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My First MillionAndrew Wilkinson's $20,000 to $260,000,000 story (#521)
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CHAPTERS
- 0:00 – 2:13
Episode Preview and Guest Introduction
Sam previews the episode and introduces Andrew Wilkinson and his holding company Tiny. He teases the Profit First discussion, Andrew's experience with Peter Attia, and how he shot his shot with heroes like Bill Ackman and Charlie Munger.
- •Andrew owns Tiny, which grew from an agency's profits into roughly 18-20 acquired companies and a public listing
- •Sam says the Profit First segment is something he will take back to his own business
- •Preview of Peter Attia and spending behind the scenes
- •Preview of how Andrew got into rooms with Ackman and Munger
- 2:13 – 12:27
Business on Hard Mode vs. Easy Mode
Andrew explains that sexy businesses like a bakery are hard ways to make a living, while boring lever pulls pay off. He contrasts the bakery with We Work Remotely, and Shaan shares a similar Birthday Alarm lesson about raising prices and a Stripe checkbox.
- •Price increases, shipping savings, SEO affiliate revenue and T-bill interest are unsexy but big wins
- •The deli and bakery is complex and might make about 150 grand a year
- •We Work Remotely, bought for about 1.5 million, went from 400K profit to roughly 4 million EBITDA with a tiny team
- •Shaan's Birthday Alarm gained from a 30% price rise and Stripe's card-updater feature
- •Effort and result are far more disconnected than people think
- 12:27 – 19:56
Profit First: Sweeping Profit Before Expenses
Shaan explains the Profit First idea of moving profit out of the company first, and Andrew adds the smaller-plate analogy. They discuss how much cash to leave in a business and why it forces discipline in spending.
- •Profit is swept out first so expenses must be paid back from what's left
- •Smaller plate analogy: people spend more thoughtfully with less
- •Andrew leaves roughly two to four weeks of payroll and expenses, since Tiny can inject cash if needed
- •Some businesses can run at 80-90% net margins, but dreamer CEOs burn the cash
- •Sam and Shaan both plan to change how they handle cash
- 19:56 – 24:44
Incentives: Dinner Guests, Realtors and Stink Bids
A friend's quote about dinner guests always saying steak leads into how CEOs spend other people's money. Shaan and Andrew share stories of realigning a realtor's incentives, and Sam describes friends who tour homes and lowball constantly.
- •CEOs with small bonuses don't feel every dollar the way an owner does
- •Shaan gave his agent 15% above the asking price plus a silly penalty
- •Chris paid a realtor $1,000 per stink bid offer sent
- •Everything comes down to incentives, and on-paper incentives may not be enough to change behavior
- 24:44 – 28:40
Acquisition Funnels and Sending LOIs
Sam points out that buying companies is a sales job with a tiny conversion funnel. Andrew says Tiny relies on reputation and inbound, and explains how he filters sellers early and sends LOIs freely.
- •A friend's firm looked at 1,000 companies and closed about 18
- •Andrew says Tiny prefers a public presence so sellers seek them out, which Sam calls marketing instead of sales
- •Shaan says his funnel is tiny and he may do one deal or none in a year
- •Andrew asks three screening questions, then gives a price early by email
- •LOIs are non-binding and taken seriously, so they are sent constantly
- 28:40 – 31:34
The Private Jet Story
Sam tells how he first met Andrew when Andrew flew him on a private jet to Vancouver to discuss buying The Hustle. They joke about the wooing and the timing before Sam's wedding and eventual HubSpot sale.
- •Sam was down on himself and the business when approached
- •His first private flight included champagne and the Wall Street Journal
- •Andrew says it's the only time he has done it for someone
- •Sam sold to HubSpot later
- 31:34 – 38:33
Shooting Your Shot: Dan Gilbert, Ackman and Munger
Shaan asks how Andrew builds such a network. Andrew describes cold emailing Dan Gilbert, bidding $57,000 for a charity lunch with Bill Ackman, and writing letters to Charlie Munger.
- •Cold email to Dan Gilbert got a reply in 20 minutes and a tour of Detroit
- •Ackman passed him to a board member, so Andrew bid $57,000 for a charity lunch
- •Ackman later invested in a deal with Tiny
- •Munger prefers letters to be remembered, then talks by phone
- •Shaan notes Andrew checks his ego and is willing to spend money on relationships
- 38:33 – 44:06
Crashing the Oscars Afterparty and Earning the Room
Andrew explains how going to TED worked because he belonged, then tells the story of attending the Oscars and Vanity Fair afterparty through Myria. He concludes you should earn your way into a room rather than buy your way in.
- •He worked his way into TED by designing the TED app
- •Myria helps people turn money into an interesting life and arranged his Oscars trip
- •At the Vanity Fair party, people lost interest when he said he was in tech
- •He had no shared language or value to offer there
- •Shaan sums it up as earning the room you're in
- 44:06 – 47:29
Myria, Concierge Services and the Business of No
The hosts discuss Myria's pricing and whether it can be a venture-scale business. Shaan describes a business built around people who no longer hear no.
- •Andrew invested in Myria's angel round but is unsure about venture scale
- •Services charge around 25 grand plus a cut of spending
- •An invite-only reservations service makes you lose access if you don't use your invite
- •Shaan says successful people rarely hear no, so products give them something to lose
- 47:29 – 50:21
Peter Attia as Your Doctor
Andrew describes waiting about three years to become a patient of Peter Attia and the psychological test he went through. He discusses the cost and the value of the team approach.
- •Attia's practice has a long wait list and a psychological screening
- •Attia worried about Andrew's follow-through, which made him a dream patient
- •The cost is hundreds of thousands of dollars
- •The team caught cholesterol issues, but Andrew calls it a crazy use of money for most people
- 50:21 – 54:30
Be the Barnacle on the Whale
Andrew explains how owning a business with free marketing is powerful and recounts building Shopify themes that rode Shopify's growth. The business went from a $20,000 start through a sale and buyback to a $260 million public listing.
- •Marketing often costs 15-30% of a business, so free distribution lifts margins
- •Shopify asked him to list themes in its marketplace, giving free traffic
- •He saturated the early marketplace and the business grew with Shopify
- •Started with about $20K, sold for about 7 million, bought back for 25 million and listed at $260 million
- •Andrew suggests looking at less saturated ecosystems such as Discord
- 54:30 – 57:14
Selling and Buying Back the Business
Shaan asks why Andrew sold and then paid far more to buy back. Andrew explains burnout, financial insecurity, and reading about Buffett's moats after selling.
- •He ran several businesses and hit a wall with burnout
- •Selling gave financial security after years of borrowing from Peter to pay Paul
- •Reading about competitive advantage made him realize he sold a great business
- •He stayed on the board and offered a deal when the buyers got fatigued
- •Total investment was about 36 million including M&A
- 57:14 – 1:06:58
People Suffer in Silence and People Don't Change
Andrew explains that CEOs left alone often fester in silence and assume silence means malice. The group then debates whether people change, with Shaan suggesting you should assume they won't.
- •Tiny's autonomy culture means some CEOs feel forgotten without check-ins
- •Hanlon's razor: don't attribute to malice what ignorance can explain
- •Andrew says people rarely change except by hitting rock bottom, and double down when challenged
- •Shaan reframes it as assuming people don't change rather than a rule
- •Sam wraps up by saying he'll act on the Profit First idea
