We Give Away 7 Profitable Side Hustle Ideas for 2023

Jesse Pujji: 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 a hundred thousand dollars 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 the best part of anything like this.

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

Sophia Amoruso: And I'm Sophia Amoruso.

Jesse Pujji: Yo, this is Jesse Pujji.

Alex Lieberman: 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 six 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 six figures next year without working full-time, on an idea. So who wants to kick it off?

Jesse Pujji: Can I start with a confession?

Alex Lieberman: Yeah.

Sophia Amoruso: Yeah.

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

Sophia Amoruso: I mean, isn't Gateway X kind of a suite of side hustles?

Jesse Pujji: Well, yeah, it's a little different now, but when it was just me and I had a job full-time...and maybe I'm just saying that because if you're listening and I think there's types of people, like I'm one of those people who, if my focus and energy's not going to something, like I can only focus 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 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 went anywhere.

Alex Lieberman: Well, I guess, what do you define a side hustle as, then? Because to Sophia's point, wasn't Kahani a side hustle before it became a business that you now have raised for? Wasn't GrowthAssistant a side hustle before you put in place a CEO? What would you refer to those as?

Jesse Pujji: No, I think those were highly intentional business...I probably used full-time for six months of getting GrowthAssistant off the ground. I was, "This is what I'm doing." I'd wake up every morning, it's what I obsessed about. It's what I thought about every second I could. And for whatever reason, that's how I'm wired. Every time I try to go, "Okay, this is what I'm focused on and then this 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 have lots of friends and people I've interviewed in 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 the least risky by far.

Alex Lieberman: Yeah. And out of curiosity, my guess is you'll say they're just real businesses, that you're just not active in the day-to-day now, but the businesses within Gateway X, right, you have three of them; you have Unbloat, you have GrowthAssistant, you have Kahani. What do you consider the two that you're not running the day-to-day of now? Businesses that you've put in an operator?

Jesse Pujji: Yeah, they have management. I mean, they have several people who it's their full-time job, it's what they obsess over. So I think, 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, and that...

Sophia Amoruso: Is that your side hustle?

Jesse Pujji: Well, no, it got me excited when the first episode, she finds some jacket and she sells it on eBay on the side. Well, she'd gotten fired, whoever the character is.

Sophia Amoruso: Yeah, there was no side, it was the front, but it was a real...

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

Sophia Amoruso: The whole thing is weird. It's just like...

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

Sophia Amoruso: Like 50/50. 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 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 I would never have figured out or invented. I would never have even opened a brick-and-mortar store. 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.

Jesse Pujji: Well, don't tell me, dude, I'm watching it now.

Sophia Amoruso: My mom wasn't 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...

Jesse Pujji: But 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.

Sophia Amoruso: I guess it was in the beginning. It was, it was.

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

Jesse Pujji: I'm not judging it, I'm just saying every time I tried, when I worked in One Wall Street, I tried to get this media site going on the side. Do you remember the whole FMyLife website?

Alex Lieberman: Yeah, yeah, yeah.

Jesse Pujji: It was an early thing. And then it was like we bought all these domains: My Life Is Finance and My Life Is Black, My Life Is Jewish, and it was supposed to be basically offshoots of that to get people to post funny puns about their little subsegment. I still own the domains; it never went anywhere.

Alex Lieberman: By the way...

Jesse Pujji: I couldn't get myself to focus on it.

Alex Lieberman: It's nice foreshadowing for us talking about your domain story in 30 minutes, but Sophia, what's your view on side hustles? Do side hustles work for you? Do you have the same definition as Jesse?

Sophia Amoruso: Everything I start...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 in 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 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.

Alex Lieberman: So wait, out of curiosity, what is...

Sophia Amoruso: So it became a bit of a front hustle.

Alex Lieberman: What assumptions did you get wrong that led it to being far more of a full-time job/business than you thought it was going to be when you started it?

Sophia Amoruso: I mean, it wasn't, for the first year and a half. I took half of last year off. I bought a house in Kauai, I did so well, I took the summer off. I was on an island five 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. 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 eventually they're excited to learn from me or someone else and they become part of the Business Class world and they then upgrade to Business Class, which is huge investment. It's $2,000.

And also there are opportunities. I mean, again, it could feel like a side hustle, not to build a YPO type thing, but yes, small groups that pay more than the cost of Business Class to join. And I hire a few coaches to mentor them, but that doesn't necessarily have to be something where I'm building what Sam Parr is trying to build in a $200 million business. And he's talked about that. It's not super under the radar anymore. He talked about it...

Alex Lieberman: Well, now it isn't.

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

Alex Lieberman: Okay. So I jotted down five 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 way that I generally think of ideas or moving forward with ideas is I know that I have 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 six 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, Hoboken is the fourth-highest density city in the US, which I didn't realize. The demographic is what I like to call "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...I literally went through the cost of all the stuff. The cost of getting a dog grooming trailer is $63,000 a year, and I just start making assumptions like, "If we get five dogs a day just on the weekends or five dogs a day on the weekdays, and we charge them 60 bucks and the cost of labor, the groomers, 22 something dollars an hour, the payback period could be anything from six months to three years." Three years if 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 two weeks.

Sophia Amoruso: In the shower?

Alex Lieberman: Yeah, that's what we do. We bring Rambo into our shower.

Sophia Amoruso: You have a big dog. You have a bigger dog.

Alex Lieberman: Yeah, he's a 55-pound dog.

Sophia Amoruso: Yeah, mine are like hamsters.

Alex Lieberman: And he hates it. There's a whole blow-drying process. And also, 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 at the end of the day, if you turn every company into a media company, all of a sudden, monetization can grow into also ad dollars and not just the business, so that's one idea.

Jesse Pujji: Or franchise, create a franchise around it.

Alex Lieberman: Exactly.

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

Sophia Amoruso: Sounds like a business.

Jesse Pujji: What side-ifies it?

Sophia Amoruso: Like three years payback period?

Alex Lieberman: So I guess I define side hustle a little bit differently on that one. My view is, "What is something that I can spend a good amount of time on in the early days, and then I only have to spend five hours a week after that?" And to me, once it gets to five 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 two. One is...this is the ridiculous one, getting my honeymoon sponsored. Carly and I are planning our honeymoon. I'm not actually going to do this, but there's a part of my brain that I thought about this. I didn't realize how much goes into the honeymoon process, how big of an investment it is. I have 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 that, I would assume, is more of a side hustle.

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

Sophia Amoruso: At Girlboss when we did brand deals 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...

Alex Lieberman: Why wouldn't they, though?

Jesse Pujji: Hold on, there's got to be a business of calling the points guy and saying...I mean, you're one person, Alex, but hundreds of people filming and making their own content on their trips, and then this...

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

Jesse Pujji: My ideas...I think those are all, with respect, Alex, I think those are all real business ideas versus side hustles.

Alex Lieberman: Okay, what's your idea?

Jesse Pujji: I think that part of the side hustle thing is you have to leverage some of the best parts of scalable businesses. And so scale...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 the dog grooming is so services-y heavy it just feels like it's going to be a huge pain in the ass.

So I had two. None of them are amazing. But I think with the proliferation of no-code tools, I think, I mean, there's probably six 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 bucks."

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, accomplish Y. I stumbled upon these business with my kids, coloring, the coloring books. You can Google anything and there's these...they must be side hustles, you can download a coloring of Mickey Mouse or Wizard of Oz or something random and you pay a buck every time.

Alex Lieberman: So just outlines of the thing that you can download to color?

Jesse Pujji: Because my kids are bored and I'm like, "They want to color something." "Okay, here you guys go," I print this out, I paid a dollar. 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 two a week and then sell them, basically show up on Google," and that's one version of it.

Alex Lieberman: This is what Thomas Frank does. Thomas Frank, the YouTuber, he shifted from having this massive productivity channel that has 2 million subscribers to 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, it has 130,000 subscribers, and he's doing, I believe, something like $150,000 a month in Notion template sales, 90-something-percent margin.

Jesse Pujji: 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...

Alex Lieberman: Who bought it? Was it Ampush?

Jesse Pujji: Ampush bought it.

Alex Lieberman: Got it.

Jesse Pujji: 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 just purely passion. "I'm going to write about this category, I love this, I'm going to order them, I'm going to review them," and everything like that. It started to snowball. Other people who love 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, pick a category again that you love, that you know of and just start writing about it or some way you could contribute to content. I think you could totally do it on the side, but then it gets the scale of media over time. So those are my two.

Sophia Amoruso: 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've 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 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.

Jesse Pujji: And I think to riff on that for a second, I think 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 a hundred thousand dollars 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 the best part of anything like this.

Alex Lieberman: And that's why sometimes I think the best businesses really do start as side hustles, that you just genuinely wanted to learn about something. 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 paid marketing or social, it was people in his list referring other people.

But there were none of these, the segmentation things or marketing tools in MailChimp to do this, so he's like, "I ended up just building the system that I had scraped together when I was doing my blog on MailChimp." And obviously when he started this, he would've never had an idea he was going to build a SaaS product for every creator and blogger.

Jesse Pujji: 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 that...

Alex Lieberman: Oh, yeah.

Jesse Pujji: By the way, it's so funny, there's so many email newsletters, they're freaking annoying, and even I have mine and I'm like, "Does anybody..." But I think what's missing is actually a diversity. To your whole point about pet owners, but every breed should have its own newsletter because...so there's probably all these little things that the more niche you get, and you go, "I'm going to just write every week about..." I'm not a dog person, you guys have dogs...

Alex Lieberman: Other side hustle coming soon. I haven't told you about that one yet.

Sophia Amoruso: Totally. What Red Ventures did with websites someone can do with newsletters, is just something really niche.

Jesse Pujji:  Yeah. Exactly.

Alex Lieberman: Sophia, before we push forward, I just want you to share, you were telling me about this other idea that I think is so interesting in this remote environment. Talk about the idea you shared with me.

Sophia Amoruso: Yeah. I've thought about it and I've seen kind of rinky-dink creators doing stuff like this with their communities. And I've also heard that people with ADD doing co-working or being kind of held accountable in some way live just...and that works for me, is 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 five a day and that's two hours of silent work. And you state your intentions at the beginning.

Jesse Pujji: It's so absurd it's a business.

Alex Lieberman: I love it.

Sophia Amoruso: You do a group stretch in the middle.

Jesse Pujji: I love it.

Sophia Amoruso: 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 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 it'll look kind of bad if you leave, even if you want to. So they have Power Hours, which are an hour sprints that you can do with people. They have something called Take Off, 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 drop-ins all day long where you can just 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.

Alex Lieberman: I love it.

Sophia Amoruso: But why would you raise money for that? You could stand that up. It's like a distributed kind of non-membership, non-personal, almost like a YPO or something, like a touch-and-go YPO.

Jesse Pujji: But I think category-specific Zooms, again, that's another thing...

Alex Lieberman: I was just about to say that, like niche it down to solopreneurs, digital nomads, artists, et cetera.

Jesse Pujji: Again, dog owners, certain breed dog owners, you may have gotten together or whatever, you have friends who have the same dog, you would've talked 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 people just want to connect with people.

Alex Lieberman: Totally. So we started this by talking about side hustle ideas for 2023, and I want to keep the ball rolling in how we are thinking about having an awesome next year, and do so by talking about what is our process for reflecting on 2022, and how does that inform our choices moving forward? So 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 moving forward? Jesse, do you have a process?

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

Alex Lieberman: What is this year?

Jesse Pujji: This year I think I'm pretty eager to reflect. 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've always done New Year's resolutions and that kind of thing, but I think real reflection...I'm a nerd around some of these things. I probably 10 years ago have like pretty high-level goals. I sat down with my wife and I was like, okay, across all these things like family, being a good dad, a certain amount of money, a certain amount of impact in the world, religion and spirituality, and really set, "Okay, what do I want to be when I'm 60?" Or something crazy like that.

Alex Lieberman: Can you share any of the goals you had?

Jesse Pujji: I can pull it up or whatever. But some are more specific than others, but it's like certain amount of time, spent time with my family, a certain dollar amount I want to make, a certain amount of impact. "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, "Am I trending in this direction?" 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 sometimes you set a goal and then you look back on it and you're like, "Oh no, no, I thought that was important to me 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 track zero out of 10, something very simple. "Okay, 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 that just kind of draw it out?" Okay, for business, "Okay, is this going to trend there? Is that going to trend there?" "Father," and then go through a handful of different things I want to change or I want to be doing differently.

One of my big ones for this coming year, just as an example, is I want to reduce my calendar by 20% to 25%. I just want it to be less busy and I don't know exactly how I'm going to do that, but it's like, "Okay, here's a goal. Okay, now what needs to happen in order to get that done?" There's some other ones more like fitness and health-related. I had 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, 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 seven feet tall and I want to lift 500 pounds." And then over time I'm like, "Well, hold on, I gotta set fewer goals" and then I also want to take them on serially versus in parallel.

That's a big one, 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 random; it's usually half a day. Then usually the other thing for me, I'm a talker, I talk to friends about it. I'm like, "Hey, what do you think about this? Here's kind of what I was..." Like, "Do you have thoughts on this?" And then people, my wife and some of my closest friends, they know me well, they're like, "Dude, you're not going to do that one. Come on." And so there's a little bit of calibration with sort of the brain trust, if you will.

Alex Lieberman: I think just the point you make around sequencing is 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 the mistakes we've made over the years with Morning Brew, 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 do you set the table for 2023?

Sophia Amoruso: Yeah, I just discovered...and we can pull up a screenshot, 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 three pieces of fruit," which I'm sure I never did.

I actually have a goals guide that we created at Business Class, that's a kind of huge guide on thinking through, 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 a 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 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 is 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, "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...

Alex Lieberman: By the way, this is the most unscientific method ever.

Sophia Amoruso: No, I love it. And it made me realize, "I know what doesn't give me energy," but oh, shit, heading into 2023, "What gives me energy?" I was like, "Uhhh." Tell us yours, because I love it.

Alex Lieberman: Yeah, 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 year that...

Jesse Pujji: Because you're like 28 and we're old.

Sophia Amoruso: Oh, poor guy.

Alex Lieberman: Yeah, I'm basically still in high school. No, I locked myself in the lounge in our building, kept my phone away, and I wrote down the questions that...I tried 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 six questions. "What gave me energy in 2022? What did not give me energy in 2022? What do I want to do more of in 2023? What do I want my life to look like 10 years from now?" So similar to the Jesse question, except I guess I said 10 years from now. It sounds like you asked 40 years from now, or maybe you're a little older, so 30, 20 years. I had to punch that.

Sophia Amoruso: Ha, ha, ha, ha, zing.

Alex Lieberman: 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 onto 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 to...

Jesse Pujji: I just forgot my Fidelity passwords. I have no idea...

Alex Lieberman: Honestly, that'd probably be a good thing to happen to me. And then, what do I want my life to look like 10 years from now? And so I wrote down...it's funny, I didn't know the categories you used 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, "What do I want my life to look like 10 years from now?" Three healthy children, one to two 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.

Jesse Pujji: That's awesome. Yeah, great.

Sophia Amoruso: I just have to say you're such an optimistic, positive person.

Alex Lieberman: It is a gift and a curse.

Sophia Amoruso: It really is. You're like the...I mean, all-American...

Alex Lieberman: Well...

Sophia Amoruso: ...Jewish, but there's something just...

Alex Lieberman: The all-American Jewish...

Sophia Amoruso: ...so wholesome about you that's really admirable, and thanks for sharing that.

Jesse Pujji: Yeah, I think 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 you're gonna do.

Alex Lieberman: Yeah.

Jesse Pujji: It could be one question: "What do I want to do next year?" Because sometimes people get intimidated by these big processes, and it just has to be whatever you're actually gonna 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...they ooze out of me because for whatever reason I'm 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. It felt like it came out of nowhere. 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 Roshanas, he talks about the goal-free life. And where that's been most successful for me has been exercise. So I used to approach exercise as, "What's my goal? I'm going to run a half marathon and I'm going to be..." 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, "I want to get activity of some kind, like actual real activity, a heart beating fast, four times a week. And I'm not going to guilt myself if I miss something; it's a habit I want to make." And I think I've done it every week for the last...and now I don't think about it. I have tennis a few times a week.

Alex Lieberman: It's amazing.

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

Alex Lieberman: 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 five or six years, but I read Power of Habit by Charles Duhigg like five or six 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 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 five 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, 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 three weeks now, but I think it has created, for me what it's done has created discipline. And I think that discipline is having an impact on other areas of life that just are in health and wellness.

Jesse Pujji: It's like your "eat an apple a day," Sophia. It's the same exact concept to me.

Sophia Amoruso: There's a newsletter I actually read this morning that really inspired me, and this guy's name's Steve Schlafman. The newsletter's called Lightwaves. And a lot of these more woo-woo newsletters I kind of skim through and some of them are just so long. But he had one called The Year of No Decisions, I think, this morning. And I also just want to share that it's okay not to have big goals. The temptation that he described, he's a recovering VC. So the temptation he...and an operator, so the temptation he described as a former VC and operator was starting something new, and he's become a coach.

Alex Lieberman: The pull is strong.

Sophia Amoruso: And he's now 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 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?

Jesse Pujji: Despair?

Sophia Amoruso: No, I mean it doesn't have to be despair, that's the thing.

Jesse Pujji: Oh, the valley of emptiness?

Sophia Amoruso: If you reframe it, maybe it's not despair.

Jesse Pujji: Yeah, yeah, I think that's right.

Sophia Amoruso: Maybe it's just a matter of sitting with yourself.

Jesse Pujji: I tried for six months, between leaving Ampush as CEO and starting Gateway X, 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 started feeling anxiety, I started like, "Oh no, no. Oh, can't do anything, can't..." And being with that was very, very challenging.

Sophia Amoruso: 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're avoiding personally, that we gotta deal with before we can really be successful or satisfied in anything.

Alex Lieberman: Oh yeah, we are great at this.

Jesse Pujji: Gettin' deep. We're gettin' deep today.

Sophia Amoruso: I need help! I'm working on it.

Alex Lieberman: We are great at doing butt kicks, high knees, and running in place over just doing a nice gradual walk towards a North Star.

Sophia Amoruso: I got the Peloton Row.

Alex Lieberman: That's pretty dope. That's awesome.

Sophia Amoruso: I'm excited.

Alex Lieberman: I don't know if it's helping that business right now, but it's, I'm sure, a cool product.

Sophia Amoruso: It came yesterday.

Jesse Pujji: All right, let's do this AMA.

Alex Lieberman: Yeah, yeah.

Jesse Pujji: Go ahead.

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

Jesse Pujji: No.

Sophia Amoruso: No.

Jesse Pujji: Hard pass.

Sophia Amoruso: No.

Jesse Pujji: I'd like to sell one for $240,000.

Sophia Amoruso: What are you referencing? Who did this?

Alex Lieberman: I was talking to Andrew Gazdecki; 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 two and a half million ARR a year. It has five years of cash in the bank from the money that they've raised. It's profitable. Is that Siri listening to me? Oh, Siri's listening to my watch. Wow, she's taken down notes about this entire domain acquisition.

Sophia Amoruso: You're going to get ads about...from investment bankers.

Alex Lieberman: Yeah, I'm going to get the shit targeted out of 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?

Sophia Amoruso: For that business, no, because I think MicroAcquire's actually a great domain name because that's what it is. Acquire is so broad. It could be an acquisition company, it could be a marketing business. I think MicroAcquire's really descriptive and it's kind of a great name.

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

Sophia Amoruso: Maybe?

Jesse Pujji: Yeah. For a B2B business like that, I wouldn't do it. I mean, Andrew's a super bright guy and I think the conclusion I would draw from him is if you make the most of it, I'm sure it can be a very good decision and a 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 for consumer businesses, I don't know, grocery.com or things like that, there's such a huge opportunity from a brand-building perspective for something like that, it makes much more sense to me. But for, 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 much.

Alex Lieberman: Didn't you sell a domain for five figures?

Jesse Pujji: I did. AudienceGraph.com.

Alex Lieberman: Tell the story.

Jesse Pujji: The story? Well, 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 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 what are your friends like, what are you like? Before Facebook ads were Facebook ads, there were this 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 adgraph.com, audiencegraph.com, I bought everything graph.com and I got a ping from someone and it was just like, "Hey, I'm starting a startup and it's going to be called Audience Graph; can I buy your domain?"

And I sold it for five figures and a little bit of equity; it was wonderful. But that was the worst thing for my habit, though, because then I was like, "This had massive ROI."

Sophia Amoruso: Oh no.

Alex Lieberman: Do you think it's a scummy thing to squat on domains?

Jesse Pujji: No, I don't think so.

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

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

Alex Lieberman: Yeah, yeah.

Sophia Amoruso: I have a story.

Alex Lieberman: Let's hear it.

Sophia Amoruso: So 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 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.

Jesse Pujji: Nice.

Sophia Amoruso: It was a great investment, but we didn't own nastygirl.com. And even after buying nastygal.com, just like people call me Sophie, they called it Nasty Girl sometimes. And so these girls will be like, "Grandma, I really want this dress. Check out this..." "Dad, check out this dress."

Jesse Pujji: Poor grandma.

Sophia Amoruso: And they'd type in nastygirl.com, and it was a memory that none of them will ever forget.

Alex Lieberman: Is Nasty Girl still...is it still a porn site?

Sophia Amoruso: And that's got to be a pretty valuable...

Alex Lieberman: I would have to think that's a...oh no, Nasty Girl is owned by Nasty Gal.

Sophia Amoruso: Oh, good for them.

Alex Lieberman: Yeah, I just went to Nasty Girl and it redirected.

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

Alex Lieberman: Okay, so to wrap this thing up for entrepreneurs, on the topic of domains, when do you think it does make sense to fork over a good amount of money for a domain? What are the contexts where that actually could be a smart move?

Jesse Pujji: 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...get detergent.com and buy lights.com. I just think you get so far with these slightly different names.

Sophia Amoruso: I think, be smart with your brand name. Go look for domains that exist before you name your business.

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

Sophia Amoruso: 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 retrofit a better domain name after the fact.

Alex Lieberman: Totally. Yeah. The reason people gave, when I asked about this, was A, it could lead to a traffic bump if you get 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? Could you just buy just as much traffic or more using that money you would've invested in the domain?"

And then other people have said, for trust. 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 legal esport 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'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?

Sophia Amoruso: Happiness.

Jesse Pujji: No, this was fun.

Alex Lieberman: Yeah, this was a good one.

Jesse Pujji: Have a great '23.

Alex Lieberman: 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, Kwanzukkah, 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.