Money, Investing & Wealth — what 90 operators said

The episodes

How to Build a Profitable Turo Rental Fleet with George Madden

Building Wealth With Other People’s Money: Justin Brennan on Multifamily Real Estate

From Broke to Six Figures and Back: Jason Brown on Options Trading, Risk and Rebuilding Wealth

Why Is Your Best-Selling Product Losing You Money?

Build Wealth the Boring Way: Passive Income, Trust and Better Leads With Dani Lynn Robison

The Mental Performance Framework for High-Pressure Decisions

Most Businesses Should Never Raise Venture Capital | Navin Goyal

The Legal Tax Moves That Help Rich People Get Richer | Mark J. Kohler

Founder Lessons From Scaling, Going Public, and Rebuilding | Rick Jordan

How a Viral Congressional Trading Tracker Became a $1B+ Fintech Business | Autopilot

How Unregulated Gambling Is Draining BILLIONS From the U.S. Economy | Ismail Vali

The Business of NIL: Parents, Brands, and the Power Behind College Sports | Justin J. Giangrande

The $2.5M Problem No One Is Planning For: AI, Aging, and Your Financial Future with Lily Vittayarukskul

What Second-Order Effects From the Iran War and AI Mean for Your Business | Ben Johnston with Kaptus

The Mental Blind Spot That’s Costing You Money and Affecting Your Business Decisions | Anders Hansen

How Ken Goldin Built a $500M Market: Attention, Hype & the Business of Collectibles

No One Is Coming to Save You: How Jamil Damji Took Control of His Life & Built a Real Estate Empire

Questions answered on money, investing & wealth

What is Tom Brady's stake in Card Vault and why did the company rebrand?

In their words

You've got to have a bit of crypto, stocks, gold, bonds, real estate. And you also need a second passport because all of these things, if you're really in a one passport, they're tied to one nationality. That's not diversification.

Jeremy Savory · Destination Citizenship: Navigating Global Mobility (40:23)

I started with $3,000 investment in real estate 28 years ago, and that is $4 billion worth of real estate today.

Grant Cardone · Making Real Estate Investing Approachable For The Ma (3:19)

I think a lot of people who started investing just the last few years, whether it's real estate, crypto, bond stocks, they didn't realize that all that stuff could go down as well as go up.

Rob Luna · Rob Luna - Business and Wealth Strategist (1:09)

If you want to invest in short-term rentals, long-term rentals, do real estate and deploy money in real estate, it's not for everybody, but we have depreciation strategies and investment strategies that can offset my income over here.

Mark J. Kohler · The Legal Tax Moves That Help Rich People Get Richer (6:28)

Because with wealth comes freedom. And that's what we're all after at the end of the day. So to say that money doesn't matter to you. It's probably just you lying to others and you lying to yourself.

Brett McDermott · Make Millions with the Art of Charisma with Brett Mc (23:50)

And the tough thing about marketing too of like building a brand and getting into real estate because here's the thing also with real estate is I could buy a million dollars of real estate.

Pace Morby · Mindset vs Skillset: The Secret to Business Success (33:05)

So there's really no difference in raising money from investors to buy cash flowing businesses or buy real estate assets, because at the end of the day, real estate is a business.

Brad Blazar · Big Brass Balls and a Bag of Cash with Brad Blazar (14:35)

We believe through autopilot, if you enjoy investing, if you do thesis driven investing, you can make money by launching your personal skill set, your personal portfolio via the platform.

Chris Josephs · How a Viral Congressional Trading Tracker Became a $ (19:56)

I like to say follow the money. At the time of this recording, the money is going into AI, is going into semiconductor stocks, is going into cloud and storage.

Jason Brown · From Student Loans to Millionaire: Jason Brown’s Jou (19:11)

They think wealth is Lamborghini. They think it's flash. They think it's private jets and cars. And here I'm the opposite. I'm a minimalist.

Adrian Brambila · Living in a Van to a Millionaire: How Mindset Impact (2:23)

I think at this point, it's fair to say it's an accepted investment vehicle.

Chris Hanson · NO BS Business News: Top 10 Mother's Day Gifts - Ama (24:17)

Again, the real estate investment is the best investment in terms of tax benefits.

Ryan Moriarty · Death & Taxes: Maximize your Business’ Money with Ry (26:15)

What comes up again and again

There is no separate "crypto tax" - crypto is treated like dollars, the IRS has a crypto task force, and gains can be sheltered by holding crypto inside a Roth or self-directed IRA. (The Legal Tax Moves That Help Rich Peopl)
Real diversification means spreading across crypto, stocks, gold, bonds and real estate — and holding more than one nationality, since single-passport holders have all assets tied to one government. (Destination Citizenship: Navigating Glob)
Crypto is a short-term roller coaster: Bitcoin sat around $93,900 on recording day and XRP swung up 20% then back down 10% for only a 3-4% net weekly change, after news of a federal crypto reserve naming XRP, Solana, Ethereum and Bitcoin. (BUSINESS NEWS & TRENDS: The Rise of Trad)
Crypto is in a holding pattern: Bitcoin under $100K after a roughly 15% pump two weeks earlier, XRP near $2.15, and Chris naming Solana and Dogecoin as his non-Bitcoin picks. (NO BS Business News: Top 10 Mother's Day)
Wealth requires all three skills - earning income, living under your means to save, and investing with diversification. The Austin founder who put an entire $13 million exit into Bitcoin is the cautionary case. (Living in a Van to a Millionaire: How Mi)
Crypto cards let you load Bitcoin onto a Visa and spend it anywhere Visa is accepted; Shopify merchants can also accept Bitcoin or Ethereum at checkout. (Crypto Investing Advice, Trump Crypto Pl)
Chris argues a former president speaking at the Bitcoin conference is a legitimacy signal that can give retail investors and older, more skeptical buyers more confidence in crypto as an investment. (Weekly Business News for Aug 2 | MAGA, K)
Bitcoin breaking $60,000 is being driven less by retail hype and more by access: JP Morgan and other big institutions offering Bitcoin plus approved ETFs mean financial advisors can now put 5-10% of a client's holdings into crypto. (The Week of March 1 2024 | Wendy’s Will )
Flips, wholesaling, and short-term rentals are legitimate, but recurring-rent assets are what build the long-term generational wealth most people say they want. (Building Wealth With Other People’s Mone)
Autopilot charges a flat yearly subscription per portfolio followed (about $100 to follow Pelosi's filings, $200 for the Wharton AI PhD strategy) rather than a percentage of assets under management. (How a Viral Congressional Trading Tracke)

Questions this topic answers

All 177 episodes

Search within

Oct 2, 2026

Is Bitcoin now a safe investment compared to stocks?

Is real estate investing really passive income?

What is OPM in real estate investing?

How do you transition from a W2 job to full-time real estate investing?

What is the difference between active and passive real estate investing?

Why do most people fail at real estate investing?

Why is the crypto market stalling even with pro-crypto policy?

How should a beginner start investing in crypto?

All 177 episodes

How to Build a Profitable Turo Fleet With George Madden

Justin Brennan on Multifamily and Other People's Money

Jason Brown on Options Trading, Risk and Rebuilding

Why Great Products Still Lose Customers: Lisa Holladay

Why Your Best-Selling Product Is Losing You Money

Dani Lynn Robison on Boring Wealth and Better Leads

Evan Marks on Mental Performance Under Pressure

Why Most Businesses Should Never Raise Venture Capital

Legal Tax Moves That Help the Rich Get Richer

Rick Jordan on Going Public, Failing, and Rebuilding

Pelosi Tracker to $1B Fintech: Chris Josephs of Autopilot

Inside the $97B Unregulated Online Gambling Market

The Business of NIL with Justin J. Giangrande

AI, Aging, and the $2.5M Long-Term Care Problem

Iran War, AI and the Small Business Economy

Anders Hansen: The Mental Blind Spot Costing You Money

Ken Goldin on Attention, Hype and Collectibles

Jamil Damji: No One Is Coming to Save You

Kaylor Betts: Stop Consuming, Start Winning

Mr. Biz on Cash Flow, Budgets and Scaling to $50M

Mike Sancho: From Expelled to Passive Income Builder

Alex Morton on Building Wealth Young and Losing It All

Inside the Rental Car Business with George Madden

Mark J. Kohler on How the Rich Use Tax Strategy

Matt Higgins: Why a Plan B Kills Your Plan A

Brad Blazar on Raising Capital With Other People's Money

Brevin Galloway on D1 Basketball, NIL and Mental Health

Ryan Stewman on Inflation, Taxes and Interest Rates

Grant Cardone: Real Estate Investing for Everyday People

Jason Brown: From Student Loans to Stock Market Millionaire

David Gardner on Rule Breaker Investing

Building Real Estate Wealth With Other People's Money

Right About Now Evolves: Collectibles on SI Launches

Amrinder Kamboj on Acquisitions, Equity and Scaling

Railroad Merger, Prebiotic Pepsi and TikTok's 60-Min Test

Influencer ROI, Attention Arbitrage and Tax Strategy

Stripe Skips IPO, Amazon's Dark Patterns, AI Umpires

Tariffs, GPT-5, Prime Day and Frozen Fed Rates

4th of July Business News From the Houseboat

Dani Lynn Robison on Passive Real Estate Income