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CREATING
AUTHENTIC
CONNECTION.

Making friends the old-fashioned way.

A quarterly meetup designed to entice curiosity,
promote listening and spark some side-ventures over a beverage (or two).


Side Venture Social Hour is a quarterly, invitation-only networking event in Portland, Maine—but it’s not your typical mixer. We bring together curious, generous, and creative professionals who value genuine connection over transactions. Whether you’re an entrepreneur, investor, or simply someone who loves meaningful conversation, this is a place to meet new friends, share ideas, and spark side ventures that last.

Guests gathered at Side Venture Social Hour in Portland Maine

The Invitation

Maine is small, but it’s easy to stay too much in our own lanes. The Side Venture Social quietly disrupts that, drawing a wide mix of people you might never otherwise meet.

Come ready to listen, trade stories, and build relationships that outlast a single evening.
Bring your curiosity. Leave with new friends, and (maybe) the spark needed to ignite your next side venture.

It’s not about just doing a deal.
It’s about finding friends for the longer journey.


Request to Join

“It’s like what a neighborhood pub would be. New people become familiar, and the good conversations come easy.” -Attendee

No name tags. No speed-dating. No sales pitches.

We meet for a drink, a laugh, and sometimes a a bar-side chat with a local professional. We focus on curiosity as a means to meeting generous, adventurous people who enjoy building things together over time.

Authentic networking event Portland Maine”

Who You’ll meet

No one comes from any specific industry or echelon.
You will meet entrepreneurs, founders, investors, managers, creatives, local professionals, and couples who are new to town.

The common threads are:

  • Genuine curiosity

  • A relational attitude & mindset

  • Generosity & reciprocity

  • A desire to build and enrich community life and work

*Please note that we take these values/threads seriously, anyone who does disregards the intention of the time will be asked to leave and will be blocked from further attendance.

Conduct Policy

The Event Details

WHEN: Every quarter from 4-6pm (ish)

WHERE: A bar, restaurant or brewery near or in Portland, Maine

HOW: Simply sign up using one of the many buttons on this page to request to join.

Local entrepreneurs and professionals connecting in Portland Maine

We believe good ideas begin with good people

If you’re hungry for conversation that lingers past introductions and you are wanting to build community here in Maine. Request an invitation to the next
Side Venture Social Hour.

Come curious.
Leave connected.

Join Us