Connecting with investors or executives isn't easy, but is an essential responsibility for anyone in the startup world, especially as the CEO.

Here's the trouble: Every investor out there literally has an email inbox full of "requests to connect" messages. In growing Draft, a real money fantasy sports app, I wasn't interested in being another unread piece of clutter.

Twitter has led to some of my best connections. 

This isn't some "magical strategy" or insider tip. Instead, it's three true stories of how I met some of the biggest names in the startup world, and most importantly, created a connection that led to the $3.5 million we just raised for Draft.

one-icon Dave McClure, Founding Partner at 500 Startups. 

Back in 2009 I happened to check my stream and notice that Dave McClure was going to be in Boston the following morning. I knew he was planning to drop by our office while we were at TechStars, but I wanted to make sure I got some one-on-one time with him. I reached out to give him a ride from the airport - that way, I'd not only be helpful, but only be requesting to occupy commuting time he already had in his schedule:

Sure enough, it worked. I picked him up and was able to spend what turned into a good thirty minutes (yes, I got him just a little lost) chatting with one of the most well known early stage investors. While captive, he tweeted about our time together:

 Outcome: Not only did I get to connect with Dave, but the tweets also resulted in a story in the Boston Globe that earned us some great early press.

two-icon Travis Kalanick, CEO of Uber.

Back in 2010, Travis tweeted about being in Boston for the weekend. I immediately responded: 

Although I didn't get an immediate response, he tweeted back the next day to see if I could meet within the hour:

Naturally, I dropped what I was doing and went to meet him.

 Outcome: Travis and I ended up walking around downtown Boston for almost two hours. Not a bad person to get to know.

three-icon Greg Bettinelli, Partner at UpFront Ventures

Just around the start of last football season, I noticed an investor I’ve always had a lot of respect for, Greg Bettinelli tweeting about my industry.

We then went back and forth for a bit as I helped answer some questions and offered to walk him through the market. This could easily be discussed further, so I let him know I'd be open to a longer conversation:

We hopped on a call the next morning. And ...

 Outcome: Three months later, Greg ended up leading our Series A through Upfront Ventures. 

People always ask me why I find Twitter so valuable: Not only is it the ability to learn from and follow super smart and insightful people, but it’s a great platform to connect with these people - both online and in the real world.

It's really as simple, and as effective as it sounds.

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Originally published Apr 16, 2015 2:32:00 PM, updated February 01 2017

Topics:

Social Selling