, no, no. Worth the valuation, right?

Adam Robinson: Okay. For some reason, I thought you got a billion dollars from the Saudis or something.

Lolita Petrossov: We raised close to 200. Yeah. 200 million.

Adam Robinson: Okay.

Lolita Petrossov: Yeah. So, let me explain to you what JetSmarter is. So, we start this digital brokerage and I remember the time that we had some seed funding, and my husband is brilliant. He's a marketer. All right. So, we learned how to get the airplane data into the app and people could go search for their airplane. It was all charter, right? But the charter is always for wealthy people, ultra-wealthy people that can afford to drop 30K on a flight to New York. So, we go to this big vendor, this big operator, operators who operates in airplanes, and we go to them. And airplanes are very inefficient with the way that they fly, right? There is somebody that charters an airplane let's say that you come in as a customer, you need to fly from New York to Miami, but the airplane is positioned in Philadelphia. So, they can fly Philadelphia to New York, New York to pick you up, and then you hop on an airplane and you go to New York to Miami. So, we go to this operator and we go, "We have this technology and you have a lot of waste. You have a lot of empty legs that you don't get paid for. And we're going to buy all of your trash. We're going to buy all of these empty legs right now.”

So, they looked at us and they're like, “Who are these kids? What are you talking about? Why would you want to do this?” You know, there was a lot of weird questions like, "Why do you need it?” We're like, "Listen, we're willing to pay for these empty legs, right, because they're flying empty anyway, right? So, we'll do the deal with them. We buy these empty legs, we get them into our technology. We understand how the airplanes move. And then at that point, we created a membership model and we allowed people that just like you that probably have never flown on a private jet, on chartered, to give you an opportunity to make it more accessible to go and experience the flying. So, this concept absolutely took off and it went viral because all of the friends told their friends and etcetera. At that point, also, we were attracting a lot of attention because nobody has done that before, right? So, in terms of the fund raising, everybody was willing to fund us. And, yes, and then we started looking at the data and we started evolving. What we're known for the most right now is that we actually created the, you know, we call it shuttle flights to where it's private jet flying but you sell it by seats.

Adam Robinson: I loved that.

Lolita Petrossov: And that model was the first one that we actually brought together. Our first route was New York to Miami and people just loved it because you're flying, you're saving so much time, you’re very comfortable, and things like that.

Adam Robinson: Yeah. You could take and it was from Westchester to Fort Lauderdale. So, for some people, it was just amazing who were like Florida weekenders or whatever. It was just like the greatest deal on the face of the earth. I just did it for the novelty. It's like taking a chopper from the West Side Highway to Westchester and then getting on this PJ and flying it down to Fort Lauderdale or whatever. It's like I had to get in an Uber and go to South Beach but I didn't really care because it was such a wild thing that was so inexpensive relative to what it was.

Lolita Petrossov: You know, at some time, because we have very strong tech. We obviously built it. Well, we were watching the trends and this is what I call a cultural phenomenon that our members such as yourself, they were so into it, it was such an adrenaline to them to hop and experience this flying that they were checking the app way more than they check Facebook and Instagram.

Adam Robinson: So, I want to talk about this because this is like what I think there's an amazing product lesson in here. So, there are two things that came to mind. One is when I was trying to teach myself how to be a marketer, I was watching’s content, and they have this chart that's like the before state and the after state that like helps you write copy. And it's like, how do you feel? What is your day? You know, like what the problem solves? I don't know. But then it's like, did your status change? And it's like that was an idea that I pulled on earlier but in terms of delivering an experience through a product that just is aspirational and causes dreaming like we're rebranding right now. And I want this story that I'm living right now where I rent a desk from Dave Rogenmoser, who started I've been renting it for four years. They started two years ago. They were going to sell their business and start a restaurant like I have 100 texts talking with them about what they're going to do at that time. He sent me a text. It's like first customer got the idea seven days ago. Hopefully, this is my GetEmails. GetEmails was what my business was called. It was stuck also at $267,000 a month but those are our high watermark.

I watched those f*cking guys build a unicorn in a year and then I realized it was possible for me. So, this idea that if you just keep trying, anything is possible. I want that expressed in our brand voice because it makes you feel this certain way. Now, when you said people are checking the app so much, I can tell you why because I was doing the same thing. It was just causing me to dream about places I wanted to go and I love looking at the planes. And then you did that deal with THIRDHOME and I was looking at houses everywhere that I could book for free. It was bananas. It was just like delivering, you know, I just think there's lessons for every entrepreneur in how creating aspirational brands, first of all. And you'd get this little book that you guys would send us and it's like your husband looking f*cking sweet walking out of this plane or whatever just like this life, right? I think if you're not at least shooting for that, you should be in a different game because that's exactly what you're trying to capture. I think when you get a product there, it opens up the opportunity to do all sorts of amazing things in marketing because you know you have people.

Our product is like, okay, so forms on your website will get you 2% of the traffic to emails. We'll get you 40%. It's like, of course, that's going to work and it opens up the opportunity to do all sorts of other fun stuff. But that emotional experience of consuming that app was incredible. It really was.

Lolita Petrossov: Right. You know what’s interesting is that when we started it, we were building a product. We really wanted to go and cater to people, the wealthy people that instead of them using a broker and giving them the transparency and understanding what's happening in the aviation industry, like where the airplane positions, how much they actually cost. So, that was the idea. But then at that point, right, when you get stuck and you're like, “I need more. I need more,” and this is when my husband is like, "How do I get that awareness going? I need to create a product that everybody just wants.” And this was the empty idea that really put us on a pedestal because it went viral, right? We created this virality and then we took it and we ran with it and we started innovating and creating other products. But one thing that we did have is we had really good tech and we understood the behavior of all the people that engaged with an app. And when we were looking in the stats and seeing that people are so hooked on it that they sit there days and nights, no matter when we send a push, "Hey, empty like available,” people would fill it out within seconds. And I'm like people, literally, do they just sit there and wait?

Adam Robinson: Well, It was just hitting people like me like I wasn't working that much at the time. I didn't have a girlfriend even. I was just like looking for stuff to do anywhere. And like, this was this incredible vehicle to just get me to another world. Whether it was literally just looking at the planes and the flights that were available and imagining being on them or actually booking something.

Lolita Petrossov: Another thing that's so fun also to hear that what we realized down the road is that we didn't create an aviation product. We created like a social network in the sky because people then would call and say, “I want to join because I want to meet entrepreneurs that have the free time to travel.” So, we started realizing that people are doing deals in the airplanes like big deals. Entrepreneurs sitting there. By the way, the Wi-Fi is glitchy in an airplane. Right now, it's better. So, you have nothing else to do than sit across each other, have a drink, and socialize. So, it naturally opens you up in the environment and everybody talks about the businesses and they would really build businesses like in the airplanes. And then I would hear these stories and I'm like, “Wow, right? This is what we actually created. We created this amazing network.” And, yeah, so it's very interesting.

Adam Robinson: So, back to the moment where you're like, “Holy sh*t, this is going to get a lot bigger.” Like, what metrics were indicating that?

Lolita Petrossov: First of all, there was the stickiness and the growth. We were growing like a weed but remember like initially like so we got this idea, right?

Adam Robinson: What is a weed? Is that like 100% a month? What’s a weed? What does that even mean?

Lolita Petrossov: Yeah. I mean, listen, from the founding to an exit, it was a five-year ride for us, right? So, yeah, we were at some point growing 100% over a month until obviously when you hit and then you kind of slow down. But at that initial phase when we were raising money, yeah, we were, you know, plus we were in the period of these high growth tech companies as well, the WeWork, the Uber. So, we were all on the way because we kind of got into our private aviation segment and we run with it. We were one of the first ones. So, yes, the growth, this is what people wanted, it’s that phase, and there’s lots of movies that are made right now and the companies and grow at all cost. Lots of also mistakes learned along the way. But, yes, the customers were very loyal. We were innovating, we were learning, and we were growing. But I do know that what we learned that was funny is that I’ve spoken to, I think at this point, thousands of members probably throughout in the last decade that they would express it and they say, "The product was so sticky, it was like a drug.”

Adam Robinson: Oh, yeah. I mean, this is like what I'm describing of my experience with it.

Lolita Petrossov: Right. You fly one time, you hope you never want to go fly commercial because commercial flying is just so awful, especially in the United States. It’s just so bad to why people would go. And they’re like, I’m going to go and start businesses so I can afford this because I’m never going back, right? So, we actually created lots of– we inspired a lot of young entrepreneurs as well that push them to work hard.

Adam Robinson: For sure.

Lolita Petrossov: Because this is life, yeah.

Adam Robinson: So, let’s talk about the pivot– I’m just telling you what I experience from the outside. It was an era when venture capital was funding unprofitable business models. You look at this thing, you’re like, this is too good to be true. Then there was this day of reckoning that occurred where it’s like, okay, my shuttle flight from New York to Chicago, which was free and I was doing all the time, is now $600. Then it became, well, it’s just not efficient anymore or something like that, right? It’s like, I maybe did a couple more, and then it sort of fizzled out. And then I turned around and it was sold two months later or whatever.

So, the interpretation was, well, that was a flame out. So, it had to have been euphoria on the way up, just like I can’t even believe because that’s kind of what I’m experiencing is like, I can’t believe that no one has a single bad thing to say about this. And they just tell their friends and it’s ripping through the Shopify Plus ecosystem, right? This is just a dream. And then what happened to where you’re like, we have to change the pricing of this. What led up to that?

Lolita Petrossov: So, we were going through the hypergrowth. Mistake that we did is we overspend it. And this is one of the things that I talk about a lot today. And I’m in e-commerce right now. I deal with all types of entrepreneurs. I spoke I have a cosmetic brand right now and she comes to me. She’s like, “I’m going to expand and I’m going to start introducing apparel in my cosmetics.” Why would you want to do that, right?

So, we overspent it because we were chasing this hypergrowth and there were certain routes that were not filling up because everybody kind of– the shared scheduled flights, they overshadowed the empty legs. Nobody wanted the empty legs anymore because, in empty legs, it’s like…

Adam Robinson: Yeah, you’re just sort of…

Lolita Petrossov: So, that thing came on, but we had to get an airplane, prepay for it. And we were banking on that to fill up. And there are certain routes that were not filling up and it was caused by us overspending. We overspend it. We start flying coast to coast, Europe, Middle East. It was all over the place.

Adam Robinson: Yeah. You had an Aspen flight at one point. I was going to Aspen all the time.

Lolita Petrossov: Right. It was too fast. And that’s something we want the growth to start slowing down. We needed to make sure that we started paying attention to things such as unit economics. There’s something that we want to…

Adam Robinson: So, just to be clear, it was like we’re growing so fast. We’re not even paying attention to unit economics. This is just amazing.

Lolita Petrossov: Right, because we were. We were growing. And every business kind of plateaus, right? And this is…

Adam Robinson: And by the way, I have no idea what our customer acquisition cost is. I just know that it’s so far better than any business I have ever seen before. I’m not even bothered to calculate it yet. I’m like, let’s wait until the channels prove out. And then what? So, it’s like, I get why you would. It doesn’t matter when you’re growing it like 50% a month.

Lolita Petrossov: You’re not looking at it. You’re looking at how many members can we acquire, how many– we did, right? And then the influencers came. We were the first ones to create the viral influencer campaign. So, we kind of conquered everybody. But then it’s something you mature and also the investors that come in, they’re mature. At the Ramsey, you have private equity that comes in. It changes the dynamic. And that’s what happened is they come in, they look at it, and they invest in the company. They need to exit in three to five years and they are unemotional about it. And they want you to start not growing at price at all costs, but actually, start getting more profitable. So, that’s what happens, right?

So, the more mature investors that come in, they say, “Okay, let’s see how we get to profitability and you have to figure it out with all these customers, all these airplanes and routes.” But I think that if we would have the learnings that I’ve had, but we were young, too, right? And we were in the era of grow, grow, grow, grow, and everybody’s growing and we’re growing. And if we’re growing, you know what I mean?

So, pay attention to your unit economics, get into the route, dominate before you go into another one. We knew that New York-Miami to us was super profitable. We dominated it. At some point, we would fly 10 times per day. It would always fill up. But why did we have to get into Chicago? We thought that we were going to be able to come in and kind of sell the memberships, but we kind of stumbled there. So, it was a different audience because New York-Miami is kind of the crowd that we understood very well, as well.

Yes, so the business started from maturing. This is what happens, right? You have more sophisticated investors that come in and they look at the things and they say, we go. And you start pivoting and changing the model and it happens. I call it the maturity. The company meets, too, at some point, but that’s what happened.

Adam Robinson: But making those free shuttle flights paid, like you had to know that that was going to just piss people off, right? But for you, it may have just– I don’t know.

Lolita Petrossov: No, no, no. But you do remember that we have restrictions, too. We had these tokens that people were chasing that we would not allow them to book unlimited. The tokens would restrict you into how many you would want to book. So, then people were like, why do you have the tokens because they would get so into it? We want unlimited all-you-can-eat. And this is a point where you can’t do that because there are other members as well. So, it’s maneuvering the supply and demand, right? And then trying to eventually– so what we’re trying to do, basically, if you remember, the memberships were pretty steep. They were like the smart membership we had at some point was $15,000 per year that allow to book two flights in certain rounds for free. And if you wanted to book a third flight, you had to pay for it.

So, that was already great in the head that they would because they can’t just get unlimited and take all the inventory because then we had other members complaining. They’re saying, “Listen, I’m in Zoom meetings or whatever. I’m in meetings all day long and there are people that work from home. They book up all the flights. So, yeah, trying to please it all kind of– but then what we were trying to do is we were trying to lower the membership fee to where it’d start charging for the seats to compensate for it.

Adam Robinson: Got it.

Lolita Petrossov: This is when a lot of members did not kind of notice because they were so zoned in into, hey, this is…

Adam Robinson: Yeah, I mean, that message was lost on me because I think what happened was like– I mean, whatever, it’s just my experience. One of the sales guys sold me on an extension at some point, and then, I don’t know, it’s just– I just imagined that it was a treacherous situation in that.

Lolita Petrossov: It was not easy, right? And we had to deal with, at that point, private equity. We were backed by Clearlake. They’re one of the largest private equity firms right now in the United States. And yeah, we had to make some decisions and we had to make them. Every business makes them. So, I resonate with a lot of these founders and their stories because they’ve been in those shoes.

Listen, we’ve done it. The company sold very well to Vista Global. It’s still doing well. Right now, they renamed it. Actually, my husband was one of the ones who suggested to rename JetSmarter to XO. Right now, this is what it’s called, and it’s JetSmarter technology. And we right now control all of the lift because we own airplanes. At JetSmarter, we didn’t own any airplanes. We were brokering the airplanes. So, yeah, it’s doing very well. But lots of member state, and by the way, lots of right now through– there was some media controversies as well. This is where I also learned to stay humble, stay out of the media side because the media, they love you, but then they can destroy you very quickly when they choose to…

Adam Robinson: Totally.

Lolita Petrossov: Right? So, this is one of the learnings right now that we had that whenever you’re growing something and you pay attention to your unit economics, don’t overspend and let the results do the talking, but you kind of stay out of it because the media can lift you, but they will destroy you, for whatever. And a lot of it was exaggeration, not true, falsified information. There was somebody that– and remember that video that started running that there was a member that got drunk on the airplane. Some other members filmed, then sold it to the media. It happens on every flight. It happens on commercial flights every single time. Every single time.

Claiming that we aren’t safe and this and that. We had the safest protocols. We were the only ones that had our security dogs that would sniff for all types of illegal apps and cash. We were very, very sad. We spent a lot of money on safety, but the whole story turned out that what happens on smaller airplanes, look at this passenger, was a passenger that had a little too much to drink. It was a mess. So, I think that at that point when kind of the narrative changed lots of fabrication, exaggeration, the private equity, the company maturing. So, that’s when the decisions were– we had a good offer and we decided to. So, whether the company is doing very well.

Adam Robinson: Did the PE involvement– so it’s like you got your venture guys at the early stage, the series C guys show up and they’re like, “No, no, no, no, no. This has to be done way differently. We got to act like adults here, whatever.” And then, at the same time, there’s a negative media explosion. Did they go out and get the offer and do everything?

I’ve been a part of two M&A processes. I didn’t have investors in either one of them. So, I was kind of like, my side, I’m just curious, when you have these really big hired gun investors, does that change things? Are they doing all of this? Surely, they have connections to buyers and sellers, as well as these companies.

Lolita Petrossov: Right. Well, yes, they were leading it, of course, because they came, they bought most of the company already. They had the control of the company. And when they have control of the company, they have experience. They have relationships. They understand what it’s like, as I said, that they look at it strictly from doing the right things to the shareholders. I mean, they’re the ones who are funding the business. The business needs to mature. So, they’re professional. They’re very unemotional to the noise that’s happening outside. So, that noise that was going on, they know what they got to do. But we were working with them. They were great partner to us and it was a collective effort. We agreed, right? My husband agreed.

Adam Robinson: That’s awesome.

Lolita Petrossov: But yeah, it was a rollercoaster. And we had to learn a lot about it not to pay because that noise gets into your head, right?

Adam Robinson: Well, I mean, I can imagine, especially if it’s about you.

Lolita Petrossov: Right. It gets into your head. So, at some point where you’re up and down and you reach that peak, and then people start, no matter what you do, it’s like you’re wrong. But listen, the business, we were trying to find the right business model. It was time for us to find the right business model. It was time, right? So, we had to go make changes. We didn’t do anything that was wrong. It’s just lots of members giving how emotionally were to the product. Emotional.

It created a lot of noise and I would hear conversation. The members would comment, they go, “Well, what do you mean? What do you mean, like I had to fly commercial now?” And I’m like, “Yeah, I guess so. “But I don’t want to.” “What do you mean?” “I thought I would sit over there and coach.” And I’m like, “The membership expired. You had to renew every single year, but that’s the way it is.” But these emotions, how people were so into it created a lot of...

Adam Robinson: I still think it’s what you should be shooting for. Again, it’s illuminating what’s possible in a product to me, right? I was hooked on it.

Lolita Petrossov: Everybody. You are not the only one.

Adam Robinson: Now that you’re pointing this out, the reason that I was so pissed off about when everything changed is because it’s like it got taken away from me. I couldn’t afford it.

Lolita Petrossov: That’s how they go. You got very personal. They already kind of dreamed and they felt and then they didn’t want to go back and some could not afford it at that point. And they took it very personal, like JetSmarter did this to me. What do I do? And hundreds of those situations are like that, right? And they would go and they would call and they would start making videos, falsify lots of information. So, that was all happening kind of at the same time. But listen, great learnings, they think that, the company, was that nothing happened. I remember the media, yeah, we’re going to go bankrupt, this and that. No, no, it’s still there. XO is doing very well. Vista Global is very happy.

Adam Robinson: See, that’s probably why I thought that it was a disaster because that was what– it was like that happened, and then I was one of these people who took it personally, and then the media was just pouncing.

Lolita Petrossov: Yeah, the media took it. You know what’s also interesting? Something that we could– these cultural phenomena aspect of it, members started creating WhatsApp groups, they were called JetSmarter members group and they went viral. So, imagine 200 members that met in the airplanes and they’re talking, WhatsApp groups, they’re exchanging these tokens. They’re doing their whole bargains and things like that.

So, one member that had a bad experience would immediately get into the WhatsApp group and then would start– it’s like you’re putting oil in the fire, right? So, at some point, we had 20 WhatsApp groups managed by members. We were trying to figure out who those members are, but it went viral. We could not, at some point, control the narrative, whatsoever. So, it kind of spun out of control once again, just because there was such an emotional piece to the product.

So, I don’t think like, I speak to so many entrepreneurs and I’m like, “Oh, can you create the same?” They hire, some brands hire me because of this JetSmarter story and they go, “Do the same,” and I go, “I can’t. You’re not selling private jet flights. We’re selling jeans. What can I do? I can’t.” It’s a product, but you’re not at the right place at the right– innovating and running with it. So, yeah.

Adam Robinson: I love that. So, how did that lead to Evestar?

Lolita Petrossov: That’s a very, very good story. So, 2018, when JetSmarter got acquired, husband-and-wife-operated business. Nobody needed a husband-wife anymore. So, we were the CEO and the COO. And yeah, it was time for me to go. Sometimes, I feel like I got pushed out or not, but it was time for me because listen, the company got acquired. When you were used to coming in and calling the shots, and then you have to go in and don’t do that anymore instead of the people which– I’m not that persona that could fit in the corporate world, to be honest with you. I’m a very kind of different persona. I don’t belong in a corporate role.

Yeah, so I decided to leave. And when I was leaving, a couple of my team members said, “Where are you going?” And they were from marketing because they were reporting to me. And I go, “You know what? I don’t know. I’m going to retire.” I think I said, “I think I need a minute. I need a minute because all of this focus, like I need to think about.” And they go, “Well, we’re going to go with you.” And I’m like, “Okay.”

So, they went and I had the head of growth, JetSmarter. I had a couple of people from the marketing team and they walked away. They walked away, and they had families. And I’m like, I felt responsibility over them. And I’m like, “What do you do with all this marketing knowledge?” When I spend millions of dollars on marketing, I think I’ve tested every single channel. I said, “What do you do?” You become an agency, right?

So, we started, I was like, we’re going to be an agency focused on tech-enabled products because that was just what it was because our funnel was very complicated, by the way. What we do right now with e-commerce is so easy. I was like, “This is the easiest job ever.” Compared to what? My experiences. But guess what? Like 2018, 2019, not a lot of tech-enabled products anymore. They were all 2013, 2014, and everything about Shopify at that time was Shopify, Shopify, and Shopify. We learned, the first customer came, was in a fashion company. As I said, it was a much easier learning curve. I was like, “Whoa, this is much more simple.”

And I know that if you want to go and kind of coming in into the new industry, in your business, you need to do something really well better than somebody else. So, we decided to focus on e-commerce businesses. And right now, we’re an e-commerce marketing agency, but that’s what kind of inspired it. I had stuff that was one of the best media buyers spend the most big budgets, and they decided to walk with me and I was like, “What’s going?” I had good reputation already with the JetSmarter story. So, within first month, we got a lot of customers right away. The people are like, no matter what you do, these represent us and cash flow positive business and that’s how I ended up here.

Adam Robinson: That’s amazing.

Lolita Petrossov: It was like I never had inspirations to start an agency. I had kind of ideas because at JetSmarter, when we were talking about we’re having hypergrowth, and at some point, every business kind of plateaus and we have these budgets and I’m like, “Okay, we’re going to go for big agency.” Maybe they know better than our internal team. And we had a team of about 30 people in marketing, right?

So, we go for Zimmerman. It was a disastrous experience, Omnicom brand, and then we hire VaynerMedia. I go in and I meet Gary Vaynerchuk, and they represent us. It was the last six months. And we did a campaign together that flopped. It was the worst thing that we’ve ever done. Actually, I kind of went with it because I was hoping that they know better.

But at that point, I realized that this agency game is not an easy game. You get sold by the CEOs, and they tossed you to the marketing interns that don’t have experience. They don’t understand the pain points that the business go through. They cannot console the CEO in terms of what to do, where to spend the money because they don’t know. They don’t have that experience, right?

And that was kind of another inspiration. I’m like, I’ve been in this seat of being the CEO, COO. Controlling big budgets and hiring agencies, I know what it feels like. I know what they want to hear. I know what their pain points are. And yeah, so this is what I do now. And I think that this is why we’re successful is because we’re very untraditional.

Adam Robinson: And do you enjoy the life of someone who owns an agency?

Lolita Petrossov: Do I enjoy it? Depends on what day you ask me.

Adam Robinson: Right. But I guess, a better question is, is this a five-year plan, a 10-year plan? Do you aspire to get in the middle of something like JetSmarter again or where did you feel– and this is a complicated question because I truly believe that each stage, your life is changing so much at the same time, like being in the middle of JetSmarter if you have two kids in private school. I’m not sure that you would want that or whatever, right? But do you find it– like Diana, my co-founder, she runs her life in a way to where she’s always very busy, in general. And then she started this agency after a sales job and she just took on too much work and she was doing all the work and was running all– it was unbearable for her. So, that was why I asked the question. Do you find sort of this whole dance that you do is the person who owns the agency, something that is long-term sustainable for you?

Lolita Petrossov: Well, a lot of people– number one question that I get asked, they say, why do you still work? You don’t need to, which is true. And I was like, I think that I need a therapist to answer that question because I don’t know how to answer the question.

I think that it comes from my childhood. Since seven years old, I was working very hard on a tennis court. I don’t know what it’s like not to. So, I like that busy chaos life. This is what I am. And you can’t take that identity away. If you take it away from me, I lose the purpose of life, really.

Adam Robinson: I love that.

Lolita Petrossov: I’m a mother, I have kids, I’m a wife. I have a business, I’m always busy, but I don’t know how not to be. It’s agency. You know what I enjoy? I enjoy helping businesses grow. And this is our DNA. I am not an easy agency to work with. When they hire us, I tell them I am not going to listen to your ideas. You’re going to repeat the mind. This is what we want. We are not price cheap, right? But I say that if I take you, I guarantee you success, but you need to listen.

But I’m not going to be one of those where you call in and tell me how to set up my campaign, ask me why I set up this tool., I love your tool. I am a huge believer in it. I force everybody to get it that I believe will benefit from it because it’s going to help me deliver better results for them because in e-commerce, you are as good as your customer list, right?

So, that DNA of kind of being an untraditional agency and helping them grow, but in order for me to say that I guarantee, I need to run it. They need to turn– so my initial conversation with the brands, the ones that do it, they stay with me for a long time and they scale. And this is what makes me happy because can I do it over and over and over again and help? And this is what I enjoy doing. It’s not as much as like– the agency does very well, very profitable, right? We have a profitable model. I learned that from the JetSmarter agency.

But what gets me high and what gets me excited is seeing the baby brand going from 500k in revenue to 12k in a matter of 18 months. And I have these case studies, right? Guess what? The best ones are the ones that listen because I tell them, “Listen, if you want to come and present an idea, probably tried it, and I had an expensive lesson of failing a lot of things in marketing. I know. Please trust that I know.” And that’s the kind of the DNA of Evestar that we have that I can relate to these people and my driver is helping them.

And now, the driver is my– I have a very good team and they deserve to grow and they deserve to eventually run the agency. They deserve it. They’ve been with me for– since JetSmarter age. Like, at some point, I think that I can just step away and they will run it because they’re better than me. They’re more passionate. So, I think that’s the thing. And then I’ll probably move on to the next thing.

Adam Robinson: I think that that’s so energizing. My last business was not growing and there was just Stacy’s everywhere. And I still work with a lot of the same people, but we have brought these people around us who are so incredible and I just get so much energy from even thinking about it. I’m like, “Oh my God. These people get up every day and they choose to work on this. I can’t fucking believe it.” Like to be on a call with someone who’s just so bright and like– it’s amazing. I love that part of it, too. Well. I mean, I think that that’s kind of all that was amazing, the whole thing. So, I wrap it up with these two things, if you could write one message on a billboard, what would it be for everybody to see?

Lolita Petrossov: Okay. One message on the billboard.

Adam Robinson: Yeah. For something that’s the essence of like a lesson that you think you’ve learned that everybody could– you know what I mean? Like…

Lolita Petrossov: You know what? You have to dream. You have to dream big, but you have to understand that dreaming is not enough. You have to do a lot of work to get there. But you have to have two components. You have to be a dreamer. You have to be crazy a little bit, but you have to be willing to put it all in line and work because dreaming is not going to just get you there. And I see a lot of talented people today. I meet and they dream, but they don’t work hard, right? Why are you going to show up and grind it out? Listen, at the end of the day, looking back, that story that I remember from JetSmarter is the process of getting there, the grind, that you enjoy the grind.

Adam Robinson: Yes.

Lolita Petrossov: And if you do, you have it because a lot of people don’t enjoy the grind, but this is what they dream of.

Adam Robinson: And another thing that I think is important about dreaming and being able to articulate your dream very well is it lights the fire in people. Your dream transfers to their dream. And the bigger it is, like occupying Mars, I thought, is just the most ingenious two words I’d ever heard in my life. Elon Musk is like– that is just the craziest idea, but it calls part of you as a human. It’s like this is the most ambitious thing I could possibly be doing with my life, trying to occupy Mars and make humanity a multi-planetary species. It’s a lot of f*cking work.

Lolita Petrossov: I think he’ll get us there for sure, Elon.

Adam Robinson: Yeah, for sure. But he’ll get us there, it’s not him. It’s the people that he’s willing to– that he is able to pull into this thing and there’s no better marketing to them than these two words that just stab you in the heart, right? And I just love that. It’s like a dream, but he can articulate this dream, spell it out logically for people. The tagline is perfect, and then it’s like, by the way, to work at…

Lolita Petrossov: Well, some people are born leaders and I think that this is why, if they have this gift, they have to use it to do good for the world, I guess, right?

Adam Robinson: For sure. For sure.

Lolita Petrossov: And then not a lot of people have it. Some people need that leader to go lead and follow them.

Adam Robinson: Great. Okay, so where do you live?

Lolita Petrossov: South Florida, Boca Raton.

Adam Robinson: Boca Raton, love it. What is your family size? You’re married, how many kids do you have?

Lolita Petrossov: I have two kids. I have 13 and 11, a boy and a girl. And I’m married to the famous Sergey Petrossov.

Adam Robinson: Do they play tennis?

Lolita Petrossov: No, no. You know what? I hate tennis. I don’t like tennis. I think it’s such a stupid sport. I played it. I was very good at it. It has given me everything that I am, but I’m one of those people when I move on, I move on. So, that’s another thing that ever since I finished, I never touched the racket again. It doesn’t attract me at all. I’m so into– yeah, they don’t, but they play– my son is a hockey player. He’s obsessed about hockey. He’s very good.

Adam Robinson: Interesting Florida sport.

Lolita Petrossov: Putting a lot of pieces there. I believe you need sports. Sports is– especially for boys, that’s discipline and that’s drive. You learn how to cooperate, be a team player, which is very important in life. And daughter is into acting. She’s very creative.

Adam Robinson: Great. What is your favorite book?

Lolita Petrossov: What’s my favorite book? Hold on. It’s right there, hold on. There are two, actually. The favorite one is Shoe Dog by Phil Knight.

Adam Robinson: Oh, what a great book. Just could not.

Lolita Petrossov: And in terms of the marketing is Building a StoryBrand by Donald Miller.

Adam Robinson: Building a StoryBrand.

Lolita Petrossov: Yeah. It’s unbelievable. It completely opens up your mind how to think about your customer. Really good book but…

Adam Robinson: I’m going to read it.

Lolita Petrossov: Yeah. The Shoe Dog is always a good read.

Adam Robinson: I mean, the Shoe Dog, I was reading it and this was before I started my current business. And I was just reading about how people were coming to his apartment and he couldn’t keep the shoes in his apartment because people were buying him so fast and wanting more. And I was like, this business is never going to work and probably is not good enough. And then, sure enough, eight years later, I have something that’s experiencing that sort of demand. But I just love that story, so wonderful. And he just seems like such a great guy. What an awesome story. Do you follow people on social media? Do you have somebody who’s your favorite to sort of follow?

Lolita Petrossov: Do I follow people on social media? I mean, the standard, but nobody that– I mean, I follow a lot of people. Elon is my favorite. That’s obviously– I follow everything Elon does, but then I follow all entrepreneurs, but yeah, Elon is my favorite.

Adam Robinson: Mine, too. What’s your favorite vacation you’ve ever been on?

Lolita Petrossov: Aspen. We go ski every winter. That’s my favorite place on Earth. Colorado.

Adam Robinson: I rented a condo at the base of Ajax for five years in a row, all winter.

Lolita Petrossov: Nice.

Adam Robinson: I ski 300 days. This was before I had my first child. Six months ago before the child, it was Aspen.

Lolita Petrossov: I live in Florida. I don’t like the ocean because we live here, but skiing is my weakness, mountain skiing, Colorado. Oh, my God. I can go there. It’s my favorite vacation I’ll go to every single year, and I will experience that same high.

Adam Robinson: Have you been in the summer?

Lolita Petrossov: No.

Adam Robinson: You got to go. Just go. Like in August sometime when it’s hot as f*ck in Boca Raton, it’s like nice there. The thing about it is, it’s not just about the ski mountains. It’s like the whole valley. Your activity expands to these hikes that are all over the place. They’re incredible. The weather is perfect. You can like– there’s a whole camping side to it. There’s floating down the river there. There’s biking and running and fly– I mean, it’s just like the breadth of activity during the summer is just incredible. You can e-bike up to Maroon Bells and picnic up there. Everybody says, like, they go for the winter and stay for the summer, people that live there. You got to go.

Lolita Petrossov: Never been in the summer. It’s always the winter. Summer, we leave, we’re always in Europe in summer.

Adam Robinson: Oh, okay.

Lolita Petrossov: Always fly around Europe, that sort of thing. But Florida is impossible to stay in the summer.

Adam Robinson: Yeah, you can’t go. Oh, my goodness. Thank you so much for this hour. It was wonderful. I really enjoyed getting to know you and that story is just…

Lolita Petrossov: Thank you. Now, I’m rooting for you.

Adam Robinson: Well, thank you. Thank you.

Lolita Petrossov: As your agency partner, we believe in your product. By the way, a couple of the case studies that I’m publishing right now, 100% related to Clients that we got back in the day when you would get emails, which was not long ago, that we were able to get them in the beginning of the year on Their customer list has grown so exponentially. When we’ve got to Q4, record-breaking, blew all of our projections out of the water, so.

Adam Robinson: Can we do a case study with your agency in one of these and put on our website?

Lolita Petrossov: Yeah, let’s do it.

Adam Robinson: Sweet. That’s great.

Lolita Petrossov: We have two that– and by the way, what about all of this recession talk, right? Like, ooh, what’s happening? Demand, right? But I’m seeing that people that had your tool, they were able to drive through this way better than others. It’s frickin’ great. I am your big fan.

Adam Robinson: Those words are literally…

Lolita Petrossov: And we just met on this podcast, you see? I just reached out to you on Twitter. I have no Twitter followers. I just started. Okay. I didn’t even know that you were a customer of JetSmarter. But now, I’m your customer. I think that you’re going to do just fine. Just keep grinding it out, focus on your product. Nobody else does it better than you.

Adam Robinson: Exactly. That’s my hope. We have this 24-month window to just get it. But unlike JetSmarter, I’m really going for it. We were so cash flow positive when we started, really gunning it with go to market that I can’t spend the money fast enough. You know what I mean? It’s like you spend it and it grows. So, I’m going to, hopefully, avoid the pitfalls of being like, oh, we have to change everything.

Lolita Petrossov: No. By the way, remember the learnings, don’t overspend.

Adam Robinson: Yeah, exactly. Well, the thing is we narrowed our focus dramatically in September. Now, we’ll only sell to big Shopify stores. You know what I mean? It’s like I’m increasing focus as we’re putting muscle onto it, which is like…

Lolita Petrossov: Increase the focus and do it better than everybody else, but you have to– right now, you’ve got a lot of people’s attention. You got my attention because listen, these case studies are phenomenal cases with a shoe brand and with a fashion brand. By the way, if we didn’t have, they would have had a sh*tty Q4.

Adam Robinson: I mean, these words are unbelievable. Can I have that quote?

Lolita Petrossov: And you’re like, bail this out, for real. But that’s the thing, we got them. Once again, it comes from the trust from the customers, the brands that I represent. We came in and said we need this tool because we anticipate that paid media becomes more expensive. We need to capture the leads quicker. We need to get emails. You were so-called, right? But the amount of emails that we were able to generate with people not optimized is crazy. They crush, they Q4. We would not do it without you.

Adam Robinson: That makes me so warm and fuzzy inside. Just to me, it’s like every entrepreneur’s dream is to hear those words. You know what I mean? To be the energy that I am putting out in the world is transformational for people.

Lolita Petrossov: It is transformational.

Adam Robinson: I don’t care about the money we’re making. You know what I mean? It’s like I do to the extent that it affords my super-ambitious growth plans, right? That’s all that I care about. That’s what matters because now, I understand that’s what will make it grow even faster, right? These ideas can’t stay bottled up forever. Something that is that impactful, oh, the reason that they’re surviving this recession is probably like that perpetuates. Thank you so much.

Lolita Petrossov: We switched roles. I am a big supporter. Let’s go. I will keep going.

Adam Robinson: Thank you for everything.

Lolita Petrossov: Thank you so much.

Adam Robinson: So, you’re starting on Twitter. How can people learn about you?

Lolita Petrossov: Yeah, I’m starting on Twitter, let me tell you. It’s a grind, by the way, right? You got to put so much time into Twitter nowadays. Yeah, I just started it a couple of weeks ago. I have only 60 followers. So, I know that I have to pump content, but I’m very busy right now day-to-day in the strategy and the growth of the clients. So, yeah. But they can follow me because that’s right now my goal is to put all the learnings out there.

Adam Robinson: Yeah. If you want …

Lolita Petrossov: You were actually my first tweet, meaning my first DM on the tweet. I followed you. And I’m like, all right, You were the first message I ever sent.

Adam Robinson: Amazing.

Lolita Petrossov: Let us here.

Adam Robinson: That’s funny. So, if you want to have a separate chat about all I’m creating, I don’t know if you know this, and a huge amount of founder brand content and I can sort of– I’ve managed to come up with a system where I’m doing it very efficiently. I’m only spending three or four hours a week and it’s creating 35 different pieces of content that…

Lolita Petrossov: Wow.

Adam Robinson: Yeah, I know, it’s bananas. I can have a whole– I can explain to you how I’m– and the distributions about optimize yet, but at least, it’s creating a daily work in public video one of these per week. And then from all of that, I have guys that are creating tooling to impose a Twitter thread every day and then two newsletters a week. So, it’s just like, I mean, let’s have another conversation. I’ll explain to you why I’m doing what I’m doing and you can go. That applies to me or not, right? Like either unique sort of situation going on right here, but like, cool. Okay, I’m going to hit stop. Thank you very much, Lolita.

Lolita Petrossov: Awesome. Thank you so much.


After growing up in Uzbekistan and playing Division 1 collegiate tennis, Lolita Petrossov had never worked a job.

So for her first gig, she co-founded JetSmarter, an on-demand private jet charter company valued at over $1 billion before its acquisition by Vista Global in 2018.

Now, Lolita is the founder and CEO of Evestar, a marketing agency that has helped more than 100 eCommerce companies scale in the past three years.

In today’s episode, Lolita sits down with me to talk about her stratospheric rise to the top, along with how she and her husband used emotion and status to build JetSmarter to 10-figures.

You’ll also hear Lolita discuss her favorite type of brands to work with as an agency owner, why you need to be careful when dealing with the media, and why dreamers also have to be doers.

Key Takeaways with Lolita Petrossov

  • How Lolita went from growing up in Uzbekistan to founding JetSmarter as her first job.
  • The value of being in the right market at the right time.
  • The story behind how JetSmarter raised nearly $200M in funding.
  • The value of creating virality in an app to hook users.
  • What metrics indicate you might have a winning product on your hands
  • The mistake JetSmarter made during its hyper-growth phase that eCommerce founders also make.
  • Why it's crucial to pay attention to unit economics.
  • The good and bad sides of media coverage for founders.
  • How creating a product with an emotional tie to the consumer can cause founders to lose control of their company's narrative.
  • How Lolita transitioned from selling JetSmarter to founding Evestar.
  • What are the best types of brands to work with as an agency owner?
  • What is the one message Lolita would pass along to entrepreneurs?

Lolita Petrossov | The DNA of Evestar Helping Business Grow

Lolita Petrossov Inspiring Quotes

  • This is what I call a cultural phenomenon that our members, they were so into (JetSmarter). It was adrenaline to them to hop and experience this flying that they were checking the app way more than they check Facebook and Instagram.” – Lolita Petrossov
  • “You have to dream. You have to dream big, but you have to understand that dreaming is not enough. You have to do a lot of work to get there.” - Lolita Petrossov
  • “Coming into the new industry, in your business, you need to do something really well better than somebody else.” - Lolita Petrossov
  • “Whenever you’re growing something and you pay attention to your unit economics, don’t overspend. Let the results do the talking.” - Lolita Petrossov
  • “Stay humble. Stay out of the media side. Because the media, they love you, but then they can destroy you very quickly when they choose to.” - Lolita Petrossov


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