Building a Multimillion Dollar Business…By Yourself

I've learned to become much more gentle with myself over time. I think a year or 5 years ago or 7 years ago, I was like, ah, you didn't, you bad day, Jesse.

He'd look at, he'd look at, he'd look in the mirror and slap himself and then go back to—

A version of that. And I think over time I'm like, yeah, you know what? Like, and it's something I try to coach everyone I work with, especially the younger entrepreneurs. I'm like, hey, you know, you got a bunch done this week. Like, did the ball move forward? Did it go, did it not go backwards? You know, and I love the pushing a boulder up a hill analogy. I'm like, you know what, if you're pushing a boulder up a hill, if you keep it in the same place or get it forward a little bit, that's progress.

What's up, everyone? I'm Alex Lieberman.

And I'm Sofia Amoruso.

Yo, this is Jesse Pujji.

And this is The Crazy Ones. What is up, misfits? Welcome back to The Crazy Ones. I'm your host, Alex Lieberman, joined by my amazing co-hosts, Sophia Amoruso and Jesse Pujji. And this is our final episode of 2022. So here's today's rundown. First, we're talking about solopreneurship. That's right, running a business of one. We're going to talk about some actual examples of people who are printing millions of dollars a year and they are the only full-time employee on the business. And then my co-hosts are going to duke it out arguing the for case and the against case. of running a business of one. Then we're going to talk about time, how my co-hosts manage their time, how someone on Twitter I found is running a billion-dollar business and they have 3 things on their calendar in a given week, and the strategies that we have to spend our time as intentionally as possible. And finally, to round off the episode and to round off the year, we are going to have a quick brainstorm of how we think we can improve and innovate and grow this show in 2023. With that, we're also going to want to hear ideas from you. So whether it's now or after the episode, shoot us an email at thecrazyones@morningbrew.com and let us know how we can improve the show, ideas to make it better, or recommendations for how we can grow the thing. Now let's hop into it. So let's talk about solopreneurship. I think that this has become a bigger topic just in the world of more tools being accessible to people to start businesses, right? So like we've talked about the topics of AI writing code for you, we've talked about no-code, we've talked about tools like Substack that allow you to spin up a newsletter and charge for it. And so I think access to being a solopreneur is more open than ever before. But what are your guys' thoughts on basically being a business of one?

I would hate it.

I love it. Why?

Sophie and I are so different on this. I, you know, I don't know. I'm an extrovert.

I—

to me, one of the biggest parts of business is leadership and spending time with people and inspiring people. And my, you know, when I have my highest energy is like, you know, on a whiteboard with a group of people coming up with ideas. There's energy and excitement in the room. And like, I would probably rather make far less money and be doing that every day and just enjoying the energy associated with that than I would You know, sitting in this office. Like I tried to work from home for a minute during COVID and it just like didn't work for me. It was just too; it felt yeah too too much of the same. And so I I think it's cool. It's like by the way, I love the stories. There was a famous one when I was a consultant. There was this plugin that everyone at McKinsey and everywhere used. I forgot the name of it, but it was like a plugin into Excel that made your PowerPoint slides or into PowerPoint, and it was like apparently one guy making four. 40 million EBITDA a year or something, and you built this plugin that everybody used. But so it's cool. I'm like, that's cool.

But but you wouldn't want to do it yourself.

No.

Even if it was ten people or five people, I'd be fine. Like at that scale and size, I prefer. I like to build organizations though. I enjoy hiring people, thinking about how they interact, thinking about the values. Like that stuff is to me as as important as the business personally.

And I think I think yeah see. Just on the other side of the spectrum, like, is there a point at which the size of the business becomes so big that you don't enjoy it anymore?

I've never, you know, a few hundred people, like, I haven't run a business big enough. I think I've seen like people like Rick I've talked about at Red Ventures or Amazon. I see what they're doing and I'm like, that looks really cool. Like, yeah, they sort of have this platform and all these people and the culture. And so I, you know, I'm not sure. Yeah, it's something I've tossed back and forth, but I think if you do it well— one thing I realized, I don't know if you guys had this when you had a few hundred people, you know, at 100 people, you obviously don't have 100 people reporting to you. You have 5 to 7 people reporting to you. And someone pointed out to me at one point, they said, you know what's interesting, Jesse? Once you're at 100, you're never going to have more people reporting to you. It's not like the CEO of a 10,000-person company has more than 5 to 7 people reporting to him or her. And so I thought that was pretty cool. It's like, oh no, you always kind of have this team and you're always working with a team that you're leading and working on. Obviously there's more leadership as it gets bigger. So I don't know, I think, I think I would like to, you know, run something big and large and unique and have a unique culture around it personally.

That's Sophia. As, as the resident introvert, I feel like you're going to have a different point of view on this.

Yeah. I mean, I had a few hundred people and I'm a 0-to-1 founder. Took me way too long to realize that, and I probably should have sold Nasty Gal long, you know, before I raised venture capital because it was an incredibly profitable, successful business. It's only been in the last year that I've realized that I'm good at starting things. I'm amazing at starting brands. I can rally people and get them to care about and identify with what it is that I've created, and scaling the brand I really love, which I can do pretty nimbly. But actually operating the business is really challenging for me. And so over the last year, I mean, I pretty much have a business that is, it's me and I have an assistant and then I have one person in New York. And for the scale of the business, it may as well be a one-person business. I think there's a great opportunity out there. And Alex, you can talk about this in greater detail, for creators to spin out more than just, you know, You know, YouTube videos and TikTok videos. You can create an audience on those channels and through the press. Most of how I became someone who people follow wasn't because I was an influencer. I got a following because I was doing things mostly in the real world with the book and promoting it, and a lot of inbound out of you know not growing it through creating videos. Video wasn't even a thing on Instagram, and from that creators can. publish books, they can have Patreons, they can have memberships, they can have private things for their communities. They can, you know, host a, you know, Twitch— are they called channels?

Stream.

Stream events, books. There are so many opportunities to monetize as a business of one. I think what becomes challenging for any business of one is that when it's successful, you know, you spoke with Cody Sanchez. You know, I interviewed Ryan Holiday recently. All of these people, you know, Mr. Stoic, I'm sure started by himself. But once something gets big enough, you need people to help produce you because you're creating so much content. You know, the course creators Amy Porterfield and Jasmine Star, who have inspired me and I've learned so much from, they started, you know, an online course, which feels like maybe something that could be you know, passive income and really, you know, high margins. But over time, you know, you really want to scale that. It's challenging to do without a team.

Yeah, I feel like the, the most successful solopreneurs turn into entrepreneurs. Like, you're, you're like a solopreneur until you realize that something has enough opportunity to not be a solopreneur unless you've made the very intentional choice that you don't want something to get above a certain size because maybe it's just so profitable. that you hate actually everything that Jesse's talking about, like leadership, hiring, management, and growing your net worth by another comma or another zero isn't worth that work. And you just want to continue to print money with a lifestyle business. But I just want to double down.

Hold on. It's not a new concept, though. I mean, one thing we should like— many, many eons ago, I was a consulting kid and a hedge fund hired us to project the amount of domain names that would exist one day. It's a true story. And, you know, so like there's, you know, we looked at basically how many companies are there in the US. And so just guess how many, you know, there's, there's 4 categories. There's large corporations, there's like mid-market, there's SMB, and then there's what they call SOHO, which is small office, home office, basically single-person businesses.

The original SOHO.

How many of those do you— would you guess there are? This was, by the way, was of the last 2007, last group.

Number four.

Yeah, number four.

Sophia, you go first.

Fifteen years ago, without technology, without technology, are we including consultants?

It just means that in the in the IRS they say they're a one-person business.

Uh, five million.

It was eighteen. Oh go sorry shit. Eighteen million.

That that is so much higher than I was gonna guess.

No noise. I mean just it's not an it must be clear right? I mean this is the land of entrepreneurship. Like it's. By the way, that number is probably like 25 now with all these creators and everything. But it's not a new— it's not a new thing at all to be a single entrepreneur.

Yeah, I was— I agree with that. And I actually also think solopreneur for a lot of people is a misnomer. Like, it's not— I think there are very few, at least if you're talking about a digital solopreneur where it's like truly one person. Like, I think a lot of times it ends up turning into you have a VA in the Philippines or you have like an agency that's part-time helping with you. There's a guy and I sent you this, this article earlier, Pieter Levels, who I look at what he's done. And it's funny, like this is just the type of shit that gets me very excited.

He has—

he went through this project starting in 2014 of launch 12 businesses in 12 months, and a lot of it was to do rapid testing, learn how to test businesses to know if they're going to reach market fit or not, and also to like to not build for perfection and just put things out into the world because he said that was a big block for him. And I don't think he actually ended up creating 12 businesses. He created 7 and they're all over the map of what he created. He created Play My Inbox, which was a site that would pull— and because his friends would share music with each other over email, he would pull email recommend music recommendations over email, added it to like a single website view where you could play all the songs that friends had recommended to him. He had one— this is my favorite— gofuckingdoit.com, which was you set a goal for yourself, you set a date, and you set an amount of money you're wagering. And if you do not hit that goal, you pay the site for not hitting the goal. And so that was one. His actually his most successful one He has 2 really successful ones, Nomad List and Remote. Okay, so he is a digital nomad. He's been traveling all over the world. And so a lot of the things he's built have been around kind of the digital nomad, remote worker lifestyle. Remote. Okay. Is simply a job board for remote-only, remote-only roles. And Nomad List is amazing. It's organized by city, how good hundreds of cities in the world are for digital nomads. So it ranks on like the How is the community there? Weather, all these things. He does $2.7 million this year and his margin on his biggest business is 94% pretax. And the only employees he has, he has one customer support contractor part-time, Isabel. He has a moderator for a Slack group because he has a remote worker Slack group. And then he has a DevOps guy who's part-time and that's it. And so I, I think it's going to be interesting for him once like Nomad List or Remote OK gets big enough and he has the option to potentially scale those to $10 million. What does he choose to do? And that's why I think you only stay a solopreneur for so long. But I think it's amazing, this idea of just like the, the gap between idea to thing in the world just continues to get smaller and smaller. And I get so excited about that.

And I think, I think people consider entrepreneurs to be people that have businesses, right? We— that typically Business owner sounds like someone who opened a laundromat or, you know, often kind of like these family businesses. And today everyone is an entrepreneur. Today everybody's a brand, right? You're a brow artist, like you have an Instagram account and you like named your brow artist business and you're the only person doing it. Like you're a lawyer, you're a lawyer just for entrepreneurs and you've got a whole brand. Jesse, there's a woman who we've worked with who has that. You're an SEO expert, you're an agency, but it's just you. But you want to look bigger than you are. Like you're a dog walker, you're a nurse and you do Botox and filler. Like your Instagram is like you're literally a nurse, but your Instagram is like, look at how good the lip filler that I can do is.

Dr. Pimple Popper.

Also content creators, right? Freelance creatives, designers. They're an agency and they're not scaling up when they get a job like they're doing the whole thing, but they get a website that has a brand name and this is all very new. Also that businesses of one can market themselves digitally in ways where it was so much more fragmented and, you know, search was so much more challenging. And you can discover these people on Instagram. Instagram is incredible SEO, by the way, which a lot of people don't talk about. Yeah, for business. And if you optimize your bio on Instagram, someone's going to type in brow artist and they're going to find you and they may hire you.

There's a lot of themes that I think coming up that are interesting in what we're discussing. I think one is, especially for all the Misfits listening, like, man, there's just no type of entrepreneur. You know, it's like one of my— like, they come as they're in so many shapes and sizes, different expertise, different scale, different desires, you know? And I think that's the second thing, which is like, just decide what you want and go do it. You know, it's not a There's no right. I think one of the things early entrepreneurs, you know, a lot of people I coach and talk to like, am I doing it right? Is this the right way? And like, so hard to let go of that and say, no, no, there's no right. Just, I mean, if you're successful, do what you want. What do you want this to be? Right? What's your choice? What are you trying to make it? I think that's another one. And then I think the thing, Alex, you pointed out, and I kind of had a similar experience last year for myself. And, you know, Sophia, you said zero to one, getting that thing started is so powerful. Like, it was a good lesson for me after running a business for 10 years. Like, I don't know what these next 3 things will be worth. They potentially might be worth all more than Ampush after 2 years, you know, depending on how you look at them. And there is a lot of value in that, just getting that thing going, getting something going. And once I like— I started, it used to be very precious. Like, I think about how preciously I held Ampush and it was like my only company was the only— and I started 3 things and like people are like, well, it seems like you know how to do that. You're pretty good at it. Why don't— and it just really changed my perspective on things. But I think for anyone listening, again, Random job board, random— what, like, there's so much power in starting something, you know, operating it as a different, different sort of animal, which I think is part of the question here, which is, do you have to— can you sell it? Do you— can you solo entrepreneur it? Do you find other people to run it? Like, there's all these other questions, but there is a distinction between getting that thing going versus operating it.

Yeah. And I think the biggest thing is just realizing there is no right or wrong choice here. For the longest time, I was in this mental loop of there is— there was one definition of success in entrepreneurship, even though it sounds so ridiculous and irrational to say, like my subconscious guided me to make decisions based on this idea that I would not be a successful entrepreneur unless I ran my business forever. I stayed in the CEO role forever. I took my business public and anything short of that would not be a success. And I think Just to use the example of Pieter Levels again, like there's a lot of hard stuff about him being a solopreneur. Like he had posted or he had tweeted that he's started a bunch of business now and his hit rate's 5%. So like it takes a ton of at-bats and it's exhausting. This guy's coding all of his apps. But on the other side of it, it's like, I think this deserves airtime because I think if people just have this perception that Elon, this incredible guy who owns Twitter and Tesla and SpaceX, is the North Star for everyone. It's not realistic. And unfortunately, I think it'll disappoint people when they realize that their body is at odds with kind of that dream in their head.

Totally. By the way, the other— just as a random aside, this creator economy is going to become a huge business opportunity for people.

Yeah.

Like selling things to people who are creators.

Oh, 100%. Honestly, we should do an entire episode just on that. Like businesses to be built for people who are creators. I want to— last episode, Jesse, you had talked about that one of your goals for 2023 was to reduce your calendar by 20 to 25%. And you said you don't know how you're going to do it, but it's something that's important to you. I want to understand, how do you guys spend your time and like, what do you prioritize? How often are you thinking about shifting it? Because I've become obsessed with looking— it's been a recent trend on Twitter where like top CEOs will share screenshots of their calendars. And there's one guy who I want to get on to the show soon who he's like running a billion-dollar business and he had like 4 blocks on his calendar in a given week. And one of the hosts called bullshit on it. I'm not going to say who, but I'm interested in like how people think about their calendars and obsessed with seeing these screenshots. So how do you guys think about your time?

You go, Sophia.

Oh man, my time. Right now it feels really chaotic. I think I talked about on the last episode the kind of scope creep that Business Class has had, moving from what felt kind of like a solopreneur business to something that I'm having to restrategize right now. So right now it feels really out of control and there have been days this year That haven't. And they're— I think often it starts with grounding yourself in the morning. And I'm not the person who wakes up, you know, I'm not the person who wakes up at the crack of dawn, yawns and stretches like you see in the movie.

You're not the 4 AM cold plunge.

In my like perfect pajamas with like my hair done on Instagram, right? And makes their bed perfect.

I'm still asleep at 8 o'clock most days.

Makes them feel so good about their day and jumps in an ice bath while doing box breathing and using an ice roller on their face and then sits in silence for an hour drinking their tea and journaling and then meditating.

You don't at all seem annoyed by these people.

I think it's a scam. I think it's really dangerous to inspire people with a lifestyle or a morning that takes 3 hours. And unless you can go to bed at 9:00 PM, it's not possible for most of us. And it makes most of us feel bad. Half of us are inspired by it. And then the other half of us are like, how is that even possible? What am I doing wrong? How could I even have a productive day if that's not how I'm starting it? But I've done kind of glimpses of that in this year. The days that have really grounded me are going to yoga at 7:30 in the morning. I'm like out of bed at 6:45. I'm driving like—

So you just said you hate these people and now you're saying you do it.

It's literally just yoga. It's just yoga. If you can do like Realistically, if you can do one thing at the beginning of your day that grounds you and makes you feel accomplished, that's it. You do— I do yoga at 7:30 in the morning. I shower right afterward because there are showers there from 8:30 to 9. And then there's a Blue Bottle nearby and I go like jack up my system on like 2, like, you know, double shots of, you know, cappuccinos. And then I'm home by 10, or I take phone calls from Blue Bottle. And I mean, what I would like to do is stack my calls to more than like 2 hours a day, but I do 2 hours at a time and taking short breaks in between. And for the second half of this year, I have had days where I don't have calls and days where I do have calls. And that's been amazing, right? Fridays we record the podcast. I actually shower and put makeup on. So after this, I'm going to go make content and do some Instagram Reels and just take advantage of the fact that like I'm not wearing pajamas because I work from home. But not every day is like that.

Well, and just, just to ask a question around kind of like the more macro level, and then we'll dive in. How many hours a week do you think you're working?

You want me to look? Probably like 40. I mean, okay, thinking about it, it's like 100, but that's just anxiety.

So let's say it's 40. How much of that How much of those— that 40 do you think is business class? 6, 8, 6 hours.

It feels like so much. Well, that's on calls, probably like 5 hours of calls. And then there's so much inbound copy design, kind of like approvals of communications with students, writing my newsletter. That's kind of—

Yeah. So how much do you think all of that is?

Maybe like 10 hours, but it feels like 100 for some reason. And then—

Interesting.

I also talk to entrepreneurs and make investments. I create content. We record the podcast. You know, I do calls on the intro app and mentor people. I'm working with an ads team for Business Class and reviewing, you know, creative for that and updating copy. I still write pretty much all the copy because I cannot figure out how to delegate my voice. You know, I'm doing influencer stuff. I have a partnership with Notion, a partnership with SurveyMonkey, a partnership with PMI International, which is a project management organization. Like, that's all going back and forth with those.

So you have a lot of things.

It's a lot of context switching.

Yeah, I was gonna say, it seems like you have a ton of context switching. So, uh, first of all, how Are there any things that you do to your calendar to try to make context switching easier? Like, are you working on all of these things all days of the week? Are you blocking out certain times for the type of work that's most annoying in your day to get that done first? Like, do you do anything to help yourself with all this switching?

I put on my calendar, you know, after this I'm going to record content. If I— if something's due to a brand that I'm creating for a partnership like that's on the calendar, and if I have to create content for that, and it's due on Wednesday. Monday it's on my calendar, and my assistant's here, and he like is amazing, Tyler, and helps me kind of organize myself, prepare for that. We're looking at, you know, hashtag, you know, ad, all the things that you have to draft. There's such a level of detail for that stuff. But right now I would probably ask advice of you two on how I could better optimize that because as an ADD Entrepreneur with a lot going on. I think I could use some inspiration.

Jesse, what do you think?

Advice, or you want to hear what I do?

It's the same one and the same.

Yeah, maybe share what you do. Maybe.

I don't know. Everyone everyone has to figure their own. I think. I mean, the advice. Like I've learned to become much more gentle with myself over time. I think a year, five years ago, or seven years ago, I was like, ah, you didn't. You bad day, Jesse.

He'd look at.

He'd look at.

He'd look in the mirror and slap himself. And then go back to a version of that.

And I think over time I'm like, yeah, you know what? Like, and it's something I try to coach everyone I work with, especially the younger entrepreneurs. I'm like, hey, you know, you got a bunch done this week. Like, did the ball move forward? Did it go— did it not go backwards? You know? And I love the pushing a boulder up a hill analogy. I'm like, you know what? If you're pushing a boulder up a hill, if you keep it in the same place or get it forward a little bit, that's progress. And like, as long as it doesn't go back, you're good. And so I think in general, for anyone kind of attacking these sorts of things, I think you got to be real gentle and sort of— it doesn't mean you want to get better. You can learn things. But to me, that's like the— I think that keeps people frozen the most because they just, they freak out, you know, they're just so tough on themselves about it. And I was like that and still am in some ways.

But and so how do you approach, given that you're, you know, you have your company Ampush that you're not actively involved with, but it's your, you know, it's your baby. You have your 3 businesses within GatewayX. Like, how are you thinking about strategy around time?

Yeah.

Yeah.

You know, I don't want to post one of those calendar things because I can't brag about mine. I will say, you know, it's interesting.

I—

my calendar is very busy even beyond the work hour, and I'll walk through it in a second. I, you know, I'm a little torn because on the one hand, I get a lot done and I don't just mean, again, work stuff. Like, I play tennis 3 times a week. I like hang out. I put my kids to bed 4 or 5 nights a week. Like, I do a lot. And I'm not generally an organized person, but like, that's one area where people are always like, damn, Jesse, like, because people know me in life and I miss flights and all this stuff. They're like, damn, your calendar.

Wow.

You— I miss 10% of my flights as a life rule. You're spending too much time in airports if you don't.

I feel so much better about myself.

Yeah, I would not have guessed that. But sorry, continue.

So, but anyways, you know, so I am torn, but at the same time, sometimes it feels overly scheduled. So yeah, let me give you my week, I'd say. So a couple of different things I know you've been asking, Alex. So one is I've tried now on Mondays and Fridays I do other business interests and like for Kahani in particular, I'll do the kickoff for the week and the major, you know, what's the meeting, you know, what's the plan for the week or the sprint? What are the various teams doing in sales, marketing? What do we have to get done? So basically, and then in addition, I'll meet with the other leaders of the other businesses on Mondays and Fridays only. So Tuesdays and Thursdays are Kahani days. They're blocked in my calendar. There has to be a very good reason for me to come off that, which is something that, you know, post-raising money and kind of focusing on being the CEO, there is something that I did differently. It doesn't mean I won't spend time on those things, but in general, it's a good forcing function to avoid that context switching, of which I have a lot. My general workday, I'd say, is like, well, it's a little different. So Monday, Wednesday, Friday, it's like 8:30 to 6 or 6:30. I'm home by 6:30. I do dinner and I'm like, I'm on kid night duty, you know, Monday and Wednesdays and Fridays and Sundays. Tuesday, Thursdays are my late days. So I usually work like 8:30 to 7:30 or 8. I don't— I usually don't see my kids. Sometimes I'll just sneak to say goodnight to them. I play tennis on Tuesdays and Thursday evenings. Like Sophia called me yesterday. I was on the courts. And so those are my tennis days. I usually do try to work out on Wednesdays. Also, I have date nights Wednesday, Saturday with my wife. that are just kind of like, again, those are— we don't change them very often unless we have to. Friday night's pizza night with the kids.

And I mean, you seem very routinized.

Very, very routinized. Yeah, big time. And I think when you have that many stakeholders, like, again, not just in the business side, but on the people side. And then in terms of how I spend my business time, I think I've tweeted and stuff about this. You know, one thing I learned from Rick at Red Ventures, he doesn't like standing meetings. And I try my best to actually I'm not like that dude who put 2 hours and like, I have nothing like— but in general, like, I try to avoid standing meetings. And the reason is, is because what's important this week or for the next week or 2 is going to be very different than what's important in the following 2 weeks. And I like to change and shift my hour, like where I spend my time depending on where I need to be, you know, what needs to be getting done in that time. And I think being that like a mistake I see a lot of founders make is— and I made this early on— was my calendar inside of those blocks being too routinized. I have to take this at this time, then we have to meet on this. And that's when you start creating meetings that people show up just to present something that they don't actually have anything. Instead going, hey, let's, let's grab time on this thing. Looks really important. We should talk about this right now. And this other thing, let's push that out. So I do try to be very dynamic. So every Sunday I spend an hour or 2 kind of planning my week, trying to figure out what I should spend time on, where I should go deep, where I should spend time. I'd say the biggest thing I'm trying to work on for next year I don't do a lot of work. Like, I'm pretty scheduled from 9 to 6 or 9, like, meaning I'm taking meetings with people almost constantly internally and externally. It hasn't— doesn't leave room to do any work like it. And actually things like I can write or things that— and so I'm trying to get better at actually with my assistant blocking off time.

I was just about to ask about that. Like, do you have time for any time for deep work? Like just even thinking high level about your 3 businesses?

Week— I mean, weekends I'll do it like Sundays. I usually work for about 5 or 6 hours. I'll get some stuff done. Then I'll come back online at night, like after everyone's asleep in my house, usually for an hour or 2. That's usually for email, but sometimes it'll be I want to sit down and write something out. I want you guys to know I'm a pretty off-the-cuff thinker, so a lot of my thinking happens and it'll just come through me like it'll be something that's like sitting in the back of my brain.

Yeah.

And then I'm like, oh my God, I got to write this down. There's something really important happening here.

And yeah, just like Jimmy Neutron.

But I want to get better at like blocking off 10 hours a week of work of things I want to actually do or try to get done. So that's, that's one of the big improvements.

One last question for you is not that they've said this, but what would you say if a Kahani investor was like, dude, you're, you're the CEO of this business and you have just 2 days a week focused on Kahani?

3.

3. I thought it was Tuesday, Thursday.

Tuesday, Wednesday, Thursday.

Okay. Got it.

Got it. Yeah. So you have 3 days, a half day on Monday.

Yeah. Oh, so, so, so it's, I guess, the majority of your week.

Yeah, it's definitely the majority. I mean, look, you got to make these— you got to get clear with people upfront on what's going on and what's like in my documents or all these other businesses. They're aware of my roles there. They're not— they're not naive that like this is who— and it's part of what it's, you know, you take the good with the whatever, with the opposite, like They know the benefits of being involved and they know the costs. And so, yeah, I think, I think they need to pay attention to the ARR and how I'm growing the business. And if I'm doing a shitty job, they should fire me. And if I'm doing a great job, they should, you know, be really happy.

Yeah, that makes total sense.

I don't have any doubts that Jesse has time to think or doesn't need time to think. Just knowing how little Jesse has to prep for this podcast and the kind of wisdom that just Flows out of his mouth. I, I have a feeling it happens. Yeah. Like his ad hoc—

He's just, he's just a walking epiphany.

I—

well, in the sessions though, of time, and it's like, I'll— you can make time to think in those meetings. Hey guys, what's a big challenge we're having? What's it like? To me, getting really present during, during a meeting itself is like a really important piece of this, which is we actually like, we've started doing it as a rule now. We breathe for 30 seconds before the meeting. We do a box breath to make fun of the earlier thing. We start meetings with box breathing and then we go, okay, what do we want to do here? What are we trying to get accomplished? We don't do it perfectly, but it's really valuable to do that in the session itself.

I love that. I actually know a friend of mine. Part of her consulting business is helping like Fortune 500 companies, like coaching them up in more present meetings by doing the exercises you just talked about before every single meeting. And I remember I asked her, I was like, How do people— if you're going into like Apollo or KKR and you're about to tell this MD, hey, I want you to breathe in for 3 seconds, hold it for 3 seconds, out for 3 seconds, hold it for 3 seconds. Like, I would love to be a fly on the wall seeing that MD at KKR respond to you wanting them to do that breath. But like, it is so important.

But they're still human. And every human knows that when they're present and they're there, they can be much more capable, powerful, thoughtful.

Totally.

And when they're not, they can't be. And I think the— by the way, the best thing about box breathing is it's the easiest thing to convince someone of doing because within 30 seconds they do it and they go, wow, this is better. It's like the easiest thing to convince someone of because it's such an immediate gratification when you breathe.

Totally. I just want to share a few parts of kind of how I spend my time because it's changed so much over the last few years. And I, I'm very ADD, like my brain is all over the place. And so I'm constantly thinking about how do I, how do I wrangle like the madman, but also respect kind of the value of my brain. And so just a few things that I do. I don't start anything before 9 a.m. because if I don't get my morning routine in, it throws off my entire day and just my morning routine very simply. Is it's like 7:15, wake up, feed my dog, take my dog out for a walk with my fiancée, come back in, have a coffee, and then go and do a workout. And then I start my day after that. And just any day I miss that, I just don't feel as good. Like it doesn't ever feel as good for me to do a midday workout for whatever reason. Then Similar to Sophia, I try to lump as much content creation together as I can. Said differently, like I try to lump together similar skills, so I try to do a similar type of action around the same time. So like 60 Second Startup, my social series, I'll do a dozen of those at once and do try to do Imposters and TCO on the same day. So I do those things together and then I try to just batch everything. I try to get to bed before 11:00. Because if I don't do that, it throws off my entire next day because I really try to get 7 to 8 hours if I can. People—

another thing I'm working on is sleeping early. I am not an early sleeper.

Yeah, it just— what, what honestly ends up happening is I end up sleeping later because I want it. I need to get sleep and then I don't do my morning workout. Like, that's the trickle-down effect. I've found that I'm way more ADD in the afternoon, like for whatever reason. when 2 or 3 o'clock hits, I just get less productive. And so I really try to have pre-2 o'clock be my more productive hours. And I would say like the hardest transition that I found when I switched from working at Morgan Stanley to going full time on Morning Brew, and then the transition I made from running the day-to-day of Morning Brew to being the chairman, is I went from every minute of my day was dictated for me to every minute of my day was not dictated for me. So like at Morgan Stanley, It was 6:30 to 7:30 p.m. I am staring at a screen doing trades for 13 hours. I went in, went full time on Morning Brew, and there was all of the possible things to do on the business, but there was literally zero in my calendar. And that is an incredibly daunting thing. That same exact thing happened when I went from CEO to chairman. And so it's something I'm still trying to work through. So those are some of the things I do to just manage my schedule.

What, what gives you the most energy and what is the least energizing?

I would say the most energizing things for me are build 0 to 1, like building things I'm really excited about. Like I've sent you guys this backyard game I'm playing and like, or that I'm making and like the process of talking to the industrial designer about the design of the game and getting videos from the manufacturer in China throwing the plungers at the game. Like, to me, that energizes me. Like, you guys know, I recently built this free startup database where I just curated my favorite startup resources on the internet, like going through the process of figuring out what no-code tools to use, how to connect Zapier to like It just, it's just like the, the real life, like hopefully money-making versions of like Legos. Like that's the part I enjoy doing and I really enjoy creating content. So going back to last episode, as I think about next year, it's just like I want more of that in my life. Okay, let's, let's move on to the final topic. And the final topic today is It's a little bit of a meta one. I've been spending a lot of time recently thinking about how can we just keep leveling up the show? How can we go from, you know, right now we're, let's call it, getting 20,000 downloads an episode on the show to, you know, how do we get to 50,000 downloads as soon as possible? And on the video, how do we grow our YouTube channel faster? So beyond just creating better content, always like to me as a media mind, like that is always going to be number one. Create better content and good things happen. But how do you guys think about what we can do to improve the show in the new year? Have it grow faster? Like, no bad ideas. What do you guys think?

I think we do longer episodes. Longer, longer and more free.

Look.

Well, okay, let me combine it. Longer and more free. Like more just like a little bit more riffing, a little bit less just sort of like Us, the 3 of us making little speeches.

Yeah. I will say, Jesse, you are very consistent in your feedback. You, you have been very consistent since day one about kind of what you envisioned for this, which isn't a bad thing, but it's just an observation. I'm—

I like, you know, today and on our last show, we're talking about a little bit more evergreen topics like how to set goals, you know, side hustles and how that is different from, you know, starting a business or What it's like to be you know a business of one, and who is that right for? I think sometimes we get into really complex stuff that for the average listener may be harder to grasp, where we may be throwing in acronyms or talking about arbitrage businesses, which EBITDA, EBITDA, which is okay. We should talk about we should talk about business finance, but I think throwing out terms without first demystifying them for the person in the room. who may not know, keeping a headset on for that person and listening for them is really important and just making sure that we're answering their questions before they have to ask them. And I think we could— I think having guests once in a while, which we have, is also just a fun way to grow it.

Totally.

Because we use their platform, but also a way to get a different perspective on some of the things that we've even already talked about. Because everybody's going to have a different point of view.

If you guys could have one guest, who would it be? Who comes to mind?

Jeff Bezos. Are we— what are we— are we gunning for big here?

Yeah. Yeah. Anyone. Anyone. So, okay. Bezos. Sophia, who would you pick?

I think like Marc Andreessen or like a top VC talking about what great entrepreneurs look like. Someone who's kind of seen it all and seen who wins and who loses and how they think about entrepreneurs from the 10,000-foot perspective of someone who literally sees everything out there and how they pick what they think are going to be winners.

I think it'd be fun to play with different formats, by the way, like me and Sophia only, no Alex, or Alex and Sophia, you know, just Sophia, just Jesse. It would be fun to just play around with that.

Totally. By the way, that's one of the things that I had down. Which is, I think, testing formats. So like bring back the solo Founders Journal style where it's basically like a 10-minute journal entry by us as like interesting shit is happening in our businesses or test out a differentiated interview format, whatever that looks like, or shorter episodes around a specific evergreen topic. Like for example, if we did something around, I don't know, like end of year reviews or if we did something around wartime leadership. Like, I've been thinking to myself, if we do a 50-minute episode and that 15-minute piece is in the middle, it may not be the most efficient thing for the person who's looking for like wartime leadership lessons. They would just want to find that single episode. So yeah, I think playing around with formats for sure makes sense. Or I don't know, I would love to like even have like an actual recording of you guys running a meeting with your teams so people could actually be like, make an episode, be a fly on the wall listening to how Jesse runs a meeting with his teams.

Yeah, I think each of us, you know, we could divide and conquer in some ways where, Alex, if you want to talk about something more news-oriented or topical or maybe complex that I, you know, may have a harder time contributing to because I have a different zone of genius, like I'm happy to have a conversation on my own about that or interview somebody. You know, I interviewed people for 5 years on Girlboss Radio. So tag teaming, I mean, also it's like, yeah, it's like I can do that on a Friday and you can do it 3 weeks later, or you can do a mini episode or lesson.

And by the way, that's how much— how we create more surface area, right? Like we have 1 episode a week on the feed right now. Like, what could it look like to get to 3, but not with like 3 times the amount of effort? And I think that's, that's possible.

I'm game. I'm game.

I love it. Yeah. You guys took all the good ideas. I think that's awesome. Well, the reason this was a meta discussion is because I want to hear from the audience now. I want to hear from the misfits. So for those listening or watching this episode of The Crazy Ones, we want to hear from you. What formats do you want us to try in 2023? How do you think the show could be better? Or what ideas are there for growing the show that maybe we haven't thought of? Shoot us an email at thecrazyones@morningbrew.com. And if you'd be so incredibly kind to give us the gift of subscribership. I wish I was. I wish I had a better word for that.

Sharing it. Share it if it's valuable for you.

Yeah. No, no. If, if you guys would be so kind to give us the gift of sharing, subscribing, rating and reviewing. That is how more people can listen to this show. That is how more people can be more equipped to build businesses. And so we'd be incredibly grateful for it. Thanks everyone for listening and we'll see you in the new year.

Thanks everybody.