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  1. My First Million
  2. Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered)
Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered)

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered)

My First Million · Feb 16, 2026

Scott Galloway shares unfiltered advice on wealth, purpose, and life. He discusses wise spending, investing in boring industries, and why he's unsubscribing from Big Tech.

An Imperfect Personal Code Is Better Than Having No Code At All

In a world with too many incoming decisions, having a personal code or operating philosophy is critical. An imperfect framework provides structure and consistency, which is superior to handling every situation extemporaneously.

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered) thumbnail

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered)

My First Million·3 days ago

The Ultimate Aphrodisiac for Men is the Follow-Up Question

Instead of relying on 'controlled boasting' to attract a partner, men should focus on showing genuine interest in the other person. Asking thoughtful follow-up questions is a powerful and often overlooked tool for building connection.

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered) thumbnail

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered)

My First Million·3 days ago

Invested Capital Returns Are Inversely Correlated to How Sexy an Industry Sounds

The most profitable investments are often in boring, unsexy industries like B2B SaaS. Consume cool, sexy products and experiences (like members' clubs), but invest your capital where there's less competition and hype.

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered) thumbnail

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered)

My First Million·3 days ago

Calculate Economic Security by Multiplying Your Annual Burn Rate by 25

To determine the amount of money needed for financial freedom, calculate your ideal annual spending and multiply it by 25. This formula assumes a sustainable 4% post-tax return, allowing you to live off the gains indefinitely.

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered) thumbnail

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered)

My First Million·3 days ago

Marrying the Wrong Person Stems from Pretending to Be Someone You're Not

The surest path to an unhappy marriage is building a relationship where you are constantly playing a character to win the other person over. A true partnership is found when someone loves you for your authentic self, flaws and all.

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered) thumbnail

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered)

My First Million·3 days ago

A Billionaire's Success Requires High Character to Build a Network of Allies

Contrary to the 'evil billionaire' trope, Scott Galloway asserts that immense success requires building a network of allies who will put you in rooms of opportunity. This is impossible to sustain without possessing high character and fostering positive relationships.

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered) thumbnail

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered)

My First Million·3 days ago

Instead of Asking 'How Can I Help?', Offer Direct, Tangible Help

Asking someone in crisis if they need help can force them to admit vulnerability. A more powerful and kind approach is to anticipate their needs (e.g., money after an arrest) and provide help directly without being asked.

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered) thumbnail

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered)

My First Million·3 days ago

Fractional Jet Ownership Is the Ultimate Quality-of-Life Purchase

Galloway claims fractional jet ownership is his best expenditure, saving him 17 days a year and enabling spontaneous, memorable experiences. It 'lowers the bar for fun' by removing logistical friction, providing more value than even his house.

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered) thumbnail

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered)

My First Million·3 days ago

Scale from a Practice to an Enterprise by Hiring Talent to Leverage You

Galloway's key to scale is his ability to attract and retain great people who leverage his core talent. His team of 28 transforms his personal brand from a solo 'practice' into a scalable, high-value media 'enterprise'.

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered) thumbnail

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered)

My First Million·3 days ago

True Financial Freedom Is Eliminating the 'Should' Bucket from Your Life

Once you achieve economic security, real power isn't buying more things, but eliminating activities you do out of obligation or perceived expectation ('I should go'), versus necessity ('I have to') or genuine desire ('I want to').

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered) thumbnail

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered)

My First Million·3 days ago

U.S. Fiscal Policy Systematically Transfers Wealth From Young to Old People

Galloway argues tax policies like capital gains and mortgage interest deductions disproportionately benefit older asset-holders. He proposes eliminating them and creating tax holidays for people under 30 to combat generational wealth inequality.

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered) thumbnail

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered)

My First Million·3 days ago

GLP-1 Drugs Are More Transformative to the U.S. Economy Than AI

Scott Galloway argues GLP-1 drugs (like Ozempic) will have a greater societal impact than AI. By tackling obesity, they could halve U.S. healthcare costs, help solve the deficit, and even curb addictions, making them a profoundly transformative technology.

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered) thumbnail

Asking Scott Galloway 10 Questions We’re Not Allowed To Ask (unfiltered)

My First Million·3 days ago