Scott Galloway joins Sam and Shaan for a candid conversation about his financial history — from losing everything with Red Envelope to selling L2 for $158 million. He shares what he’d do if starting over with no degree (buy boomer businesses) versus with credentials (work for a big company), identifies AI + healthcare as the biggest entrepreneurial opportunity, and makes a strong case that GLP-1 drugs like Ozempic are a bigger economic disruption than AI. He also breaks down his $112,000-per-speech business and admits he’s still not financially secure despite being worth over $100 million.
Speakers: Sam Parr (host), Shaan Puri (host), Scott Galloway (guest)
Introduction: Compliments, Language, and What Galloway Is Known For [00:00:00]
Sam: I’ve been listening to you a long time — started with L2 and No Mercy No Malice. I look up to you because we have a lot of similar characteristics. Erectile dysfunction? Not yet. Anger. Depression. You’re pretty buff. You like to post shirtless pics. You’re hard to peg down politically. You have beautiful language — you’re better than I am. And you started a bunch of amazing businesses, but you’re kind of known as Scott Galloway the brand more than as an operator.
Shaan: This whole episode is Sam complimenting you. It’s a reverse roast. You just sit there for an hour feeling good.
Scott: I’m really enjoying this. It’s like a verbal massage.
Sam: You’ve said the key to your success is rejection — you’ve had a lot of it. From capital providers, the marketplace, women. Your skill is the ability to endure it and move on. The ability to mourn and move on.
Scott: And the wonderful thing about America is that we don’t embrace failure — that’s BS — but we tolerate it. I know so many successful people who did something on their own that didn’t work, and they got stuck. They can’t get past it. A bullet to the arm becomes an opportunistic infection that starts damaging everything. That’s my only real skill — resilience.
Scott Galloway’s Financial History [00:08:00]
Scott: I’ve had a lot of false starts. A pet e-commerce company — put a million bucks in, sold it for a million and a half. A travel site — sold that for a little bit. Then Red Envelope, which went public on the NASDAQ in 2002. I got into a war with the board, did a proxy fight, took over the board, put more of my own money in. Then 2008 came. There was a long shore strike. A software malfunction sent 10,000 gifts to the wrong addresses over the holidays. A Wells Fargo analyst decided the credit crisis was coming and pulled our line. The stock went from seven dollars a share to zero in eleven days. Company declared Chapter 11. I lost pretty much everything.
Sam: Do you remember the inflection point where you felt financially secure?
Scott: I still haven’t hit that point. I’m still very anxious about money. I think about it all the time. I give away every dollar I make in current income — I wanted to catch up to the non-philanthropic Scott who gave away nothing for the first 45 years — but I’m still trying to make more. I still feel financially insecure. I still worry about a recession becoming a depression.
Scott: I sold my first company for 28 million. By the time I split it with my ex and paid taxes I had a few million. Same with Red Envelope — made a few million but lost it. Then L2. That was the big one. We sold for $158 million. We’d only done one round of venture capital, so the common shareholders — me and the top six employees — owned about 70% of it. That was life-changing money. I’d never had anything like that before. We sold in 2017, and I’ve honestly made more money investing that windfall than from all my businesses combined.
Sam: I walked away from my acquisition with about $20 million at 31 or 32. And I still feel financially insecure.
Scott: That’s rational. I’ve lost it all a couple times. The reason I could start again was because I never had debt — I always lived below my means. But you should be doing exactly what you’re doing: index funds, not trying to find the needle in the haystack. Buy the whole haystack.
Sam: I do 80/20 index and bonds. Plus I still own some HubSpot and Airbnb stock.
Scott: The cash flow from ongoing businesses is also what changes things. When you have a business that throws off regular income — checks every month — that feels different from a windfall that sits in a brokerage account and might evaporate. It keeps you in the market. You have to understand what the market values. That keeps you sharp.
If I Were 25 Again: Two Answers [00:25:00]
Sam: What opportunities do you see right now? If you were 25, what would you work on?
Scott: A lot depends on your situation. I’ve never liked hustle culture where people say “offer to carry Jeff Bezos’s bags.” If you’re a single mother, that’s just not an option.
Scott: If I had no degree: there are going to be a lot of small businesses — carpet cleaning, gas stations, furniture companies, auto suppliers — owned by Boomers who need liquidity events. They’re hitting their 60s and 70s. They don’t have succession strategies because their kids went to Emory and want to work at Google. These are businesses doing between half a million and ten million a year. I would be scrappy about getting into one, understanding it, and finding an owner who’d let you buy it slowly over five years with seller financing. That’s an enormous opportunity that’s massively underrated.
Scott: If I had credentials from an elite school: go work for a big company. This is wildly underrated. We live in an era where antitrust is no longer in effect. The largest companies by market cap have outperformed the bottom 90% of the market by a huge factor over the last 30 years. At Google, at McKinsey — you’ll meet smart people, you’ll get mentors, you’ll get rich slowly. The mythology of entrepreneurship obscures how extraordinary these organizations are.
Scott: If I were a credentialed entrepreneur who could raise money: the intersection of AI and healthcare. US healthcare is three and a half to four trillion dollars. Four out of five people aren’t happy with it. Costs have outpaced inflation for 40 years. We spend $13,000 per person and die earlier and are more obese than the UK, which spends six and a half thousand. That is the mother of all opportunities. I want to take healthcare from defensive to offensive — give your grocery receipts, workout routine, health records, and sleep patterns to a company that gives you prescriptive proactive lifestyle recommendations.
Sam: That seems impossibly regulated.
Scott: Look at how bloated this thing is. Thirteen thousand per person. UK spends six thousand and lives longer. That’s the biggest chin in the world. There’s going to be disruption, and I’d want to be in the way of it.
GLP-1 Is Bigger Than AI [00:38:00]
Scott: The thing I’m most excited about right now — I think GLP-1 is bigger than GPT-4. Ozempic, Wegovy. I’ve tested semaglutide — it’s amazing.
Shaan: We’ve been saying the same thing.
Scott: Here’s the scale of this: 40% of Americans are obese, 70% are obese or overweight. The Milken Institute estimates obesity-related costs at 1.7 trillion dollars a year — 7% of our economy. That’s knee replacements, cardiac, obesity-related cancers. What happens when you cut 7% from the real economy’s cost structure?
Scott: But it goes even deeper. Our instincts haven’t caught up to the industrial production of the last 150 years. We eat too much. We drink too much. Men are staying home watching porn instead of building relationships. We’re too responsive to other people’s opinions on Twitter. These GLP-1 drugs don’t just help people eat less — they moderate cravings. People on Ozempic drink 60% less alcohol. They bite their nails less. They’re moderating instincts that were calibrated for 300,000 years on the savannah, not for the modern environment.
Scott: If you could calibrate these drugs to help people moderate their cravings across the board — food, alcohol, affirmation-seeking, screen time — that’s not just a weight loss market. That’s the biggest addressable market in the world. I think it could be the scaffolding on human instinct.
Sam: What are the downsides?
Scott: It costs $500-1,000 a month. You have to keep increasing your dosage. And I worry that you don’t actually develop healthy eating habits — you just eat less and lose muscle. It’s not a terribly new drug — these have been around 30 years in some form — but as it’s being prescribed now it’s relatively new, so there will be downsides we haven’t seen.
Scott: The second-order effects are wild. Hospital networks could go out of business. McDonald’s gets disrupted. Airlines save fuel because passengers weigh less. And mRNA vaccine demand decreases — if you drastically reduce obesity, you drastically reduce viral vulnerability.
Shaan: You should make GLP-1 your philanthropy. Just be the guy who gives it to the masses.
Scott: I actually think I’ve made the list. When Putin decides he needs to fund a social media operation to undermine Western support for Ukraine, and he hires a PR agency to create bots — the people going on Face the Nation saying “this is the best investment the West has made in 90 years, we’ve unified Europe, we’ve woken up NATO” — I think I’ve made that list.
Shaan: You hired a firm to unmask the people attacking you on Twitter.
Scott: People who came after me professionally and in character — hard, sustained attacks — I found it was almost always someone with a large financial position in a company I’d called overvalued. When I say a cryptocurrency has no underlying technology, the people in that coin take to Twitter and hire bots. It’s not just insecurity on my part — it’s rational threat response from the people I’m disrupting.
The Inverse Galloway Index [00:52:00]
Sam: There’s this Inverse Galloway Index — tech companies you predicted would fail have outperformed the S&P and returned 61%.
Scott: I get it wrong. I should be held accountable. I predicted Tesla would fail spectacularly — that one aged poorly. The Macy’s call: I said multichannel retail was the future and Macy’s was well-positioned. They weren’t. That was wrong.
Scott: But the index was last updated in February 2022, because it stopped being interesting when the narrative went away — which is when the market turned and some of those companies started struggling. It’s selective. When I’m right, no one tracks it. When I’m wrong, the index stays up.
The Speaking Business [01:05:00]
Sam: Your talks are unlike everyone else’s — 150 slides, each with real data, and you talk fast in a rhythm that works. What’s the process?
Scott: Speaking is the most lucrative business I’ve ever been in. I had 340 inbound requests and accepted 30. I average $112,000 per engagement. And my attitude is: if someone’s paying me that much, I can’t just show up and be charming. I’ve got to bring something unique.
Scott: I spend the better part of three months with a team of analysts at Prop G finding themes, data, humor, video clips. Then we choreograph it, practice it, test it. Like a comedian testing material before the Netflix special. Humor lowers people’s defenses so they’re open to new ideas — it softens the beach for the insight.
Scott: I get to go to interesting places, pick the most interesting events. MasterCard brings me to Barcelona for a day. It’s a victory lap right now. But you can’t just show up with war stories about how awesome you are — you need insight and data they haven’t seen.
Scott Galloway the Brand [01:15:00]
Sam: Are you enjoying being Scott Galloway the brand more than being the founder of companies?
Scott: On the whole, this phase is really wonderful. People come up and are incredibly nice. I have 13 and 16-year-old boys and everything I do is tragically uncool in their eyes — so when someone comes up in front of them and wants a picture, it feels really nice. I went to an Arsenal game and people came up. A 16-year-old girl at the Taylor Swift concert made me a bracelet. I’m addicted to affirmation from strangers — it’s pathetic, but I know it, so I can modulate it.
Scott: There is an algorithm for happiness though: be rich but anonymous. At some point I’m going to become the villain. There’s an entire industry in America around building people up and tearing them down. I wonder when my story turns. But for right now, it’s wonderful.
Shaan: You’re excellent at packaging smart things and performing them. You can’t educate without entertaining, and you do both. This is what you were meant to do.
Scott: Thank you. Now I’ll bury you in the charts.
Sam: See you in the trenches. Thanks, Scott.