Reflections on startups after Chicago Startup Weekend

This past weekend, I was a part of Chicago Startup Weekend. We (Some friends, my brother, and I) gave a solid college try at launching a minimum viable product (MVP) to help foodies connect to personal chefs and aspiring food entrepreneurs called BigStove. We did hone our message and are working on taking some important validation steps after putting up some landing pages.

The general idea behind StartupWeekend is that you work on an idea all weekend and launch/pitch at the end. Think TechCrunch50, except you build the MVP in a weekend. Pretty awesome way to work and validate your idea.

Chicago Startup Weekend

Chicago Startup Weekend

Thought I’d take a second to reflect overall on the experience:

On Personal Leadership:
– I realized a lot about my personal leadership style in a very short period of time. Having an undergraduate CS background, and a graduate degree in design and business sounds great and is helpful, but what’s better is being able to find people who are amazing at what they do and having trust that they can do a helluva better job than I can.

– Being an individual contributor as a leader is helpful when it can be managed well. It indicates that you care enough to get your hands dirty. However, remember to choose battles wisely. We didn’t need >2 people working on setting up the backend/Django. As an aside, we should have known that the “contest” wasn’t about actually building something, it was just about pitching. Only one of the other teams appeared to actually have something built besides for us.

On Startup Teams:
– I realized I mostly like working with people who DO stuff, and BUILD stuff. Talk, and ideas are cheap. Especially ones that aren’t informed by user research/talking to people.

– It takes people a while to understand that user research is about finding unique insights about how people operate and their unarticulated needs. When you have vague notions of what you want your product to be ALREADY, then this user research is harder to do. You tend to have a radar for points that substantiate what you intend to build. This happens all the time in larger companies when managers are undergoing new “innovation” efforts.

Desired/Undesired Behaviors for Startup Teams:
The great thing about startup weekend is that it’s a great place to test out how a team is working. In a sense, it’s by far, the best place to “interview”. Experience high stress, move quickly, get done a bunch of stuff over a short period of time.

— Integrity. Being able to trust all the members of your team is important. Don’t do things that put that integrity into question. Though I forgive and forget a lot, matters of integrity are pretty important.
— Solid work ethic. Working with some people is an absolute pleasure because they just have an intense curiosity to just GET IT DONE and show the results of what they’ve done after they’ve done it. The work is inherently valuable and takes the team to a new place.
— Don’t be afraid to pitch constantly, it helps refine the message. Agree to a pitch as a team and then try it.
— Disagree and Commit. It’s okay to disagree, but once everyone is on board with the same plan/vision, commit and move on.

— “Management” mentalities. There’s little scope for project management for the span of a weekend. Just build stuff. Even if it’s a map of what you think needs to be done.
— The Blame game. It’s too easy to blame other(s) on the reasons why something didn’t work or you didn’t get done what you needed to get done. This is a deleterious behavior and doesn’t convey personal ownership. Startup teams work best when people PRIVATIZE LOSSES and SOCIALIZE WINS, not the other way around (e.g. Awesome job on this data model, guys….. Sorry I F%@$% up our Q&A session, I know what I’ll do next time)
— No man is an island. Cliched, but prima donna “artistes” don’t carry the team. Unfortunately, I was harsh on a team member for doing this. Luckily, the team member was my brother, so no love lost.
— Passive Aggression. * I didn’t notice this much this weekend but I have with startup teams in the past. There’s no room for facetious passive aggression in this environment. Better to be aggressive, provide reasons for why you believe the way you do. This really gets to me.

On Lean Startups
— The importance of “getting out of the house” is immensely valuable. We’ve met 23 people across 5 food markets in 3 cities. We’ll talk to more in order to drive them to our landing page and see how easy it is to convert/gauge interest. We’ll only build if there’s verifiable interest.

bigstove leanstartup steps

On Startup Weekend:
— The Startup Weekend, Mark/Chris,et al did a great job at putting the weekend together. Enjoyed spending time with most of the other teams/entrepreneurs there that were building businesses.

– Regarding the “contest”, I thought some of the ideas were great — I especially liked RemnantRetail — and thought that they should surely have won. Amazing that some of these companies / visions are developed in a weekend — It takes some TC50 companies a year to get where they are to launch. I also really liked City Murder. Think there’s a huge oppty for “real” social games that I’d maybe actually feel like playing (I’m not a gamer). I thought it was bizarre that the second place winner was literally partners with one of the judges, but I’m not surprised, this is Chicago after all.

Respond to me on Twitter: @AshBhoopathy or follow the discussion on HN.