Podcast Summary: My First Million - "How I Made My First $1M – The Andrew Wilkinson Story"
Podcast: My First Million
Host: HubSpot Media (Sam Parr & Shaan Puri)
Guest: Andrew Wilkinson (Co-Founder of Tiny)
Date: July 5, 2024
Overview
In this episode, Sam Parr and Shaan Puri sit down with Andrew Wilkinson, the co-founder of Tiny, to unpack his journey from working as a barista to making his first million and beyond. Andrew details the distinct levels of financial and professional growth he experienced, dives into the mechanics and mindset transitions at each level, and shares lessons on money, business, happiness, and finding meaning. The conversation traverses moments of luck, decisions, mistakes, and reflections on what truly matters beyond accumulating wealth.
Key Discussion Points and Insights
The Four Levels of Wealth in Andrew’s Journey
Level 1: Escaping Low-Paid Work ($6.50/hr → $60/hr)
- Origin: Andrew was making coffee as a barista, dissatisfied and underpaid.
- Catalyst: Noticing two web designers enjoying a laid-back lifestyle prompted him to pivot.
- “Forget this. I don't want to make the espresso. I want to be drinking the espresso.” — Andrew (01:36)
- Action: Learned web design basics, sold his first website for $500 and unlimited pulled pork sandwiches (02:58).
- Significance: Early money represents freedom more than lifestyle—and this initial leap allowed Andrew to work on projects he actually enjoyed.
- “I was making a small amount of money for something I hated, and then I started making a large amount of money for something I would have done anyway for free. Like it was fun.” — Andrew (00:00, 03:14)
- Hosts relate: Both Sam (sold a small site for $24K and lived freely for a year) and Shaan (won a $25K pitch comp) experienced similar empowering early-money moments.
- “The early, early dollars and early freedom matter a lot more than the later dollars.” — Shaan (04:11)
Level 2: Self-Employed to Boss
- Realization: Found leverage by hiring others; first hired a programmer and profited by arbitrage (08:00).
- “In that moment I was like, oh my God, I just made $500 and I did absolutely no work. So that's that crazy transition of going from being a self-employed person, selling your time to being someone who can sell other people's time, which to me is like the big leverage point.” — Andrew (08:11)
- Learning: Delegation brings stress and mistakes at first—Andrew recommends the book The E-Myth (09:08).
- “My business is a machine and I'm the engineer and all the different people are widgets within the machine.” — Andrew (09:19)
- Breakthrough: Agency scaled, twelve staff, personal income topping $1M/year at age 23 (10:30).
- Pitfall: Consumerism phase—overspending on material things, which ultimately felt empty (11:25).
- Frameworks Introduced: Discussion of “E-S-B-I” progression from Rich Dad, Poor Dad (employee → self-employed → business owner → investor) (12:52).
Level 3: Serial Entrepreneurship & First Big Exit
- Diversification: Used profits to start numerous businesses (e-commerce, restaurants, blogs, SaaS, etc.), most failed, one succeeded.
- Viral Project: “Clients from Hell” blog goes viral—reflects the chaotic and experimental phase (14:38).
- First Big Exit: Sold Pixel Union (Shopify themes) for $7M (15:41), experiencing a “nest egg” moment.
- “I went to the ATM on the day it closed, and I checked my balance... I saw 3 million. It was like 3,100,000 or something like that on the chit. And I was like, I'm done. Like, I'm rich.” — Andrew (16:56)
- Shift: From relying on cash flow to building wealth (holdings, investments); strong influence from Warren Buffett.
- 20% Rule: Spent up to 20% of cash flow, invested the rest—allowed generous living without needing a major liquidation event (19:49).
Level 4: CEO to Investor (Post-Liquidity, Taking Company Public)
- Systematized Investing: Moved away from founding new companies to buying/owning, hiring CEOs, optimizing operations (22:58-24:10).
- Angel Investing: Invested aggressively (“maybe even $30M” in venture), with mixed, often unclear results; treats it mostly as “roulette” rather than “poker” (26:15, 28:31).
- “Angel investing is, frankly, a roulette table. You're just having fun.” — Andrew (28:31)
- Mindset: Realized being operator is a ceiling to scale—hiring world-class CEOs unlocked growth (24:10).
- Regrets/Learnings: In hindsight, wishes he had diversified more into “boring” assets, e.g., real estate, stocks (30:03).
- Transparency: Open about mistakes, luck, and wandering phases in the journey.
Reflections on Wealth, Happiness, and Meaning
The "Weight" of Money and Moving the Goalposts
- Counterintuitive lesson: More money doesn’t mean less anxiety or more happiness.
- “I'd reached the end, right? I think that's the goal that so many entrepreneurs think they want. And what I realized is even then with all that money in the bank, I was still anxious.” — Andrew (31:24)
- Core issue: Childhood scarcity made him equate money with peace—turns out, it imposes new isolation/stresses (32:53).
- Overshooting: Most people fixate on “billionaire” status or huge net worth, when there’s no functional difference in happiness or lifestyle after a certain point (33:46).
- “You have one belly and you can only eat so much food. Why do you need 100x that amount of food?” — Andrew (34:04)
Reverse-Engineering Life & Money
- Practical Framework: Determine your annual spending needs, multiply by 20 for a net worth target.
- “A million dollars, you can live an incredible life... If you want to fly private, add another million… So $60 million, if you've got it liquid... you can live an incredible life.” — Andrew (36:48)
- “Launchpad, Enough, Life’s Work” Model:
- Launchpad: Build to $250K/year in passive income.
- Enough: Reach your personally defined net worth.
- Life’s Work: Decide how to use your money/skills for meaning, purpose, fun (37:45).
Notable Quotes and Memorable Moments
On Early Money and Freedom
- “The early, early dollars and early freedom matter a lot more than the later dollars.” — Shaan (04:11)
- “If you have $24,000 ... you just denominate it in time. How many months of ‘freedom’ do I have?” — Sam (05:08)
On Delegation as Leverage
- “That moment I was like, oh my God, I just made $500 and I did absolutely no work.” — Andrew (08:11)
On Angel Investing
- “Angel investing is, frankly, a roulette table. You're just having fun… it’s a lot more kind of soulless than playing poker.” — Andrew (28:31)
- “If you talk to a lot of angel investors … did you really know?... a lot of people attribute skill to where there was luck.” — Shaan (29:09)
On Overshooting
- “Overshooting is a mistake that a lot of people make, myself included... you have one belly and you can only eat so much food.” — Andrew (33:46)
Life’s True Priorities
- “Business is a shared language … through that I can make friends. For me, like, my zone of genius is like building relationships with people. And so if I can build relationships with people and invest in their businesses or buy their businesses, I’m really happy doing that.” — Andrew (34:56)
Life Advice, Alternative Paths, and Parables
Deferred Life Plan
- Shaan shares an anecdote about a boss dismissing the “deferred life plan”—urging to pursue your purpose/headline goal NOW, not “after I make enough money.” (50:20)
- “If you know what you want to do, go do it. Don't wait for the perfect conditions.”
The Parable of the Fisherman and the Businessman
- Andrew retells the parable as a summary moral: Sometimes what you want is what you already have—and scaling up just to “retire and fish” later is circular if you already enjoy fishing today. (52:07)
Recommendations and Book Discussion
-
Andrew’s book, Never Enough, is strongly recommended by both Sam and Shaan for its honest, insightful writing and stories.
- “It’s actually a great book... I sat down and read the entire thing. Not because I was trying to be your friend, but because I thought it was awesome.” — Sam (53:58)
- They highlight three strong stories from the book: Charlie Munger meeting, Pixel Union sale/buyback, and the “dope” ending (54:21).
-
The book How to Get Rich by Felix Dennis is mentioned as another brutally honest look at the limitations and dangers of chasing wealth for its own sake. (44:52)
Timestamps for Key Segments
| Timestamp | Segment | |------------|--------------------------------------------------------------------| | 00:00–01:36 | Andrew’s first shift from barista to web design | | 02:32 | Selling his first website and getting paid in sandwiches | | 04:38 | Hosts reflect on their own "level one" moments | | 07:16 | Transitioning from self-employed to hiring and delegating | | 09:19 | The “business as a machine” E-Myth insight | | 10:26–10:47| First million in profit, age 22–23 | | 12:52 | The E-S-B-I framework from Rich Dad, Poor Dad | | 15:41 | Pixel Union sale for $7M, financial “nest egg” | | 19:49 | The 20% rule for spending/investing | | 22:58 | Moving from operator to owner (hiring CEOs) | | 26:15 | $25M–$30M angel investing: risks and lack of tracking | | 28:31 | Angel investing as “roulette,” lessons learned | | 31:21 | Wealth doesn't eliminate anxiety | | 33:46 | "Enough" is less than you think – the food analogy | | 36:48 | Reverse engineering your financial target | | 37:45 | Launchpad / Enough / Life’s Work | | 42:54 | Shaan reflects on classmates and the lack of a “blueprint” | | 44:52 | Felix Dennis’ How to Get Rich and dangers of wealth addiction | | 50:20 | The myth of the deferred life plan | | 52:07 | Fisherman/businessman parable, and optimizing for happiness | | 53:57 | Book plug: Never Enough |
Conclusion
This episode is a transparent, deeply insightful look at the makings—and misgivings—of entrepreneurial wealth. Andrew Wilkinson lays bare the incremental transformations he made from coffee shop to public company, candidly discussing lucky breaks, hard-won lessons, and the surprising ordinariness of life after “making it.” He, Sam, and Shaan challenge listeners to rethink how they frame money goals, distinguish between happiness and ambition, and consider what truly constitutes life’s work. The episode is both roadmap and cautionary tale for anyone on a quest for their own “first million (and beyond).”
Book: Never Enough by Andrew Wilkinson
Recommended Reading:
- How to Get Rich by Felix Dennis
- The E-Myth by Michael Gerber
- Rich Dad, Poor Dad by Robert Kiyosaki
Note: All promotional content and ad reads skipped per instructions.