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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. Author of Herding Cats and Coders. Fan of squash, whiskey, aggressive inline, and temperamental British sports cars.

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Don’t Fall Into the Trap: Why Startup Software Development Isn’t Like Corporate Development

In Startups, Technology

So, you’ve left the corporate world, and now it’s time to build your own startup. You’ve probably managed dev teams before, overseen product launches, maybe even helmed some fancy project management tools that made everything run like a well-oiled machine. You’ve done this before, right? Not exactly. When it’s your startup, everything changes—and, as I’ll explain, if you assume it’ll work the same way, you’re heading for a few surprises.

Startup founders often fall into a dangerous trap when starting a software project from scratch: thinking it’ll be just like building software inside an established company. Here’s why it’s not—and some advice on how to navigate the differences.

1. Switching from Product Manager to Teacher

In an established company, a software team already has two things that give them a serious edge: an existing market and a deep understanding of the business. They’re working within a proven model. Developers in that environment know what questions to ask, can fill in gaps intuitively, and likely understand why they’re building what they’re building.

At a startup, however, your devs are going to need a whole lot more context. They’re not working with familiar requirements—they’re working with your vision, which may be abstract at this stage. If your development team doesn’t understand why something matters, it’s a recipe for ambiguity and frustration on both sides.

Advice: Think of yourself less as a product manager and more as a teacher. Your job is to make sure they understand the core problems, not just the features. Teach them why each requirement matters, help them visualize the end-user, and create that shared language for decision-making. It might feel tedious, but it’s essential to avoid future misalignment and expensive rewrites.

2. Beware of Perfectionism — It’s the Budget Killer

In a large company, products with an existing user base often have to be polished. Features need to be rock-solid, invoices have to be perfect, and everything needs an audit trail. Startups, however, have a different goal: get an MVP in the hands of users fast. It’s a classic trap for first-time founders—focusing on “perfection” and “polish” before knowing if the business model even works.

Startup perfectionism is budget poison. It’s shocking how quickly adding “nice-to-have” features can chew through funding, especially if you’re paying a dev team to build things like automated invoicing or churn management before you’ve even proven people want what you’re selling.

Advice: Ruthlessly strip down your MVP. If a feature doesn’t help you validate your market, it goes on the “later” list. Keep the scope laser-focused on what helps you test your business assumptions. Let the non-essential features wait until you know you have customers who’ll use them.

3. Zen and the Art of the Startup Pivot

Building software for a startup means embracing one cold, hard truth: the business model will change. According to research, 93% of successful startups pivot at least once (and often more). Imagine being asked to go out and passionately sell something that you know might not look the same next year—or next month. It takes a level of zen acceptance that your original idea will likely morph, but that’s what keeps you flexible and ready to capture new opportunities.

For founders, that requires a mindset shift. You have to believe in your product, while also knowing you might be building the “wrong thing” in some way. The focus should be on preserving capital and brainpower for what’s next. The game is less about proving you’re right and more about staying adaptable.

Advice: Budget with pivots in mind. Set your burn rate assuming you’ll need to make big changes. Don’t let ego get in the way of listening to the market, and keep enough gas in the tank for at least one big strategic turn.

4. The Hard Work of Being Your Own “Internal Customer”

Here’s another big one. In a corporate environment, you have internal customers—departments or stakeholders with specific goals that align with the overall company mission. For a startup, the only customer you have is you. You don’t have a preexisting feedback loop from various departments, and you don’t have established success metrics. You have to create that from scratch.

Advice: Start by building an internal customer profile based on your target market, then use that to set clear goals and success criteria for your dev team. If you’re focused on, say, usability for early adopters, set KPIs around usability testing and build from there. By acting as your own “internal customer,” you’re setting a clear direction and saving your team from working in a vacuum.

5. Get Ready to Build AND Sell

Corporate software development often has the luxury of a separate, dedicated sales team to deliver the product to the right audience. As a startup founder, you’re both the builder and the seller. That means you’re not just iterating on software—you’re iterating on messaging, product-market fit, pricing, and maybe even distribution models.

Advice: Factor in time for sales-ready iteration in your dev cycle. As you build, keep track of how each release or update affects the user experience. Ask yourself if the changes make your pitch clearer or simpler and how they align with the current market’s needs. Ultimately, this approach will help you bridge the gap between building the product and ensuring it’s market-ready.

Conclusion

Building software as a startup founder requires a whole different toolkit than you may be used to. You’re part-teacher, part-salesperson, part-zen master, and always the chief budget officer. By recognizing the unique mindset shifts and traps of startup software development, you’re positioning yourself—and your team—for the best chance of success. Focus on creating clarity for your team, set ruthless priorities, embrace change, and never lose sight of the fact that the first version is just the beginning. In the startup world, adaptability isn’t just a skill—it’s the entire game.