David Rubenstein

Rubenstein says entrepreneurs constantly expect something bad to happen and he still worries every day.

“No, because if you're an entrepreneur, you always think something bad is going to happen”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 20:12

Rubenstein argues that company builders share extraordinary self-confidence.

“if you go back and look at anybody that built a company, they have self-confidence that is staggering”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 15:58

Rubenstein asserts that nearly all U.S. startups fail within five years.

“remember 99.9% of the companies that started the United States are not in business five years later”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 6:33

Rubenstein says he started Carlyle at 37 because he had read that people who have not started a company by that age probably never will.

“If you haven't done it by 37, I read, you probably will never start a company”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 5:32

Rubenstein says recruiting prominent figures like James Baker helped open doors, especially in Middle East fundraising.

“if your last name is Rubenstein and you go to the Middle East to raise money, it might not be as compelling as if you go with Jim Baker”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 18:01

Rubenstein says Carlyle pitched its Washington base as an advantage in understanding government-affected companies.

“We understand that companies heavily affected by the federal government better than the guys in New York”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 12:47

Rubenstein argues the Secret Service erred by publicizing the route and removing the bubble top, and that Kennedy would otherwise have lived.

“Secret Service should not have listened to a political advisor. They should have kept the bubble top on. Had they done that, Kennedy would have lived”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 43:30

Rubenstein argues that had Ulysses S. Grant attended Ford's Theatre, his military aides would likely have prevented Booth from reaching Lincoln.

“Probably John Wilkes Booth would not have gotten into that presidential box, because there would've been a lot of military A's”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 42:15

Rubenstein describes reading heavily and interviewing authors as his way to keep his brain active and ward off Alzheimer's.

“it's a good way to keep your brain active when you reach my age, so I do it as my anti-Alzheimer's device”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 37:07

Rubenstein argues the federal debt cannot realistically be repaid and will effectively be paid off in devalued dollars.

“we have $40 trillion of federal debt. Our ability to pay this off is virtually non-existent”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 35:38

Rubenstein says Thomas Jefferson did not expect the new country to last more than about 20 years.

“Jefferson didn't think it would survive for more than 20 years”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 33:33

Rubenstein says interest in the Declaration of Independence around the semiquincentennial has driven up prices of historic copies.

“the Declaration of Independence, because of the semi-quincentennial, has become a document of greater interest to people, so the prices have gone up dramatically”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 32:01

Rubenstein says he buys historic documents and restores monuments so people will learn more about American history.

“And the reason is I want people to know more about American history”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 31:12

Rubenstein argues Microsoft benefited from luck when IBM chose not to own the PC operating system it hired Microsoft to provide.

“When IBM was looking for a software or operating system for its PC, they hired Microsoft to provide it”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 30:03

Rubenstein states he is committed to giving away most of his wealth as an early Giving Pledge signer.

“But I'm committed to giving away most of my money. was an early original signer of the Giving Pledge”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 23:13

Rubenstein says Carlyle sold its Amazon stock at the IPO, a stake he estimates would now be worth $14 billion.

“We got some stock, but then we sold it at the IPO. That was stupid. That stock's probably worth $14 billion now”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 15:31

Rubenstein recounts declining to invest in Zuckerberg's early company because he saw it as a dating site.

“I said, I'm not going to invest in that. It's a dating company”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 13:55

Rubenstein says Carlyle's novel approach was running multiple fund types and then globalizing them.

“I came up with the idea of having a buyout fund, a growth fund, a real estate fund, a debt fund, and I had multiple funds”

My First Million: David Rubenstein: We took $5M and turned it into $500B (Sep 14, 2026) · Listen from 9:15