We Give Away 7 Profitable Side Hustle Ideas for 2023

The thing I've underappreciated the most in my life, and I find most entrepreneurs or side hustlers, is how much learning you do from point A to point B and that you're a different— I mean, it's a stepping stone and you're a different person. If you got a business that made $100,000 on the side, sure, that money is great. You, the learning and what you see from it will completely change your brain. And I think that's like the best part of anything like this.

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

And I'm Sophia Amoruso.

Yo, this is Jesse Pujji.

And this is The Crazy Ones. What's up, misfits? Welcome to another episode of The Crazy Ones. I'm your host, Alex Lieberman. And as always, I am joined by my co-hosts, Jesse Pujji and Sophia Amoruso. And we are pumped to bring you another episode of The Crazy Ones as we start to wind down 2022. With 2023 breathing down our necks, we've been thinking a lot about how to bring you the best possible content to start the new year strong. And so here's today's rundown. First, we're going to talk about side hustles. We're going to talk about ideas for how to make 6 figures in 2023, as well as examples that we already see being put into play by other individuals. Then we're going to dig into how each of us practices self-reflection, whether it's personal self-reflection, reflecting on our businesses and things that we keep in mind to have a strong new year. And finally, we're back with Startup AMA and It's a pretty fun question that we're going to be answering. Basically, someone I know dropped a shitload of money on buying a website and we riff about if we would do the same thing. So let's hop into this thing. Side hustles. So I was on Hacker News, which I would say it's probably my third favorite tech blog, tech site after TechCrunch and Product Hunt. And there was a popular thread of people talking about side hustle ideas they have for 2023. And actually, Nathan Barry, the founder of ConvertKit, wrote down how ConvertKit had started as a side hustle that now obviously is a super profitable, probably $300 million business. And so it just got the wheels turning around us having a brainstorm together around what we would do if we had to make 6 figures next year without working full time on an idea. So who wants to kick it off?

Hmm. Can I start with a confession?

Yeah.

I really suck at side hustles. Like, I've tried many times to do things. Like when I used to work, when I was in college and even my first, my few jobs, I tried to get something going and I just, they never went anywhere.

I mean, isn't GatewayX kind of a suite of side hustles?

Well, I mean, it's a little, yeah, it's a little different now, but like when it was just me and I had a job full time, And maybe I'm just saying that because, like, if you're listening and it's like there— I think there's types of people, like, I'm one of those people who if my focus and energy is not going to something, like, I can kind of only focus on, you know, on one big thing at a time, especially back in the day when I had a full-time job because they're pretty demanding and stuff. But I, I tried so many times to get things going on the side in college and then in my early jobs and I just sucked at it. They never—

Well, I guess what do you define a side hustle as then? Because To Sophia's point, wasn't you know Kahani a side hustle before it became a business that you now have raised for? Like wasn't you know Growth Assistant a side hustle before you put in place a CEO? Like what would you refer to those as?

No, I think those were highly intentional business. I mean, I use my like I probably used full time for six months of getting Growth Assistant off the ground. Like I was I was this is what I'm doing. I wake up every morning. It's what I obsessed about. It's what I. You know, what I thought about every second I could. And for whatever reason, that's how I'm wired. I like every time I tried to go like, okay, this is what I'm focused on. And then this little, little thing on the side, it just never worked for me. But by the way, for what it's worth, I think that's a very Jesse thing. It's not a— I think there's lots of friends and people I've interviewed and other things who they are great at getting something going on the side. And I think if you can make that work, I think it's the best way to do it because it's like the least risky by far. Yeah.

Yeah. And out of curiosity, my guess is you'll say like they're just like real businesses that you're just not active in the day to day now. But like the businesses within GatewayX, right? You have 3 of them. You have Unbloat, you have Growth Assistant, you have Kahani. What do you consider the 2 that you're not running the day to day of now? Businesses that you've put in and operate?

They have management. I mean, they have, they have, they have several people who it's their full-time job. It's what they obsess over. So I think like, yeah, typically a side hustle is something as an individual you're doing on the side. I started watching Sophia's TV show this week, Girlboss.

Is that your side hustle?

Well, no, I just like— it got me excited when the first, like the first, the first episode she finds some jacket and she like sells it on eBay on the side while she'd gotten fired. Whoever the character.

Yeah, there was no side. It was the front, but it was like—

She got really excited when she sold her eBay jacket and it was so weird. I was like, there was like a, like a little scene with a dude and they were like, I was like, this is weird. She's my friend. I don't know why I'm watching.

The whole thing is weird. It's just like how—

not to get too off topic, but how accurate is that show to your life? I haven't watched it.

Like 50/50. You know, the overall story, it's like a girl named Sophia working in the lobby of an art school. I guess I was working when I got the idea, but, you know, buying vintage, being like, oh my gosh, I can use this tool that exists, the first real marketplace that became popular. And there's this whole framework for me to start an online store. that otherwise, like, I would never have figured out or invented. I would never have even opened a brick-and-mortar store. Like, where else other than Craigslist or a flea market could I have flipped clothing? But I never went to Coachella. I never had that best friend. My mom was not—

Don't tell me, dude. I'm watching it now.

My mom wasn't like a loser alcoholic. I don't know. They made things a little bit more dramatic. I mean, of course they were dramatic, but they made up some different drama and I thought it was cute. And I thought it was—

But it was— to come back on topic, it was a side hustle for you. I mean, you had some kind of crappy hourly job and you started flipping clothes. It was.

But it's interesting. It almost feels like, Jesse, like your view— I don't know if this is exactly true, but you're like calling something a side hustle if it's not as intentional about it becoming a business. Because I would say, like, I'm not judging it.

I'm just saying every time I tried— when I worked at One Wall Street, I tried to get this like media site going on the side. Do you remember the whole F My Life? Like, yeah, website. It was like an early thing. And then it was like we bought all these domains, like my life is finance and my life is Black, my life is Jewish. And it was supposed to be like basically offshoots of that to get people to post funny puns about their little subsegment. Yeah, it never went anywhere. I still own the domains. It never went anywhere. Like, it was just I couldn't get myself to focus on it.

It's, it's nice foreshadowing for us talking about your domain story in, in like 30 minutes. But Sophia, what's your view on side hustles? Like, are— do side hustles work for you? Do you have the same definition as Jesse?

Everything is— not everything, but a lot of what I start is not as— it could be more strategic. Business Class was actually a really strategic effort to build a side hustle, but it has kind of, after a year and a half, become a bit of a front hustle, which I'm trying to figure out how to change. And even though we only launch it on a cohort basis, Twice a year, the amount of push and prep that that takes and promotion and ad creation and ad strategy creation is a lot. And so I'm putting business class on evergreen, which I haven't talked about or announced, but that'll happen at the beginning of next year, which you know I'm going from wow I have the summers off I only launch this twice a year to okay it's on all the time but it's on drip right someone can join it's a rolling enrollment period it's a little, maybe more passive, but we have to keep onboarding people and keeping them happy in the first several weeks as they join.

And out of curiosity, what is a bit of a front hustle? And what, what assumptions did you get wrong that led it to being far more of like a full-time job slash business than you thought it was going to be when you started it?

I mean, it wasn't for the first year and a half. I took like half of last year off. I bought a house in Kauai. It did so well. I took the summer off, right? I was on an island 5 months out of the year. I think it has to do with the world opening up. It has to do with the economy. It has to do with the shift in the business. Online courses, there was a big boon. Everybody was at home, and that's really changed. So I don't know if it's the amount of work, it's the amount of effort to re-strategize the business. and to make up for lost revenue this year, unfortunately.

Yeah.

And so in terms of the side hustle, there are still ways for me to not just try to bring in new students, but also provide low-ticket offers or workshops to people that are $150. And, you know, eventually they're excited to learn from me or someone else and they become part of the business class world and they, you know, then upgrade to business class, which is huge investment. $2,000. And also there are opportunities. I mean, again, it could feel like a side hustle not to build like a YPO type thing, but yes, small groups that pay more than the cost of business class to join. And I hire like a few coaches to mentor them, but that doesn't necessarily have to be something where I'm building, you know, what Sam Parr is trying to build in like a $200 million business. So And he's talked about that. It's not super under the radar anymore. He—

well, now it isn't.

Alex, let's, let's get into the brainstorm. What are your ideas?

Yeah. So I jotted, I jotted down 5 ideas that I'll run through quickly from, I would say, normal to ridiculous. So the first idea that I jotted down was, and I've been thinking about this for a little while, and I would say the, the way that I generally think of like ideas or like moving forward with ideas is I know that I have like a constant abundance of ideas. And so I don't try to hop on an idea the first day or week that I have it. I see like, does it stay around for 6 months and longer? And so this is an idea which is specific to my neighborhood, but I think can grow. And the idea is starting a mobile dog grooming service. As a side hustle in Hoboken. So the notion here is like Hoboken is the 4th highest density city in the US, which I didn't realize. The demographic is what I like to call like Dog Central and the Stroller Battalion. And every dog owner that I've talked to does not have loyalty for a dog grooming place in town. And so the idea I was going— I literally went through the costs of all this stuff. I The cost of getting a dog grooming trailer is $63,000 a year. And I just start making assumptions like if we get 5 dogs a day just on the weekends or 5 dogs a day on the weekdays and we charge them $60 and the cost of labor, the groomers, $22-something an hour, the payback period could be anything from 6 months to 3 years. 3 years if like We only do it on the weekends and we can't charge nearly as much for the dog. But I just think there's such an opportunity here because dog parents will do anything for their dogs. People don't have affinity for groomers. Most groomers are mom-and-pop shops. There's no brand for dog grooming. And I also think there's an amazing business to actually just exclusively not even do cuts, just do showers and dries. because people hate having to go in their shower and wash their dog. And I think people would do it once every 2 weeks. In your shower? Yeah, yeah, that, that's what we do. We bring Rambo into our shower.

You have a big dog. You have a bigger dog.

Yeah, he's a 55-pound dog. I have like hamsters. And he, he hates it. There's a whole blow-drying process. And also, like, you don't need skilled labor if you just do washes and blow-dries. So the thought is start this in Hoboken, and then the real idea is Then what if we create a YouTube channel around this? I, once it's operational, hire in a young, first-time, hungry entrepreneur to run this business and document the entire process. And if there's appetite for it, ultimately, like at the end of the day, if you turn every company into a media company, all of a sudden monetization can grow into also like ad dollars and not just the business.

So that's one thing. Or franchise. Create a franchise.

Exactly.

But this doesn't sound like a side hustle. This sounds like a real business idea.

Sounds like a business.

What sides it? What sideifies it?

Like 3 years payback period.

That's so, so, so I guess, I guess I define side hustle a little bit differently on that one. My view is like, what if— what is something that I can spend a good amount of time on in the early days and then I only have to spend like 5 hours a week after that? And to me, that once it gets to 5 hours a week, It's side for me. It's not the full thing. It's the side thing. I'll give you one other example that I think is more of a side thing. Actually, 2. One is— this is the ridiculous one— getting my honeymoon sponsored. I— Carly and I are planning our honeymoon. I'm not actually going to do this, but there's part of my brain that thought about this. I didn't realize, like, how much goes into the honeymoon process, how big of an investment it is. I've thought to myself, with somewhat of an audience, would airlines, resorts pay for amplification of the experiences? Not in a way that dilutes my honeymoon experience because I'm going to be photographing and videoing everything anyway, just after the fact, putting the content into the world. So, so that I would assume—

I like this. This is also not a side hustle idea. This sounds like a genius affiliate, like platform. Get people to film.

Brand deals, you know, with big sponsors. The salespeople that I talked to, we were like, "We want to do a conference. We want to do this." And they're always like, "They're not going to pay for your wedding. You can't get a brand to pay for your wedding." And that's literally what you're trying to do, which is why there's got to be a business.

Hold on. There's got to be a business of calling the like the points guy and saying, "Not I mean you were one person, Alex, but like hundreds of people filming and making their content on their trips," and then.

So this, this leads into the, like the, I would say the bigger idea, which is actually a business idea. And I just, I don't think I would enjoy it enough or long enough to do it of creating like the true all-encompassing consumer affiliate network. So how do you become an affiliate for everything in your life? Life. So like one of the other side hustles I had is like, could I make 6 figures a year from referring my financial advisor, my tax attorney, My apartment building, my trainer, my nutritionist. Like, if I get a few clients, can I get to 6 figures just with those high-dollar price services?

My, my, my ideas— I think those are all real. With respect, Alex, I think those are all real business ideas.

Okay. What's your idea?

I think that part of the side hustle thing is you have to leverage some of the best parts of scalable businesses, right? And so, so scale— like, one thing we're all in to some degree, the media business or something that I can create once or software I can create it once and then it can live on without me versus like the dog grooming thing is so services heavy, it just feels like it's going to be a huge pain in the ass. So my— I had 2. None of them are amazing, but like I think with the proliferation of no-code tools, I think there's— I mean, there's probably 6 different side hustles there. One is obviously just helping people learn how to use them and make them easier. I think the most interesting one though is, and some people have already done this on Twitter, is like, oh, Notion templates and I'm going to charge you $10. But I actually think You could have that for Airtable, you could have it for all the various tools. So I want to accomplish X and for $10 to $20, you know, accomplish Y. Like I stumbled upon these businesses with my kids coloring, coloring, you know, the coloring books. Yeah, you can, you can Google anything and there's these— they must be side hustles. You can download like a coloring of Mickey Mouse or Wizard of Oz or something random and you pay like a buck every time.

So just like outlines of the thing that you can download to color.

So my kids are bored and I'm like, they want to color something. Okay, here, here you guys go. Princess Diaries. I paid $1. They're good, they're high quality. But anyway, the same thing for essentially all the no-code stuff, which I think is just like you can make one a week or 2 a week and then sell them, you know, basically show up on Google. And that's one version of it.

This is what— this is what Thomas Frank does. Thomas Frank, the YouTuber, he shifted from having this like massive productivity channel that has 2 million subscribers to— he's going to be like— he was like, I'm going to niche myself down to just be the Notion guy. And so he creates videos on YouTube has a channel now for Notion, has 130,000 subscribers, and he's doing, I believe, something like $150,000 a month in Notion template sales, 90-something percent margin.

And whatever you do in the world, if you're sitting there, you're an accountant or you're a pet person or whatever it is, everybody needs a template for something in their life that's important that you probably understand and have that unfair advantage. That's how I would think about it. And then the other idea I had— so we bought a business in 2018 called My Subscription Addiction. And the story was the founder, Liz, who's a wonderful person and who bought it.

Was it— was it— got it.

Yeah. Ampush bought it. And her story was in 2012, she got obsessed with Birchbox and all these subscriptions. She just started writing about them online and, you know, just purely passion. I'm going to write about this category. I love this. I'm going to order them and review them. And like everything like that, it started to snowball. Other people who loved them started following her. to the point where she had a multimillion-dollar EBITDA business, but it started as a side hustle. And so I think like pick a category again that you, that you love, that you know of, and just start writing about it or some way contribute to content. I think you could totally do it on the side, but then it gets the scale of media over time.

I think also what people don't realize is that not everything has to last forever. And just because you spin something up and spin something down and it works for a while, isn't necessarily failure when it's your intention to say, you know what, and I'm not going to do this with business class. But business class was amazing for the first year and a half. And had I invested whatever I did, $400,000 into the stock market and it threw off millions of dollars in a year and a half, that would have been an amazing investment. And that's something that you can sunset over time. You know, Andrew Wilkinson was telling me that he bought a business that was totally became irrelevant because of Figma, but had a community. He doubled the prices and people continued to use it, but eventually it kind of phased out, but he bought it for nothing and he was able to extract value from it while it was on its way out. So side hustles don't even have to necessarily be things that you're committed to for a long time.

And I, and I think to riff on that for a second, I think the, the thing I've underappreciated the most in my life, and I find most entrepreneurs or side hustlers, is how much learning you do from point A to point B and that you're a different— I mean, it's a stepping stone and you're a different person. If you got a business that made $100,000 on the side, sure, that money is great. You— the learning and what you see from it will completely change your brain. And I think that's like the best part of anything.

And that's why sometimes I think the best businesses really do start as side hustles that you just like genuinely wanted to learn about something like the Nathan Barry story that I alluded to was ConvertKit started as he was building iOS apps. He wanted to blog the process of him building iOS apps. He would send out these updates through Mailchimp, and as he was doing it, he realized the best way to grow this list wasn't like paid marketing or social. It was people in his list referring other people. But he was basically like, there were none of these the segmentation things or like marketing tools in Mailchimp to do this. So he's like, I ended up just building the system that I had like scraped together when I was doing my blog on Mailchimp. And obviously when he started this, he would have never had an idea he was going to build a SaaS product for every creator and blogger.

So and even Morning Brew, I mean, Morning Brew, you guys essentially started that as a side hustle. And by the way, I think email newsletters is another one.

Oh yeah.

That like I think there's— by the way, it's so funny, there's so many email newsletters like they're Freaking annoying, and like even I have mine. I'm like, does anyone like? But I think what's missing is actually a diversity. Like your whole point about pet owners, you know, every breed should have its own newsletter because you know. So there's probably all these little things that the more niche you get, and you go, I'm gonna just write every week about. I'm not a dog person.

You guys know other side hustle coming soon. I haven't told you about that that one yet.

What Red Ventures did with websites, someone can do with newsletters is just something really neat.

Before we. Sophia, before we push forward, I just want you to share. You were telling me about this other idea that I think is like so interesting in this remote environment.

Yeah.

Talk about the idea you share with me.

I've thought about it and I've seen like kind of rinky-dink creators doing stuff like this with like their communities. And I've also heard that people with ADD doing coworking or being kind of held accountable in some way live just— and that works for me is like if I'm with someone literally in the room energetically, I'm so much more able to focus even if we're not talking than I am if I'm sitting by myself. And I discovered this thing called flown.com. And it's wild that they raise money because they're basically just creating Zoom groups of people who can join for a period of the day. And so they have different sessions all throughout the day. They have deep dives. I think they have like 5 a day, and that's 2 hours of silent work. And they, you You state your intentions at the beginning. You do like a group—

It's so absurd. It's a business.

Stretch in the middle. I love it.

I love it.

But you're just sitting in silence and there's other people's faces, but you're like, okay, this is what I'm doing. It's almost like being on the phone or, you know, on a podcast. It's like the singular thing. You're not focusing on the group, but you're committed to focus because in the same way you go to a yoga class, people are there doing yoga and you're, you know, look kind of bad if you leave, even if you want to. You know, so they have power hours, which are an hour sprints that you can do with people. They have something called Takeoff, which is a 20-minute morning ritual where you set your intentions and do something a little bit more woo-woo and kick off your day with that. And then they have like drop-ins all day long where you can just like drop in, be like, okay, this is what I'm doing. So I subscribe to it. I missed my drop-in this morning. I think they're in Europe, so the hours are a little bit different. I love it. Why would you raise money for that? I could. You could stand that up. You know, it's like a distributed kind of non-membership, non-personal, almost like a YPO or something, like a touch-and-go YPO.

But I think category-specific Zooms, like again, that's another thing.

I was just about to say that, like niche it down to solopreneurs, digital nomads, artists, etc.

Again, dog owner, like certain breed dog owners, like you may have gotten together or whatever. You have friends who have the same dog. You would have talked Talk to them in person, and now in the world of Zoom, if you can get me five people who own the same dog I own, you probably have some notes to share and some interesting things. I think I think people just want to connect with people.

Totally. So we we started this by talking about you know side hustle ideas for 2023, and I want to keep the ball rolling in kind of how we are thinking about having an awesome next year, and do so by talking about like what is our process for reflecting on 2022, and how does that inform our choices moving forward? So um. I want you guys to start by sharing just like, what do you guys do to reflect on your year in a way that helps inform your year moving forward? Jesse, do you have a process?

Yeah, I do. You know, the one funny thing I'd say is that like, I also, you know, I've talked about energy in the past and like I found just like some years I'm like so eager to reflect and some years I'm not for whatever reason.

What is this year?

This year I think I'm pretty eager to reflect. Like I'm at a good, interesting inflection point with several things and I feel like, okay, this is a good opportunity to take a zoom out. See what's there. I like I've always done New Year's resolutions and that kind of thing, but I think real reflection, you know, I I'm a I'm a nerd around some of these things. Like I probably ten years ago have like pretty high level goals. Like I sat down with my wife and I was like, okay, across all these things like family, you know, being a good dad, like a certain amount of money, a certain amount of impact in the world, religion and spirituality, and really like set like okay, what do I want to be when I'm sixty? or something crazy.

Can you share any of the goals you had?

I can pull it up or whatever. But, but it's, you know, it's like some are more specific than others, but it's like certain amount of time spent, you know, time with my family, you know, a certain dollar amount I want to make. Yeah, a certain amount of impact. Like how many people do I want to try to impact in different ways? And so I look at it and it's just a good chance to kind of go like, am I trending in this? First of all, the first question actually is not am I trending? The first question is Are these still what's important to me? So I think that's another thing is like sometimes you set a goal and then you look back on it and you're like, oh no, no, no, I thought that was important to me, you know? And now it's no longer important to me. And I think that's a great, really important thing. Don't get attached to your goals. Don't get stuck to them. Make sure you're constantly taking inventory of yourself and what you want. And then I'll kind of just like track 0 out of 10, something very simple. Okay, how am I— how do I feel like I'm trending or tracking on this? And kind of re-up. I try to zoom them down for the year. What are some of the big areas that are impacting these. I just kind of draw it out. Okay. For business. Okay. Am I— is this going to trend there? Is that going to trend there? Father. And then kind of go through a handful of different things I want to change or I want to be doing differently. One of my big ones for, for this coming year, just as an example, is like I want to reduce my calendar by 20 to 25%. Like I just want it to be less busy.

Mm-hmm.

And I don't know exactly how I'm going to do that, but it's like, okay, there's a goal. Okay, now what, what needs to happen in order to get that done? There's some other ones more like fitness and health related. I had like a bad blood test. So it is pretty encompassing for me as an individual. And then the businesses obviously do goal setting, which we talked about in a previous episode. But I think it's important to— one thing I've learned, for me at least, like I get my eyes get bigger than my tummy when it comes to goals. I'm like, yeah, I want to do that and I want to be 7 feet tall and I want to lift 500 pounds. And then I like over time I'm like, well, hold on, I got to set fewer goals. And then I also want to take them on serially versus in parallel. Yeah, that's a big one. Like a major change I want to start to go, okay, I'm going to do it serially as I go through it and kind of figure that thing out. So it's a little bit, it's a little bit random. It's usually half a day. Then I'll usually— the other thing for me, I'm a talker. Like, you know, I like talk to friends about them. Like, hey, what do you think about this? Here's kind of what I was like. Do you have thoughts on this? Or— and then people, my wife and some of my closest friends, they know me well. Like, dude, you're not going to do that one. Like, come on. Yeah, there's a little bit of calibration with sort of the brain trust, if you will.

I think just the point you make around sequencing is like so important, not just for life, but even for business. I feel like that's one of the things, one of— if I was to reflect on like the mistakes we've made over the years with Morning Brew, it's, it's we were really ambitious, which was great, but at times we were ambitious all at once in one point of time versus sequencing like Let's do this thing. Once that thing is done, let's focus on this thing. And so I think by sequencing, it allows you to both be ambitious but also not dilute yourself or be unfocused. And so I think that's a huge point. Sophia, how, how do you set the table for 2023?

Yeah, I just discovered and I'll— we can pull up a screenshot. In 2012, I discovered in my notes in my phone just a few days ago My 2012 goals. So 10 years ago, my goals were something like take money off the table at Nasty Gal, buy mom a kitchen. I ended up paying off her mortgage, buy a house. And there was really funny things like eat an apple every day or eat 3 pieces of fruit, which like I'm sure I never did. I actually have a goals guide that we created at Business Class that's like a kind of huge guide on thinking through like setting your intentions all the way to creating actionable steps. And it's much more deep than the way that I think about it every year, which is a little bit more nimble, which is in the front of the flight planner. And I go through what I want to quit, what I want to learn, what I want to have, what I want to start, what I want to stop, and then what I want to be. And then go through intentions. And so those intentions, the categories for those is personal health, career, adventure, home, and spiritual. And at the beginning of last year, I did that. I think I— I don't know if I burned it or I kept it. I tore it out of something and I put it in my journal. My journal has a bunch of pages that aren't even bound because I shove in so many notes and then often never look at them again. But I think I did keep this. And at the end of every year, I think it's important to Reflect, right? Like, did I achieve these things? That's kind of where you start. And Alex, I really loved your method. We talked about this and it really inspired me also. There's so many ways to do this, but yeah, your method talks about what gave me energy and what took my energy.

And by the way, this is the most unscientific method ever. No, I love it.

And it made me realize, like, I know what doesn't give me energy, but oh shit, heading into 2023, 23, what gives me energy? Like, I was like, tell us yours, because I love it.

And what I'll say is I've probably done this, definitely done this fewer times than you guys because I've never done this. This is the first time.

Because you're like 28 and—

Yeah, yeah, yeah. Because I'm basically still in high school. No, I just, I locked myself in like the lounge in our building, kept my phone away. And just I wrote down the questions that I try to reverse engineer, like what questions can I ask myself that I think will lead to a relatively good compass of how I want to spend my time? So I asked myself 6 questions. What gave me energy in 2022? What did not give me energy in 2022? What I want— what do I want to do more of in 2023? What do I want my life to look like ten years from now? So similar to the Jesse question, except I guess I said ten years from now. It sounds like you asked like forty years from now, or maybe maybe you're a little older, sir. Thirty, twenty years. I had to punch that.

Amazing.

Five, what would a successful 2023 look like? And six, what would an unsuccessful 2023 look like? And just to get specific because I feel like. I don't know. I always latch on to specificity. I'll just share a few things that came up for me. So what gave me energy this year? A few things. And I'm live reading this, so I may have to live edit if there are things that will get me in trouble for saying. What gave me energy is feeling like I'm taking care of my body. What gave me energy is building something from scratch that solves a problem I'm excited about. What gave me energy is surprising my fiancée with gifts and planning new experiences. Being silly and playful, growing as an interviewer, feeling like I'm in control or on top of my finances, my health, and my mind. And then there were a number of others. And then what did not give me energy or took away energy? The feeling of not being disciplined. The course that I taught this year, the Strategy for Creators course, I didn't really get good energy from that. Calls and meetings with people where I don't feel like I'm learning or growing, worrying if I have enough money and how much I lost in the markets this year. And then what do I want my life?

I forgot my Fidelity passwords. I have no idea.

That's probably honestly, I'd probably that'd probably be a good thing to happen to me. And then what do I want my life to look like ten years from now? And so I wrote down. It's funny, I didn't know the categories you use for intentions in your flight planner, but I would say mine were relatively similar other than spiritual, because I don't— maybe I'm a little bit spiritual, but I'm not religious. But I wrote down family, friends, work, self, wealth, health, and miscellaneous. And just to give an example, like, what do I want my life to look like 10 years from now? 3 healthy children, 1 to 2 dogs, A partnership with my wife defined by love, respect, and shared values, and spend as much time with my family as I desire. Friends, a group of friends that I have love for, who have love for me, who make me a better, happier person. And I went through all of these and then basically taking the things that give me energy, take away energy, and what I want my life to look like 10 years from now. I answered, what would a successful 2023 look like and what would an unsuccessful one look like? And obviously the unsuccessful is oftentimes just an inverse Of what the successful was, so that was my process.

That's awesome. I just yeah, it's great.

Say you're like such an optimistic, positive person.

Like it is a gift. It is a gift and a curse.

It really is. Like you're like the I mean all American. Well, not Jewish, but like there's something just like so all American Jewish about you that's really admirable, and thanks for sharing that.

Yeah, yeah.

I think I think that you know. Those are right. I think anyone listening, I said this about goal setting for your company too, and I'd say it personally, do the thing that's, that you're going to do.

Yeah.

You know, like it could be one question. What, what was, what do I want to do next year? And I think it's because sometimes people get intimidated by these big processes and it just has to be whatever you're actually going to spend, get to spend time on. And I know for me, I don't know if you guys are the same way, but there's times when I can sit down with those questions and I won't get anywhere with them. And there's other times where I'm like, it just— they ooze out of me because for whatever reason, I'm like sitting there and I wrote myself an email the other day, just somewhat related to a lot of those questions. And it was just like it came out of nowhere, felt like it came out of nowhere. The other, the other thing that I've been trying to get better at is habits versus goals. I don't know. There's a good article out there. You can Google it. And also Patrick O'Shaughnessy talks about like the goal-free life and that's like for where that's been most successful for me has been exercise. So I used to approach exercise as like What's my goal? I'm going to like run a half marathon and I'm going to be— and like, that's like everything in life. I'd be intense about it and I would just never sustain. It would never sustain for me. And I flipped it to kind of going like, I want to get activity of some kind, like actual real activity, heart beating fast 4 times a week. And I'm not going to guilt myself if I miss something. I'm just— it's just my— it's a habit I want to make. And I like, I think I've done it every week for the last— and I'm not— now I don't think about it. I have tennis a few times a week.

Amazing.

And so that's like another one I would just throw out there. If you're struggling with goals, that the concept of habits is sometimes way more powerful in terms of creating something sustainable.

I think that's spot on. It's funny, I've been thinking a lot about this recently because I haven't read the book in probably 5 or 6 years, but I read Power of Habit by Charles Duhigg like 5 or 6 years ago, and I believe it was in that book that there was this whole idea of Keystone habits. So it's like, what are the habits that you build that have a trickle-down effect in the rest of your life? And why? I think one of the examples they gave was this case study where they had smokers who were trying to quit smoking, half of which would work out 5 days a week, half of which wouldn't. And the decrease in the smoking rate of the group that worked out was significantly higher. And so I've been trying to actually implement that in my own life. I just started working with a trainer and a nutritionist for the first time, which for anyone that knows me really well, like I am the most cheap human being ever. So I was always afraid of spending on a trainer, on nutrition. But I think that now I've worked out and watched, kind of been mindful about my eating for the last— it's been 3 weeks now. But I think it has created for me what it's done is created discipline. And I think that discipline is having an impact on other areas of life that just aren't health and wellness.

Yeah, it's like your eat an apple a day, Sophia. Like, it's the same exact concept to me.

I— there's a newsletter I actually read this morning that really inspired me, and this guy's name is Steve Schlafman. Oh yeah, newsletter's called Light Waves. And a lot of these more woo-woo newsletters I kind of skim through, and it's just— some of them are just so long. Um, but he had one called The Year of No Decisions, I think, this morning. And I also just want to, you know, share that it's okay not to have big goals. It's okay. You know, the temptation that he described, you know, he's a recovering VC. So the temptation he does— and an operator. So the temptation he described as a former VC and operator was starting something new. And he's become a coach.

The pull is strong.

And his, you know, he's now, you know, the operator finance guy turned leadership coach. But his nature is to continue starting things. And I think it's okay. For a year to stop and make no decisions and that to be your goal and to sit with totally not knowing and ambiguity in the liminal space. And that's something people don't really talk about because there's kind of a shame in not setting goals and in letting yourself be in the not knowing or the valley of— what is it? There's something that— no, I mean, it doesn't have to be despair.

That's the valley of emptiness.

If you reframe it, maybe it's not despair.

Yeah, yeah, I think that's right.

It's a matter of sitting with yourself.

I tried for 6 months between leaving Ampush the CEO and starting GatewayX to do that. And actually, my Enneagram type is one that hates empty. It's like a thing that I like to keep myself. And it was so fucking hard. I mean, it was. I started feeling anxiety. I started like, oh, no, no, can't do anything. And being with that was very, very challenging.

And I think the urge, our nature to make ourselves busy, we can be running towards something, but we can also be running from things, and it's important to check ourselves and make sure that we're not occupying ourselves to escape something that we are avoiding personally that we got to deal with before we can really be successful or satisfied in anything.

Oh yeah, we are great at this.

We're getting deep today.

We are great. We are great at just doing— we're great at doing butt kicks, high knees, and running in place over just like doing a nice gradual walk towards the North Star. That's pretty dope. That's awesome. I don't know. I don't know if it's helping that business right now, but it's a cool product.

All right. Let's do this.

Yeah. Yeah. So on your bingo card for 2023, as you're setting intentions, is buying a domain for $240,000 on the goal list?

No. I'd like to sell one for $240,000.

I was talking to Andrew Gosdecki.

Yeah.

Who— he has this business called MicroAcquire that I invested a little bit into 18 months ago. And the business is very simple. It's a marketplace for buying and selling software businesses. And businesses as small as like $10,000 can list on there all the way up to— now they do multimillion-dollar deals. But he's been wanting to switch the brand from MicroAcquire and MicroAcquire.com to Acquire. So he wanted to acquire the Twitter handle Acquire and he also wanted the brand to change. So he bought Acquire.com for $240,000. Do you guys think it is worth it that he made that purchase? And I'll just give you a little bit more information about the business. I believe the business is north of, you know, $2.5 million ARR a year. It has 5 years of cash in the bank from the money that they've raised. It's profitable. Is that Siri listening to me? Oh, Siri is listening to my watch. Wow. She's taken down notes about this entire domain acquisition.

You're going to get ads about—

Yeah, I'm going to get this shit targeted at me from GoDaddy. And so he spent $240,000 on this. Do you guys think that it makes sense and would you spend that much on a domain for your businesses?

For that business, no, because I think MicroAcquire is actually a great domain name because that's what it is. It's not— acquire is so broad. It could be an acquisition company. It could be a marketing business. I think MicroAcquire is really descriptive and it's kind of a great name.

But what if you want to start selling non-micro businesses?

Maybe.

Yeah. For a B2B business like that, I don't— I I wouldn't do it. I mean, Andrew's a super bright guy, and I think what I would— the conclusion I would draw from him is like, if you make the most of it, I'm sure it can be a very good decision and high ROI decision. I wouldn't do it. It's just expensive. It feels like a really big bet that doesn't— what else could you do with that bet? What else could you do with that money? But it doesn't— for consumer businesses like, I don't know, grocery.com or things like that, like there's such a— it's such a huge opportunity from a brand building perspective for something like that. It makes much more sense to me. But for a I don't know, MicroAcquire, Acquire.com. I don't think there's any differentiation in terms of who's the buyers or sellers that it's going to change all that.

Didn't you sell a domain for 5 figures?

I did.

What? Tell the story.

The story. Well, like, like lots of entrepreneurs, I have a bad habit of buying domains that I think of in my head and I'm like, one day we'll do something with this. And I own way too many of them. But, you know, obviously if you're buying domains, you try to find a theme that you're early on that you think is going to become huge and you start buying domains related to it. So we were on the bleeding edge of Facebook back in 2010 and '11. They had this thing called Open Graph and it was all about like, what are your friends like? What do you like? Like before Facebook ads were Facebook ads, they were this like referral concept that Zuckerberg came and announced and it was this huge thing and it was all about the graph, the graph. So I was like, ooh, graph, that word is going to become everywhere. So I bought like adgraph.com, audiencegraph.com, like I bought everything graph.com and I got a ping from someone who was just like, hey, I want to— I'm starting a startup and it's going to be called Audience Graph. Can I buy your domain? And I sold it for 5 figures and a little bit, a little bit of equity was wonderful. So that was the worst thing for my habit though, because then I was like, this has had massive ROI.

Do you think it's a scummy thing To squat on domains?

No, I don't think so.

I think it's bad when you're running really garbagey ads.

Yeah, it can be. I guess it's all about how you do it.

Yeah. Yeah.

I have a story.

Let's hear it.

So I, I bought a bunch of domain names when I was thinking about naming Nasty Gal, and one was like iheartvintage.com. The other one was like thevintagestylist.com. I didn't know what I was going to end up doing. But I bought nastygalvintage.com once I left eBay and it took off. But we stopped selling vintage, or we introduced more than just vintage. And I needed nastygal.com. And as you could guess, the person who was squatting on that domain was running ads for videos of like what you might consider nasty gals. And I had to contact this porn domain broker anonymously. I want to just say that if you're looking to buy a domain name, just make some random email address. If it has— do not have any name or email address associated with a successful business because they will jack up the price. So I contacted them anonymously and I bought it for $8,000.

Nice.

It was a great investment. But we didn't own nastygirl.com. And even after buying nastygal.com, people, just like people call me Sophie, they called it nasty girl sometimes. And so these girls would be like, Grandma, I really want this dress. Check out this— Dad, check out this dress.

Poor Grandma.

And they type in nastygirl.com and it was a memory that none of them will ever forget.

Is Nasty Gal still— is it still a porn site?

I'm pretty— and that's got to be like a pretty valuable—

I would have to think that's a— oh no, Nasty Gal is owned by Nasty Gal.

Oh, good for them.

Yeah, I just went to Nasty Gal and it redirected.

That's not how I spent the company's money when I was there.

Okay, so to wrap this thing up, if for entrepreneurs like On the topic of domains, when, when do you think it does make sense to fork over a good amount of money for a domain? Like, what are the contexts where that actually could be a smart move?

I think you have to be a huge business and a consumer-oriented business, and the brand has to matter a ton. And I just think you can get so far with getdetergent.com and buy Lights.com. I just think you get so far with these slightly different names.

I think be smart with your brand name. Like, go look for domains that are— that exist before you name your business.

I was going to say, it sounds like it's a creativity problem.

Yeah.

How much they cost to buy before you start your business. Don't start your business with a bad name and then have to, you know, retrofit a better domain name after the fact.

Totally. Yeah. Like the reason people gave when I asked about this was A, it could lead to a traffic bump if you get like a high traffic domain. But the question I always have in my head is like, say you could buy a website that has 25,000 page views a month to that domain already. What could you do with that $25,000? Like, could you just buy just as much traffic or more using that money you would have invested in the domain? And then other people have said for trust, like if you're in low trust industries, it can make sense. So A guy has this business, Rivalry.com. He used to have Rivalry.gg, and his view was he's in the esports betting space, which has a ton of customer distrust. They don't know what are like legal esports sites versus illegal ones. And his view was like a .com was actually a symbol of stability for that space, which I think could make sense. But overall, yeah, I, I'm of the belief like Be really creative with your business name, and you can probably come up with something that you can get cheap in the early days. Any final words before we sign off for this episode?

Happy.

No, this was fun.

Yeah, this was a good one.

Have a great 23.

Have a great 23, guys. And if you have any ideas or feedback for the show, shoot us an email at thecrazyones@morningbrew.com. And if we could just ask for one gift from you for the holidays, whether it's Hanukkah, Kwanzaa, Christmas, please leave us a review on the podcast apps, whether it's Apple or Spotify, and subscribe to the Crazy Ones YouTube channel. Take it easy, everyone.