A Startup Weekend, Darkly

Mar 2013

(Based on a talk at Startup Weekend)

“Most people would succeed in small things if they were not troubled with great ambitions.”

– Henry Wadsworth Longfellow, Drift-Wood

“This is a story about four people named Everybody, Somebody, Anybody, and Nobody. There was an important job to be done and Everybody was sure that Somebody would do it. Anybody could have done it, but Nobody did it. Somebody got angry about that, because it was Everybody’s job. Everybody thought Anybody could do it, but Nobody realized that Everybody wouldn’t do it. It ended up that Everybody blamed Somebody when Nobody did what Anyone could have.”

– Author Unknown

I was asked to give advice for a Startup Weekend. I’m not sure if I’m really the right person to do this since I’ve never actually won one. But I have participated in 2 and placed in both of them. So if you’re measuring precision I score highly but if you’re measuring accuracy then quite poorly.

But the two I’ve participated in have been really huge. The first Startup Weekend I did was in a team by myself, about April 2012, last year and the first time I ever started working on Medicine. I ended up coming 3rd winning an Ipad which I gave to my little sister for her birthday. But Medicine is still going, got accepted into a bunch of accelerators and is hopefully going to become a huge sustainable company one day.

The second Startup Weekend I did was in July 2012, later that same year in a team with Tom Pisel, one of my best friends from high school. We built and launched Tramsurance which had pretty much no users by the end of the weekend but came 3rd winning a Samsung Galaxy Tablet. But we re-wrote the site and relaunched later that week on Wednesday. By the end of the week we had nearly 50,000 users, were front page of every major newspaper, on every tv and radio station, made a bunch of Big International magazines and were the most talked about story in the country. We got a number of cease and desist letters, a lawsuit and were shut down shortly after.

You can think of Medicine as a logistic function which grows increasingly larger over time whereas Tramsurance as a surge function which burns really bright at the beginning but runs out quickly. It’s also worth mentioning that we were the youngest team in both of them, I was 19, Tom was 20. So anything is really possible and I don’t know if there are any real lessons to take from it. Instead I’m going to make some observations I think are interesting.

It’s profitable. Every Startup Weekend I’ve been to I walked away wealthier than when I entered. The simple math here is the ticket price is about $100 and the top 3 win prizes each valued at about $1000. So if you can place, immediately it will be a net profitable exercise, not including any sales made. That doesn’t even take into account the value created by the startup or the people you’ll meet there.

Build something then leave the building. One pattern I’ve noticed with teams that don’t seem very good is by the end of the weekend they haven’t built anything. And those that have built something don’t have any traction with it. It’s always struck me as odd. If by the end of the weekend there is no traction and nothing to show for it. What was the point? A good model for how I think the ideal team should work is they build something to the point it is barely usable, then try and sell it to people.

They’re a really good way to test out an idea or side project. Lots of people have good ideas they’ve always wanted to try but few opportunities to test them out. This is one of those opportunities. That’s how I treat it at least. Tramsurance started of as just an excel spreadsheet and a crazy idea Tom had that we weren’t sure would even work. It’s also a good time to try something new like an obscure technology or a new kind of sales strategy in a safe environment where no one will judge you.

Nobody knows what they’re talking about. I don’t think I met a single person who seemed to genuinely understand what they were talking about. Everybody kind of speaks with a practiced certainty as if they have deep expertise when really it is more of a rudimentary cobbled together understanding. Much like how a self-taught programmer might be very knowledgeable but have the fundamentals warped.

The tricky part is when they speak like they are sure of themselves. If the entire industry is based on exceptions to the rules, what’s the point in having rules in the first place? When drawing broad strokes often the picture gets distorted. I think it stems from a broad misunderstanding of the notion of a black swan or systematic random outliers. The entire startup industry is predicated on these but that it is an outlier is cause not to be able to predict it. So when someone says anything with certainty, they are invariably wrong.

Figure out what you’re working on quickly. The biggest mistake I remember seeing is when teams spend the entire weekend talking about what they’re going to work on but little time actually working on it. Usually that happens with larger teams since everyone has to figure out what they’re supposed to be doing instead of doing it then they end up fighting afterwards when nobody has done anything. They usually spend the whole weekend fleshing out the idea and only end up with a nice powerpoint presentation by the end of it.

I never understood what people meant when they talked about bureaucracy until I’d seen it and is why I understand now the conventional wisdom that startups work best with teams of 2 or 3. It’s not because they couldn’t be more productive with more people, it’s that people themselves are less productive when there are more of them. I think it’s because in a team of 2 you just look over and say you’re working on X. But in a team of 6 you have to almost do a ballot to see who works on what and that means first getting everyone in the same room and agreeing in the first place.

If there was one impediment to getting lots of work done it is having a large team whereas you’d think it would be the opposite since you have more resources to deploy.

Don’t sleep. It’s only one weekend and time spent sleeping is time not working. Normally that would be bad advice if this were say a job but it is good advice only if you count it as a one off occurence. You’ll make up the sleep afterwards anyway. It’ll be exhausting but you only have to keep it up for one weekend. Think of it as compressing your entire startup into a weekend the same way one might equate a startup to compressing your entire working life into a single entity. The teams that usually sleep end up falling behind.

Pick something really big. This might sound intuitive but actually it’s not. The prototypical startup that comes out of a startup weekend is derivative and usually only an incremental improvement on something already existing. For example, a CRM for salons or a booking system for gyms — those are real projects teams were working on. Why just for gyms or salons though? Why not try and build the best CRM possible that can also be used by salons. Because that’s more impressive. Optimize for the phatic side and try and impress everyone. I don’t know what the metric is but impressiveness is undervalued. Just seem really impressive. Usually people who are working on big problems seem impressive because it takes a kind of courage to be able to do that. It’s much easier to reach for the low hanging fruit.

There are a lot of important people there. The first time I did a startup weekend I didn’t know anybody. I didn’t even have a Linkedin let alone anybody to add as a connection. I grew up in a small town in Darwin and flew over to participate in it. Some of the people in the room ended up becoming mentors and advisers. Both times one of the judges was so impressed with us they offered us jobs. Another guy in the audience worked at a private equity firm offered to invest in us.

Nobody is really expecting anything from you. The consensus at most Startup Weekends is that it’s a bit of fun and whatever comes out of it is just a learning experience. Nobody expects the startups to go anywhere. They’re expecting everything to fail. Failure is not just tolerated, it’s encouraged. That’s a good thing because it means there’s no pressure.

It’s about finding talent. The hidden goal of Startup Weekends isn’t really about the startups, it’s about finding talent before it becomes talent. Think of it like magnetism, a Startup Weekend attracts people who have an inclination towards startups. Anecdotally people with an inclination towards startups tend to be talented since they recognise their ability to outperform market rates if they worked on their own thing, despite the inherent risk. That right there says something about the type of person who turns up to a Startup Weekend.

It’s humanising. Until that point I’d never actually met a venture capitalist or even an investor, I’d only read about them. One of the judges ran a $500 million dollar venture fund which seemed really scary. But after meeting him he just seemed like a person, if a bit arrogant. But it’s easier to identify and deal mentally with a self-absorbed person than a $500 million dollar scary venture capitalist. In fact, I was taller than him. Another judge was bald and they all seemed really old.

The end is just the beginning of the end. The end of the Weekend is actually just the beginning with the true results acting like a ripple effect and is only shown a few months after. A lot of the projects that seemed promising aren’t and some that did then don’t. For example both of the winners at the two startup weekends I’ve been to ended up dying shortly afterwards.

One of the apps that didn’t place made your friends look like they were pregnant by taking a picture of them and superimposing a pregnant belly. Sounds silly right? 6 months later it was number one in the Australian App Store for Entertainment. The biggest mistake is not working on their project further after the Startup Weekend ends, even on the side.

If everyone thinks you suck, you’re probably on to something. Anecdotally, the ideas that have the least number of votes in the voting phase end up creating the most value. That’s not to say every idea that doesn’t get any votes is good but usually the really good startup is present in that group since they are working on something no one realises is a good idea yet. All of the best startups I’ve met that come out of a Startup Weekend usually didn’t win and got barely any votes.

One company I know Tweaky got barely any votes, a year after the Startup Weekend they raised half a million dollars. Even personally, Medicine got zero votes. Tramsurance only got a couple and that exploded only a week after. The most popular ideas rarely end up being the valuable ones. In fact it’s probably an inverse relationship where the least popular ideas will be almost diamond in the rough like and be the best. So popularity is actually an unintentionally misleading metric.

Even if you lose, it doesn’t matter. Typically from every Startup Weekend I’ve been too, empirically the startup which wins is rarely the one which creates the most value tracked longitudinally over time. It’s one of the most baffling things I’ve ever seen because the judges are usually veteran entrepreneurs, angels or venture capitalists. So it’s like all the judges even though they are veterans are implicitly incorrect, repeatedly.

Even they can’t predict what’s going to work. It’s like a snapshot of venture financing as a natural phenomena. Nobody really knows what is going to happen until it does.