Wayne Sang
Design and Product


Startup Weekend Toronto

Startup Weekend Toronto

Startup Weekend Toronto

I flip-flopped on going to Startup Weekend. I always flip-flop on events, but I'm trying to say "yes" to more as a point of personal development. I had been sitting on an idea for awhile, and I like cultivating these things slowly while paying attention to every detail along the way. But I'm also aware that I'm terrible at being my own client (like many designers are). I cringe when I show a design to someone that isn't finished, and that's difficult to grapple with when trying to do a startup as you need that early feedback. It's never really finished.

Startup Weekend would give me kick in seeing whether the idea would sink or swim, plus it would just be a great experience overall. I finally decided to buy a ticket on Tuesday of that week, but when I logged onto the site all I saw was Designers: Sold Out. I was equal parts frustrated and relieved. Fine, I had alternative plans to develop the idea. No big deal. I immediately tabled the idea again and got on with other work.

Then on Friday, hours before Startup Weekend would start, a friend of mine emailed me to let me know she had a spare ticket.


I was working at a client's office at that point, so after reading the email I turned to my client and asked for a sanity check. He graciously set a timer for 90 seconds while I tried to pitch the idea at him. It was rough, but substantive enough to warrant going, so I replied with a "yes" to the spare ticket, finished up work and basically started heading downtown while hashing out the pitch in my head.

Friday Night: Pitch Fire

When I arrived to check-in I bumped into a friend I haven't seen or heard from in several years, and on the other side of the country at that. A whole career ago really. He was pitching an idea too (which turned into booked.io), so we shared previews of our ideas. Totally serendipitous, and we're still talking to see if we can work together.

A "pitch fire" is a 60 second pitch with no visual aids. Introduce yourself, sell on the idea, and tell people who you want joining you. It's intense.

Once we got inside I learned that the pitch was in fact 60 seconds, not 90 seconds. That's... pretty different when it's a fast pitch with no visual aids. So while many others were networking I was stressing out on my phone trimming lines and whole paragraphs from my pitch, which was already way too fast. Thanks to some feedback from @rkenedi I was able to pare it down in time.

And when I say in time, it turns out that I actually had tons of time because the line was insanely long. Approximately 90 people pitched in the first round that night, and I was in the last third or so.

Thankfully my pitch went pretty well too. I'm not a frequent public speaker so I tend to rehearse a lot. If I do I can swing it pretty well, and I really had no excuse for a 60 second pitch.

Then came the next part, which was another into-the-fire experience.


Every attendee had 3 votes to choose who went past the first round, and we had about 30 minutes of networking, campaigning, and recruiting before the voting closed. Out of the 90 people that pitched, about 24 would get through. It was messy, especially since about half the people there had actually pitched an idea so they were trying to sell you on theirs at the same time.

I came out of it with a few leads, but I didn't feel particularly optimistic. I just didn't feel like I covered enough people there or had met enough developers.

Turned out I was wrong! I did get voted past the first round. Also I hadn't even used my own votes (I had bought someone else's ticket so I couldn't log into the voting site using my email). Phew.

The smallest team around

I had some scattered interest in my team, but I just didn't have a solid core. I wanted devs with iOS experience and some backend devs, and it wasn't happening yet. I had connected with another startup that had pitched earlier, and was hoping that they'd merge with me since they hadn't gotten voted through.

As the they discussed amongst themselves, the evening tapered down and people started leaving. That included the scattered interest I had assembled. To be blunt, I really didn't mind. The people that had expressed some interest didn't have a defined skillset that I could see contributing to the idea. It seemed like I was going to get the merge or I'd be jumping ship.

When 11:30pm rolled around my spirits were low, but I finally got a positive response from the other team! I had offered to trade some design time on their startup in the future, so I had bartered my way into survival. We left on Friday night with a team of 3: Myself as the designer, and two great all-around devs with iOS experience.

I saw some teams that appeared to have around 10 members, and that seemed crazy. I had been advised from some friends that smaller was probably better, and decisions became difficult even around the 5 person mark, so I was happy.

Saturday: The real work begins

Alright, first of all I picked a spot in the back corner. The idea was a bit of peace and quiet, and we had a bit of that, but like everyone else we were continually interrupted. What we also had was no natural light, and a literal pile of trash growing next to us in what appeared to be a freight elevator.


No matter! On we went. I had sent my team some notes the night before to give them more context to think about, and what feature we would likely need to cut. I thought I was being cautious and realistic. In hindsight that was a total joke, as there wasn't time for anything close to... well, any of that.

Bottom line: I could have really used another designer. I thought we'd be crunching out a prototype and we'd be dev limited. I was very wrong. Some teams cranked out some working products, and other teams are design limited. We were way into the latter.

We needed a brand, a landing page, UI mockups for iOS and for web. We also had to make and rehearse the presentation for Sunday at 4pm. That's a lot of design work.

But I didn't realize this stuff on Saturday morning.

We started with hashing out the idea and figuring out what was technically possible. Thanks to my excellent team we also sussed out some major technical hurdles and interaction difficulties I hadn't anticipated despite all of my quiet contemplation prior to Startup Weekend. No matter how much I thought about it independently I was never going to reach some of the conclusions they reached through their completely different backgrounds.

We got some great support from interviewing others at the event, and we started to feel good about the direction we were moving in. But as time ticked away I had also gone from thinking "loose working prototype" to "tappable mockup prototype", and then just to one feature tech demo with mockups in the deck.

It was the mid-late afternoon before I could sort of put my head down and take a crack at it. I had to get the wires out as quickly as possible to communicate the interactions to my team, and then I had to crank out the mockups.

By the time 11pm rolled around again they were more or less done with the tech demo (which was awesome). I had finished the wires and was partially finished the high fidelity mockups. There wasn't much work to split, but fortunately our senior dev volunteered to draft out the presentation content that night, which was a huge help.

That still left completing UI mockups, the brand, the landing page, and web UI to create overnight. I wandered home (a solid 1.5 hour journey) so I could use my 27" iMac and really get shit done. Some people had brought big monitors or entire iMacs to Startup Weekend, and I had a 13" Macbook Air. Great for satellite working, but not for designing ALL THE THINGS in 36 hours. My iMac at home was a welcome sight.

I finally passed out around 4:30am at home, partway through the web UI. But I got the other stuff done. It was rushed as hell, but I had no choice but to call it. Such is Startup Weekend.

Sunday: Get it done

Woke up late, arrived a bit late. Cranked out the last designs, and around noon we started working on the deck.

Up to that point we had worked so much on the details of the workflow. And you know what? So little of it actually ended up being conveyed in the end. I do think it was necessary, as working through those details helps validate the broader points you try to communicate in the end. It was just unfortunate that I spent time doing detailed mockups and we skipped them as they just weren't important enough. A lesson for the future on priorities.

T-minus 30 minutes to presentation time, and we didn't know what the presentation order was. I ran off into the stairway to rehearse again, and got pulled back by my team when the presentations started. We had no idea if we'd be first or not, and I didn't feel comfortable yet.

We were the second last presentation of the whole night. We presented roughly 2.5 hours after the presentations had started.

During that time I had missed most of the other presentations, but I had rehearsed the hell out of our own. Our general plan was me presenting the bulk, one of us working the slides, and both devs doing a live demo in the middle of it. Easy.

Then the projector cable failed.

I don't know how many slides we showed, but it wasn't many, and the colour and brightness were jacked up such that it was hard to tell what anything was.

And you know what? It turned out pretty well! The insane preperation paid off and I managed to wing most of it. I had brought my iPad as reference, so when it came time to show our brand, I just flipped it around and held it up. Also, most of our slides were just a few words each with no visuals. Aside from the mockups we just didn't need them, and the cable kicked in for those. We knew that busy slides weren't useful, so we went extremely minimal, and that worked great.

The tech demo worked out too (although I couldn't see from my position). They were turned away from me, so I only realized it had worked when the audience started clapping. Talk about relief, phew.

Wrapping it up

No, we didn't win, but I was really happy with how we came out of it. I had heard that at least one team had dissolved from in-fighting, and one had been abandoned by their creator on Sunday. We came out of it proud with what we accomplished, and better all-around for having worked together.

We still got some interest after the event, and me and my team are still talking with each other about what to do in the future. Even though we consistently felt like there wasn't enough time, I couldn't have been happier with our little team of 3.

Now, two questions I asked myself in the following week:

Would I go again?


Would I try to start a company there?

I'm not so sure.

It was a tremendous experience and a huge kick, but the sheer velocity of the event changes how things develop to me. Deeply considering every detail is just part of how I'd want any company I'm involved with to go about things, and that isn't exactly the point of Startup Weekend. I would return and join someone else's team just to have fun and meet others, but I'd personally think twice about starting my own ideas there.

Coming out of it I may be involved in two other startups from that weekend, and I managed to meet new people and re-connect with several others that I had lost touch with. Networking while doing real stuff is a great situation for that.

My experience during that weekend and what has transpired as a result have been great for me. I'd definitely encourage others to give it a shot, with or without an idea. Do the pitch fire or just join a team. Doing stuff is good.

Wayne Sang