The Winners Write History [Startup Edition]

History is always written by the winners. When two cultures clash, the loser is obliterated, and the winner writes the history books-books which glorify their own cause and disparage the conquered foe.

-Winston Churchill

I agree with Churchill’s quote.

There’s the counterpoint that in actuality, everyone gets to write history and historic works are still leftover from the conquered. But by and large winners write history because the world cares about winners. The founders of the US didn’t study Carthage on how to build a great, lasting nation. They studied Rome even though Rome was almost destroyed countless times, two separate times by Carthage (the third Punic War wasn’t a fair fight).

We know the top swimmer in the world, maybe the second best, but unless you’re obsessed with swimming, you don’t know the 3rd best. We don’t know the 7th best tennis player in the world, the 2nd best gymnast, 2nd best sprinter, etc.

We want to read and learn from winners. We read books by winning investors, winning entrepreneurs, winning athletes, winning chefs, winning actors. We listen to talks by winners and the philosophy of winners.

This is a decent bias to have, but it’s still a bias. I was at a dinner where my friends who were at PayPal in its later days were saying how it would have failed simply if US regulators pushed just a little bit harder. If PayPal failed, we wouldn’t have had YouTube, Yelp, LinkedIn, Palantir, Tesla, SpaceX, Affirm, OpenDoor, and the seed financing of Facebook and countless other tech companies. Europe may have had multiple companies similar to PayPal that failed due to their greater regulatory pressure. People just as smart and hardworking exist in Europe, and it could have been the right time and right market, but they may not have been in the right place.

After reading many books written by “winners” in all categories that opine on their philosophies, I would say there are correlations. At the high level, they all value hard work, constant improvement/learning, and merit. Beyond that, they all have their own unique strategies, structures, and principles they follow.

Companies have founding stories. They are the Adam and Eve stories of startups. The creation story. They’re bullshit. Not necessarily 100%, but they have a hefty dose. Few companies ever know where they’re going to end up when they start out. I have a vision right now, but I also have the pattern recognition to be conscious of the fact that we’ll likely not end up following our exact plan.

Winners are forgiven. Michael Vick was convicted of running a dog fighting ring, but a couple years later, he was MVP and our POTUS (Obama at the time):

was happy that we did something on such a national stage that showed our faith in giving someone a second chance after such a major downfall.

You can murder dogs, but all is forgiven if you’re the best at playing with a pigskin. I’m not saying one should be condemned for life for one mistake. I’m saying that people like winners, sometimes no matter their past or even current actions.

This is true of evil “winners”. I know a number of people who love Putin. Some women I know think Putin is hot and funny. This is the same person who was part of the KGB, murdered innocent people, orchestrated murders, stole property, committed heinous crimes, and singlehandedly reduced Russia’s economy to a GDP that is smaller than Italy. Now, no respectable non-Russian wants to do business there. But Putin won Russia. There is no disputing that. Putin is also clever with his remarks and propaganda. None of this may be good for Russia, but it is good for Putin.

The people behind many companies in the valley could objectively be seen as fucking weird. If they weren’t winners, they’d be social outcasts.

A friend told me how one time there was a guy stalking his company at midnight. It was a large man in an empty parking lot in a car with binoculars looking in at them and watching them work. That’s creepy. That was Reid Hoffman. Similarly, there was a CEO who came into their office and started talking to their engineers. The CEO was trying to poach them for his own startup. That’s a douche move. That was Zuck. The same person who had a business card that read “I’m CEO, Bitch.” Would you work for someone who had a business card that said “I’m CEO, Bitch”? Imagine the type of person who would have that on their business card, and imagine the type of person who would go to work for that person.

People do change, but it’s interesting to think of these companies early on and how the founders acted back then. My point is that it didn’t matter how they acted because they won. Maybe they matured in the process of winning, but if they didn’t, people will revere them all the same.

The graveyard of startups is massive. The case studies on these failures is a recent phenomenon. It’s from the ethos of Silicon Valley to be ok with failure and to allow second and third chances. The heart of this is because one can be an extraordinary entrepreneur and still fail due to numerous reasons beyond one’s control. The biggest question is how/why they fail.

My issue with many of the postmortems on startups is that the CEOs don’t tell the full truth. Their incentive is to be therapeutic to themselves and to make themselves look good to potential employers and future investors. You would need an objective third party to come in to interview and talk with all parties involved to understand what truly happened. A speaker for the dead.*

I know a company that found product market fit, but the CEO decided he didn’t enjoy that business. The CEO fought with the board and the board acquiesced. He pivoted and ended up never finding product market fit again. He failed. He wrote a postmortem where he never acknowledged the product market fit he found. People praised him for his transparent postmortem and how brave he was in the telling of his struggles. I guess some losers get to write their own history.

It’s a recent phenomenon of winners being taken down. It’s like our culture started reversing what is considered good and what is considered bad. Being a victim used to be a bad thing. Now, victims are empowered and don’t be a “victim blamer”. Being fat used to be a bad thing, now it’s fat-shaming to call someone fat. Add in slut-shaming. People at the top of their respective fields were taken down by the #metoo movement. Many rightfully so. Our society is constructing an archetype of the ideal victim as the biggest loser because of everyone else’s fault. The ideal victim, in my mind, is the one who overcomes and becomes a winner. Even if our society temporarily sympathizes with victims, I think it’s in human nature to respect and ally with the winners. I’m all for empathy, but I hope victims aren’t the new winners… or we’ll become a society of losers.

In the startup world, the biggest winner taken down was Travis Kalanick (former CEO of Uber). People have short memories; PR 101 is get out all the bad news at once and trickle out the good news. Uber did the exact opposite. It was an onslaught of bad news stories after bad news stories. I’m not sure how/why they let this happen… they’re smart people and they were running a hyper-scaling company so they may have been distracted… but it happened nonetheless. The result was an overhaul of corporate governance at Uber, senior leadership being switched out including Travis, and a revamp of company culture accompanied by a “we’re sorry” campaign that no one gave a fuck about. The winners were the media. They got what they wanted. Travis is still a billionaire and running a new company, but that wasn’t what he wanted… he wanted to run Uber. Uber’s S-1 was full of apologies for their past management (before Dara took over in September 2017). Yes, they’re so sorry about the people who grew the company massively. Without the internal turmoil, Uber would probably be a much larger multiple of Lyft than they are today.

The conclusion of this is to be a winner. Be someone or build something people care about. Why do something if you aren’t going to be the best. Being 2nd is sadly a waste. No one cares and there is a generally a power law/natural winner take all in many markets.**

*The only reason we care about Travis’ insane past failures is because he happened to later become co-founder and CEO of one of the largest private tech companies in a generation. Even then, this video has only 68K views right now.

**There are some exceptions with Pepsi and Cola but even then the winner is clear.

A side note to this is that there are leaders who succeed at times even despite themselves, and they think very highly of themselves. There are also leaders who are hardcore superstars who no one can emulate. Both of these remind me of my favorite moment in One Punch Man where the hero is by far the strongest in the universe; He can defeat demons and aliens with one punch. When asked how he trained to get his powers, he responded that he does (read right to left)

As if that is all that’s needed to become the strongest being in the universe.