#33 — CEO to SDR

Apparently, it’s SDR Appreciation Week.

I thought this would be a good time to look back on the very weird experiment I did three years ago to become an “interim SDR.”

It was a grind. But it was one of the most useful learning exercises that I’ve done.

Why was it so fruitful? Here’s my take:

  1. It was an extreme version. You’ve seen “day in the life.” This was 60 days. Lots of pain to endure, but that unlocked some deeper and unexpected learning.

  2. It was uncomfortably public. I leaned into the high risk of embarrassment. I shared failures and asked dumb questions. Some haters trolled me for it. But the public nature of the project brought a lot of inbound help and new relationships. Smart people wanted to help. This accelerated the learning process and led to many lasting connections.

  3. There was no clear goal, but many possible upsides. I figured that I would have many benefits from the exercise, but I didn’t know which ones. So I didn’t try to predict or forecast any outcomes. Instead, I just assumed something good would come out the other side and went for it. I think this is a form of optionality.

Have you seen other similar experiments? I’d love to find more.

p.s. I think there’s a loose segue into this week’s podcast with Howard Behar on servant leadership. He spent A TON of time on the frontlines…

Built in Seattle Podcast


Howard Behar (former Starbucks President of North America) talks about growing Starbucks from startup to icon over 21 years, developing values, and servant leadership.

On finding conviction without proof:

“It wasn't so much that I thought they were onto something from a business perspective. It's that the people were so energized and so excited. […] The people were positive and it kinda had a soul to it.”

On servant leadership:

“you don't walk in a store and see a piece of paper on the floor and walk by it. You pick up the piece of paper. I don't care what your position is. You could be, God should be picking up the pieces of paper.”