David Rubenstein: We took $5M and turned it into $500B

Episode of My First Million · September 14, 2026 · 47 min

Sam Parr interviews Carlyle Group co-founder David Rubenstein about building a $500 billion private equity firm, missing out on Amazon, historic documents and American history.

Summary

Sam Parr interviewed David Rubenstein, co-founder of The Carlyle Group, beginning with Rubenstein's time as a 27-year-old deputy domestic policy adviser in the Jimmy Carter White House and his difficulty finding work after Carter lost in 1980. Rubenstein recounted founding Carlyle at 37 with $5 million from four investors in 1987, doing deals one at a time before raising funds, and his role as fundraiser, recruiter and public face of the firm while partners such as Bill Conway handled investing. He said Carlyle's innovations included running multiple fund types and globalizing, and that recruiting figures such as Frank Carlucci, James Baker, George H. W. Bush and John Major opened doors.

Rubenstein described passing on early chances with Facebook, which he viewed as a dating company, and Amazon, where Jeff Bezos offered roughly 20% of the company for rights to a bibliography; Carlyle later took some stock but sold at the IPO, a stake he estimated would be worth $14 billion. He argued that successful founders have staggering self-confidence but also need luck, citing IBM's decision not to own Microsoft's operating system, and said that as an entrepreneur he still worries every day, including about the Baltimore Orioles' playoff chances.

The conversation turned to his personal life: frequent travel while raising children, his commitment under the Giving Pledge to give away most of his wealth, and frugal habits rooted in a blue-collar Baltimore upbringing. Rubenstein discussed former Carlyle executive Glenn Youngkin's rise to governor of Virginia and the role of luck in success.

In the final part, Rubenstein discussed buying the Magna Carta and copies of founding documents, rising prices tied to the semiquincentennial, Thomas Jefferson's doubts about the republic's survival, his concern about the $40 trillion federal debt, reading as an "anti-Alzheimer's device," recommended books, and his views on Lincoln, Washington, and Secret Service mistakes in the Lincoln and Kennedy assassinations.

Chapters

  1. 0:00

    Preview and Carter White House years

    Rubenstein recalls joining the Carter White House at 27 as deputy domestic policy adviser and tracking campaign promises.

  2. 3:07

    Out of power and into law

    After Carter's defeat Rubenstein struggled to find work, practiced law briefly and decided to start an investment firm.

  3. 5:17

    Founding Carlyle at 37

    Rubenstein explains why he started Carlyle at 37, his early hires, raising $5 million and the deal-by-deal model.

  4. 8:25

    Fundraising, multiple funds and a scrappy start

    Rubenstein describes his fundraising role, the multi-fund global strategy, the small first office and the Washington pitch.

  5. 13:25

    Missing Facebook and Amazon

    Rubenstein recounts passing on Zuckerberg's company and selling Amazon stock at the IPO, and discusses founder self-confidence.

  6. 16:25

    Recruiting big shots and surviving near-failure

    Rubenstein describes recruiting Carlucci, Baker, Bush and Major, a cash crisis in a bankruptcy deal, and sales of stakes to CalPERS and Mubadala.

  7. 20:00

    Constant worry, family and philanthropy

    Rubenstein discusses entrepreneurial anxiety, his partners, the Orioles, parenting while traveling and the Giving Pledge.

  8. 23:52

    Fulfillment and frugal habits

    Rubenstein reflects on admiring James Baker, his blue-collar roots, his $15 haircut and long-worn suits.

  9. 28:12

    Power, luck and Glenn Youngkin

    Rubenstein discusses watching Glenn Youngkin rise to governor and argues success is unpredictable and depends on luck.

  10. 30:31

    Collecting historic documents

    Rubenstein explains buying the Magna Carta and founding-era documents and why prices have risen.

  11. 35:00

    Federal debt and the reading habit

    Rubenstein voices concern about federal debt and describes reading and interviewing authors as brain exercise, recommending books.

  12. 41:06

    Presidents and assassinations

    Rubenstein and Parr discuss Lincoln, Washington, the Lincoln and Kennedy assassinations and security then and now.

Key points

What was said, by whom, with the exact words. Timestamps jump to the moment.

  • David Rubenstein

    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”

    Listen from 5:32 · Entrepreneurship

  • David Rubenstein

    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”

    Listen from 6:33 · Entrepreneurship

  • David Rubenstein

    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”

    Listen from 9:15 · Private equity

  • David Rubenstein

    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”

    Listen from 12:47 · The Carlyle Group

  • David Rubenstein

    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”

    Listen from 13:55 · Facebook

  • David Rubenstein

    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”

    Listen from 15:31 · Amazon

  • David Rubenstein

    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”

    Listen from 15:58 · Entrepreneurship

  • Linked moment · 18:01Skip to 18:01 using a listen link in the info box.

    David Rubenstein

    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”

    Listen from 18:01 · The Carlyle Group

  • 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”

    Listen from 20:12 · Entrepreneurship

  • David Rubenstein

    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”

    Listen from 23:13 · Giving Pledge

  • David Rubenstein

    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”

    Listen from 30:03 · Microsoft

  • David Rubenstein

    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”

    Listen from 31:12 · Magna Carta

  • David Rubenstein

    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”

    Listen from 32:01 · United States Semiquincentennial

  • David Rubenstein

    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”

    Listen from 33:33 · United States Declaration of Independence

  • David Rubenstein

    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”

    Listen from 35:38 · National debt of the United States

  • David Rubenstein

    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”

    Listen from 37:07

  • David Rubenstein

    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”

    Listen from 42:15 · Assassination of Abraham Lincoln

  • Sam Parr

    Parr says reading about presidential assassinations showed him that the Secret Service was underdeveloped until around the 1970s.

    “the Secret Service really wasn't a thing until like the 70s. Like they talk about JFK's Secret Service. It was pretty rinky-dink”

    Listen from 42:50 · Assassination of John F. Kennedy

  • David Rubenstein

    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”

    Listen from 43:30 · Assassination of John F. Kennedy

People

In the conversation

  • Sam ParrEntrepreneur, founder of The Hustle and Hampton, co-host of My First Million
  • David RubensteinAmerican businessman, co-founder of private equity firm The Carlyle Group, philanthropist and principal owner of the Baltimore Orioles

Discussed

Topics

More from My First Million

From the publisher

Sam's database on how long it takes to become a millionaire: https://clickhubspot.com/pnlv Episode 861: Sam Parr ( https://x.com/theSamParr ) sits down with David Rubenstein ( https://x.com/DM_Rubenstein ) to talk about turning Carlyle into $500B, his $14B miss, and the greatest business lessons in history. — Show Notes: (0:00) Turning $5M into $500B (5:13) Scrappy private equity (11:58) Don’t fool yourself (14:14) Turning down 20% of Amazon (16:23) Recruiting big shots (20:40) Finding the right partner (22:02) Trade-offs (27:39) Witnessing ascents to power (31:40) The Greatest Sentence Ever Written (33:37) History that repeats itself (35:49) Recommended Reading — Links: • Carlyl - https://www.carlyle.com/ • David’s books - https://www.davidrubenstein.com/books/ — Check Out Sam's Stuff: • Hampton (joinhampton.com): My community for founders. Average member does $25m/year. Many of the guests are members. Get after it...apply: http://joinhampton.com/mfm — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Shaan uses Mercury across all of his companies. you can too: http://mercury.com/ Mercury is a fintech company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., Members FDIC • I run all my newsletters on Beehiiv and you should too + we're giving away $10k to our favorite newsletter, check it out: beehiiv.com/mfm-challenge My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano /

Summary, chapters and key points were generated from the episode transcript on October 10, 2026. Quotes are checked word for word against the transcript.

Categories: Entrepreneurship·History·Investing