In 2005, Circa CEO and serial entrepreneur Matt Galligan lived in Williamsville, Illinois, a small town where he was on the outside of any entrepreneurial community. He spent his downtime creating music podcasts which helped him plug into a community of podcasters that shared tips and tricks with each other while promoting each other’s shows. One of these podcasters happened to be Derrick Oien, the COO of MP3.com. Oien found Galligan’s ideas interesting and encouraged Galligan to try a startup.

“I was a kid who grew up in a town of 1,000 people and cornfields, the idea that you could even do this didn’t even begin to cross my mind,” he said. 

Since then, the small town kid with no connections to speak of has sold two companies and is now working on his third. We asked him how he created his community from scratch, and what it's like to now be on the other side of the table.

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You started in rural Illinois and now have a few companies under your belt. How can people replicate your path?

You need to find a group of people that are like-minded individuals that you can talk to and really jump into that community. The other option is if you flat-out do not have access — let’s say you’re somebody that wants to be an entrepreneur and you’re in rural North Dakota — look for the nearest conference. Even one afternoon at a conference is valuable, just buy the plane ticket. Then you start to expand that community and learn.

But the golden rule at all times is that you never try to get to a final conclusion in the very first interaction. If your goal is a career, and your goal is developing a network, you need to understand that it’s exactly like dating. Your goal at the end of the day should be to get another date, not just hook up.

How important are conferences when building a community?

A conference is a temporary community, and a lot of times you’re not going to get the most amount of value on day one. It’s rare that you’re going to start to establish a really fantastic network with a short conference, unless it lasts several days. One of the things that was incredibly valuable for me early on: In Boulder, we have the Boulder/Denver Tech Meetup. There I saw the same people over, and over again throughout the life of that community. Some people entered, and some exited, but finding that community was super important for me. I met a lot of my circle though that. 

What’s the best approach to connecting with speakers at conferences?

You might have two minutes to talk that person, so respect their time. When that person has a lot of people lined up: tap them on the shoulder as you walk past, and say, “My name is Matt, I’d really like to talk to you about my thing at some point in time, I know you’re busy right now and I want to respect your time. Here’s my card, would it be okay if I got yours?” A lot of times you’re not going to get that card in return. But you do your best to stay in touch with that person.

And then?

Email them. But ambiguity in emails is always your enemy. You’re never going to get anywhere if you say, “What do you think about this?” Which is 90 percent of the cold emails I receive. The reality is: I don’t have the time to dig in on things and noodling around, and discover for myself what this thing is about, and figure out what they’re asking.

I often tell people that cold email me to give me three questions. When you ask pointed questions, you can get real answers. It is so much easier for me to knock out an email with a thoughtful response when a question is asked.

I like the analogy of dating. What exactly do you do to during that first meeting to convey your passion and not be annoying about it?

Put yourself in the other person’s shoes. You can double down on the dating metaphor: If you go into a first date and all you can do is talk about yourself, then that’s a turnoff. If all I hear is somebody just talking at me, as opposed to somebody talking with me, then I don’t want to be interacting with that person.

Let’s say I’m at a one-day conference, I meet two or three interesting people, but I’m from out of town. How do you maintain that positive interaction after you’ve left town?

Twitter is a great resource because it is a one-way thing. If it’s mutual, then great; if it’s not, it’s still okay and you’re still getting value out of it. If I meet someone like Brad Feld, who’s an amazing individual and does great things for people that simply want to have a chat with him, but doesn’t have a lot of time — if I meet somebody like that and want to stay in touch with them, the best thing I can do is follow him on Twitter. I’m able to get a sense of what he’s thinking these days, what he’s interested in, and what links he’s sharing.

Then, the next time I see him, I can say, “Hey, that link that you shared was talking about Bitcoin, I thought it was really interesting.” A spark can happen then, and you meet on a different context. I didn’t need to be in the same place as him to discover that about him.

Matt Galligan during his SimpleGeo days | Photo: by magerleagues on Flickr

Any other advice for reaching out to busy people?

Recognize somebody’s level in the industry. You’re not going to get away with randomly trying to get in touch with Twitter co-founder Jack Dorsey these days. For example, if you’re trying to get a deal done with Uber, your best vector is probably not going to be to go to CEO Travis Kalanick. Even if you did, it’s going to get delegated to another member of his team. 

It’s always possible to ask for an intro to someone. I often don’t know anybody that’s actually doing the on-the-ground work so I’ll reach out to that CEO or that founder and say, “Hey, we’re thinking about doing this - would you mind putting me in touch with one of your salespeople or one of your biz dev people?” Take that awkwardness off the table and suggest an easy action to get the email out of their inbox.

Have you ever denied someone who asked you for an intro?

When I go back to instances where I’ve said, “No,” the vast majority of them are cold-emailing me asking for a warm introduction. The value my connections is partially based upon my reputation inside of that community. If I become the guy who always sends intros, then my value inside of that community goes down. They may stop listening to me, and when I need a real intro, that value is no longer there.

Other times it’s when somebody that I know is asking for an intro, but I just know they’re not ready. They’re saying, “Hey, can I talk to such-and-such,” and I say, “Look, you’re definitely not of the stage that I think you need to be to be talking to this person. Here’s what you need: Give me three sentences why it’s relevant, give me your bio, give me your slides,” and then what I typically do then is I will forward the information on to that individual.

I’ll email the person and write, “Hey, this person is requesting an intro.” I'll either say "I don’t know the person really well," or "I don’t personally vet this product," or "I haven’t spent time with this product," but I email that stuff out to that person and then let them decide. 

I actually had this happen recently the other day, where somebody was asking me for an intro to a CEO I knew. This person wanted to talk to the CEO because of a job position that had opened up. I said to the emailer, “Look, I’m not 100 person tight with that individual, I know them, we know each other, I’m also not super-tight with you, but what I’ll do is forward my information on to them, and if they want the intro then I’ll let you know.” Sure enough, a day later they got back to me and said, “Actually, this is great. We are looking for a person for that role. I’m hooking you in with such-and-such on my team, and I’d be happy for the intro.” Everybody won.