50th newsletter sent today

Instead of talking about the wins, let’s focus on the Ls (losses and learnings)

1/ Loss: lack of focus

Early on, the voice & user persona were undefined

I landed on “your witty friend who goes out but will be in front of a TV on Friday night watching the big game”

I named the audience “the next generation of sports fans”

Lesson: action clarifies strategy

2/ Loss: too much emphasis on quality

It’s very hard to make something great on day 1

Understanding that removes a lot of stress. Remember, Airbnb started with 2 guys on air mattresses and Morning Brew was a PDF attachment

Lesson: “consistency leads to greatness”

h/t @web

3/ Loss: lack of confidence

Imposter syndrome is real and comparison destroys confidence

You are where you are. Create a plan to move forward, recognize your insecurity, and execute

Lesson: do your best and keep going

4/ Loss: bad cold emails

I read too many “how tos” before sending my first cold emails

They were wordy, not funny, and didn’t get to the point

I’m a concise, straightforward person. Once cold emails showed that, response rates skyrocketed

Lesson: be yourself

5/ win-lose mindset

I’m a hyper competitive, win at all costs person. I grew up playing sports competitively and saw things as win-lose

It’s not always that way. There’s tons of white space on the internet

Lesson: life is a +sum game and it’s more fun viewed this way

6/ There are many other Ls that’s could be shared.

Last learning: brevity is king :)