Month: December 2019

​I don’t like annual reviews. I love the idea of them. I can reflect on my past year, the highs and lows, wins and losses, and make some plans for the next year. It sounds great. In practice, it feels daunting.

This year, I want to try something lighter. I will pose and answer just one question. Then, I can use that as a guide post for the next year. I invite you to do the same.

What’s one practice or principal that has served me well in 2019, and how can I double down on it in 2020?

Simplicity.

When things start getting nuanced or complicated, try to reel it back in to a single core idea. What’s the main thing? How can I state it in a way that anyone can understand? Keep it simple.

I simultaneously think $40k for a great deck is a steal, and that if you need someone else to make it for you then you’re probably screwed.

The key insight is that pitching a company, or anything really, is primarily a challenge of storytelling. Once I fully understood this, after months of banging my head against a wall, it was like a lightbulb coming on. Yes, making your pitch coherent and look aesthetically appealing can be very helpful. However, what really persuades people is a good story. If you can get the audience excited about what you’re doing, they’ll start to see through your eyes and the hard work is done. From my limited experience, only one of the creators of the Shiny New Thing (company, product, movement, etc.) can figure out the right way to tell that story. 

Venkat had a cool Twitter game where he challenged people to generate 100 tweet-opinions on a topic of his choice. Mine was Rich People.

This was fun, and less challenging than I expected. It seems like we are more capable than we think at generating opinions on arbitrary topics. Once I got through the surface level stuff, I surprised myself at some of the ideas I came up with. Most bad, some interesting.

The whole exercise gave me a newfound appreciation for the value of constraints. 

P.S. This is my first attempt at another experiment. I’m jealous of everyone’s newsletters, but I don’t expect that I’ll be able to write more than a paragraph or two every week.

So that’s what I’m doing: Weekly 140 words or less. Very lightly edited. Enjoy