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My First Million

I Ranked the Best & WORST Businesses to Start Before 2026 | Andrew Wilkinson

with Andrew Wilkinson

Published November 7, 2025
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About This Episode

The host and Andrew Wilkinson play a "tier list" game ranking different business models by their median successful outcome, lifestyle impact, upside, and difficulty, drawing heavily on Andrew's two decades of experience running agencies, buying companies, and managing capital. They discuss models such as MLMs, freelancing, agencies, SaaS, marketplaces, restaurants, content creation, real estate, hedge funds, angel investing, and buying local "sweaty" businesses, while also unpacking how Tiny was built and why its stock chart can be misleading. In the second half, they shift to psychological themes like the courage to be disliked, identity boxes, contrarian thinking, and designing a career around work you enjoy doing thousands of times rather than chasing labels or external approval.

Topics Covered

Entrepreneurship Investing Content creation Personal development Identity Risk and uncertainty Venture capital Private equity Relationships Storytelling

Disclaimer: We provide independent summaries of podcasts and are not affiliated with or endorsed in any way by any podcast or creator. All podcast names and content are the property of their respective owners. The views and opinions expressed within the podcasts belong solely to the original hosts and guests and do not reflect the views or positions of Summapod.

Quick Takeaways

  • Andrew and the host rank business models by median successful outcome, lifestyle quality, upside potential, and likelihood of success, rather than by extreme outlier wins.
  • MLMs are rated F-tier because they rely on recruiting new participants rather than genuine product value and often collapse or attract legal trouble.
  • Freelancing and owning a few Airbnbs are seen as D-tier, restaurants as E-tier, and most agencies and marketplaces as C-tier due to lumpiness, difficulty, and competition.
  • SaaS is rated B-tier overall, but niche, mission-critical vertical SaaS with high switching costs and hardware integration (like Serato for DJs) can be exceptional.
  • Owning real estate is rated C-tier because of ceilings on rent, heavy capital needs, and illiquidity, despite being a solid, predictable way to build family wealth.
  • Permanent-capital vehicles like Berkshire Hathaway or Pershing Square are rated S-tier, while typical hedge funds are B-tier and angel investing for normal people is E-tier.
  • Andrew argues it's often better to buy already-working "sweaty" local businesses and improve them than to start many new ones, reflecting on how he burned millions on failed startups before switching to acquisitions.
  • He explains that Tiny grew from roughly $4-5 million of seed capital into a public company with about $250 million in revenue, $65 million ARR, over $40 million of EBITDA, and a $200 million fund, despite a declining stock chart.
  • They explore the idea of "the courage to be disliked," identity boxes, and how people act as "prison guards" when others step outside their expected roles or industries.
  • The host and Andrew advocate being jealous of other people's inputs (how they spend their days) instead of their outputs, and designing careers around work you would gladly do thousands of times.

Podcast Notes

Cold open and Tiny financial snapshot

Headline numbers for Tiny and its fund

Current revenue, ARR, and EBITDA across Tiny[0:06]
• Andrew says they have $65 million of ARR, over $40 million of EBITDA, and manage a $200 million fund, putting them at over $300 million in revenue across 30 businesses, with all fund businesses profitable.
Andrew's reaction to being perceived as "failing"[0:14]
• He jokes that if those numbers count as failing, he wants to sign up for that kind of failure.

Introduction and tier-list game setup

Reintroducing Andrew and framing the episode

Andrew as a frequent guest[1:11]
• The host notes that Andrew is one of the most visited guests on the podcast and says it is always good to have him.

Overview of Andrew's business experience

Variety of businesses Andrew has run[1:29]
• The host lists that Andrew has done agencies, private equity, e-commerce companies, and a huge number of companies over the last 20 years.

Criteria for ranking business models

Median successful outcome as primary lens[1:55]
• They decide to evaluate each business type based on the median successful outcome, not the extreme outliers like the world's best plumber.
Incorporating lifestyle and upside[2:24]
• They want to factor both lifestyle (e.g., overwork vs flexible schedule/location) and financial upside into the rankings.
Likelihood of success and difficulty[2:37]
• They note that in some industries, the "median success" might still require being in the top 0.1%, so probability of success must be considered.

Tier-list format explanation

Using S-F tiers from gaming culture[3:03]
• They explain the tiers A-F plus S tier, where S is "God tier" or best of the best; A is better than F, as expected.

Ranking specific business models

MLM (multi-level marketing)

Andrew's rating for MLMs[3:28]
• Andrew ranks MLMs as F-tier, calling them a fundamentally unsustainable business that breaks.
Core problems Andrew sees in MLMs[3:28]
• He argues MLMs rely on recruiting others and make money by "finding the next sucker" rather than selling real services.
• He notes that early entrants can make a lot of money but then the structure always explodes or results in indictments.
Owner vs. downline outcomes[4:11]
• The host points out that for the MLM owner it may not be F-tier, but for the associates in the downline it's F-tier.
• Andrew jokes you can make a lot of money if you are willing to accept 50-50 odds of going to jail.

Freelancer

Andrew's background as a freelancer[4:36]
• Andrew confirms he started making websites out of his apartment as a freelance web designer.
Freelancing rating and rationale[4:57]
• He ranks freelancing as a D, calling it a good way to make a living but fundamentally an owner-operator model that does not scale unless you deliberately scale it.
• He compares freelancing to restaurants or corner stores as legitimate but limited, owner-dependent businesses.

Agencies

Metalab's financial performance[5:16]
• The host says Metalab has likely generated $200+ million in revenue; Andrew responds that the business is "well over into the hundreds of millions of dollars of profits, not revenue."
Andrew's rating of agencies[5:14]
• Despite Metalab's success, Andrew says he would not rank agencies very highly and gives them a tentative C.
Volatility and fear in agency life[5:23]
• He describes running Metalab as being constantly terrified, always swinging between making a ton of money and being about to go out of business.

Why some agencies are better than others

Client stability differences (accounting vs. design)[6:31]
• Andrew contrasts a web design agency with an accounting firm auditing 30 companies, noting that companies dislike switching accountants or auditors, making that version of consulting higher quality.
Feast-or-famine revenue issues[6:17]
• He gives an example of having hired 30 people on $500,000 of payroll: some months you may make $300,000, other months you might make nothing because you have no clients.
Key client risk (e.g., Walmart example)[7:08]
• He describes a scenario where Walmart promises $10 million of work over a year, you panic-hire 30 people, then a new PM cuts the budget and you must lay off those people.

Andrew's agency portfolio and replication attempts

Number and types of agencies run[7:52]
• Andrew says he has had 10-15 different agencies and service businesses including game design, no-code, copywriting, social media, web development, and design.
Success of Metalab vs. other agencies[8:39]
• He says they have not had much success recreating Metalab's success; Metalab started from zero and now does very significant earnings and revenue.
• He attributes Metalab's edge to doing defining work between 2008 and 2015, such as designing the first version of Slack and other groundbreaking projects, which built a hard-to-replicate reputation.
Acquiring Z1 as a "base hit"[9:11]
• Andrew describes acquiring Z1, a smaller Spanish web design agency, for about $300,000 and funneling Metalab's smaller leads to it.
• He says they have likely made single-digit millions of profit from Z1, calling it an amazing base hit rather than a home run.

SaaS businesses

Overall SaaS tier rating[10:01]
• Andrew rates SaaS as a B, emphasizing that quality varies greatly depending on competition and switching costs.
Bad vs. good SaaS examples[10:01]
• He contrasts a flimsy chat-GPT "thin wrapper" app that tricks people into subscribing and then churns quickly with a dominant funeral home management SaaS that all funeral homes use and are reluctant to leave.
• He notes that good SaaS can be highly recurring with strong margins, but you must find niches with limited competition or high switching costs.

Andrew's evolving view of SaaS in the LLM era

Fear of LLM-driven competition[11:26]
• Over the last two years, Andrew became scared of buying software companies because LLMs can increasingly build software, leading to many more competitors.
• He predicts that if a SaaS niche once had 10 competitors, it might soon have 50-100, which will compress margins.
Turning down most SaaS deals[11:32]
• He says Tiny has basically said no to almost every SaaS company they have looked at in the last two years.

Serato case study: niche SaaS with hardware integration

Why Serato stood out[11:42]
• Serato, DJ software built by two guys in New Zealand, is described as the dominant piece of software in the DJ world for about 25 years.
• Andrew notes that many top DJs, including Diplo, use it, and that the founders smartly pioneered and deeply integrated with hardware manufacturers.
Benefits of being the standard with hardware moat[12:26]
• He explains that most DJs use either Rekordbox or Serato, so competition is limited, and DJs often invest about $5,000 in hardware around the software, making switching hard.
• Hardware manufacturers are reluctant to integrate with a random AI-coded competitor lacking a hardware mode, reinforcing Serato's moat.
Serato's financials and growth[12:38]
• Andrew says Serato does about $45 million in revenue and $15 million of EBITDA and has been growing rapidly as it transitions from licensing to a SaaS model.
Why DJ software can keep growing[13:19]
• He argues that as long as being a DJ remains desirable for young men and women, and DJing remains a fun, expressive, potentially fame-bringing activity, the market will persist.
• He describes Serato as owning one of the "toll roads" to becoming a DJ.

Restaurants

Andrew's involvement and rating[15:03]
• Andrew says he owns a bunch of restaurants and ranks restaurants as an E-tier business.
Why restaurants are so hard[14:50]
• He calls restaurants a labor of love; if someone is successful in restaurants, he wants to "Wayne's World" bow to them because it's so hard.
• He outlines the complexity: people wake up at 3am to bake bread, train 30 people, and execute many moving parts just so a customer can eat a good meal at 6pm.
Margins and effort vs. reward[16:01]
• The host notes that most successful restaurants and chains operate on roughly 10% margins at best, with revenue capped by what can be produced each day.
• They emphasize the constant need to be open seven days a week and to remake the product fresh daily, while every customer interaction can impact reputation.
• Andrew says restaurants are important but a terrible path if the goal is to get rich, comparing them to trying to deadlift 300 pounds on day one at the gym.

Online marketplaces

Defining marketplaces and examples[17:15]
• The host defines marketplaces broadly as platforms matching supply and demand, citing Etsy, eBay, Amazon, AngelList, Twitch, and YouTube as examples.
Andrew's rating based on scale[17:28]
• Andrew says it comes down to scale: small marketplaces are very hard and like lightning in a bottle; successful ones can be phenomenal but are highly competitive.
• He likes businesses that become verbs, using Airbnb as an example where the brand is top-of-mind when thinking about renting a house.
Differentiating great vs. average marketplaces[18:21]
• Andrew says a great marketplace like Airbnb is an A-tier business, but he would rank marketplaces in general as C-tier because most attempts fail.
• He mentions niche ideas like a marketplace for borrowing construction tools as examples of concepts he has seen fail repeatedly.
Host's disagreement on marketplace tier[18:37]
• The host disagrees, arguing that a working marketplace like Airbnb should be S-tier due to defensibility and lucrativeness, but concedes the success probability is low.
• They ultimately place Airbnb as an A-tier example while leaving marketplaces in general at C-tier in Andrew's framework.

Owning Airbnbs / short-term rentals

Rating and main risk[20:03]
• Andrew ranks owning Airbnbs as a D, mainly due to regulatory risk.
Andrew's Vancouver apartment experience[20:07]
• He bought a beautiful apartment in Vancouver intending to use it occasionally and Airbnb it the rest of the time, initially making a fortune.
• Then the City of Vancouver changed regulations, destroying his margins; he now has a traditional tenant and the property is far less profitable.
Parents' San Francisco Airbnb change[20:39]
• He says his parents were also making a killing Airbnb-ing their house in San Francisco until the city limited rentals to 90 days per year, eliminating their cash cow for nine months of the year.

Content creator businesses

Defining content creator path[21:29]
• The host frames content creators as people aiming to be the next big podcaster, YouTuber, or Instagrammer, planning to monetize via brand deals or their own products.
Andrew's rating and nuances[21:31]
• Andrew rates content creation as D-tier overall but notes that if you become the next Andrew Huberman, it is an A-tier business.
• He highlights that in a world of AI, having a trusted relationship with an audience is extremely valuable.
Scalability and dependence on creator effort[21:15]
• He argues these businesses are highly profitable and simple to operate but do not scale defensibly because if the creator stops showing up and "bringing the fire" daily, the business goes to zero.

Why Huberman's niche works especially well

Importance of niche and customer LTV[22:24]
• Andrew contrasts a hypothetical Huberman reviewing candy (low affiliate margins) with his actual focus on health supplements, where customer lifetime value is high and ad rates can be substantial.
Equity and free marketing leverage[23:08]
• Andrew says they co-own a Yerba Mate business with Huberman, who can effectively bring around $20 million of free marketing to any business he partners with.
• He reports that their Yerba Mate business has grown roughly 300-400% since Huberman got involved.

Owning and developing real estate

Distinguishing ownership vs. development[24:06]
• Andrew differentiates between simply owning rental properties and real estate development where you buy land or buildings and add value.
Example of value-add strip mall strategy[24:25]
• He references the host's brother-in-law, who knows local tenants needing space, acquires strip malls, pre-arranges higher-quality tenants before closing, and thereby creates a more valuable asset he can refinance.
Overall rating of real estate[24:55]
• Andrew rates real estate as C-tier, acknowledging its predictability but disliking its "ceiling" on returns.
Why Andrew avoids ceilinged assets[25:12]
• He explains that in a 40-tenant apartment building, you can only raise rents so far, and unlike in a business, it is hard to innovate to grow revenue without massive capex.
• He notes he prefers businesses like web design or software where profits can be reinvested for growth, whereas in real estate you mostly use profits or refinancing to buy more properties.
Illiquidity of large real estate fortunes[26:10]
• He observes that many wealthy real estate owners may control $2 billion of assets but only generate around $20 million a year in profits and often have much of that tied up in the next project.
• He calls real estate a great way to make your kids very wealthy, joking that later generations might ruin it by buying an F1 team and losing the fortune.

Investing business models: hedge funds, Buffett, and permanent capital

Framing investing as a business model

Distinction between Buffett-style and typical asset management[27:12]
• Andrew says investment management in general is an incredible business, but he does not categorize Buffett as a typical asset manager because Buffett does not manage other people's redeemable capital in the same way.

Hedge funds and the 2-and-20 model

How hedge fund economics work[27:24]
• He explains the classic hedge fund structure as 2% of assets under management plus 20% of profits.
• He gives an example where raising $100 million and tripling it could yield $30-50 million of carry and fees.
Vulnerability of non-permanent capital[28:24]
• Andrew notes that in typical hedge funds, investors can pull capital, forcing the manager to sell positions, sometimes at a loss.

Why Ackman and Buffett are S-tier

Permanent capital as key advantage[28:24]
• Andrew ranks Bill Ackman and Warren Buffett as S-tier because they have permanent capital via public vehicles where investors trade shares among themselves rather than redeeming underlying capital.
• He explains that in such structures, even if some shareholders sell, the capital remains invested and managers continue earning fees.
Pershing Square scale and staffing[31:00]
• Andrew says Pershing Square has about 50 employees and manages roughly $16-20 billion, and that Bill Ackman simply buys about 10 stocks.
• He notes that Pershing Square charges blended fees of roughly 1-2%, though the exact numbers depend on pools of capital and performance.
Example of Ackman's COVID derivatives bet[31:16]
• Andrew recalls Bill putting $25 million into a derivatives position as "fire insurance" against COVID-driven market declines and profiting about $2.4 billion.
• He notes Ackman collected fees on that huge gain and also personally owns around $6 billion of the capital he manages.

Rating typical hedge funds vs. permanent-capital funds

B-tier for conventional hedge funds[31:54]
• Andrew gives conventional hedge funds a B-tier rating because, despite earnings potential, they can get "blown up" when investors redeem capital.
Ackman's near-blowup and lessons[32:29]
• He recounts how Ackman's bets against Herbalife and on Valiant Pharmaceuticals caused large losses, investors pulled money, and his hedge fund nearly blew up.
• Ackman used $4 billion of permanent capital in Pershing Square Holdings and a roughly $500 million loan from JPMorgan and Jamie Dimon to bet on himself and recover.
• Andrew says Bill learned to avoid shorting stocks and to be more disciplined about businesses with leverage or exogenous risks, even printing "Ten Commandments" plaques like "thou shall not short stocks" and "thou shall not invest in a business with too much debt."

Hedge funds and VCs vs. index performance

Buffett's bet against hedge fund baskets[35:01]
• Andrew cites Ted Seides's million-dollar bet with Buffett that a basket of hedge funds would outperform the S&P; Buffett won, illustrating that most funds do not outperform indexes.
Typical performance of venture and hedge funds[35:30]
• He agrees that most venture capital and hedge funds underperform when accounting for illiquidity and time horizons, while suggesting private equity funds more consistently deliver reasonable returns.

Other business models: local services, VC/angel, and sweaty SMBs

Local services businesses (HVAC, pest control, etc.)

Rating and constraints in local trades[36:43]
• Andrew rates local services like HVAC or pest control as C-tier.
• He says if you can dominate a local industry and are good at internet marketing and hiring technicians, you can do well, but there are only so many technicians available, making scaling and competition tricky.
Operator fit vs. outsider challenges[37:42]
• He notes many white-collar buyers have tried to acquire HVAC or plumbing businesses, only to face skepticism from existing blue-collar staff who wonder why they should work for them.
• He believes these are good businesses for enterprising technicians who start their own firm, but quite difficult for outsiders to operate.

Venture capital and angel investing

Angel investing as E-tier for most people[37:48]
• Andrew groups venture and angel together for discussion but explicitly rates angel investing alone as E-tier for typical people.
Why angel investing resembles roulette[37:54]
• He compares angel investing to roulette, preferring poker-like activities such as buying whole businesses or private equity where odds and information are better.
• He describes the classic founder pattern: they make money, want to pay it forward, find stocks and businesses "slow" or boring, and are seduced by stories of early Uber-style investments.
• He says for laypeople, angel investing is a terrible way to allocate money, though some exceptional angels do very well.
His own illiquid angel portfolio[39:12]
• Andrew mentions he has about $30 million tied up in angel investments that are completely illiquid and says he would much rather own stocks and real estate.

Buying local "sweaty" startups / boring SMBs

Cody Sanchez and Nick Huber as examples[40:01]
• The host uses Cody Sanchez (shown at a laundromat) as a figurehead for the idea of buying laundromats, car washes, and boring local businesses; Andrew says he loves Cody and Nick Huber.
Buying your own job vs. buying a business[40:29]
• Andrew says what Cody and Nick really advocate is "don't work for someone else when you can create your own job," although they phrase it as owning a business.
• He distinguishes buying your job from buying a business, saying a real business should return more than the cost of the owner's salary.
Rating and Tiny's acquisition philosophy[41:58]
• He rates buying a working local business as C-tier and says he and Chris often talk about "skipping the line" by buying already-functioning businesses and improving them instead of starting from scratch.
Andrew's costly experience starting many businesses[40:44]
• After Metalab grew, Andrew took its profits and started about 10 other businesses including dropshipping, a restaurant, and a skincare company; most failed.
• He estimates he put $10-15 million into these "terrible businesses" and ended with only one saleable business and one that was merely alive.
• He believes if he had instead used $1-2 million per year to buy existing businesses and improve them, he'd be further ahead today.

Origin and growth of Tiny as an investment company

Seeding Tiny with Metalab profits

Initial capital and ownership split[41:43]
• Andrew says they started Tiny around 2013 after reading about Warren Buffett, deciding he was playing "easy mode" while they were on "hard mode."
• They seeded Tiny with roughly $4-5 million: Andrew owned 80% and Chris 20%, with Chris contributing about $500k-$1 million and Andrew providing the rest.
• They never injected additional capital into Tiny beyond that initial seed.

Learning by operating and "forks in sockets"

Why operator experience improved investing[44:08]
• Andrew quotes Buffett: "I'm a better businessman because I'm an investor and I'm a better investor because I'm a businessman," agreeing that operating chaos helps you judge businesses.
• He describes trying many bad business models (dropshipping, restaurants, skincare, etc.) as putting "forks into electrical sockets" and says that experience helped Tiny recognize high-quality businesses later.

Public listing history and misleading stock chart

Taking a Shopify themes business public[44:54]
• Andrew explains that before Tiny was public, they had sold a Shopify themes business to a family office, bought it back, and took it public in January 2021 with Bill Ackman as a partner.
• On the first day of trading, its market cap jumped from about $250 million to $1.2 billion in a manic market environment.
Reverse merger into that vehicle[45:56]
• As the stock price later declined from that peak, they merged Tiny into the vehicle, meaning Tiny's public stock chart begins at that inflated moment and then trends downward.
• Andrew emphasizes that Tiny itself had been compounding earnings at 25% from almost nothing, and the visible public dip does not reflect that earlier decade of compounding.

Responding to criticism about Tiny and public perception

Host frames the "prosecution vs. defense" narrative

Public scoreboard vs. operational reality[47:05]
• The host notes that people see Tiny's stock chart trending down from a 2021 peak and question Andrew's "Warren Buffett of the internet" persona and acquisition strategy.
• He juxtaposes that view with the fact that Andrew turned $4-5 million into a public company with hundreds of millions in value, something very few listeners have done.

Andrew's factual rebuttal with current metrics

Tiny's current revenue, ARR, and EBITDA[47:15]
• Andrew reiterates that they have been compounding earnings at 25% for about 10 years, now generating about $250 million of revenue, $65 million of ARR, and over $40 million of EBITDA.
Fund management and consolidated revenue[48:36]
• He says they also manage a $200 million fund through the public company, with $40 million of their own capital, owning businesses like Aeropress and Letterboxd.
• Adding the fund's roughly $65 million of revenue puts them at over $300 million of revenue across 30 businesses, all profitable within the fund.
Ownership and "pump and dump" accusations[49:02]
• Andrew says Chris and he still own the majority of the public company and that he has sold almost no stock.
• He mentions one large transfer of about $8 million in stock to his foundation for philanthropy and notes he has not taken cash out, rejecting "pump and dump" claims as sad.

Acknowledging fair criticism and emotional impact

Understanding the appeal of negative narratives[48:12]
• Andrew admits he previously consumed juicy stories like Kevin O'Leary's true payout and knows it's easy to judge based on one-line blurbs.
• He observes a "dirty" part of human nature that enjoys watching loud, successful people fall, citing Bill Ackman and himself as loud personalities.
Stock underperformance cohort[51:04]
• He notes that 60% of businesses that went public in 2023 are under their IPO price, naming Asana, Sweetgreen, and Coupang as examples, arguing that price declines don't invalidate what founders built.
Being misunderstood as a personal button[50:16]
• Andrew shares that as a kid with ADHD he often got blamed for everything, so being misunderstood is a "big button" for him, making it hard not to argue with critics.
• He says he has to resist "feeding the trolls" and instead focus on delivering good results and building great businesses.

The courage to be disliked, identity boxes, and leaving your lane

Reputation, boxes, and discomfort with change

Warren Buffett quote on reputation and its effect on Andrew[54:04]
• Andrew recalls Buffett's line that it takes 20 years to build a reputation and five minutes to ruin it; he internalized that as a need to ensure everyone thought positively of him.
People's resistance to others leaving their box[54:46]
• He recounts his father, a retired architect, saying people would be confused if "architect David" suddenly called pitching real estate developments and that people don't like it when you leave your box.
• Andrew admits he himself feels uneasy when, for example, a restaurateur pitches a tech startup or a yoga instructor becomes a realtor, and his knee-jerk reaction is "stay in your lane."
Prison-guard metaphor for social labeling[56:08]
• He says we all act like prison guards enforcing labels such as "tech not real estate," "bootstrapped not venture," or pro- vs. anti-crypto, locking ourselves and others into identities.

Examples of public figures punished for crossing domains

Goldman Sachs CEO DJing and media backlash[56:49]
• Andrew cites how Goldman Sachs CEO David Solomon DJs, and media questioned whether the bank suffered because of his hobby; he argues no one would complain if Solomon played golf instead.
Other cross-domain examples (Kim Kardashian, Jonah Hill, Michael Jordan)[57:00]
• He mentions Kim Kardashian getting criticized for prison reform work, Jonah Hill mocked for surfing, and Michael Jordan labeled a betrayer for playing baseball.

Entrepreneurs dreaming of different paths

Lake house conversation about "what would you do if no one was looking"[1:00:06]
• Andrew describes asking a group of entrepreneurs what they'd do if no one was watching; one runs a billion-dollar industrial business but said his happiest moments are cooking and he secretly wants to be a Michelin-star chef.
• That friend felt he could never do it because his ego is tied to being a businessperson and people would think he'd gone insane.

Discovering "The Courage to Be Disliked"

Core idea of the book[59:18]
• Andrew found the book "The Courage to Be Disliked" in January and says its core idea is that seeking recognition is a trap; making everyone happy leads to living someone else's life.
Changing his own approach to likability[59:32]
• He describes the book as giving him the keys to his cell, realizing the walls weren't real and he could walk out.
• His New Year's resolution became to stop playing the likability game, have the courage to be disliked, and say what is true for him.
Newsletter vs. social media as expression[1:01:03]
• He says he's been writing a newsletter where he talks about everything from ADHD to his weird businesses and prefers that to tweeting "toilet thoughts" and fighting trolls.

Contrarian thinking, Founders Fund, and breaking rules

Host's mismatched socks anecdote

Not caring about trivial norms[1:01:18]
• The host recalls wearing mismatched socks in high school despite criticism from his mother and classmates, because he genuinely didn't care about that convention.

Founders Fund's "no rules" investing approach

Conversation with a Founders Fund investor[1:01:18]
• He met with a Founders Fund investor mainly to learn about the firm and was told they avoid rigid rules about stage, check size, or sector, trying instead to find singular businesses.
Fight Club-style rule: no fixed rules[1:02:18]
• He says Peter Thiel created an almost Fight Club-style rule that the only rule is there are no rules, because rules would limit their ability to find one-of-a-kind companies.

Examples of contrarian investments: Bitcoin and Anduril

Bitcoin as a non-obvious investment[1:02:34]
• The host points out that most VCs were blind to Bitcoin due to their focus on traditional startups, while Founders Fund was one of the few that owned a lot of Bitcoin from around 2014-2015.
Anduril and defense tech contrarianism[1:03:53]
• He explains that when Google abandoned a Pentagon project due to employee protest, investor Elad Gil saw a huge opportunity for those willing to build a weapons company, leading to Anduril's creation.
• He reasons that the U.S. will have a defense department and need weapons, and high-tech weapons built by a modern company make sense despite public controversy.

Role models who reinvent themselves and follow intrinsic interests

Jesse Itzler and choosing soul-nourishing roles

Jesse's varied career path[1:04:29]
• The host describes Jesse Itzler's trajectory from white rapper to jingle writer, to selling a sports jingle company, to starting a private jet company, to coconut water, to running events and sauna products.
Choosing to "be on the bus" as assistant coach[1:06:18]
• Jesse told him he wanted to be an assistant basketball coach at a local college simply to be "on the bus" with the team again, because those were some of his happiest memories.
• The host found this so resonant that he became an assistant high school basketball coach himself for similar reasons.

Kevin Rose, Tim Ferriss, and being unboxable

Kevin Rose's eclectic investments and projects[1:06:52]
• Andrew tells a story of a donut shop in Kauai whose purple coconut-oil-fried donuts impressed Kevin Rose so much that he invested about $10 million to scale the business.
• He says Kevin also engages with companies like Teenage Engineering and an Alzheimer's drug startup, projects that don't fit a single box.
Magnetism vs. formulaic investing archetype[1:07:18]
• Andrew contrasts Kevin and Tim Ferriss, who attract interesting opportunities by sharing their varied interests, with the archetypal "autistic super genius" investor who buys only laundromats or a narrow vertical.
• He doubts many entrepreneurs feel drawn to sell their company to a rigid spreadsheet-driven buyer compared to someone interesting and multidimensional.

Aeropress and Letterboxd as passion-aligned acquisitions

Turning personal hobbies into acquisitions[1:09:37]
• Andrew says he became a barista and obsessed with coffee, which led to buying Aeropress.
• His love of movies initially led him to explore film investments (which looked like money-losers), but happenstance coffee with the founder of Letterboxd in Auckland led to an acquisition offer within four hours.

Envy, inputs vs. outputs, and designing satisfying work

Host's principle: be jealous of inputs, not outputs

Redirecting envy[1:12:02]
• The host argues it's hard to eliminate envy, so instead you should be jealous of people's inputs (how they spend their days) rather than their outputs (results or wealth).
• He suggests using this to discover what you truly want, by noticing whose daily work you'd gladly swap for.

Bill Simmons as an example of ideal inputs

Bill Simmons's career and enthusiasm[1:12:29]
• The host recounts Bill Simmons starting as a rejected newspaper applicant, building a Boston sports blog, joining ESPN, creating 30 for 30, being fired, and then founding The Ringer.
• He describes a clip where Simmons runs through the Ringer office carrying a chair and mic to talk about an NFL trade on another podcast, purely out of excitement.
• He is jealous not of Simmons's sale proceeds but of the fact that Simmons spends his days talking sports with friends even though he no longer needs the money.

Andrew and host on matching work to strengths and joy

Separating talent from enjoyment[1:14:13]
• Andrew notes there are things he is great at, like sales and pitching, that actually drain his energy and make him miserable.
• He sees his ideal role as using his talent for writing and talking about ideas, then routing resulting opportunities into his businesses.
Host's realization watching Emmett run Twitch[1:15:19]
• After Twitch acquired his company, the host watched founder Emmett Shear's day-back-to-back boardroom reviews of team memos-and realized he personally would find that life miserable despite admiring Twitch's success.
Choosing projects you would do 3,000 times[1:16:57]
• When planning a new content project, he asks not what will get millions of views, but what he would enjoy doing 3,000 times, assuming repeated effort will bring both mastery and results.

Craftsmanship vs. improvisation in content

New project as a shift to craftsmanship[1:17:23]
• The host contrasts the podcast's live, improvised, largely unedited format with his new project, which he describes as more crafted-using a scalpel to make one great piece.
Andrew's joy in writing a book[1:18:23]
• Andrew says the happiest he's been in ten years was writing his book with headphones on, creating something that might still be relevant in 20 years.
• He contrasts that with the ephemeral nature of tweeting and podcasting and appreciates occasionally zooming out to make more lasting work.

Closing remarks and Andrew's newsletter

Andrew's focus on newsletter writing

Moving away from Twitter[1:18:34]
• Andrew says he has not been tweeting much and instead writes a monthly newsletter where he shares random things he's excited about, sometimes business-related, sometimes not.
Value of slower, deliberate writing[1:18:23]
• He finds it much more enjoyable to sit down and write something formal and take his time rather than posting impulsive thoughts and arguing with trolls.

Lessons Learned

Actionable insights and wisdom you can apply to your business, career, and personal life.

1

Evaluate business models by their median successful outcome, lifestyle demands, and likelihood of success rather than by extreme outlier wins or glamorous stories.

Reflection Questions:

  • • When you look at your current or planned business, what does a realistic "median successful" outcome actually look like in terms of income, hours, and stress?
  • • How would your decision-making change if you prioritized day-to-day lifestyle quality and probability of success over the chance of a huge but unlikely payoff?
  • • What one business idea or path could you stop pursuing this month because, on honest reflection, its median outcome and odds don't justify the effort?
2

Permanent, stable capital and durable moats (like high switching costs or deep hardware integration) make an investing or SaaS business far more resilient than models reliant on fickle clients or redeemable funds.

Reflection Questions:

  • • Where in your business or portfolio are you overly exposed to other people's ability to "pull their money" or switch providers quickly?
  • • How could you redesign your offer, contracts, or product so that customers become progressively more locked in because they genuinely rely on you?
  • • What is one concrete step you can take this quarter to move even slightly toward more permanent, stable capital or more durable competitive advantages?
3

For most people, starting or buying simple, already-working businesses and improving them is a better path than spraying capital across angel investments or many new ventures.

Reflection Questions:

  • • Looking at your financial and time commitments, how much is going into speculative, story-driven bets versus solid, understandable businesses?
  • • How might your results differ over the next five years if you focused on buying or operating one boring, proven business instead of funding multiple startups?
  • • What existing business (even a very small one) could you realistically acquire or join and improve with your current skills and resources?
4

Chasing universal approval and staying inside others' identity boxes is a trap; developing the courage to be disliked frees you to pursue work and roles that are actually true to you.

Reflection Questions:

  • • In what specific ways are you still shaping your career or public persona to fit how other people see you rather than what you genuinely want?
  • • How would your choices change over the next year if you accepted that some colleagues, friends, or followers will dislike or misunderstand you no matter what?
  • • What is one "box" or label you could deliberately step outside of in the coming months, even if it risks criticism, that would move you closer to a more authentic life?
5

Use envy as a compass by being jealous of people's daily inputs-their routines, conversations, and problems-not their wealth or status, and then redesign your own work accordingly.

Reflection Questions:

  • • Whose typical workday do you find yourself genuinely envying, and what exactly about their daily activities resonates with you?
  • • How could you reconfigure your current role so that more of your time is spent on the kinds of tasks and conversations you envy in others?
  • • What small change could you make this week to swap out one hour of work you dread for one hour doing work that feels more like those "inputs" you admire?
6

Long-term success often comes from aligning your work with things you could happily do thousands of times, rather than optimizing for what seems most popular or prestigious in the short term.

Reflection Questions:

  • • If you had to repeat your current main activity 3,000 times, how confident are you that you would still be energized rather than exhausted or resentful?
  • • What projects or activities in your life give you energy every time you do them, even when there's no immediate external reward?
  • • Which one recurring activity that you genuinely enjoy could you commit to doing more consistently over the next year, trusting that mastery and results will follow?

Episode Summary - Notes by Charlie

I Ranked the Best & WORST Businesses to Start Before 2026 | Andrew Wilkinson
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