While I’m 100% happy to pick-up the tab for a happy hour I’m organizing (way less expensive than hosting at my place with prep, clean-up logistics), I’ve found a cash bar can make people feel more comfortable in attending, and bringing friends.

In 2024, I’m trying to organize more 1-1s (coffee/tea/meals/drinks) and happy hours with friends near where I live and where I travel.

My new experiment is a “Double Happy Hour” in the following format to optimize for throughput (I explain each bullet below):

• Plan two events on different dates
• Cash bar with counter
• Invite friends with shared interests
• Yes/Maybe/Next Time/Unsubscribe
• One-line bios

Okay, but why like this specifically?

Plan two events on different dates

Holding a “double happy hour” and inviting people to two different events on two different dates has a lot of benefits a) efficiency for guests: More dates makes it easier to say Yes/Maybe, and provides more flexibility, b) efficiency for organizer: It reduces event logistics effort by about half, including guests requesting alternate dates, c) higher quality event: Less effort on logistics, means more organizer bandwidth for a high quality get-together.

Cash bar with counter

Nicer cafeteria-style restaurants near corporate campuses with ample parking seem ideal for this, as they cater to lunch time rushes and have decent food, wine and beer and large spaces, and lots of lounging areas.

Also, I try to avoid bar and table service, so people don’t get trapped waiting for a check and going through the logistics of splitting bills over Venmo.

Invite friends with shared interests

Locally in Palo Alto, my friend groups are going to be graduate school alum and classmates in the area, other YC co-founders, and various tech people I’ve met through work, and I’ll share that profile when I invite folks.

When I travel, I’ll try to find groups of friends with common interests or affiliations to bring together as well, like Microsoft alum when I’m in Seattle/Redmond, and undergrad alum when I’m in Toronto area.

Yes/Maybe/Next Time/Unsubscribe

I find people feel awkward with a straight “No” in RSVPs, so to make it easier for everyone I ask RSVP for:

• Yes – Plan to attend, though plans might change.
• Maybe – Might attend, would like to stay updated.
• Next Time – Not attending this time, would like to stay updated on future events.
• Unsubscribe – No longer in the area, no need for further updates.

One-line bios

Since I know everyone at the event, not everyone knows each other, I try to share our “one-line bios” of the Yes and Maybe attendees as the event draws closer.

The early part of the Happy Hour tends to be at a small table, growing to a larger table and every new arrival is doing mini-intros with everyone else, before breaking into little social groups.

Beyond the early group it’s hard for me to introduce everyone joining, so having bios ahead of time gives people a glimpse of who’ll be there, and who might be interesting to meet–or even car pool with if people know each other.

So that’s what I’m trying out for 2024, and I’ll try to iterate as I go. In graduate school I did a Myers-Briggs assessment and scored as an “extreme extrovert” so these larger gatherings are fun an interesting for me to organize, and I’m trying to figure out how to do it more regularly and efficiently. I’ll to post as my approach evolves.

If we know each other and you’re interested in attending something like this in Palo Alto, New York, D.C., LA, Austin, Chicago, Geneva, or Amsterdam, please let me know via LinkedIn/X/Twitter DM, or email.