Landing your first “professional” investor usually doesn’t start with Twitter and a #pitchvctaxi hashtag. Of course, most investors aren’t quite as accessible, or as crazy, as Dave McClure.

At 9:15 AM on September 1st, I was pretty bummed. I was in Sunnyvale for three days, in between friends’ weddings in Seattle and San Diego. I’d only been able to secure a couple meetings, and one of those had just canceled on me. We were staying at the god-awful Sundowner Inn (3-star hotel? thanks, Hotwire), which looks like a motel where people either go to have an affair or to shoot each other, and I figured I’d just spend the morning in bed.

Then, my girlfriend noticed Dave’s tweet that said he was looking for a ride to his mechanic. Anyone who picked him up could pitch him on the way. Figuring dignity is for the unfunded, I threw on yesterday’s clothes, hopped on 101, and headed over to Buck’s to give Dave McClure a lift.

The #pitchvctaxi experience

I arrived at Buck’s, and Dave came out on the phone, while tweeting, while trying to organize his laptop bag. He looked up the address on his phone, almost dropping his laptop while still talking, and showed me the address while pointing at the GPS. I entered it and started driving, thinking that if he really thought he could spend the entire ride on the phone, I was going to drop him off a couple exits down 280. Fortunately, after about a minute, he told whoever he was talking to “Yeah, let’s do the deal, I’ll go in for $50k. Look, I’ll call you back, this guy’s giving me a ride, I have to hear his pitch” – and I started telling him about Baydin.

I described how we’d launched Boomerang for Gmail about a week and a half, and how we’d gone from 0 to 40,000 users during that time, and how much our users love it. I explained that we had paying customers for our Outlook version of Boomerang, and that we thought the Boomerang feature would be at the core of something much bigger. I described our plans to build an Email Game that would be a lot more than a toy, something that really helps people be more responsive and feel better about their email.

Dave wouldn’t be Dave if he didn’t immediately start talking about metrics. He asked what we were measuring now, and how those numbers looked. Since he’s on deal #59, he had a lot of context when he told us our active users numbers were really solid.

He took me on a deep dive about on what we plan to start measuring in the future and how we will respond in different scenarios for those measurements. Fortunately, I was prepared to have a conversation about metrics while driving, both because we’ve spent enough time thinking about it to know them cold and because my friend Jeremy Levine was the first person to have the #pitchvctaxi experience and had briefed me on what to expect.

At the end of our roughly 14-mile ride, Dave mentioned that he’d heard about a company that was doing the same thing from Katherine Barr. I told him that the company was us – we’d talked with Katherine and she had made an intro for us. He then mentioned that he’d heard something about a company like ours from Hiten Shah. That was also us, and Hiten had agreed to force-install Boomerang on Dave’s laptop. His assistant Melissa was also a Boomerang for Gmail user, and she’d mentioned us as well.

We pulled into the Toyota dealership, and roughly 40 minutes after I’d picked him up, Dave had made his decision. I’m in for 50, maybe 100. We talked terms, and Bin 38 aside, Dave was completely fine with our convertible note.

We’re thrilled to be one of the 500 Startups, and meeting a bunch of our fellow 500 Startups founders at Disrupt had a lot to do with our plans for the next year.

What’s next for Baydin?

First up, we’re moving to Silicon Valley. Between the incredible startup events out there, the incredible introductions that we got out there, the infinitely better fundraising environment, the meetings with big companies we were able to have while we were out there, and the sheer number of startups and the culture they create, the valley is irresistible to us.

We’ll miss Boston, where we got some really fantastic advice and made some great friends, but we feel like our business is a better fit in the Valley. Once we get out there, on November 19, we will begin working to close the remaining $150k of room left in our seed round with investors who have a deep understanding of the e-mail space or the social gaming space.

#pitchvctaxi by the numbers

• 14.1 miles driven
• 40 minutes
• $100k commitment
• #pitchvctaxi fare: $7092.19 per mile driven
• San Francisco average taxi fare: $2.75 per mile driven

For now, our story goes down as Dave McClure’s most expensive taxi ride. In a couple years, we hope it will turn into his most lucrative.