My First Million – Andrew Wilkinson: The Hardest and Easiest Businesses to Start

Date: November 17, 2022
Hosts: Shaan Puri, Sam Parr (not present), Chris
Guest: Andrew Wilkinson
Main Theme:
Shaan and Chris sit down with Andrew Wilkinson (founder of Tiny) to discuss the spectrum of businesses from hardest to easiest to start, lessons from buying, selling, and building companies, and the nature of trends and fraud in internet entrepreneurship and investing.

Episode Overview

Andrew Wilkinson returns to reflect on his entrepreneurial journey, sharing postmortems on businesses he’s started, acquired, or shut down. The episode covers:

• What makes certain businesses “easy” or “brutal”
• The difference between “operator” and “investor” mindsets
• Cautionary tales from owning brick-and-mortar and SaaS businesses
• The problem with copying “smart money”
• Insights on recent crypto/venture debacles (FTX, Bird, eSports, etc.)
• Launch of his investment banking venture for founders

The tone is candid, practical, and reflective, filled with stories, sharp insights, and good-natured roasting.

Key Discussion Points

1. Hardest vs. Easiest Types of Businesses

[00:00–03:50]

• Hardest: Brick & mortar, physical goods, and people-intensive businesses:
  • “The hardest possible businesses are brick and mortar or where you have to move physical goods and you have a lot of employees.”
    – Andrew Wilkinson [00:15]
  • Owns a bakery/deli: constant headaches, coordination issues, thin margins, people dependent, vulnerable if a few people call in sick.
  • Restaurants, e-commerce with inventory = “brutal, brutal businesses.”
• Medium: Agencies (e.g., service-based businesses)
  • Andrew ranks agencies as “medium” difficulty due to asset-light nature and ease of scaling staff, but feast/famine cycles and supply/demand balancing are tough.
• Easiest: Digital, asset-light, recurring revenue businesses
  • Job boards (e.g., WeWorkRemotely): small team, automatic revenue, grew hugely from strong SEO and simple best practices.
  • "The easiest business that I own is a company called WeWork Remotely ... with a very small team, we were able to build it into a very large business."
    — Andrew Wilkinson [27:31]
• SaaS: Treacherous unless you’re fighting giants:
  • Lost $10M on Flow (project management SaaS): "Competing against [Asana], it’s like Fiji fighting the United States ... So I lost 10 million dollars doing that. Incredibly painful."
    — Andrew Wilkinson [28:41]

2. Learning from Failures: Postmortems on Past Ventures

[02:30–29:15]

Pixel Union Story:

• Accidental business with enormous upside (Tumblr/Shopify themes).
  • “My first taste of automatic revenue ... I would go to sleep and I’d wake up and we would have sold, you know, 500 bucks worth of these Tumblr themes.”
    — Andrew Wilkinson [05:54]
• Sold for $7M in 2014, heavily regretted not understanding how to value a fast-growing business.
  • "I thought it was great to get a 14x multiple, but not when it’s growing that fast. So I regretted it."
    — Andrew Wilkinson [08:08]
• Bought back for $26M, took it public ("WeCommerce") at a $260M+ valuation.
  • Takeaway: “You can go from literally the bottom to the top in less than a decade if you get obsessed and put in the work.”
    — Shaan [10:00]

Cat Furniture eComm (HJ Muse):

• Lost $300K; learned how e-commerce can have deceptive, razor-thin margins and constant reinvestment in inventory. "I ended up shutting that business down and losing ... all the money I put into it. But, but it was a great lesson in just hard businesses."
  — Andrew Wilkinson [23:01]

Restaurant Lesson (Famous Original):

• Hubris led him and friends to open a bar/pizzeria—total disaster due to build-out cost overruns, poor management, labor shortages.
  • "We learned it was the most brutal business in the entire world. And we were shocked by how much money we could lose."
    — Andrew Wilkinson [31:33]

3. The Operator-to-Investor Transition & Warren Buffett Lessons

[10:53–16:37]

• Reading Buffett changed his thinking about capital allocation and operational insight.
  • Buffet’s Seas Candy letter: detailed, design-oriented, and nuanced operational feedback. Not just about financial efficiency but about controlling narrative, details, customer experience.
  • "[Buffett] actually was someone who, yes, he owned the businesses, but he influenced the businesses massively and he made them grow."
    — Andrew Wilkinson [15:12]
  • Munger: “I’ve never been able to change someone’s mind ... CEOs are not puppets. They have their own brains.”
    — Charlie Munger (relayed by Wilkinson) [15:35]

4. Case Study: Coffee Culture & AeroPress Acquisition

[17:30–22:30]

• Acquired AeroPress—iconic coffee gadget with massive cult following, but neglected online/DTC sales. Hired SodaStream USA’s ex-president to grow it.
  • “When do you get the opportunity to buy a way of making coffee? It’s like, how do you value buying Kleenex?”
    — Andrew Wilkinson [18:28]
  • “If something becomes a verb, just invest.”
    — Shaan [19:10]

5. Brainstorm: New Ideas & Sniper Advertising

[34:01–36:57]

• Andrew floats the idea for an “advertising sniper rifle”—a concierge service to target one VIP everywhere on the web: "If someone sees you five times, they think you’re everywhere."
  — [34:23]
• Chris’s friend Jack Smith famously did this to get into AngelPad incubator by targeting its founder with custom LinkedIn ads, leading to an $800M outcome [35:03–36:20].

6. Building a 'Tenzing'—Investment Banking for Founders

[37:13–42:25]

• Launching Tenzing, a modern “investment bank for founders,” to help with small exits, capital raises, and “financial translation” for operators.
  • “I have been looking for a firm for years that I can use to either sell small businesses ... or help founders do secondaries ... And I’m yet to find someone.”
    — Andrew Wilkinson [37:25]
• Most founders don’t speak investor lingo, missing out on opportunities like R&D credits, bank lines, or M&A.

7. Lessons from Venture, ‘Smart Money’, and Fraud

[45:26–83:48]

• Crypto Disillusionment (“FTX saga”):
  • “I think it’s really, really bad for crypto ... when the number two ... that’s the equivalent of JP Morgan going out of business and everyone losing their money.”
    — Andrew Wilkinson [45:44]
  • “There’s always a second chance on the train.”
    — Kevin Van Trump (quoted by Shaan) [47:27]
• Public Markets & Legalized Stealing:
  • Small-cap IPOs in Canada often dress up “corner store”-scale companies as hot trends, fleece retail investors, insiders exit with millions—“basically legal stealing.”
    — Andrew Wilkinson [55:59]
  • EG: eSports, Canadian stock EGLX, Bird Scooters, Nikola Motors (rolling truck fraud), venture SPACs.
• On Venture Capital & Rigged Incentives:
  • Management fees guarantee VCs make money even if investors lose. By the time results are in, partners have “already made hundreds of millions of dollars.”
    • “They win no matter what … we don’t do any management fees whatsoever because I am allergic to this. I find it really gross.”
      — Andrew Wilkinson [73:36]
  • Warns about copying “smart money”:
    • “Just because this really smart person who you respect [...] is in something, you can’t outsource your conviction.”
      — Shaan [82:28]
  • Andrew echoes: Just buying stocks because Howard Marks did without understanding full context is a losing game.

Notable Quotes & Memorable Moments

• “If you were willing to put in a decade, you can go from literally the bottom to the top, and that’s pretty cool.”
  — Shaan [09:59]

• “Entrepreneurs are the people that do the work. The investors are people that shuffle paper around on Wall Street ... What I realized with Buffett is that he ... influenced the businesses massively and he made them grow.”
  — Andrew Wilkinson [15:12]

• “Dude, it’s so boring. That’s why ... I start more businesses. It sounds like luxury when you’re a stressed entrepreneur, but actually doing it in practice ... you don’t get your hands on the tools.”
  — Andrew Wilkinson [16:33]

• “Competing against Asana ... it’s like Fiji fighting the United States. And I’m going, ‘I’m going to win this!’ Ridiculous.”
  — Andrew Wilkinson [28:41]

• "Grass is always greener. Every agency owner I know wants to own a SaaS company. Every SaaS founder wants to own a consulting company ...”
  — Andrew Wilkinson [27:06]

• “If something becomes a verb, just invest.”
  — Shaan [19:10]

• “If you don’t create the billion-dollar business, then I lose all my money. Right?”
  — Andrew Wilkinson [62:34] (on VC terms)

• “Just because this really smart person who you respect ... is in something, you can’t outsource your conviction.”
  — Shaan [82:28]

• “They win no matter what ... I’m allergic to this. I find it really gross.”
  — Andrew Wilkinson [73:36] (on 2% fund management fees)

Timestamps for Important Segments

• [00:15] – Ranking business models from hardest to easiest
• [05:54] – Pixel Union origin and exit story
• [08:08] – Lessons from selling too early & learning value investing
• [15:12] – Warren Buffett’s “operator” side & influence on Andrew
• [17:30] – AeroPress acquisition: why it’s unique, the power of brand
• [23:01] – Losing money in e-commerce (cat furniture)
• [27:31] – Job boards as an easy business—WeWork Remotely
• [28:41] – Losing $10M on SaaS vs agencies vs services
• [34:01] – Sniper targeting as a new business idea
• [37:13] – The 'Tenzing' founder banking idea
• [45:44] – FTX and the problem of trust in crypto markets
• [55:59] – Fraud and legal fleecing in Canadian small-caps
• [62:34] – Non-binary term sheet: innovation in startup funding
• [73:36] – The “rigged” structure of VC management fees
• [82:28] – The myth of “smart money” and the importance of independent judgment

Final Takeaways

• The choice of business model matters immensely: Seemingly “simple” businesses can be brutally hard; recurring digital revenue models, though competitive, can scale smoothly.
• Lessons come from pain as much as from success—and often the costly ones are the most valuable.
• Don’t blindly follow “Smart Money”: Even elite investors make bad bets, sometimes with misaligned incentives.
• Self-education compounds quickly: Wilkson’s story is proof that obsession, learning, and reflection can propel a founder from rookie to industry leader within a decade.
• Alignment and incentives matter: From structuring deals to picking partners, dig deeper beyond surface appearances.
• Entrepreneurship isn’t one-size-fits-all: Many founders stray onto the wrong path (e.g., chasing VC with non-VC businesses) and regret it later.

For more, find Andrew Wilkinson on Twitter @awilkinson and check out Tiny and his new venture, Tenzing. This episode is packed with practical, painful, and sometimes hilarious entrepreneurial wisdom—a worthwhile listen for anyone building or buying businesses.