the bossbabe podcast - 436: I Exited My Company for $250M, Here’s The Mistakes I Won’t Repeat Again with Ankur Nagpal

Episode Date: November 21, 2024

Ever wondered what it’s really like to build a business in your twenties, ride the rollercoaster of entrepreneurship, and come out the other side? In this episode, Natalie sits down with Teachable founder Ankur Nagpal to spill all the tea on the evolution of online education and the booming creator economy. Together, they take a trip down memory lane, sharing the highs and lows of startup life (spoiler: it’s not always pretty). Ankur also dives into the juicy details of navigating market saturation, using AI to shake up course creation, what happens to your identity after a big business exit, and how he really spends his money after the $250M buy out. If you’re obsessed with entrepreneurship, creating impact, or staying ahead of the trends in online learning, this episode is packed with value— plus, you’ll learn what his second venture is, why he couldn’t just “live the travel life” + what he’s doing differently in business this time around.  TIMESTAMPS 00:00 The Journey Begins: From Teachable to New Ventures 03:13 The Evolution of Online Courses and the Creator Economy 05:51 Navigating Identity and Growth in Entrepreneurship 08:53 The Decision to Sell: Reflections on Success and Freedom 11:49 Financial Freedom: The Shift After Selling Teachable 14:53 Building Again: Lessons from the First Venture 17:58 Hiring and Team Dynamics: The Balancing Act 21:00 The Challenges of Industry and Team Management 24:03 Personal Finance for Business Owners: Key Insights 27:09 The Importance of Mindset in Business Ownership 30:12 Maximizing Financial Benefits: Tax Strategies for Entrepreneurs 32:53 The Psychology of Spending: Balancing Wealth and Humility 35:54 The Impact of Upbringing on Mindset 39:08 Understanding Financial Management for Business Owners 43:47 The Importance of Recurring Revenue 46:53 Navigating the Challenges of Building a Fintech Company 49:57 Marketing Strategies and Audience Engagement 52:17 Getting Started with Financial Tools 54:37 Balancing Personal Life and Work 01:06:04 Redefining Success Beyond Money RESOURCES + LINKS Use this link to grab your special offer from Ankur on carry.com  Black Friday at Bossbabe is coming! Join the Waitlist Here to be the First to Know What Our Secret Offer is.  Learn Natalie’s Proven Method for Building a Profitable, Predictable, Freedom-Based Business and Get Back to WHY you Became an Entrepreneur in this FREE 90-Minute Training. Join The Société: Our Exclusive Membership Where You Can Access All of Natalie’s Keynotes & Unlock The Best Systems + Tools To Help You Build A Freedom-Based Business. Get Our Weekly Newsletter & Get Insights From Natalie Every Single Week On All Things Strategy, Motherhood, Business Growth + More.  Drop Us A Review On The Podcast + Send Us A Screenshot & We’ll Send You Natalie’s 7-Figure Operating System Completely FREE (value $1,997)  FOLLOW bossbabe: @bossbabe.inc Natalie Ellis: @iamnatalie Ankur Nagpal: @ankurna

Welcome back to the Boss Babe podcast. So today we have Ankur Nagpal on the podcast and this was a really interesting conversation. So I'm going to give you a little bit of context on who he is and then talk about some of the things you need to listen out for in this episode. So Ankur previously founded Teachable, which is a platform that enables creators to monetize their expertise. It was actually where I had my first ever course. And I remember getting invited to meet him when I lived in New York at the time.

This was maybe nine, 10 years ago because I was a creator on the platform. So he scaled Teachable to 60 million in annual recurring revenue, one billion in creator earnings, and he exited for a quarter of a billion dollars at 31 and he owned approximately half of the company. Now he's the founder of Carry, Carry.com, which is a platform to help business owners grow their net worth by saving money on taxes. I want to be super transparent. I'm actually an investor in Carrie and I really believe in what they're doing as a company. I've been an investor for over a year now, I think it is.

And I really, really love what they're doing. This episode was so interesting in so many ways because Anger is not the kind of person that exited for quarter of a billion dollars and then went and lived this flashy lifestyle. In fact, he'll share, he does not do the private jet thing. He is so low key and he's already back into building his next startup at the age of 35. And the way that he thinks about money, the way he thinks about growing businesses, freedom, all of it was really inspiring. And I got to dive into a lot of the lessons that he is not going

to repeat the second time round. And I think being able to get that hindsight from other business owners is so invaluable. I know you're absolutely going to love this one. So let's jump in. So let's jump in. So let's jump in. Welcome to the podcast. Welcome to the podcast. Thanks for having me, excited to be here. Thanks for having me, excited to be here.

So we met how long ago? So we met how long ago? Somewhere between eight and 10 years. Somewhere between eight and 10 years. I remember being on Teachable, like when I first started doing courses, it was way before BossWave 2, it was an Instagram course.

So just this whole full circle moment, I love it. I don't remember the year, but I think it was at our office. I think it was at our office. I remember being on Teachable, like when I first started doing courses, it was way before BossWave 2,

it was an Instagram course. So just this whole full circle moment, I love it. I don't remember the year, but I think it was way before BossWave 2, it was an Instagram course. So just this whole full circle moment. I love it. I don't remember the year, but I think it was at our office in Williamsburg. It was. We used to have parties for our creators and our team and yeah, I think that's where we met. Yeah, I love it. So again, I don't want to go too much into Teachable Story because people can go and find that everywhere, but let's just give a little TLDR. How long were you building that company? Real quick TLDR about my entire life. I'm Indian kid grew up in Oman in the Middle East, moved to America for college

because like any Indian kid, I thought I wanted to be a software engineer. Didn't last very long and turned one summer at Amazon. But in college, I started a business creating Facebook applications, scale that to the point where I was making money on the internet. And you know the feeling, once you make money on the internet, it's very hard to do anything else. Fast forward a couple of years, moved to New York, started Teachable when I was 23 years old. Ended up selling the company when I had just turned 31.

And yeah, now here I am running a whole new company. Starting a company like that when you're 23, I mean, did you know what you would do? I mean, I know the answer is no, but like, did you go into it, you're super naive? I do now, looking back, I think there's an advantage of knowing nothing because you also don't know what you don't know.

I think at 23, 24, you have a lot less to lose. Like I have friends who are trying to start a company in their mid-30s, maybe they have a family. It feels so much higher stakes to like give up a salary to take this big risk. 23, 24, you're not thinking about that. You're just kind of doing. But no, I had no idea. And you know, I think that actually worked out.

I'm sure I've seen this in another interview. You actually had looked at Shopify and you're like, wait, I could just do this for another industry. Is that right? Is that where the idea came from? The first version of the idea came because we had our own courses. We had put it on a platform called Udemy, which people may know. It's a marketplace where you put courses. So the idea came from there where we had these courses on Udemy,

but saw that they were taking 50% of every sale. We didn't even get email addresses. We couldn't cross-sell or upsell or do anything. So the first version was meant for Udemy creators. And it was probably year two that we looked at Shopify, which is always a really amazing business. Then we changed our pitch. We're like, Hey, we're like Shopify. We started with where Udemy, but on your own website. And then we changed it to our like Shopify for education. So you already had a good understanding of the course industry. No idea. We knew nothing. We knew nothing. We had a couple of courses. The creator economy was not

a thing at the time. We were looking at WordPress plugins as our competition. We didn't really know much at all. It was only as we got deeper, we learned about the information product space and all of that. And all the things you've learned now, I'm really curious. Do you think the course world is saturated? Do you think we're still at the beginning? How do you think about the creator economy through the information world? I think the creator economy is here to stay. I do think courses now locally are struggling a little bit.

And I think there's a couple of reasons. I think one in 2020, everything jumped online. And it took a while for like the rest of the world to catch up. How much like teachable, for instance, we doubled from 25 million in revenue a year to 50 million in revenue a year in three months. That's a lot of growth to pull forward. The other reason I think courses are having a hard time

is think about the younger creators now. There's so many creators that, I feel too old, I'm 35, but there's creators that are 21, 22, 23 years old, even younger. They have tens of millions of followers, they don't do courses. Courses are considered kind of like not cool. So the younger generation of creators, they're monetizing in other ways. And as a result, if you look at the big course creators, they all tend to be a generation older at least. They're all at the youngest, like late 20s, but typically 30s, 40s, and so forth. So as a result, I

think courses have lost out with the newest wave of creators, and that's hurting if you look at the overall numbers. Do you think five, 10 years from now, courses will still be as big as they are? How do you see that changing? I think there will never be a shortage of people monetizing knowledge.

We always told people not to focus on courses. What you're really doing is you're helping someone reach an outcome. Courses is a form factor, may evolve, may die or whatever, but there'll always be a world to help someone achieve that transformation, that step. What form it will take, it's hard to tell with like AI and VR and all of that, but there will never be a shortage of like me coming to you, paying you money to help me achieve my goal. That will always, always be there.

I agree. And I'm so curious with AI how all of this will change because I mean, some people are very honest about, I create this whole course on ChatGBT. I think that's gonna be really interesting to say. I don't think any of us know how that's gonna play out. The hardest challenge with AI is like, it's become so easy to create a large quantity of pretty average content.

As a result, you have to think like the really good stuff will shine, but you have to wade through a lot of shit to get there. I know, but the thing is, it's getting better and better and better. Like we have been uploading all of our content, and now we can put together PDFs. I mean, in seconds. It's crazy. It's really good for like refactoring existing ideas.

I think it's awesome. I also think there are some very specific cases that are genius. Like we were just talking about getting a visa. One of the things you have to do to prove that you can get an extraordinary ability visa is be a published author. I heard of someone who basically used AI to write a book

and they went from a published author in like 15 minutes and no one in the immigration office is actually reading the book. So there are some cases where you have to produce a large quantity of okay content, it's genius. Wait, that is absolutely genius. Incredible. I feel like that person would be an amazing entrepreneur.

And as a result, like I think America's lucky to have them. Can you remember, was there a specific industry or content type on Teachable that just crushed compared to the others? The courses that made the most typically helped you earn more money in some way, shape or form. And the reason for that is they could charge more per course sold. Like for instance, we had a very successful course on how to play the handpan, which is an instrument I never heard of. They sold a lot, but because it's playing an instrument, their price point is $20, $30, $40. But a lot of the courses that helped you make money

could charge 300, 400, $500. So as a result, those did better. But the thing I will say that made me feel good and kind of surprised me is it wasn't just like make money online type stuff. There was tremendous diversity in the kinds of courses that people taught. One of our most successful courses was how to have a water birth.

And all kinds of topics. That must have been so interesting to just say, wow, I didn't know it was a niche year. It was fascinating. Where it got tricky is eventually we reached a point where people tried posting content that we thought was kind of inappropriate, but then it became our job to decide what was or wasn't inappropriate. And the amount of hours we lost at a company deciding like, should we draw the line? Like what is past the line? Like some things clearly past the line, some things not past the line.

And yeah. I was just at the Kajabi conference over the weekend and they were telling me that was one of their biggest issues. I guess content moderation, if you're in that business is such a thing. We had one course that's like clearly hate speech. Some race talking about why their race is superior, easy. Then we had a course on overcoming white supremacy, which I fought to keep where people are paying money

so they have white supremacist feelings, but they're paying $200 to get over those feelings, right? So this is fascinating. What? As a company, I was like, we should encourage this. But our team was like, no, this is really messed up. So you get into these situations where there's no clear answer. Yeah, there's a $200 course

helping people overcome their feelings of white supremacy. Well, I mean, I'm glad they won't overcome that. That's great. Correct, correct, right. So I think by deleting that course, we should keep it. But yeah, we got into all these debates all the time. For anyone listening, I hope you know when you're like, is there a niche for my product? Yes, there is a niche for your product.

So you were building Teachable for say eight years before exiting. I feel like building in your twenties up until your early thirties, that is when you're developing your identity. How was that, you know, building a company that just got so big and you became such a public figure at a young age

while developing your own identity? Who am I? What do I want? How was that for you? Cause I know for me, I mean, BossBib's so much more than teachable, but I was forced to grow up so fast and at some point had a full identity crisis.

I was like, wait, I have built something from a really old version of me. And now I'm figuring out how do I fit with it? So I'm so curious about that. I think what ended up happening and maybe it happened to other people as well. I felt like professionally you advance relatively fast, but on the personal side felt like I was in the state of arrested development a little, and it was also true for a lot of our team where we ended up as a team getting

very close to each other in a way that yes, we're building company together, but we're also mostly all kids in our twenties living in New York, going through life together. I mean, it was a blast. I couldn't do a lot of that again because like work and life just overlapped in every way, shape or form. Like a couple of my closest friends were people that worked for me who now have gone on to start Circle, right?

Like we were also just people going through life at the time. It was an experience again, I wouldn't trade it for anything. But building a company now in my 30s, it's very different. There's a clear separation between this is my work and this is my life. In your 20s, it's all encompassing and, you know, it's kind of all you do. Yeah, and you kind of don't need that work life. In your 20s, it's all encompassing and it's kind of all you do. Yeah. And you kind of don't need that work-life balance in your 20s. It's such a great time to get out there and explore. But I think you hit your 30s and you're like, wait, there's actually

more to life. Cool. How does it all fit in? So what led you to wanting to sell at 31? We decided to sell at 30. The transaction cleared at 31. If I had to put it down in one sentence, I think I was tired. At the time, it was more that this offer came in opportunistically. I felt it was stupid to not at least cure them out. I really liked the people we sold to. It was a company doing exactly what we do in Brazil, but there are two founders, founder-led, founder-driven, same mission. So I sat down, started chatting with them, and realized that, hey, you know, this could be a good outcome because I mostly didn't have the stamina to go another five, seven, ten years or whatever. As soon as I could validate that the price was fair, it was a good enough price, I thought about it for a bit, but eventually I think the tiredness was like, made me feel like

this was the right decision. As you were building with a venture-backed company, was there a limit to how much money you were personally taking home? So then when you sold, was that just like, whoa, this is mind blowing? I mean, regardless, but venture-backed, I'm sure there was a cap, right? 100%. So different founders have different opinions.

For me, I started by paying myself nothing. Then it was $70,000, which is not a lot in New York. Eventually I kept giving myself raises, but at 150 K was tapped out, which to be fair, no dependence. It wasn't like a crazy extravagant life, but there was nothing I wanted to do that I couldn't. So the money was a motivator for sure. But at the same time, from a lifestyle perspective, I didn't feel like I was like not doing a lot of the things I wanted to do.

So how was that you turned 31 and all of a sudden, financially, your life completely shifts. This is going to have the world's smallest violin playing for me. I still remember the day I got a lot of money wired to my bank account. At the time, it was COVID in New York, so I was isolated, locked in my, you know, 300, 400 square foot apartment. So the actual day I couldn't do anything. Honestly, it did feel like there was a bit of a weight lifted off and once it settled in, I mean,

it definitely was something that it just gives you the sense of freedom that I can go ahead and do anything where it's less about the dollars in the bank account, it's more the freedom. Specifically, the biggest inflection point and how I felt didn't come when I got the money in the bank. It happened eight months later when I quit my job of being CEO and I felt like, wow, now I can breathe.

Was freedom a driver for you when you were building this? At the time, this sounds silly, but everything just felt like a game. We had a certain revenue number. I wanted to advance to the next level. I wanted the revenue to go up. So it just became this fascinating intellectual problem of this is a business. How can we do better next month? How can we do better next year? And because it's a startup, everything changes so often that it's very, very stimulating. It's really fun. And as stressful as it is, eventually, like that's

why I'm doing this again, you tend to miss playing that game. I can imagine receiving that too. And then stepping down as CEO, again, coming back to the identity. Was there any work you had to do around your identity? Because all of a sudden you're in a situation where you don't really ever need to work a day in your life again. You know, you're very well known. This was very public. How did it affect you as a human and your identity?

I've heard a lot of founders say that they were almost like depressed after selling their company. They had a loss of identity. Personally, I felt fantastic. I traveled. I basically devoted myself to a bunch of side quests. Like I went, I wanted to get very good at surfing. I wanted to get very good at tennis. Spent a lot of time with my parents. So for 18 months, I think I kind of just traveled the world. I ran a venture fund on the side. So it's working three, four hours a day, which is honestly perfect to still feel engaged, but I had complete freedom. And to be honest, I felt pretty good.

In my mind, I was like, I'll go travel for some time. I'll get the travel bug out of my system. The travel bug never left. It was only after 18 months, what I realized was as good as my life was, I was missing the idea of building something. I was missing the idea of doing work that was meaningful to me,

and that's why I decided to step back. Yeah, I guess if you say you love the game, you must miss the game. Of course, I feel like I'm an athlete and business is my sport, and at 32, 33, you're too young to chill and give up on your sport. You have one more big swing in you.

So thinking about when you were gonna do your next thing, your motivation must have been different. Correct, it's not about the money anymore, as much as if you're playing the sport of business, money is how you keep score, but it's less motivating. As a result, this time I've been far more generous with the amount of equity I've given every single team member. Small things like that are completely different. Like additional money,

at this point it will not change the quality of my life one bit. Yeah, that's really interesting how you're approaching it differently. Do you feel like it's shifted your level of hustle? I think your level of hustle evolves, but for whatever reason, the point to prove hasn't gone away. And maybe it's because this is my second company, not my 15th company, but I feel like the point I have to prove is bigger than ever. And maybe this is untrue. There's this narrative of like, I don't succeed now, everyone will say it was luck. Like, you know, once you're lucky, twice you're good. So in a lot of ways, the pressure seems more

because there's this weight of expectation. I don't know if it's something I've put on myself or it's what I feel externally, but I don't know, I spent two years sitting on panels telling people how to build their company, kind of embarrassing to not do this well myself. So the weight of expectation, I think, has driven me pretty hard this time as well.

I think you just get better at distilling what matters and what doesn't. The first time around, I felt very, I don't know if insecure is the word, but I felt like I have no idea what I'm doing. So if I read a book, I should do that thing. If I talk to this other person, I should do that thing. Now I feel like no one knows what they're doing. So you're better off just relying on your instincts. That's really interesting. So let's talk a bit more about that of the difference the first time and second time. What are some of the things you're absolutely going to avoid the second time over?

Initially, when it came to like managing a team, when it came to like running an organization, I felt like I had no idea what to do. I would read all these books, I'd read all these business books, I'd talk to all these other people. And I would immediately take their advice without realizing that being authentic to who you are and your style is incredibly important. I can either be very good at being who I am, which is someone who operates in a very hacky way, fast.

And things I do are not perfect, but they happen really fast. I can be very honest in how I communicate with my people, and I can do it in a way that's authentically me. And I realize that will work better than pretending to be a hyper organized person because I read some management guidebook or whatever. So it's realizing just trusting yourself and your instincts matters quite a bit. Let's dig into that part a bit more doing things really fast and being hacky because I know all the founders listening to this will relate.

And when you have people on your team that are not super entrepreneurial and everything needs to be detailed and organized and they wanna go slow. And I mean, I bet your experience as Teachable, when the company grows so big, there's all this red tape and layers and levels. How did you manage and balance that as a founder that just wants to move fast?

So at Teachable, I think I did a terrible job by the end. And I think that's why partially I was so burnt out. But what we did is we brought in all these executives. They all had very impressive backgrounds. And again, they are generally smart people, but it was so different from the DNA of how I ran the company that I sort of just let them run things the way they want.

And as a result, things grinded. We had to have meetings about meetings. One of the things that drove me crazy is I remember our designer wasn't working on product design for our customers. She was making a deck look prettier for an internal presentation. It's like, what are we doing?

And things like that, it also in turn made me realize in retrospect that if it gets to that point, I don't even think I'm the best CEO for the job, but I had so much ego attached. It's my company. I have to be the CEO. Today, if I feel similarly, I'll be the first person to step away. But I think retaining that sense of identity is going to be critical as a company. Do you feel like you're doing it with a different level of confidence this time round? Like, wait, I know the way I do things serves me. And I feel confident maybe putting that out to team that have these fancy backgrounds, but have never really built a company before.

Put it this way. I don't necessarily think I am substantially better as much as I realize everyone is faking it. So if we're all faking it, we may as well listen to what, you know, what I feel more comfortable doing. There's a lot of people who are like second time founder, you're gonna make no mistakes. I just think we're gonna make an entirely different set of mistakes this time.

If you think about how long it takes to get good at something, two repetitions is not enough. You need many more repetitions. I'm in my second repetition, so we'll still make mistakes, probably just different mistakes. Have you made any mistakes with Carrie, which we'll talk about that you're like, wait, I thought I learned my lesson on this the first time.

Why am I doing this again? I think we make different mistakes. One of the things we've been good at this time is keeping the team small. At Teachable, things were really fun and really enjoyable till about 30 people. At Carrie, we're still 14 people two years in. So I think we've done that very well. Things that have been difficult are, I underestimated the difficulty of the industry. There's this whole like, I don't know, people say this half jokingly, but they're saying, we're not doing this because it's easy, but because we

thought it would be easy. And that's the reality of a lot of what we're building with Carrie where, because we're dealing with people's dollars, there's a lot of regulatory work, compliance work, like a chief compliance officer was in our first 10 hires. There's a lot of hard things that I underestimated that had to do with the nature of the business that I only learned on the fly. What's so interesting for me is when I was growing Boss Babe at a certain point,

it was almost like the company was growing and I wasn't at the helm of it. It was just growing. And I actually stepped away as CEO and was going to sell and realized ultimately TLDR, my face was way too attached to the company to sell it. And so ended up stepping back in, but redoing everything. I cut down my team significantly, our product suite expenses, like you name it. I trimmed so much down and had the realization that actually I know what kind of company I love to run. It's a lifestyle business.

I'm gonna own that instead of trying to build this thing that doesn't feel like me. And I still, I call it my second time round because I left and came back, but my second time round I still find myself repeating some of the mistakes from the first time. And I'm so curious your take on this cause I just need to learn it.

The idea of higher, slow, fire, faster. What do you think about this? One of the things I need to get better as a founder is I hire from excitement and I fire like five months too late. What's your take on this? I agree with firing faster. I think that's the hardest thing in the world to do. In between, you sort of learn how to do it because you do it and you see how things are better. You realize how it's motivating to everyone else. But then, as in my case, you don't do it for a while, you kind of forget it, right? It's like doing any other hard thing. If you don't do the hard thing for a few years, forget it.

I'll still say the saving grace is it probably also means you're not a sociopath and you're a good person and all of that. Like there are, like, I know some founders who love firing people and I find that exceptionally weird. That is deeply troubling. Deeply troubling as a human, right? I personally think, yes, you must be able to fire fast, but I tend to think at least in a venture backed startup where we have enough cash, we don't burn cash easily or whatever, we should hire faster.

Like it's okay to hire someone. And again, this is for us, it may be different for you. If I have seven out of 10 conviction, as long as I do it fast and get rid of them if it doesn't work out. Because the reason I don't think hiring solely works for me is I don't think I can really tell beyond like a 75% confidence if someone's going to work out until they start doing the job.

No matter what I do in the interview process, I'll still get one out of four, one out of five hires wrong. So if I can keep it at one out of four wrong, one out of five wrong, but do more faster, it will result in a better outcome for me. That makes a lot of sense. And what you said specifically around, you can hire fast as long as you're willing to fire fast. I think, yeah, I get to learn that lesson. I'm learning.

And people love saying, right, like, you gotta hire A players, A players hire A players, B players hire C players. I think as your company grows, you're going to have a large enough team. It depends how you define A or whatever, but being too much of a perfectionist and keeping roles open too long can also hurt you.

And sometimes someone pretty good with high upside is totally worth it versus waiting for the perfect person. Totally. Like even if they don't have all the skills, if they've got that attitude to learn, it's the best hire you can make. How do you feel, because I see this a lot, especially in the course creation and information industry of a lot, like you might've had this teachable where your team might be seeing the revenue that creators are making and they either come and haggle you hard for comp or they wanna leave and do it themselves.

I can see you smiling. Was this something you dealt with? Dealt with it quite a bit. The funny part is at least what we saw is a lot of people saw this and they tried to do it and most of the times they found it really hard. Yeah. Building an audience is not a joke.

Like of all the people from Teachable, and we probably over the course of my tenure hired 250 people, I can only think of one person that has gone on and built a successful content business at least 30 or 40 tried what they found is building an audience is really, really hard. It can take so long to get to $10,000 a month in revenue. And then they were like, wait, I make $100,000 a teachable and have health insurance and have all of this. And I could not work that hard.

This is actually a pretty good gig. They saw that. The other thing we saw is a lot of people kind of lied about their numbers in terms of the creators and stuff, because again, we process payments for everyone. And we'd see people talking about like, oh, like analysis of my six figure launch. It's like you made $12,000,

the rest is an uncollected payment plans that are not coming through. And there's, I think a lot of people were actually turned off by the industry by the end where they just saw so much inauthenticity, not everyone by the way, some of the best people have always been very transparent, but as you know, in the space, there's a lot of people who talk a big game.

Oh, it's prolific. Especially if they're trying to paint this narrative of external success. Yeah, we see it all the time. We're like, wait, I was inside there. I saw how many students you have. So what problem are you solving with Carrie? And why did you want this to be the problem you solved? I never thought about personal finance, money too much until a few months before selling the company.

At the time, I knew it was going to be a good sale. So I hired lawyers and accountants to like look through everything, see if there's anything smart I could do to save on taxes. And they ended up finding what I didn't know was the largest tax loophole in America. But it basically like they set up a couple of structures, a few trusts, things we can get into details, they're kind of boring. But the short version is they managed to save me millions of dollars just because I had that conversation. And that was an eye-opening experience to me. And the more I dug in, I realized the US tax code is written in a way that favors business owners over everyone else. But the average business owner has no idea.

Like they have no idea how to do it, how to like leverage it. So I knew if I started another company, it would be a version of this idea, helping business owners basically grow their net worth by saving money on taxes. I would love to talk to you about that, because I feel the same way as many of the business owners like great I'm making money I have no idea what I'm doing with my money and like I have help thank goodness but there's all of these letters and words that it goes so over my head. It's intimidating like the US tax code is they're adding 150 000 words a year like no one knows the entire body of it. What I tell people

though it's a little bit of a mindset thing, that complexity is actually going to help you. Like every time there's, in addition to the tax code, there's more loopholes, more advantages, more opportunities. If I zoom out on like my career or my life, every business I've ever built has been serving business owners in some way, shape or form. So I also look at this as a continuation of that mission, like part one, help people make money online, become business owners. Part two, help them keep more of what they make and grow their net worth. So starting foundationally, what should a business owner know about what they can do with that money? First things first, right? Like why is being a business owner awesome? Like before we get into the monetary side, I think the mindset piece of a business owner is really great because when

I talk to someone who's earning a fixed salary, when it comes to personal finance, they're always focused on cutting, like killing expenses, skipping the latte, whatever. As a business owner, you know this, I know this. Revenue is sometimes an easier line item to move. You're not fixed into a certain number. You can always make more. So from a mindset perspective, I think that's the best part of being a business owner. Now, when it comes to the tax code itself, I think that's the best part of being a business owner. Now, when it comes to the tax code itself, I think there's a few categories of things. One is expenses. There's a lot of things in your life you can write off as a business owner

that you cannot as an individual employee. Like, again, we're in a studio here. If you were creating content for a job at a company, you wouldn't be able to write off a studio you built in your house. But if you do content for a job at a company, you wouldn't be able to write off a studio you built in your house. But if you do that for a business, you can write off the percentage, square footage, pay rent or mortgage. Same with the home office.

And there's all these expenses you can only write off as a business owner. I have a secret announcement. We are working on something absolutely phenomenal for Black Friday. And here's the thing, you're only going to find out what this offer is if you're signed up to the Black Friday list. Now, I do not do Black Friday deals for the whole of the month. It's very much going to land on Black Friday and it's one of those things that you're really going to want to make sure you're on the wait list for

because your jaw is going to hit the floor when you hear what we're doing. It's wild. So what I want you to do is head to bossbabe.com forward slash black Friday and get yourself signed up. The thing that we are releasing on black Friday has the potential to completely change the trajectory of your business to close out this year. And for all of 2025, you have to be on the list. You won't hear about it if you're not. So head to bosswave.com

forward slash Black Friday. I'll also put the link below so that you can jump on the list and make sure you're signed up ahead of Black Friday. Let's take a quick pause to talk about my new favorite all-in-one platform, Kajabi. You know I've been singing their praises lately because they have helped our business run so much smoother and with way less complexity, which I love. Not to mention our team couldn't be happier because now everything is in one place, so it makes collecting data, creating pages, collecting payment, all the things so much simpler. One of our mottos at BossBabe is simplify to amplify and Kajabi has really helped

us do that this year. So of course I needed to share it here with you. It's the perfect time of year to do a bit of spring cleaning in your business, you know, get rid of the complexity and instead really focus on getting organized and making things as smooth as possible. I definitely recommend Kajabi to all of my clients and students. So if you're listening and haven't checked out Kajabi yet, now is the perfect time to do so because they are offering BossBabe listeners a 30-day free trial. Go to kajabi.com slash boss babe to claim your 30-day free trial. That's kajabi.com slash boss babe. And then when it comes to, so we're writing off expenses,

then let's say end of the year, you're looking at tax planning, thinking about do I put money in 401ks? Do I put some money into index funds? Do I put it in high interest savings account? How do you think about that? This is gonna come out before end of year. And I know that's when a lot of people are just scrambling.

The other important thing to look at, and I don't know if you've done this, are you an S-Corp or how are you incorporated as a business? So I'm a C-Corp, but I am also an LLC. So I get paid through an LLC as talent of the business. Yeah, so that's the other thing most business owners should have someone look at and you have, is initially when you start out,

you're either a sole prop or an LLC where everything flows down to you. Eventually, once you make enough money, you either want to be an S corp, which lets you save on self-employment taxes and pay yourself a salary, or you can be a C corp, which gives you the benefit that I use called QSBS,

which is when you sell your company, you can pay no taxes on tens of millions of dollars. So I'm glad you've had someone look at that, but incorporation is the other big thing. Then when it comes to 401ks and stuff, as a business owner, you can basically rig the game so you have the best benefits out there. 401k is one of the best ones. If you're self-employed you get access to a solo 401k which is the most powerful account, retirement account for anyone in America since it lets you deduct

almost $70,000 every year from your taxes. But because it's your own private 401k, you can invest it in anything you want. Like not just stocks, you can also do real estate, crypto, startups, anything you want. And you control every single aspect of it. Well, I know I always max out my 401k, but I don't think I know where it goes. So maybe I should look at that.

So the solo 401k, you can invest it exactly how you want. The other advantage is if you're married, you can add your spouse to the business and collectively you now get 140,000 tax deduction. So super massive. If that's not enough, you can set up something called a defined benefit plan,

which will help you collectively get 200 to $300,000 in tax deduction. So all of that like really compounds to it. Another fun one I always tell people is business credit cards. Business credit cards can, you can use credit card points from your business for yourself. And once you learn how to do that, you're like traveling in style for free, wherever you go. It's the best. What I also learned with the business credit card is you can buy gift cards

on it. So I know it's not always the best use of your points, but sometimes they run deals and I'm like, Oh, I'll get some blooming deals. I'm biased. I think if I think you got to do it on travel, I feel like if you know what you're doing with travel, it's the best. Like any, all the cash back is not worth it. Once you learn the travel game, it's also kind of stupid. My friends are like, dude, you made enough money. Why, why, why are you doing credit card points? One, it's how I was raised. I still struggle. I can't buy $10,000 flight. I'll just struggle with it. But if I can rig the game and make it seem free

and use some credit card points, it's totally fine. Also from a psychology thing, my parents will never let me buy them a flight. Still? They just won't. They'll let me pay for the vacation, but like their flight, no. Wow.

But credit card points. If I use my points, they don't care, that's fine. Wait, so how do you learn the game of credit card points? Cause I'm terrible at this. I'll give you the 30 second tutorial and then we can go into it further. So you get a bunch of credit card points. What card do you use?

I have two. So I have Chase Inc with one of my companies and I have the Amex Platinum with my other. Perfect. I have the exact one, JP Morgan and Amex. Okay. So you log into Amex, you see I have 250,000 points. The mistake most people make is they go to Amex travel, they look at flights and they book over there, but you lose most of the value

by doing that. Instead, what you do is like, I like I fly to Dubai a lot, I'll create an account with Emirates, I'll search for the flight on Emirates and then I'll transfer my points in. And simply by doing that, I'll probably save 80 to 90 percent. Like, wow, that's the difference. Yeah, like that's how you fly Emirates first class for one hundred and fifty thousand points versus like seven hundred thousand points. So and we'll keep going on this, but I have to ask, how are you still so humble and not flying on your private jets everywhere

and doing credit card points after this? I think it's how I was raised is what it comes down to. And don't get me wrong, like I'll fly in a lie flat seat every time and I don't feel like I'm limiting what I spend on at all. But at the same time, I think how you're raised is like such an important part of it that it's hard to kind of break away.

My narrative to myself is to be more comfortable spending more. I bought a car three weeks after I sold the company and I bought a secondhand car. No you didn't. Because it was used for six months, it was $10,000 cheaper, it felt stupid not to. So, yeah, I'm trying to change that

but I do think it's better than the opposite. Like I have friends who are looking at buying a yacht and it's just like a lot of those things. I mean, and you know what the fight club quote, the things you own end up owning you. And I think being able to live the life you want is like money is freedom and it's not the possession of random things. But that, I mean, so we need to talk about the way you were raised because that is not a common mindset. I feel like we live in such a materialistic world where I'm reading Andrew Wilkinson's book right now,

Never Enough, it's absolutely amazing. And he was talking about nothing he ever made was ever enough and all these business owners he met that had exited for so much money, you know, they were like, if I could just double it, if I could get, like there was never enough. So what was it that has allowed you to feel like there's enough and you are not driven

by the egoic materialistic things? So this is a theory, it's not fact, but I think a lot of this comes down to how you were raised and like how your family talked about money and how they in turn, so for a lot of this comes down to how you were raised and like how your family talked about money and how they in turn, so for a lot of people, they struggle with this and at first I was like, do you just get your shit together? But then I realized, no, it's actually how they were raised

and for a lot of people, there's this inherent sense of scarcity of like, it's never enough no matter what. For me, for whatever reason, we were raised, you know, middle class, maybe upper middle class by the time I reached college. And it was, I think, a point where we always felt like we had enough and there never was that sort of sense of scarcity. But I also just think some of it is kind of luck, right?

Like, we don't choose how we grow up and all of that. But for me, I do know, like like any sort of the pursuit of more wealth, all it does is it changes the number I go to the grave with. It doesn't change the quality of my life anymore. So did you feel like your parents didn't often say no, we can't afford that? Because one thing I read in Andrew Wilkinson's book, which was so interesting was he grew up, he went to a private school or like a really fancy school and he grew up in a neighborhood of lots of fancy houses but he had the smallest and his family could barely pay rent on it and he was just seeing that he never measured up materialistically. Did you feel like you did? I didn't think about it,

which in turn probably makes me feel like it was fine. I do remember early on when I first came to America for college, my parents had saved their entire life to send me to college. So I had a lot of guilt that I was like, I need to do well, I need to go to class, I need to be good. Halfway through, I started paying for college myself. And at that point, I just felt this massive weight lifted. I'd never go to class anymore. Now it's like, it's my money. It's so crazy if I go to class. But once I broke past that, like, which is why I think money is and was the most

meaningful thing in the world at that point. But it's just that there was a threshold beyond which it didn't change anything. Like there's not that much difference in like flying private, I don't care for, right? Yes, I do want to lie flat on a bed when I'm flying to Europe, but it just, the pursuit of random things, do you just run out of things that kind of move the dial from a happiness perspective?

I love that. Okay, I had to ask that, but pivoting back to Carrie, if a business owner is listening and they're like, okay, tell me a little bit more about carry. How could that help me in understanding what to do with my money and how to get organized? Yeah, so what we've done is we looked at all these accounts like the one person 401k IRAs, soon we'll have HSAs.

These are all special types of accounts. The government gives you a tax benefits. We've built a platform for people to create these accounts and invest it in pretty much any asset they want, whether it's like stocks or ETFs or crypto or alternatives, whatever it is. That's what we have built today. If you look at five years from now where we want to go, it's basically going to be this engine where you come in.

We learn a little bit about you, who you are, what your business does, how much it makes, we'll give you a list of strategies to help you save money on taxes. You can implement them on autopilot and then we'll also eventually file your tax return for you. So we're signing off on it. But that's the long-term vision where it's like, you don't have to worry about any of this. This is like a tax saving tool on autopilot.

And who would you say is the absolute ideal client in terms of revenue level, savings, employees? the ideal client in terms of revenue level, savings, employees. So our perfect client right now is the person who can take advantage of the one person 401k. So what that means is you are either an independent business owner or you have a couple of partners and no employees or you and your spouse making I would say at least 100,000 a year somewhere around there all the way to much more than that. Typically for people like that, we can get them a tax deduction of tens of thousands of dollars.

They have this account that's more powerful than anything else. They can invest in any asset class, grows without taxes. They can borrow money from it if needed, even get a tax credit for setting one up. So that's sort of the sweet spot today, but we'll keep broadening who that is.

And for someone listening who just is hearing tax credit and deductions is already confused. I know, I know. I feel so bad about this. Is that something that is taken care of when they sign up? Like it's step by step and easy or they're going to have to learn it? We're trying to make it as easy as possible. Basically, what happens, roughly what happens is you make, let's say $100,000 a year. With the one person 401k,

you can put in up to 30 to 40k in this account. So now your income that's taxed is 100k minus 40k, only 60,000, so you save a lot of money on taxes. Now that $40,000, it's not just chilling. You can invest it in anything you want and any growth inside that account, there's no taxes. So you're getting dividends, you're getting interest, you're buying and selling.

So by the time you retire, you put in 40,000 every year, you have millions and millions of dollars that you get access to in retirement and you've saved so much in taxes just by doing that. So is this a place people put money and then earn passive income from or is it ideally they put money in and they don't touch it for another 23 years? So they put money in and they can invest it however they want. For people who don't want

to deal with that, there's also a button where it's like this is my risk score just invest it for me. Got it. But otherwise it's an investment platform where they can choose exactly what to invest in. And can they decide if they want to be taking money out or will you guys say hey we would recommend you just keep things in? Because it's a retirement account, you cannot typically take money out till you retire. However, you can borrow up to $50,000 as long as you pay it back. So you can borrow money for short term needs, but you can't just withdraw money until retirement.

Interesting. And I also love that this is geared towards solo printers because I am seeing such growth in the solo printer space. What do you think? These are things that typically your company would do for you. So that's the other thing, right? Where like your company takes care of this, but if you work for yourself, you need someone to help you out. And that's where we come in. Yeah, I love that. I'm just seeing so many people either leaving their full-time jobs to be solo printers and just consult for a couple of companies or work fractionally for a couple of companies or decide, you know what, I am a creative, I don't want to manage

a team, I want to go into business on my own. Are you seeing that? Absolutely. Also, a lot of our customers, funnily enough, have a full-time job and also a side hustle. So they use this with a side hustle. So you don't, if you have a full-time job and also a side hustle. So they use this with a side hustle. So you don't, if you have a full-time job, you can still set up the one person 401k just for your other business. So smart. I'm going to put the links below for anyone listening that wants to sign up. I'll put all the links and stuff. So another thing that I want to talk about that you're doing with Carrie, I get your investor updates. I'm always just so interested by them. And

it looks like what you're doing with Carrier is very similar to Teachable in that you're really focused on recurring revenue. Can you talk about that? We spend a lot of time thinking about what makes a fundamentally good business. And I genuinely believe selling software is a really good business because there's no marginal cost as you add more customers.

And if you get people to pay you monthly or annually, even if you, let's say, are are churning three or four percent a month, you're starting at 96% of last month's goal automatically. So recurring revenue has always been a big theme. Even now, like we floated the idea, right? Like we have courses, but like, what if we sell courses one off? I've told my team, it doesn't move the dial. Like I don't care about making a hundred thousand dollars in one-off revenue. I'd rather have 10 or $15,000 in recurring revenue. That's so interesting. And so you're really thinking, let's

shoot for long-term revenue that's sustainable versus those cash influxes. Correct. And again, this is also biased, by the way, by the type of business I'm running. I'm running a venture-backed business. We don't get profits. We don't get distributions. Making more money today doesn't help me. I'm building a business that can eventually get to

billions of dollars in annual revenue. And for that, it's a different playbook. If I was a creator, I would feel very differently where I think there's always room to have good one-off revenue and so forth. Yeah. But even as a creator, I feel like I've always had memberships and I also have a product-based business where it's on subscription. That for me just takes so much of the weight off. And I always say you don't have to have a membership, but even if you've got long payment plans or something

and you're delivering and you can somewhat predict what revenue you're bringing in, it just helps you make smarter decisions generally. The predictability I think is the best part, right? You can account for how things are going to go, and you truly get off the whole treadmill. Like if you have to put in more hours to get more dollars, this you can step away from, and it just makes for a much more sustainable business. What made you want to raise venture again for this company?

The reality is it's just difficult to build a fintech company. Like because we're dealing with money, we have a lot of compliance costs, software costs. Things are just harder. With that said, the way I raised venture, the first round of funding was my own fund. The second round of funding was a bunch of friends

in which you participated, a lot of other people participated. Our institutional round, we've only raised one and it may be the only round we raised. Like the last round we raised was a series A and the narrative I've told our team is, let's imagine we will never raise another dollar again and this is it.

So yes, we're raising venture, but I think we're not on the venture treadmill where you keep trying to raise the bigger and bigger round and then spend your time optimizing for the next round versus just building the biggest business you can. Yeah, that's what stressed me out when I see some companies on that treadmill of like, they are just thinking

about raising money constantly and it's just bigger rounds. It's nerve wracking too, because you're like, I have six months of runway or I have to fire 55 people and ruin everyone's life or I raise this round. And at Teachable, we raised $12 billion, but still had nine in the bank when we sold.

So we were always quite close to profitability. And that's how I would like to get carried too, where we're burning a little bit of money, but it's not like how much we're making and how much we're spending are diverging, which to me just seems too stressful. Do you feel like it's taking a lot of self-control to do it in a way where,

because you said you have 14 team members, you're not just, you know, you get a bunch of money, you go and hire a ton of people and just move super fast and like scale it all costs. How are you balancing that? To be honest, I think the fact that I made a lot of money and bought a secondhand car is not unrelated from how I run my businesses. When it comes to running a business, or anything in life, I'm a very competitive person and I don't want to lose. And to me, increasing your burn rate dramatically, the speed of outcome could happen faster, but you risk a little bit more.

And the way I look at it, I don't want to lose. I will not lose. And as a result, I want to kind of take any luck out of the game. And keeping a low burn rate is a part of it, but it's also part of my personality and you know how I operate. So aside from the kind of red tape and regulations and things, what other challenges have you had this second time round? A challenge we had teachable, it's still too early to say if we'll avoid it, is we grew pretty fast to about 10 million in revenue. But past that point, our churn was quite high. So every additional step going from 10 to 20 was quite hard because we were churning 5-6% every month.

We built this really, really strong sales engine while our product retention wasn't as good. This time what we've done, and again, we'll see if it's a good idea or not, is for the first two years we spent nothing on marketing. We have three marketing team members, but $0 in any kind of acquisition with the idea that I want to get to a million in revenue. I want things to just feel really good, feel like there's expansion revenue, and only then start pushing. So it's only really now, like literally this quarter

is the first time we'll start making a real marketing push beyond just content, because it took two years to feel good about everything. To be determined how it gets at 10 million and so forth, but my hope is once we get to those revenue numbers, the core product just feels so good. A lot of the growth comes from within. Yeah, so it's not that leaky bucket of just filling.

It was a leaky bucket for quite a while at Teachable because what we did is we got very good at like selling people on the idea of starting a course. But as you know, a lot of times they never actually took the next step. Yeah, that makes total sense. So you said right now you've been bringing in users through content. So what does your marketing plan look like so far? Because one thing you've done really well in both companies I admire is just not

attaching your face to it really. Like it exists without you. So I would love to hear the content plan on that. So what I've done this time is also because I'm interested in this is I've now become, well, I'm not a CPA, but I've become quite good at learning the tax code inside out. And speaking about it, like Twitter is probably our biggest channel. Again, because this is a venture backed company,

Carey is always going to be the brand. I mean, that's the name I'm going to be representing versus like me being the primary brand. But I think that's been a big part of it. Secondly, we're investing a lot in education because these are, let's face it, complicated, dry, boring topics. How can we actually, how can we kind of make it interesting while also not going

to full like TikTok influencer where you're just giving wrong advice? It's a delicate line to straddle because you talked to a CPA, they're super boring. They're going to say it depends to everything. TikTok influencers are going to go too far in the other direction. We're trying to be right in the middle. How can we keep it somewhat entertaining while also adding a lot of value? When it comes to numbers and metrics that you're really focused on within marketing, is there a number that you prioritize? Is it certain amount of followers or email list or what do you think about like that?

Especially when it's for working with a creator or something, most of the traditional metrics I find to not be super useful, like followers and stuff, it can be weakly correlated. Typically the only way we found to evaluate if someone's audience is effective is testing a campaign out with them and seeing how much credibility they have

in their specific vertical. When it comes to the metrics we look at on our end, I mean, honestly, there's only two real metrics. It's number of customers, and then how many assets or are the customers actually investing dollars on the platform? So as an example, if someone invests dollars on Keri, their retention is almost perfect.

We've churned like maybe 10 people total. If someone doesn't invest dollars, we lose close to half of them one year later. So there's a big difference between 97% retention one year later or 50% retention one year later. So then it becomes, how do we find customers qualified enough who want to actually set up the accounts, invest with us and all of that.

I love that. So for someone listening, if they feel like they would be the perfect person, what are their first steps that they're going to do when they sign up? Yeah, so it's all self-serve. It's kary.com, which is a domain that costs quite a bit of money. I can imagine. But it's super worth it because when you're building a financial institution, trust is really important and you're not going to get scammed with a site with a good domain. Like it's such an easy trust builder that it was super worth it.

But yeah, typically people go to carry.com. They can then if they, if they are a solo business, I would say they can set up a solo 401k, which is fully self-serve. It can guide them as to what to do to save money on taxes. And it's probably the best place to get started. We also have an education library. We have about 20 premium courses that we internally think of is like, what if we can build the masterclass for money, the masterclass for personal finance and

taxes, so if they get stuck at any point, there's that we also have the ability to add a financial advisor to their account. So then there's a human who can come and point them in the right direction and kind of walk them through what's needed. I love that. And you changed the name, right? What was the story on that? The original name was Ocho, OCHO.com, which I love, but we got a lawsuit.

And the funny part is this actually at Teachable 2, we used to be called Fedora. I've been got a lawsuit. So I'm like, wait, I didn't know that. Yeah. Yeah. We were called Fedora, which is not a good name. So we got, we had a lawsuit then change our name. This time too, we had a lawsuit, changed our name.

So the rest of the team was stressing and wanted to fight the lawsuit. I was like, look, at the time we had less than half a million in recurring revenue. Like it doesn't like, yes, we're emotionally attached to the name, but I bet we'll find something better. And both times around, I think we found a better name.

So. That's such an interesting mindset too, patch the name, but I bet we'll find something better. And both times around, I think we found a better name. That's such an interesting mindset too, to have as a founder where, you know, something like that will come in and you just know it's not the end of the world. I've dealt with this before. This is just the cost of doing business and you move on. But for your team, it's like, oh my God,

this is, is there anything else, any other mindset or approaches to business you have like that that you just are noticing really serve you? I think the brute force, like a lot of people say, how do you get okay with the ups and downs of being a founder? And one, you never fully get okay. Like I'm still on an emotional journey all the time. But after 10 years of doing this, like the highs are less high, the lows are less low.

You kind of normalize a lot. So many, many times when something bad happens, my internal narrative is like, you've seen this a million times before, it's not going to last. But equally, I'm also a bit of a Debbie Downer when things are going amazing, because I'm like, that's not going to last either. So just the repetition of having done this a lot

definitely helps out psychologically, emotionally, all of that. And how are you approaching having a personal life separate to work in this time round? Like do you have specific boundaries in place? This tends to happen a lot, but as a founder, very often your early team resembles you in terms of demographics, age, all of that. I think our team is a little bit older. So as a result, I think

there's more of a separation. I think at Teachable, we probably had a very strong happy hour culture. Everyone went out together after work all the time. This company, everyone wants to, but we keep rescheduling because people are busy, things come up. I mean, so everyone really likes each other, but it's a very different sort of relationship. When it comes to personal life, whatever, I always think at a startup, I've always worked hard, but we've never been the working 14 hours a day or whatever. I get into the office, aim to get in a little bit before 10, I leave at 6.37,

which is, it's kind of a normal sort of life. I have time to work out or play a sport before work, socialize after work, so it's quite a normal life. The hard part is your brain. Your brain is always thinking of work and taking and all of that. But I mean, at the end of the day, that's also why we do this.

Yeah, it's so addictive. Do you have any boundaries around like being on your phone or when you do and don't do emails and things like that? I've given up on email. Tell me about this. I ironically enough, the only email inbox I monitor these days is the support channel for Carrie. But my actual email, I now have like five or so,

I have my teacher, I've just like given up. Like if I happen to see something, it's good, but I'm most responsive on text, WhatsApp, even like, I think you reached out on Instagram DM, right? So I think all the DM channels, I still check. Email has just become a complete unmitigated disaster. So, OK, I've tried this. I've tried breaking up with email so many times, Tessa, I will tell you.

I've even put the automated responses on like, hey, I don't really check my email and they just email again. How do you let go of that feeling of like, I need to reply to people? I need to do this? So I have a few inboxes I'm not logged into in months, so that helps. So how do you personally get okay with that? I think it just became so chaotic and overwhelming where it's not even that I'm okay with it, I'm so afraid of what's in it.

I don't open it because of fear. Now there's so much anxiety built up of like, what's six months of emails that have not been looked at, so I just don't look at it from like in a place of avoidance versus a place of strength. Do you have an auto responder on to tell people you don't look at it? No, no. Like I just figure if it's important enough I'll hear about it elsewhere but I would also say and maybe this is like some form of ADD or whatever I wouldn't advise anyone to live their life the way I do. I frequently have a danger of like, I realize I hadn't paid my electricity bill for two years. I wouldn't

recommend following in my footsteps because a lot of my life is very chaotic and very disorganized. And so do you ever worry you're going to miss out on a big opportunity that comes in your emails? I don't have that kind of FOMO anymore, just because I just think there's always opportunities and stuff right now. Building this company is quite important and I just can't spend my time on all of that. But for instance, I've also noticed with other people, so I do tell our marketing team,

if you're trying to get in touch with someone, don't just rely on email. I think the channel has lost, it's still the best way to do sales at scale. But if you're trying to reach a busy person, you have maybe a 50% shot with email. And did you get that mindset of not having FOMO when you exit Teachable?

When did that come into play for you? Somewhat recently, because even after exiting Teachable, I spent a couple of years as an investor. And as an investor, you're super worried about FOMO. You're always worried you'll miss out on a deal, you'll miss out on something. And then in that period,

I invested in maybe 60 to 80 companies, saw a lot of fit and just realized it's a very hard life to keep up. And if you play that game of trying to keep up, it'll consume you, it'll take everything away from you. So right now I'm just like focused on building the business. Everything else is secondary from a opportunities perspective.

And the sense of if it's big enough, it'll find me. And more questions, I'm just grilling you because this is so helpful for me. Do you use like a project management software at Carry? I don't, but again, I tell people what I've done is I've surrounded myself with people that are very different from me that are much more operational, organized. Nick, my co founder, is the antithesis of me as a human being. I thrive in chaos. I have no systems, but he's very organized. And I think having that kind of pairing is very, very helpful. My to do list is a Gmail draft. When I'll like remember what to do, I'll start a draft, but I'll never update it. So in my draft section, I have thousands of to-do lists. And if I search for something and it shows up in like 10 of them, it's like, clearly this is a task I've been like

putting off. Like paying my property taxes is probably there in all of them because I remember I have to do that and then I don't do it and I'll pay like six months later or whatever. So what if team are assigning you to do something? How would that get to you? We are a largely in-person culture. The downside of that is sometimes when it's important, like if to approve a wire, I will literally have Nick stare at my computer and say, I'm not going to leave

until you do this now because you're going to forget about it. But I do think again, in-person cultures, again, work really well for me, where if my choice was building a remote company or building no company, I would have chosen no company, because I don't wanna spend so much time on Zoom, I don't wanna spend all this time isolated behind a computer.

I realized that was also what was burning me out about Teachable. Like, I think as humans, we are our best when we spend time outside and we spend time with people, when we're moving our body. And a laptop remote job is the antithesis of that. You're isolated behind a computer, indoors,

and I didn't want that. I find that really challenging because I feel like with a remote company, all it is is inbound. 24-7, I need this, I need this, I need this. And I'm like, I just want, I just avoid to close my laptop, turn my phone off. My team hate me.

I'm just like, I'm avoiding and pretending I don't see it because it's too much. And of course a job, it's inherently transactional. You get paid to do a task. I find with a remote job, it really emphasizes the transactional nature while when you're in person, I find a greater sense of camaraderie of like,

hey, we're building this thing together. I also will say it's a little bit harder, I think for creators, because creators, if you are the personality, they are working for you versus if the brand is a personality, we're all working for this thing we're creating together. So it's another challenge I've seen creators have, and all the more reason I think, yes, I got burnt out,

but I think creators get burnt out faster because it's so demanding and you are everything. If you're not producing content, you're falling behind. The team you have, they're working for you. They're not working for this bigger thing. You're all creating together. What's really challenging about that being a creator and a CEO is you're creating content

and running a business and the two of them merging is very challenging. Like as a CEO, as an example, you have to be on a manager's calendar, which means lots of small blocks of time, very scattered, no time for deep work. As a creator, you have to have time to go deep. So those things are just clashing with each other. Right now it's easy for me because I have no deep work. I cannot do deep work. My job doesn't allow for it, but it's okay because I rarely need

to actually do anything in a six hour block of time. But as a creator, you don't have that luxury. So what would you do if you were in that situation? Would you hire someone to do the managerial? Potentially that. I also think there's a lot of creators that find a lot of joy going back to creating. Even if it means trading a smaller business. One of the best examples, I'm sure you know Pat Flynn. He was in his running Smart Passive Income, scaled it quite a bit. It's obviously incredible. He was one of our biggest affiliates, huge fan, but now he's having Flynn, he was in his running Smart Passive Income, scaled it quite a bit. It's obviously incredible.

He was one of our biggest affiliates, huge fan, but now he's having the time of his life creating a Pokemon channel with his son. He's had a million subscribers and he's just thriving and enjoying being a creator for the love of the game. And I think as a creator, when you start a business, it's easy to forget the love of the game. It's easy to forget the things that drew you to do it at first.

And you get so caught up in funnels and KPIs and leads and all that bullshit that, you know, you forget what it's like to actually just create. Yeah. I mean, that's why I almost tried to walk away from my company because I was like, I'm running a company and I'm a creative, but I'm not doing anything creative. Everyone's telling me what I should say, what I should record. And I'm like, I just want to do what I want to do, but that's really challenging. So when I mentioned the solopreneur movement, that's what I'm seeing a lot of

is people scaling back their teams to get back to doing what they actually love. There's a creator I really love, Vanessa Lau. She had built this huge business as a creator and hated it. And she burned the whole thing down, refunded everyone and was like, I'm going to go back to just creating for the sake of it and see what happens. And I do think that, I think COVID, I mean, I know for our business, COVID was freaking amazing, but the way in which we grew, I just had no control over it. I lost full control of the business and

then I was on a hamster wheel of keeping up. But I think the next wave is coming back to that solo partnership, which is really interesting. Absolutely. And again, I've seen so many creators have this journey and a lot of them also realize, a lot of them get to a point where, again, the money doesn't move the quality of their life. They can make less revenue with less expenses and be so much happier that that trade-off is just not worth it. It's not.

But I think sometimes, I know for me, I had to make the money to learn the lesson because I grew up with that scarcity mindset. I grew up, there was never enough. And so I was so motivated by money until I looked around and was like, wait, this isn't motivating. I would rather scale everything back than be on this treadmill of more. And again, just to caveat for everyone listening, we're talking about champion problems. Money was super motivating until a point. Like there's

absolutely a massive quality of life difference when it doesn't matter anymore. A narrative I heard which I found interesting is someone's like, the way I feel in my life is I've solved the money problem. And when that's gone, it's like the problem is solved. But solving the money problem was very, very meaningful and did make a big difference. But the issue I think is people think the money problem is bigger than it is. They think they need way more than they do to solve the money problem. Once you've solved it, that they keep getting incrementally greater returns when it doesn't really

happen. Yeah. I just think like you were saying with creators sharing numbers that aren't necessarily true. If that's your algorithm, you're going to be seeing every person online is make millions of dollars. And so you think, well, I should be making millions. And you'll realize, wait, I was really happy at this financial level. Everything was paid.

I was having really good savings. But it's just hard to know till you get there. But I don't think the number is as big as people think it is. I think it's different for everybody. But it's not what you think it is. At Teachable, we saw the numbers. I mean, the people at the very top end were doing well. But the real sort of like

demographic we focused on was six figures a year. If you made a hundred thousand dollars a year, that's a very good salary in most parts. And that's completely life-changing. It's life-changing. And if you can sustain that and get to a point where you have an amazing life outside of that, like what more do you want? Absolutely, there's a big difference also, right? We always told creators like, if you do the creator thing well, you make a living doing what you love, which is a luxury most people don't have.

So you try and maintain that versus building it to something you don't care about. Yeah, if you're too good at what you do, then it goes the other way. I love this conversation. I just wanna say I really admire the way that you live your life. I think it's really rare. But as you're speaking and talking about your philosophies and the way you think,

I just think there is no one better positioned to be doing what you do. And I really admire that. I want to let you know. I appreciate that. Sometimes I wonder myself. So it's good to hear that. You're like, why am I doing this again? Why am I doing this?

No, but I always, I joke. I'm like 80% of the time, I'm like, there's nothing else in the world I'd rather be doing. 20% of the time, I'm like, what was wrong with sitting on the beach? What was wrong with that? Do you still make sure you carve out now travel and vacation time?

I do, but I've become the kind of traveler I detest, which is lots of short trips. And again, like the true travel community shames you. They're like, I wouldn't go anywhere if it was not for three weeks. But it's like, I want to be at the office, yet I still want to travel. So I'm going to go to Ecuador over Thanksgiving.

And you know, like making those sorts of things. But in general, no, I feel like I live a very blessed life. Oh my God, the old traveler would hate the way I live my life. I have a daughter, I have a two year old. So if I can be somewhere for less than 24 hours, I will. I just got back from a speaking trip and I didn't see the outside of my hotel room. I'm like in and out.

A past version of me would have been, let me do this, let me do that. But priorities change. Absolutely. And again, building a company with a team where I care about every person I'm doing this with is profoundly more meaningful than going to the 67th country. But whenever I'm not running this company, I will also lean back into that life. Yeah, I love it.

Well, thank you for being here. Thanks for having me. Can you let everyone know where to go sign up for Cary, where to find you, all the things? Absolutely. We're at Cary.com, but we'll leave a special link under the episode. So they'll get something and yeah, thanks for having me. Amazing. Thank you. Wait, wait, wait, before you go, I would love to send you my seven

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