Fifth Star Funds
Apply Give
Home · Portfolio · Approachable
BuildingConsumerBacked 2023

Approachable

Founded by Matthew Williams

Plans a real-world outing and puts you in a small group of five to ten compatible strangers to go with, so nobody has to show up alone.

Where they are now

The app is live in Chicago.

It runs group outings and ticketed events. Updated September 2026.

What they do

Moving to a new city or a new job leaves people with nobody to do anything with. Approachable builds the group and plans the event, so a member's only job is to turn up. Members can host their own hangout too.

Who it's for

Adults in Chicago who want to make friends. Concerts, hikes, dinners, pickleball, museums and run clubs.

What's different

The matching. A personality algorithm assembles the group rather than leaving it to whoever happens to reply.


What they've done, with sources
Back a founder

Every Fifth Star company gets the same $25,000 check.

Contributions go into the fund that writes them. If Approachable exits one day, our share comes back to the fund and goes out again, which is what makes us an evergreen fund.

More from the portfolio

Stay in touch

Updates on the founders we back and the work behind the checks.