Two Bets for 2023.

At the start of the year, I made two small bets with Inbox Collective.

The first was on Dine & Deliver, this dinner series I’m co-hosting with the team at Who Sponsors Stuff. The bet here was simple: Could we start to bring small communities together, in person, in cities all around the world, to talk about newsletters?

The second was on the Inbox Collective website. Could we start to build an audience, on the web, to read great stories and guides about email?

Neither of these are short-term investments. I think Dine & Deliver has the potential to grow into a much bigger series of events in 2024 and beyond; I’ve already seen the web traffic to double in 2023, and I think we can double again by the end of the year. There’s so much room for growth here — and like with Dine & Deliver, growth should unlock opportunities for revenue: Sponsorship, affiliate revenue, and consulting work.

I don’t expect an immediate return on either of these bets. My goal for 2023 was to break even on both, and I will.

In 2024, I might be able to bet even bigger on the future of the business.


That’s a photo of me leading the discussion at a Dine & Deliver dinner in Washington, D.C., earlier this year.