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The Clowns Judging Startup Competitions

By In Startups

I often find myself on panels judging startup competitions for things like hackathons, Startup Weekends, Startup Bus, Startup etc. etc. etc. I love these things. The energy, passion, excitement, and cool stuff I see is inspiring. I end up back at the office on Monday feeling like I’m 22 again and ready for anything. But on that final day, that sweet kiss good night: the judging, if done poorly, can ruin the spirit of an entire event in the final pitches.

Startup competitions are not the same as real startups. Obviously. I do actually know a bit about real startups. I’ve started a few myself, invested in six or seven that have been successful, and sat on the board for dozens of others. After your first few, you start to get a feel for what you’re looking for. I also get a lot of in person pitches these days, something that is fairly new to me (mainly because having money is fairly new to me too!) In these pitches I look for the same couple of things that anyone else would: Market opportunity, team quality, competition, technology, and what else I could bring to the table (other than just cash.) But judging whether to invest in a company that someone has spent a year on is very different from judging a company built in a three days.

The problem is that a lot (but not all) startup competition judges I’ve sat with on panels don’t seem to know what they’re doing. I’ve seen a lot of arguments in the deliberation rooms between judges, often slinging their egos around more than their expertise. Sitting on a tech startup judging panel with “pillars of the community” who know sweet-all about technology is often an exercise in futility. So I figured I’d rant a little about what I see people do wrong, and then offer some suggestions.

Judging Startup Competitions: The Clowns

Show Offs

Every competition I see judges trying to show off how much they know. Being a judge is an honor, I get it. It’s also fun. But that doesn’t mean that you have to start every sentence with “Well, I’ve actually done this exact thing before, and let me tell you what I know…” We all know you’re awesome; we read your bio on the competition’s page. Nice 80’s headshot by the way. Now show a bit of class and let the stars of the show be the ones who did the work. You’re not Gordon Ramsay, and no one thinks you’re cool because you’re so tough.

Know Nothings

If you don’t understand how something works, it’s fine to ask. Not everyone is going to be there because they’re a techie, and there is clear value in a multitude of expertise. If a competitor missed a crucial point in their pitch, it is totally fair game to prod. However, you need to listen. I cannot tell you how many times some teenager has pitched something pretty cool, and heard a judge ask them a question that was directly addressed in the presentation. We know you’re a big deal, but stop reading your American Express wine club email, and listen to the poor kid who hasn’t slept in three days for your entertainment.

Bad Advisors

Some salient advise is highly recommended. But a lot of what I hear is asinine. I’ve heard judges tell pitchers that they should dress better, or stand up straighter, or that they need a better logo. Seriously? This isn’t pitch practice – stop focusing on trappings. Let’s see YOU build something worthy of showing in a few days, built with a team of strangers, with no pitch coaching, and then let me criticize your pronunciation. Remember, these people aren’t asking for your money. They want to learn how to do this. Point out positives, approach glaring negatives with a bit of grace. Be someone to be looked up to, and don’t be a bully.

Financial Nit-Pickery

This one I just don’t get. In most of these competitions you’re dealing with people who are just dipping their toe into the entrepreneurial pool. The last thing they need is some slick-haired jerk, telling them their model doesn’t accurately take into account carried interest. I know you’ve gone to the trouble of wearing a suit to a college auditorium on a Sunday, but try and inspire people for Steve’s sake. Obviously this depends on the type of competition. If it’s a six day event, and “business people” are involved, you should expect nonsensical spreadsheets, but you wouldn’t take them seriously without doing the math yourself in a real startup, why would you in pretend one?

Big Boy Comparers

If I hear one more startup judge ask “What happens if Google decides to compete with you?” I’m going to tear up their Louis-Vuitton padfolio. The answer to this question is “What would YOU do if Google started competing against YOUR business?” Maybe don’t be that harsh, but the point is valid. The whole idea of a startup is to do something new, interesting, and competitive, with little to no resources. Microsoft don’t want to launch a tiny experimental company to see if it works – their margins need to work at their scale TOMORROW; not build a market over a few years. This is why big companies wait a while, see if something is successful, and then just buy the startups rather than gambling on their own.

Reality Checkers

Ah, my favorites. These are the wombats that assume that everything done in a competition needs to have an immediate value to the real world. This might be partly the fault of the competition’s organizers not setting expectations. Not all hackathons or startup competitions are actually about building real companies. The participants are not looking for investment (although they might think they are.) These are safe places to learn about how passion, teamwork, and resourcefulness can produce something beautiful in a short period of time. It gives newbies a way to gain insight into the startup process without the risk. Would you take your actual billion dollar idea to a Startup Weekend because you want to find a team of co-founders? That would be like using Tinder to find a house keeper. Give credit to a team trying something interesting. If it’s a non-profit, be happy. If it’s just fun and clever, that’s OK too. This isn’t Shark Tank. You’re not Mark Cuban.

Judging Startup Competitions: What to do

So now that I’ve told you what NOT to do when judging startup competitions, let’s look at some things that you should do.

Stick to the criteria

Often competitions have a theme or several judging criteria. Use these honestly, but don’t take them as gospel. You don’t have to give first place to the healthcare game if the theme was medical devices, but if it was really good, take that into account.

Be honest, but don’t be mean

You are a judging a startup competitions for a reason. Someone has to win. That doesn’t mean you have to crush someone’s dreams. Preparing them for “the real world” is the job you take if you are going to put your money where you mouth is, and invest. If the idea is terrible, you can simply say “Thank you” and then ask some questions that will show them the shortcomings. Let them work it out for themselves, or talk to them privately after the competition. You don’t have to tell them they’re going to die poor an alone, or publicly humiliate a junior school music teacher for trying something new.

Keep in mind the time frame

“This is incredible given your time constraints” is one of the nicest things you can hear from a judge. If you really are worthy of being a judge, you should have some concept of the level of effort that went into building something (unless you were brought in as the finance guy, and then the organizers made a mistake.) Don’t expect to see a startup with enterprise customers if they just launched earlier that Sunday.

Judge what has been built

Try and focus on what you can see. Usually this means the demo. There are competitions where the final product is the pitch itself, but I don’t get invited to those.

Judge the team effort

Keep in mind that most of these people only met each other a few days before the pitch. If things seem a little disjointed, that’s because they are. This is most likely the last time any of them will ever see each other. If you see a particularly strong team, give them some credit.

Be weary of pre-built teams

As a counter to the last point, know that any team that came in together. If they’ve worked on their idea outside of the competition that is called “cheating”. At the very least, it’s not fair to the rest of the teams who signed up to learn something new. My immediate reaction is to give them an honorable mention, and then go and talk to them afterwards if the idea is really good (daddy still needs companies to invest in.)

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I help companies turn their technical ideas into reality.

CEO @Sourcetoad and @OnDeck

Founder of Thankscrate and Data and Sons

Author of Herding Cats and Coders

Fan of judo, squash, whiskey, aggressive inline, and temperamental British sports cars.

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The Product Is Bait

In Entrepreneurship, Startups

You Don’t Know Yet

Founders don’t know what problem they’re solving yet, and neither do any of their customers, and the annoying part is that this is not actually bad news, because if you stay in it long enough, you will eventually figure it out.

The Product Is Bait

The way it usually goes is this: You build something that takes a particular angle on a particular problem in a particular industry (probably one you know pretty well, or think you do), and one of two things happens. You either get sucked into a kind of product development haunted house where it has to be just a little more complete before it’s ready, and the dashboard needs better onboarding, and what if it had a Slack integration, and maybe the logo should feel more “enterprise” (I have never once heard a satisfying definition of what “enterprise” means as an aesthetic), or you get a version out the door and into the actual market, where it doesn’t sell. Not selling is, counterintuitively, on ok outcome. It won’t feel good, it’ll feel like capitalism personally singled you out for a lesson, but what you have now is a real artifact that maybe 1% of your original intended market can react to, and that 1% is enormously valuable because real reactions are the only raw material that matters. You can now take that product (which is bait, more than anything else) and you start showing it to ten, twenty, thirty potential customers, watching their faces and listening to what they complain about.

Feature-Requested to Death

At first, they will try to feature-request you to death. These requests will feel very convincing because customers say things like “if it could just hook up to our QuickBooks instance, I’d buy it tomorrow” or “if the AI could handle this last piece of the workflow, this would be an absolute game-changer for us” (they will ALWAYS ask if it can export to Excel, a request I believe predates the spreadsheet and may outlast the species). So you go back to your team, you build as fast as you can, you ship version two with all the new features, you go back to those same customers, and if you are good, AND lucky they will tell you the exact same thing: there are just one or two more features they really need, and then this thing will fix the problem once and for all, and you are almost there.

The Roadmap Graveyard

I’m going to pause the loop here because it can go on for twenty iterations (and I’ve seen it go longer). The real tragedy is that a lot of founders never even get this far, because their demo customers have them trapped in feature-development purgatory forever… or their own brains trap them there, because the product has to be perfect before any real human is allowed to see it. Those products die in roadmaps and “just one more thing” conversations, and never get rejected by the market because they never actually reach it.

Eventually, You Start Seeing the Elephant

But if you can stay in the conversation long enough, past the feature requests and the individual customers and the literal words people are saying to you, something strange starts to happen. You become, through sheer accumulated exposure, the world’s leading expert on the problem your customers all have in common. Not the problem you thought you were solving when you started, and not the problem any one of them has described to you, but the actual structural problem that everyone is bumping into from different directions (Schlep Blindess) without being able to name it, because nobody has a view of the whole thing. One customer tells you it’s the accounting system. Another says it’s logistics. A third says the two systems don’t talk to each other. A fourth blames someone named Susan in operations (this may or may not be fair to Susan… but yeah, wtf Susan?) Each of them is holding a piece of the elephant, the trunk or the tail or the foot, and describing it with complete sincerity, and they are all correct about their piece, and none of them can see the animal.

You, Neo, Are The One!

You are the only person who has talked to all of them, which means you are the only person positioned to eventually see the whole thing. The insight doesn’t come in a meeting and it doesn’t come from a good customer interview; it comes sideways, usually while you’re not looking for it. You’re at lunch with a client and one of their direct reports walks in with a quick question, and two people start having a conversation right in front of you, and the boss asks why the system can’t do something, and the user explains the workaround, and a third person adds “we only do it that way because finance needs the numbers by Thursday,” and a piece clicks, and then another, and then another. You suddenly understand that the product you built wasn’t the product at all; it was the thing that got you close enough to understand what the actual product should be, which turns out to be a considerably more interesting thing to build.

Earning the Right to Understand

The first version won’t be right, and the second version probably won’t be right either, and that is not failure… that is the process of earning the right to understand what you’re actually building (see Paul Graham’s “How to Get Startup Ideas“). Most founders want to skip straight to the insight, want the clean customer discovery process and the tidy MVP and the market telling them in bullet points exactly what to build, and that is just not how it works. You build the wrong thing, you launch it, you survive, you talk to as many customers as you can stand, you resist becoming a short-order cook for every prospect with a credit card, and you keep looking for the pattern underneath all the noise until eventually you see the elephant.

That’s when the real company starts.