Tangential Tuesdays #73

Desire to win, twitter

Hello - a new week has arrived. It has been about a month and a half since I started working from home and started quarantine.

One of my favorite parts of COVID-19 is how fun it is to speculate wildly on what will happen. Is this a depression? When will we go back to work? What are the first-order effects? What about the second-order?

Even more fun is writing about these topics on the internet and getting to look back and see how laughably wrong you were.

For instance, here's me at the beginning of the quarantine:

"Thumbtack is essentially mandatory work from home starting this Thursday due to COVID19. Probably for an absolute minimum of 2 weeks …it's going to be interesting. I don't think I've ever worked more than two straight days remotely before."

A minimum of 2 weeks? LOL, that is the understatement of the year. At the most recent Thumbtack board meeting, we established that there is a genuine possibility that we don't return to the office for the rest of 2020.

*deep breath*

So with that fun news, I figured I would try out speculation take 2. One thing I've learned when it comes to speculating on topics I know nothing about is to not hedge. The hotter and more unsubstantiated the take, the more fun it becomes.

So here we go:

  • We will overestimate 1st order effects and underestimate 2nd order effects. (example: economy starts to reopen faster than people expect, but longer to recover than we expect)

  • The economy will slowly begin to reopen in June

  • Tech companies won't go back to their offices in SF this year

  • Two years before the S&P 500 reaches a new all-time high

  • Things eventually return to normal, but we never get an effective vaccine


Desire to win

Bob Crandall loved meetings, the longer the better. He once scheduled a meeting for 5 A.M., and one of the participants showed up in his pajamas. During staff meetings there was never a bathroom break, ever. The participants either waited for lunch or dinner or excused themselves when duty called. Crandall, for his part, never did have to get up. His subordinates on occasion would slyly pour him cup after cup of coffee just to see if they could force him to take an unscheduled break, but they never succeeded.

As I continue plowing my way through Hard Landing, there’s one particular theme that has been striking.

The intense desire to win that all of these airline executives had. It’s also a quality I find attracts me to companies, friends, and people in general.

Recently I’ve been questioning whether this quality is actually desirable. In an industry like the airline business - maybe. But most businesses are not the airline business - and life is certainly not anywhere close.

Viewing life as a competition as a recipe for misery. But still - a part of me tugs… shouldn’t you want to be the best even if you’re destined to fall short?

I think the boring truth is that you need balance. On any team, you need people with this intense desire to “win”. But too many? And the company might turn into the growth at all costs disaster that was Uber in 2016.

I’ve actually talked to people that were at Uber during this time period. Any many of them maintain that they still love Travis Kalanick (TK) and would work him again. Why? I’d like to believe they love him in spite of being a sexist asshole [I am generally not a fan of using these type of words to criticize people but i think they apply here] rather than because of it.

TK, and many of these crazy airline executives clearly have a lot of flaws. But they also *really* wanted to win. And I think there is a part of that passion that we can learn from.


My first manager at Thumbtack once said that changing companies in Silicon Valley is almost like changing teams. In a weird way this seems true. The valley is small. There is a lot of luck. But I think the best people tend to eventually succeed even with bad luck.


How to Crush it on Twitter: David Perell and Matthew Kobach Workshop

I don’t use twitter a lot right now. I am very skeptical of a lot of claims that David makes here. That said - there is no denying that he has gotten an incredible amount of value out of twitter and built a pretty incredible career / life at a young age.

I enjoyed this a lot and if you use twitter I think you will too.

Watch / Listen here.


My Update

Thanks for reading,

Tay