If you want to be remembered by a client, don't take them to a steakhouse. Take them somewhere they'll talk about the next time you're in a room together. The point of client entertainment isn't the meal. It's the conversation you get while it's happening, and the story your client tells afterward. A table for two hours gives you neither.
I'm Jonathan Porter. I run Chicago Pizza Tours, and I host a fair number of client outings, the kind where the goal is a relationship, not a headcount. Here's how I'd think about it.
Why the steakhouse dinner keeps losing
The default move is a nice dinner, and it's the default for a reason. It's safe, it's easy to book, and nobody gets fired for it. But it has two quiet problems. You're pinned across a table, so the conversation only goes as far as the person directly in front of you. And it's completely forgettable, because your client has been taken to a nice dinner a hundred times.
Being forgettable is the real risk. You flew someone in, or you're trying to win them, and the best you did was a meal they can't distinguish from every other meal.
What actually lands with a client
The events clients remember tend to share three things:
- Shared motion. Walking somewhere together loosens people up in a way a fixed table never does. The real talk happens between stops.
- A local's version of the city. Anyone can book a chain restaurant. Taking a client to real neighborhoods and a genuine local experience signals effort and taste.
- A story to retell. "They took us on a pizza tour and we ended up at this spot in Wicker Park" is a story. "We had dinner" is not.
That's the honest case for a private pizza tour as client entertainment. You get hours of natural conversation while you walk and eat, your guest sees a side of Chicago they wouldn't find alone, and they leave with a story that has your name attached to it.
The practical part
For a client event, the logistics need to disappear so you can focus on the guest. So plainly: private outings work for small high-value groups, not just big teams, food and dietary needs are handled in advance, and you get one clean invoice for the whole thing, which makes it painless to expense. And yes, the tour has been featured on Wheel of Fortune and the Travel Channel, which is a nice thing for your guest to mention when they get home.
Be the one they remember
If you've got a client or a recruit coming to town, reach out to plan a private outing or check available dates. Give them a reason to remember the trip, and you.
Common questions
Pick something that gives you real conversation time and a shared experience, not just a table. A private food or pizza tour lets you talk while you walk and eat, and gives your guests a Chicago memory they'll bring up the next time you meet.
A steakhouse dinner is safe, but you're locked across a table for two hours and nobody remembers it. An experience gives you more natural conversation and a story your client actually retells.
Yes. Private outings work for small, high-value groups, not just big teams. Tell me your headcount and I'll put together something that fits.
Yes. You get one clean receipt for the whole thing, including food, so it's simple to expense and simple to explain to accounting.
As soon as you know your client's dates. Private slots fill up, and the earlier we reserve, the more flexibility you have on timing and neighborhoods.
