With nine portfolio companies (and one fund), I’ve got about 15 founders that I’ve invested in. And while a few of them know each other already, most don’t. It strikes me as odd how little founders are connected through their investors (and by extension, how little the investors in a company are connected, particularly at the early stages).

For awhile I’ve been thinking about how to connect the founders in my portfolio companies. I think there’d be value there, to share ideas, brainstorm, network, or even just commiserate around the challenges of running startups. You could extend the network further to employees, but there’s something about having a small, close knit group of founders that’s compelling.

500 Startups has a pretty solid network going (it helps to have invested in so many companies!) using Dashboard.io. There are questions posted daily to the forums, and lots of mentor sessions that are scheduled through the platform. And VCs will do yearly meetings with their CEOs, or more, and some go a lot further by having regular workshops for founders (and employees). Google Ventures does a ton of this.

But I haven’t heard of angel investors creating similar networks.

It might be too hard. Building strong communities isn’t easy. Perhaps founders already have the support groups they need, or maybe most angels don’t have big enough portfolios to build up critical mass and engagement. But it feels like something that’s worth trying.

Privacy might also be an issue. Not necessarily amongst founders, but between founders and investors. Are founders really comfortable asking for help, exposing their frustrations, and sharing transparently with their investors? To some degree, of course, but I’m not sure founders look at investors as the first shoulder they go to. I understand that completely–I never wanted to expose all the challenges I was having to my investors (many of which were deeply personal) when running Standout Jobs. Sure we spent a lot of time “on the same side of the table”, but investors are also “on the other side of the table” too, whether you like it or not. I was once told, “A VCs job is to fire the CEO.” So transparency and full honesty aren’t easy. I’d like to think that the founders I’ve invested in would feel comfortable coming to me with anything, but I’m not sure they are.

A couple days ago, I posted Sendwithus (one of my portfolio companies) on Product Hunt. They got a ton of votes, and hopefully a bunch of quality leads + feedback. Then Brian Curliss, founder of MailLift (another portfolio company) reached out and asked me for an introduction. He was particularly interested in what Matt Harris, co-founder of Sendwithus, had said about partnerships and user acquisition. I only recently invested in MailLift, but part of me feels like these guys should have already known each other and had the opportunity to connect.

I’m going to reach out to the founders I’ve invested in and ask them if they’d like to do something. We’ll see what they say. But I’m also very curious about what other investors–particularly angels–have done or tried in terms of connecting their portfolio companies.