The Profound Benefits of Not Winning

I’m not sure how many of you out there are fans of baseball – or even understand how it works. 

But in its’ slow march across the spring, summer and autumn months in the US, the 162 game season produces an outsized number of surprises – some glorious, some painful, some absurd, some very, very pedestrian.

One of my favorite parts about the game is how it occasionally spurs some spectacular sports writing: Stories that transcend the day-to-day and become profound in their ability to raise the mundane to the universal.

Such was the case recently, when Sam Anderson wrote in the New York Times about the Chicago White Sox’ monumentally terrible season, in which they lost 121 of the their 162 games (74.69%), setting a new Major League Baseball record for losses in one season. 

In his sublime paean to awfulness, Anderson artfully turns the White Sox’ woeful season into a glorious universal truth. He writes:

“To live is to lose, in all the many senses of that word — to lose socks, friends, arguments, opportunities, brain cells and everything else. And while we can all agree that losing is basically the absolute worst, we must also acknowledge that it is underrated. 

Losing, obviously, makes winning possible; it is the negative space in which success exists. But its virtues go far beyond that. 

To lose is to acknowledge that, in spite of all your hopes and efforts, things have not gone your way — and so, to maintain the peace, you will walk away. It is a civic miracle that keeps us from tearing each other’s heads off. 

To lose, and to deal with loss, is one of the most profound things a human can do.”

I bring this up not because I am a fan of the White Sox (for the record, I am a fan of the other Chicago baseball team, the sometimes equally benighted Cubs), but rather because of its resonance with startups and founders.

By most accounts, 90% of all startups fail. We can quibble on the precise numbers and how they are determined, but as a rule let’s say it’s around 90%. Even worse than the White Sox…

In the US and some other markets, this fact is normalized and accepted. Founders start a company; it often fails and they dust themselves off and start another one – many times with the same investors. They keep at it, learning as they go, until they (mostly) find success. 

There is no stigma in this, in fact, some investors are MORE willing to put money into a founder’s company if s/he has failed in the past. It’s part of the learning process and almost expected of a startup founder.

Sadly this is not yet so acceptable in the Southeast Asian startup ecosystem. Failure is shame, failure is bad, failure connotes weakness. Part of this, I believe is due to the still young and developing nature of ecosystem and part is due to the intricate cultural relationships amongst failure, shame and face that area found regionally. 

To be clear, I am not expecting the local Southeast Asian startup ecosystems to mirror or behave like those found in the US or in Western Europe. But on the other hand, ignoring the role that failure  plays in building a stronger startup culture can’t be ignored either.

As my friend Malaysia-based VC  Kevin Brockland writes in a recent post, referring to failure in Southeast Asian startup ecosystems: “…we sweep it under the rug, hide it in the closet, bury it deep, never to be spoken of again…”

Thankfully, this is beginning to change: More regional VCs and founders are speaking about failure now than they were 4 or 5 years ago. Smart investors and Directors now understand that this is part of the process and don’t excoriate founders for failing to deliver unicorns or glamourous M&A exits.

But I feel that more can be done to normalize failure and raise its acceptance level in the regional startup ecosystem. Nobody likes to fail and nobody encourages their friends, family or investees to do so. But it does happen and as a community, we need to become more accepting of it.

As my friend Kevin says: “…the treatment of failure is the differentiator between which startup ecosystems will advance and which will lag behind.” 

So, to founders and their investors, family, friends and other supporters, let me echo that plea for more understanding and acceptance of a founder’s failure and a request to view it more as a stop along the way to success, rather than an endpoint. Let’s focus instead on building the ecosystem to support that journey and those post-failure opportunities.

As Anderson says about failure in his article on the While Sox: “Losing … makes winning possible it is the negative space in which success exists.”

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NOTE: While I’ve been fortunate enough to have had a few small exits, I lived through nearly twice as many failures in order to get there – and no, it’s not easy nor pleasant.

If you’re interested in reading Sam Anderson’s article on the White Sox, you can find it here (behind a paywall): https://www.nytimes.com/2024/09/24/magazine/chicago-white-sox-loss-record.html . 

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