How to actually win the award in a startup competition

You work really hard on your startup and sometimes it feels like there is no real upside to it and no appreciation for your dedication.

In the early days of a startup, any kind of social proof can help you to establish credibility within your industry, to hire staff, or even to try and raise funding from investors.

You know that there are start-up awards and winning one wouldn’t be quite so bad, would it?

The only real downside here is that, like anything in life, it involves time. So if you’re going to spend the time applying to an award process, wouldn’t it make sense to actually do it right and set yourself up to win?

I have had my fair share of experience judging startup competitions. Every year I judge at GSA, for example, which is one such startup award that services the Nordics, central and eastern European parts of Europe etc.

Every year the startup competition process is rather painful as I get dumped with about 60 startups, accelerators, or investors that I have to review for awards ranging from the best startup of the year, founder of the year, best accelerator, or even best angel investor.

This takes me a few hours to go through at warp speed levels.  I can promise you that I spend very little time really reviewing each and every application.

Furthermore, how the hell am I actually meant to know what the best accelerator is in the Nordics? I only know if they tell me and sell to me in the time that I will allocate and in the space that the organizer has provided them for me to read (if I read it all).

I got frustrated this year and thought do you know what, why not write a blog on how to actually make an application that judges might actually read and give yourself the best shot to win.

So many applicants are just terrible, so what you just need to be is the least terrible. I’m going to share how.

How the application works in a startup competition

I’ve never actually run an Awards process so I can only tell you what I observed from the outside.

1. They find you or you find them. Often the organizers go looking for startups
2. You get filtered as to whether or not to include you in a long list. There may be a quick interview
3. You get shortlisted and this is when you will need to start providing information about yourself for judges

Many awards have country-level awards, regional ones, and global ones.

You win the local one and you are automatically in the running for the regional one and so on, so you compete with the winners from each other region. The award progressively gets more prestigious, as frequently do the prizes. 

Why do you want to win a startup competition award?

Let’s cover this quickly, as it should be obvious:

1. Prize: Most awards give you a cash prize. You might also get AWS credits, which are like, tasty. I like free shizzle
2. Hiring: You can tell staff that you’re trying to recruit and that you are the winner of an award which is better than nothing if you’ve got nothing to sell otherwise
3. Team win: You need to celebrate small wins with the team to motivate them and help them to remember why they are sacrificing their social life to build your company. An award is a tangible win and something they can tell their mother as well as their friends
4. Ego: You need the win to keep motivated too!
5. Fundraising:  I think this is highly overrated as I frankly don’t really care about you being the award winner (given what I know), but some people might. it’s not going to get you the money, but frankly every little helps right? You might stick it somewhere on your pitch deck, maybe on the cover, and you have some aspect of social proof
6. Noticed: Investors sometimes go to the awards ceremonies so even if you’re just a candidate you are likely to get some sort of level of awareness from investors. If you win that goes doubly so. The more investors care about you, the more they think that you might be interesting
7. PR: Depends on how you’re able to sell it but it might be a way to help you get some press coverage from journalists

How Judges Read Applications

Now, this is going to be the insightful part that you’re not going to read anywhere else, as frankly, judges are never really going to talk about how a startup competition works behind the scenes, given they don’t care.

I’m going to explain to you how judges actually review award applications and how they pick the winners.

First, you need to understand that judges are busy and these award selections are something that they do because they’re probably friends with the organizer (Why I do it), or coming from a sense of giving to the community, rather than of any actual business value to them. They don’t really care who wins at all (so can be manipulated!).

For some award ceremonies, a judge might only have to judge one category which means they might spend a little more time looking at applications. Frequently, I find myself judging 4 to 8 different categories. Each category might have 10 startups in them which means that in total I might end up having to review 80 startups in one sitting. Yes, one sitting. I want to get this done and move on to real work.

The organizers send you an email with the link that you need to log in. Then there is a dashboard with the categories for judging and all the startups that you need to look at. You click on each startup link within a category and you can see information about them. There is then a rating system in which you judge applicants on a scale of 1 to 10, with 10 being the best. 

I always pick the first category and work my way down.

To acclimatize myself, I might quickly flick through each of the 10 applicants within a category to get a feel for what I’m getting and see any commonalities or main differences. I will then start at the top and work my way down through each application sequentially.

If the first one or two applications are pretty solid and I like the startups, I get more interested and am more inclined to want to actually read the applications properly. This is rarely the case though as most applications are just total garbage and I get annoyed that my time is being wasted. I remind myself that the founders are probably busy and filling out an application form is probably the last thing they want to do, but still, I wonder why the hell they are even bothering at all and do they really care or not.

If the information that the applicant has provided is generally garbage, there is no pitch deck attached, maybe there is a link to their website, but it’s in a foreign language, then I take a very dim view and basically just give them all a 2 and maybe a 3 rating. I rarely give a 1 to anyone unless they really have done a terrible job, but that is rare. That just seems to be mean I guess.

The first thing I look for is to see whether or not they have a pitch deck. I know that what people normally write on the text questions is total garbage, so if there is a pitch deck, that’s just the easiest way for me to see what the startup is about. That does, of course, assume that the pitch deck is not total rubbish. 

I generally find that if people include their pitch deck in an application process the people who do so have actually done quite a good job. I once saw an investor in the category of best investor in whatever region obviously write the presentation just for the application. I made him the winner because he looked like he was a professional and actually cared about it, so I let him have it.

If there is no pitch deck, then all I have to go with is to read the answers people have to the questions the organizers have set for the applicants. Mostly they are written terribly and are either copied and pasted from the website or clearly haphazardly pasted in just to get the application done. If I feel like the startup might be cool, then what I might do is quickly check on LinkedIn to see who the CEO is. If they look like they are actually pretty cool, then I might give them better rankings, but generally, these people are getting 2 and 3s just because I’m not going to spend any time trying to figure them out and so by default, they are going to lose.

It is not always obvious who the winners should be. What I generally do is figure out who sucks the least out of everyone and give them higher points than the other people. The grades people get are therefore not so much a reflection of their startup, it is just the perceived quality of the application. That’s nuts I know, but now you know!

Before I submit all my applications for a startup competition category I will review the dashboard for the points that I have assigned to the startups and make sure the relative points make sense. I will then press submit and move on to the next category, or get out of dodge and get back to work.

There is no real science in the rankings. Why might I pick 5 and not 6? There’s no reason. I typically change ratings on a relative basis between startups. So you might start with a higher number and then I find other better startups, so you go down and they go up. 

The secret to startup competitions is to suck the least

The big secret here that you want to take away is that you need to suck the least as you can set yourself up to be the winner, not on the merits of your startup, but that your application was simply better and easier to read than everyone else’s.

This is actually the exact same principle when you are doing demo day like presentations. The people that win are the people that were the least boring and suck the least!

I’m going to write a blog on how to do these too.

List of tips to set yourself up to win a startup award

Think like a judge in a startup competition

Something that I always try and teach founders and investors is to understand their intended audience and to think like them. There is no training course to be a VC or how to be a judge, so you can literally put on a hat and be able to think like one if you so choose.

The startup competition organizers email you and tell you that you need to fill out an application with a bunch of questions in there. You pause lean back look at the list of questions and think “Jesus Christ, do I really have to fill out all this rubbish!?”

No. No, you don’t actually.  Put on your judge hat and think like you are going to review this application for yourself. The reality is that the organizers don’t really know what the judges want to know, so they ask a bunch of random questions.

Think- if I was a judge, would I care about the answer to this question? If not, screw it. Less text is better. Alternatively, reframe the question in a way that you can sell yourself!

When it comes to questions such as the length of text that you want to include, think like a judge again and decide if you are going to spend a maximum of 5 minutes looking at your application. How much time would it take you to read that and would you care about anything that you’re writing it?

When you are thinking about what you should write, think about what a judge would want to know. No, they don’t care that you like doing cooking classes in your free time, they care that you are working on something really cool and are super passionate about it.

What would you want to see? Write that.

Be to the point

You have less than 5 minutes to say just enough to appear cooler than your competing candidates. Get to the point.

Apply whatever means to make your information easier to parse. 

• Don’t have long paragraphs
• Use bullet points everywhere that makes sense
• Use headers to break up any text if necessary. Use headers in your bullet points! 
• Bold important text
• Focus on numbers where you can. Support any points with data to be credible if you can

What would you rather read?

• 300 words of meandering text?
• 40 words in 4 bullet points that convey the same information?

In startup competition applications, read is better than perfect.

Don’t write essays

To emphasize the previous point, do not write an essay to any of the questions. 

It will not only take you a lot of time but also no one will read it. That sucks. 

Do the basics – grammar and spelling

I explained to you that most applications are rubbish. When faced with 10 rubbish applications, you will look for any excuse as a fall back to mark one applicant down over another.

Poor spelling and grammar are some of the easiest things to get right, but one of the obvious things to set you back.

If you are really busy, then write the general outline and then get an internal someone else on the team to proof it. If you have some smart kids in the team you can actually get them to draft the application for you and then you dig into it and improve it.

Sell

Always Be Selling! ABC.

Your application in a startup competition is literally a sales pitch, so treat it as such. 

The questions are there to help structure up the applications and to make them consistent across the board.

Your content does not have to be boilerplate blargh.

Use creative license to communicate why you are awesome and sell you. I wouldn’t say ‘be shameless’, but sell more than you normally do. Few applicants do.

Share your challenges

I know startup sucks and I don’t expect everything to go perfect. Sharing some challenges you are facing is actually a way to help me empathize with you and communicate that you are self-aware. 

I know this is a random point, but I remember one startup including 2 or 3 places they were still trying to figure out with the round they raised and I really liked it. It felt authentic and that the founder was actually sharing their startup.

Obviously, you don’t say you have a fecked cap table, but maybe that you are trying to bring your CAC down, or how to expand to other countries. 

I’ve never done this, but I’m the kind of person that would read an application and if I liked them and read they had some challenges I could help them with, I might actually reach out to them, or if I attended the award ceremony, I might seek to chat with them. 

Use USD $

It’s always a good idea to make $ or Euro your startup currency, regardless of the country you are in. 

I wrote a blog about this to explain why: Use dollars in your startup.

Especially if you are in a regional competition, there are going to be like 5 domestic currencies. I have no fecking clue what the conversion is for currencies in Bulgaria, Sweden, Latvia etc. 

If you fill in your application with Kroner, the only ones I will take note of are your metrics that have a “x” or “%” after them. I am NOT going to Google to convert Kroner into Dollars. I don’t have time for that. 

Everyone knows what a USD$ is. I guarantee it will make your numbers make so much more sense and, if applicable, impressive. 

This does not extend just to your text application, this includes any PDF pitch deck that you might include. 

Include your pitch deck as an attachment (PDF)

More than likely, it’s an investor who is judging the startup competition. Sure, there are corporate types too, but everyone can read a well-set-out pitch deck faster than reading a bunch of text.

If you don’t have a pitch deck and your text looks like a boilerplate, you will automatically get 2 and 3s.

You’re in an award process so no, you do not need to include anything super confidential. You do not have to include all your metrics if you don’t want to (though honestly, just do, no one really cares to share your shizzle, and even if they do, what can someone do with your metrics??).

Also, always use PDF when you share anything, not just for attachments in a startup competition application.

Provide key metrics

Provide key metrics such as the amount of revenue you generate, what your growth rates are, and the like. The exact number is not so important as is the order of magnitude. 

I just want to get an idea of what stage you are at. Are you doing $100k a year, or $5m? The time that it takes to get to those numbers matters too. The faster to get to those numbers the more impressive. 

If you write garbage but your numbers are great, they speak for themselves. 

Honestly, if you have great metrics and I’m in a rush, I might just make you the winner. Numbers talk, text walks.

Write in English!

For any award process, regardless of your country, you always want to write in English. I don’t care if you are from Latvia. The judges aren’t.

The reality is that in most countries there aren’t that many high-profile people around, so for prestige, the organizers will find judges from other countries (Don’t know why they mess up and keep finding me). Those judges speak English.

One company in my last process wrote their bio in Czech or something despite the questions being in English.

What score did you think that they got when I couldn’t read what they wrote? Yup, they lost me. 

Couldn’t I just Google Translate? Yes, but I don’t care enough to spend the time to do so. 

You should be picking up what you need to make the process for investors as easy as possible. Spoon feed them to win a startup competition. 

This founder clearly didn’t think about the audience and paid for it. 

Add a video 

This is such a huge win if you are capable of making a snappy video. Why?

• You made effort for this specific process
• You show yourself so I can relate to you (more than everyone else)
• It’s easier to watch a video than to read

If you don’t normally make videos, then do this. 

• You have an iPhone. Or someone on the team has a new one. The camera is solid
• Write a rough script of what you want to say
• Rehearse 5-10x so you can say it well
• Drink energy drinks, run around, whatever you need to do to get energy
• Bust out the phone and record a 30-second to 1.5 min video about your startup and why it’s so awesome!
• Send it to your computer by email
• Set up a YouTube account (if you don’t have one for your company)
• Upload the video. Set up a proper title (e.g. “GSA startup award intro to STARTUP” and write basic descriptions (Here is why we should win!)
• Set the video to “unlisted”. That way only people with the link can ever find it
• Include that video in the first question or company description with something like “We made this video just for the judges to explain what STARTUP does and why it’s so awesome! It’s only 1 minute long and will save you reading all the boring text! YTLINK”

If you have capabilities in-house, then you can do some fancy editing, etc, but honestly, if you are time-strapped, I would definitely appreciate you making the effort.

Little touches like you explaining the startup as you walk around the office and have your staff waving is cool. Maybe end with everyone on the team cheering together. 

I know it’s lame, but judges in a startup competition generally care about startups and this level of personality speaks so much more than boring text. 

Make it seem like you made a specific effort for this award

A lot of applicants will copy and paste guff from their website and try to get the application done ASAP.

I guarantee you they are going to lose. 

In at least one place, make a specific reference to the award you are applying to. It could be something as lame as ending your application with “here are the 5 reasons we believe you should give us all 10s and help us win the GSA award for ‘best startup’” then add 5 short bullets. 

Obviously, the video is the best example, but I know not everyone is comfortable doing that (Just do it!).

Communicate that you want to win the startup competition

So many people don’t make an effort. As a judge, I am far more likely to give the award to someone who actually wants it. 

So ask for it!

Mention the award in the copy, why you want to win it, and what it would mean to you.

If you don’t ask, you don’t get it. You have nothing to lose and everything to gain.

This is rubbish, but it could be something like “Our team are all underpaid and are killing themselves to make carrots as a service a reality. I’d love to go back to the office with the award for the best startup as it would mean so much to our team. Would love your support making this a reality. All 10s is an easy way to help us ;).”

Add judges for startup awards on LinkedIn and be nice

My final tip is more of a pro one which could backfire but could help a bit. 

I’ve had a few nominees for awards add me on LinkedIn with a message such as “Hey Alex- see you are a judge at GSA for our category. I would love to connect and appreciate the support! Hugs and kisses, Anton”.

Personally, I like the hustle. There are some people that might take umbrage with it though (who knows). 

It’s not going to guarantee a win, but it is unlikely going to be negative if you are cool and not annoying. The key is to be cool.

When I’m stuck deciding who to lend support to, something little like that could help sway me. 

Check who the judges are

I added this part after I posted this blog.

For the most part, you can tell who the judges are. On GSA you can go to the site and see.

You might not know who judges what, but that’s what spamming is for if you want to reach out to everyone.

Look at who is judging:

1. See how sophisticated they are to curate your information
2. What might they like to hear?
3. See if you have common connections
4. Maybe they are influential and can help beyond the award stuff?

Risky, but you could mention judges in your application. It could communicate you are an insider?

Personalization matters.

I have no idea why someone would win. That’s something you control, you just don’t know you can.

Conclusion on winning a startup competition

If you want to win a startup competition, take it seriously.

The people who win awards just do the basics right and make a tiny bit more effort.

Think like a judge and appeal to your audience. Bear in mind that you can check who the judges are sometimes by going to the award website and checking. 

Little things like making a video can really make an impact so long as your startup doesn’t suck. 

If you follow my tips I guarantee you will dramatically increase your chances of winning the startup competition.