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Afford Anything

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

Afford Anything

Paula Pant | Cumulus Podcast Network

Entrepreneurship, Business, Investing

4.6 β€’ 3.4K Ratings

πŸ—“οΈ 16 May 2025

⏱️ 87 minutes

🧾️ Download transcript

Summary

#608: 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 β€” 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 β€” 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 β€” 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 β€” 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 β€” 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 β€” focusing only on opportunities with enough potential impact β€” helps prioritize time and delegate effectively. At 82, he still practices these principles daily, considering himself "biologically more like 70 and getting younger." Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0

He lost 100,000 on his first deal and made 100 million on his second.

0:04.9

He was able to do that because he says he was born a natural stoic.

0:08.7

And in today's episode, we're going to learn what that means and why it matters to any goal that you want to achieve.

0:14.6

Welcome to the Afford Anything podcast, the show that knows you can afford anything but not everything.

0:19.3

Every choice carries a tradeoff.

0:20.9

This show covers five pillars.

0:22.4

Financial Psychology, Increasing Your Income, Investing, Real Estate and Entrepreneurship.

0:26.0

It's double-eye fire.

0:27.4

I'm your host, Paula Pant, I trained in Economic Reporting at Columbia.

0:30.3

And today's guest is Robert Rosencrantz, an 82-year-old billionaire, investor, entrepreneur, and philanthropist,

0:37.4

who says that stoicism and the

0:40.0

stoic philosophy is a major part of what got him to where he is. Robert came from a family

0:46.3

that lived paycheck to paycheck. His dad was unemployed for two years, and his mom worked as a clerk

0:51.4

at the drugstore. Growing up, he felt the financial insecurity of never knowing if they were going to cut off

0:57.0

the electricity, cut off the telephone line.

1:00.1

And it was through that that he learned to be stoic, and he learned that the obstacle is the

1:04.5

way.

1:05.3

By the time he was 14, he began buying stock investments, and by the time he was 35, he had

1:10.6

built a net worth of

1:11.6

$400,000. That's the equivalent in today's dollars with inflation of about $4 million.

1:17.8

It was at that time that he made a extremely high-stakes business decision that would change

1:24.5

everything. In this upcoming conversation, he shares his story.

...

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