How To Win Startup Weekend, And How I’d Change It

Last weekend, I competed at Startup Weekend Ideas Week. The idea I pitched was something I’ve been thinking about for over a year, but I’m not here to talk about MergeNote. We (my team and I) didn’t win, but we did learn a lot, some of which I’ll share here. I also have some ideas for how Startup Weekend and events like it can improve. So, without further ado, let’s get to it.

How to Do Well at Startup Weekend

1. Leave your MBA at the door. — Please.

2. Drink 1 beer about 30 minutes before you pitch, consume 3/4 of another beer while waiting in line, and set the remainder of said beer down on the ground in front of you before you spit your game. — Trust me. It works. I don’t care how terrified of public speaking you are, a little liquid courage goes a long way. And on a similar note, you should gain an unfair advantage by being the only team to bring beer on Friday night. It’ll help you find developers.

3. Don’t be a “startup guy”. — Just don’t. If you’re going to be, please be as funny as these dudes. Do not take yourself too seriously; you’re just another person with a wild and crazy idea.

4. If you’re a business person, find developers. — If you’re a “business person” without a technical person working with you, you might have troubles finding developers who want to help build your idea, but if someone comes up to you and says, “Dude, I know exactly how this would work,” give her a hug and make her CTO for the weekend. For non-technical people, software programming seems like weird voodoo magic; developers seem to speak their own language, so it’s best to find an interpreter who can help you articulate your goals in a way you and the magicians building your thing can understand.

5. If you’re a developer, be flexible and pragmatic. — Don’t be the “I only do ASP.NET” guy. Find a team that speaks your language; do not insist on composing poetry, because you came to hack. Recycle. Steal stuff off GitHub. Whatever it takes! Know that whatever monstrosity your team cobbles together will misbehave and spit out nasty things and hog memory, and that—if you win—you’ll end up tossing the entire codebase and starting from scratch.

6. Don’t actually build your MVP. — This is the most controversial piece of advice I’ll give. This is how to hack Startup Weekend. Think about what it will take to win. Your team is going have to present your idea in front of a bunch of judges. So of course, build something beautiful. Instead of focusing your team’s technical resources on developing a shoddy but functional MVP, spend 30 minutes planning what you want to build, and instead of building out the back-end architecture, hack together a fantastic if largely non-functional demo. The judges will be looking at your thing for, what, like 75 seconds? Who cares if everything except for a few links is static HTML, open source JQuery plugins and PNGs? That’s right. Nobody.

7. Know how you’re going to build your MVP. — If anyone asks, you have to know how your thing is going to work, even if what you just demonstrated is only smoke and mirrors.

3 Ways I’d Change Startup Weekend & Related Events

I understand the whole ethic of Startup Weekend. People come. They pitch. Ideas develop into demos, and this takes place over the course of the weekend. But let’s be honest, some teams have been working together for months on something, and it’s unfortunate that judges vote down these startups. If I had to be honest with myself, this is why my team lost. Despite the fact that we’d talked about MergeNote for over six months, my technical cofounder and I never wrote a line of code for it until Startup Weekend. Perhaps something like Finish Weekend would be better for established teams like ours.

Give business people and developers a better “ratio” to work with. At Startup Weekend Ideas Week, about 50% of the attendees were registered “business people”. 40% were developers and 10% were designers. Here’s a modest proposal: make the business people apply with their ideas, and only accept a few of them. Make business people pay way more than the $35 I paid to go to SWIdeasWeek. Developers and designers get in free and are able to pitch their ideas without applying. The bottom line is, at these kinds of events, business people are largely useless.

There’s something about the startup culture that I think more people need to experience. Sure, business and design people get it: there’s a lot more freedom—creative and otherwise—afforded by startups. Most software developers I know understand this too; and we’re all getting a little tired of the somewhat incestuous (in a good way, I guess) nature of the Chicago startup scene. We want more developers! We want experienced developers! So, an immodest proposal: host hackathons, more Startup Weekend events, basically anything for developers who’ve worked in corporate for years and years to use as an excuse to let their hair down and be creative with their skills. I’ve met a lot of depressed 50-something developers who haven’t heard of Startup Weekend and haven’t been to a hackathon, ever. There’s a massive talent base out there who are doomed to toil away at jobs they can’t stand in some hideous, alienating corporate environment without ever building anything they care about. And this in my book is tragic. We as a startup community really need to reach out to them.

Jason Rowley

Jason D. Rowley does not like being wrong. He is a writer, startup founder, sometimes landscaper and gardner, and his library’s best customer. Jason is heavily involved with the entrepreneurship scene at the University of Chicago, where he studied political science before “taking a break” (e.g. dropping out, noncommittally) to work with his classmates on his current project, which will debut shortly. He’s written voluminous, ripsnorting articles for Flyover Geeks (now for over six months and publishes on Tuesdays. Edward Domain and others have described him as “obstreperous”, a label he wears with not inconsiderable pride. Jason, in spite of these claims, is a pretty nice guy.

What others say about : How To Win Startup Weekend, And How I’d Change It..

Jason D. Rowley

You should have seen me about 15 minutes before I pitched. I couldn’t get the first sentence out, and I was practicing with my co-founder, not in front of a group of strangers.

I was immensely surprised that I got my pitch out without error. I immediately walked back to the tower of beer we brought, smiled, and heard from my technical- and business-cofounders/friends say that “dude, it was the second beer.”

I’m sure I don’t have to extoll the functional benefits of having 1.75 drinks in you before one goes up to pitch, so I won’t. What I will say, though, is that it added an aura of nonchalance to our team, which is exactly the kind of atmosphere I/we wanted to promote on team MergeNote. 

Beer, in this case, served two purposes: it prevented me from fainting or shaking nervously, and it promoted a relaxed culture within our team. We did good work because of this atmosphere, and I’d drink to that.

Drew Gilliam

Spot-on Jason. I was in attendance and right out of the gate after pitching ran into a couple ‘MBA types’ that were shooting down ideas left and right by focusing on one flaw in the concept. I have an MBA and spent far too long doing consulting, but left all that at the door and just focused on having a fun time and meeting great people. That’s exactly the experience I left with because I was aiming toward learning something about working with folks in a unique environment.

One fine gentleman who’d never started anything in tech, told me that i had to be OK with signing an ownership agreement to join his team right out of the gate because he wasn’t there to make friends, he was there to get rich. Believe it or not, he was also a self-labled ‘idea guy’.

Sure, it’s possible that the next big thing could be waiting to come out at SW, but people need to realize that startups take practice and commitment, incredible amounts. The overnight success stories you hear are never ever just that, the person or people who have what it takes to successfully execute an idea, have been working on something for a long time that taught them what they needed to know. 

Congrats to the winning team BikeRecov, they are standup peeps and deserve what they got!

Jason D. Rowley

I have a rather passionate distaste for MBAs, especially at events like Startup Weekend. Attendees have to realize that Startup Weekend (and similar “sprint”-type build-something-in-a-weekend events–including hackathons, mind you) are not the kind of places where you “get rich”. 

Startup Weekend et al. function as a kind of proving ground for ideas, not a venue to sign papers on your Series A. Nor should there be an expectation that if you win SW, your team should launch the product that weekend. The guy who won last year is one of my best friends, and Cloudbot still hasn’t been released–one year after winning. You’d think that MBAs would understand the nuances of venue and context with these sorts of things, but based on your experience–and mine–I guess this isn’t the case (especially with the ones from Booth). (Not to denigrate Booth, by the way; it’s just that I found Booth people to be particularly, overly aggressive, given the type of event they were at.) I don’t know if we met, but I’m sure you’re an incredibly decent, upstanding guy… in spite of your degree. 🙂

J. Ky Marsh

Awesome article, agreed on almost every account. I also agree that there needs to be more incentive for developers to attend, and (potentially) LESS incentive for businesspeople to attend.

However, I don’t agree with this: “The bottom line is, at these kinds of events, business people are largely useless.” In my experience, at Startup Weekends, businesstypes rule. Their flashy presentations (and “plausible” revenue models) are what win the competitions, not working prototypes or demos. Hell, the last 2-3 SWs I’ve been to, the winning teams DIDN’T EVEN HAVE PROTOTYPES, working or non-working!

This most recent SW thankfully had a pretty good ratio of business-to-developer; much better than previous ones I’ve been to, anyway.

It’s funny, to me, because the businesstypes with their marketing lingo and Powerpoint presentations tend to be what win these competitions, and yet, without a solid team of developers, it doesn’t matter if they win, because they’ll never be able to produce their fucking product. Doesn’t seem like those judging the events have really grasped this, however…

Edward Domain

As a “business person” and startup serial entrepreneur, I think you guys have just had some bad experiences.

The yahoo that wanted you to sign ANYTHING should have been shunned immediately.  The MBA that shot down people’s ideas should also be avoided.

People that ‘get’ startups know this:

– If you ask a VC to sign a NDA, they’ll say, “Thanks for coming” and show you the door on your way out.  

– If you are too busy shooting down other people’s ideas, take a hike.

– Ideas are golden- but business people have every reason to be there as much as UI/UX guys.  I have a sales background and I have worked with people that have stellar ideas but aren’t so stellar at selling other people on them.  It takes a TEAM effort- its just that some people get confused on what constitutes a team.

So cut us “business people” a break.  We aren’t all bad 😉

Jason D. Rowley

I’m going to defend my claim that at Startup Weekend and related events, businesspeople are largely useless.

Sure, they come up with their graphs, use terms like “freemium” and “key functionality” in their Powerpoints, and pay the role of “team leader”, etc., but when it comes down to it, there’s not a whole lot that they do at Startup Weekends other than make things look and sound good.

If I were a business guy, with no technical background, with an idea to pitch, I’d do the following. Assuming I made it past the first cut, and found myself some eager developers, I’d immediately draw out my idea, and a list of features, and summarily appoint the smartest, most personable of the developers to lead the team in a brainstorming session to determine how to best execute the businessperson’s “vision”. From Friday night onward, I’d interface with my temporary CTO on issues like “I like this color,” and “I don’t like the name of that button.” I would leave well enough alone, realizing that my responsiblity is not to /manage/ my technical team, but to provide “leadership” and feedback. 

If you are familiar with “agile” methods, I’d take the role of the on-site customer with whom the agile team is in regular communication. My temporary CTO would be the product owner. At least, it should work out this way.

In my view, there should be some sort of requirement. If a SW team is pitching a technology product, there should be at least 1 technical person who’s considered a “cofounder” in order to be judged. 

– – – – –

Anecdotally: I love the other business guy our team found. He’s a talented and supremely excellent gentleman, but he maybe /worked/ for five hours over the course of the weekend. We’re a three-man team. There just wasn’t enough for the forth, new guy (a second business guy) to do–even taking into account the fact that my business-cofounder/friend had to take my role because I functioned as the team’s designer. 

A team (especially one working on a tech product) with any more than two businesspeople will not–or, rather, should not–do well. They’d be only getting ahead of themselves, worrying about things like revenue, and marketing and sales strategies before their product even goes online. It doesn’t matter how deep the market research is, or the elegance of the pricing model, business-y bloviating at Startup Weekend is an exercise in counting chickens before the eggs are even laid.


Jason, great post and great job at Startup Weekend. I’m glad we met. I had a great time at the event and couldn’t agree more with business types leaving their MBA’s at the door. That being said, I myself am a Booth MBA, but recognize that Startup Weekend isn’t the place to espouse MBA principles and talk through things. It is more a matter of actually figuring out what you want to accomplish over the weekend and then coding it all out and marketing it. Every non-technical person in our group was dedicated to marketing via Twitter, Facebook, and general mass emails (You probably got tired of all the Edit Huddle tweets). When the technical folks had a question, we provided some general guidance, but didn’t meddle. It is amazing how effective that was compared to doing a SWAT analysis on our business and micro-managing development. Also, it makes a world of difference when the “business guy” knows a little about coding. You don’t have to be an expert, but having a little knowledge goes a long way to making you a credible leader. 

I hope to see more articles from you and wish you all the best with MergeNote. Btw…you should try and convince to get Edit Huddle :) 

Imran Ahmad

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