David Elikwu speaks with Christine Carrillo, an Executive Coach for Early Stage CEOs, Founder of The 20-Hour CEO

Over the last decade, she built and led three companies that have generated $200M in revenue. She experienced everything from bootstrapping a business to $25M to building a hyper-growth VC-backed company to $28M ARR in under two years.

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👤 Connect with Christine Carrillo:

Twitter: @ChristineCarril

Website: christinecarrillo.com

📄 Show notes:

Early background and upbringing [4:10]

How did she start at the very bottom [6:14]

How did she start her own company [9:09]

What kind of success does she look up to? [22:12]

The idea of success started to turn into freedom [25:22]

Unethical moments she experienced [27:34]

She’s very fortunate to have a CEO coach [43:12]

A lot of pressure being extraordinary [48:30]

How are you as a CEO [51:24]

When she started Butler heath [1:00:19]

I hate managing people [1:03:15]

Prioritizing family over work [1:20:27]

🗣 Mentioned in the show:

Kaiser

Techstars

The 20 hour CEO

Butlr Health

👇🏾
Full episode transcript below

👨🏾‍💻 About David Elikwu:

David Elikwu FRSA is a serial entrepreneur, strategist and writer. David is the founder of The Knowledge, a platform helping people learn more and live better.

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🧭 The Knowledge

As a writer and serial entrepreneur, David Elikwu speaks with elite performers from a variety of backgrounds, unpacking everything there is to know about navigating the world around us.

This podcast is a catalogue of excellent data points. Join us each week for actionable insights to make sense of what matters most.

The Knowledge is a curated digest of the world's best ideas, drawing on insights from psychology, philosophy, business and culture. We explore tools, frameworks and stories that will help you navigate with clarity and cut through the noise.

Website: theknowledge.io

Podcast: plnk.to/theknowledge

📜Full transcript:

Christine Carillo: [00:00:00] 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. You know, I just, I'm like a trained sniper now. I'm in chaos. All that stuff is no big deal for me 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 I thrive in. Right. It was like, I'm good at that but not good for me.

David Elikwu: Hey, I'm David Elikwu and this is The Knowledge.[00:01:00] a podcast for anyone obsessed with learning more and living better. In every episode I speak with successful people from a variety of backgrounds to unpack everything they've learned about navigating the world around us.

This week I was speaking with Christine Carillo, who's an executive coach for early stage CEOs and also the founder of the 20 hour CEO.

And Christine has quite recently just become one of my favorite people just through her sheer force of authenticity. And it's incredible, even within the first 10 minutes of this episode, we dug so deep into her background and early childhood experiences. And I think we both shared and traded experiences that shaped our trajectory and approach to the world.

And Christine laid out the incredible story of being able to build three businesses that have generated over 200 million [00:02:00] in revenue, which is incredible by itself, but then also her experience with being burnt out and needing to take a step back and reevaluating her work life balance.

And I think even for myself, I was able to learn so much just from my conversation with her, about how to build and effectively manage small and scaling teams, hiring remotely. There's so much that it is packed into this episode. And I think you are really going to love it.

You can get the full show notes transcript, and also read my newsletter at theknowledge.io. And you can find Christine on Twitter at @ChristineCarrill.

If you love this episode, please engage with it. Subscribe, share it with a friend. And most importantly, please don't forget to leave a review because it helps us tremendously to grow the show and reach other people. Just like you.

Obviously in preparing for this conversation, I was looking at, you know, a bunch of your stuff [00:03:00] and your website, a lot of the things that you've talked about in the past, and I saw a great tweet that you had, and I just thought it was an excellent let me, let me get it.

I'll read it for you. 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 sets a great trajectory that I'd love to talk through. So maybe we could start from like your early background and your upbringing and what that was [00:04:00] like. And then we can talk through the process of breaking the cycle for you.

Christine Carillo: Yeah, sure. What's funny to refer to it as a hero's journey. So I, 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, and by the time I was 14, my, I ended up well between 10 and 14.

We moved into the hood, the real hood you know, deep, deep hood. Where you see people walking by with eyes of wild desperation and, you know, moms are willing to turn tricks to feed their kids. It was, 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 [00:05:00] that, you know, when I 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, my mom, my, and my four siblings in addition to me.

So between 14 and 19, I, you know, I, 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 and from there I ended up, I guess, something I never thought I would [00:06:00] 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 amazing.

And since that time, You know, 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 maximize my time as much as I could and I was reading whenever I could learning different things, whatnot.

And as I, you know, as my career sort of flourish I ended up doing the same thing and I 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 [00:07:00] over the last maybe seven years, eight years was that. I was getting better at my job and saving time. You know, 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 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, you know, 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, 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 [00:08:00] how to be efficient again or automate and streamline those three jobs and add on another two. And, you know, 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.

Right. But I guess, you know, that's from being an engineer in corporate jobs and then, you know, 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 [00:09:00] they'd brought in someone from the outside. That left me disappointed with how the inside of a insurance company worked.

And so I naively left Kaiser and started my first company, which was called humanized 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 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 they uh, 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 [00:10:00] 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 month on just like, I don't know why it's not adding up kind of thing, but. 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 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 [00:11:00] 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 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 you know, I was asked to be as part of the tech industry, I guess. I, 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 and that company, I, [00:12:00] 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.

David Elikwu: Awesome. 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 even going back right to the start. I know you were talking about your, your early background and I think it was it's.

I mean, first of all, it's really touching to hear about everything that you have gone through, and I'm really interested to know. Because 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 not 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 [00:13:00] 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: Yeah, I think you know I guess growing up seeing, you know 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 you know, I, I stood between him and my mom and try to, you know six, seven protect her. And then he beat me up and what have you.

But I think on those days growing up, like it was uh, it just like, it became normal. That just is what [00:14:00] 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 and it 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, I was heavily depressed. You know, there was no way out of it, but it didn't really show itself, I guess, [00:15:00] as proper, you know, I, I tried suicide.

I've failed miserably at it.

But by the time I saw my mom 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 not, 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, you know, for some reason that gave me just a glimmer of hope or it was like, we can do this a different way now.

other thing I think is that, and I still do this today is I. Every [00:16:00] night, hearing him beat her here. You know, 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 must've been self soothing, but it has, 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 to just put on you.

There's, I guess you have a choice, right? You take it or you don't, I didn't feel like I, I had a choice. I, you know, I was, 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 [00:17:00] 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.

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 I definitely didn't 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, I really do think that, so as an example and even part of why I asked that question was, I remember when 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, [00:18:00] 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 and 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 necessarily 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.

And I really do remember like that was something that was, on my mind for four years after that. And just this feeling of wanting, I think part of what you mentioned, which is this sense of control, I'm wanting to feel as though you can be in some ways the [00:19:00] master of your destiny and you can, you know, 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, I as I came to the UK as, as we grew up even the area that I grew up in, I was in, I was, 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 I and then this was the other thing that really touched me from what you were saying as well, because I, that was also when I started to read a lot of books and I don't know if it [00:20:00] 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 that 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 see examples [00:21:00] 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, 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. You know, I just, 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 [00:22:00] I now know that that was almost recreating the environment I thrive in. Right. It was like, I'm good at that but not good for me.

So when I, 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. Is it, it, you know, from everything, 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, that was like the first sort of things that were always in my head. I don't know that I was thinking of success [00:23:00] back then.

It was so survival focused that I didn't really, you know, kind of come into play. I feel like my twenties you know, I, I was married and I have two kids. Right. And and that was when I had my kids, I think was the time where I 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 does, like, what do I want out of this? Like, wait, what can I build? What do I want? And 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, you know, I mean, in LA it's hard to send your kids to public school.

It's, 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 [00:24:00] 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 thirties, mid thirties you know, they're film directors, they run ad agencies, which jobs I'd never heard of and I'm a software engineer, but, you know, but these times I'm still working. And I mean, I think in the early years, you're just, I don't remember a lot of people.

There 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 [00:25:00] 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 you know there was no control, but there was also no choice that was, you know, everything was forced on me.

I didn't, you know, and so freedom for time was what I went chasing. And I guess that's where I, that's how entrepreneurship started as I, I thought if I, if I chase this, I can, I can spend time with my kids whenever I want.

David Elikwu: I love that. And I think this kind of leads into that. That was part of the next thing that I wanted to ask, which is. [00:26:00] 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, 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

Christine Carillo: Yeah. You know it was a [00:27:00] terrifying leap to take because you're right. I had gone to a state stage where I didn't, I didn't know anybody who had been there from where I came from. And what happened was it the same? 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, I, they had a 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 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, I felt [00:28:00] suffocated there.

I, I mean, I show up to meetings. Sometimes and, you know, I wasn't required to be in the meeting, but maybe I had to go from LA to DC. You know, 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 [00:29:00] 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 was going to start a company, but what I did know was I couldn't be there anymore. And it was Christmas time. You know, we, 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, I, you know, 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. And him and I became friendly and he said to me. You're going to go out and you're going to be [00:30:00] 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 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, you know, it was kind of shitty actually to tell me this, but he said, you're virtually unemployable. I 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 [00:31:00] I, you know, then I, 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 actually a corporate job is not safer than paving my own path actually. They're determining my path there, I started to really think about, wait a minute, they're telling me how, like, whether I get a vacation or not this year, they're going to tell their, the salary they give me like determines my, 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. I, you know, [00:32:00] 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 I, you know, 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 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 they didn't, I already knew the insights of how insurance companies worked anyway. So I knew the rate would not even make them flinch and they [00:33:00] hired me and it was the first one. And I just kind of went, you know, took a leap and sort of went for it, you know? I don't know that it was confidence in myself more than that really wanting freedom, you know, is like 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, and you know, and I've got kids at home. So I was like, I've got to find another way. This is not gonna.

David Elikwu: Absolutely, 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 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, you know, serves their needs and serves the company's needs. And, and [00:34:00] 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.

And, and so, 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 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, was that, 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 into entrepreneurship and some people very quickly [00:35:00] 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. I, so the first company I built was everything I wanted. It was, you know, I, I sold that my job was sales. I nailed, you know, 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 [00:36:00] company I wanted to build. I had seen people, you know, at previous jobs where there was one woman who got cancer, and I 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.

So I 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 so my whole job was sales and it was also in a industry that I didn't love selling [00:37:00] to. I, you know, I love going into these

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. 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. You know.

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, you know, I was 39 with kids and a husband and everybody else, [00:38:00] 23, 24, you know I was in health insurance.

They were in VR and all the sexy, cool stuff. Right. So 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 me, that I was, I was the, I wasn't going to be your last bet. And that wasn't healthy because I grew that company at a explosive rate.

And I, 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, [00:39:00] 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 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. I not the way I was before I had these crazy migraines, I 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 [00:40:00] 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.

And, and I, you know, so 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. It was, you know,

I don't work well with you know, I guess being 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, I, you know, when I was starting. 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 [00:41:00] 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, think the thing is like, 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. I don't know if I answered your question or I went somewhere else, but I'll pause there.

David Elikwu: No, no, no, you did. Yeah. You know, you did it. And funnily enough, even that last part that you mentioned, it very much resonates. Cause I was just talking with some founder friends of mine recently, and we saw that there was a story about this, a company. I won't mention it, but you know, you you've probably seen them.

And I think [00:42:00] they had grown. They were big on social media wise and putting a lot of focus into growing the brand and trying to not so much get customers, but just trying to grow the image of the brand and their headcount had swelled to like 500 people. And, you know, they're getting loads of money thrown in from VCs and all of this.

And I mean, it's starting to crumble now, but apparently they only had like 600K in the bank. Like they were not actually making revenue because they didn't really have the customer base on the other side of it, but apparently investors don't always care about that. Investors primarily want a business that kind of looks and feels like it's growing and you're hiring all these people and you're doing all this stuff, but the real business fundamentals, aren't always there.

Christine Carillo: That's right. That's right. I think that's confusing. Like I, I wish there was, even though you'd think I'd go into Techstars and that's what they'd tell you, right? Like, Hey, like if you come [00:43:00] in here, this is, this is what it means to be VC backed. Right.

I wish there was, we talked about that more because I, you know, I I understand now their game, right. I, I was very fortunate to have a CEO coach. Whose name was Jerry Colonna from reboot. While I was running my last company Joni, and I remember one conversation we had, I was just seething from a board meeting.

I was like, these guys are so condescending, they're questioning my competence. And all of a sudden I'm being told, if I'm going to raise $50 million round, I need to look like a $50 million company.

And now I have to hire nine C levels. And I didn't want to, I didn't think I needed that. And on top of that, I had to grow the company from 40 to about 150, 160 people in a very short amount of time. And I, I, just, to me, it felt like such a waste, you know, to do that. Like, we didn't need that [00:44:00] and I pushed and you know, you're a founder.

And so there's these people I've done this for a long time. So there was a point in time where I just thought to myself, I don't maybe, I don't know. Maybe, maybe they're right. Maybe I'm I'm, you know, I'm in there chuckling when they're saying this in the meeting with me, like I'm so such an idiot that I don't know this, so maybe they're right.

I'm talking to my coach about this and he says, which was so good to have someone like that because he sort of make sure I don't feel crazy. Right? Like, he'll call you out when you're you're being, this is not okay. And then another times where he's like, Nope, you're right. You're, you know, you've, uh, assessed it correctly.

And he had said to me said, you know, the problem you have is you don't think like a VC.

I thought what he said, if you don't, you think like a founder, which is okay when you don't have VC money, but you have a lot of VC money and you're about to raise $50 million, you have to learn to think like a VC. [00:45:00] It was the first time I'd really thought about that.

You know? And it's like, I've never even really understood the VC game, and now you're telling me, I have to think like a VC. And so I did, I spent the next six months really putting myself in their shoes and understanding at the end that this was in a, they're a marketing machine and they have to be to be able to get these great deals for their LPs and you know, and so yeah, of course the grow at all costs and all of this is, you know.

They have many companies, we only have one, so our, our life is in this one or we think it is anyway for many of us. And so it's hard to pull back to think. So maybe don't feel pressured when they're saying all this crazy stuff, you know what I mean? Because they're, they're not they're not really paying attention to you, but they're really caught up and excited that everyone's excited about you. So then they're going to keep pushing you to go, go, [00:46:00] go, go, you know?

And yeah, it's a shame, you know, I, I think the part that's a shame is that because they're a marketing machine and the lot, the media really publicizes all the big rounds, all the big, all of that. The other side of it is the bootstrap founders or not bootstrap, like hybrid. Like what I did, which was, you know, a little bit of both without VCs, we don't have the, the money maybe, or the time to go out and publicize our stories.

Right. So, so nobody really knows about those. And as founders you come in and you think there's only one path, otherwise there's nothing else, which is what you said it, you know, I talked to my friends who were like, oh, I was amazed this one friend of mine, she runs an e-commerce business. She makes about 15 million a year, USC business grad school.

And she was like, it's so crazy how you run your company. I take 80% of my [00:47:00] revenue as my income, and I was like, oh my God, what am I doing? I'm killing myself over here. And like, she's like, but we make income. I mean, we have revenue, you know what I mean? And it's super slim and it doesn't cost a lot. I was like, how, because you're right.

The VC world doesn't really always play in the same game as the rest of the business world. And we forget it's a tiny part of the business world. Really, it's not, the rest of the world is running great businesses. People are happy, you know.

David Elikwu: Yeah. People forget that you could have a profitable business because so many, I mean, even when you look at some of the biggest startups, now, most of them don't make money. And the expectation is maybe for the first five years, 10 years, you're not even going to make any money. And it's just about how long you can keep the game going. Until one day you maybe become profitable.

And so you have a lot of companies that actually the real struggle is growing into the valuation. That's been set, like you've already taken on the money. You've already got this valuation. That is, [00:48:00] whoa. Your company is valued at so much, but now it's going to take you another five to 10 years to actually become the company that you are supposed to be.

Christine Carillo: Exactly. Exactly. And, and and they know because it's their game, right? There's no fault to it. It's their game. It's just, we don't know. We don't look into it enough before we sign up, we get caught up and we might be, you know, one of the extraordinary exceptions that makes it, one of the things that I tell founders, a lot of the CEOs that I coach is it's a lot of pressure to have to be extraordinary.

You know, I'm, I'm definitely not extraordinary. I'm ordinary. And so I don't want to even pretend to be extraordinary because there's so much to live up to. And, and, and to have to think you have to do when, if you're just ordinary, I can maybe do extraordinary things, very different, you know, from time to time.

But I don't have to [00:49:00] always fucking be extraordinary, you know? Like it's like way too much. And sometimes when you take that path, that's, what's expected of you, you know, there's other world, you can just, you know, you can run a great business, do extraordinary things when as often as you'd like, or not, it's up to you, however you want to do it and still grow a wildly successful business.

David Elikwu: and I think that's kind of where you are now, where now you are maybe trying to build a bit slower and a bit more intentionally and thinking very much about the life that you're trying to build as well. And funnily enough, this also ties to another, you know, I think there's always. So I did a uh, some entrepreneurship program thing, not too long ago.

And right at the beginning, they making this distinction between, are you trying to run a lifestyle business or you're trying to run a proper business.

And the emphasis being that running a proper business and being a proper entrepreneur is very much about going in this direction of, of [00:50:00] scaling up and scaling rapidly.

And if you're just trying to run a lifestyle business, that is just, you know, like the poor man's, you're like a dentist or something, but I, I don't think it's necessarily that way. And I know that maybe there's different scales of lifestyle businesses, and it's not necessarily that you're just running a small, like a tiny SaaS company.

But also, I mean, there's no shame in that. And you have people that run slow businesses or businesses with small teams that make millions a year. And actually very much like what you were saying. There were people that run smaller businesses that make decent amounts, but they take the amount that they take home is a much bigger chunk of that pie than the founder of a 100 million valued business that just gets like a much smaller amount

Christine Carillo: That's absolutely right.

David Elikwu: Yeah. So, one question I wanted to ask is maybe digging more into this philosophy around the 20 hour CEO and what that looks [00:51:00] like for you and how you go about quite intentionally building a small team. Also, particularly, as an aside, I know that you talk about your team being distributed um, like completely remote and not necessarily all being in the same location.

So I'd love to know maybe a bit more about that as well.

Christine Carillo: Yes. I guess what ended up happening was I am. When I built Butler, which is the mental health company. I, because I didn't have anyone to show anything to or prove to. Right. I, I, I didn't have to hire also what they, what they wanted me to hire. And now I was like, you know what, I don't, I don't, there's so much talent around the world.

I like giving other people opportunities too, that maybe could never work in a company like this. Right. And I personally like to work with a lot of different cultures. I grew up in LA and that's just, I'm very, it's very natural for me and comfortable.

So anyway, I built my entire team distributed from all around the world. [00:52:00] And I started to mess around with. I guess the thing was, I was doing so little because I had automated so much or we had these good systems and we just kind of started out with it, like, okay, here's, here's how we work. Here's how we communicate.

And every end of the week I look at what went well, what didn't go, well, what do I automate? What do I cut? What do I delegate? All the normal things. And then, but the difference was I was pushing my team to think the same way. So these, when you have people who join you, who haven't worked for a company where you're only required to work from clock. It's a big culture change for them. Right? And then on top of that, I'm asking them to make decisions and run things without me. Cause I'm not working very much anymore. Right. And asking them to figure out ways so that they could be done in two hours. And go off and go do whatever they want to do.[00:53:00]

That was a different challenge for them. But once we establish that together, anyone else who came in, you know, we remember we hired an engineer and the engineer starts sending emails at like 2:00 AM and then on the weekends.

And it was so awesome to see other team members. It didn't have to be me and we're a tiny team, but they're like, Hey, we don't do that here. Here's where you go look at notion at how we work. But, you know, we don't, we don't do that. You should go spend time with your family or go to sleep. Like, you know, like this is not what we do.

And so we, it just became ingrained that that's how we work. And it's not really as much of a magic pill as people think it is. It's, it's, it's honestly deciding, being intentional about how you want to work and how you want to communicate and making that easy for people. And figuring out just from all of our perspectives. Like I remember I was helping this person hire an EA and he said, well, I don't know though that I would need her full time. And I was like, [00:54:00] why do you care? Like, if you've got someone who's loyal, good, smart. Why care if she's working two hours or eight hours? Like who cares? You know? And he kind of thought about it.

Cause yeah, I don't know. I guess we think we have to get the most out of people like, well, do you want to get the most out of that is getting the most out of her. Like, that's pretty much it. She's not going to be able to do, you know, 20 hours in a day. That's actually getting the worst out of someone, you know, when you push them that hard.

So I guess we, we started that whole intentionality of how we want it to work and and created that. And then over time I started to see. If I could work four hours, well, five hours a day, four days a week. And then after I did it, and my team was well aware that I was working four days a week, I asked them how they would feel if we went to four days a week and the, the way we did it was okay.

So we would work four days a week. We wouldn't change our hours. Like the number of hours we work in [00:55:00] a day. I really don't know how long people work. I think they worked between like five, maybe seven hours a day because people just aren't, there's not that much for us to do. Like we're really managing systems more than anything else. And, and they, everybody was excited about it. And I was like, the only caveat is we have to continue to reach our outcomes. So let's experiment. See if it works, if it works great, but I really don't think that anyone can even be focused for more than five hours a day. Anyway. So, you know, anything after that is sort of gravy, I guess, or waste, however you look at it.

So then that worked and and you know, things kind of got better. Actually, people were more energized coming in. You have more time off all those good things happen and it made us even more ruthless about looking at our business.

So then, so it's nice. It's nice to have a team that I call lazy in a good way though.

I mean, they're like, no, [00:56:00] I'm not, I'm not going to do this three times. You know we're going to automate this or they also take that into account. So it's not just me driving it. And I think, I think sometimes we're founders miss this in this 20, hours CEO is one is I think we've been programmed to think that hard work, long hours equals success.

Not, I'm not negating that in the beginning of anything you do, you have to put in a lot of effort and energy. But that effort and energy may not always be equivalent to time. And it may not always be hard work. It depends on how you look at it, you know? And then, so there's that programming that needs to change.

But if you can't really believe that there's not a lot, I can teach you because similar to what I had shared earlier, where I could teach someone, all my frameworks and all the ways I automate and systems and how to get an EA. But if you're still going to fill up your time, back up the way I did it doesn't matter.

You've just, you know, [00:57:00] like the real question, I think at the end of the day, for anybody, not just a CEO, but also an employee, but especially I think for founders and CEOs is how do you want to spend your minutes? Because if you're just spending them. And wasting your energy in the name or the art of taking on more.

You're not going to push your company any further it's it will plateau, you know, and most companies fail because of the founder running out of energy. Not really because of anything else. It's, it's that energy that depletes that allows them to miss the opportunities. They don't have the drive anymore, or they can't figure out solutions, they're tired.

If you're tired, you can't think of new ways. So I do spend a lot of my time playing, reading you know, outside a lot with friends with, I mean, I don't work very much. But I guess [00:58:00] when I work. It's very deliberate and focused. And I, I can do a lot more in my small amount of time because I'm ready. I'm energized. I'm very, very focused to do it, you know, and the company's run without me, which is the goal cause otherwise you know, we forget we're human, so you don't want your company to be dependent on you. You want it to be dependent on the systems and be able to have that company function without you as if it was a franchise almost like it should just be repeatable.

David Elikwu: How do you get the culture, right? Particularly when I think it's, there's layers of things here.

So one, particularly from what you're describing, it's, you know, you're running high on trust. you're running high on autonomy, you're having less hours and lots of companies are having to deal with this now to some extent with the pandemic and everything, where people are suddenly having to realize that you're going to have to trust people, they're going to be working at home.

You can't be monitoring them in an office and looking over [00:59:00] their shoulder and making sure that they're working. But I think also redefining how much work is enough and what does good look like? Because just like you were talking about with your friends scenario, I think there's this expectation that, oh, if I'm hiring someone, I need enough work for them to do. I need to be filling their days every single day. And if I can't then, you know, is it worth it and finding the balance between getting your own schedule right. And maximizing your time. So I think it's a two-part question. You know, you are trying to prioritize your time and do that effectively so that you can focus on like the bigger pieces and you can focus on leading, but how do you get, how do you build in a culture of, with that trust and autonomy and where people feel confident being able to make decisions and also knowing when to start and when to stop knowing you know, that they can do enough and know what good looks like in a given day or in a given week?

Christine Carillo: [01:00:00] Yeah. I think you know the biggest thing is that I spent a lot of time in the beginning thinking through our systems. And so when I do that, I'm also sharing with my team. So you can imagine in the beginning, I'll give you an example. So when I first started Butler, I had to go figure out sales. So it was like, I don't even know what we're building.

We don't know yet. We don't know what therapists think. Like, not like, you know, so I went out and talked to therapists for two weeks and there's a process in that like day one, you don't know what you're doing. Right. But by day three, there's a little bit of a process. Now that little thing is just a system.

That's it? It's a, step-by-step it doesn't have to be fancy, but now I'm like, okay, now I know how to do this. Where we're, you know, we go to this website, we find them in our area. We send them an email. The first day we sent them an email saying, hi, we'd like to chat that failed. [01:01:00] Second day, we figured out, we sent out an email saying, we want to interview you. That works. Can we buy you a coffee that you're just tweaking this little system by day three? We know how to, okay, so now I'm no longer driving to them. Let's have them meet me at the coffee shop. So now we tweak the system again, just a tiny bit more. So all this is just to say, I guess, as we progressed, you know, during any of this, I'm just kind of writing it down and notion like there's nothing fancy, but I'm like, okay.

I changed that step two to this now. And everyone sees it. Right? And so, as that gets built out, because the team sees me do it, they do it as well. And I asked that in the beginning, when someone new is coming on,

They don't know they're supposed to do that. They might read about it, but they don't really know it until you push them.

So part of that is being like, Hey, that's great, but I don't see a document of that notion. Could you make sure you do that? Because we document everything in there. Can you just make sure [01:02:00] that if we change the system, you've, you know, you've put that in there. So that's the first part. The second thing I think is people need to know how to make decisions in our company.

Like how do we make them? What is it that matters to us? Do we make them quick? Do we make them slow? Which ones have a higher severity where you make with someone that you have to check in with me, which don't you have to check it. Like that's important too. Right? So a decision making framework is super important.

And then I think the third thing is having a talk about systems a lot, because I think that is. Really, what is usually missing in any company is just being, and I don't think you have to systematize every single thing, but anything you do more than once or twice, you definitely should. And so the other thing is an operational framework.

So basically a simple way in [01:03:00] one platform or as few as you can get where everybody's working out of that. And so for us, for example, we don't use email for internal communication. I've never found that to be helpful, frankly, I hate managing people. It is like, so I don't hire anyone I have to manage either.

I've never been able to work with people. I can't that I have to manage. And so I don't want to also treat someone like a child. Like I don't want to come out and say, Hey, where are we with this? And that feel so embarrassing to me. Like, I should know where something is. I should know where our sales are. I should know what's going on with that latest account.

I should already know what's happening with whatever we're working on in product. But so then I had to think to myself, how will I know that without asking someone? And so for us, it's like, all of our work is done in one place and we have to update our own [01:04:00] work in that place, which is notion. So there's this operational framework of anything to do with work projects.

Anything, all discussions are here in this particular platform, notion slack is used as if you were in the, you know, at work. So if you want to chat about whatever you can, but as soon as you start talking about. Like don't ask me about a project in slack, because you're going to have to repeat it in notion because that's the place where I got to go look for it, you know, specifically to that.

So email is not used internally, which then leaves us with notion and slack. And the other thing we do in slack is one-on-one so for example, if someone's asking me something about an engineer, about a question on a project they won't ask me directly. They'll just put it in the team chat because everyone should know about it, but if it's something sensitive than they would, you know, ask us about that.

And then, so that you've got this operational framework where people aren't looking for [01:05:00] information everywhere. It's not scattered, it's all in one place. The reporting is done automatically in there. So basically every week there's a memo I send out, but I, I only spent 15 minutes on it because it just pulls in data from notion already.

And so we all see the same report. Oh, here's where engineering is. Here's where marketing is whatever. And I might add in some new insights from maybe data I've looked at or something I see within the company. But in that memo is our mission, our values, our outcomes, like what are we trying to get to?

Why does that matter? How are we getting there? What are the bets we're making? And if they don't know those things, they don't know when to stop.

So that's, they don't know when to stop working. They don't know when we've gotten there. They don't know, you know, cause it's also ambiguous. Like when people say, oh, we're trying to be the biggest take the, all of the [01:06:00] market share in.

Whatever healthcare. Well, what does that actually mean tangibly though, you know, oh, we're trying to triple our revenue this year, but can you, is that really something you can do realistically? Or are you just like, you know, putting some big number because people think they have to make people work really hard, you know? It's like, but if you just say like, if we can get to this and this happens, people are going to try to get to that. I mean, people aren't trying to be bad at their jobs. I got to tell you, I mean, that's very rare. They usually suck at their jobs when their managers and their bosses suck and the environment sucks.

I mean, then I always think you've got to look at yourself before you look at what they're doing. If they're not motivated, there's some reason that goal is not aligning what they want. What you want, are you underpaying them? Are they feeling, you know, not respected? That's I wouldn't go to work if I don't feel respected.

I mean, there's a lot of reasons, right? To think about things you don't feel good at your job. Big reason not to continue to be good at it. So [01:07:00] I guess that's a little bit about how I, I pushed the culture. I'm very vocal about this. And I, I guess I give accolades more when people work efficiently, reach outcomes than how hard they work.

So, you know, in the beginning I have usually people try to prove how hard they can work. Cause that's just in our DNA. And I just don't give that much of any kind of a glimpse, but I'm always very supportive of ask me questions, ask each other questions, the dialogue, the discussion, the, you know, I figured out a way that we don't have to do XYZ.

You know, all that stuff. The last thing is when you think about, for me, I like working with peers. And like I said, I don't want to manage them. So I don't, I don't monitor who's online and who isn't online. Everyone makes their own hours and works when they work.

We just have to reach our outcomes. I have had people who don't reach the outcomes and they're always [01:08:00] very clear and then they can't work with us. Right. Cause it's like a different job they have to have, or maybe we're not a right. A good fit for them, usually in some capacity. And that's okay. But I think you know, asking for time off is weird for me. So I don't like that either. I just feel like it, it it's humiliating. So we just, I all that stuff. I removed me having to have anything to do with it. So everyone's on the salary. I don't care how long they work. Right. When people take time off, we have a slack bot that we built that basically you reply to it and you tell it like, oh, I'm going to a wedding in two weeks or whatever, or I'm sick today.

And instead of emailing me it emails or notifies your teammates and you pick who needs to know. And so if you're working on a project with someone and it just sends them a message that, Hey, so-and-so is out today or they're going to be on vacation, whatever. You know, I don't, I don't think it's that hard to do. I think [01:09:00] just, we have a weird way of looking at work where we really think we have to get every ounce out of people. And you could really have people will stay with you when they're happy and feel valued. You know, they, I don't know.

I would work my butt off for someone who made me feel like I was important.

David Elikwu: so much of what you said resonates with me. And I think so, you know, I have my business and I try and run it the same way. It's probably a bit smaller than yours. I only have one full-time employee at the moment. Although, uh, previously I think, this is why I was asking the question about culture.

Cause I've had of people at different times. So at one point, I think I had, you know, one person, well, cause I still also work full-time a startup, so I'm running the business on the side and I have full-time people for me. So I had that work person full-time one person, like half time. So part-time and then one intern. And I don't know, funnily enough, going from that to only having one person full-time and then one intern, rather than having. [01:10:00] Like too many people has actually been better. And there was an extent to which an amount of work that Yeah. it's two things. One is just consolidating some of the process within one person, one person that actually can see things from end to end and actually knows what to do and is able to handle it.

And also just. Kind of goes back to what we were talking about earlier in terms of headcount. Sometimes it just feels better to feel like you're growing into to feel like, oh, let's hire another person and let's do more of this. Let's do more of that. And it might not actually add incremental value even though, you know, the people might be great and you might love working with them.

And all of those things can be true, but I think. It's a balance of what we call productivity. It's not about squeezing every ounce out of people, but it is about doing your best work in, in the best way possible. And I think that's another thing that I've, you know, had some, had a journey where the, in terms of trying to find the balance of is going back to the culture thing is [01:11:00] it's so interesting working full-time while building something on the side, because

I can see, I know the kind of person that I am, and I know that I don't really, I don't want to be micromanaged. And so I don't want to micromanage anyone and I don't want to have to check what you're doing on it. So I very much lean towards 100% autonomy. We have a very similar uh, tech stack to what you just we work in notion, slack, and then I just send loom videos if I'm doing something and then I want you to do it. I'm just going to record myself doing it once. And then here's the video. And I think what works well with that is one, you see me doing it and you know, what the process is, but then also I'm explaining some of my thoughts and some of the other things I'm thinking about and the decisions I'm making while I'm doing that thing.

So, Yeah. If some of those conditions change, then you know that maybe the action should be different from what I've just shown you. But I've also noticed that not everyone is comfortable working like that. And so this goes to what you were saying about, you know, sometimes it's not the right fit because.

Some people do not respond [01:12:00] very well to complete autonomy and freedom. And me not checking up on you and seeing what you're doing, because, you know, I am almost treating people like how I would want to be treated. And I'm like, you know, I don't care if you take time off. That's fine. Just, I mean, yeah. Let me know, because we don't have teammates in the same way that you do.

So it's good to know. Okay. If someone is not doing anything today or tomorrow, or something's happened to you, it's good to know that. I don't care. I just care about things getting done. But I do think that there are some people that want actually more, I don't want to say coddling, but they want more supervision.

And so it's interesting thinking about hiring a right in the first place and making sure that you do pick people that match that culture and match that expectation and are willing to step up and be autonomous. And, you know, they actually want to take control over their, their time and their schedule.

Christine Carillo: [01:13:00] Yeah. You know, I've also seen, I think you're right. I mean it's, it's the, the problem is that working like this is so rare. And so I mean, you're not even treated this way in school, so very little of your life. Do you have the opportunity to work with peers as true partners and it's, and, and because during, you know, how most of us went to school, it was about being told whether we were good at something or not.

And. And getting repeated feedback on that, you know, was, was that good or not? You know, you didn't in school, you rarely do something in class. That's just because you wanted to it's, you you're told what to do and you do it right. And that those are the assignments. And so, so by the time someone starts working, they go into these normal [01:14:00] companies that, you know, have just been doing things the same old way.

So on top of that, there's cultural differences, right? So for example you know, my engineers, I love hiring engineers in India. I just adore that culture. And in particular for engineering, they are so smart and and very thoughtful of how they, they look at problems to solve and have so much ownership over the work they do.

But in India,

The hardest thing for someone who comes to me is that they don't just know the one little itty bitty thing they're working on, but they know the whole thing. They know, they know everything and that's can be overwhelming.

They're, you know, they're usually not used to, usually a lot of the work is checking in, is this okay? Can you review it before I can do something with it? So it's like fun learning that they [01:15:00] only talk that nobody would ever dream of calling someone out publicly. It's not how they work. It's not in there, you know, so it's not calling out, but like teaching them to even be able to, I want you to talk about the project.

Broadly, not just with one person. So everyone knows that that's a big deal for them. Right. And then they second guess themselves in the beginning because they, they, a lot of times engineers, especially before you become a, you know, not a senior, but even like a manager you can't make decisions.

It's just not your job ever. Even if you think you see something that could be done better, can't really voice it. So, as an example, my lead engineer who's a female on top of it. So really hasn't had a lot of these opportunities. Right. But we were working on this project and was something very simple.

I remember, but it was early on when she just came with us and we were trying to get the therapists images to come up, like to save them. Right. [01:16:00] So upload your picture and then we'll show it on the profile. When you match with someone, not a big deal, very easy to do.

But I was very surprised because she sent me a message and said okay, Christina, I'm working on this. How do you want, how should we do this? Like, where should we store them? And I was like, what? I was a bit taken aback, you know? It's like, well, that's, that's odd that she would ask that, you know? And I said, well, how do you think we should do it? I wish I know how to do it. And I could've just said, oh, will you put it in AWS buckets? Which is where you would store the images. But if I would've done that, I would have missed an opportunity to encourage her and remind her that she has the answers. She just has never been exposed to this type of working relationship. And so we went back and forth a bit, you know, like she got nervous.

What if she gets it wrong? What if she has the wrong answer? And remember, I have a [01:17:00] crazy title that makes everything about talking with me different. I'm the CEO no matter what I can't remove that fucking title. And so people are immediately intimidated by that. They might second guess themselves just because of my stupid title.

Right. So I have to be very aware of that. And so I'm trying to really make sure people feel not, it's not like you should feel so comfortable with me that you can feel anything like that's kind of bullshit. It's I want you to remember to tap into you because that's why I hired you because you were so smart and you know what to do, and you really don't need me.

You know, all I have to do is keep money in the bank. Everything else you don't need me. I'm just an employee here. I don't really know that much. And I think when I talk to them with that and keep encouraging and reminding them, that's the bit, I think that makes someone start to really grow. And the problem with that though, is [01:18:00] what I shared before.

Once you see it, you can't unsee it. So once you see working in that way, it's hard to unsee it and go work somewhere else. And so I, I get what you're saying. There's, there's people who don't know most people don't know how to do this, you know, this way, because they've never had the opportunity. So you get a chance to decide if you want, if there's someone that you can help them, you know, get comfortable with this.

You know, I have someone that came to work for me that was like, I am, I get anxious quickly. And I need to know that I'm doing well at my job. It's like, okay, got it noted. I don't have time to manage you, but I certainly can make time to remind you when you're doing well. So not a big deal. Right. So I, I note those things.

And if that's what you need until you start to feel that inside of you, it's not going to take that much of me to do [01:19:00] that. You know? I invest a lot in people. I want to do that and, you know, even if they leave, I don't think that's a bad thing. I think I still want the biggest joy is investing in people or the small things you do.

Like, you know, I don't know, you always have these revenue goals and they always get bigger. It's all bullshit. Do you know what I mean? At the end of the day, it's really where we spend our time and with who, you know, I, I make a good living. It's great. I'm fortunate. I get freedom to work on what I want to work on, but I also feel that's the same with people who work for me, they can work anywhere.

So how do I make it so that they can also have at least a sense of freedom to where this feels like they intentionally want to be here? Not they have to, and even if you have to, and you don't really want to be here. Can I make it. So you feel like a respected adult that feels valued because you're putting that in, you know, and so how can I meet you halfway [01:20:00] there?

If it really doesn't work, it doesn't work, but I love investing in people and figuring out ways that as a community together, we can live a life of good work that fills us up with good people that fill us up. But knowing that this is not our take priority over our life, we have a whole other life we're all trying to live and stay above water on.

You know what I mean? Work is I love it when I love it. But then there's times where I can't do it, which is why, you know, I have to reduce how much I work. You know, if my, my son was recently ill and I felt so lucky that I took four months off. Like, I just, I, you know, nothing suffered other than the clients I coach.

I couldn't coach clients and I wanted to just be with him and help him through what he was going through. My businesses ran without me. I didn't have to do anything there, but the coaching had to stop, but who cares? I, I'm not going to get another opportunity to be there for my son. That's [01:21:00] like, that's it right there.

Nothing else really matters in the end. Right. So, but I think that's the same for anyone who works for us. I want to make sure that they're doing what they need to do with their parents, their siblings, their friends, their part, whatever it is, you know, otherwise it's just kind of no point to this whole game, you know sort of lose the plot.

David Elikwu: Thank you so much for tuning in. Please do stay tuned for more. Don't forget to rate, review and subscribe. It really helps the podcast and follow me on Twitter feel free to shoot me any thoughts. See you next time.

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