photo of cohabit’s ui map from startup weekend women’s edition

Startup Weekend: The Good, The Bad, and The Ugly.

Confessions from a leaning-in-ing designer.

Three months ago, I plopped down next to my friend Karen, the most empowered person I know, and sighed like the emo designer that I am: “I still don’t have a job. How does a designer start in this town? #sadface.” She rolled her eyes at me and was all like, “Stahp. Just go to a Startup Weekend event. Design things. Isn’t that your job?” (I’m paraphrasing. Karen was actually nice about it.) I went online, and signed for the first San Francisco Startup Weekend event I saw: Startup Weekend Women’s Edition.

Well, I went as a designer, and found myself a team. We worked for 50 hours. At the end, my team, Cohabit, won. We won both the grand prize, and the popular vote. It felt awesome. People were tweeting at us, and about us. My team group-hugged. We group-hugged all the other teams (graciously). We shook hands with the judges. Got business cards and promised to find each other on LinkedIn. I called home. I even cried! I felt like I was winning the Miss America pageant… of entrepreneurialism.

Since winning, I’ve had some time to reflect on my Startup Weekend experience. I’m still giddy I won, but the overdose of group-hugs triggered my need to get some real-talk out. (I mean, I did spend the last four years in a real-talk, blue-collar kind of town — go Pats!) So here it is, my Startup Weekend experience: the good, the bad, and the ugly. Here we go.

The Good

• I won! Actually, my team won. We’re all women, and we made it happen together. Not only some cool prizes, but the win and the experience also gave me confidence in my own abilities as a designer. Since graduating from design school, I had the opportunity to make significant contributions to the success — or failure — of an idea. There’s so many people who say they need designers, and after this weekend, I can see why they would need me.
• I got to work. Wireframe, mapping, layout, branding, identity, flow, mockup, flat design, hierarchy, information architecture, user experience, user interface, designing for the future. All the design tricks I knew I got to show off. I felt like a purebred at the Westminster Kennel show, showing off all of my tricks and training, and design genealogy. This must be how Michael Phelps feels at the Olympics — in my element, man. I live for this. Others might have seen this 50 hour timeframe as a constraint, but I saw it as an opportunity to really immerse myself into doing something I love professionally, and be appreciated for it. It felt satisfying to work on my craft.
• I got to expand my portfolio by doing a full UI mockup. I’ve been interviewing at big and small companies, and everyone kept asking, but can you do UI?? After a couple of rounds of this, even I was doubting that I can do UI. I mean, I get it, I come from an academic design background. How do I prove I can do UI? Definitely not by showing my random poetry generator project (btw, this is a book. Not a coded website. Sorry not sorry). And this was the perfect opportunity. Since then, I’ve booked three great contract gigs where I can do UI work. Get money get paid, and I love it.
• Networking with people who can help me make connections to advance my career. I met the lead of Product Design at Facebook, the CEO of Wantful, a board member and advisor of Golden Seeds, and the founder of Black Girls CODE.
• Meeting the mentors who came out and laid it out straight. My team came in with a good idea, and our mentor, a serial entrepreneur, helped us tease our “nice idea” into something marketable, and kept it grounded at the same time by our business case. It was inspiring to see a business-minded person solves problems.
• I did the logo for the event. I got to see it all over everyone’s swag, and got acknowledged on opening night. I’m glad that a women’s event can have a logo designed by a woman as well. Also, I know it’s gauche, but swag swag swag.
• I really enjoyed the snacks provided by Juniper. Appropriate right? I mean, a woman started company that provides care and pampering to women, is providing and caring for an event catered towards women. It’s like the event is trying to empower women or something! Amazing.

The Bad

• So many STEAM ideas, so little differentiation. (STEAM: Science, Tech, Engineering, Arts, and Math.) In a room of 95 people, 14 people came up with 4 similar STEAM ideas to empower women and girls. Then, it got lumped into one giant team.What is STEAM even about anymore? Is it a literal approach? Is it about awareness of STEAM careers as options? Is it about mentorship and empowerment? Is it about connecting girls with peers? Is it about meeting peer-to-peer? These are all good ideas, but when you steamroll them together, it loses focus.
• Clearly, for some groups, monetizing is an afterthought. People didn’t think about monetizing until when prompted by their mentor. It was frustrating seeing ideas that didn’t make financial sense. Money-making should be empowering, but you would never know attending this event. Are we hustling, or are we hustling good-will here?
• In the larger groups, it seemed like the product was designed to please a 10+ people team. These people just met each other, and it was clear their ideas seemed to be fighting it out in the form of wishy-washy design. This lead to the design lacking in personality and voice. Startup Weekend is too short to both launch a product, and manage a 10+ person team.
• I didn’t see that much outstanding design. To me, good design makes ideas more compelling. Inexperienced design distracts from the idea, and makes the idea seem lame. The work I saw there reflected designers who had exposure to design. It would have been awesome to meet more experienced designers, who are constantly thinking about design innovation and pushing boundaries, but this wasn’t the event for that.

The Ugly

• There’s a lot of talk about empowering women, for obvious reasons. Everyone seemed really happy to have participated. However, I can’t help but feel like I was at a slumber party and we were playing dress-up. It was fun, but everyone was happy to go home afterwards. I thought this event would carry more gravitas than a weekend Napa excursion with girlfriends.
• Must we start every point with something along the lines of “I don’t want to invalidate your input but…?!” Like, I get it, we respect each other’s ideas, can we please move on. If I had a nickel for every time someone said this, or a variation of this, I’d be funding my own startup right now.
• While this is Startup Weekend Women’s Edition, it felt to me that the attendees were focusing on being women first and not entrepreneurs. Yes, it says women in the title, but I also think that people are over-thinking these words, and some of the people get attached to how they want to lead as women, instead of having to be a great entrepreneur. It’s like how that Jay-Z song goes, “I’m not a businessman, I’m a business, man.” I wish this was more about business, and less about being businesswomen, man.
• This is my first Startup Weekend, but I keep wondering, if this were a co-ed event, would they serve something more substantial than kale and quinoa at mealtime? Is massaging kale a trend?? Just like leaning-in is in right now? I JUST NEED SOME PROTEIN!!! I am a powerlifter, I need chicken!

Takeaway

I’m proud that my team and I won. The win really gave me the confidence boost when I needed one. This weekend confirms that executing on a good idea involves ruthless editing and thoughtful design, and cloaking ideas under STEAM and empowerment doesn’t exempt them from that process. Startup Weekend is capable of accelerating a project to give it momentum. But after a weekend orgy of startup-building frenzy, the race is still on. You have to stay in hyperdrive, avoid getting jammed, and aim for ludicrous speed. You can’t stop, it’s too dangerous.