Story
The tax-day wake-up: investments earned more than the grind
Nick Gray netted ~$350K in one of his hardest business years, then his accountant pointed out he'd made more from passive investments. The moment made him reconsider how he spends his time.
“And I think maybe we netted out like $350,000 profit. And it was one of the hardest years of my life, honestly, for a variety of staffing reasons and other things. And as I was doing my taxes, My accountant said like, oh wow, do you realize you made like so much more money from your investments than you did from your business?”
Framework
The $10M exercise: most of what you want costs way less
Nick Gray shares a Tony Robbins exercise: ask what you'd do differently with $10M, get specific, then realize most of those things only need ~$1M. It reframes money as a tool for a specific life, not an open-ended chase.
“Now, Sean may know this. This is a Tony Robbins exercise that he's done either at Business Mastery or UPW. And the gist, I'll forward you to the end, is that the vast majority of things we say that we would do differently at $10 million, actually, you only need a million dollars to get there.”
Steal thisAsk yourself what you'd do with $10M, get hyper-specific on each item, then price out the real cost — most of it needs a fraction of what you think.
Idea
Babe the Bounty Hunter: contingency-fee matchmaker for the ultra-rich
Nick Gray pitches a matchmaking service for top-tier clients ($50M+ net worth, 5M+ followers) charging zero upfront and only a 7-figure success fee on marriage. Most matchmakers refuse contingency and only take retainers.
“I am going to do potentially, if enough people ask me for this, the first 7-figure millionaire matchmaker that is only based on a contingency fee. So I'm going to have no cost. I'm only going to take the top of the top clients. We're talking people like, um, I'm not going to name names, but, but folks that have a minimum, probably $50 million net worth, 5 million social followers.”
Steal thisOffer elite matchmaking with no retainer — only a million-dollar handshake success fee paid on marriage.
Number
Matchmaking runs about $5,000 per date
Nick Gray explains high-end matchmaking services range from $5,000 to $100,000, working out to roughly $5,000 a date with extensive pre-screening — and PE firms like buying these businesses.
$5K
Cost per matchmaking date · USD/date
“But matchmaking services can go from $5,000 all the way up to $100,000. And the ones that I have heard of, it's, it's roughly a thou— or sorry, it's roughly $5,000 a date. And they set you up and they extensively prescreen these women.”
Story
Built a multimillion-dollar business as a solo museum tour guide first
Nick Gray made the case for simple, hands-on starts: he personally led Museum Hack tours every Friday and Saturday night for two full years before hiring anyone, turning a tour-guide gig into a multimillion-dollar company.
“I built a multimillion dollar business out of being a tour guide. Every Friday and Saturday night, I was literally leading people at the museum. And I did that for 2 years before I even hired my first person.”
Idea
Run local tours as a side hustle on Airbnb Experiences
Nick Gray pitches signing up on Airbnb Experiences to lead tours of your own town for pay. It works in tier 1 and tier 2 cities — show locals your favorite spots, beg for 5-star reviews, and you've built a side hustle.
“Airbnb Experiences. If you are interested in starting a new side hustle, you can sign up on Airbnb Experiences to lead a tour in your town and charge people for it. This is a way for you to immediately start to get money from people searching for cool things to do. Now, this only works in major towns where they've launched Airbnb Experiences, but it's generally tier 1 and tier 2 cities.”
Steal thisList a tour of your own city on Airbnb Experiences and start collecting 5-star-driven bookings this weekend.
Story
He SEO-hacked Equinox pools to get his swim lane back
Nick Gray blogged a hard-to-find list of NYC Equinox gyms with pools, ranked #1, then his pool got crowded with 50-100 visitors a day. So he edited his blog to say the pool was 'closed for maintenance' for a year to thin the crowd.
“And I'm getting 50, 100 visitors a day to this page. And so I, uh, closed my gym swimming pool according to my blog for maintenance for a year so that I would have to wait for less people. And people would say, hey, they'd go there, they'd say, hey guys, sorry, this pool's closed for a year.”
Framework
Publishing online is an invitation for serendipity
Nick Gray recounts how blogging about obscure topics (a hedge funder, a French cruise ship's art panels) led to a personal call from the subject and an inquiry from the Met. Publishing your interests online compounds into unexpected connections over the long term.
“All of this is through publishing and living your life online. These are little moments of when I've done that, that have paid off for me in the long game. It's important to know this didn't happen overnight. This is a long-term investment.”
Steal thisPublish your niche interests publicly and consistently — each post is a long-game invitation for serendipity.
Tactic
The value-additive intro: end with everyone sharing a tip
Nick Gray's advanced party move: about an hour in, do a round of intros where each person's answer benefits the room — a local pro tip or a great piece of media they consumed. Guests leave with new ideas and feeling better than when they arrived.
“And this is what I call a value-additive intro. Value-additive means that everybody's answer adds to the benefit of the room. And so for Sam, for example, who lives in Connecticut now, say that he was hosting this in Westchester, you would say, hey everybody, we're going to do our last round of icebreakers.”
Steal thisEnd your event with a round where each guest shares one local tip or great recommendation — value for the whole room.
Framework
Hosting events is the fastest way to become interesting
Nick Gray's core thesis: interesting people want to meet people doing interesting things, and the fastest route is to host your own cheap events (under $100 each). The network from hosting launched his multimillion-dollar Museum Hack.
“I found that interesting people want to meet people that are doing interesting things and the fastest way to become interesting was for me to host my own events. So we talked before about those business ideas that you don't need a lot of capital for. Hosting events is kind of the same way. You can do it with very little money. Each party should cost you less than $100.”
Steal thisHost small recurring events (under $100 each) to build the network that launches your next business.
Framework
The NICK Method for hosting a party
Nick Gray's named playbook for a 2-hour gathering: N = name tags (first name, block letters), I = intros/icebreakers, C = cocktails or mocktails only (no dinner party), K = kick 'em out at the end while people still want more.
“The NIC method, N-I-C-K, N is name tags, I is intros, C stands for cocktails or mocktails only. Do not do a dinner party. I talk about why dinner parties are a recipe for failure for new first-time hosts. And K stands for kick 'em out at the end. This is only a 2-hour gathering. You want to keep it tight. You want people to leave when they're wanting more”
Steal thisRun any party on the NICK method: name tags, intros, cocktails only, kick 'em out after 2 hours.
Story
Museum Hack: $2M/year giving 'fuckin awesome' museum tours
Sam's friend Nick Gray built Museum Hack into a ~$2M/year business giving fun, unconventional guided museum tours across ~6 cities (corporate clients included), then sold it — without being an art expert.
“And so he built this business that was making $2 million a year in sales. And you would pay him, or eventually he would train people in a variety of cities and you would pay $50 to $100.”