How I won Startup Weekend

Last weekend I took an idea I had been working on to Startup Weekend and ended up winning the competition – including $5k in cash and $8k in miscellaneous prizes. 

The idea was Theme Pivot – a CSS-specific marketplace that helps take your CSS from “good enough” to pixel perfect. The idea is that editing CSS is often a painful experience, even for seasoned web developers, so we want to create a fast and easy way to make changes for people without the time or skills.

It’s an integrated workflow which makes this process easier and a marketplace to connect you with people to help you do the task.

1. Come prepared

It didn’t really occur to me to come prepared with a well thought out pitch on the first night. I had a couple of ideas that I’d been thinking about and vaguely working on but didn’t have a succinct way to get that across. If I’d just written down the salient points I would have been fine.

2. Say it straight, then say it great

When I pitched my idea on Friday night the response was mostly indifference. The one thing I tried to do was follow the maxim from a smart copywriter I know: say it straight, then say it great. 

So I lead into my pitch with “we’re 99 Designs for CSS”. It seemed to strike a chord with one of the judges, I managed to win a spot prize for the pre-pitch based on getting aside my concept in four words. It wasn’t representative of the broader vision for the project but it was a good shortcut.

3. Iteration is key

I’d been working on the idea for Theme Pivot for awhile but I still hadn’t worked out how to describe the vision succinctly. I presented it twice before I did the Friday night pitch and still sucked. I then pitched a group of people at the end of Friday and convinced them enough to join me. 

By the time I got to pitching it on Sunday night I had practised the pitch 15 or 20 times with multiple people and it was close to being perfect – or as close as we were going to get. And that was close enough. 

4. Surround yourself with great people

You are the sum of the five people closest to you and you need great people to do great work. We managed to pull together a demo and a winning pitch in a weekend – something that I think came down to not only a great idea but also a great team. 

The input from mentors at Startup Weekend like Leni Mayo also made a huge difference. 

5. Focus on the user

We initially thought that Theme Pivot was going to be for anyone with a WordPress or Tumblr blog. We thought this because we had blogs on these platforms and so did our friends – and they often ask us for to make “little” changes for them that could drag out into hours.

However, when we got deeper into the problem we realised that web developers were our primary market: they knew what CSS was, they had the pain point and they had the capacity to pay to make their problem go away. 

We could then focus on making the experience seamless for this group of people.

6. Enjoy yourself

Startup Weekend is an intensely rewarding experience. It’s a chance to meet the smart start-up types in your area and maybe find a co-founder or create the start for something beautiful. Relax, have a good time, enjoy yourself.

If you’re thinking of doing a Startup Weekend I cannot recommend it enough.