The Best Financial Advice:

The holidays are a time for relaxing, helping the less fortunate, showering family and friends with love and attention—and, sometimes, for smiling and nodding through unsolicited stock tips from an overbearing relative who has been sampling the eggnog.

Good advice can make careers and forever change lives for the better.

But good advice can make careers and forever change lives for the better. So The Wall Street Journal asked an array of prominent people who manage, invest, study and write about money to share the single best piece of financial advice they ever received—or gave.

The respondents included investors who collectively have earned billions of dollars for clients and themselves; founders and owners of businesses that are household names; and Nobel laureates who shaped the world’s understanding of the forces that drive the stock market.

A leading federal judge who has presided over cases related to the financial crisis shared his thoughts, as did an agent who has negotiated some of the most lucrative contracts in the history of sports and an adviser who helps clients recover financially after a divorce.

In most cases, the recommendations are easy to follow today. Some reflect conventional wisdom, while some fly in its face. Not every tidbit is consistent with all the others. The responses, some of which were edited for clarity, appear below.

But first, a word of caution: Like all advice, it should be weighed soberly—ideally, at a good distance from the eggnog.

Robert Shiller, Nobel laureate in economics (2013) and professor at Yale University

The best advice I ever got was the buy signal from my dissertation adviser at MIT and later co-author, Franco Modigliani, very close to the bottom of the market in the early 1980s.

I put virtually [all] my portfolio 100% into value stocks then, even though the conventional academic wisdom was then that one should be more diversified. I didn’t start taking it out substantially until sometime around the turn of the century, around 1999, though I don’t remember exactly. I read very carefully his paper with [Richard] Cohn published in the Financial Analysts Journal in 1979, “Inflation, Rational Valuation and the Market.” It concluded that the stock market was 50% undervalued.

Actually, that was an understatement—from 1982 to 2000 the S&P 500 total-return index went up something like 20-fold. This investment advice created another miracle for me, for it inspired me to write my article “Do Stock Prices Move Too Much to Be Justified by Subsequent Changes in Dividends?” published in the [American Economic Review] in 1981 and mentioned prominently in the Scientific Background paper for the Nobel Prize.

So Franco’s advice not only got me phenomenal returns, it also helped me win the Nobel Prize. You can’t get better investment advice than that.

Scott Boras, professional sports agent and founder of Boras Corp.

My labor-law professor once told me: Business and money don’t breed warm feelings. Ninety-five percent of what people say about you is going to be negative. And remember, that means that you are doing a good job.

William Bernstein, neurologist and investment manager at money-management firm Efficient Frontier Advisors

The best financial advice I ever got was from Fred Schwed’s classic book, “Where Are the Customers’ Yachts?”, first published in 1940. Schwed wrote: “Like all of life’s rich emotional experiences, the full flavor of losing important money cannot be conveyed by literature. Art cannot convey to an inexperienced girl what it is truly like to be a wife and mother. There are certain things that cannot be adequately explained to a virgin either by words or pictures. Nor can any description I might offer here even approximate what it feels like to lose a real chunk of money that you used to own.”

I’ve never forgotten that. Finance is never, ever, a theoretical exercise; you’re never half as detached from portfolio losses as you think you will be.

Michelle Smith, chief executive of Source Financial Advisors and a specialist in financial planning for wealthy people going through divorce

My great-grandmother taught me: Don’t ever give up your ability to make your own money.

John C. Bogle, founder of Vanguard Group

The best way to own stocks is to own an index fund.

Bill Gross, co-chief investment officer of Pimco

An investor’s inner time clock is crucial to getting in and getting out of markets. If the normal cock-a-doodle-doo of the rooster is at 6 a.m., there will be some investors who wake up at just past midnight—far too early for timing a market bottom or top. And some who wake up at 10 or 11 a.m. like a college student—far too late. Learn to recognize when your clock generally goes off, and work on getting it to ring at 6 a.m.

Scott Adams, creator of ‘Dilbert’ and author of ‘How to Fail at Almost Everything and Still Win Big’

The best financial advice I ever got was “Price yourself high and see what happens.” Humans aren’t good at knowing their market value. When I started doing paid speaking engagements I had no idea how to price myself. A mentor told me to quote an absurdly high price. The client accepted it without hesitation and offered to pay my travel expenses as well. I no longer underprice myself.

Hal Steinbrenner, co-chairman of the New York Yankees

The one thing about money that my dad always instilled in us was to just be straightforward, upfront and honest. Don’t play games with people’s finances. Some deals are going to happen because of that, and some deals aren’t. It’s a good way to conduct yourself in life in general, really; there are no downsides.

Jed Rakoff, U.S. District Judge, Southern District of New York

When I turned 43, I confided in one of my mentors, Judah Gribetz (former counsel to New York Gov. Hugh Carey), that I was thinking of pursuing a federal judgeship. He asked me: “How much have you put away for your (three) daughters’ college education?” I admitted it was not much.

He said, “A judge can’t be truly independent if he’s always worrying about finances. Don’t apply until you’ve saved enough to put all your kids through college for four years. And don’t forget that college costs these days increase at twice the (predicted) inflation rate!”

It took me another nine years to save up to meet this goal, but when I then applied to be a federal judge, I knew I wouldn’t have to worry about anything but doing the job. It was the best investment advice I ever received.

Charles Schwab, chairman of Charles Schwab Corp.

A friend said to me, Chuck, you’re better off being an owner. Go out and start your own business.

Alexandra Lebenthal, chief executive of Lebenthal Holdings, a money-management firm

Read all your statements and prospectuses closely. Don’t depend on your adviser to do it for you. Everyone has the responsibility to know what they are investing in.

Joe Mansueto, chief executive of financial research firm Morningstar

An investor should think like a business owner, not a renter. Most businesspeople don’t get up in the morning and ask whether they should sell their business that day. If they own a pizza shop, they don’t think about whether what they really should own is a shoe store instead. They show patience and persistence and try to understand their underlying business better so they can earn the greatest return for the longest period of time.

So investors are in many ways misled by stock-market volatility. The values of the underlying businesses just don’t change as quickly as stock prices do. You really don’t have to watch those changes hawklike day after day.

It is in a lot of people’s interests to get you to do something. Advisers and brokers earn commissions, fund companies want you to bring your assets to them. There are a lot of forces at work in the investment industry to get people to move, and there’s not really a countervailing force to encourage you to do nothing. But you should.

William Sharpe, Nobel laureate in economics (1990) and emeritus finance professor at Stanford University

Best advice I’ve gotten (from Armen Alchian, my mentor at the University of California, Los Angeles, when I was a graduate student): When thinking about markets, assume that prices are set by the interactions of buyers and sellers, each trying to maximize their own welfare. The best advice I’ve given: In securities markets, don’t expect a free lunch; diversify broadly and keep your costs low.

Sallie Krawcheck, owner of 85 Broads, a women’s networking group, and a former senior executive at Bank of America and Citigroup

The best financial advice I ever received was not to buy a financial product that you didn’t understand and not to buy it from a person who couldn’t explain it so that you could understand it. Think [Ponzi schemer Bernard] Madoff: Any number of people didn’t understand how he was making the steady returns he was making, but they didn’t question it because it was such a good thing.

Maurice “Hank” Greenberg, chairman of Starr Insurance Holdings and former chairman of American International Group

Advice you have in one era is not advice you can employ endlessly. I would nonetheless give the advice to others: Invest in what you are doing, show your own confidence in what you are doing. But keep in mind there are much broader issues that must be considered today than would have been in the past, issues of regulation and the politics where you are doing business, and the impact that could have on your company, or any company.

Richard Sylla, professor of the history of financial institutions and markets at New York University

The best financial advice I ever received was advice that I also provided, both to myself and to Edith, my wife. It was more than 40 years ago when I was a young professor of economics and she was a young professor of the history of science. I based the advice on what were then relatively new developments in modern finance theory and empirical findings that supported the theory.

The advice was to stash every penny of our university retirement contributions in the stock market.

As new professors we were offered a retirement plan with TIAA-CREF in which our own pretax contributions would be matched by the university. Contributions were made with before-tax dollars, and they would accumulate untaxed until retirement, when they could be withdrawn with ordinary income taxes due on the withdrawals.

We could put all of the contributions into fixed income or all of it into equities, or something in between. Conventional wisdom said to do 50-50, or if one could not stomach the ups and downs of the stock market, to put 100% into bonds, with their “guaranteed return.”

Only a fool would opt for 100% stocks and be at the mercies of fickle Wall Street. What made the decision to be a fool easy was that in those paternalistic days the university and TIAA-CREF told us that we couldn’t touch the money until we retired, presumably about four decades later when we hit 65.

Aware of modern finance theory’s findings that long-term returns on stocks should be higher than returns on fixed-income investments because stocks were riskier—people had to be compensated to bear greater risk—I concluded that the foolishly sensible thing to do was to put all the money that couldn’t be touched for 40 years into equities.

At the time (the early 1970s) the Dow was under 1000. Now it is around 16000. I’m now a well-compensated professor, but when I retire in a couple of years and have to take minimum required distributions from my retirement accounts, I’m pretty sure my income will be higher than it is now. Edith retired recently, and that is what she has discovered.

John Rogers, chairman of Ariel Capital Management, a Chicago-based investment manager

My basketball coach, Pete Carril [head coach at Princeton University from 1967 to 1996], said you had to think about your teammates first. There’s no excuse for acting selfishly and putting yourself ahead of your teammates. That’s been critical to me in business: looking out for the best interests of the team and our investing clients rather than my own.

When you think about it, in any organization—whether it’s a business or a nonprofit—it’s critical that people know you are thinking about the team first, because then they’ll want to work with you as someone who’s looking out for them. They will work harder when they know the leaders are doing their best to help everyone around them succeed.

Mark Cuban, owner of the Dallas Mavericks

Pay off your debt first. Freedom from debt is worth more than any amount you can earn.

Larry Swedroe, director of research, Buckingham Asset Management, an investment-advisory firm

I was taught that the strategy to get rich—take concentrated risk, typically with your labor capital/business—is entirely different than the strategy to stay rich, which is to minimize the risks we take, diversify the ones we take as much as possible, keep costs low, tax efficiency high, and don’t spend too much.

Seth Klarman, president of the Baupost Group, a Boston-based hedge fund

Wally Carucci [of brokerage firm Carr Securities], a dear friend who passed away this last year, was an amazing mentor to me 30 years ago. The wisdom he gave to me was “You have to feed the birdies when they’re hungry.”

There are two ways to interpret that. There’s the superficial meaning: Don’t forget to sell, and always remember that it’s easier to buy than to sell. But what he was really talking about is that liquidity is ephemeral. Wally was best known for his research on very illiquid, thinly traded stocks. What he meant on the deeper level is that when people want to take you out of an asset for a full price, don’t hold out for the last dollar.

Carl Icahn, activist investor

When friends and acquaintances are telling you [that] you are a genius, before you accept their opinion, take a moment to remember what you always thought of their opinions in the past.

Jane Mendillo, chief executive of Harvard Management Co., the university’s endowment

“Take the long-term view” was the best advice I ever received. If you take the long-term view, you will see things others miss. Nearly everyone thinks about next month, next quarter. Jack Meyer, who ran [the] Harvard endowment for 15 years, taught me that when you think about multiple years or even decades you see opportunities to create value others might not see, and you make different judgments today as a result.