I recently listened to @harrystebbings 20min VC interview with @stewart. One of the topics they covered was Stewart’s approach to company and product building. I thought the mental models he shared were simple and immediately useful. Here’s a thread of the best ones:

1. Starting meetings with bad news.

Stewart starts his board meetings with what’s *not* going well. This isn’t the norm for most business meetings, but he says listing the problems first is an expression of optimism, because he feels like they can do something about them.

He references how Berkshire Hathaway had a sign on the wall in their office that said: "Tell us the bad news first, it is only the good news that can wait".

He thinks it’s important to avoid “Persian messenger syndrome”, where people are afraid to bring their problems.

2. Believing in inevitability.

"Make it inevitable" was a saying in the early days at Slack. They believed everyone in the world would eventually use a channel-based messaging platform for internal comms instead of email.

And if they believed that, they had to make it so by helping people understand it’s true and act as if it is.

He says the Henry Ford quote “Whether you think you can, or you think you can't – you're right.” is very true. While believing that you can doesn’t mean you can, *not* believing that you can makes it pretty much certain that it’s not gonna happen.

3. Less “fail fast, and more “just decide”.

This is my favorite concept he shared. He thinks “fail fast” confuses people, and the simpler version is “just decide, and when you’re wrong, change things.”

He says he might be wrong 70% of the time on product decisions, but he just does a lot of them, and so ends up way further ahead than if he had just thought about it for a long time.

He gives a tangible example: the biggest waste of time in product organizations is meetings where people look at & give their opinion on slide decks of UI mockups, trying to decide if it will work or not.

Then he uses a great cooking analogy : It’s like putting a recipe up on the wall and asking people what they think of the recipe. How will you know unless you make it? People seem to believe they’re smart enough to tell if something’s good just by looking at the recipe.

He thinks instead you should argue about it until you need actual evidence, then you just build it and you use it, and you can tell. Like cooking, you start making something then you constantly make adjustments: temperature, thickness, salt, etc.

He gives another analogy with writing: when you sit down to write, you write the first sentence. Then the second. Then the third. Then you realize the first is pretty terrible, so you fix it. Then you write paragraphs, then consolidate 2 of them, etc.

When you’re writing and editing, each time you change your mind you don't think you’ve made some big mistake or that you’re an idiot. But in business decision making people do feel that way, so they’re slow to make decisions and feel bad when they don’t work out.

Instead, he thinks you should do the opposite: Just do it as quickly as you can and adjust as you go. You end up with a better result and learn a lot more.

4. Making 1-way door decisions.

Slack subscribes to the Amazon “1-way door vs 2-way doors” idea, and quickly decides when it's a 2-way door decision. But Stewart tries to move fast even for 1-way doors. He looks for 1 reason that trumps all of the others and hangs on to that.

Distinct from the process of making a list of pros and cons, there tends to be 1 reason that is fundamental.

5. Being an entrepreneur is like parkour.

You *have* to keep moving, you have to keep the momentum. Like parkour, it’s very opportunistic.

You're continually looking around the environment for what can give you the most advantage or leverage and pursuing it at top speed, and then going for the next thing. Hesitation, stalling, or indecision can cause a lot of damage.

6. The best solutions might not be backed by data.

Data driven decision making has corrupted Silicon Valley. People don’t realize how rigorous you need to be to have scientific certainty about something. They think a little bit of AB testing will give them the result.

The problem is you get constrained to the tiny subset of things that are provably better in a finite amount of time. Proving something in a finite amount of time can be very hard. So you see a real incrementalism.

7. Anything hugely successful comes from intuition & taste.

Stewart talks about how there are chefs, fashion designers, movie directors, and novelists that are consistently better than their peers due to their taste.

In business/product/strategy, we’ve come to this weird position that nobody could ever possibly rely on their experience and intuition to make a decision, it has to be something that is tested. He thinks anything hugely successful has come from experience and intuition.