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My First MillionAndrew Wilkinson: $100M Yacht Party, Recent Investments & More Billionaire Sh*t (#488)
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CHAPTERS
- 0:00 – 4:49
Roasting Banter and Health Kicks
The hosts open by teasing Andrew about his hair and welcoming him back after his strep throat. The talk moves to muscle-gain competitions, Ozempic, and Shaan's reluctance to depend on anything.
- •Sam jokes that Andrew looks like the mom from Home Alone
- •Andrew had strep throat and rescheduled the recording
- •Andrew is in a muscle gain competition with friends and wants to look like Wolverine
- •Shaan avoids caffeine and weight-loss drugs because he wants the win to be his own
- 4:49 – 8:46
Jesse Itzler and Building Life Around What You Love
The conversation turns to Jesse Itzler's string of passion-driven ventures, from jingles to Marquis Jets to Zico. Andrew says building a business around what you love is great but can be a double-edged sword.
- •Shaan recaps Itzler's path: jingles, Marquis Jets sold to NetJets, Zico coconut water
- •Itzler is currently hunting for a pickle company to buy
- •Andrew admires people like Nick Gray who build their lives around what they enjoy
- •Andrew warns that turning a hobby into a business can take the joy out of it
- 8:46 – 17:13
The $29 Twitter Subscription Experiment
Andrew explains how he used paid Twitter subscriptions to filter his overwhelming DMs and ended up with a real revenue stream. Shaan shares his conspiracy theory that Andrew is trying to befriend Elon Musk, which Andrew denies.
- •Open DMs brought about 100 messages a day, mostly scams, so he gated access behind a $29 subscription
- •About 550 subscribers means roughly $16K MRR, or $200K a year, for an hour or two a month
- •He frames a 1–5% conversion on 240,000 followers as a business worth $5–15 million
- •The group has produced deal flow and a few hires
- •Andrew says he doesn't know what he'd say to Elon and wants to meet Larry Ellison
- 17:13 – 21:40
Rejection, Status, and Talking to Rich People
Shaan describes a famous person who hadn't felt rejection in seven years, and the group discusses how status shapes social settings. Andrew shares his approach of asking people questions about themselves.
- •Shaan says some people in LA are out of touch with rejection
- •Andrew says status depends on the room you're in, including when it comes to dating
- •Andrew uses the Dale Carnegie approach of asking questions to get past status anxiety
- •Sam and Shaan describe how Ben leaves meetings with people loving him after saying almost nothing
- 21:40 – 28:03
The $100 Million Yacht and the Endless Status Game
Andrew describes being invited onto a yacht owned by a billionaire worth $20 billion plus, which he found oddly unappealing. The group reflects on how status has no endpoint, with stories of lifestyle-business snubs and a standoffish NBA minority owner.
- •Andrew compares the yacht to a very nice RV: amazing, but not as nice as a Four Seasons at 100 times the cost
- •A $100M+ yacht costs $10–20 million a year to maintain, with 30 staff for 10 guests
- •A public company CEO on the yacht dismisses Andrew's $800 million company, echoing an earlier VC who called his business a lifestyle business
- •A multi-billionaire told him his only gap with a $20 billion peer was a super yacht
- •Shaan tells of an NBA minority owner who turned his volume down just halfway during their introduction
- 28:03 – 34:57
Why MetaLab Makes So Much Money
Asked how the agency division generates so much profit, Andrew credits a long-held niche in product design and inbound demand. He describes how overflow leads were used to spin up a constellation of smaller agencies.
- •MetaLab owned product design and MVPs for startups starting in 2007, so clients pay a premium
- •Demand is mostly inbound, with only six or seven salespeople in a company of about 150
- •MetaLab was the golden goose that funded Tiny and its other acquisitions
- •Overflow leads fed smaller agencies like 8020, one of which now makes $2–3 million of EBITDA
- •Sam reads public figures: about $81 million in revenue and about $20 million in operating earnings in 2022
- 34:57 – 40:28
One Plus One Equals 100 and Launchpad Businesses
The group discusses Andrew's one-plus-one-equals-100 framework, using Syed's WP Beginner, Nick Huber, and Shaan's Shepherd deal as examples. Andrew says he'd start a design agency if he lost everything, and Shaan contrasts the easy mode of promoting a product with his hard-mode ecommerce business.
- •Agencies are lumpy, high-stress businesses but can be great cash-flow engines
- •Andrew says an agency is the easiest way to make $500K a year, though AI may change that
- •Nick Huber acts as a human router for inbound inquiries
- •Shaan describes his Shepherd deal as doubling revenue without operational load
- •Andrew calls these low-glamour businesses launchpads for what you really want to do
- 40:28 – 43:54
Buffett's Hands-On Research and the Boredom of Annual Reports
Sam shares stories about Warren Buffett personally testing investments, like visiting Disney and pacing out real estate. Andrew and Shaan admit that Buffett-style reading is far more tedious than it sounds.
- •Sam says Buffett visited Disney's theme park and knocked on Geico's door to research them
- •Shaan sees Buffett as business abstracted to the ultimate degree
- •Andrew wants enough of Buffett's approach to have freedom with his time
- •Andrew and Chris lasted about four hours reading printed annual reports when starting Tiny
- 43:54 – 51:58
No Story Lost, Scribe, and Andrew's Book
Andrew describes No Story Lost, a premium biography version of Storyworth, and the group discusses the ghostwriting company Scribe. Andrew then explains his motivations for writing a book about building Tiny and the idea that it's never enough.
- •No Story Lost has biographers interview your parents, and Andrew invested $25K
- •Shaan sees AI cutting the writer's workload on such services by 50–80%
- •Scribe went bankrupt and was reportedly bought by Enduring Ventures
- •Andrew's draft is with the publisher, with release expected in 2024
- •He wants to explore why everyone always wants more
- 51:58 – 1:04:25
Routines.club and Maui Nui Venison
Andrew describes two businesses he likes: Routines, an affiliate-driven site that breaks down successful people's daily habits, and Maui Nui, which sells FDA-approved axis deer meat from Hawaii. Sam and Shaan joke about the deer and debate the business's scalability.
- •Routines.club profiles days of people like Huberman, Ferriss, Attia, and Andrew, earning $30K+ a month in affiliate revenue
- •Maui Nui sells meat from invasive axis deer and spent about seven years getting FDA approval
- •Andrew says the venison has higher protein content than salmon or beef
- •Sam worries about scaling and raises health-nut skepticism of meat brands
- •Shaan frames such investments as a portfolio of interesting things, and Andrew counters with the Athletic Greens example
- 1:04:25 – 1:07:03
The Ethics of Eating Meat
A debate over ethically sourced meat grows out of the Maui Nui discussion. Andrew sees a spectrum from industrial farming to humane hunting, while Shaan argues it is still killing for pleasure.
- •Andrew calls industrial meat concentration camps for animals
- •He says he feels fine eating an animal that lived a great life
- •Shaan calls himself a hypocrite who still eats meat but says ethical killing is still killing
- •Andrew predicts people will look back at eating meat with shock in 100 years
- •Sam describes killing his own turkey, which tasted bad
- 1:07:03 – 1:16:45
Running Hampton: Community Risks and the Moat
Andrew asks Sam what makes Hampton hard to run, and Sam says the main risk is admitting too many people too quickly. They compare it to EO, YPO, Vistage, and On Deck, and discuss Hampton's logistics and its free customer acquisition advantage.
- •Sam says Hampton can't scale like software and the main risk is letting in too many people too fast
- •Feedback loops are slow and there is no MVP for a retreat
- •Andrew left EO because of a few members he didn't want to spend time with, and now runs four forums himself
- •On Deck is cited as a cautionary example that raised venture and scaled too quickly
- •Andrew argues Sam's audience gives Hampton a huge competitive advantage and a negative cash conversion cycle
- 1:16:45 – 1:29:16
Profit First, Dividends, and Spending 5% of Income
Andrew explains the Profit First method and why he wants CEOs to eat from a smaller plate, and why he pushes dividending cash out of businesses. He shares that he spends at most 5% of what he earns and invests the rest, while Shaan and Andrew discuss focusing on big financial levers.
- •Profit First sets aside the target profit margin the day revenue arrives
- •Andrew doesn't make Tiny's CEOs use it but sent them the book, and prefers businesses hold only a month or two of cash
- •Tiny acts as the bank for its subsidiaries if they need cash
- •He aims to spend about 5% of his income and invest the rest, and says people should let themselves live well
- •Shaan and Andrew agree on focusing on large levers like income rather than small expenses
- •Andrew misses Buyer, the negotiation-as-a-service business sold to Ramp for cash
