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My First MillionIf I Could Start Over Again, This Is What I’d Do To Get Rich - Scott Galloway
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CHAPTERS
- 0:00 – 3:25
Cold open and Sam's admiration for Scott Galloway
Shaan previews the episode, in which Scott Galloway shares what he'd do at 25 and opens up about his finances. Sam then explains why he looks up to Scott, and the three trade banter about his brand and writing.
- •Shaan previews Scott's two answers for what he'd start at 25, depending on credentials
- •Scott's finances are discussed more openly than in his past interviews
- •Sam admires Scott's language and his range of businesses
- •Sam notes Scott is better known as a brand than as a founder
- 3:25 – 5:35
Surviving rejection and losing it all with Red Envelope
Scott says his key skill is enduring rejection and moving on. He recounts his smaller e-commerce ventures and how Red Envelope went to zero in 2008 after a string of mishaps.
- •The ability to mourn and move on is his main skill
- •America tolerates failure rather than embracing it
- •Early e-commerce ventures sold for modest sums
- •Red Envelope collapsed after a warehouse error and a pulled credit line, and he lost nearly everything
- 5:35 – 9:14
Scott's net worth, financial anxiety and the L2 exit
Asked when he felt secure, Scott says he still doesn't, and explains why he is open about money. He walks through his exits, including L2's $158M sale, and says investing has made him more than his businesses.
- •He says talking openly about money counters decorum that benefits the wealthy
- •He gives away all his current income
- •First company sold for $28M, but he kept only a few million after splitting it and paying taxes
- •L2 sold for $158M with only one venture round, and he owned a large share
- •Investing has earned him more than his businesses
- 9:14 – 10:41
How Sam made $20M and why wealth still feels insecure
After a HubSpot ad break, Scott presses Sam on what he made from his exit. Sam says he walked away with about $20M yet still feels scarcity, and Scott advises him on diversification.
- •Sam walked away with about $20M at 31 or 32
- •Sam keeps an 80/20 index and bond portfolio plus HubSpot and Airbnb stock
- •Scott says Sam is right to prioritize not getting poorer
- •Scott's mistake was doubling down on single companies after wins
- •He suggests buying the whole haystack rather than a needle
- 10:41 – 16:21
Financial literacy, living below your means, and the value of cash flow
Shaan asks whether Scott's anxiety is irrational, and Scott says it is real but useful. Sam and Scott discuss how ongoing income calms fears more than a one-time windfall and keeps you in the market.
- •Scott says his neurosis is real and also pushes him to stay on top of his money
- •Being good at money requires thinking about it often and understanding things like interest rates
- •Wealth comes from the gap between what you earn and what you spend
- •Sam says regular cash flow from the podcast eased his anxiety more than the exit
- •Scott says earning keeps you in the market and gives comfort even when investments fall
- 16:21 – 19:02
If you have no degree: buy a boomer's small business with seller financing
Shaan frames the show's focus on current opportunities and asks what Scott would do at 25. Scott says the answer depends on your situation, and for someone without credentials he suggests buying an aging owner's small business using seller financing.
- •Scott dislikes hustle culture advice because it ignores people's circumstances
- •Boomer-owned businesses doing $500K to $10M a year often lack a succession plan
- •Owners' kids often don't want the business
- •He'd propose buying it slowly over five years and paying the owner coupons
- 19:02 – 19:56
If you have a degree: get rich slowly at a big company
For credentialed people, Scott recommends joining a large platform company. He argues that the largest companies have outperformed the rest and that entrepreneurship is over-romanticized.
- •Antitrust is no longer effectively constraining big companies
- •The largest market-cap companies have far outperformed the bottom nine deciles over 30 years
- •You can get rich slowly at places like Google or McKinsey
- •The US corporation is the greatest wealth-creating vehicle in history
- 19:56 – 22:54
The healthcare carcass: AI opportunities in a $4 trillion industry
For credentialed entrepreneurs who can raise money, Scott points to AI in US healthcare. Sam is skeptical because of regulation and insurers, but Scott says the industry is too bloated not to be disrupted.
- •US healthcare is $3.5 to $4 trillion, with costs outpacing inflation for 40 years
- •AI could move healthcare from defensive to proactive
- •Scott invested in 98.6, a text-based healthcare company, and has written it down 80%
- •Sam cites heavy regulation and insurance complexity
- •The US spends $13,000 per person versus about $6,500 in the UK, with worse outcomes
- 22:54 – 28:23
GLP-1 is bigger than GPT-4: Ozempic and instinct
Scott says GLP-1 drugs are the most under-hyped trend and bigger than GPT-4. Sam shares his experience with semaglutide, and Scott argues the drugs could help update human instincts, such as cravings for food and alcohol.
- •Scott would run a hedge fund shorting food stocks
- •He says our instincts haven't caught up with modern production
- •People on Ozempic reportedly drink less alcohol and bite their nails less
- •Sam describes the cost of $500 to $1,000 a month and the rising dosage
- •Downsides mentioned include upset stomach and muscle loss
- 28:23 – 31:39
Second-order effects of GLP-1 and the economics of obesity
Scott considers the knock-on effects, such as lower demand for vaccines and hospital networks, and cites the Milken Institute's $1.7 trillion obesity cost. He says the technology will matter more to the real economy than AI, and recaps his advice.
- •A less obese population could be less vulnerable to coronavirus, so Moderna could suffer
- •Scott criticizes how the left politicized obesity
- •The Milken Institute puts obesity-related costs at $1.7 trillion a year, or 7% of the economy
- •He thinks AI has hit peak hype for investors
- •He recaps his advice: small business, big company, healthcare AI, GLP-1
- 31:39 – 35:19
Who takes GLP-1, and Scott's Accutane story
Asked whether he's tried GLP-1, Scott says no and thinks it should reach poor and middle-income obese households. After Sam describes a CVS pharmacy scene, Scott tells how Accutane changed his life as a teenager.
- •Scott thinks rich people are likely driving current sales
- •Sam describes pharmacies announcing prescriptions out loud
- •Accutane cleared Scott's acne and boosted his confidence in his late teens
- •He takes creatine and struggles to keep weight on
- 35:19 – 39:46
The Inverse Galloway Index and being held accountable
The hosts bring up the Inverse Galloway Index and the Macy's call. Scott says his prediction record is cherry-picked, accepts that he should be accountable, and describes harsh Twitter attacks from people invested in companies he criticized.
- •The index tracks companies Scott said would fail that outperformed the S&P
- •Scott says the Macy's clip was taken out of context from a talk where he also predicted Amazon buying Whole Foods and stores
- •The index site was last updated in February 2022, and he says people lose interest when the narrative fades
- •He says venture capitalists and bots attack critics of their investments
- •He hired a firm to try to unmask attackers
- 39:46 – 42:58
Is Putin's regime cyber-bullying Scott?
Scott speculates that Russia could fund AI-driven campaigns against pro-Ukraine voices on social media. Sam pushes back, asking for proof and whether Scott is a big enough target, and Scott defends the logic.
- •Scott frames it as what he would do if he were Putin
- •Sam says the comments alone aren't proof and could come from people who simply dislike him
- •Scott says public opinion decides wars and critics' credibility is a target
- •Scott calls Ukraine support the best investment the West has made
- 42:58 – 44:56
Enjoying the Scott Galloway brand and the rich-but-anonymous algorithm
Sam asks whether Scott prefers being a brand or an operator. Scott says he enjoys the recognition and calls himself addicted to strangers' affirmation, while noting that being rich but anonymous is the ideal and that he may eventually become the villain.
- •Recognition feels especially nice in front of his teenage sons
- •He admits he is addicted to affirmation from strangers
- •He says the formula for happiness is to be rich but anonymous
- •He expects America's build-up-then-tear-down cycle to turn on him eventually
- 44:56 – 49:21
How Scott builds talks that earn $112K per engagement
Sam asks about Scott's speaking process. Scott says speaking is his most lucrative business and describes the months of data work, humor and rehearsal behind each talk, before the hosts wrap up.
- •He got 340 inbound requests, accepted 30, and averages $112,000 per talk
- •He spends about three months with analysts on themes, data, slides and video
- •Humor lowers defenses so audiences are open to new ideas
- •He feels the work lets him make an impact, especially on struggling young men
- •Shaan says Scott educates by entertaining
