My Interview with Burton Malkiel (That You Will Never Hear)

4 May 2026 · 42 min · 17 chapters

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

A narrative history of index investing, centered on Burton Malkiel and Jack Bogle, arguing that after fees it’s extremely hard for active managers to beat the market, and that the real challenge is holding through fear and avoiding mistimed “right early” decisions.

Guest backgrounds

Burton Malkiel is author of A Random Walk Down Wall Street (1973; 13+ editions), taught at Princeton, was dean at Yale School of Management, and served on Vanguard’s board. Jack Bogle (discussed) founded Vanguard and pushed low-cost index funds.

Key claims

Active managers don’t consistently outperform after fees; diversification reduces risk via correlation; efficient markets are “always wrong” in direction but hard to exploit after costs; concentration in mega-cap tech is not new and index investors shouldn’t time it.

Notable examples

Markowitz (Portfolio Selection, 1952); Samuelson’s “alchemy” critique (1974); Fama’s efficient market hypothesis (1970); Wells Fargo’s early index fund (1971) and Vanguard’s 1976 launch (0.2% fee); Black Monday (1987) recovery; Greenspan’s “irrational exuberance” (1996) timing cost; dot-com and 2008 housing crash; 401(k) fee transparency. Retirement advice: keep equities longer; include TIPS and municipal bonds; “stay engaged.”

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

The Disappearing Interview

1:10 to 2:50

Tyler reflects on losing his interview with Burton Malkiel and its significance.

“Burton Malkiel, the author of A Random Walk Down Wall Street.”

The Story of Index Funds

3:01 to 4:44

Learn about the history and importance of index funds in personal finance.

“and I am not letting that disappear just because I am, apparently, a person who cannot operate basic software.”

The Rise of Jack Bogle's Idea

4:47 to 5:32

Understand Jack Bogle's revolutionary concept of index investing.

“That the average investor would be better off buying the entire market at the lowest possible cost and then doing absolutely nothing.”

The Academics Behind Index Investing

11:08 to 14:01

Dive into the contributions of key economists to the index fund theory.

“The first person you need to know is a man named Harry Markowitz.”

Understanding Market Efficiency

14:01 to 15:37

Learn the foundations of market efficiency and its implications for investors.

“which means you cannot consistently beat the market by analyzing information, because the information is already in the price.”

The Birth of the First Index Fund

15:38 to 20:03

Discover the history and challenges faced by the first institutional index fund.

“The First Index Fund and How It Nearly Died Here's where the story gets interesting, and a little painful, and honestly, pretty inspiring.”

The Wilderness Years of Index Funds

23:32 to 27:02

Explore the struggle of index funds amidst a booming active management industry.

“The Wilderness Years Here's something I find almost unbearably interesting about this story.”

The Turning Point for Index Investing

27:02 to 28:00

Learn about pivotal changes that led to a rise in index fund popularity.

“A few things, and they built on each other slowly.”

The Evolution of Investment Strategies

28:00 to 29:50

Explore how mutual funds and 401ks changed investor behavior.

“Some guys were on a streak, and then the streak would end.”

Lessons from Market Crashes

29:50 to 31:58

Learn from historical crashes and the importance of holding investments.

“He kept showing up to conferences where he was not popular and saying the same thing he had always said.”
Show all 17 chapters

The Dot-Com Bubble and Its Aftermath

31:58 to 34:08

Understand the implications of the dot-com bubble and market timing.

“Then came the 1990s, the dot-com boom, the internet era, and here's where the efficient market hypothesis gets genuinely complicated.”

The 2008 Financial Crisis: A Recap

34:08 to 36:08

Examine the 2008 financial crisis and its impact on investing behavior.

“After the dot-com crash, after the rubble cleared, after the postmortems were written, the case for index investing had never been stronger.”

Burton Malkiel's Enduring Influence

36:08 to 38:10

Discover Burton Malkiel's contributions to investing and education.

“The investors who sold at the bottom or near it locked in losses and then watched from the sidelines as the market doubled, then tripled, then quadrupled.”

Current Challenges in Index Investing

38:10 to 40:10

Discuss the current state of index investing and market concentration.

“They hadn't yet been trained to ask sophisticated questions that often obscure simple truths.”

Malkiel's Insights on Retirement Planning

40:10 to 42:01

Gain valuable insights on retirement investments from Burton Malkiel.

“Railroads, steel companies, computer stocks in the 80s, internet stocks in the 90s, AI now.”

Understanding Retirement Uncertainty

42:01 to 43:31

Explore the challenges of self-directed retirement and the importance of staying engaged.

“And for a generation that watched their parents work until 65 and then have a pension check arrive every month, the shift to self-directed retirement can be genuinely disorienting.”

Burton Malkiel's Life Advice

43:31 to 45:17

Learn from Burton Malkiel's insights on asset allocation and the value of lifelong engagement.

“His best life advice, especially in retirement, always and forever, stay engaged.”
Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:00Tyler Gardner:The cost of being right early in markets is often indistinguishable from the cost of being wrong. This is the trap that catches even sophisticated investors.

0:14Burton Malkiel:Hello friends, this is Tyler Gardner welcoming you to another episode of your Money Guide on the Side,

0:20Tyler Gardner:where it is my job to simplify what seems complex, add nuance to what seems simple, and learn from and alongside some of the brightest minds in money, finance, and investing. So let's get started and get you one step closer to where you need to be.

0:38Burton Malkiel:Quick note before we get into it. May's pre-order incentive for my book, Real Wealth, is now live. When you pre-order this month, I'm sending you two chapters that didn't make the final cut. Chapters I genuinely love and wish I could have kept, delivered digitally in early June. Pre-ordering also locks you in for every monthly incentive between now and the December 1st release. Go to tylergardner.com slash book, click the button that says claim my bonuses, upload your receipt, takes two minutes, and you're in.

1:07Tyler Gardner:Now, on with the show. I want to tell you about the worst thing that happened to me last week. I know, great transition. Last Thursday, I had the opportunity to sit down on Zoom with one of the most influential and important figures in the history of personal finance, a man who in 1973 wrote a book that changed the way ordinary people think about money. A man who has been right, almost maddeningly right, through Black Monday, the dot-com crash, 2008, COVID, and every single moment in between when someone in an expensive suit on television was absolutely certain the old rules no longer applied.

1:53Tyler Gardner:I had an hour with Dr. Burton Malkiel, the author of A Random Walk Down Wall Street. We talked about fear and behavior and what retirement actually means when you're 93 years old and still intellectually curious and still showing up. We talked about Jack Bogle. We talked about whether financial education even works. We talked about irrational exuberance and why acting on Alan Greenspan's 1996 speech would have cost you years of some of the best returns in stock market history. It was one of the best conversations I have ever had about money. And then, before hitting stop recording on Zoom, I ended the meeting and exited Zoom.

2:41Tyler Gardner:Apparently, that means the recording is gone forever. Don't worry, I've already contacted Zoom support. It is gone. So after sulking in a corner for seven days, I decided to pick my head up, reconstruct what I could from memory, and give you the best of the conversation. Because Burton Malkiel gave me an hour of his time and I am not letting that disappear just because I am, apparently, a person who cannot operate basic software. But here's what I realized while I was sitting with the loss of that recording. The reason that conversation mattered so much to me, the reason I was nervous going into it in a way I almost never am before an interview, isn't just that Burton Malkiel is brilliant, or that a random walk down Wall Street is now in its 13th edition, or even that we share a publisher, which still feels slightly unreal to me as a former high school English teacher from Vermont, it's that Malkiel is one of the central characters in one of the most important and underappreciated stories in the history of personal finance.

3:48Tyler Gardner:A story about a dangerous idea, a story about the people who did the math first, the people who tried to build the thing and nearly failed, and the industry that spent decades trying to bury all of it. So that's what today's episode is. Deviating from my traditional form, I'm going to tell you a story, the full story, the economists, the academics, the traders, the fund that got called un-American. And as we go, I'm going to do my best to weave in the pieces I remember from my conversation with Malkiel to add firsthand credibility and depth of experience. The things he said about fear and behavior and concentration and what it actually means to stay the course, they're going to land differently, I think, when you hear them inside the history they helped shape.

4:43Tyler Gardner:The story starts with a man named Jack Bogle and an idea that Wall Street spent decades trying to kill. The idea? That the average investor would be better off buying the entire market at the lowest possible cost and then doing absolutely nothing. Buy everything, pay almost nothing, do nothing. The industry that tried to kill that idea now manages over$30 trillion in index funds. And as always, a familiar ask. If you found this podcast helpful in any way, please consider leaving a review on Apple or Spotify as it helps the show grow, and it helps me know that I'm not just telling stories about index funds to my sleeping bloodhounds.

5:32Tyler Gardner:Chapter 1. The World Before Index Funds. To understand why index funds were so controversial, you have to understand what the world looked like before them. In the 1950s and 1960s, the American economy is booming. The stock market is climbing. And Wall Street, the actual physical geographic Wall Street, is doing what Wall Street has always done, positioning itself as the essential middleman between you and your money. Here's how investing works in this world. You have money you want to invest. You can't really do it yourself. The information gap between you and a professional is enormous. The transaction costs are steep, and frankly, nobody's told you that you could.

6:24Tyler Gardner:So you hire a mutual fund manager, a professional, someone who went to the right schools, shook the right hands, pretended to read the right books, and who has access to the trading floors and the earnings calls and the back-channel relationships with corporate executives. You pay this person handsomely for their expertise. They charge you an annual fee. Often 1-2 % of everything you have with them every single year, regardless of performance. Beyond that, they charge you massive transaction fees for every single trade. And in exchange, there is an unwritten promise that they will do better than the market.

7:06Tyler Gardner:This is the entire value proposition of active management. I am smart enough and connected enough to identify the stocks that will outperform. you cannot do this yourself, pay me. And people did for decades because there was no alternative and because the pitch was emotionally compelling. You want someone smart on your side. You want someone fighting for you. You want to believe that expertise translates into performance. This is where I want you all doing your best Matthew McConaughey chest beating impression,

7:40Burton Malkiel:where he tells an aspiring Jordan Belfort that it's all a scam, but it's a scam that continues to make the professionals on Wall Street filthy rich.

7:49Tyler Gardner:The problem, and it is a problem that a handful of very smart, very contrarian people started noticing in the 1950s, is that it simply wasn't true. The experts, on average, were not beating the market. Not before fees, and certainly not after them.

8:10Burton Malkiel:This week's episode is brought to you by Fabric. Here's why term life insurance lives at step four in my financial order of operations. Ahead of funding your Roth, ahead of even fully funding your emergency fund. An emergency fund covers a job loss, a hospital bill, a transmission. You should have one. But there is one emergency no emergency fund can absorb. And that is the loss of the income earner. If you make$100 ,000 a year and have 20 working years left, you're walking around with a$2 million asset on your personal balance sheet. Your emergency fund cannot replace that. Your Roth cannot replace that.

8:52Burton Malkiel:Term life can. That is the entire point. Fabric by Gerber Life skips the whole laminated brochure version. You apply online in about 10 minutes, no medical exam required for most applicants, and a million dollars in 20-year coverage can run less than a dollar a day if you're young and healthy, which is exactly why now is dramatically cheaper than later. 10 minutes from now, you can have this handled, and then, and only then, move on to funding your Roth IRA. Go to meetfabric.com slash Tyler. That's M-E-E-T-F-A-B-R-I-C dot com slash Tyler. Policies issued by Western Southern Life Assurance Company, not available in certain states, prices subject to underwriting and health questions.

9:40Burton Malkiel:This episode is brought to you by Gelt. Tax day has come and gone. But quick question, How did your CPA treat you this tax season? Did they reach out proactively, walk you through your options, and make you feel like a priority? Or did you hear from them in mid-March, feel rushed, and wonder afterward if you left money on the table? That second experience is not normal. You just haven't experienced what a great CPA can do yet. A great CPA is a year-round partner, not a once-a-year fire drill. And Q2 is the best time to make a switch. Your new CPA has bandwidth, your numbers are fresh, and there's a full year ahead to make moves that matter.

10:23Burton Malkiel:Gelt is offering two things for new clients who sign up before June 30th. First, if you filed an extension, a focused 30-minute session with a CPA to find everything that can still impact your 2025 taxes before the October deadline. Second, for any new client onboarding in Q2, Gelt will go back through recent returns and find deductions you may have missed, and in many cases, recover them. Both are paid add-ons that often cost you nothing net by the time they're done. If you're a business owner or a high net worth individual, and your CPA made you feel like an afterthought this season, go to joingelt.com slash Tyler.

11:02Burton Malkiel:That's J-O-I-N-G-E-L-T dot com slash Tyler.

11:08Tyler Gardner:Chapter 2. The Academics Who Finally Did the Math. The first person you need to know is a man named Harry Markowitz. 1952. Markowitz is a 25-year-old graduate student at the University of Chicago. He publishes a paper called Portfolio Selection in the Journal of Finance. It is 12 pages long. it will go on to win him a nobel prize the core insight of the paper is this the return of an individual stock is not the only thing that matters what matters is how that stock behaves relative to everything else in your portfolio diversification spreading your money across many assets reduces risk without necessarily reducing return because different assets go up and down at different times.

12:01Tyler Gardner:This is known as correlation, and the volatility of your portfolio is not the sum of the volatility of its parts. This sounds obvious now, but in 1952, it was revolutionary, and it had an uncomfortable implication. If diversification is good, and more diversification is better than the logical endpoint is owning everything. But Markowitz was a theorist. He built the model. He didn't build the fund. The next person you need to know is Paul Samuelson. Samuelson was at MIT. He was arguably the most influential American economist of the 20th century, the man who wrote the textbook that trained an entire generation of economists.

12:51Tyler Gardner:In 1974, he published a paper called Challenge to Judgment, and in it, he said something that landed in the investment management industry like a grenade. He said, show me the evidence that professional active managers beat the market consistently over time, because I've been looking for it and I cannot find it. He wasn't polite about it. He compared active management to alchemy. He said the burden of proof should fall on the people claiming they can beat the market, not on the skeptics. And he ended the paper with something remarkable, a direct challenge to anyone out there with the institutional courage to actually build an index fund for ordinary investors.

13:40Tyler Gardner:Nobody took him up on it at first. The third person you need to know is Eugene Fama. Fama, also at Chicago, published his efficient market hypothesis in 1970. His core claim, asset prices reflect all available information at all times, which means you cannot consistently beat the market by analyzing information, because the information is already in the price. By the time you read the earnings report, 10 ,000 other people have already read it and traded on it. This is the academic foundation underneath index investing. If prices are already right, or right enough most of the time, then the whole enterprise of stock picking is roughly equivalent to a very expensive coin flip.

14:33Tyler Gardner:Now, I want to be honest with you here. The efficient market hypothesis is not universally accepted. There are serious economists who push back on the strong a form of it. This is one of the first gems I took away from my conversation with Burton Malkiel. After asking him how he had first developed his conviction in efficient market theory, in other words that the market is always right, he paused me. He said he wanted to correct a part of my research. He clarified that he believes the market is actually always wrong. The problem, problem, you just don't know in which direction it's going to be right, which is not quite the same thing as saying prices are always right.

15:19Tyler Gardner:But here's what even the critics agree on. Consistently exploiting market inefficiencies after fees over long periods of time is extraordinarily difficult. Difficult enough that most professional managers fail to do it, and that's the point. Chapter 3. The First Index Fund and How It Nearly Died Here's where the story gets interesting, and a little painful, and honestly, pretty inspiring. It's 1971. A group of researchers at Wells Fargo, not academics, but practitioners, built the First Institutional Index Fund. It tracked an equal-weighted index of stocks listed on the New York Stock Exchange.

16:03Tyler Gardner:It was designed for large pension funds. It was, in the language of the time, theoretical and mechanical. It wasn't available to regular people, but it existed. The concept was being tested. Then came 1974, the year everything nearly fell apart. 1974 was one of the worst years for the stock market in American history. The oil embargo, stagflation, the S &P 500 fell nearly 48 % from its 1973 peak. If you had any money in the market, you watched it get cut almost in half. The conventional wisdom, which is rarely wise and almost never conventional in any meaningful sense, held that this was exactly why you needed a professional.

16:52Tyler Gardner:Because a professional would have seen this coming. A professional would have gotten out. But they didn't get out. Almost none of them did. But that's not what people were saying in 1974. Enter one of our main characters, John Clifton Bogle, known to his friends lovingly as Jack. Bogle was running a mutual fund company called Wellington Management. He had just been fired. Fired from the company he had largely built. After a disastrous merger he had engineered with a go-go growth fund in the late 1960s. The timing was terrible. The fund blew up. The partners forced him out. But as part of the separation agreement, he retained control over the fund's board of directors.

17:40Tyler Gardner:And rather than go quietly, he used that control to start something new. He called it Vanguard, named after a British naval flagship, Admiral Nelson's ship at the Battle of the Nile. And the first thing he wanted to build was an index fund for ordinary investors. Vanguard launched the first index investment trust in August of 1976. It tracked the S &P 500. The expense ratio, the annual fee to be invested in that fund, was 0.2%, a fraction of what active managers were or are charging. The plan was to raise$150 million in the initial public offering. They raised$11.3 million. The underwriters were furious.

18:30Tyler Gardner:Some of them called it a sure failure. The financial press called it Bogle's folly. Fidelity, Vanguard's primary competitor, took out ads with the tagline, who wants to be average? A senior Fidelity executive reportedly called the idea un-American. The argument was that indexing meant settling. It meant giving up. It meant accepting mediocrity when American ingenuity could do better. I want you to sit with that framing for a second, because honestly, it's evil genius. Owning every company in the American economy, every single one, was being sold as settling, as giving up, as un-American. And the people calling it un-American were the very people charging you 1 % to 2 % a year to pick stocks for you, and on average, losing to the market they were supposed to beat.

19:29Tyler Gardner:Sound familiar? It should, because this nonsense narrative continues to this day. The fund struggled for years. Investors simply weren't interested in being average. The concept was too abstract, too counterintuitive, too boring. You're telling me I should just own everything and not try to beat anything? Where's the excitement in that? By 1980, the first index investment trust had less than$100 million in assets. This, for context, is not a lot of money for a mutual fund. It barely existed.

20:06Burton Malkiel:This episode is brought to you by Element. My sister is a marathoner who treats Element like a food group. When I told her I was partnering with them, she called for 17 minutes. The first 10 were enthusiasm. The last 7 were logistics about how many boxes I could get her and how quickly. I've also mysteriously been reconnecting with old cycling friends. Years of radio silence, and now my phone is buzzing. Genuinely touching, but each call ends the same way. So, what's this Element situation exactly? Followed by an unprompted shipping address. Anyway, some actual news. For salt monsters like me, my sister, and my cycling crew, it's outstanding news.

20:48Burton Malkiel:Element just launched Pink Lemonade, a limited-time flavor available exclusively to Element insiders. Sweet, slightly tart, naturally pink. I love it. I'm also still obsessed with mango chili, which I will be drinking until they pry it from my cold, adequately hydrated hands. To become an insider, order the Insider Bundle, four boxes for the price of three, the best value they offer, and you get early access to flavors like pink lemonade, plus surprise gifts along the way. So instead of calling me and giving me your mailing address, go to drinkelement.com slash Tyler, become an insider, get the pink lemonade, and if my sister calls, just know she's been working on her pitch for weeks.

21:32Burton Malkiel:That's drinklmnt.com slash Tyler. This episode is brought to you by Facet. I want to read you two messages I get every single week. First one, Tyler, I'm retiring in two years with about a million dollars saved. What should I be investing in right now? Second one, should I take social security at 62 or wait until 70? I genuinely don't know what to do. And I want to help. That's why I do what I do. But those questions will never have a universal answer. They only have your answer. And your answer depends on your health, your other income sources, your tax situation, your spouse, your timeline, and about 40 other variables I cannot responsibly address to a general audience of over 4 million people.

22:20Burton Malkiel:Those questions deserve a real answer from a real professional, not a guy on the internet speaking generally. A CFP who sits down with your actual numbers and builds a plan that is specifically yours. That is exactly what FACET does. CFP professionals, flat annual membership fees, not a percentage of your assets, not a commission, none of the fee structures I've spent years telling you to avoid. Your social security question, your million dollars, your plan. If retirement is close enough that the stakes feel real, this is the conversation worth having today. Facet helps you bring your whole financial life together.

22:57Burton Malkiel:Social Security, Medicare, long-term care, Roth conversions, RMDs, all of it. So head to facet.com slash Tyler and see how their team can help you answer the questions you're already asking. That's facet.com slash Tyler. Facet is an SEC-registered investment advisor. This is not advice. All opinions are my own and not a guarantee of a similar outcome. I'm not a member of Facet. I have an incentive to endorse FACET as I have an ongoing fee-based contract for cash compensation, as well as a percentage of equity in FACET based on this endorsement.

23:31Tyler Gardner:Chapter 4. The Wilderness Years Here's something I find almost unbearably interesting about this story. Between 1976 and the mid-1980s, the evidence kept coming in. Study after study, paper after paper, decade after decade of returns data, all pointing in the same direction. Active managers, in aggregate, do not beat the market. After fees, the average active fund underperforms the index it's trying to beat by roughly the amount of its fees, which makes perfect sense. The market is, by definition, what you get if you add up all of the investors. If the average investor gets market returns, and active managers are investors, then active managers as a group get market returns minus their fees, which means active managers as a group underperform by exactly the amount they charge.

24:30Tyler Gardner:This is not a controversial statement, and to the academics, it never has been. It is basic arithmetic. But arithmetic, it turns out, is not always persuasive, especially when the people it's working against are the ones with the money, the marketing budgets, and the television time. The mutual fund industry in the 1980s was an extraordinary machine for generating fees. The actively managed fund business was printing money for the managers. The sales commissions alone, called loads, could run to 8 % of your initial investment.

25:10Burton Malkiel:8 % off the top before a single stock was purchased, before a single return was generated before you had even technically started investing. And the pitch kept working.

25:23Tyler Gardner:Because when the market was going up, as it did for most of the 1980s, every fund was making money. And when every fund is making money, it's very hard to convince someone that the fees they're paying are eating those returns. Because the gains feel real. The costs feel abstract. In fact, Burton Malkiel was writing and teaching throughout all of this. A random walk down Wall Street went through edition after edition. Each one updated the data. Each one said the same thing. The evidence is here. The math is clear. Buy an index fund. Make more money. Think about that. The moments when index investing is easiest to accept intellectually are the exact moments when it's also hardest to argue for emotionally.

26:11Because when everything's going up, nobody wants to hear,

Read the full transcript

26:15Tyler Gardner:you could have done this basically for free. They want to believe the guy they're paying was responsible. And based on my conversations with so many of you, this too continues to this day. And the moments when the case for indexing is mathematically strongest, After a crash, when active managers have failed to get out just like everybody else, are the exact moments when people are most desperate for a hero, most willing to believe that the next active manager will be different, will be better, will see it coming. And the financial services industry understood this psychology perfectly, and they used it to take your money and put it in their pockets.

27:01Tyler Gardner:Chapter 5. The Turning Point. So what changed? A few things, and they built on each other slowly. First, the data kept accumulating. By the late 1980s, there were now about 20 years of returns data comparing active funds to index funds, and the pattern was relentless. Not every active manager underperformed every year? Of course not. In every given year, roughly half of the active managers would beat the market. Maybe 45 % beat it. Maybe it was 55%. It would vary. But here's the thing. The managers who beat the market in one year were not the same managers who would beat it the following year.

27:47Tyler Gardner:The persistence just wasn't there. If outperformance were based on skill, you'd expect the best managers to keep on being the best managers. But what you actually saw looked almost exactly like what you'd expect from random chance. Some guys were on a streak, and then the streak would end. There's a famous study, and I want to be careful here because I'm working mostly from memory, but the numbers have been replicated so many times I'm pretty confident in the direction, if not the exact figures. Tracking top quartile mutual funds over rolling 10-year periods. The percentage of top quartile funds that remained in the top quartile in the subsequent period, about as close to 25 % as makes no difference.

28:35Tyler Gardner:Exactly what you'd expect if performance were completely random. Now, the second thing that changed, 401ks. In 1978, Congress passed the Revenue Act, which included a little provision called Section 401k. Nobody really noticed it at the time. It was aimed at letting executives defer some compensation, but a benefits consultant named Ted Benna figured out in 1980 that you could use the provision to create a tax advantage retirement savings plan for ordinary employees. So by the mid-1980s, 401k plans were spreading through corporate America, and they created something the investment industry had never really had to deal with before.

29:18Tyler Gardner:All of a sudden, millions of individual investors making their own decisions about where their money went get an annual statement telling them exactly how each option performed and a fee disclosure sitting there right next to it. And when you can see the numbers side by side, the math gets harder and harder to ignore. The third thing, the likes of Jack Bogle and Burton Malkiel, they didn't stop. Bogle kept writing. Malkiel kept writing. Bogle kept speaking. He kept showing up to conferences where he was not popular and saying the same thing he had always said. The data is here. The fees are killing you by the index.

30:07Tyler Gardner:By 1990, Vanguard had roughly$30 billion in assets, still small by industry standards, but not nothing. The first index investment trust, rechristened the Vanguard 500 Index Fund, had crossed a billion dollars 12 years after launch. 12 years. That's how long it took the most obviously correct investment idea of the 20th century to reach a billion dollars. Chapter 6. The crash that changed everything and the one that didn't. October 19, 1987, also known as Black Monday. The Dow Jones Industrial Average falls 22 % in a single day. 22%. One day. The largest single-day percentage decline in the history of the American stock market.

31:06Tyler Gardner:Active managers did not see it coming. Active managers did not get out. Active managers sat in the crash alongside every index fund investor in America. But here's what happened next. And this is the part of the story that I think people don't tell enough. The market recovered, not immediately, not painlessly. But within two years, the market was back to pre-crash levels. and by 1989, setting new highs. The investors and the managers who panicked and sold, who did the human, understandable, emotionally rational thing, locked in their losses. The investors who did nothing, who held their index funds through the terror of that Monday and the months that followed, came out the other side whole.

31:53Tyler Gardner:Doing nothing, it turned out, was once again the right move, which is a profoundly unsatisfying thing to say and a profoundly difficult thing to do. Then came the 1990s, the dot-com boom, the internet era, and here's where the efficient market hypothesis gets genuinely complicated. Because the 1990s produced something extraordinary in the history of financial manias. Stocks with no earnings, no revenue, sometimes no product, were trading at valuations that made no rational sense. In 1996, Alan Greenspan, the chairman of the Federal Reserve, not a person you would normally describe as excitable, gave a speech in which he used the phrase irrational exuberance to describe stock market valuations.

32:44Tyler Gardner:The market, Greenspan was saying, was too high. He was right, of course, but only eventually. The dot-com bubble did crash. In 2000 and 2001, the NASDAQ fell roughly 80 % from its peak. 80%. But here's what Malkiel told me about that Greenspan speech, and I think it's one of the most important things I'll say today, or maybe ever. If you had sold your equities the day Greenspan said those words, on the basis of a warning from the sitting Federal Reserve Chairman, which is not nothing, you would have missed enormous run-up. The market continued climbing for more than three years after that speech before it finally turned.

33:32Tyler Gardner:The cost of being right early in markets is often indistinguishable from the cost of being wrong. This is the trap that catches even sophisticated investors. The irrational exuberance trade was intellectually correct. The timing made it financially ruinous for anyone who acted on it immediately. The index investor's answer to this problem is the same as it always is. You don't have to predict when the turn comes. You don't have to be right about the timing. You buy continuously, you hold continuously, and you let the compounding do the work across decades. After the dot-com crash, after the rubble cleared, after the postmortems were written, the case for index investing had never been stronger.

34:22Tyler Gardner:The active managers who had gorged on tech stocks going up lost money on the way down, just like everyone else, and most of them lost a heck of a lot more. Vanguard's assets, which had been growing steadily through the 1990s, accelerated immensely. Chapter 7. 2008 and the test that never ends. I'm going to move through 2008 fairly quickly, not because it isn't important, it's enormously important, but because the story it tells is the exact same story. The financial crisis of 2008 was different in its mechanism from previous crashes. It wasn't a tech bubble, it was a housing bubble, amplified by financial instruments of extraordinary complexity that allowed risk to accumulate invisibly until it exploded all at once.

35:13Tyler Gardner:The S &P 500 fell about 57 % from its October 2007 peak to its March 2009 trough. Active managers, by and large, did not get out. The few who did, and there were some genuine heroes of that period, people who had been warning about the housing market for years, were largely lucky in their timing, or were taking on so much short-side risk that they couldn't have sustained it indefinitely. The market recovered, took about four years to get back to pre-crisis levels, and then it kept going. The decade that followed 2009 was one of the greatest bull markets in American history. The investors who held their index funds through the bottom, who did not sell in March 2009 when the headlines were apocalyptic and your neighbor was telling you to put everything in gold and canned goods.

36:04Tyler Gardner:Those investors were rewarded with returns that are almost difficult to believe in retrospect. The investors who sold at the bottom or near it locked in losses and then watched from the sidelines as the market doubled, then tripled, then quadrupled. The lesson of 2008 is not a new lesson. It's the same lesson. It has always been the same lesson. Markets go down, they come back up. The cost of panic measured in returns is staggering. Chapter eight, the man behind the book. Now, I want to bring this back to Bert Malkiel because I think the personal dimension of this story matters as much as the data.

36:45Tyler Gardner:Here's a man who published the definitive popular argument for index investing in 1973, who has updated it, defended it, and refined it through 13 editions and 50 years, who sat on the board of Vanguard and helped shape the investment philosophy of the firm that would eventually manage over$9 trillion, who taught at Princeton, who was the dean of Yale School of Management. And I asked him, have you ever felt genuine fear about your financial situation, not as an academic exercise, but actual fear. His response? Yes, of course. Immense fear. All the time. And yet, he did nothing. I want to dwell on that for a second, because I think it's easy to read that answer and dismiss it.

37:38Tyler Gardner:Easy to say, well, he's Burton Malkiel. He's been right about this for 50 years. Of course, he can hold through fear. But that's backwards. He doesn't hold through the fear because he's Burton Malkiel, he's Burton Malkiel partly because he holds through the fear. The discipline came first, the results followed. He also told me something about teaching that I think goes to the heart of what this podcast is trying to do. He said he preferred teaching freshmen to PhD students because freshmen asked grounded, realistic questions coming from a genuine place of not knowing. They hadn't yet been trained to ask sophisticated questions that often obscure simple truths.

38:20Tyler Gardner:They asked questions that actually mattered. That was his primary audience for a random walk down Wall Street, the person sitting in the freshman lecture hall who doesn't know what an expense ratio is and deserves to understand why it matters. That's my audience too, and it's why this episode exists, and it's why this entire endeavor exists. Chapter 9. Where We Are Now and the New Tension I'd be doing you a disservice if I didn't address what is genuinely the most interesting intellectual wrinkle in the index fund story right now. Malkiel wrote a piece in the Times last year warning about stretched valuations and a dangerous concentration of index funds in a handful of technology stocks.

39:07Tyler Gardner:The 10 largest companies in the S &P 500 now represent roughly a third of the entire index by market weight, which means that when you buy the whole market, you're actually buying a portfolio that is meaningfully concentrated in Apple, Microsoft, Nvidia, Amazon, Alphabet, Meta, and a handful of others. This creates a philosophical tension that I pushed Malkiel on directly. If prices are always right, or in his language, always wrong, if the market is efficient, then that concentration is rational. Those companies are worth what they're worth. But if something worries him enough to write an op-ed about it, is that not a form of market timing?

39:50Tyler Gardner:I asked him what advice he would give to all those worried about a potential over-concentration or bubble in certain stocks. His answer was careful, and as should come as no surprise, historically grounded. He said, yeah, the market is absolutely concentrated, but the market has always been concentrated. Railroads, steel companies, computer stocks in the 80s, internet stocks in the 90s, AI now. Concentration is not new. The sector that dominates the index shifts over time, and the investors who tried to tilt away from those dominant sectors, who said, this is too concentrated, I'm going to underweight tech, have historically paid for the bet in underperformance.

40:40Tyler Gardner:Then he came back to Greenspan.

41:10Tyler Gardner:wrong. His answer to what the committed index investor does when even Burton Malkiel is worried, buy an index fund, hold an index fund, because you will never, never, never, never outguess the market. And yes, he said never four times. There's something almost maddening about the consistency of that answer and also something deeply reassuring. The final chapter, what Malkiel told me about retirement. The last thing I want to share from our conversation is the part that I'll personally remember the longest. I asked him what retirement actually means to him, because my listeners, and maybe you're one of them, are entering it both excited and terrified in roughly equal measure.

41:58Tyler Gardner:The freedom is real. The uncertainty is also real. And for a generation that watched their parents work until 65 and then have a pension check arrive every month, the shift to self-directed retirement can be genuinely disorienting. Here's what Burton Malkiel, who is 93 years old and still writing and still as engaged as anyone I've ever met in my life, told me. On the practical portfolio side, he argued that TIPS, Treasury Inflation Protected Securities, and municipal bonds yielding 4 % to 5 % with a positive real return, both of those items belong in your portfolio as the fixed income component.

42:42Tyler Gardner:That is tips and municipal bonds. During your accumulation years, you should be equity heavy, 100 % stocks when you're young, if you can stomach it, and in retirement, not a dramatic shift, still a heavy equity allocation, not the whole portfolio, but the lion's share, because the historical data still supports equities as the best long-term inflation hedge and the best engine of real wealth growth over time. That's the practical answer. Maintain equity exposure longer than you think you should. Don't flee to 100 % bonds just because it feels safer. The math simply doesn't support it, but do focus on tips and municipals.

43:25Tyler Gardner:But then he said the thing I'll remember forever, and it had nothing to do with asset allocation. His best life advice, especially in retirement, always and forever, stay engaged. Not for retirement, for life. Stay engaged. Beyond his writing, I asked him which writers he is currently reading, and he cited a writer he loves and thinks we should all read as much as possible. and I personally couldn't agree more, Jason Zweig, the Wall Street Journal columnist and author who has spent his career making behavioral finance accessible to ordinary people. Malkiel is not retiring from being interested in things.

44:09Tyler Gardner:He is not stepping back from ideas. He is not counting down the days until he can stop work. He never has been. In fact, he told me that he knew in his 30s, after spending his pre-academic professional life with Smith Barney on the OTC trading floors, that he wasn't worried about money from that point forward. He was, and always has been, a teacher who simply wants to help the world think through concepts, especially if you're not a ding-dong PhD student asking overly complex questions that are of no practical value to anyone. My words, not his, partially in jest. The money matters. I'm not going to stand here and tell you that the money doesn't matter.

44:51Tyler Gardner:Getting the financial piece right, the index funds, the expense ratios, the asset allocation, the tax advantage, municipal bonds, all of that matters enormously and gives you the options that nothing else can. But the number in your brokerage account is not the thing that gets you out of bed. Stay engaged, keep reading, keep being curious about things, keep showing up for the ideas that make you feel alive. And hopefully we can all live well into our 90s and continue to shape the way that others think and act in this world, hopefully like Malkiel for the better. And at 93 years old, that is exactly what Burton Malkiel is doing with his time.

45:34Tyler Gardner:I hope you enjoyed a slightly different format this week. And if nothing else, remember the next time you have the opportunity to sit down with one of the most influential voices in personal finance history, hit and record before you click end meeting and always have a backup plan. As always, hope this gives you something to think about throughout the week ahead. Thanks for tuning in to your Money Guide on the Side. If you enjoyed today's episode, be sure to visit my website at tylergardner.com for even more helpful resources and insights. And if you're interested in receiving some quick and actionable guidance each week, don't forget to sign up for my weekly newsletter, where each Sunday I share three actionable financial ideas to help you take control of your money and investments.

46:22Tyler Gardner:You can find the signup link on my website, tylergardner.com or on any of my socials at Social Cap Official. Until next time, I'm Tyler Gardner, your money guide on the side. And I truly hope this episode got you one step closer to where you need to be.

From the publisher

Pre-order Tyler's book, Real Wealth, at tyler.gardner.com/book

And as always, a MASSIVE thank you to this week's sponsors:

Fabric: → ⁠meetfabric.com/tyler⁠ because if you have dependents, and you don't have term life, getting term life insurance is the financial step you need to take right now.

Gelt: ⁠→ ⁠joingelt.com/tyler because Q2 is where strategic businesses make game-changing tax moves

LMNT: → ⁠drinklmnt.com/tyler⁠ Become an INSIDER, just order the INSIDER Bundle–four boxes for the price of three, best value they offer–and get early access to limited time flavors and cool surprise gifts along the way.

Facet: → ⁠⁠facet.com/tyler⁠ for an exclusive $550 kickstart offer! And see for yourself why I've partnered with Facet for almost TWO YEARS!

And now on with the show notes!

What if the most important investing conversation you’ve ever had… never got recorded?

That’s what happened here.

In this episode, Tyler reconstructs a lost interview with Burton Malkiel, author of A Random Walk Down Wall Street, and uses it to tell a bigger story — one about index investing, behavior, and why the simplest strategy is still the hardest to follow.

Because this isn’t just about theory.
It’s about what actually works in real life — and why people still struggle to stick with it.

In this episode, Tyler walks through:

The origin of index investing — and why Wall Street fought it for decades

Why most active managers fail to beat the market after fees

The role of academics like Markowitz, Fama, and Samuelson in shaping modern investing

How fear and behavior — not knowledge — derail most investors

Why trying to time the market (even when you’re right) can still cost you returns

The risk of concentration in modern index funds — and why it’s not a new problem

Malkiel’s core principle: you will never consistently outguess the market

Tyler also shares one of the most important takeaways from the conversation:

Even Burton Malkiel feels fear. He just doesn’t act on it.

And that’s the difference.

The core idea:

Investing isn’t about being right. It’s about staying consistent when it’s hardest to do so.

The episode closes with a broader reflection on retirement — not just how to invest, but how to live.

Because according to Malkiel, the goal isn’t to stop working.

It’s to stay engaged — with ideas, with learning, and with life itself.

If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps.

Hope this gives you something to think about this week.

More from Your Money Guide on the Side

All 65 episodes
My Interview with Burton Malkiel (That You Will Never Hear)Your Money Guide on the Side · 42 min
Listen in VO