Law & Order: Startup Weekend (Part 2)

In the world of startups, the teams are represented by three separate yet equally important groups: the developer, who get a tan from the glow of their laptop screens; the businessperson, who talk about random concepts of revenue streams and profit margins, and the designer, who’s probably on Twitter right now. This is one of their stories.


We were starting to realize we’d maybe bitten off more than we could chew. We needed to narrow our focus. We’d been trying to do an web app, and a native app. We were trying to decide whether we were going to focus on close friends or strangers. Were we sending gift cards? How did the retailers participate? Everyone had great ideas, we just were trying to do too much. Eventually, we narrowed the focus down to the experience of sending a cup of coffee to a friend. We weren’t going to worry about the business model, or the revenue, but a demo that showed that key, emotional experience. But someone had a problem with that. 

“So we’ve decided to focus on the main gift receiving experience for tomorrow,” I told the business team.

“How are you going to show the retail interaction?” Ken wondered.

“We’re not going to worry about that for the demo. We’re just going to show that experience, and explain the rest.”

“Here’s the problem with that. You’re not going to win. You’ve got a great proof of concept. Proof of concepts don’t win Startup Weekend. You’re basically demoing Giftly.”

I sighed and shrugged my shoulders. “Okay? I think that’s okay. This is a learning experience for most of us anyway…I think?” Rob and Dani nodded their heads.

“Well, that’s fine if you want to do that,” Ken said, “and I wish you guys the best of luck. But if you’re going to go that route, I can’t be involved.”

I looked at Dani and Rob. “So you’re going to leave?”

“With all due respect, and I have no ill will toward you, but Startup Weekend is about building a startup business in a weekend, not proof of concepts. I don’t think I can contribute to that.” 

Ken might have been a stubborn pain in the ass for most of the weekend, but he did bring some insights, so I didn’t necessarily want to see him go. But it also wasn’t my call. I brought over Phillip, and Phillip convinced him to stay. 

Shortly after that, Jenny Lam came to visit the group. Jenny was one of the judges, a designer, and founder of Jackson Fish Market. Like I mentioned on Friday, her talk at Creative Mornings solidified my decision to make the leap and participate in Startup Weekend. I’d quickly become a fan of hers. She was also very excited about our project, and said she wanted to make sure she came over to see what we were up to. At the time, not much. I still had sketches in my book, and had started poking around with fonts, because I realized I wasn’t going to have time to design a typeface from scratch.

Jenny talked about what drew her to our project was the experience of opening a gift, and how exciting that could be. She would love to receive a gift from someone, not know what it was, and have to find it. The idea resonated with her. Her mentioning the idea of opening a gift clicked something in my head, and I immediately started scribbling in my sketchpad. 

I had this idea that when you received a gift, it would be wrapped, and you couldn’t open. But you could spin the package around, shake the package. do whatever to it, but you couldn’t actually open it until you got to the location. Then, you’d swipe on your phone and “open” your present to see what the surprise was. I asked Dwayne, our iOS developer, if that was possible to do. He said it was, but that it’d be near impossible to do in the time we had. But he could definitely do it with a 2D animation to get the idea across. Everyone seemed excited about the idea. And I’d found my creative inspiration for the rest of the Supr!ze brand. 

“Here’s the problem with that.”



Rumors of snow had been rumbling around the office all day, and the room starting slowly thinning out, as people heading home to beat the snow. This meant we were losing two of our developers, one of whom lived at the top of a hill in Kirkland. I have in-laws that live at the top of a hill in Kirkland-I know how that works out when it snows. 

But despite that setback, we were steadily moving ahead. We were terribly behind schedule, and walking around the room confirmed that. Several teams had teaser sites up, Twitter accounts going, and had actually started working on their presentations for Sunday. We’d spent too much time arguing, too much time buried in minutia, and now we were losing the guy who could have gotten a working iPhone app and running. But despite all of that, there was a good buzz in our corner. We’d tapped into Phillip’s emotion, and we were all moving together towards our goal. 

I knew that I was going to have a late night ahead of me, but that was perfectly fine by me. I do my best creative work late at night. I was going to obsess over this design anyway, and it would be best to do this while I was at home where I couldn’t be distracted. I had some big ideas for the presentation, and I wanted to get these screens done, so that I could pitch in on that first thing in the morning and really drive the project home. 

I packed up my stuff and headed home.


There’s a certain energy I get when pulling overnighters. Tonight was no different. Having crawled into my sweatpants, and cracked open a beer, the ideas started free flowing as I started fine tuning my design. I have a bit of a reputation for being a tireless perfectionist, to the point of it keeping me from actually showing anything to anybody. The necessity of our tight deadline meant that I didn’t have time do that. It probably won’t surprise anyone who knows me that I hated the final screens that we wound up showing-I kept thinking of ways that I could improve it. But I needed to let it go. I sent it off to my team, and wandered off to bed, where I would probably asleep before I hit the-


*punches alarm clock*

11:00 AM

What’s that saying about best-laid plans?

I had planned on finishing up my Surpr!ze screens and handing them off to the developers, then jump on helping Phillip with the pitch, but Gerry thought that he could get a working prototype working. And the developers wanted to get a web app going that we could share. Fantastic! I pivoted and dove into helping Gerry prepare graphics. Gerry had some great insight into the user experience for the app; this wasn’t surprising to me, seeing as this was his job, but it was fascinating to watch him work. I’ve used countless apps on my iPhone, iPad, Android tablet, and anything else you could think of, and I’ve never really thought about what made apps simple and intuitive to work. I’ve always been super focused on the visuals, but I can think of a number of apps and sites that I’ve stopped using because there wasn’t much thought into how the end user would interact with it. This was why I signed on for Startup Weekend, I wanted to learn. Gerry took my pretty pictures, and made something usable out of them-we wouldn’t have had anything usable if it wasn’t for his work.

Meanwhile, Phillip was starting to circle the room, putting the presentation together in his head. Because of the weather, our presentations had been cut from 5 minutes to 4. This probably worked in our favor, seeing as we hadn’t really started writing anything yet, but we didn’t realize that at this point. Phillip, Dani, and Rob had found a secluded spot of an a different floor to get busy with the presentations, while Gerry, myself and the developers busied ourselves with getting the prototypes ready. 


I walked into the conference room, where Phillip, Dani, and Rob were working away on the Keynote deck. I was convinced that the key to our presentation would be the story behind Supr!ze, that feeling of wanting to surprise a loved one in a fun way, but not having any way to do it beyond some boring gift card. I thought the visuals were going to be the thing that brought the experience home. Gerry had put together a wonderful prototype of the app, and we shot some video of it, for the demo part of our show. Those three things were going to be the thing that brought the house down, I thought. Dani, Rob and Ken felt strongly that we needed to have our business plan in there, to talk about how we were going to make money from this thing, and how we were going to find our first ten customers. We were both right. But we only had four minutes, and an hour before we needed to test our laptop with the projector to make sure we weren’t going to have any technical issues. I was starting to get stressed out, I know Phillip was starting to get stressed out, and we were once again starting to talk over each other like we did on Friday. Finally, Phillip said, “You know what? I just need five minutes to get my thoughts together. Everyone leave, and give me that.” 

I think because we were so behind, and we all thought our parts of the presentation were equally important, which they were, that we were trying to cram everything under the sun in there. We didn’t edit anything, because we didn’t have time. We didn’t time our presentation, hell, we didn’t finish our presentation. We were basically going to wing it, rely on Phillip’s passion and charisma, and then get the hell out of town. I had no expectations of winning, I just wanted to emerge from night relatively unscathed.


It was time for the presentations to start, and my team was nowhere to be found. I was concerned that we were over thinking the room, and I even grabbed one of the mentors floating around and sent him into the room to convince them to wrap things up. Plus, I wanted to see the presentations. Wasn’t that the whole point? I texted Phillip, and told him it’d probably be good to hear the presentation and the questions they were asking. I had Ken in my ear all weekend telling me that the judges’ questions would be brutal, but for the most part, I didn’t hear anything too vicious. During a pitch about contract job services for stay at home moms, the speaker mentioned his service would make it easy for stay at home moms to “find a real job”. At which point, judge Rebecca Lovell quipped, “well, I have plenty of friends who are mothers, and they consider that a full time job, so I tuned you out after that.” But that was really the worst of it. I thought as long as Phillip got his story out, got through the demo, and get the general business model out there, we’d be fine. 

“You okay?” I asked.

“Yeah,” Phillip said, leaning over his laptop. “I’m just trying to get the story straight in my head.” 

“Okay,” I said. “Let’s go over it, see how we’re doing on time.”

We knew the demo was a minute, which got us down to three minutes for everything else. Knock out a minute for the background and story, and we had two minutes to get everything out there. We had approximately 832 slides to squeeze into that two minutes. No problem. 

“Look, take a deep breath,” I told Phillip. He did. “Everything is going to be fine. Just go up there, take a deep breath, get through what we’ve worked on, and if you don’t get to the business stuff, we’ll tackle it in Q&A.” 


“Listen, guys,” I started. There was a break in the presentations, and we were slated to go second after that. “No matter what happens out there, I had a great time working with all of you-win, lose or draw. This was a great experience, and regardless of what happens tonight, I’d love to keep working with you guys.” 

Everyone congratulated each other on a great weekend. I put my hand out. “Okay, guys. Surprise on three. One, two, three…”


I’m not sure where things went wrong. Maybe it was when we plugged the laptop in, and it decided not to work. Maybe it was when Phillip started out well, missed a bit, then began laughing, and stammering on about how his weekend went. Maybe it was the point where Phillip swore, said, “shit, I just said shit. I’m sorry. Shit, I did it again.” Maybe it was when I literally started to make that “cut” gesture when he wouldn’t get to the next point. I don’t know, but in my eyes, it was a disaster. A wonderful, fantastic disaster, but a disaster nonetheless. 

Everyone loved it. 

I think it was because I think going up there and stammering through your presentation was everyone’s biggest fear. Maybe it was because everyone could see Phillip’s excitement and fed off of it. I dunno. But outside of the clucking chicken robot, I think we had one of the more memorable presentations of the evening. After Phillip finished, and the judges mercifully took it easy on him-he didn’t even get to the business stuff, nor did they ask-we went down a few floors to celebrate. We were all excited, and I think we had reason to be-when Phillip was going through the demo, at the key moment, where the user opens the gift, I heard a couple of gasps of delight behind me. I knew we had a winner, even if we didn’t win anything. 

So when Jenny Lam (!) announced that we had won Best User Experience for bringing “delight and surprise” into our application, I was floored. Actually, first I was bummed, because my personal goal was to win Best Design, but that went to Which Bus, which had a beautiful presentation and app. But when I realized what winning Best User Experience meant, I went through the roof. That was a team win, by every stretch of the imagination. I was so proud of the work I’d put up there, and more proud of what I learned over the course of the weekend. 

Afterwards, a couple of filmmakers who had been filming the weekend interviewed Phillip and myself. This was a weekend dedicated to the “Rise of the Designers”, and of all of the groups, four were led by designers, and one-us-were being led by two. I told him that this weekend was pretty much a personal validation of everything of everything I’ve been trying to do since I posted that crazy manifesto of mine a few weeks ago. Prior to Friday, I’d never designed an iPhone app. I’ve talked about it, I’ve sketched them out, but I’ve never made a finished product. We are well on our way now. I’ve never led the design of a product launch-I’ve done that now. I’ve talked about wanting to start any number of different businesses-we have a framework for that now. I’ve even leaned on my past experiences in my career to work with business people-I’m no longer the bitchy diva I was at Apartment Guide all those years ago. I thought about all of that when answering his question, and I got choked up a bit. This has been the most rewarding experience in my career. 

I was asked a few times this weekend what I’d tell designers about Startup Weekend, and if I’d advice them to do it. My answer? Absofuckinglutely. You’re going to learn a lot, about yourself, about business, about your career. You’re going to do things you never thought you’d be able to do, and work with some amazing people. And you’re going to grow professionally more in a weekend, than some will in a year. I was thinking about it on the way home-in a lot of ways, if Surpr!ze has an seedling of an org tree, Phillip is the founder, and I’m the creative director. I never thought I’d ever say that. 

Maybe it’s time to change the name of the blog. 

(photo credit: Kyle Kesterson)


Obviously, I wouldn’t be writing this without our fantastic team-Phillip van Rooyen, Gerry Chu, Michael Brooks, Hakon Verespej, Dwayne Mercredi, Ken Decanio, Rob Gropper, and Dani Harper. Thanks to the Hub for providing such an awesome space, and I look forward to setting up shop as Black Art Director in the coming months. Thanks to the Startup Weekend organizers, speakers, mentors-you all provided awesome support and advice all weekend. Thanks to the judges, Jenny Lam, Rebecca Lovell, Scott Rutherford, and Adam Phillipp-you guys were tough, but fair. And last, but not least, thank you to all of the teams that participated and all of the new friends and colleagues that I’ve met. I look forward to reconnecting with all of you soon.

Dwight Battle
Black Art Creative Director