Portland Startup Weekend

I've barely recovered from an intense three days at Portland Startup Weekend, my first Startup Weekend Experience and an unforgettable experience of competition, code, and camaraderie.

I was finally induced to go to Startup Weekend because I'm conspiring to bring it to Tri-Cities and you have to go in order to organize one (more on that on a later date). My brother-in-law is in Portland so it was logistically simplest to attend. Finally, I've always been looking for a reason to meet up with a Jon Morales, who I bonded with over an open source project years ago and finally found an excuse to lure over to the west coast.


Portland State Business Accelerator

I arrived at Portland State Business Accelerator, a tech incubator I would sorely like to see replicated in Tri-Cities. I met with Jon Morales and Chad Downey, who both flew in from DC for a long-awaited meetup in meatspace. We settled in and tried networking amongst the 100+ Hacker, Hipsters, and Hustlers (their titles for Developers, Designers, and Business folks), as best we could in a cacophonous main room. We proceeded listen to about 45 pitches (so, an almost 50% participant-to-pitch ratio, very encouraging) to vote on the best ideas. We then formed teams around the best ideas.

When deciding on your team, it's really important to base your decision not just the obvious cleverness of the idea or ability to work with the desired technology of the founder, but you need to also trust your instinct on the vibe of the group when you approach. You've only had 60 seconds to listen to the "founder", but you get a few minutes to mingle with the team before it's final, so take that time to try to determine if they're going to be a herd of drama lamas.

Jon, Chad, and I chose ScoutAbout, and I believe we chose wisely.

Friday night was basically about getting to know each other, taking an informal inventory of skills, and setting a great expectation for the weekend.


 Team ScoutAbout

Team ScoutAbout

Saturday began with trying to layout an initial timeline for the day, which immediately starts sliding as every detail starts cascading into conversations about how to best quash the issues. We did "Get Out of the Building" to do some customer validation in the Portland Saturday Market. We then returned and laid out our best guess on an MVP. The 5-person software team, all .Net developers, went to work as quickly as possible.

We tried to use a number of .Net's rapid prototyping technologies, including Code-First Entity Framework and MVC Scaffolding. In the end, it's important to remember that while the weekend does bring together software devs to work on perhaps real first day of a real business, there is a delicate balance between what is faked for the purposes of Sunday's 5-minute presentation and what is potentially foundation for a real product.

Our biggest technical challenge wasn't actually code, it was source control. I had urged the team to use Git, which everyone was more than happy to go along with before the GitHub for Windows client started detaching heads like George R.R. Martin. While Git is good with moving the source around, the merge tools are definitely inferior to the MS dev's experience with TFS. Next time, I guess we should just use Subversion.

In my observation, you only need a real back-end if you plan on offering a demo on Sunday that shows both read and write interaction across more than one client; otherwise, do yourself a favor and just use JavaScript plus LocalStorage to show a pretty version. In the end, we cut our write features, so we ended up with something very heavy for a read-only demo.


Sunday is all about the final five minute pitch, plus five minute Q&A with the judges. We had to do a lot of work pulling together the prototype in the morning, but by the afternoon it was just about pulling together the slides and content. The Hipsters and Hustlers were working furiously, the Hackers were just searching for areas to plausibly polish without breaking anything.

Mentors did keep coming by and providing feedback. While it's certainly important to be flexible with your idea on Friday and Saturday, Sunday is all about churning out 5 distilled minutes on the idea you have customer validation and a clear business model around. In the end, feedback on Sunday is better put to use as a vision for the future past Monday rather than trying to incorporate it into the pitch.

The live stream of Sunday night was uploaded to YouTube and our pitch is about 45 minutes in. As you can probably see despite the low quality, the impromptu nature of the pitch means authenticity and energy are, in some ways, more important than quality content. Also, unlike a purely VC-targeted pitch, it's not just about the product it's also about all the effort over the whole weekend.

In The End

After all that hard work, we didn't end up in the winner's circle. The teams who did, Wijjly, LivFly, and my personal favorite, Freezepup, richly deserved it and I absolutely relate that one of the purposes of Startup Weekend is to allocate the resources of a community behind it's members who have focus and promise.

I am so proud of what Team ScoutAbout was able to accomplish in just 54 hours. I'm thankful to have found people who made my first Startup Weekend experience great. I hope our founder True, and perhaps whatever parts of our team are willing to stay on, will keep moving forward with her vision. Ultimately, the judges gave a result, but since I am so eager to do it again, I feel like we all won.

Team ScoutAbout in Action