Stoic Strategies That Built A Self-Made Billionaire | Robert Rosenkranz

Here are the top 10 key takeaways from Robert Rosenkranz's discussion on stoic strategies that built his success as a self-made billionaire.

1. Reading biographies as how-to manuals

Robert Rosenkranz grew up with limited role models at home and turned to biographies for guidance. As a child watching his parents struggle financially, he decided he needed to figure out the world on his own. Biographies became his roadmap for success, teaching him how powerful and influential people navigated life's challenges.

These books served as practical "how-to" manuals that showed him possibilities beyond his immediate circumstances. Through reading about historical figures like Carnegie and Rockefeller, Rosenkranz learned valuable lessons about building wealth, philanthropy, and creating lasting institutions. This habit of seeking wisdom from successful people's lives helped him develop critical thinking skills and self-reliance.

2. Critical thinking as a cornerstone of success

Rosenkranz emphasizes the importance of not absorbing beliefs simply because they're commonly accepted. He developed the habit of subjecting almost everything to critical examination rather than accepting conventional wisdom. This approach was crucial to his success in finance and investing.

This commitment to critical thinking led him to create "Open to Debate," a philanthropic initiative where people can discuss contentious issues civilly. He believes this exercise of questioning and challenging ideas is an essential mental skill. In investing particularly, the ability to spot when consensus thinking is wrong at key turning points provides significant advantages, as market tops occur when everyone is bullish and bottoms when everyone is bearish.

3. Rational decision-making over fear

One of Rosenkranz's pivotal life moments came when starting his own business. He chose to invest 100% of his liquid net worth (about $400,000, equivalent to $4 million today) and take 50% of both profits and losses, a risky arrangement where a 10% loss would wipe him out completely. This decision exemplifies using rationality to overcome fear.

He calculated the mathematical value of his potential gain at approximately $10 million against a potential loss of $167,000. By applying stoic principles of rational control and avoiding catastrophizing, he realized the worst-case scenario wasn't as terrible as emotional thinking might suggest. This clarity allowed him to make a bold move that significantly shaped his career trajectory.

4. Time as the most precious resource

Rosenkranz emphasizes that time, not money, is our most precious resource. He has a chapter in his book titled "You can make more money, you cannot make more time," highlighting the importance of consciously managing time. To maximize this irreplaceable asset, he regularly takes "yellow pad days" where he disconnects completely to evaluate relationships, habits, and opportunities.

He relates a personal story about a neighbor damaging his property and being a jerk about it. Rather than pursuing justice through time-consuming legal means, he chose to use money to solve the problem. This illustrates how wealth can be used to preserve time and peace of mind. Rosenkranz considers these choices essential to living purposefully rather than frittering time away on conflicts.

5. Being a student of everything you do

Rosenkranz approaches new ventures as a serious student rather than assuming expertise. When building his insurance company Delphi, he actively studied successful insurance businesses and corporate cultures, learning from predecessors rather than reinventing the wheel. This learning mindset has been consistent throughout his career.

This approach contrasts with the ego-driven tendency to believe you already know everything after achieving success in one area. He recognizes that truly successful people maintain humility and openness to learning. As Epictetus said, "You can't learn that which you think you already know." Rosenkranz credits this student mentality as essential to building his various successful enterprises.

6. Read the footnotes

In the investing world, Rosenkranz has a crucial rule: always read the footnotes. He explains that while most human pursuits show consistency (good violinists remain good tomorrow), investing uniquely comes with the disclaimer that past performance doesn't predict future results. This creates a challenge for evaluating investment opportunities.

The footnotes in financial statements often reveal what managers don't want investors to know - excessive borrowing to achieve results, self-dealing transactions, or questionable valuation methods for illiquid assets. By looking beyond the headline numbers and marketing pitches, Rosenkranz could identify potential problems or advantages others missed. This meticulous attention to detail proved invaluable throughout his investing career.

7. Wealth as a means, not an end

Rosenkranz views wealth as a tool for achieving a well-lived life rather than an end in itself. He deliberately chose to live beneath his means throughout his career, freeing himself from financial worries even as his wealth grew. This approach allowed his "beneath my means" lifestyle to still be quite luxurious as his success increased.

He sees money as potentially enabling meaningful experiences, aesthetic pleasures, and philanthropic impact. Rosenkranz particularly values the ability to create beautiful living spaces that foster contemplation and conversation. While acknowledging wealth's potential downsides (jealousy, fear of loss), he emphasizes that material abundance can enrich life when approached with the right mindset and purpose.

8. Getting angry without acting angry

A key stoic principle Rosenkranz applies is separating emotional reactions from actions. When confronted by a bank president making demands that felt unfair, Rosenkranz initially felt genuine anger but chose not to display it. After taking time to assess the situation, he decided to capitulate graciously rather than fight.

This decision proved wise when the bank president later offered future assistance, showing unexpected graciousness. The experience taught Rosenkranz that emotional responses are automatic, but actions should be conscious choices. By controlling his response rather than letting anger dictate his behavior, he preserved an important business relationship and achieved a better outcome than fighting would have produced.

9. Process over outcome

What excited Rosenkranz about creating wealth wasn't the money itself but the process of building businesses. He found joy in pursuits that engaged his full range of abilities and encouraged continuous growth and learning. The financial rewards were welcome but secondary to the satisfaction of the journey.

This aligns with Marcus Aurelius's concept of "nature's inadvertence" - valuable outcomes often emerge as byproducts of processes we enjoy for their own sake. Rosenkranz believes finding activities that use your full range of talents is essential to a well-lived life. His success in business came from loving the decision-making, problem-solving, and creative aspects rather than focusing solely on financial outcomes.

10. Ambition in a meritocratic society

Rosenkranz believes his book makes an original contribution by applying stoic principles to a world where ambition can be realized. He acknowledges that ancient stoics lived in societies with limited social mobility, where people largely remained in the positions they were born into. Modern meritocratic societies offer different possibilities.

He feels fortunate to have been born in America, where people of ability can get quality education, build businesses, and achieve positions of influence regardless of birth circumstances. Rosenkranz views his work as extending stoic wisdom to contexts where individual agency and merit can dramatically change one's circumstances. This adaptation makes stoicism particularly relevant to contemporary ambitious individuals seeking both success and wisdom.