David Rubenstein on investing, time, and designing a life worth living

Executive overview

Most people invest emotionally — buying high out of fear of missing out, selling low out of panic. The reverse is almost always the better move. Beyond market mechanics, the deeper question is what money is actually for: Rubenstein argues time is the only truly nonrenewable resource, and the wealthiest people are often the worst at protecting it.

The real investment is how you spend your time, not just your money.

The biggest investing mistakes most people make

• Buying when markets rise (FOMO) and selling when they fall — the opposite of what works
• Believing you can beat the market by reading about it; most people cannot
• For the average investor, a low-cost index fund matches or beats active stock-picking
• Warren Buffett's edge is less brilliance than time: averaging ~20% annually for 60 years, never selling, never paying capital gains tax
• Holding avoids transaction costs and taxes; selling is usually the mistake
• Time horizon and cash needs determine when selling makes sense — not short-term psychology

On missing Facebook, Amazon, and learning from mistakes

• Passed on investing in Facebook when Zuckerberg was at Harvard — dismissed it as a dating service
• Sold Amazon early, convinced a bookseller couldn't become a major growth business
• Peter Thiel saw the opposite; Rubenstein attributes the difference partly to Thiel being smarter
• Most early-stage ideas that changed the world seemed obviously dumb at the time (Twitter, Square)
• Today, every idea gets taken seriously by VCs — the opposite problem from 20 years ago

Why great investors love what they do

• Great investors don't wish they were playing golf; the work itself is the reward
• Nobody wins a Nobel Prize hating their work — passion is a prerequisite for sustained excellence
• Rubenstein writes his own books and hosts his podcast because he genuinely enjoys it, not for the money
• Wealthy people often want to do what writers and creators do; protect what you already love doing

Time as the scarcest resource

• Money compounds over time; so does the cost of wasting it
• A private plane isn't a luxury purchase — it's buying back 40+ travel days per year
• Choosing a 10% rental property return over a 7% index fund often ignores the time cost of managing property
• The richest people are frequently the worst at valuing their own time
• "It takes exactly twice whatever you have" — financial security is a moving target, not a destination

On philanthropy, legacy, and what money is actually for

• Most very wealthy people eventually give the bulk away to non-family causes
• Patriotic philanthropy — restoring the Washington Monument, Magna Carta loans to museums — gives a sense of doing something useful for the country
• Bill Gates tries to apply ROI metrics to philanthropy; Rubenstein finds it nearly impossible in practice
• Giving time is as valuable as giving money; time cannot be replaced
• Rubenstein chairs five major boards (Kennedy Center, University of Chicago, Council on Foreign Relations, Library of Congress, National Gallery of Art) — chairing takes serious time

The FIRE movement and the retirement question

• FIRE (Financial Independence, Retire Early) optimises for spending as little as possible to retire decades early
• Rubenstein's counter: retirement means doing what, exactly? Watching the Criterion Collection is not a life
• Professional athletes retire in their mid-30s — most don't accomplish much afterward
• The people who go back into coaching are addicted to the game; the stars rarely do
• Deferring living — saving in Sacramento to retire in Hawaii — often means the best years are spent in the wrong place

On raising children with money

• Avoiding spoiling children is harder the wealthier you are; some wealthy kids accomplish nothing, become addicts
• All three of Rubenstein's children went into private equity independently — he doesn't fully know why
• Nobody on their deathbed says they wished they'd spent less time with their kids
• Spending time with children probably matters more than any financial inheritance
• Find something you love — you can't do great things hating what you do

Carter, Lincoln, and political capital

• Carter saw himself as an anti-politician: if you told him something was politically smart, he'd often do the opposite
• He never believed he'd lose to Reagan — didn't take Reagan seriously until it was too late
• The hostage crisis was decisive; Iran wanted Carter humiliated, not to give him the win
• Being challenged within your own party (Kennedy primary) almost always dooms an incumbent
• Lincoln's 13th Amendment push was pure political will — just causes don't pass themselves; votes have to be secured

On historical documents and long-term preservation

• Rubenstein owns souvenir copies of the Emancipation Proclamation (only ~10 of the 47 signed remain)
• Preserving originals matters not because we don't know the words, but because seeing the physical object makes people engage more deeply with history
• Founders signing the Declaration believed they were committing treason — signatures were withheld for months
• Physical documents make the human origin of history undeniable; they weren't handed down from above