Afford Anything

Category: Episodes

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#616: How Hackers Are Stealing Your Retirement $50 at a Time, with former CIA hacker Dr. Eric Cole

Two school teachers in Ohio saved their entire lives for one dream — buying a farm.

When they inherited $1.3 million and found the perfect property for $1.2 million, everything seemed perfect.

Five days before closing, they received what looked like a legitimate email from their closing company with wire transfer instructions. They sent the money and showed up at closing, only to discover they’d been scammed.

The email was fake, sent by hackers who had infiltrated the closing company’s servers for months, waiting for exactly this type of high-value cash deal.

That story comes from cybersecurity expert Dr. Eric Cole, who joins us to explain why ordinary people have become prime targets for cybercriminals.
Cole, a former CIA hacker who served as cybersecurity commissioner under President Barack Obama and advises high-profile clients including Bill Gates’ personal estate, has a message: if you think you’re too small to be targeted, you’re wrong.

While billion-dollar companies deploy teams of 60 cybersecurity professionals, you have virtually no protection.

Criminals know this. They’re not trying to steal $100 million from one person anymore — they’re stealing $50 from thousands of people every month.

You probably won’t notice the small amounts vanishing from your accounts. Cole calls it “death by a thousand cuts,” and it’s happening right now.

We talk through the most common attacks targeting your money. Bank hacking is simpler than most people realize. All criminals need is your account number — printed on every check you write — and your password. With that information, they can often perform electronic fund transfers of up to 50 percent of your account balance without triggering alerts.

We also cover the China-TikTok connection, secure messaging options, and why Cole helped configure President Obama’s smartphone to connect to fake cell towers that masked his actual location.

Cole’s bottom line: cybersecurity isn’t just for tech companies anymore. Criminals are targeting ordinary people because we’re easier prey than heavily protected corporations. Your money is under threat. Here’s how to protect it.

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#615: Q&A: We Saved $1.2 Million But We’re Still Renting. Should We Buy?

Emily is nervous that buying their first home will derail her family’s journey to financial independence. What’s the smartest way to deploy their savings and stay on track?

Based on cap rate calculations, Paul’s real estate investments have appreciated beyond their sensible holding point. Should he sell his assets, or is there more to consider here?

Mike is recently retired while his wife still works. With a paid-off home and healthcare already taken care of, what are best practices for drawing down an investment portfolio?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

P.S. Got a question? Leave it here.

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#613: Rachel Rodgers: This Multimillionaire Started With $330,000 in Debt and a $41,000 Salary

Rachel Rodgers graduated from law school with $330,000 in student loans. Her starting salary? Just $41,000.

Most people would have accepted this crushing debt-to-income ratio. They’d slowly chip away at payments for decades. Rodgers had a different plan.

She deferred her loans and started her own virtual law practice in 2008 — during the recession, when jobs were scarce and most lawyers were struggling to find work.

Her mom thought she was crazy.

Her first year, she made around $65,000 in gross revenue with only $300 in overhead costs. By year two, she was earning $300,000.

The key to her success wasn’t cutting expenses or living on rice and beans. Rodgers focused entirely on earning more money.

We talk about the practical steps she took to scale her business.

She waited until hitting $250,000 in annual revenue before bringing on her first full-time employee — an administrative assistant who immediately paid for herself by responding to client inquiries faster than Rodgers could manage alone.

Rodgers also shares insights from a CEO’s perspective on what employees should know when asking for a raise.

Understand your company’s goals. Know your boss’s pain points. When you spot a problem, bring three solutions — not just the issue. She usually goes with whatever option her team recommends.

“You are the asset,” she explains. This mindset applies whether you’re an entrepreneur or an employee trying to maximize your career potential.

Our interview covers her transition from solopreneur to multimillion-dollar business owner, her approach to leading employees, and her philosophy on building wealth through entrepreneurship rather than cost-cutting.

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#612: How to Know If You’re Cut Out for Entrepreneurship Before You Risk Everything, with Grant Sabatier

Grant Sabatier never worked in retail, never worked in a bookstore, and had no idea what he was doing when he opened Clintonville Books in Columbus, Ohio.

But that’s exactly the point.

The experiment required 1,200 hours of solo work — measuring spaces, moving 40,000 books, and navigating city regulations.

But it taught him something crucial: even experienced entrepreneurs face steep learning curves when they try something new.

The serial entrepreneur and author of “Inner Entrepreneur” joins us to share his unconventional journey from online businesses to brick-and-mortar retail.
He also explains why he believes everyone will become an entrepreneur within the next decade — whether they want to or not.

We dive deep into Sabatier’s framework for the four stages of entrepreneurship.

The first stage is experimental — you’re figuring out how entrepreneurship feels and testing ideas with minimal risk. Most people skip the crucial research phase and invest too much money too quickly.

The second stage focuses on building sustainable systems as a solopreneur. Thanks to AI and modern tools, Sabatier launched a new website in 10 minutes recently — something that would have taken two weeks just five years ago.

Stage three involves intentional growth. Sabatier warns against the common trap of scaling rapidly without considering how you want entrepreneurship to fit into your life.

The final stage is empire entrepreneurship — using cash flow from successful businesses to acquire other companies rather than investing in traditional assets like stocks or real estate.

Throughout our conversation, we explore the most common reasons businesses fail, how to avoid fragmented attention, and why Sabatier believes your story is your competitive advantage in an AI-driven world.

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#611: Q&A: “Is It REALLY Different This Time?”

With the state of the world changing so rapidly, Lesley is struggling to accept that “this time isn’t different.” Does the past still reliably inform the present in the face of major decisions today?

An anonymous caller and her husband want to achieve financial independence through real estate within 10 years. Is it better to pay off existing mortgages or prioritize buying more rentals?

Melanie feels duped by the FICO credit scoring system. She’s doing all the right things, but her credit score is still moving in the wrong direction. What’s going on here?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

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#610: Your Goals Might Be Killing You (Literally), with Sebastien Page

In 2005, Sebastien Page nearly died from a mysterious bacterial infection that doctors couldn’t diagnose for a week.

A single observant physician noticed cuts on his toes from running in wet terrain and connected the dots.

The experience forced Page to confront mortality — and completely changed how he thinks about goals.

Page, the chief investment officer at T. Rowe Price and author of The Psychology of Leadership, joins us to share why traditional goal-setting might be sabotaging your happiness.

He explains how 80 percent of millennials say they just want to get rich, and 50 percent want to become famous.

But research from Harvard’s 80-year longitudinal study reveals something surprising: people who climbed the social ladder weren’t meaningfully happier than those who struggled financially.

The real predictor of long-term happiness? The quality of your relationships with others.

We explore the dark side of goals through a concept called “goal-induced blindness.”

Page uses Mount Everest as an example — climbers have a 4 percent chance of dying, the same odds as eating four poisoned gummies out of 100. Yet people still attempt the summit because they become blinded by the goal itself.

Page shares his own experience with goal-induced blindness during his demanding career in money management. The relentless travel and pressure contributed to his near-fatal infection in 2005. He learned that working less actually made him more productive.

We dive into Page’s framework called the “three Cs”: core beliefs, curves, and control theory.

Core beliefs are the filters through which you interpret the world — like whether you trust people or believe money should be spent versus saved.

Curves refer to stress management, based on research showing optimal performance doesn’t happen at zero stress.

Control theory teaches you when to exercise “strategic patience” versus making quick decisions.

Page also introduces the PERMA framework from positive psychology: positive emotions, engagement, relationships, meaning, and accomplishment. He calls the last four “proteins for your soul,” while positive emotions are more like a sugar high.

The discussion covers practical applications for everything from hiring decisions to relationship choices, using mathematical concepts like net present value to make better life decisions.

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#609: Q&A: How Not To Screw Up Retirement Spending

Eva is approaching financial independence, but she’s worried about messing up the transition. How does she set her portfolio up for success during the drawdown years of early retirement?

Former financial planner Joe Saul-Sehy and I deep-dive into this question in today’s episode.

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#608: The Stoic Path to Wealth, with Billionaire Investor and Philanthropist Robert Rosenkrantz

At age seven, Robert Rosenkrantz made a decision that would shape his entire life: he would take full responsibility for his future.

As a child, Rosenkrantz watched his parents struggle financially. His father was unemployed for two years, and his mother worked as a drugstore clerk.

Their financial insecurity was painfully obvious to young Robert. He never knew if the electricity or telephone service would be shut off.

But rather than seeing this as an obstacle, he saw it as a path to self-reliance.

By age 14, Rosenkrantz was managing investments for his family. By 35, he had amassed $400,000 — equivalent to about $4 million today. Then came the pivotal moment that changed everything: a negotiation with wealthy entrepreneur Joe Mailman.

When Mailman expressed concerns about traditional investment structures that created a “heads you win, tails I lose” scenario, Rosenkrantz made a bold counter-offer. He put his entire liquid net worth at risk in exchange for a 50/50 profit split with no carried interest.

“First deal, we lost $100,000. The second one, we made $100 million,” Rosenkrantz says during the interview. “So it averaged out.”

Now 82, Rosenkrantz joins us to discuss his book, “The Stoic Capitalist,” and the principles that guided his career.

For over 35 years, he’s carried the same negotiation card from “Getting to Yes” in his wallet — a reminder that negotiation isn’t about winning, but solving problems together.

We talk about his counterintuitive investment philosophy: look for companies that require minimal specialized talent, like laundromats or self-storage facilities. He says these often make better investments than those needing exceptional management, like restaurants.

This principle guided his first major success, a lawn and garden products business that essentially put dirt in bags — a simple operation that became a regional monopoly and eventually sold for $100 million.

Today, Rosenkrantz funds scientific research on longevity and hosts debate programs that present balanced perspectives on contentious issues. His philanthropy includes backing a groundbreaking study that has extended worm lifespans from 15 days to over 250 days — potentially the longest lifespan extension ever achieved in any organism.

When asked about retirement, he responds: “How do you spell that?”

His advice for decision-making comes straight from stoic philosophy: focus only on what you can control — the present and future, not the past. This means disregarding sunk costs completely when making decisions and using reason to regulate emotions.

For Rosenkrantz, counting the zeros — focusing only on opportunities with enough potential impact — helps prioritize time and delegate effectively. At 82, he still practices these principles daily, considering himself “biologically more like 70 and getting younger.”

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#607: Q&A: Remember When Money Advice Came From Just One Book at the Library?

George is a worried baby boomer, wondering if today’s generation is drowning in the noise of today’s financial landscape. How does one find a balance between information and overload?

Heather is stunned by the notion that renting could make more financial sense than buying. Where she’s from, the numbers seem to always swing in favor of owning. What’s she missing?

Former financial planner Joe Saul-Sehy and I tackle these questions in today’s episode.

Enjoy!

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