Podcast Summary: My First Million – "Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered)"
Hosts: Sam Parr & Shaan Puri (HubSpot Media)
Guest: Scott Galloway
Date: February 16, 2026
Episode Overview
In this lively and unfiltered episode, Sam and Shaan sit down with NYU Stern Professor, entrepreneur, and provocateur Scott Galloway for a candid deep-dive. The conversation covers power, status, money, business, aging, masculinity, social trends, and personal philosophies. True to the title, the hosts pepper Scott with the “10 spiciest burning questions” they could think of, encouraging honest, occasionally controversial takes—no topic is too taboo.
Key Discussion Points & Insights
1. Davos, Star Power, and the American Brand
[00:00 – 04:51]
- Scott shares his recent experience at the World Economic Forum in Davos, reflecting on the “star power” of Governor Gavin Newsom (“That guy is the definition, the manifestation of Riz, man.” – Scott, 04:03) and the fading luster of America’s brand globally.
- Noted concern about the shift in brand from US “capitalism & consumption” to “chaos, coercion, and compliance.”
- Challenges the view that billionaires are necessarily bad people, instead finding many to possess high character and the ability to create allies.
2. Purpose, Wealth, and Life Transitions
[05:39 – 10:55]
- Scott’s highest goal now is contributing more than he takes, especially by raising “good men.”
- Says that his purpose shifted after his mother’s illness and death from “being rich and awesome” to protecting those he loves.
- Acknowledges working obsessively from 25–45, motivated by insecurity and desire for economic security, and notes how “your number keeps going up.”
- “I spend money like a 50s gangster just diagnosed with ass cancer. I am living large and I love it.” – Scott, 10:11
3. The Art of Smart Spending
[10:55 – 14:26]
- Top luxury purchase: Fractional ownership of private jets—“lowers the bar for fun,” saves time, enables more experiences with family.
- Dismisses high spending on art and wine as attempts to buy culture/status: “No, it doesn't. You're still the same douchebag.” – Scott, 12:38
- For families: Travel and experiences with kids offer greatest happiness boost.
4. Macro Predictions, Markets, and GLP-1s
[14:26 – 24:35]
- Scott stands by prediction that America’s stock market is likely overvalued; recommends diversification as the most powerful financial tool.
- Praises GLP-1 drugs (e.g., Ozempic, WeGovy) as “more transformative than AI,” suggesting mass distribution could halve US healthcare costs (“GLP-1 is the most transformative technology of the last 20 or 30 years. It's the biggest thing since GPS.” – Scott, 19:26).
- Advocates for policy innovations: national service, a $25/hr minimum wage, ending capital gains and mortgage interest deductions to rebalance generational wealth disparities.
5. Old vs. Young: Policy & Wealth Transfer
[23:03 – 24:41]
- Scott is critical of social and fiscal policies that have shifted wealth to seniors at the expense of younger generations:
- “Old people are basically raping our economy for the last 30 or 40 years. It needs to stop.” – Scott, 24:04
6. The Male Loneliness Epidemic & Third Places
[24:41 – 31:07]
- Identifies “third places” (bars, sports leagues, clubs) as powerful antidotes to male loneliness—both a policy and business opportunity. Calls for public subsidies to encourage social connection and less restrictive housing development.
- Candidly admits the most profitable businesses currently “are tapping into young men’s worst instincts” (betting, gaming, social media).
7. Sexy vs. Boring Businesses
[27:05 – 31:07]
- Scott’s investment thesis: “The sexier it is, I want to join. I won’t get near it with a check… The more boring and less sexy an investment is, that’s where you invest.”
- Recurring revenue models and “boring” real estate have yielded best returns for both Scott and Shaan.
8. Marriage, Relationships & Masculinity
[31:36 – 35:54]
- On marrying well: Find a partner who genuinely likes the real you. “The best relationships I’ve ever had are people that I can be me around and they just really like me for me.” – Scott, 31:50
- Advice for marriage success:
- Put the scorecard away; don’t keep relational scores.
- Always express desire.
- Never let a woman be cold or hungry: “Pashminas and power bars, wherever you are.”
9. On Communication, Writing & Creativity
[35:54 – 44:35]
- Scott credits both natural talent and relentless practice (writing every week, teaching, speaking) for his quick wit and memorable soundbites.
- Creative process involves late-night “flow states,” collaborative editorial meetings, and leveraging a team (“The key between a practice and an enterprise that creates real money is to find outstanding people.” – Scott, 40:45)
- Regrets not being a more empathetic boss; now strives for greater kindness and generosity.
10. Life, Shoulds, and Money’s Meaning
[46:35 – 53:15]
- The “should” bucket: Economic security allows you to cut out the obligations you don’t want to do—prioritize “want to” and “have to.”
- “The real power of economic security is: eliminate the should bucket.” – lesson from Barry Rosenstein, 49:05
- Money is a means, not the end—focus on meaningful experiences, relationships, and avoiding regrets about misallocated time.
11. Defining Economic Security
[51:03 – 55:33]
- Formula: Take your annual “burn” (what you need to live as you wish), multiply by 25, assume a 4% after-tax return. That’s your target net worth.
- For Scott, currently $300–400K/month (needs $125M net worth). But acknowledges that in major cities (Manhattan, SF), even $2–3M/year can feel “not rich” due to cost of living.
- Honest talk: Young people often underestimate what it takes to afford a high-burn lifestyle in costly cities.
12. Uncomfortable, Unpopular Advice to His Sons
[56:41 – 61:38]
- “Drink more, go out, make a series of bad decisions that might pay off. When you're in the company of women, you pay for everything, always.”
- Strong, old-school view: No woman will want to kiss a man who splits the check.
- “I hate it when men split checks. Man the fuck up. You get this one, I get the next one.” – Scott, 58:22
- Concedes partner’s point: compulsively paying for everything can stem from ego/insecurity and harm friendships; insists, though, on always paying when it comes to women.
13. Philosophy, Code, and Creating Movements
[61:38 – 70:45]
- Having a personal code—however imperfect—makes life and decision-making clearer.
- Announces “Resist and Unsubscribe”—a movement and website urging consumers to cancel their Big Tech subscriptions to send a powerful signal to markets and policymakers.
- “70% of our economy is consumer spending. ... The fastest way to make the markets move right now is to go after the companies that are 40% of the S&P.” – Scott, 63:06
- Believes collective consumer action (even a few million unsubscribes) hits these “inflated valuation” companies at the soft spot (subscriptions), with quicker policy effects than traditional protest.
Notable Quotes & Memorable Moments
- “I spend money like a 50s gangster just diagnosed with ass cancer. I am living large and I love it.” (Scott, 10:11)
- "Old people are basically raping our economy for the last 30 or 40 years. It needs to stop." (Scott, 24:04)
- "If someone offers me four or five times my mother's annual salary to speak, I can't help it. I go." (Scott, 48:30)
- "Economic security is the ability to eliminate the should bucket." (Recounting advice from Barry Rosenstein, 49:05)
- “No one feels sorry for you, but if you live in Manhattan, you can earn $3 million a year and live paycheck to paycheck.” (Sam, 53:15)
- "You want to cut your burn, move to Florida." (Scott, 54:05)
- “An imperfect code is better than no code at all.” (Scott, 62:33)
- “The soft tissue. This is the testicles of the economy. These companies are way over their skis. Their valuations are inflated.” (Scott, 70:03)
Important Timestamps
- Davos, Newsom, and Star Power: 00:47 – 04:51
- GLP-1s as Transformative Tech: 17:55 – 20:31
- Generational Wealth and Fiscal Transfers: 23:03 – 24:35
- Investing: Boring > Sexy: 27:09 – 31:07
- Marriage, Relationships Advice: 31:50 – 35:54
- Building a Content Enterprise: 39:45 – 44:35
- Economic Security, "Should" Bucket: 50:04 – 51:57
- Advice to Sons, Masculinity & Paying: 56:41 – 61:38
- Resist & Unsubscribe Movement: 63:00 – 70:45
Conclusion
This episode delivers exactly what the title promises: hard-hitting questions and even harder-hitting commentary from Scott Galloway, sprinkled with sharp wit and real talk. Topics range from macroeconomics and investing to personal philosophies on marriage, masculinity, and what it means to lead a meaningful life—especially after you’ve “made it.” Whether dispensing tough love to the next generation or laying out a battle plan for consumer-driven protest, every segment is brimming with actionable wisdom, humor, and conviction.
If you want unfiltered perspectives on money, power, business, and modern life—this episode is essential listening.