Lean, Profitable, and Free: How Alexandra Cristin Scaled Smart and Sold Big

In this episode of the Growth Mavericks Podcast, host Adam Callinan sits down with Alexandra Cristin, founder of Glam Seamless, to unpack an extraordinary journey — from growing up in poverty to building and selling an 8-figure eCommerce brand. Alexandra shares how she turned $1,500 and two shades of hair extensions into one of the most recognized online brands in the beauty space — without paid ads. She credits SEO, relentless content creation, and the power of constraints for forcing creative, profitable growth. After scaling Glam Seamless to over $10 million in annual revenue, Alexandra sold to private equity — and learned the hard way that staying on post-acquisition can drain even the most driven founder. From burnout to rebuilding her passion, she opens up about her biggest lessons on leadership, legacy, and self-restoration.

Adam and Alexandra also dive into:

• How constraints can be a superpower in business
• Scaling without losing control (or your sanity)
• Why founders often spend recklessly after success
• Navigating burnout and rediscovering purpose
• The truth about private equity deals and earnouts
• How financial discipline and the right systems (like Pentane) can drive smarter growth

If you’re an eCommerce founder or operator heading into Q4, this is the ultimate conversation about scaling sustainably — without losing yourself in the process.

🎧 Explore more at:

• www.pentane.com
   – The Command Center for eCommerce growth
• Growth Mavericks Podcast
   – Fuel Your Growth. Control Your Future.
• https://www.linkedin.com/in/alexandracristin/
• https://www.instagram.com/alexandracristin/

Creators and Guests

Host

Adam Callinan

Adam Callinan is the founder of Pentane, a financial and advertising command center that empowers brands to drive predictable revenue and intentional profit. Previously, Adam co-founded BottleKeeper, a bootstrapped consumer brand that scaled to $8M in sales within three years – without employees – and was later acquired in 2021 as an eight-figure business with a team of four, marking Adam's second successful exit.

What is Growth Mavericks?

This podcast dives deep into the tactical moves that drive business success, as well as the mental and physical resilience required to sustain it.

Hosted by Adam Callinan, a seasoned entrepreneur with multiple exits, an avid outdoorsman, and an family man with crystal-clear priorities, each episode unpacks real-world challenges, actionable insights, and the mental and physical disciplines that fuel long-term personal and professional growth.

Whether you’re scaling a startup or refining your mindset, disrupting your default is how business and life strike a balance.

Adam Callinan (01:05)
Our conversation today is with Alexandra Cristin. She has a fascinating story. She grew up in poverty. She won a spot at the Milton Hershey school, which we spent a lot of time talking about. It's absolutely fascinating. And she came out of that with really crystal clear ideas on legacy and ownership. In 2012, she launched Glam Seamless with $1,500, two colors in a Shopify store. She did no ads. It was just SEO and tons of content. And that

played really, really well. It was perfect timing for the product. She turned that into an eight figure accent, private equity. So we have some similarities there. We talk a lot about that as well. We dig into, we spent a lot of time talking about constraints, which is something I'm gonna spend a lot more time developing content around because it's actually really powerful. We talk about them being a superpower, ⁓ how dealing with skew, creep and margins. ⁓

what most founders or at least many founders get wrong after an acquisition. She also, she's super candid about her story and missteps. She's really upfront and honest, which is a great thing. In her new latest ventures, talking about spending sort of without constraint, which is something that I have personally dealt with in building Pentane with some capital in your pocket, totally different experience. And you just think about things differently. So. ⁓

staying on too long with that private equity transaction, getting burned out and all the things that she's doing differently now. So this is particularly timely for you entrepreneurs and e-comm founders and operators going into Q4, trying to think about what to cut, where to spend, how to keep your energy and mental intact. It's really, really an amazing conversation. So I hope you enjoy this time with Alexandra Cristin.

Adam Callinan (02:50)
Sweet. So you mentioned you're you live in the hills where what state are you in? What part of the country or world? Okay. the Hollywood hills, the fancy hills. Okay.

Alexandra Cristin (02:54)
Yeah, I'm in California. So I'm in West Hollywood, California. Yes.

And where are you? Where are you located?

Adam Callinan (03:04)
Amazing.

I'm in Bozeman, Montana, but I lived in Manhattan Beach for a long time for like 10 years. We moved here in 2020 in early COVID. We still had a house in Manhattan Beach until last summer. So we kind of split time, but we were in Montana.

Alexandra Cristin (03:09)
Okay, awesome.

Perfect. I looked at farms

in Montana. Montana looks so just away from everything and beautiful and restful. You too, you had an acquisition yourself as well, right?

Adam Callinan (03:30)
Yeah, yeah, I've, yeah,

I did a couple in 2021. A bottle keeper was that company we got acquired by prior equity. But we built that company in Southern California. I our offices, our office was in El Segundo. So we were we were down in your hood is great.

Alexandra Cristin (03:38)
That's amazing. That's amazing.

Yeah,

yeah, amazing, okay.

Adam Callinan (03:47)
Yeah. Yeah. So how does, I mean, I did some digging around in prep for this conversation and it, it seems that you have a pretty interesting backstory that, probably led to or created the foundation for a lot of the success you had or have had thus far. So why don't we start there? Where, where are you from? And how does that, how does Alexander get started?

Alexandra Cristin (04:11)
1989 born in Harrisburg, Pennsylvania to a single mother the odds were against me literally like my mom or three jobs and It was not the idyllic childhood that you would want for a child Long story short the universe always has its way, know, my mom always prayed She always believed in a higher power and I ended up at nine years old getting into a boarding school

So the boarding school is called the Milton Hershey School and it's a K through 12 boarding school in Hershey, Pennsylvania. That is one of the most hidden underrated schools in all of America. Basically the founder of Hershey Chocolate ended up starting this school in I think 1907 at first for boys and it's scaled to girls and boys. And basically this is a free boarding school for children in poverty. The goal of the school is to help children escape poverty. So

You go to this school, you can enter from all the way kindergarten up until eighth grade. They want you to go by eighth or ninth grade so that you get the learnings of the school. So at first nine years, go up really poor, really rough neighborhood, learned a lot of street skills, if you will. My mom went to jail several times. you know, at first, when I was going through it, felt very sad. But looking back, obviously that built a lot of tenacity, resilience within me, which obviously all those things are required for running a business.

And then I went to this boarding school for nine years. So the boarding school was pretty strict. It wasn't, you know, what you think of like a, you know, the Annie orphanage, not that type of vibe, but the boarding school was very focused on helping children from poverty who come from low income families really get acclimated and adjusted to society, being a functioning, contributing member of society. And so that's everything from tucking in your shirt.

folding your clothes a certain type of way, walking to school, three to four extracurriculars. And they have a system and it works. When the children follow it, it works. So I was a really, really bad kid when I got there. There was a lot of work that they had to do on me. But long story short, over those nine years, by the time you graduate, if you do a good job, they pay for your college. So they'll pay for you to go to a state school.

So this school is amazing. It's literally still exists today. It's free. It's the most amazing thing. When I look back, I know that that's what inspired me to be an entrepreneur, to think about it. This entrepreneur created a chocolate company, made so much money, made his own town, made a boarding school and gave back. And it's just like today, that company obviously is publicly traded. Hershey Company is publicly traded. 55 % of the company's net profits go to the school.

So the founder, Milton S. Hershey, he already sat in his deed of trust and he's died over a hundred years ago. Well, I think he's gone maybe a hundred plus years. Talk about legacy, talk about entrepreneurship. When I think of entrepreneurship, I think of someone like Milton Hershey, where he not only had a vision and Hershey Chocolate Company was his like third or fourth company, he had had multiple failures. So I think that is just so ingrained in me, entrepreneurship and what that looks like.

The story at the boarding school is told to us over and over again about him failing, him starting this chocolate company, him creating this school. And so when I look at those nine years, not only was I given this very elite education that you with upper class families have for their children, right? The best schools, the best food, the best extracurriculars. I got that all for free. ⁓

while also I got this beautiful message of entrepreneurship and I saw subconsciously what it does. So that's what my beginning years looked like. Grew up really tough and then went to this great boarding school that molded me with this clear understanding of how much entrepreneurship could really change one's life.

Adam Callinan (08:10)
talk you mentioned in the midst of that legacy, which is what I was thinking of, you know, a lot of the time you're telling the story. What a legacy. I mean, I think do people know that like that don't you know, that didn't come through that like, holy cow talk. I mean, on one hand, that's kind of beautiful that they just do it. Not for publicity, not for whatever, but what an incredible I mean, that that's like a that needs to be a documentary like a ⁓ movie. That's unbelievable.

Alexandra Cristin (08:20)
No!

Yeah, exactly. Exactly.

It really hurts. And everybody knows

Hershey chocolate, right? I'm pretty sure everybody, but nobody really knows about the boarding school, which is free and exists today. There's not even an application fee. You know, like a private school, there's an application fee. There is no application free. It is literally free. And so in that, and I look back at like how I got into the school and my mom used to be a paralegal and another paralegal told her about the school and she went to go work at the school. This, my mom's friend, Donna.

Adam Callinan (08:40)
Of course, of course.

Alexandra Cristin (09:04)
She's still there to this day, 25 plus years later, working at this school. So it just goes to show too, it's like the organization itself is amazing and nobody knows about the school, but it really inspired my vision for legacy. So fast forward, I ended up graduating surprisingly because it's really strict. You've got to follow what they say. It's a strict school. You've got to follow the plan and you've got to do what they say. And so ended up graduating.

And instead of, this is where my first risk taking came in play, because to be an entrepreneur, it's all about the risk. It's how much are you willing to stomach? How much are you willing to bet on yourself, invest in yourself? So at 18 years old, instead of going to the free school that I was offered, could have went to a free school in Kutztown, Pennsylvania, a state school, I decided, you know what? No, I'm gonna take out 100,000 in loans and I'm gonna go to an elite private school in New York City.

⁓ So that was my first decision at 18 years old. Could have just taken the free school, but for whatever reason, I had these wild dreams of moving to New York City and being a plus size model. Always grow up big girl, and I always decided, you know, I'm gonna go to New York and be a plus size model, but I'm gonna go to college as a backup plan since 50 % of it's already paid for or whatever, it's just loans, like who cares? So get to New York City at 18 years old at Pace University.

Now, Pace University is a great school in New York. It's a business school. And this also changed my life. So when it comes to life and destiny, there's always certain things that just, things happen for us. I truly believe that we all have a destiny. So I land in New York City, go to this business school. studying marketing. And long story short, this school was, how do I put this? I'm trying to look for the right words.

Adam Callinan (10:51)
You can just be honest. It's fine. ⁓

Alexandra Cristin (10:55)
The school had a lot of wealthy kids there my age. So my peers were very wealthy. Their parents gave them brand new BMWs to go to school. And I'm like, it was the first time at 18 years old that I realized I was poor. Cause I grew up in a small town in Pennsylvania with a whole bunch of other poor children at my boarding school. So it was the first time at 18 years old that I ever saw wealth. And I was blown away. I also used to nanny. And so the people I nannied for

were executives, they were CEOs who worked in the city. And so my world changed at 18. So step two, like risk taking number one, how much are you willing to risk? But step two, changing your environment, right? I wasn't comfortable in this wealthy environment, but here I was in this very, I was actually in Westchester. So Westchester is a very elite part of New York. So nannying for wealthy families who were working like crazy, going to school with my friends who are now like,

going to Neiman Marcus with daddy's credit card and buying whatever. And then I happened to take a sociology course, which changed my life. So this sociology course really highlighted the differences between growing up the classes, right? Classes in 101 is one of the core things that we studied. The poor people do this, wealthy people do this, poor people eat junk food and watch TV. And I'm like, oh my goodness, I was subjected to this poor life my entire life and I had no choice. And I got really angry.

By the end of that freshman year, I got super angry that I was subjected to being a poor person. Now I grew up overweight, remained overweight because I struggled with my weight, junk food, my mom never cooked, right? She's working three jobs. And I just was like, I cannot believe that I grew up as a poor person and I didn't have a choice. I didn't have a fighting chance. Like I got really angry.

So I think at that moment after the sociology class, I decided that I myself was never gonna be poor and I myself was gonna do whatever I could to build my own type of legacy and give back to people one day. And so that was kind of like where my life started to really change. I'm in this new environment and I'm like, I can't believe it. this, everything opened up for me and I just said, I said to myself, this is it, I have to change my life.

So am I talking too much?

Adam Callinan (13:12)
No,

no, this is the whole point is for you to be talking. So no, no, it's great. It's all the story. mean, it's there's just these chapters. I always looked at life as a series of chapters. And I think that's important because you do need to come to a point and you were only a freshman year of college and you can already see like these clearly defined chapters. But within that, there needs to come a point where a chapter closes. They're like a clearly defined close of chapter.

Alexandra Cristin (13:14)
Bye.

Absolutely.

Adam Callinan (13:40)
And that's

what that sounds like for you was a really important self-realization that's hard to do, especially at, I mean, were 18, 19 years old, like a deep self-realization to close that chapter and make some significant decisions. I have a question going back to the Hershey School. Did they direct students toward

Alexandra Cristin (13:49)
Yeah.

Yes. ⁓

Adam Callinan (14:06)
entrepreneurship or was it just sort of general education? It's like, wonder with that student, the student population going there, seeing that what the percentages that had a realization like you did, where it was like, this happened because somebody took a risk, they were an entrepreneur and it worked, I wanna go do that.

Alexandra Cristin (14:25)
Yeah, they did not push entrepreneurship. There are some very successful people that came from there. ⁓ Jason Wolf is one of them. He's my mentor. He's in his 50s. He's sold four companies, one of them for over nine figures. So there are some, but I wouldn't say there's many. And this is why, because unfortunately you have to change your environment to change. And I feel like the school still has an opportunity to get the families on board. Like the families have to change or the child has to decide to leave Pennsylvania after college and

not go home. I think like poverty is a cycle, unfortunately, and there are some people and I don't want to speak negatively of the school, but it's about the environment. So entrepreneurship is not pushed. And also there are still, unfortunately, some children that just don't get it, don't ever make it. They don't even utilize their scholarship. Now that's a small percentage, but they still exist. And so I think it's risk plus environment changing that really is what's going to catapult somebody into success, especially having the makings of entrepreneurship.

But no, they don't push entrepreneurship. ⁓ But I just think it's subconsciously in our back of our minds. Like, you know, we're children, we can't really process what's going on, but by the time you turn 18 and you leave, an entrepreneur started that company, funded all of that. And so I think it's just, for me, it was the obvious and it was there subconsciously.

Adam Callinan (15:42)
Yeah, and that makes perfect sense. So, you're post sociology class, you're pissed, you're making changes. Did you rush out and start a company or did you finish school and deal with entrepreneurship later? They all blend together.

Alexandra Cristin (15:58)
Yep. Nope. So I finished school. I did some reality TV, some plus size modeling. I fulfilled my dreams and you know, I finished school. I finished school and I had a really great time. I had internships at Ernst & Young and I really thought in college I was going to take the corporate route. I ended up changing my major to accounting at one point, landed this huge internship at Ernst & Young in which we were on the fast track to become a partner and get a ⁓ job right after graduation. And so for me,

I did finish school and I thought for sure, you know what, I'm just gonna make a lot of money through the corporate world. That's what I thought my plan was. Graduated college and I thought to myself, I'm going on these interviews and I thought to myself, I just cannot do this. Something in my stomach was like, I cannot work this corporate life. I'm getting sick. I mean, I have a big personality, but I'm an introvert. I really get charged being by myself with my own vision and my own thoughts.

So I just started to have this little gut feeling. I said, this can't be it. I cannot take a corporate job. I don't care if I have to pay the student loans off. I can't. So I decided to keep nannying honestly. I'm like, you know what? Nannying pays cash. I'm 21 year, 22 years old, whatever. Like I can figure it out later. So I kept nannying and I avoided the corporate route. Well, after doing the nannying and trying to do a, become a plus size model, it just, it wasn't working. And I'm like, okay, I think I've got to start a business.

Now this is in 2011, 2012 at the height of Shark Tank coming out. So I was a recent college grad, broke, having to pay my student loans, nannying, didn't opt for the corporate route with my good salary. So I was home on Friday nights when Shark Tank would air and it was pretty new and popular. So what would I do in my apartment? I would watch Shark Tank every single Friday and I really enjoyed it. And I feel that Shark Tank really, really put it in me to start a business. I would see these

pitches every single week and I'm like, this is a great idea. This is a great idea. You know what? I think I can do it. So I bought a business book off Amazon, literally called How to Start a Business and I followed the steps and I looked at starting businesses. So I had three different ideas. So 2011, I'm like, okay, I've got to get out of this nannying thing. Clearly I didn't go the corporate route. What am I going to do? So I started kind of panicking. I'm like 23 years old at this point. I'm like, oh shoot, I've got to figure this out. My mom's like, when are you getting a real job?

You took out these student loans. What are you going to do? I'm like, I'm going to, I'm going to figure it out. Long story short, I am like, okay, shark tank, three business ideas. I'm looking at these three business ideas and I'm also looking at my bank account and I'm like, okay, I don't have that much money at all. don't have that much money. So we've got it. Let's look at the business, see how much it's going to cost to start. So I had three ideas and I chose them are all my passion. Cause I believe when you, and I know people have different thoughts on this, but I believe for me, when I'm passionate about something, doesn't feel like work.

So I chose the beauty industry and I looked at a makeup company, I looked at an eyelash company and I looked at a hair extension company. So I wanted to do this makeup idea and it just wasn't gonna require too much money for capital for inventory. So I said, okay, this is not gonna work for me. I don't have the money. I looked at doing eyelashes and selling eyelashes. And then I was like, you know what? I'm not good with my hands. This isn't gonna be a good idea. And then the third option I landed on,

was hair extensions and I loved hair extensions. I've been wearing them since 14. And so that's how I landed on my first business which ended up going off to be a success with an eight figure exit, bootstrapped it and it was life-changing. But I started with my hair extension business, Glam Seamless in 2012, $1,500, literally put $500 into product.

$500 into like a designer helping me get up the rest of my Shopify store and $500 and I'm not sure maybe I'm not sure what I spent the other 500 on but it was $1,500 and I bought two colors which most extension brands have 30 40 50 colors I bought two colors I made my own stickers on the packaging and I just I just started writing blogs and doing YouTube videos about hair extensions so Pick something that I loved and then I started adding a lot of value

Now I'm an expert in this field. I've been wearing extensions for over 10 years at that point. So I just started writing about all things, all things extensions. And I didn't know what at the time, but what I was doing was SEO, right? Search engine optimization. And I didn't have any money for advertising. So SEO is really what blew the business up. So after the first year, and we're talking about zero paid ads, zero team members,

Adam Callinan (20:19)
Yeah.

Alexandra Cristin (20:32)
Literally 120,000 in revenue. And I thought to myself, okay, it's not profit, but the sales are there. And I'm like, this is working. There's something here. Still have my nanny job, still taking odd plus size modeling jobs. But I'm like, okay, I can see the traction. Year one. Mr. Wonderful from Shark Tank, right? Kevin O'Leary. He says, if something is not making you money in two to three years, take it in the barn and shoot it, right? Right? Take it behind the barn and shoot it.

Adam Callinan (20:57)
Hahaha

Alexandra Cristin (21:00)
This was working. And so that was the making of Glam Seamless. It was passion. It was, you know, being scrappy and resourceful. And it was SEO because I didn't have any money for ads or influencer. Now what I will say it was there's always luck and there's timing. If anyone says that that isn't an equation in their business, they're wrong. I truly believe that it was timing and choice that helped me become successful when I did.

Number one, there wasn't that many online hair extension brands at the time. Hair extensions were sold in a different way, in a different business model. They were sold B2B. They were sold through distributors only. They were sold in brick and mortars. No one had really occupied the online extension space at that time. Now I didn't know that, but looking back, I'm like, ⁓ great timing. The second thing that happened in 2012 when I started my business is there's about eight or nine different types of extensions that a woman or a person could wear.

I chose a specific type that was very new to the industry. So it was a two year old product. So it's really about timing, right? It's not about money. It's not about having the best team. Although those things obviously always can help. That doesn't help necessarily, that does not dictate if a business is gonna be successful or not. It was the timing and it was the product choice.

Adam Callinan (22:18)
I would add to that that it was also the constraints. There is something magic about having to figure it out and do it in a different way because there are constraints placed on a business. There's so, I mean, you literally can open a business publication, Google something on the internet and you will see 10 million stories of companies that went and raised a bunch of money early on and because they didn't have the constraints,

Alexandra Cristin (22:22)
Mm-hmm.

Yes.

Yes.

Adam Callinan (22:46)
They went and spent it in all sorts of flippant, ridiculous ways, trying to figure things out. And man, there is so much beauty in that the fact that you had a constraint, you may not have wanted the constraint, but you had it, in that you had $1,500 to start with. So magic constraint. But then you also made a choice, and that was to add constraint to the business by being very selective on a specific.

Alexandra Cristin (23:02)
Alright.

Adam Callinan (23:12)
That's another huge mistake early stage operators make all the time, right? They go out and try to sell like 72 versions of the same thing, which means your inventories are spread super thin. It's really hard to like work through the noise and figure out which one works and which one doesn't work. Like go out with one or two versions in one color and that's it. That's a beautiful, beautiful constraint. And I will add timing, I 100 % agree. And I say the same thing.

There's always luck involved. You can never plan for it. It's not a strategy. So let's not pretend it is. But timing is one of those things that you look back at and you're like, shoot, that was lucky.

Alexandra Cristin (23:46)
Yeah, yeah. And I like what you say about constraints because fast forward after my exit, I had some cash around the plate. I wanted to diversify, right?

Adam Callinan (23:54)
yeah. Yeah,

let's let's talk about that because I had I've done that too.

Alexandra Cristin (24:00)
So when you talk about constraints, I'm like, I think I just had a therapy healing moment ⁓ because I ended up plowing half a million dollars into a into an athleisure company for plus size women. And let's just say the sales have not even topped $50,000. So it's there were no constraints. And I also was doing too much. I was doing too many businesses and this and that. And I just thought, you know what? I have money. I can hire people. I can just go. This is easy. And it's

Adam Callinan (24:03)
Yeah.

Alexandra Cristin (24:29)
I like the idea of having constraints because this is something we need to talk about. But yes, I digress.

Adam Callinan (24:36)
No,

I mean, Alexandra, I'm literally the exact same. I in Pentane, that was an organic, didn't mean to start a company, started a company. It's like, well, shoot, I have money now. This is a way different situation. Going and starting up. And now finally, like two years into it, it's actually working, which is awesome. And that's great. And it's growing. But the two years up to that, I look back out now, I look back at and go like, holy hell was I reckless. Because I was, I didn't raise money. Like I was spending my own money. I was.

Alexandra Cristin (24:47)
Yeah.

Yeah. Yeah.

Yeah.

yep, I spent real

Adam Callinan (25:04)
There are so many things

Alexandra Cristin (25:04)
money. yep.

Adam Callinan (25:06)
that I look back and I was like, why the hell I tried this thing and it costs $70,000. Like I should have started the company with $70,000 total. I should have capped it personal.

Alexandra Cristin (25:12)
⁓

Yes, I feel like money is the last thing you need when it comes to being successful, right? Being resourceful, being scrappy, having to make good decisions because when you have the money, you'll just spend it. And sometimes it's like, it's not always the right thing to spend it on. So yeah, that looking back, ⁓ you know, I was very scrappy, very lean. All the money that I made from the business, I put right back into the business and

Adam Callinan (25:20)
It is.

Alexandra Cristin (25:41)
So back in 2012, first year, 120,000 in sales, next year, half a million, next year after that, 1.5 million. And it just took off year after that, five million and then 10 million. So that all happened in a six year trajectory. Owned the company 100 % myself, kept it very lean, probably too lean, burnt myself out. I wish looking back that I would have invested more into a team and I would have invested more into myself to be a better leader, to help them.

get to do the things I wanted to do. You know, there's a saying like, if you want something done, do it yourself. That's like an entrepreneur saying that is a bad saying. It's a bad, it's a bad motto because, you know, what you really need to do is teach people your ways. But I didn't have the leadership skills in my twenties to really let my team know like, this is how I want it done. So I ran the company very lean. I don't know why, just because we kept investing into the profits of the business.

And I never saw this company, but there happened to be a roll up in my industry. And what that means is basically there's a strategic partner that's going to go and buy up all the competition so then they can go roll that up and sell it to them. I like to say it's like a big gambling for these men. They have no interest. I don't even want to say men, groups of investors. They have no interest.

Adam Callinan (26:57)
Yeah, yeah.

Alexandra Cristin (27:02)
in the category, they have no interest in the customer. They simply, it's a money game for them. It's like they're gambling for fun. It's like, hey, we're gonna buy these businesses. We're gonna turn around and forex it. And it's like, that's what they're doing. And they literally did too. So there was a rollup in the hair extension industry and I started seeing my other competitors getting bought out. And I'm like, this is really interesting. Like what is going on here? Next, know, they came knocking at my door because we were one of the top three extension.

businesses in the entire category of direct consumer extensions. Get this call in 2018, hey, we'd like to buy your business. I said, yeah, no thank you, I'm good. They came again knocking, hey, we really wanna sit down, we really wanna buy this business. I said, no thank you. Then a second person, not related, not a part of this organization, another.

firm reached out and said they wanted to buy my business. So now I'm starting to realize like, I'm getting a lot of requests here. This is really interesting. The ego in me wanted to hold onto it. But I said, you know what, let me just take a meeting. Let me take a meeting and let you see. So I met with both of these firms that wanted to acquire the business. And I said, how can I help you? And I had no intention of selling. Zero, zero, zero. Cause why would I? I was having fun. I had my team. I had like 30 employees. It was fun. It was profitable.

It was everything. was so happy. I mean, I was stressed. It wasn't like a dream business, but it was great. I took a meeting with one of them and they said, listen, we want to buy this business and we would like you to stay on. We want you to stay on. We want you to run the company how you see fit. We're basically just going to fund you and we're going to give you a big check right now so you can continue to come on and do it.

At the time I had my accountant with me, Andy, I love him so much. He took the meeting with me and he's an Italian New Yorker and he's in his 50s and he knows business. And I said nothing and he said, listen, this is what we want. So you always got to have an advisor with you because I think if I would have taken that meeting by myself, I think they would have crushed me entirely. These businessmen with their PE firms and I'm like, I would have gotten crushed.

Adam Callinan (29:14)
You

Yeah.

Alexandra Cristin (29:25)
Like, looking back, it was like...

Adam Callinan (29:26)
Yeah, I mean, it's literally

what they do for a job. That's their whole job is to do that.

Alexandra Cristin (29:31)
Yes, yes. ⁓ So long story short, I had several conversations with this ⁓ company that wanted to buy my business. And they gave me a really low, what I felt was a low ball offer for a company that was growing 100 % year over year. They offered me a six or seven multiple. And I said, yeah, I'm not interested. I said, you're gonna pay me off on revenue. And you're gonna, that's what I want. My multiple is off of revenue. And I literally was joking.

Right? So it's always good to be in a place where you don't need or want whatever that is, cause desperation is an energy that everyone can feel. And I didn't care. I really didn't care to sell my business. Like I really don't care. But I, what I will say is I was getting to that point in my business where it was getting so big. It was already past $10 million a year in revenue. I had to either get an investor for a small minority sake or potentially entertain this.

And so I just felt the pressure of like the inventory and the team. And I had never worked a real job. And now I'm running a $10 million plus organization. And I'm like, this is crazy. I'm literally 29 years old. I'm like, what am I doing? I have a three year old and I'm like, I just, I felt like I was drowning at times. And so when these offers came in, I wasn't desperate, but I had an open ear.

they ended up saying yes. I was joking. I literally was like, I want to be paid off of the multiple of my revenue and that's it or we're not having a discussion. And they agreed under the circumstance, which this was a huge mistake looking back that I would stay on. And so I agreed to stay on and I thought to myself, what a great learning opportunity to work with all these executives, have, to be on a board, to work with El Katterton, to work with these larger investors. this is amazing.

And so I did stay on as a learning opportunity. I really didn't know how to run a P and L. My accountant did that. I didn't have anyone to answer to. So in terms of the sale, it was crazy. It literally just went through. It smooth, no hiccups, LOI, great legal team. And when that money hit my bank account, I told them I want like, I want 50 % upfront, day one.

And they're like, the rest are earnouts. And it was a life-changing moment. I will say that. It was very life-changing, but not in the way that you would think in that moment. You're like, this is it. All my problems are solved. No, that's definitely not the case. ⁓ But yeah, the acquisition came through and then I decided to stay on. And I was CEO within this portfolio company now. And that's where the...

Adam Callinan (32:01)
Yeah. Yeah.

Ahem.

Alexandra Cristin (32:15)
real working lessons really started.

Adam Callinan (32:59)
We have a lot of parallels, some dissimilarities, but a lot of parallels in how bottle keeper and the transaction took place and being bootstrapped and having constraints on the business that forced us to think and act and operate certain ways that built a really healthy, profitable business that never had investors. ⁓ And we also got acquired by a private equity firm because one day we had this very similar thing, companies coming and asking. And one day we're just like, we're kind of tired of this. Like, let's just start listening.

Alexandra Cristin (33:27)
And what year was that for you all?

Adam Callinan (33:30)
That was 2020 that We started we started like air quotes started in 2013. We really didn't kick off until 2014 but had a similar like 2014 we did 150,000 in sales all of which was in like the last two months of the year 2015 we did 1.8 million 2016. We did 8 million. We had no employees like it was wild but it was you know, I was

Alexandra Cristin (33:31)
No, mean, how many years did you have the business at that point?

huh.

That's great.

That's insane.

Adam Callinan (33:58)
We were both just like holding the tiger by the tail. was Matt, my cousin, and I started that company. And that was very quickly at the end of 2018. I took a dry erase board and put all these things on it that I was doing that I should not be doing. And I just started circling things that we needed to hire for. So we did start building a small team then. But fast forward, I mean, that was in 2016. Our first team member came on in 17. And we were on Shark Tank, talking about Shark Tank in 2018 when we were way too big to be on Shark Tank, but it was really fun.

and then got acquired in 2021. But I had a very similar experience of like, yeah, yeah, you go to the end of it and it's like this crazy up and down and the private equity thing, like that was a hard deal. Like the transaction was really difficult. And at the end of it, yeah, at the end, it's like you get a wire. Yeah, the due diligence is brutal. I mean, I get it, it's a lot of money, but then you get a wire and you expect it to be over, but it's not, it's just the beginning.

Alexandra Cristin (34:29)
Like seven years. For me too, it was seven years. So around six, years.

The due diligence? Yeah. The due diligence is not... Yeah.

Yeah, of course. Well, back to the computer wire, yeah. No,

and did you have earnouts? So you had earnouts you had to stay on as well?

Adam Callinan (34:58)
Uh, most of it was upfront. had a little bit of an earn out and I did have to stay on, but it was only through the end of the year to, like oversee the transition. But that was, that was a requirement. That was like a, are out. We're not dragging along forever. I mean, we had two acquirers going at it with each other, which was awesome. So we got to, we got to be dictating a little bit of what we did and it worked out well. Yes.

Alexandra Cristin (35:04)
much.

Yeah, that's how you do it. That's how you do it. So you guys wanted to walk away.

Okay, you were like, so they didn't ask you to stay on.

Adam Callinan (35:23)
No. Well, they wanted us to, but it was not, it was a non-starter.

Alexandra Cristin (35:28)
And

so I wish that was my biggest mistake was staying on. I look at, know, my company was, Glam Tumors was acquired in 2019. It's 2025 now. I stepped down at the end of 2022. So basically all of 23, 24, 25, I've been free from this company. I don't want to say free, but it was a ride. So I think my biggest mistake after the acquisition was simply staying on. I should have done a three or six month transition.

and I should have walked away. For whatever reason, I was very excited by the idea of learning. I was very excited by the idea of being involved in this billion dollar corporation and working with big investors and learning. you know, I really took on the challenge. And so I went from entrepreneur to a corporate employee. And although they allowed me to do whatever I wanted the first year, like I was spending their money left and right. They...

I spent 200,000 on a website. was ridiculous. The things that I shouldn't have done, they really let me get away with and it was wrong. It was not good. But spending money, now I have their money. I'm like, yeah, 200,000 on a website, 60,000 on a photo shoot. Yeah, like awful. Not good. I did end up doubling the sales for them in two or three years. I doubled the revenue. Sorry, the EBITDA, the profit. And so like it was going good.

but then they started acquiring more brands and their organization started getting even larger, very complex. And I technically have this boss and it didn't go well. didn't, it didn't go well. She was a, you know, third, a 20 year corporate employee, never been an entrepreneur. And she was in charge of all these founders and entrepreneurs. And it was, we were all bumping heads, you know, between the way you run a corporation and the way that founders see the vision for their business. And so that.

It was a huge learning curve working in this corporation. And it was my biggest mistake because it really killed my entrepreneurial spirit. It took me years to recover and I was burned out and I didn't realize it. So it's like already I was burned out from growing it from, you know, zero to over $10 million by myself with no experience. But then I stayed on and took it from 10 million to 22 million in another three years. And I was literally exhausted. Like I just,

I just couldn't do it anymore. So ended up deciding to leave end of 2022. I had just had my second baby and I said, this is, it's time. It's time for me to go. It's time for me to part ways and ended up stepping away 2023. Luckily for me, I only had a two year non-compete. So I'm actually getting back into the extension industry. But long story short, during those two years, it took a lot of time to just heal from that burnout.

and the corporate life. know, corporations are ran a certain type of way and they have to be when there's that amount of money involved. And so it was a lot of unlearning from the corporation and I started a new startup and it didn't go the way I wanted it to. Like I ended up going to Harvard last year, did a innovation course. That's really what I do well as a founder. I think it's very important to know what you do well.

and I'm really good at product development. I'm not great at operations and P &Ls, right? And so I went, studied innovation, and one of the case studies that we looked at at Harvard was OnStar lost money for seven years, but in its eighth year of business, after losing money, continuing to put money, put money, putting money, it took off and they made all their money back, and obviously it ended up working well. So it reminds me of my startup, Tribe 35, which,

I was just trying to fill my time. Like I went from running this $22 million company to doing nothing. I mean, of course I have my kids, but they're in school. Like they have their own life. I'm an entrepreneur. I'm here to generate, to create. Of course I started a foundation and I filled my time up with as much that I could, but I love the game of business. For me, it's fun creating a product that customers need, that they love, that they appreciate. That really fills me up. It just does. And so.

Yeah, the last couple of years have been eye opening for me and I feel like I've had my most growth in the last years of stepping away, reevaluating everything, throwing half a million dollars into a startup and it not going and I'm like, my ego is bruised. And so it's, it's been a journey to say the least.

Adam Callinan (40:01)
What would you do, knowing what you know now, what would you do differently with Tribe 35 if you're gonna restart it tomorrow?

Alexandra Cristin (40:08)
So I started Tribe 35 with too much money. I think we need to put a cap on. I don't care how much money you have. I think we should put a cap of like, hey, this is more research. I would have done more research of like how much it costs because I truly believe because there's so many competitors in the athleisure space that I needed more than the half a million that I was going to allocate to it. And really I said I was gonna allocate 250K then ended up being 500K. And I'm like, if I keep going, it's gonna be a million dollars. And so I think

Looking back, I started it when I was doing too much. Like I had, I still was in Glam Seamless running at a CEO. I hired my best friend to come and run, create this company for me. I was directing her on the weekends of like, do this, do that. No, I should have waited. I wasn't ready for tribe 35, right? And because I wasn't ready and because I wasn't paying attention, money was just flying out the door.

I told my best friend, hey, here's 250,000, just figure it out. Like, and obviously I didn't like put 250,000 in her bank account, but it's like, I'm like, yeah, we have a budget. yeah, it's fine, hire this person. yeah, go ahead and do that. And it just, I was doing too much. You need to focus. I needed to focus and I'm running my nonprofit and I'm having a baby and I'm still the CEO of Glam Seamless. And I'm thinking, well, I have the money and the experience. Like, of course this is going to be easy, of course.

Did we create an amazing product? Yes, to this day, there's no other legging that's for my body. Car customers are coming back two and three times. So that's the reason why Glamsemos was acquired because the repeat purchase rate was so high that it was such a profitable business. Same thing with Tribe. I've built an amazing product. Customers are coming back. But also what I would say is I'm just not that passionate about clothing, right? Like I'm just not. don't care to say there's too much fat.

I'm not passionate about it. And so it goes back to my original theory of like, when it's passion for me, it doesn't feel like work. So I'm able to give it its all, if that makes sense.

Adam Callinan (42:15)
It does. I think that there's, I mean, there's a lot, an incredible amount to be said about being passionate about what it is you do. I don't necessarily, from my experience, like bottle keeper, I wasn't passionate about stainless steel beer bottle cozies. Like it was just a thing. I was passionate about the building of the thing and the strategy and the process and the structure and doing it in a really unique, different way. That is what I loved about the company.

Alexandra Cristin (42:26)
Yeah. Yeah. Yeah.

Yeah.

And

where did you get that from? Where did you have the insights? Did you have a corporate job before that? Like I didn't see, like, where did you get the strategy and the insights to grow Bottle Keeper to what it was?

Adam Callinan (42:43)
you

⁓ so part of it was experience and part of it was also scar tissue from that experience. It was, you know, I had been, I was a partner in a company before that, that was a medical health tech thing. I was an employee of a company before that there was a medical device company, ⁓ that I had an incredible amount of scar tissue coming out of, cause it was brutal and psychotic. ⁓ I learned an incredible amount of what not to do. And so it was from that experience. And then I sold out of the medical comp, the tech company in 2000.

I'm sorry, 2013, we started in 2008. It was going into Bottlekeeper. That's what I created those guardrails from. It like, I'm never gonna do that again, so I'm gonna go build a company that has zero employees. I wanna be able to operate it from anywhere in the world with internet. And that was just a guardrail.

Alexandra Cristin (43:35)
And how many employees did

you all have? Like what was the most revenue, if you're allowed to say, like what was the highest revenue ⁓ bottle keeper got to? And how many employees?

Adam Callinan (43:44)
We did. So our employee count varied. You know, it's funny because like Pentane is built on this system that I created at Bottlekeeper that my cousin and I ran the company on, which was all about understanding how to pull the right lovers around ad spend and understanding where the profit is coming from. So you can go do more of that thing to get more profit. And but a big piece of that is understanding how adding expenses to your business impacts the business. Because like if you hire three new people, you have to pay for those people. And if you

don't pull the right lever in how you acquire customers. You're not going to drive enough revenue at the right margin in order to pay for those people, which means you're going to lose money. Right? So we had all those things and I still completely threw it off the rails. I like just pretended it wasn't there when it was actually the year after shark tank. We did in 2018, the year of shark tank, we did 13 and a half million. had four employees in 2000. We made about 1.8 million in net profit that year.

Alexandra Cristin (44:44)
great.

Adam Callinan (44:44)
Going

into 2019, I went, this is gonna go on forever. Hired some people, opened a suite office with an awesome roof deck in El Segundo, right on Main Street, it was awesome. Spent a ton of money, hired amazing people. But it like went away from the ethos of the business and I like stopped listening to the data that I wrote the math for. And that year we did the same, we didn't grow, we did the same amount of money and we lost a million and a half dollars. We literally gave all the profit back that we made from the year before.

And it was like a forced reset. I had to fire people that I really liked. I had to get rid of an office. That was really nice. But it saved the company and we got bigger and eventually got acquired a couple of years later. it was a, you know, eye opening moment to like literally eat the system that I created. yeah.

Alexandra Cristin (45:32)
Yeah.

And so your system is built on being very lean and profitable and not having a lot of employees.

Adam Callinan (45:38)
No, it's built on, literally, it's built on creating an understanding of how, like, look, there's tons of different types of software, right? We have FinTech software, we have tons of MarTech software and AdTech software, marketing, advertising, financial tech. In order for marketing tech software to actually be useful, it has to have information that exists in the financial side of the business.

And that doesn't exist. So we created these systems using math that took an understanding of how the business spent money on employees and health insurance and cost of goods and product and shipping and fulfilling and advertising. And it takes the underlying math from that and applies it into the marketing side of the business, which is like, depending on the size of your company, you might need to spend, you've set your ad budget arbitrarily at 10,000 a month.

you might need to be at a 27 return on ad spend to get to break even because it's not enough yet.

Alexandra Cristin (46:38)
arbitrarily

and it's so arbitrarily so before acquisition I just was spending spending spending and then when I finally got acquired and now we had a CFO and a PNL and they're like 21 % that X and I'm like what what is this you know so I I learned how to manage a PNL but I was just spending so much money I don't even know how we got acquired the way that we did because I'm like looking back I'm like holy hell like

Their accounting was much different than my accounting, right? And then you're talking about a parent company with like, they have their own charges that they're putting on my P &L for, you know, group services. And so very interesting. Yeah. After the acquisition of like looking, I love what you're building here at Pentain because I think it's so needed. I mean, I want it for my next hair extension company because we just grew bigger. And to your point, it's not about the optics and the employees and the great office. And like, those are fun, cushy things.

They do really eat into the profits of the business. the end of the day, we are not in a nonprofit. We are a for-profit organization. So I have a lot to learn. I look at, I've created something new in the hair extension space. The first ever innovative product. I can't say yet, but I'm launching in January. I've worked the last year on it. My non-compete ended this year. And I know how much I'm going to scale and how big this company, I mean, I hope. like, I hope, but I feel it in my soul knowing what I know about.

Adam Callinan (47:55)
Amazing.

Alexandra Cristin (48:04)
extensions where the industry is. And I think about scaling it. But the one thing that really keeps me up at night is I'm like, how do I not burn out? How do I keep it lean? How do I not spend too much here or there? And so those things do keep me up at night because now ignorance is bliss. And so before the acquisition, like I'm just spending arbitrary to your point, 300,000 a month in ads. Yeah, it makes sense.

No, my parent company, then I went the opposite. So ignorance is bliss over here, pre-acquisition, then get acquired. And I'm reporting to a CFO who has like 30, 40 years experience. He's like, Alexandra, we've got to reel this ad spend and we've got to, you know, this is your CMB. I'm like, CMB, you know, compensation benefits. I'm like, I'm learning all these acronyms. I'm like, my goodness. So it was a learning curve, but I think founders and entrepreneurs don't always have a strong grip on the PNL.

terms and like we have a financial fiduciary responsibility to this P &L and yeah I'm super interested when I saw Pentain that's why we had those conversations like six months ago but I wasn't ready because I'm in development but how you run the company is so important it's not just about the optics of this is an amazing brand sales are 20 million dollars we have the best office it's like at the end of the day what is the bottom line here right because when that up

Adam Callinan (48:58)
Yeah.

Alexandra Cristin (49:28)
⁓ When that acquisition offer comes, you want that profit to show the highest, right? They're gonna purchase you most likely, unless you're in an industry like I was where sales are booming, booming, booming, there's a roll up. They're going to pay you off of your profits and your clean books. So if you don't have that, it's done. You're not gonna get as much as you could. And looking back, I could have sold Blam Seamless for three or four times had I had had a system like this.

I could have sold for more because to your point, just, the business gets too bloated and then we can't be profitable. So, so much to chat about.

Adam Callinan (50:08)
Yeah,

no, I know. mean, that to me, that's the whole point is like, most people start a company because they have an idea and they create that thing and then people start buying the thing, which is awesome. And you're like, cool, I'm CEO. I mean, like that, that's it. And that's a beautiful, amazing thing. There's so much magic in that. But there is this side of the business that we can't pretend is not there. I mean, you can pretend it's not there, but it's going to bite you at some point. You might get lucky for long enough. And that's and that's OK. But like if we can just take that off the shelf.

Alexandra Cristin (50:30)
Yeah, it is. Yep.

Adam Callinan (50:36)
and just deal with that with, you know, math and tech, let you focus on building and let you focus on product and customer and the things that that's why we start companies. It's not to deal with financial stuff. It's because of the customer and the experience and you know, that that part of the business, but so shifting gears a little bit, you know, you have this amazing upbringing that, know, may at the time may not have felt amazing, but looking back at, mean, it clearly made you who you are. Again, that's a

Alexandra Cristin (50:46)
Yeah. No.

Adam Callinan (51:06)
chapter, that's a very important chapter in your book. Are there things that you do today or practices that you have today, you know, that you've carried forward that like help you deal with, you these can, you're still doing it, like still operating as an entrepreneur, help you deal with these ups and downs.

Alexandra Cristin (51:24)
From my childhood? Is there anything from my childhood?

Adam Callinan (51:26)
anything that you've developed over the years or you know are you are you a journal or a meditator uh you know religious exerciser like everybody generally has something

Alexandra Cristin (51:32)
Yeah. Yeah.

Yeah. For me, I'm definitely into the journaling. I'm not so much a meditator, although I wish I was. The studies are there about what meditation does for one in their brain. ⁓ I journal a lot. And I also just go to this place of inner peace, of like, I'll put on the Calm app. If I'm having like a really tough time in life, I will put on the Calm app and I will, you know, distance myself from the phones and the computer and everything.

You've got to step away because in this day and age, we're so overstimulated with being connected to online that it just, you don't realize it, but it has a crazy effect on you. You just start to not feel well. You're overstimulated. You're not performing at your best. So I have these periods throughout the year where I literally two to five days, the phone is put away. At the top of January last year, I went to a retreat, an Ayurvedic retreat for five days, completely left my phone. I told my family, know exactly where I am here in Santa Monica, if you need me.

call them if there's an emergency, but this is where I'm at. So I think disconnecting, journaling, and being honest with oneself is just key. Because how are we going to continue to have the vision to be the leader that we need to be for an organization if we don't step away and recalibrate ourselves? So those are my go-tos. Stepping away, journaling, that helps me come back as a stronger leader.

and a stronger visionary, which we all know that that's really what a company thrives off of.

Adam Callinan (52:59)
Yeah, building that that step away into your life is magic. I I have all sorts of things that that forced me to step away from a computer. Now in a software company, it's clearly very computer heavy and that is not good for my brain for more than like an hour or two at a time. You know, when you, you talked about the experience after the acquisition and sort of like staying really busy and in hindsight, maybe that wasn't such a good idea. I did that as well, like post acquisition, I had a performance coach.

Alexandra Cristin (53:12)
What are some of your things? What are some of your things for you to step away?

Adam Callinan (53:29)
The timing was just kind of fortuitous who was helping me through the transition and the one thing he told me and he had coached some of the most famous entrepreneurs and athletes that we've I mean that have ever existed at least in our generation that he sees across as a theme for these people is when they're transitioning be some between something significant that they they never want to take time to let that thing process. They always want to go out like

just do it again, jam a square peg into a round hole over and over and over. And I obviously felt that like transaction closes. I stay on for six or seven months to oversee. And then I'm like, what am I gonna, you know, a week of doing nothing. like, I'm gonna lose my mind. what am gonna do now? And his name is Dr. Jeff. He's like, no, you gotta sit still, pick up a hobby. So I started doing woodworking. Like I figured out, I know, like I'd never done that before. Like I built a mud room and my kids beds and remodeled the kitchen. And I figured out through that process that I,

Alexandra Cristin (54:06)
What's Yep.

I love it.

Adam Callinan (54:25)
function dramatically better when I have something in my life that I'm building with my hands. So like I make old wooden signs like, ⁓ so I have to have something like that. So right now I'm rebuilding a 1994 Land Rover Defender, like this old awesome truck, because it's like a thing I can just in the middle of sitting at a computer for three hours, I can go into the garage and spend an hour doing it. And when I come back to the computer, I am 90 times more productive.

Alexandra Cristin (54:32)
And that looks so, I love that with the light behind.

So cool.

Adam Callinan (54:54)
I have to have something like that in my life that I'm creatively with my hands.

Alexandra Cristin (54:58)
That's awesome. It's amazing.

Adam Callinan (54:59)
But

this has been super fun. Where do you want people to find you? Find Tribe 35 if that's where you want to direct them or maybe even the next top secret thing.

Alexandra Cristin (55:07)
Yeah.

Yeah. The next I'm not announcing it yet, but it's coming soon. It's going to be huge. So I'm on LinkedIn and Instagram, Alexandra Cristin. So those are the two main places you'll find me. C C R I S T I N and yeah. Any entrepreneur out there?

Adam Callinan (55:12)
You

Alexandra Cristin (55:27)
Really take the time to understand your business and continue to invest in yourself because that's where the greatest returns are when you are well, when you are feeling good. Everyone else feels it. Everything else flows and follows. And that is the magic of like putting oneself first so that everything else, you you cannot pour from an empty cup. And it really is, it really is true.

Adam Callinan (55:50)
It's beautifully said, completely agree. Thanks a ton for coming Alexandra. Appreciate it.

Alexandra Cristin (55:54)
Yes, thank you.

Thank you so much. Okay, so I'm supposed to stay on here, right?