Fat, Happy, And In Over Your Head

Having more than you need can be a liability masquerading as an advantage, and no sense of “enough” can look like ambition but often leads you over the edge.

This applies to everyone, from companies to careers to investments.

First, a little story about WeWork and a retired ski racer.


WeWork is rumored to be going public at a $10-$12 billion valuation, which by any definition is a wild success. What’s still thought of as a startup would instantly be a large-cap corporation eligible to be in the S&P 500. A deca-unicorn.

Congratulations WeWork. You’ve won.

But of course no one feels that way. WeWork raised $12 billion from private investors and was valued at $47 billion a few months ago, so a $10 billion valuation feels like a corporate bellyflop.

I’m saying this with the delight of hindsight, but it’s not hard to imagine a world where WeWork turned down Softbank’s huge checks, raised a third as much capital from private investors at a quarter the valuation it did, built a good business that still had glitz and beautiful offices, and went public at (I’m making this up) a $5 billion valuation – great by any measure, especially given the lack of any real innovation in the business.

Everyone would have been happy in this world, because no one would anchor to the $47 billion valuation. The company’s growth wouldn’t be as high, it wouldn’t have bought a private jet or invested in turmeric coffee creamer, and the CEO wouldn’t have cashed out three-quarters of a billion dollars. But a sense of “enough” – enough capital, enough growth, enough valuation – would have left WeWork in a better spot than it’s in today. I suspect every investor and employee involved with the company now know this, but it’s too late.

The irony is if you go back six months and ask investors to quantify WeWork’s success, most would say, “They’ve raised $12 billion and are valued at $47 billion.” Fundraising and valuation were the metrics of business success. Public markets have a different view – they care more about good businesses than big fundraises – so the response to WeWork has been a finger wag. If you don’t cultivate a sense of “enough,” someone else will you give you one on their terms.

Now the ski racer.

Marcel Hirscher is the greatest ski racer in history, winning the World Cup Overall title in each of the last eight years. Few of you have heard of him because ski racing is tiny in America. But in Europe he’s like Michael Jordan.

Hirscher announced his retirement last week. It baffled many; It’s like if Jordan retired in 1993. Nowhere close to slowing down, his margins of victory just months ago were the highest they’ve ever been. He probably had 5-8 more good years in him. He could have kept winning, kept earning millions, the king of his sport.

But he’d had enough.

“I always wanted to quit when I knew I could still win races,” he said. He avoided major injuries and wanted to stop before his luck ran out. “I want to play football with my little boy, climb the mountains and do things without any serious injury or pain.”

Few athletes do this, but it’s hard to describe how admirable it is.

Going out on top means always be known for your success, not the wincing, shell of your former self that often happens to athletes who are forced out at the bitter and quiet end. Jerry Seinfeld, who ended his show when its future was bright, said the only way to know where the peak is is to experience the downturn, which didn’t interest him. He had enough. Far from ending his career, going out on top made Seinfeld hyper marketable and ballooned the value of his previous work by creating a cult following. WeWork may face the opposite, as there’s a long history of employees and customers not wanting to associate with damaged goods.

The idea of having “enough” might look like conservatism, leaving opportunity and potential on the table.

I don’t think that’s right.

“Enough” is realizing that the opposite – an insatiable appetite for more – will push you to the point of regret.

The only way to know how much food you can eat is to eat until you’re sick. Few try this because vomiting sucks more than any meal is good.

For some reason the same logic doesn’t translate to business and investing, and many will only stop reaching for more when they break and are forced to. This can be as innocent as burning out at work or a risky investment allocation you can’t maintain, all the way billionaires who resort to stealing because every dollar is worth reaching for regardless of consequence. Whatever it is, the inability to deny a potential dollar will eventually catch up to you.


My partner Craig says we shouldn’t worship unicorns. We should admire crickets. Crickets produce more body weight per gram of food eaten than any other farm animal. A lot of unicorn companies are huge because they raised a ton of money, but the cricket business is one that raised a little money, said, “that’s enough, that’s all we need, let’s go build a real business” and still prospered. They will likely become the most sustainable businesses – and the most valuable long term – because their proactive sense of “enough” keeps them from getting in over their heads.

Individuals can do something similar. John Bogle, the Vanguard founder who passed away earlier this year, began his book with the following words. I’ve cited this many times, but it’s one of the few things that can’t be said enough:

At a party given by a billionaire on Shelter Island, Kurt Vonnegut informs his pal, Joseph Heller, that their host, a hedge fund manager, had made more money in a single day than Heller had earned from his wildly popular novel Catch-22 over its whole history. Heller responds,“Yes, but I have something he will never have … enough.”


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