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.”
Timestamps:
Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.
(0:00) Intro
(2:00) Welcome and introduction to Robert Rosenkrantz
(4:00) The negotiation card from “Getting to Yes” in Rosenkrantz’s wallet
(5:00) Negotiation as problem-solving, not a contest
(7:00) Growing up on Upper West Side with financially insecure parents
(9:40) Becoming self-reliant at age seven
(13:40) First stock investment at age 14
(18:20) Managing family portfolio as a teenager
(22:40) Explanation of stoic philosophy principles
(29:00) Transition from $400k net worth to major wealth
(32:20) The pivotal negotiation with Joe Mailman
(39:22) Fear management and rational risk assessment
(43:40) First major deal loss with Ivy Hill Communications
(49:50) The stoic approach to sunk costs
(55:00) Time management and delegation strategies
(1:02:54) How interviewing is one of Rosenkrantz’s most important activities
(1:04:40) Why businesses requiring less talent often make better investments
(1:11:20) Philanthropy and longevity research funding
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