October 30, 2026

The Damn Dinner

Last night, I attended a fancy dinner hosted by recent podcast guest and author of The Damn Rules, Nick Richtsmeier.

The premise of the gathering was...

An exclusive night of dinner and discussion on the implications of The Damn Rules in your business and your community, with me and some other cool people.

It was a fascinating evening. As expected, the discussion was thought-provoking, insightful, and even a bit inspirational.

Perhaps less expected but no less fascinating was my experience of meeting strangers in person to discuss big ideas.

For those who, like me, haven’t done such a thing in (checks notes) over a decade, I’ll try to describe it in terms that us remote workers can relate to:

It was sort of like a Zoom meeting, but around a physical table in a real room with people bringing us food and drinks.

Can you imagine?

The noise? The germs? The awkward social interactions?

Barbaric! ;-)

But seriously...

For context, I’ve been working 100% remotely for twenty years. I haven’t been to a dinner with total strangers siiiince... I can’t even remember when. Probably a speaker dinner at a conference in the mid-2010s?

That’s enough time to forget just how different a small, in-person event actually is from its digital counterparts.

You REALLY get to know and connect with the other folks there.

By way of comparison...

It just so happens that today I did a fireside chat in Zoom for a private community. No slides, just discussion and Q&A. There were about 15 people in attendance. The only one I knew was the host.

On the surface, the Zoom meeting had a lot in common with the “Damn Dinner”:

Both featured a lively conversation and free exchange of ideas.
They were both fairly small groups.
In each case, I only knew the host.
I enjoyed both, and it seemed like others did, too.

But wow! The difference was night and day in terms of connection (and therefore, trust).

For example:

I remember everyone’s name from the dinner. I don’t remember anyone’s name from the Zoom.
If I ran into them on the street, I would recognize everyone from the dinner and no one from the Zoom.
I trust everyone from the dinner in their area of expertise. I don’t even know anyone’s area of expertise from the Zoom call.

These differences are HUGE if you believe that positioning, relationships, and trust are good for business.

I think it’s important to note that this has NOTHING to do with the people in either scenario and EVERYTHING to do with the inherent limitations of virtual gatherings.

Am I saying all virtual gatherings are bad or useless? Absolutely not. There are pros and cons to everything.

Video calls are quick, easy, convenient, cheap, etc. And, in fact, you can build connection and trust with people remotely. It just takes waaaaaaaay longer than in person.

Here’s the thing...

If you have the opportunity to attend (or host) an in-person event with a small group of people who enjoy having a discussion, I encourage you to do it.

Especially if it’s been more than a decade since the last one.

Yours,

—J

P.S. I’ve got an IRL thing coming up in December that I’ll say more about soon, but I’d bet there are free local meetups near you.

And if there aren’t, why not host one? I give you permission to steal Nick’s description:

“An exclusive night of dinner and discussion on the implications of FILL_IN_THE_BLANK in your business and your community, with me and some other cool people.”

See? It doesn’t have to be hard. You can do it!