At the age of seven, Robert Rosenkrantz decided to take complete control of his destiny. Growing up, he witnessed his parents' financial struggles, with his father out of work for two years while his mother worked as a clerk at a drugstore. The family's financial instability was clear to young Robert, as he often didn't know if they would lose electricity or phone service. However, instead of viewing this as a hurdle, he perceived it as an opportunity for self-sufficiency.
By 14, Rosenkrantz was overseeing his family's investments, and by the time he turned 35, he had accumulated $400,000, which is roughly $4 million today. The turning point in his life came during a negotiation with affluent entrepreneur Joe Mailman. After Mailman expressed worries about conventional investment approaches that resulted in a “heads you win, tails I lose” situation, Rosenkrantz boldly offered to risk his entire liquid net worth in exchange for a 50/50 profit share without any carried interest.
“We lost $100,000 on the first deal. The second deal brought us $100 million,” Rosenkrantz remarked in the interview. “So, it evened out.” Now at 82, he is here to discuss his book, “The Stoic Capitalist,” and the guiding principles of his career. For over 35 years, he has kept a negotiation card from “Getting to Yes” in his wallet, serving as a reminder that negotiation is about collaborative problem-solving rather than competition.
We delve into his unconventional investment strategy: prioritizing companies that require little specialized skills, such as laundromats or self-storage facilities, which he believes are often better investments than those needing high-level management, like restaurants. This approach was key in his first major success, a lawn and garden products venture that simply involved packaging dirt—an uncomplicated business that evolved into a regional monopoly and was eventually sold for $100 million.
Currently, Rosenkrantz is funding scientific research on longevity and organizing debate programs that showcase balanced views on divisive topics. His philanthropic work includes supporting a groundbreaking study that has managed to extend the lifespan of worms from 15 days to more than 250 days—potentially the longest lifespan extension recorded for any organism. When asked about retirement, he quips, “How do you spell that?”
His decision-making advice comes from stoic philosophy: concentrate solely on what you can control— the present and future, and disregard the past. This entails completely ignoring sunk costs when making decisions and using logic to manage emotions. For Rosenkrantz, focusing on opportunities with significant potential impact—essentially counting the zeros—helps him prioritize his time and delegate efficiently. At 82, he continues to apply these principles daily and feels “biologically more like 70 and getting younger.”
Timestamps:
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(0:00) Intro
(2:00) Welcome and introduction to Robert Rosenkrantz
(4:00) The negotiation card from “Getting to Yes” that Rosenkrantz carries
(5:00) Viewing negotiation as problem-solving rather than competition
(7:00) Experience of growing up on the Upper West Side with financially unstable parents
(9:40) Gaining self-reliance at the age of seven
(13:40) Making his first stock investment at 14
(18:20) Managing the family portfolio as a teenager
(22:40) Overview of stoic philosophy principles
(29:00) Transitioning from $400,000 net worth to significant wealth
(32:20) The crucial negotiation with Joe Mailman
(39:22) Managing fear and rationally assessing risks
(43:40) The initial significant loss with Ivy Hill Communications
(49:50) Adopting a stoic view on sunk costs
(55:00) Strategies for time management and delegation
(1:02:54) The importance of interviewing as one of Rosenkrantz’s key activities
(1:04:40) Why businesses needing less specialized talent can be better investments
(1:11:20) Philanthropic efforts and funding for longevity research
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At the age of seven, Robert Rosenkrantz made a choice that would influence his whole life: he would assume total responsibility for his future.