Dec 20, 2022 · 47m · founders-journal
We Give Away 7 Profitable Side Hustle Ideas for 2023
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Hosts Alex Lieberman, Sophia Amoruso, and Jesse Pujji brainstorm profitable side hustle concepts for 2023, share their personal frameworks for year-end reflection and goal setting, and evaluate the financial return of purchasing premium domain names.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Alex holds 41% of the talking time here. How this is scored →
Alex as informed peer 5.5 Guest teaching 4.0 Guest disagreement 2.8 Alex pushing back 3.3
speaking balance: gold is Alex, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 15:21 Jesse dismisses Alex's proposals as real businesses, not side hustles
Jesse candidly rejects Alex's entire slate of ideas, pointing out that service-heavy businesses like mobile pet grooming become an operational burden rather than leveraged side hustles.
Hardest push from Alex ▶ 3:09 Alex presses Jesse on his portfolio companiesAlex refuses Jesse's framing that he is terrible at side hustles by listing GatewayX ventures like Kahani and Growth Assistant that started on the side before hiring CEOs.
Biggest teaching moment ▶ 15:26 Jesse educates on scalable vs service-heavy side venturesJesse explains the strategic fundamentals of scalable side hustles that can be built once and run independently versus labor-intensive service businesses.
Alex holds their own ▶ 10:35 Alex breaks down unit economics for local mobile dog groomingAlex demonstrates concrete operational knowledge by citing city demographic density, trailer capital expenses, hourly labor costs, and variable payback periods.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Alex as informed peer | Guest teaching | Guest disagreement | Alex pushing back | Why |
|---|---|---|---|---|---|---|
| Defining Side Hustles Versus Full-Time Ventures | 5 | 4 | 3 | 5 | Alex actively interrogates Jesse's definition of a side hustle, pointing out that Jesse's own portfolio ventures like Kahani and Growth Assistant initially resembled side projects before operators were hired. Jesse and Sophia clarify the difference between intentional full-time company incubation and true low-friction side projects. | |
| Brainstorming Profitable Side Hustle Ideas for 2023 | 6 | 5 | 5 | 4 | Alex pitches detailed ideas like a mobile dog grooming service with unit economics, but Jesse and Sophia immediately reject the framing, stating that a service-heavy operation with a three-year payback is a demanding business rather than a side hustle. Alex defends his definition around front-loading effort to reach five hours a week. | |
| Annual Self-Reflection and Goal-Setting Frameworks | 5 | 3 | 1 | 1 | The conversation is deeply collaborative and reflective as the co-hosts compare frameworks for end-of-year planning. Alex details his energy audit method, Sophia discusses her flight planner intentions and sitting in ambiguity, and Jesse shares his approach of focusing on habits over rigid goals. | |
| Startup AMA: Evaluating the ROI of Premium Domain Purchases | 6 | 4 | 2 | 3 | Alex introduces the AMA question regarding Acquire.com's $240k domain purchase, offering counterarguments regarding domain trust in low-trust industries like esports. Sophia and Jesse share experiential stories buying and selling domains and debate whether premium domains provide real ROI. |
Statements from this episode (13)
Lieberman: ConvertKit is super profitable and probably worth $300M
“ConvertKit had started as a side hustle that now obviously is a super profitable, probably, three hundred million dollar business”
Pujji: Side hustles are the least risky path to entrepreneurship
“And I think it's, if you can make that work, I think it's the best way to do it. Cause it's like the least risky by far.”
Amoruso: Sam Parr is building a $200M executive peer group business
“You know, what Sam Parr is trying to build in like a two hundred million dollar business. So and he's talked about that. It's not super under the radar anymore.”
Lieberman: Turning a business into a media brand unlocks ad monetization
“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, add dollars and not just the business.”
Lieberman: Thomas Frank makes roughly $150k monthly selling Notion templates
“Thomas Frank, the YouTuber, he shifted from having this like massive productivity channel that has two 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…”
Amoruso: Red Ventures' website playbook can be replicated with newsletters
“What Red Ventures did with websites someone can do with newsletters is just something really neat.”
Lieberman: Sequencing goals serially prevents ambitious teams from diluting focus
“One of, if I was to reflect on like the mistakes we've made over the years with morning brew, 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 th…”
Amoruso: It is okay for founders to take a year to make no decisions
“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.”
Amoruso: Founders often stay busy to escape unresolved personal issues
“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've got to deal with before we can rea…”
Lieberman: MicroAcquire surpassed $2.5M ARR with five years of runway
“I believe the business is north of, you know, 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.”
Pujji sold the AudienceGraph.com domain for five figures plus equity
“So I bought, like, adgraph.com, audiencegraph.com, like, I bought everythinggraph.com, and I got a ping from someone, and it was just like, hey, I want to, I'm starting a startup, and it's going to be called audiencegraph. Can I buy your domain? And I sold it …”
Amoruso: Inquire about domains anonymously to prevent sellers from inflating prices
“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.”