David speaks with Christine Carrillo, an executive coach for early-stage CEOs and founder of The 20-Hour CEO. Christine has built three companies generating over $200M in revenue and now helps founders build lean, profitable businesses without burnout.
They talked about:
🏚 Growing up in poverty and becoming head of household at 14
🛠 Navigating trauma, burnout, and building resilience
💡 Why freedom, not money, was her ultimate definition of success
🚀 Starting and scaling VC-backed and bootstrapped companies
🧘🏽♀️ Rewriting productivity rules with the 20-Hour CEO
🧠 The mindset shift from survival mode to CEO mode
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📄 Show notes:
[00:00] Introduction
[02:20] Growing up in survival mode and becoming head of household at 14
[05:00] Climbing the career ladder while carrying the weight of the past
[07:42] From corporate burnout to first-time founder
[10:29] Building and exiting multiple $100M+ businesses
[15:29] Rethinking success and why time freedom became the real goal
[24:06] The leap of faith - and what pushed her to go solo
[30:36] What she got right and wrong about startups
🗣 Mentioned in the show:
The 20-Hour CEO | https://www.20hourceo.com
Butler Health | https://www.butlerhealth.co
Techstars | https://www.techstars.com
Kaiser Permanente | https://healthy.kaiserpermanente.org
McKinsey & Company | https://www.mckinsey.com
Deloitte | https://www2.deloitte.com
👤 Connect with Christine:
Website: https://www.christinecarrillo.com/
Twitter: https://x.com/ChristineCarril/
LinkedIn: https://www.linkedin.com/in/christinecarrillo
👨🏾💻 About David Elikwu:
David Elikwu FRSA is a serial entrepreneur, strategist, and writer. David is the founder of The Knowledge, a platform helping people think deeper and work smarter.
🐣 Twitter: @Delikwu / @itstheknowledge
🌐 Website: https://www.davidelikwu.com
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📖 Free Book: https://pro.theknowledge.io/frames
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📜 Full transcript:
Growing up in survival mode and becoming head of household at 14
David Elikwu: So you were talking about your background and you were saying that you came from a food stamp household. You were the head of your family at 14, with side hustles to avoid eviction living in a drug-infested projects. And now you've built three successful businesses. You've been married for 26 years. You sent both of your kids to private school and college, and you were talking about how you broke the cycle.
And what I love about this tweet is specifically, this is kind of your, your hero's journey. I don't know if you are familiar with Joseph Campbell's Monomyth, but you know, the hero's journey is essentially just the trajectory of the hero's life.
And I know I'm describing you as a hero, but the point is I think it [00:03:00] sets a great trajectory that I'd love to talk through. So maybe we could start from your early background and your upbringing and what that was like, and then we can talk through the process of breaking the cycle for you.
Christine Carillo: What's funny to refer to it as a hero's journey. I grew up in LA. My mom had me when she was very young. She was 16 and my father was very violent and alcoholic and they divorced probably when I was maybe nine, by the time I was 14, I ended up well between 10 and 14. We moved into the hood, the real hood you know, deep, deep hood. You see people walking by with eyes of wild desperation and, moms are willing to turn tricks to feed their kids. It was a really rough area to grow up in. And my mom was severely depressed at the time as well.
And so when I was 14, I came home one day and found her in the same spot that, you know, when I [00:04:00] had left and she had soiled herself and had a blank stare there was saliva dripping down her mouth, evidence of another drug overdose. And that was the day I was promoted to head of my household.
And so at 14, I took on the responsibilities, both financial and emotional to support my mom, and my four siblings in addition to me.
So between 14 and 19, I was just overfilled with everything I needed to do to, you know, I went to school before school started. I had to drop off my sisters and brothers at daycare, wherever we could get them. I had to have multiple jobs to pay the rent and clean and all of those things. So by 19, I was functioning like a proper 40 year old.
And from there I ended up something I never thought I would do, but at 19 I ended up meeting my husband who was a street artist. And he was 25 at the time. We ended up getting married. We've been married since it's been [00:05:00] amazing.
Climbing the career ladder while carrying the weight of the past
Christine Carillo: And since that time, for me, one of the things I didn't realize until now, I guess, growing up, I never had any money and I was always in survival mode. So I leveraged time. That's all I had. So I maximised my time as much as I could and I was reading whenever I could learning different things, whatnot.
As my career sort of flourished I ended up doing the same thing like, many of us, you know, started out at the very bottom. You know, I was a project manager and then I, I had studied and become a software engineer, and then become a software engineer and kinda just kept getting better at my job. The downfall with that, that I learned you know over the last maybe seven years, eight years was that I was getting better at my job and saving time, one thing was I needed to be validated. I grew up in an area where people looked at me funny when I walked into a store. So at work, I didn't work with people [00:06:00] who look like me very rarely.
So I wanted to also prove to them that I belong, that I was good enough to be here. So I really wanted to just be so good at my job. And so I probably, I could outwork anyone because of, I would say some of it I thought was being clever, but what it really was was leveraging my time again, which is the same thing I did as a kid.
Then I started to fill it back up, which was weird, you know, like I do my job and maybe a third of the time, and then I'd volunteer to take on two other people's jobs and I'd get the gold stars. People would say, great, I didn't get promotions and I'd be exhausted at the end of the day. And then I'd figure out how to be efficient again or automate and streamline those three jobs and add on another two.
I didn't see the problem with that at the time, but now that I look back, it's like, wait, what what's the point of getting really good at this if you're just going to fill up your time right back up.
But I guess, you know, that's from being an engineer in corporate [00:07:00] jobs and then moving into executive roles over time. I landed at the last place, which was Kaiser. I had been brought in to take on a really large initiative for them. I was coming into flip Medicare is what they call it. Basically at that time, Kaiser really had a bunch of home grown systems and was losing like $7 billion a year. So I came in to help them streamline that, and run the business and the tech side of the project. It was one of their first times they'd brought in someone from the outside. That left me disappointed with how the inside of a insurance company worked.
From corporate burnout to first-time founder
Christine Carillo: And so I naively left Kaiser and started my first company, which was called Humanize health.
And what we did was basically the same thing I did for Kaiser, but for many insurance companies on many different types of initiatives with kind of like, the MacGyvers of health insurance. and I really [00:08:00] thought that if I can show these insurance companies how to implement these initiatives faster at a fraction of the cost that Deloitte or McKenzie was charging that those savings would roll down to their members. Very naive I know. I was very young. And I did that for five years.
And then one day I was at a dinner party and a friend asked me, he was a film director, we were in LA and super sloshed. And it was like, Hey, you know health insurance, can you help me figure out why I'm getting screwed? Like, why am I paying so much? It doesn't cover anything. And I was like, first I was insulted. I was like, listen, I've got a big kid job. I don't know about your insurance problems, you know, but the more he pestered me about it, I started to look into it And thought, well, this is kind of crazy. I mean, this guy can sit here and complain about it over dinner, but doesn't really need to take action. He can afford to blow three grand a [00:09:00] month on just like, I don't know why it's not adding up kind of thing, but the majority of the world doesn't work that way.
And so I started to look into why was he getting screwed? He had the best insurance, there was through the producers guild. and then it was very simple. It was like, wow. He just never really looked at what he needed and what was offered and what was covered. And there was a lot of math involved and no one's going to do that. No one's going to take the time to understand all the different options you have, or you don't even know you have those options. So I ended up spending about two weeks on an algorithm in Microsoft access at the time and built out my second company, which was a consumer marketplace that helped people get the best health insurance and know the value and the price of it ahead of time.
I ran that for five years, almost six, maybe.
And then it was VC backed. I raised 30 million in capital. It was all the things that I was asked to be as [00:10:00] part of the tech industry, I guess. Then I started a, my current company right now, or one of the ones I run now is called Butler health, which is a mental health platform that matches people with therapists based on a dating app algorithm.
And that company, I, I've ran for close to three years and I'm now hiring a CEO for it. And I think that brings me to where I am now. I run other companies as well, but this is sort of like how I've come to here.
Building and exiting multiple $100M+ businesses
David Elikwu: I'm so glad that I gave you the breadth to go through all of that because there's so many threads that I want to put on. And so many places that I'd love to dig in and, and ask further questions. I'm thinking maybe going back right to the start. I know you were talking about your early background and I think, first of all, it's really touching to hear about everything that you have gone through, and I'm really interested to know, as I'm sure you can imagine having come from where you've come from and having been where you've been, not everyone makes it out of that kind of situation. And [00:11:00] everyone is put in a situation where they need to be uber resilient, and is able to rise to meet that challenge. And not only is able to do that, but it's able to carry the burden of managing a household, particularly at a young age and being able to take care of siblings and being able to take care of your family and keeping a family in a home and doing all of those things.
So I'd love to know maybe first, what did you need to tell yourself? Was there some kind of internal narrative, what had to change in your mindset perhaps to be able to deal with that additional responsibility?
Christine Carillo: You know I guess growing up seeing, there was a hell I lived in inside my house, right. My dad came home and was incredibly violent with anybody and everybody. And so a majority of the time I stood between him and my mom and try to, you know six, seven protect her. And then he'd beat me up and what have you.
But I think on those days, growing up like it became normal. That [00:12:00] just is what happened every night. And I was preparing every night for when he would come home and this would happen. And so part of that preparing, so weird, but I used to read, I read a lot and that's all I did. I was in the library all the time, and so I read about other families, other kids, other, just other stories. And there was something about that during that timeframe that helped me see that, even though this is what I lived in, like there was something we didn't have to live this way. And we did all the normal things. I think that, I don't know if they're normal, but they felt normal to me, but that you would do in a household like that. My mom would run away, we'd go to a women's shelter. He'd find us. We'd come back. It was like this repeated thing.
By the time I was 14. I mean, I was heavily depressed. You know, there was no way out of it, but it didn't really show itself, I guess, as proper, I tried suicide. I've failed miserably at it.
But by the time I saw my mom [00:13:00] and the, you know, when I walked in that day, I guess it didn't have a choice anymore. You know, it all had to be wrapped up and put away. And now it was, I had, I didn't have a choice. I had to take care of us, but it was also the first time I felt a sense of control in my life. And maybe that's the thing that changed for me is that it was like, okay, she's now she's not the one making decisions anymore. She can't. And as weird as it sounds, I was only 14. I don't know what the hell I was doing, right. But for some reason that gave me just a glimmer of hope or it was like, we can do this a different way now.
The other thing I think is that, and I still do this today is, every night, hearing him beat her, what would start to happen is I'd sit in my bunk bed with my sister next to me and I'd start to say, okay, at least today we ate. We have a roof over our head. When I was at school, I got to play with Emily. And I'd look for things as I would hear him beating her. And it was just, I [00:14:00] must've been self soothing, that has continued throughout my life. So I do go to bed and wake up every night saying all the things I'm grateful for. I think that helped a bit with, you know, and then, you know, having the responsibility just put on you. I guess you have a choice, right? You take it or you don't. I didn't feel like I had a choice. I was my mother's best friend. And so there was already a burden of holding all of her. Everything, all of her rage and depression and everything that now it was like, I can't let my siblings down. I can't.
I don't know that I was as concerned about her to be honest, but I was very concerned about my siblings. So there's something there driving that.[00:15:00]
Rethinking success and why time freedom became the real goal
David Elikwu: That's so powerful. I think what's funny is I know I referred to it as a hero's journey at the beginning, and I wasn't expecting it to be so accurate in some ways. And what I also wasn't expecting is go through what you went through and I won't attempt to equivocate at all, but even in some of what you shared, I was just thinking of so many parallels to some of my experiences as well and how I really do think that, so as an example and even part of why I asked that question [00:16:00] was, I remember I was quite young.
So I, I grew up in Nigeria. I wasn't born in the UK. We came here, I came with my family and, when we lived in Nigeria, so a lot of immigrants that you get here, not a lot of immigrants, but a lot of friends that I have that also came from Nigeria, have homes like they were living okay back in Nigeria and then came here. And obviously life is a bit more difficult here because you have less money and all of those things. But even when we were in Nigeria, we didn't, it's not like we owned our own home. We lived in a small flat. And I remember so, when I was quite young, we had armed robbers at our flat but my parents were out, so it was literally just me and a babysitter. And I remember just this feeling of incredible helplessness in a way that I hadn't previously had when you're just standing there in a room and there's all these guys with guns. And it's not like you had much before that, and then they just take everything else that you have anyway.
I really do remember like that [00:17:00] was something that was on my mind for years after that. And just this feeling of wanting, I think part of what you mentioned, which is this sense of control, and wanting to feel as though you can be in some ways the master of your destiny and you can have things that are within your control.
And I think that is part of maybe a push towards entrepreneurship, particularly the more that you learn about the world and how very often people are helpless in the situations that they are in and how very often people do not have the means to be able to create their own destinies and to be able to set their own time and set their own schedule and find their own trajectory as well.
And I think even, as I came to the UK as, even the area that I grew up in, I was in a fight from my first day of secondary school and pretty much every day or every week until I eventually got kicked out of that school I think I had almost 400 incident slips in about two and a half years before I had to move to a different school there was just so much going on, but and then this was the other [00:18:00] thing that really touched me from what you were saying as well, because that was also when I started to read a lot of books and I don't know if it was the same for you and your experience, but what I know for me was that it was really a sense of escapism because I felt as though there's a lot of pain at home and there's a lot of pain outside of home and the only place, there was a local library that was near my house and it's the only place that, you know, nobody that I knew would be, and it was just a place that you could just go and you almost stumbled into reading and you stumbled into just being able to escape into somewhere else that's different. And, as a result, you end up learning things and you end up discovering things that you might not have otherwise.
And I know I've been rambling and monologuing at you for a while, but this will link to my next question, maybe, which is so I know that you went through all of that and then you're starting to build your career. But even from those early years, I know that particularly people from minority backgrounds and people that are, you know, underestimated or under resourced, don't always [00:19:00] see examples of what success can look like. And I'm wondering for you, did you have an idea of what you wanted to be as you were studying and also as you were starting the early years of your career, did you already have it in mind that this is where I want to get to, this is what I want to be, or were you very much figuring it out as you went along?
Christine Carillo: No, I, everything was survival for me. So the hardest part of my adult journey has been being able to know when I'm not in survival anymore. Cause I'm really good at survival. I'm like a trained sniper now. I'm in chaos. All that stuff is no big deal for me as an, you know, which is oddly what made me gravitate to these very, very hard startups. And they weren't even easy ones. I mean, I went and did crazy stupid things like, health insurance, let's go fight them in California, change how it's sold and do a marketplace, and be VC backed. Like I now know that that was almost recreating the environment [00:20:00] I thrive in, right. It was I'm good at that but not good for me.
You know, for me, what felt like success was actually being a writer, but it also felt like something I could never do when I was a kid. That's all I wanted to do is to be a writer. From where I grew up, no one wanted to be a writer, number one. But number two, if you did, it was one of those things, like similar to my husband who was an artist where you were looked at like, well, you're never gonna have any money. And because I grew up so poor my goal was survival, not just me, but my siblings. And then, you know, I had my mom, I had to still take care of.
So I was looking for how can I support myself and all these people. That was like the first sort of things that were always in my head. I don't know that I was thinking of success back then. It was so survival focused I didn't really, you know, kind of come into play. I feel like my twenties, I was married and I have two kids, right. And that was when I had my kids, I think was the time where I [00:21:00] decided to let go of the survival mechanism because it was, I mean, it was, everything was fine.
And then was the time I started to look at. What do I want out of this? Like, wait, what can I build? What do I want? So I didn't really have role models I guess, other than what I read in, or I didn't know people who were successful, but we did this crazy thing where in LA it's hard to send your kids to public school. It's, I went to them and they're just, they're awful. So anyone who's can, send them to private school, and it's ridiculous. There's so many private schools in LA. It's ridiculous, right? So we lived in an area called Pasadena, California, where there was, there's just so many there and so everything we did in the beginning was giving up for us to send them to private school. And that actually was my first glimpse at a different world. And I mean, you could, you could argue I was still a kid myself, right? I mean, I was in my mid twenties now at these private schools. And I'm meeting people that are in their late [00:22:00] thirties, mid thirties you know, they're film directors, they run Ad agencies, with jobs I'd never heard of. And I'm a software engineer, but these times I'm still working. And I think in the early years, I don't remember a lot of people, they were small shops, you know, they weren't like these big companies. I think that were where I could look at people and say, oh, I want to do that. But these people gave me a different way to look at things. It was, you know, strange to see how their parents helped them and just their jobs.
So I think that kind of taught me well, I guess the other thing was, they were always there after school. Always there after school. And I thought, how the hell are you doing that I'm working my ass off. Like, how are you here after school and, or lounging for coffee in the morning? And so that my idea of success started to turn into freedom, which is what I never had growing up. Everything was just so, there was no control, but there was also no choice. Everything was forced on me.
And so freedom for [00:23:00] time was what I went chasing. And I guess that's where I, that's how entrepreneurship started is I thought if I, if I chase this, I can spend time with my kids whenever I want.
David Elikwu: I love that. And I think this kind of leads into that, I think maybe I'll ask two questions and you can decide to which to go down. But I think they're very linked, which is you were talking about this element of security and wanting security, needing that sense of security and being very reliant on survival and having to survive.
And I think what can happen to a lot of people that feel like they have to survive is they can fall into wanting the security maybe too much and not being brave enough to maybe step out and go into entrepreneurship as you did. And I'm interested to know what gave you the confidence to push out of that. When you may have already been in quite a stable job. And quite a stable career, you've worked your way up. You've had some success.
What makes you think, not just that I know that you saw some problems that you could solve, but gave you the courage that, you know, [00:24:00] it can be you and you could go out and solve those problems and you think you can really have this huge impact in the world
The leap of faith - and what pushed her to go solo
Christine Carillo: it was a terrifying leap to take because you're right. I had gone to a stage where I didn't, I didn't know anybody who had been there from where I came from. But what happened was, I guess it's the same repeated pattern, right. Once, you know, and you've seen where you don't want to be it's hard to unsee it, no matter what's given to you, no matter how much money, no matter what the title is, no matter all of that.
And you know, at Kaiser, there was a strange situation where I was asked to do something that was unethical because I had a very large budget and I chose not to do it. And I got the wrath of the management team who had all worked together for over 15 years, you know? And like I said, I was very naive at the time thinking that I could make a change, but the bigger part I think was I felt suffocated there. I, I mean, I show up to meetings [00:25:00] sometimes and you know, I wasn't required to be in the meeting, but maybe I had to go from LA to DC. My boss would tell me the night before and my whole house would flip upside down. I mean, like we had to figure out now who is picking up the kids. I mean, it was just so unfair, but I'd go. And I'd get there. And there was this one time I got there. I think this was the breaking point for me. And my boss was in a small conference room and I walked in and it was just her and a you know, Mike and I was like, wait, what's happening? Where's the meeting. And she was like, oh, I just, I thought we could hang out here in DC. And it just, the rage I had that day. It's like, you just took me away from my kids and my family. And I'm here for nothing. You know, I could have done this on the phone.
So there were moments like that along with being asked to do something unethical, which I felt like, again, I was back to feeling out of control maybe, and back to feeling suffocated. And I didn't know I [00:26:00] was going to start a company, but what I did know was I couldn't be there anymore. And it was Christmas time. We just planned a trip to New York that was all paid for. It was our, one of our early trips with our kids. We didn't have a whole lot of money because all our money went to these private schools. So even going to New York was a massive deal. And I came to my husband and said, I, he knew what was going on. And he said, you know, if we have to live in a one bedroom and put our kids in public school, they would rather that than you suffer like this, this is crazy. Like you don't have to be there anymore. So I quit. I didn't know what I was going to do.
And I spoke with at the time there was a vendor, I was negotiating with, and him and I became friendly. And he said to me, you're going to go out and you're going to be offered all of these senior vice president jobs, and you're not going to have a problem getting a job. And he was right. I started getting offers within few weeks. And he said, but you you're going to do the same thing. You're going to realize you've already seen it. That, you know, you can't work for someone [00:27:00] else. You need to go out and work for yourself. Like you're more than capable. And, you know, gave me this whole speech.
And It really resonated with me, not just like the hype part of it, but the thing that he said where, kind of shitty actually to tell me this, but he said, you're virtually unemployable. He said, I see you in these meetings, you don't play ball. And they don't like that. And he said, people like you are virtually unemployable.
I had thought about my history at work and how much I would rise up very quickly to these roles. And then I would push back against the way maybe a company was being run because I would see another way. And I knew that my time was up maybe, or I'd find another job, and he was right. And I think that's the part that was the hardest to accept at the time, because I had these kids and I was the main breadwinner. My husband was just starting his art career. So sometimes he'd make a lot of money and the many times he wouldn't for months.
But so I took a leap and I quit thinking also that [00:28:00] actually a corporate job is not safer than paving my own path actually. They're determining my path. I started to really think about, wait a minute, they're telling me like, whether I get a vacation or not this year, the salary they give me determines my life, like how much I live it, the capacity I get to live it in. And I started to get really upset. Actually, it wasn't their fault, right. I mean, they hired me, but I was like, wait, what am I doing? This is crazy. You know, I'm never going to have those lounge-y coffees in the morning at school playground if I'm doing it this way, this is not going to work.
And my husband and I were really adamant about not putting our kids in daycare, so we were trying to always finagle and figure out ways that we were both present all the time. And it was a struggle, but after I left, about three weeks in, I was interviewing, I'd got job offers. And then somebody came to me and said, you ran this thing for Kaiser. Can you be a consultant for us? And I [00:29:00] said, yes, but I have my own company. And I did not. And I said to my company does X, Y, Z. And they said, okay. And I said, so your rate will not work instead. This is the rate we charge. I mean, it was all made up, you know, and I already knew the insights of how insurance companies worked anyway. So I knew the rate would not even make them flinch and they hired me and it was the first one. And I just kind of went, took a leap and sort of went for it. I don't know that it was confidence in myself more than that really wanting freedom. I was maxing out at how much I can make in a day, and that was starting to frustrate me. I was like, this is my max now.
And it was my max because I couldn't even do a side hustle because at an executive, you're working like a beast. It's awful, you know, and I've got kids at home. So I was like, I've got to find another way. This is not gonna work.
David Elikwu: And I think it very much comes back to control, which is what you touched on earlier. It's this idea that, you know, you can build your dream for yourself, or you can outsource it to a company [00:30:00] that you hope will build it for you, but ultimately they are building what suits them. And they are going to build this life for you that is serves their needs and serves the company's needs. and so if they want you to go to DC, if they want you to come here, if they want you to go there, you will be at their whim in exchange for a certain amount of money, which can buy you a certain lifestyle, but it doesn't buy you freedom and it doesn't buy you control ultimately.
So now you start your first business and obviously I know right now you're very much this champion of having a healthy sense of productivity, at least for your own lifestyle, you have the 20 hour CEO thing.
What she got right and wrong about startups
David Elikwu: What was the journey like of getting to this point? Because I definitely want to ask some questions about that, but I want to know in your first CEO capacity, when you started that first business, did you go into that already thinking, because I know you mentioned, you want to have this time with your kids. You want to be able to have this lifestyle. Was that something you were able to instill at the beginning or was that in itself a journey because I know a lot of people get [00:31:00] into entrepreneurship and some people very quickly realize that you are a worst boss than you are when your boss may have been in some situations, where now you might feel like, okay, nothing you do is enough and you have to keep working. You have to keep going, you have to, and a lot of people love that idea. They love that energy. They feed off it, even if it's bad for them.
Christine Carillo: Yeah, I think that's a great question. So the first company I built was everything I wanted. It was, I sold that my job was sales. I nailed board of directors that insurance companies we take on their projects or kind of swoop in after Deloitte or McKinsey, Accenture had sort of failed. And it was like, the project was almost dying. So we'd come in and save the whole thing.
I had a small team and they ran the projects. And at that time I had already learned enough to know what kind of company I wanted to build. I had seen people, you know, at previous jobs where there was one woman who got cancer, and I [00:32:00] remember how hard they made it for her to have cancer. I remember thinking that it was crazy. Like she can't take time off. She was worried about losing her job, which then would lose her insurance. And I just remember that was a big deal for me. I don't know why it stuck with me so much, but I didn't want anyone to work for me to have to worry about those things.
It was my first time outsourcing. So I hired, it started with a group of five people that I had worked with. And then I hired people off shore to help them. So basically my team was supposed to be fresh. They were to go into these exec meetings to only problem solve and lead meetings. Not update project plans, not take notes, not any of that offshore, people would do that.
So my whole job was sales and it was also in a industry that I didn't love selling to. I, you know, I love going into these meetings with these individuals. They, weren't the kind of people that gave me energy. And so I was bored, but it was the first time in my life. I got to be bored. [00:33:00] I took full summers off. I made a ridiculous amount of money. I spent enormous times with my kids and all the things that I wanted. I just wasn't intellectually stimulated. So I, you know, the company wasn't difficult to build. I think consulting companies are pretty easy to build.
The second company, however, really fucked with me because it brought me all of my past kind of came full stop infront of me. Needing to be validated, right. Needing to feel worthy. All those things came into fruition at my second company, because I was out of my depth. I didn't come from the Silicon valley world. I went into Techstars. It was very difficult. I was 39 with kids and a husband and everybody else, 23, 24, I was in health insurance. They were in VR and all the sexy, cool stuff, right. Like all of that was a challenge for me. And so I wanted to prove to them Techstars the investors who came in, everybody that I was good enough for you to invest in [00:34:00] me, that I was, I wasn't going to be your last bet. And that wasn't healthy because I grew that company at a explosive rate. You know, as I was growing it, I, I felt a, it was part of my identity, which was awful, right. So if it didn't succeed or failed, it meant I was as well. And then at what point during the company, you know, during the company's trajectory I had I mean, it was kind of great that this happened, I guess, but I had a concussion. I walked straight into a window. I thought I left it open. I lived in the foothills of California and it was closed. It was dark outside lights on inside. I walked in with just full force. Got a concussion and had to stop working and reading anything for six weeks. And that was the first time where I saw, first of all, like letting go is so hard, you know, and letting other people now run this company without me. But then the other part was like, I realized I had shame all of a sudden that I couldn't work as hard as I was [00:35:00] working. You know, I wasn't keeping up with what I was supposed to, whatever I had drank the Kool-Aid on. Then I came back to work and realized I couldn't work. Not the way I was before. I had these crazy migraines, that would come in and take over. I couldn't be in back to back meetings anymore.
So a couple of things happened to me. I wasn't fun to work for because I had internal pressure shame of not being able to work as hard. I was also feeling a lot of pressure that the faster we grew, the more pressure we got from VCs and that started to feel like I didn't have control again. They were trying to navigate me to build the company in a different way than I wanted to. And so there was a lot of back and forth around that.
One of the things that made that company explode was my ability to leverage time and, you know, automate everything and all that stuff. And we were so scrappy and we got it to grow, but it was not the right environment for me. I don't work well with I guess being [00:36:00] pressured to have to do something, but I don't feel I should do. And so all that started to build up over time.
And then this third company that I built was like a hybrid. So this third one, when I was starting it, a lot of the VCs I had before wanted to invest in this one and I almost did it. And then I rethought it and instead took a little bit of angel money from friends and peers, and then bootstrapped at the rest of it and kind of did what I wanted to do with the tech company or kind of how we started it, where I got to profitability really fast, very lean, small team. And then, you know, just sort of built it that way. Which was the perfect balance for me. I think the first one was, you know, I thought growth was revenue growth and VCs don't want that VCs want head count growth market. You know, it's a whole different ball game. And I just didn't know the game, you know, which was sort of where I ended up.
