Sep 8, 2008

Joel Spolsky’s Business of Software Event 2008

spolsky-fried.JPG3 of us MailChimpsters were in Boston last week for Joel Spolsky’s Business of Software Event. Spolsky describes it like this: "The audience is made up of pretty serious software companies…typically companies that are quietly making money selling software that people actually need, so they can afford to go to these conferences. " It’s a great event. Actually, scratch that—I don’t want too many people coming and ruining the entrepreneurial environment next year—so um, this is an awful event. Don’t go.

On day one, we had speakers like Seth Godin, Jason Fried, and Eric Sink. I noticed they each had 3 different takes on that classic bell curve used in crossing the chasm:

  • Eric Sink talked about the stages your company (baby) goes through as it grows and crosses the chasm.
  • Seth Godin discussed the outer edges of the bell curve (scarcity and ubiquity) and the deadly part in between
  • Jason Fried talked about how much fun you can have simply by staying riiiight on the edge of the chasm, and anyways why the f- would anyone ever want to cross?

Alexis Ohanian, founder of Reddit, did a super fast and funny parody of Jason Fried (hey, if they’re teasing you it means you’ve made it). Here’s a slide where he preaches that software to change the world is for hippies, and how money is the ultimate goal:


All in good humor.

Dharmesh Shah, from Hubspot (a MailChimp user) and blogger at OnStartups, had one of my favorite presentations on growing your startup, bootstrapping, and why VC money is really bad (but actually sometimes ok). It was off the cuff and very entertaining. If you’re a startup, bookmark his blog for support and inspiration. Afterwards, I got to speak with Dharmesh, and he gave me some tips on getting MailChimp’s dismal Twitter grade up.

Speaking of startups, Jessica Livingston from Y Combinator spoke about lessons she learned while writing Founders At Work. That’s got to be one of the best books about startups business I’ve ever read.

As I said, this event is for real entrepreneurs, so it wasn’t a surprise that we ran into the folks at Campaign Monitor. To give you an idea of how great this event is, these guys flew 30+ hours to get here. Come to think of it, half the people there seemed to be from different continents. Anyway, we had some great conversations, and discussed some potential strategical synergistics between our companies. Here’s an incriminating photo:


(Ben, Ben, and Dave)

We also had the chance to sit down for breakfast at the table with Seth Godin and Joel Spolsky, and not talk about business. Sort of. We talked about rent (I always wondered what Joel pays in New York) and we discussed the logistics of feeding your entire company lunch every day as your business grows from a tiny startup to a couple dozen employees, to Google. And of course, Seth drew a graph for this.

On day two, we heard from Tom Jennings of Summit Partners, who gave us the VC’s point of view on business deals. Noam Wasserman presented findings from his "Rich vs. King" studies at Harvard (by the way, the correct answer is rich—there, you don’t have to take the class). Steve Johnson made us laugh and cry with his discussion of Pragmatic Product Management. Richard Stallman skipped an appointment with his dentist, despite his agonizing toothache, and taught us how evil software patents can be, and how you should only say "intellectual property" while doing little finger quotes in the air. I’m not enough of a nerd to understand this dude’s historical significance, but I can tell you this dude is intense.

Steve Krug did a fascinating live usability test on an audience member’s website (

Joel Spolsky ended it all with a hilarious presentation on the importance of emotion and design in software (an interesting topic to present to 300 software developers). You gotta appreciate the fact that his powerpoint presentation was pretty complex and sophisticated as PPT files go (he actually did a little "programming" in it), but the average user would have never noticed. They’d just sit back and enjoy the LOLcats pictures. Which was exactly his point.

I have to say my highlight so far has been sitting down at a table with a guy named Phil, a complete stranger to me, and asking him about his business.

He makes accounting software for oil companies (as in cowboy hats and giant drills).  I love hearing about extremely unique businesses like this. It’s called SherWare, and it interfaces with Quickbooks. Anyway, when he found out where I worked, he said, "Wait a minute—we use MailChimp!" So that was fun getting some real user feedback from a real customer. Small world. And what a great, inspiring story he had about his daughter. Phil, that was probably the best business story I heard the entire time I was there!

If you think you might be interested in next year’s BoS event, be sure to sign up for their mailing list, or follow Joel Spolsky’s email newsletter (that’s how I heard about it).  His email signup form is in the footer of his blog.

Our next event will be the Webmaster Jam Session 2008, here in Atlanta. Actually, 2 of us from MailChimp will be speaking at this one (more details, plus a promo code coming soon via email to MonkeyWrench subscribers). Hope to speak with some MailChimp users there too!