In building our Vermont Angel List, we've made a deliberate choice that might seem counterintuitive at first: all initial meetings between founders and angels are explicitly for advice, not funding pitches.
This isn't just a nice idea—it's a strategic choice that addresses real challenges in the angel investment ecosystem, particularly in our tight-knit Vermont community.
The Angel Investor's Dilemma
Angel investors face a constant challenge: they want to discover promising opportunities, but they don't want to be bombarded with funding requests. Many successful angels in Vermont deliberately maintain low profiles to avoid a deluge of pitches landing in their inboxes.
When angels receive direct investment requests from founders they don't know, they're put in an uncomfortable position. They either have to say "no" (which no one enjoys) or spend significant time evaluating an opportunity that often isn't a good fit.
Breaking Down the Walled Garden
The traditional approach to angel investing creates a "walled garden" where opportunities flow through established networks. If you're a founder without these connections, you're left outside looking in.
By structuring initial meetings explicitly for advice, we remove the immediate pressure that causes many angels to decline meetings with founders outside their networks. It creates a safe entry point where knowledge can be shared without the immediate expectation of a funding decision.
Why This Approach Works
For angels, advice meetings offer several benefits:
They can maintain privacy while still connecting with new founders
They can evaluate founders based on their receptiveness to feedback
They can share expertise without the pressure of immediate investment decisions
They can easily refer founders to other angels if the opportunity isn't right for them
For founders, the benefits are equally powerful:
Access to expertise and network connections otherwise unavailable
Opportunity to demonstrate coachability and execution ability
Building relationships based on value exchange rather than just asking for money
Receiving honest feedback without the pressure of a "pitch performance"
Building Vermont's Connector Culture
This advice-first approach is particularly well-suited to Vermont's values. By creating a culture where angels willingly connect with founders outside their immediate networks—even when the opportunity isn't right for them personally—we build a stronger ecosystem for everyone.
The best investor-founder relationships start with genuine connection and mutual respect. By taking investment pressure off the table initially, we allow those authentic relationships to develop naturally.
And that's how great investments really happen.