On Lanyrd, investing, and selling
Lanyrd blew me away from the day it launched. It's a way to track speakers and attendees of upcoming conferences, but it's also a social web application. It was the first site/app I used that didn't require yet another login (it used the then-new Twitter auth). It was the first Twitter-powered app that was instantly useful the moment I connected my accounts. Being a tech nerd that speaks/goes to conferences and follows lots of other tech nerds that speak at/attend conferences, my first post-login screen at Lanyrd was filled with information about dozens of conferences my friends were speaking at & attending that I otherwise wouldn't have known about.
Frankly, I was amazed. I went from hitting the homepage of a new app I'd never heard of to having screens full of useful information about my friends and the industry I work in, in about 30 seconds. I immediately dashed off a message to Simon Willison (one of the co-founders) saying Lanyrd was really impressive and if they ever opened up a round of funding to keep me in mind. Simon and Nat got back to me soon after and there were lots of Skype calls and documents sent to lawyers and in the end I got to become the very first investor in Simon and Nat while also being an early advisor to Lanyrd.
Recently they sent out an email announcing an acquisition by Eventbrite and I was surprised to get the news out of the blue but also happy to hear who was doing the acquiring. If you haven't used it lately, Eventbrite is a great site for arranging/selling/buying tickets for events. As Eventbrite has grown over the last few years, I've realized it plays a larger role in my life. In the beginning, it was just a small events site, like a more formal version of Evite and I would attend local industry events for maybe 20 people. Lately, I've used it to pay for $1,000+ conference tickets, woke up early to get tickets for high demand small events that sell out within minutes, while still using it for beer bar meetups for a couple dozen friends. I find the biggest problem with Eventbrite these days is discovery; that unless I happened to catch a single tweet from a friend at 11pm one night announcing an event, I wouldn't know that event existed.
Usually startup acquisitions are bumpy affairs, where a new owner tacks on a new vision for a product, morphs it into their existing infrastructure and inevitably shuts the old site down. I was happy to hear about an Eventbrite/Lanyrd deal because it'll be a great addition to both properties. My Lanyrd page will extend from technology conferences to every local event on Eventbrite that friends are throwing and attending. The ginormous list of local events offered to me at Eventbrite will filter into things my friends are organizing and/or attending, through my Lanyrd-powered friends. It's going to be win-win for both companies.
On Investing
Over the last few years, I've put some energy, effort, and money into companies I like and want to see do good in the world. To date, I've invested in four things: Kickstarter, Lanyrd, Little Bird, and Original. Mostly, I'm investing in friends, people I've known for a while that I believe in and have good ideas that can become big. Part of this also comes from working in the Bay Area during the 2000-era tech boom, and watching my friends build amazing things in the aftermath of the bust. I remember seeing the first Flickr shoebox/chat app and asking Stewart if I could invest a couple thousand bucks I had in savings because I thought this could revolutionize the photography world. There were complicating issues at the time (they'd already taken larger rounds of funding) but I told myself if I ever got a chance to see a new app really early on that I felt had greatness and a great team behind it, I'd do whatever I could to help it along.
So far, it's been a real waiting game. You see demos from friends, you talk over small friends & family style funding, you exchange lots of paperwork with lawyers, and eventually you help the founders meet other people for larger funding rounds while you often get to help steer the product as an early user/advisor. In four years of investing, this is the first acquisition I've been through, so I can see why VC firms place lots of bets on lots of companies, since they probably like to see more action than one sale every four years.
On Selling
I've neglected to mention it on my blog or Twitter until now, but last Fall, Paul and I sold Fuelly.com to a guy named Andy that runs a bunch of car sites. He had been following us for years, had run similar sites, and had a much larger community of car enthusiasts that could really push Fuelly to new heights. We quietly announced it on Fuelly recently and Andy has the time/energy (that we didn't) to tackle loads of new features for the site. They recently bought and integrated a popular iPhone app for Fuelly and the upcoming APIs will accomplish a lot of the ideas we hoped to get to someday.
Not all acquisitions end with horror stories from "our incredible journey", sometimes a person or company comes along that is doing something similar to what you're doing and offers to take over and build up all the things you dreamed about, without losing the original purpose for the site and service. I think that's the case for both Lanyrd and Fuelly today.