Bram Pitoyo, Portland Creative/Tech Event Review

Portland Web Innovators – Andy Baio Talks Side Projects And Acquisitions: An Event Review

Portland Web Innovators – Andy Baio Talks Side Projects And Acquisitions

When: Wednesday, June 4, 2008, 7:00 – 9:00 PM

Where: NemoDesign, which again proved my inability to navigate around Portland by arriving early and then spending the next 20 minutes looking for the correct entrance. Lesson: company/agency/studio logo on the door should be big enough to notice from the street.

What It’s About: The elusive Andy Baio talks about three lessons that he learned from building, in order of appearance,, and

Let’s get to it.


It all started with a script that takes dictionary words and buys the .org .net and .com domain for each word. In the pool, there were three sites:, and

I want to make software that allows virtual community to meet offline—that is so crucial.

Andy learnt #1 from after its competitor, launched with much fanfare and better feature: Finish it.

Around that time, he started his own blog. His first entry was posted on April 14, 2002, wherein he established the ground rules in subsequent writing:

No journaling. No tired memes. Be original. proved to bring immeasurable impact for Andy. It raised his visibility—even in mainstream media, where 5 different journalists from The New York Times covered 5 different articles on 5 different times. also ended up being a platform for his future projects (including It connected him to likeminded people.

Through my blog, I’ve pretty much been able to meet everybody that I care about and admire.

Lesson #2 was learnt from Blog because you love it, not because you want to “develop an audience.” was started in January 2003. He did not stop until it was done 9 months later.

There were two reasons why Andy was compelled to build


I always loved live music, but always had terrible memory. For example: I would read LA Weekly and see a concert from a band I loved, then forget about it—until a week later, when my friend told me about how awesome the concert was.

Second: Friendster.

I thought it would be cool to do something with social network beyond connecting online. was a side project. He did it in spare time, by himself.

Andy then puts up different mockups of the first iteration of, wherein he said:

I love to do high-resolution mockup on every version of Upcoming. Other people “envision” something out of a wireframe. I can’t do that, that’s why I must have pixel-perfect mockups.

On the concept of “Watching” (as opposed to “Attending”): Watching is where you want your friends to know about the event, but also that you won’t be attending it. “It,” Andy said, “seemed to be a natural way of approaching it.”

Andy continued his work on until his son was born, and he had to stop all work on for 8 months.

You have a job, a side project and a son. Pick two.

Fortunately, the site continued to grow and doesn’t ‘explode’ without his continual attention.

Note: The Web 2.0 movement is starting to come about around this time.

On March 2005, Johnny Dell, a reporter from InfoWorld wrote about how awesome Upcoming is. He thought of improving it via the uses of API and Tags, two things that didn’t really “exist” at that time. Andy decided to put a gun in his head and promised to deliver the improvements in one week. To this end, he wrangled User #2 and a friend to help him do it. The new Upcoming is launched a week later.

At that time, Tim O’Reilly wrote the famed article that compares Web 1.0 and 2.0 side by side, where he mentioned that evite is 1.0, and is 2.0. That brought a lot of coverage, but more importantly, people were building applications on top of the API.

On July 2005, Andy got an email from Caterina Fake (founder of flickr.) They were tasked to “bring the cool back to Yahoo.” They looked around on the startup that they should bring to the table. They contacted Andy, and forwarded him to Yahoo!Local. Three meetings later, we were acquired on October 2005.

Upcoming grows by connections that I made through Waxy. For instance, I met Caterina through Metafilter and my blog. So it’s all about connections as much as the friendships that you made, and knowing people who do cool things that you wanted to do.

The Good Parts (of being acquired by Yahoo)

  • Surrounded by brilliant people. Upcoming was literally 3 cubicles away from flickr designers and engineers. Then there are Delicious and MyBlogLog (the same guys who started Yahoo!Pipes.)
  • This is obvious, but going from a “side project” to a “full-time job,” working on what I considered to be my baby, is awesome.
  • Platform technology that Yahoo! offered is powerful, and sometime complex, but enabled us to do things that we previously weren’t able to do (ie. geolocation open API.)

The Not So Great Parts

  • Bureaucracy is a lot to deal with when you only have 3 people. it’s inconceivable that a 5-person startup can go into Yahoo, a 14,000-strong company with legacy technology that you need to adapt to.
  • Integration was very hard to do and may drew away from things that you really cared about. For example: when the newly acquired Upcoming were working on integration with various Yahoo! services, it drives traffic to the site, but it’s not Upcoming’s organic traffic.
  • With new technologies, came a level of complexity that slowed down Upcoming’s site. When you’re acquired, you will come in with your own way of doing things, and you have to adapt.

But in the end, everyone benefits

  • The Upcoming community got a much better, stable and powerful site than it would have ever been, had I work on it alone.
  • Even Yahoo! benefits. For instance, you can click on Yahoo → Local or search for events in Portland, and it will show you inline results that direct to
  • As a startup, we did quite well and learnt a lot of information in a short period of time.

BUT I would caution any of you to not plan any acquisition exit. Talking to everybody at the Valley was like talking to a musician at Sunset Strip in the 80’s. Everyone talks about “getting million dollars in funding and entering into a hot market.”

Plus, Upcoming was never intended to really be a business. It wasn’t even a company. Just a website that was acquired. That’s it.

(We had the easiest due diligence in the world, because it was just 3 guys running service on a hosted server.)

Lesson #3 from Build for yourself. Bootstrap. Don’t grow too fast, acquire funding, etc. If you do it well, at the very least, people like you will flock. And if you built it with no certain constraint in mind, it can go anywhere.

I was trying to built something that I think was fun. I didn’t even drop my day job to do it.


Q: Is there a concern about intellectual porperties in the M&A process when Upcoming was acquired by Yahoo?
A: If you work at a tech company, like Yahoo, and you work on your own startup, that’s certainly going to be trouble. Don’t even complete with your employer. At Pixar, you have to pitch anything you came up with to your bosses first. The concept will almost always be rejected, but then you’re free to work on that.

Q: How much traffic were you guys having when you were acquired?
A: When were acquired, we doubled our server infrastructure to TWO servers.

Upcoming was a microstartup in every sense. It has a reputation that’s disproportionate for its size. Part of that is because it is used heavily in the Bay Area. Another part is because the userbase it were very active, social, “2.0” people.

You can’t expect an event site like to grow flickr-big, because the interaction model is different.

Upcoming’s biggest contribution to Yahoo: providing an event-base for everything. Some of those integration [with other services] are awesome because they just used our API and we didn’t have to do anything, besides maybe building some private methods.

Q: When did you realize that Upcoming was “a bigger deal”?
A: It happened over and over from the moment I launched it. A group of Americans in China adopted it. In a small college town outside of Michigan, 10–15 students who love music adopted it, which caused rapid local adoption. I saw “spikes” like these all the time.

Right now, if you go to the Portland website, this event is listed as #1 today. Is it really #1 [in the litera sensel of the word]? Probably not.

If you have an active core, that’s the community that”s going to decide what’s most popular.

Q: Did you guys do any marketing activity?
A: I did some talks and opened myself to press. That’s it. There was no budget for marketing Upcoming. Our advertising paid for the server but and was making a little bit of money. But for us, word of mouth is the most logical form of marketing because we wanted it to grow organically.

Q: Did Yahoo! hoped that everybody would use Upcoming? Or just the geek audience?
A: I always hoped that everybody would use it. It would’ve been great, but part of the challenge is that you have a very large audience that just wants to lurk. 95–98% percent of people who has a Yahoo!ID are just watching what’s out there. Back when we were there, Yahoo! were trying very hard to change that (read: trying to be more Yelp-like.) It’s tough, and they’re still working on making changes to get mainstream audience to dig into it, but not much had been happening ever since.

Q: Feedback from the community after Yahoo! acquisition?
A: We were very conscious of this aspect. Before we were acquired, I saw this 2 case studies:

  1. flickr: sent out announcement months in advance, saying that user will have to do it eventually (adopt a Yahoo!ID) but provide no other benefit whatsoever, only inconvenience (while it might’ve been relatively minor.)
  2. Blogger: blogger 2.0, big redesign, tons of new feature, also, you’re going to use your new Google account to login into it.

I’m a Yahoo! user and I was afraid of switching! Even if I do, what did I get out of it besides inconvenience?

So we bundled all these redesigns and feature updates all at once, then gave out free T-Shirts to old users. There was very little outcry.

Q: What community feature that was introduced after launch brought a lot of traffic?
A: One of the bigger things was that we started integrating event feed from Yahoo!Local, so every event can be populated from there and not always be added by someone.

Also, Switching from the old “Metro” system to Yahoo!’s location system (using zipcode, proper geocoding.)

Q: Tell me more about the logo?
A: The type was designed by Letterhead Font. I always had people questioning the logo: “It looked like a sports/baseball team.” But I always liked the idea of it having a “summery/outdoorsy” and organic feel. Plus: it also made for great shirts. I’m glad that Yahoo! kept the logo up there.

Q: Did you have to alter your platform/codebase after the site scaled/bought by Yahoo?
A: Yes, we had to move over to Yahoo’s platform. We had an easier time, though (ie. compared to Yahoo’s standard were PHP, but upcoming was written in PHP. Several things had to be tweaked, but the code changes—yes. Every lick of code that I wrote got rewritten, and we ended up using Yahoo! search engine to power ours.

Q: How did you left Yahoo?
A: I left not long after my contract expired (last November.) There are a couple of things going on at Yahoo that was interesting (couldn’t talk about it,) but ultimately what happened was, when you’re working for something you built for somebody else, it changes the dynamic of your work. I’ve been working on upcoming for the past 5 years, but it all came down to wanting to work for myself.


Portland is awesome, it has tremendous DIY culture that’s very different from Valley culture. Down there, if you ask somebody about the reason why they’re building something, the goal would almost always be be commercial. I’m interested in building products that are profitable, but at the same time, also makes a lot of people happy.

Ultimately, I just want to do something new and have absolute control over it, and make money doing it.


Q: How does Upcoming monitor inappropriate events?
A: Through flagging, community manager. There were two classes of frustrating behaviors that were happening not long after we were acquired:

  1. We had Nigerian spammers discover Upcoming as a backdoor, using its Private Messaging feature to get to user.
  2. People would post event just to put spammy information in it.
  3. Then we started to built heuristics into the system.

    One of the test that we did was we pass everything to Spam Assassin. I highly recommend this.

    Q: Coudal’s Deck?
    A: The Deck fits with my philosophy. It targets sites with little but influential traffic (like the kind of blogging that I do at Waxy.) No CPM model. Very focused. It’s a great model that I haven’t seen picked up by any other places.

    Q: Tell me more about the “week you brought your friends in?”
    A: So I commited publicly to Johnny Dell’s InfoWorld column that I will do what the article requested in a week, so I asked Gordon and Leonard for help. After that, it became a natural collaboration.

    Q: Where do your attention lies these days?
    A: I spent a lot of time writing, something that I wasn’t able to do during my Upcoming–Yahoo! days. But there are two areas that I’m interested in:

    1. Web-based collaborative gaming. I went to GDC and saw indie game movement. Mind expanding stuff that paralleles with what has been going on with Web 2.0.
    2. Providing ways for indie creator to make money doing what they love. Can’t really talk too much about this, though.

    I have also been working with Rael Dornfest with his Bottlecap Labs project.

    Q: How do you value Upcoming in the negotiation with Yahoo?
    A: We asked ourselves: “If we worked on it ourselves, in 2 years, what would we be making?” We had a rough number going in, though. Second thing: it’s totally risk-free for us to get acquired. There were no contractual obligation to stay for a period of time.

    Q: Have you considered going to another investor before Upcoming was acquired? Or just kept it a side project?
    A: Our plan was that we either:

    1. Are going to be acquired by Yahoo!, or
    2. Gordon and Leonard will be working on it full-time.

    There are compromises and risks that we don’t want to take, so we didn’t consider angel investing.

    Q: Would you do it differently if you had to do it all over again?
    A: While we were at Yahoo? Yeah, we would. But no, I’m really happy with the way everything came off for everyone.

    Q: Are there other offers from companies other than Yahoo?
    A: Nope. The whole process was very fast, in fact.

    Our official contract was signed and announced at the same day, in fact. I went to Web 2.0 conference, but the night before, we tried to hammer the contract out because they want to get the news out at the conference.

    Q: Can you tell me about’s general timeline?
    January 2003: start
    September 2003: launch
    January/February 2005: Gordon & Leonard comes in.

    Q: Any patent/legal stuff you had to worry about while at Yahoo?
    A: We hadn’t patented anything before we were acquired. With every new release at Yahoo, though, they were asking me for a new patent filing. I think it’s not a good concept. Hate the patent system.


    Technicality: ☝ ½
    Translation:I talked to Andy whilst enjoying a veggie pizza and humming along extremely loud Middle Eastern music at It’s A Beautiful Pizza, and he said that he was planning on making the talk as accessible to everyone as possible.

    Interestingness: ☝ ☝ ☝ ☝ ☝
    Translation: More than anything, this Portland Web Innovator session is about a regular guy who rose to prominence by deciding to follow his passion. Andy was straight out one of the humblest high profile presenters I’ve ever met.

    What I Learned From The Event In Six Words:
    Do it because you love it.


2 thoughts on “Portland Web Innovators – Andy Baio Talks Side Projects And Acquisitions: An Event Review

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