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First Friday: AI, Debt, and a Social Security Shortfall. Should Your Money Plans Change? With Rob Berger

#755: Many retirees fear running out of money more than they fear dying. AI is reshaping the economy, the U.S. now spends over $1 trillion on interest, and Social Security faces a shortfall. Rob Berger says if you're worried about all that, it's a sign you're thinking clearly. Rob Berger is a former securities lawyer, founder of the personal finance site Dough Roller, and host of a nearly 300,000-subscriber YouTube channel on investing and retirement planning. He started writing about money in 2007, just months before the Great Recession. In this episode, we discuss: How to tell whether today's high stock prices should change your plan When to trim a stock that's grown too big, and when to let it ride Why a booming economy can still leave so many people feeling squeezed What a looming Social Security shortfall could mean for your retirement How to cover your basic bills with guaranteed income, whatever markets do How to ease into retirement instead of going from 40 hours to zero Why daily spending habits matter more than investing knowledge Whether you're five years from retirement or five years into your career, this episode will help you separate what's truly changing from what never does. 🔗 RESOURCES MENTIONED RETIREMENT WORRIES FEEL OVERWHELMING? SEE YOUR WHOLE FINANCIAL PICTURE ON ONE PAGE 👉 http://affordanything.com/cornerstone Rob Berger on YouTube 👉 https://www.youtube.com/channel/UC9C17-OMxa-7oRSaCtztObw Rob's free weekly retirement newsletter 👉 https://robberger.com/newsletter Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Episoder(805)

My Bank Account Hit Zero ... Then I Got Rich -- with Jaspreet Singh of Minority Mindset

#759: At 19, Jaspreet Singh bought a rental for $8,000. What followed was a nightmare tenant, a lawsuit, and a later house stripped of its copper, and it taught him what the real estate books leave ou...

16 Okt 1h 42min

Q&A: "I’m 26 and No Longer Motivated by Money. Am I Unemployable?”

#758: Joe says that if you tell an employer you’re not motivated by money, you’re unemployable. Paula says that’s exactly the person she wants to hire. Former financial planner Joe Saul-Sehy joins Pa...

13 Okt 1h 12min

Steve Jobs Hated the Name “Genius Bar.” How He Came Around, with Ron Johnson

#757: Ron Johnson is the creator of the Apple Stores and former CEO of JCPenney. At age 24 Ron Johnson turned down a $120,000 Goldman Sachs offer to unload trucks for $40,000, and that detour led Stev...

9 Okt 1h 48min

How Losing $500K in ‘08 Led One Trader to a Different Kind of Portfolio, with Jared Dillian

#756: In September 2008, Jared Dillian watched about half a million dollars of Lehman Brothers stock go to zero in a single week. He wasn't allowed to sell any of it. What he built afterward is a port...

6 Okt 52min

Q&A: We Have $80K in Cash and Want a 1–2 Year Sabbatical. Is It Enough?

#754: Four months of savings in the bank, a goal of eight, and a career break she's excited to fund. Does everything else really have to wait? Paula and Joe's answer: don't turn your emergency fund in...

29 Sep 1h 14min

Why 60,000 New York Apartments Sit Empty in a Housing Crisis, with Kenny Burgos

#753: New York City is short roughly half a million homes, yet at least 60,000 rent-regulated apartments sit empty. Under current rules, many owners lose less money by leaving them vacant than by fixi...

25 Sep 1h 25min

Q&A: I’m Tired of Managing My Rental Property. Should I Sell It?

#752: A caller's rental is performing fine, but a late-paying tenant and a roof replacement have her ready to sell it before she moves to Madrid for her MBA. Paula argues the real fix isn't selling — ...

22 Sep 1h