Bill Gurley is a Wall Street and Silicon Valley legend. He’s the analyst who led the Amazon IPO and went on to become one of the most successful VCs of all time and an early investor in Uber, Zillow, and GrubHub. Today, he joins Nicole to answer the biggest questions on investors' minds right now.

Bill doesn't mince words: yes, we're in an AI bubble— and he explains exactly why, from circular spending deals that smell like Enron to the speculative behavior that always follows a real wave of innovation. He breaks down why the IPO system is rigged against retail investors, what tokenization could do to fix it, and what a SpaceX IPO would actually mean for everyday investors. He also shares the one market sector he thinks is quietly becoming a buy, and the specific Chinese battery stock he personally owns.

Then the conversation shifts to Bill's new book, Runnin’ Down a Dream, and his surprisingly personal framework for building a career you actually love. He shares the question he asked himself twice that changed the entire course of his life, his research on career regret, and why chasing passion is a competitive advantage.

Check out Nicole’s financial literacy course The Money School 

Find a Financial Advisor or Financial Coach from Nicole’s company Private Wealth Collective

Watch video clips from the pod on Money Rehab’s Instagram and Nicole Lapin’s Instagram

Get Bill's book Runnin’ Down a Dream 

Here's what Nicole covers with Bill: 

00:00 Are You Ready for Some Money Rehab? 

01:12 SpaceX + xAI: What Elon's Deal Really Means 

03:18 Why Retail Investors Keep Getting Shut Out of the Best Companies 

05:55 The IPO System Is Rigged 

08:36 Inside the Amazon IPO

10:40 Are We in an AI Bubble? 

16:30 AI vs. the Dot-Com Bubble

21:15 Which AI Tools Bill Actually Uses 

22:00 Bill's Take on AGI Hype 

23:30 Where Bill Sees Opportunity Outside of Tech 

27:30 The Chinese Battery Stock Bill Personally Owns 

28:45 How to Evaluate Stock Options as an Employee 

31:50 The Hidden Value of Joining a Fast-Growing Company 

33:15 Buy Side vs. Sell Side Analysts 

35:40 The Question That Changed Bill's Career Twice 

38:00 Why Following Your Passion Is a Competitive Advantage 

42:00 How Tito's Vodka Started with a Blank Sheet of Paper 

45:20 Bill's Next Chapter: A Policy Institute 

48:00 Nuclear Energy, Healthcare, and the Issues Bill Wants to Fix 

51:06 Bill Gurley's Tip You Can Take Straight to the Bank

All investing involves the risk of loss, including loss of principal. This podcast is for informational purposes only and does not constitute financial, investment, or legal advice. Always do your own research and consult a licensed financial advisor before making any financial decisions.

President Trump wants to cap credit card interest rates at 10%, and if you're one of the millions of Americans drowning in credit card debt, that sounds like a dream. But Nicole breaks down why this proposal might not be the hero story it seems, and what you should actually be doing right now while Washington debates.

Nicole explains the real reason a rate cap could backfire, why people with lower credit scores could end up worse off, and the actionable moves you can make today (no legislation required). From the debt avalanche method to balance transfers, personal loans, and a surprisingly simple phone call that could save you thousands, this episode is your full playbook for escaping the high-interest debt trap.

Check out Nicole’s financial literacy course The Money School 

Find a Financial Advisor or Financial Coach from Nicole’s company Private Wealth Collective

Watch video clips from the pod on Money Rehab’s Instagram and Nicole Lapin’s Instagram

Here's what Nicole covers today: 

00:00 Are You Ready for Some Money Rehab? 

00:16 Trump's 10% Credit Card Rate Cap, Explained 

01:17 Why This Isn't the Win It Sounds Like 

02:10 Who Could Lose Access to Credit Entirely 

02:52 The Payday Loan Trap Nobody's Talking About 

03:12 What You Can Do Right Now 

03:53 Know Your APR 

04:31 The Debt Avalanche Method 

05:09 Balance Transfer Cards and Consolidation Loans 

06:27 How to Negotiate Your Interest Rate 

07:01 Why Even $25 Extra a Month Matters 

07:41 Tip You Can Take Straight to the Bank

All investing involves the risk of loss, including loss of principal. This podcast is for informational purposes only and does not constitute financial, investment, or legal advice. Always do your own research and consult a licensed financial advisor before making any financial decisions.

Behavioral scientist and bestselling author Jon Levy is back to unpack how we can leverage our own psychology to build wealth. He explains why publicly announcing your financial goals can actually sabotage them, how “if-then” plans outperform willpower, and why adopting the identity of “I’m an investor” can become a self-fulfilling prophecy. Then Nicole asks Jon what the science says about whether jerks make better CEOs, and he shares research-backed strategies for becoming a stronger leader.

He also gets personal: how growing up as the child of immigrants affected his money mindset, the road to becoming debt-free in eight years, and the amount of money he needs in his bank account to feel safe. Nicole and Jon also discuss how financial frameworks like the sunk cost fallacy apply to relationships and whether your partner might be the best investment you’ll ever make.

Check out Nicole’s financial literacy course The Money School 

Find a Financial Advisor or Financial Coach from Nicole’s company Private Wealth Collective

Watch video clips from the pod on Money Rehab’s Instagram and Nicole Lapin’s Instagram

Get Jon’s latest book Team Intelligence 

Here’s what Nicole covers with Jon:

00:00 Are You Ready for Some Money Rehab? 

01:47 Jon’s Famous Dinners Explained 

04:17 Why Money is a Mental Puzzle, Not a Math Problem 

06:16 Why Sharing Goals Fails 

07:56 From Housing Markets to Dating Markets

09:42 Is Your Partner the Most Important Financial Decision You’ll Make? 

15:09 Jon’s Leap From Debt to Social Currency 

33:37 Money Values in Marriage 

38:01 Should You Quit the Zombie Job?

39:27 The Chicken/Egg Problem with Success 

45:25 Do CEOs Need to Be Jerks to be Successful? 

49:53 What Makes a Leader 

58:12 How Self Deprecation Erodes Trust 

01:06:57 Jon Levy’s Tip You Can Take Straight to the Bank 

Four-year college isn’t the default anymore…  but saving for your kid’s future absolutely is.

Today, Nicole breaks down the modern playbook for affording college whether your kid is a newborn, or if they’re applying to colleges now. This is your simple guide to 529 plans, custodial accounts, Coverdells, prepaid tuition plans, and the newest government-backed savings option making headlines. If you’ve ever wondered, “What happens to a 529 plan if my kid doesn’t go to college?” Nicole will teach you a smart move there, too.

Check out Nicole’s financial literacy course The Money School 

Find a Financial Advisor or Financial Coach from Nicole’s company Private Wealth Collective

Watch video clips from the pod on Money Rehab’s Instagram and Nicole Lapin’s Instagram

Here’s what Nicole covers today:

00:00 Are You Ready for Some Money Rehab?

01:11 Where To Start If You Have a Newborn

01:28 Everything You Need to Know About 529s

04:44 Where To Start If Your Kid Is in Grade School

05:42 The Pros and Cons of Custodial Accounts

08:17 Where to Start if Your Kid Is in High School

10:32 Tip You Can Take Straight to the Bank

All investing involves risk, including loss of principal. This episode is for informational purposes only and does not constitute financial, investment, or legal advice. Always consult a licensed professional before making financial decisions.

Lucy Guo built one of the most talked-about AI companies in the world before most people finish college. Then, she made headlines when she dethroned Taylor Swift as the youngest self-made female billionaire. Today, she joins Nicole to talk about how she grew wealth, and how you can borrow the money lessons that only show up after you’ve already “made it.” 

Lucy tells Nicole about growing up bullied for not being able to afford the cool brands, scrappy strategies she used to save money when she was building her first company, and navigating the strange attention of being labeled a billionaire while most of that wealth still isn’t liquid. She explains the routines that kept her disciplined, the hard boundaries she set around lending money after getting burned, and stories of her wild money hacks like booking refundable flights to eat free meals in the airport lounges. 

Nicole and Lucy also dive into the hidden playbook of startup money and the creator economy: how Lucy’s fundraising secret is to manufacture FOMO, why the wealthy borrow instead of sell, and the monetization strategy all creators should adopt. 

Check out Nicole’s financial literacy course The Money School 

Find a Financial Advisor or Financial Coach from Nicole’s company Private Wealth Collective

Watch video clips from the pod on Money Rehab’s Instagram and Nicole Lapin’s Instagram

Keep up with Lucy on Instagram and learn more about Passes

Here’s what Nicole covers with Lucy:
00:00 Are You Ready for Some Money Rehab?

01:17 Lucy’s Routine and the Impact of Success on Hustle

03:39 Childhood Bullying05:08 Lucy’s Confidence Reset

08:20 Unpacking “Paper Wealth” and Liquidity

13:40 Should You Lend Money to Friends?

14:35 Lucy’s Investing Thesis

18:34 FOMO Strategy in Fundraising

22:22 Billionaire Money Tips

25:03 The Robbery Attempt

27:38 Money Saving Hacks

33:43 Stigma Around “Work Hard, Play Hard”

37:24 Passes and the Creator Economy

53:45 Lucy Guo’s Tip You Can Take Straight to the Bank

Today, Nicole breaks down the viral tax strategy everyone on social media is talking about — the claim that buying a short-term rental can legally wipe out your taxes.

She explains the simple idea behind bonus depreciation, why it creates massive upfront write-offs, and how real estate investors use upgrades and accounting strategy to dramatically lower taxable income. But she also pulls back the curtain on the part influencers skip: why a $0 tax bill doesn’t automatically mean you made money, how much cash you still need to spend, and the risks hiding behind the hype.

The Money Rehab Episode About Whether Home Ownership is Overrated  

Check out Nicole’s financial literacy course The Money School 

Find a Financial Advisor or Financial Coach from Nicole’s company Private Wealth Collective

Watch video clips from the pod on Money Rehab’s Instagram and Nicole Lapin’s Instagram

00:00 Are You Ready for Some Money Rehab? 

00:53 Bonus Depreciation 101

03:10 What Changed with the  Big Beautiful Bill

03:38 What Qualifies (and What Doesn’t)

04:22 Fact-Checking the Viral Airbnb Example 

05:37 The Caveats

05:54 Cost Segregation Study Workaround

07:36 Don’t Let the Tax Tail Wag the Dog’ 

09:10 Tip You Can Take Straight to the Bank

Neil Patel’s origin story involves borrowing from his parents’ life savings to keep his startup alive. Not only did his plan work, but he built a million-dollar company, advised companies including Amazon, Google, and Microsoft— and, he paid his parents back.

Today, Neil breaks down the money lessons he learned once he made it big. He shares why he still drives a minivan despite being able to afford something bougie, the unusual way he teaches his kids about taxes, and the important distinction he makes between success and wealth.

Then, Nicole and Neil get tactical and dig into the future of getting discovered online. Neil explains why traditional search is dead and how to adapt, what founders can do if they have a $0 marketing budget, and the SEO do’s and don’ts of naming your business. 

Check out Nicole’s financial literacy course The Money School 

Find a Financial Advisor or Financial Coach from Nicole’s company Private Wealth Collective

Watch video clips from the pod on Money Rehab’s Instagram and Nicole Lapin’s Instagram

Check out Answer the Public, the free tool Neil mentioned in this conversation

Find more of Neil’s work and resources here

Here’s what Nicole covers with Neil:

00:00 Are You Ready for Some Money Rehab?

01:09 Launching Crazy Egg and Borrowing From Parents

06:42 Next Ventures and Kissmetrics 

09:43 Do’s and Don’ts of Naming Businesses

15:31 NP Digital’s Massive Success vs Personal Success

21:19 Neil’s Perspective on Wealth, and the “Big R” Framework

29:32 Hot Takes on Money

30:07 Teaching Taxes Through Ice Cream

32:15 Living with Less and Financial Goals

38:45 Trust Funds and Regrets

42:09 Actionable Digital Marketing Advice for Business Owners

42:26 Choose Your Fighter: Email List, Website or Instagram?

44:59 Why Traditional Search is Dead

46:59 SEO vs AEO

55:29 Marketing Tips for a $0 Budget

01:00:49 Tip You Can Take Straight to the Bank

Millions of pages from the Epstein files have been unsealed, but they leave behind even more unanswered questions about how the money and criminal network actually worked. Today, Nicole traces the financial trail behind Jeffrey Epstein’s fortune—what we know, what prosecutors could never fully explain, and how a man with no real business amassed hundreds of millions of dollars.

Nicole breaks down Epstein’s mysterious rise from Wall Street suit to shadowy “financial consultant,” the ultra-wealthy clients who funded the majority of his income, and the explosive reputational fallout that continues to ripple across corporations, universities, and global power players. She also sets straight the rumors that Epstein created Bitcoin, and explains the real financial consequences of association in today’s markets.

Check out Nicole’s financial literacy course The Money School 

Find a Financial Advisor or Financial Coach from Nicole’s company Private Wealth Collective

Watch video clips from the pod on Money Rehab’s Instagram and Nicole Lapin’s Instagram

Here’s what Nicole covers today:

00:00 Are You Ready for Some Money Rehab?

00:18 The Epstein Files: A Who's Who of Power

00:58 Following Epstein's Money Trail

04:42 Financial Fallout of the Epstein Files

06:20 The Bitcoin Theory

07:28 Ongoing Legal Battles and Reputational Risks

09:22 The Power of Survivors

All investing involves the risk of loss, including loss of principal. This podcast is for informational purposes only and does not constitute financial, investment, or legal advice. Always do your own research and consult a licensed financial advisor before making any financial decisions or investments.

For some collectors, art is about beauty, meaning, and power. For others, it’s a convenient place to clean dirty money.

Today, Nicole breaks down the hidden financial playbook behind the global art market, and why some billionaires treat paintings less like décor and more like offshore bank accounts. From subjective valuations and private appraisals to tax-free warehouses, art-backed loans, and regulatory gray zones, this episode walks through the exact five-step system the ultra-wealthy can use to store, grow, and sometimes quietly clean massive amounts of cash.

You’ll hear how a $5 million painting can magically become a $20 million asset on paper, why some of the world’s most valuable art never leaves storage, and how auction houses legally facilitate transactions that banks never could. Then Nicole pulls it back to real life — what this reveals about how wealth actually moves, why valuation is often narrative-driven, and how everyday investors can borrow the thinking without needing a Picasso or a private jet.

Check out Nicole’s financial literacy course The Money School 

Find a Financial Advisor or Financial Coach from Nicole’s company Private Wealth Collective

Watch video clips from the pod on Money Rehab’s Instagram and Nicole Lapin’s Instagram

Here’s what Nicole covers today:

00:00 Are You Ready for Some Money Rehab?

00:18 Art as an Investment

01:14 How the Wealthy Buy Art 

02:18 Freeports and Tax Havens 

03:20 Reappraisal and Inflating Art Value 

04:46 Using Art as a Financial Tool 

06:16 Money Laundering Through Art 

07:16 Lessons for Everyday Investors 

08:17 Investing in Art Without Millions 

All investing involves the risk of loss, including loss of principal. This podcast is for informational purposes only and does not constitute financial, investment, or legal advice. Always do your own research and consult a licensed financial advisor before making any financial decisions or investments.

Your first $100,000 in investing feels impossible—until you see the math. Today, Nicole breaks down why the first $100K is the hardest money you’ll ever make, what changes mathematically once you cross it, and the path to get there… without a hot stock tip, crypto bro, or dumb luck.

Nicole walks through a real, doable five-year plan based on the average U.S. salary —including exactly how much to invest each month, where to put your money, and how the beautiful power of compound interest quietly accelerates behind the scenes. 

Try Nicole’s Compound Interest Calculator

Check out Nicole’s financial literacy course The Money School 

Find a Financial Advisor or Financial Coach from Nicole’s company Private Wealth Collective

Watch video clips from the pod on Money Rehab’s Instagram and Nicole Lapin’s Instagram

Here’s what Nicole covers today:

00:00 Are You Ready for Some Money Rehab?

00:18 Why Your First $100K Is the Hardest

02:53 Year-by-Year Investment Plan

03:05 Year 1: Building the Habit

04:00 Year 2: Gaining Momentum

04:33 Year 3: Growth Year

04:59 Year 4: Push Harder

05:37 Year 5: Reaching the Goal

06:00 Reality Check: Life Throws Curveballs

06:33 Passive Income

07:20 Your Next Steps and Resources

All investing involves the risk of loss, including loss of principal. This podcast is for informational purposes only and does not constitute financial, investment, or legal advice. Always do your own research and consult a licensed financial advisor before making any financial decisions or investments.