How the newsletter started and why it was a well-kept secret for years.

Tying the newsletter to the core business without making it salesy or deadly dull—and positioning it differently than anyone else in the space.

How he sets the flow of the newsletter—and his fear that eventually he’ll run out of stories (sound familiar?).

His #1 rule before releasing any “What We’re Seeing” emails.

Why typical business assumptions about corporate titans are wrong—and how to engage them.

Quotables

“I wanted it to be the kind of thing they would want to read while drinking their coffee in the morning or laying next to their spouse in bed, on their phone. That's the vibe I was going for.”—JD

“I was quite apprehensive initially about even doing something weekly. Cause I was like I once you're on the ride, it’s hard to get off.”—JD

“It's gotten harder because I've used up most of my good stories by now, like funny stories I have from my dad or my college or whatever and like all my best material, I worry sometimes that I've used it up.”—JD

“An insight is significantly more valuable the more relatable you can make it.”—JD

“When you can make the insight…it doesn't just allow us to connect with that person as a reader, but it allows them to actually use that insight to drive a decision that they have to make.”—JD

“I do think there are the people who read that and they see I'm not exactly sure what this company does, but I want to do business with people like this.”—JD

“My Saturday email gets to be a little bit of a sacred place where that (sales) stuff doesn't happen.”—JD

“I can tell you without ever naming any names, the most senior people and powerful people on that list are the ones who are most likely to answer those frivolous poll questions at the end of the newsletter.”—JD

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