How to Win Startup Weekend: A Hustler’s Guide

If you’ve ever been to a Startup Weekend, then you’ll know that it’s more about learning the Lean Startup Methodology and testing those business ideas that you’ve been sitting on and telling your friends about for far too long. But, I’m a competitive guy, and after my first time at Startup Weekend Perth, I developed a strategy that helped me win the next time I went.

With another #SWPerth just finished this past weekend, I thought I’d share my strategy.

App to manage crowdfunding supporters wins Startup Weekend Perth

About Startup Weekend

Just in case you haven’t been, Startup Weekend is a 54 hour competition where you pitch an idea to strangers and form teams on Friday night, and then (hopefully) have a validated business model, completed MVP and paying customers by Sunday night. It’s mentally and physically exhausting, but it’s also a lot of fun, and a great way to meet some really talented people.

At my first Startup Weekend, I went along with a pretty good understanding of the lean startup methodology, and thought I had a great idea worth pursuing (Addicted2Learning — using addictive gameplay elements to make kids smarter). I managed to form a team, but we never really made much progress, and I took away a lot of lessons which I applied the next time around.

Before The Event

The most important thing to know about Startup Weekend is that you need to bring an undeveloped idea. That means you can’t have any code written, you can’t have started to build a social following, or otherwise started to build your idea prior to the event. But there are still some things you can do, and should do, that will help you out on the weekend and that are still in the spirit of the event.

1. Read The Lean Startup by Eric Ries

If you haven’t read it, then you really should check out The Lean Startup by Eric Ries, as many of the principles and methodologies that are utilised over the weekend are inspired by this book. At the least, you should go check out the Wikipedia page on Lean Startup so that you understand the core concepts and definitions, or watch one of the hour-long videos on youtube.

2. Have a rough idea of your business model

If you’re going to be pitching an idea, then you should have a basic understanding of how that idea can be turned into a real business. Go grab a copy of the Business Model Canvas by Strategyzer and start to think about who your customers are, what value your business offers them, and how you’re going to make money. You’ll develop this further with your team on the weekend, but the idea is that you should have a basic understanding of the business model behind your idea, if you’re going to pitch it.

Use the Canvas.

3. Do your research

This is one area where I think a lot of people fall down. If you’re going to pitch your idea, then you need to know:

  • Who your competitors are. I don’t know why this needs to be said, but I see so many people that come in and pitch an idea that’s already been done by 10,000 other people. An example from this past weekend was an app for finding food trucks — it took me three seconds on the app store to find two other food truck apps servicing our local area. Pitching an idea that’s already been done is fine, because I think execution can beat uniqueness, but the important thing is that these people often have no idea their competitors exist, or think they can ‘do it better’ without really having an idea of how. Google: Use it.
  • Strategies used by similar companies — in this day and age, startups have realised that sharing their strategies is great for marketing, and so there are some great resources out there on how to do things. Eg, when we were launching a subscription box service at another SWPerth, we heavily referenced WetShaveClub’s Reddit Post about the inner workings of a subscription box company.
  • Know who your key influencers are. Who are the key people that can help you get the word out about your business idea? Eg, if you’re pitching an idea for a monthly box of sundries for AirBnB hosts, you should know who the biggest blogger/youtuber that talks about making money through AirBnB is and have some vague idea of how you can contact them.

Friday Night — Building Your Team

The day has come! You got your early bird ticket the moment they went on sale, you’ve packed your energy drink of choice and you’re ready to crush it! But first, you have to pitch and build an awesome team that’s going to be able to execute on your idea. Here’s your strategy for Friday night:

Get to know your fellow participants

Startup Weekend typically divides its participants up into three categories: Designer, Developer or Hustler (sometimes called Non-Technical). I mostly consider myself non-technical these days, though inevitably I end up doing some sort of coding/tech work.

Designers these are rare as hens’ teeth at Startup Weekend, and getting a good designer on your team can make a huge difference in your ability to win the competition. Remember, as long as it looks pretty, people will forgive your weekend MVP not working properly (or being at all functional) — after all, it was only built in a weekend!

Developers — If you’re not one, and you need one, then you’re going to have to get one on your team or your idea is going nowhere. Developers are not quite as rare as designers, but in my experience most of the developers that gravitate towards the startup scene have their own ideas that they want to explore, and are not as interested in building out yours (which is quite reasonable). It’s important to note that developers come in different flavours — some are good at mobile apps, some are good at web applications; some are front-end, some are back-end. It’s up to you to know which sort of developer your MVP needs.

Non-Technical — The third category of participant is generally a bit of a catch all for people that aren’t developers or designers, and usually meet one or more of these descriptions:

  • People who are just along for the learning experience. These people are generally quite new to the startup scene, so don’t expect too much from them except an open mind, and a willingness to do things they wouldn’t normally do. They can be great for research and customer validation, and sometimes they also just have general business acumen that can really benefit your team.
  • People with an idea, which they desperately want someone else to build, but who have no real discernible business skills that would actually make the business a success. These people are generally anchors, and you want to avoid them. They’re often married to their idea, and won’t change anything about it even when everything points to the fact that they’re wrong.
  • Crazy people. These’s always a few at each Startup Weekend. My most memorable is the one who “used to go hang-gliding with Bill Gates”, but needed to be walked through how to use Google. I guess they were more of a Bing person.
  • Subject Matter Experts. These participants can be hit or miss in terms of how applicable their skills are to your startup. An accountant co-founder can be extremely valuable long-term, but think about where they will add most value over the weekend. At the most recent Startup Weekend, we had an arborist (tree cutter-downer) pitch his idea for a platform that connects arborists with gardeners, to dispose of excess mulch which they otherwise had to pay to dump. He had a supply of mulch, he knew other arborists that he could sign up over the weekend — he just needed someone to build the platform and help with customer acquisition. By Sunday they’d sold over $600 of mulch.
  • People with applicable business skills. If you’re lucky, you’ll end up with someone who knows about online marketing, social media, or wordpress, but sometimes you’ll find people who know how to pitch or to lead a team. For example, I met a non-technical participant on a team last weekend who was the Managing Director of an oil & gas company and had great presence and leadership skills that added a lot of value to the team. During the final pitches, he was able to provide really thoughtful answers to the judges’ questions.
  • Hustlers. Probably one of the most useful class of non-technical participant at Startup Weekend are the real hustlers. The people who aren’t developers, but they can pitch a product, develop a customer acquisition strategy, build a social media presence in 24 hours, craft a Google Adwords campaign, setup a landing page or develop a launch strategy all without breaking a sweat. If you find one, latch on and don’t let go

Before the pitch: Build your team

Make sure you arrive early and sign in , then grab yourself a drink and keep an eye on people as they come in. See a designer or developer? Make sure you go introduce yourself — “Are you pitching an idea tonight?” is a great conversation starter, and also gives a great opportunity for you to practise your pitch when they ask “How about you?”.

By the time you get to the event, you should have a bit of an elevator pitch, and an understanding of what sort of people your business will need to get off the ground. Prior to the pitches, you really want to find these people and get them excited about your idea. At this point you’re not really doing a hard sell, just giving people a bit of a teaser for the idea, your background, and what they might get out of being on your team. Remember, never tell people you need them, tell them why it’d be great for them if they joined your startup (be a value-giver, not a value-taker).

The Pitch: Sell yourself and your idea

The Friday night pitch is a one minute opportunity for you to get up and convince people to rally behind your idea. The whole purpose of the pitch is to get people interested in your idea, so they come talk to you after and join your team. If you don’t form a team, your idea won’t make it past Friday night.

Your pitch should generally follow this format:

  • Hi, My name is _____ and I’m here today to invite you to join me in <business name> that <main value prop>.
  • My background is in <relevant background> and I’ve seen a problem/opportunity where <problem/opportunity>
  • I think we can solve this by <how you do it>.
  • I need <mobile app developer / web developer / UX designer /etc.>

Remember, you only get 1 minute and people will begin clapping you off the stage at the one minute mark. Be concise, and be compelling.

After the Pitch: The Hustle Begins

I believe some Startup Weekends do this a bit differently, but at #SWPerth, after your pitch you head off to the side, make a poster with your team name on it and stick it somewhere on a wall. When all the pitches are done, participants go around talking to everyone that pitched, putting stickers on interesting projects and deciding which team to join.

For your idea, this is the most crucial part of the weekend, for two reasons:

  1. If you don’t get team members for your idea, you will have to kill your idea and join someone else’s team.
  2. If you don’t get the right team members now, you won’t win.
“Stickers are a vanity metric”

When you create your poster, keep it simple. Put the name of your team in big bold letters, with the tagline below. Then place that poster in a central location that every body will have to walk past.

When the pitches are done, make sure you grab 1–2 people who seemed really into your idea. They may come up to you while the other pitches are still on, or you may have identified them before you gave your formal pitch. Regardless, get their acknowledgement that they’re on the team, and instead of just having them stick a sticker on your poster, have them write their name. Stickers are a vanity metric, because often people will stick a sticker and that’s the last you see of them.

Once those people are locked in, just keep hustling. The idea is to build a team of people that really get the idea, and who have the skills which can make it happen. Ideal team size is probably 6 people — anything over 4 is sufficient, but once you get over 8 members it becomes difficult to manage. We once had a team with 11 participants and had to split ourselves in two working groups to keep things sane.

If you can’t build a team around your idea, don’t worry too much about it. There are a lot of ideas pitched and not every one of them can turn into a startup, but that doesn’t mean the event is over for you. If it looks like your team isn’t forming, go join a team that you think you can add value to and resolve to do better next Startup Weekend. And remember to have some fun.

On the other hand, if you have formed a team, great job! It’s time to launch that business!

Friday Night Goals

By the time you’ve pitched and created your team, it’s usually getting quite late and we often get kicked out of the co-working space around midnight on Friday. In the few hours you have remaining to you, make sure that you:

  1. Quickly do introductions amongst your team, and sort out roles
  2. Quickly revise your business model canvas, with new input from your team
  3. Register a domain and setup a landing page with an e-mail capture
  4. Work out what your MVP is going to look like

This is a pretty demanding schedule, but you’re pretty limited for time at Startup Weekend, so the more you can do in the first night, the better off you will be for the rest of the weekend.

Items 3 and 4 are particularly important, as Saturday is going to be spent building, and marketing, and you want to be getting straight into it from the moment you arrive.

For all of the above, I highly recommend that you use something like the Magnetic Boards by Tesla Amazing, or one of the many equivalent products, to do the planning. They’re static-adhesive whiteboard sheets that stick to any surface and work great at an event like Startup Weekend where whiteboards are at a premium.

Saturday — Build it and Sell it

I’m not going to say much about Saturday, except to say that your objective is to build the MVP, and to sell it.

I typically split the team into two groups — builders and sellers. The builders are the developers who are putting together the MVP, and really need to be outcome-focused (don’t get hung up on details). The sellers are those that are out chasing customers down, whether that be in-person or online. If you have a designer, they’ll tend to float between both.

Event organisers typically recommend that you use surveys to get customer validation. I personally feel that the only real validation is when someone is prepared to open their wallet for you. You know who your customers are (because you did your business model canvas), now go and find them and sell them something. Don’t forget to ring a bell or cheer really loudly when you make your first sale, as it’s important to psych out other teams competing against you.

The other thing that generally gets recommended at Startup Weekend is to go out onto the street and talk to people. I think this is a bit of a misinterpretation of the “get away from the product” idea. Going out onto the street and talking to people is fine if your customers are outside on the street, but that’s not always the case.

When we were selling “Quokka Selfie Sticks”, it was easy to find potential buyers on the street, but when we were working on an app to help crowdfunders manage their backers, the chances of us finding a Kickstarter project creator in downtown Perth on a Saturday were pretty slim. Instead, we contacted project creators from projects we’d backed on Kickstarter or spoke to other project creators in the Kickstarter Best Practices group on Facebook.

Go outside and talk to your customers — but only if your customers are outside

Now, in some cases direct sales won’t suit. So focus on metrics that matter.

  • Eg, If your customers are Kickstarter project creators, talk to projects that are currently active or who have already funded. Get them to agree conceptually that they will go on your platform.
  • Eg, If you’re building a free social app, you want to onboard as many people as possible so that you have a core audience to talk about, and show that they’re using the network — 100 users with 1,000 posts is great validation! If it’s a freemium model, you want to find out how many people convert.

Sunday — The Pitch

By Sunday morning, you’ve built your MVP and pivoted or revised it based on customer feedback. You’ve sold to your first customers, and validated the business model. You’ve growth-hacked your way to 1000 followers on social media and have collected 500 e-mail addresses through your landing page. On sunday you keep selling and refining, but really it comes down to the pitch.

Understanding the Judging

At Startup Weekend, they talk about a few different criteria that they use for judging, but I like to focus on 3 things:

  • Is it Pretty?
    Have you created something that looks impressive? Your powerpoint deck needs to contain well-branded slides. Photos of your UI need to look impressive. If you haven’t got a designer, there are a plethora of free resources online. There are no excuses for an ugly presentation.
  • Does it work?
    The judges want to see that you’re able to execute. That you can talk about building something, and that you can actually do it. That said, I would argue that this is the least important of the three, as judges understand it takes time to build out a fully working product. They just want to know that you know what the final product will look like, and that you have the capability/understanding to do it.
  • Can you sell it?
    I would argue that this is the most important aspect of the three key judging elements. Startup Weekend is all about validation, so if you can show a solid customer acquisition strategy, and how you’ll grow your offering inside the market, then you’re doing well. If you can show some validation of your ability to execute on that strategy, you’re golden. For example, in our winning pitch related to the crowdfunding app, we showed the total funds raised for all of the Kickstarter project creators we spoke to, who had provided quotes to us about their agreement with the problem we solved.

Things not to focus on

You only get five minutes to present your startup at the end of Startup Weekend and there are a few things people tend to waste a lot of time on, that I think need to be addressed:

  1. The size of the market. “If we just got 1% of 1% of this 10 bazillion dollar market…” — if your pitch contains this, you won’t win. Generally speaking, you shouldn’t have to explain that your market is big. It should be immediately obvious. Eg, smart phone users. Do I really need to tell you this is a big market? The only time you’d really need to do this is if it’s a surprisingly large industry. Like, let’s say that professional snail racing was a $200 billion dollar industry — but even then, what’s more important is how you intend on getting a piece of it.
  2. The team. A controversial thing to say perhaps, but I include this because sometimes people spend half their time talking about their team. Very quickly, 10 seconds, “This is our team of x people. As you can see, we have skills covering SEO, software development, financing and our subject matter”. Even better, introduce them at the end during question time.
  3. Tech Demo. You don’t have time to minimise powerpoint, bring up your website and demonstrate a typical user experience. Take screenshots and dump them in your deck. If it works, great, tell them — they may ask to see a quick demo during the question time.
  4. Validation fails and pivots. Remember, you’re not pitching your Startup Weekend journey, you’re pitching the business that you’ve finished on. Don’t focus on your failures, instead focus on the awesome business you’ve created.

The Pitch Deck

I generally refer people to the Pollenizer Universal Pitch Deck as a guide for the order of your slides, but I break the format a little bit myself when I’m pitching:

  1. Background & Problem: If you have a ‘nightmare’ that you experienced, and this project solves that nightmare, talk about it. I also like to rename this slide ‘opportunity’, because I feel that not every good business idea is a problem waiting to be solved. Sometimes you just see a nice market gap, like a health supplement aimed directly at people in the startup community.
  2. Solution: Walk us through your solution to the problem. What’s unique about it and why should people care? What’s the compelling sales motivation?
  3. Validation: Is this a real problem for customers? What did they think of your solution? Did you sell to anyone? If not, you better have spoken to some potential customers that had a pretty high potential spend. Talk about your social media followers and the e-mails you’ve captured if you want, but at the end of the day sales trump everything.
  4. Walk Through: Give a brief walk-through of your solution — how the process works, what the UI looks like. This gives the judges a deeper feel for why the customers are willing to buy.
  5. Client Acquisition: How have you gotten customers so far? What is your unique method for getting people to sign up? Are you doing things that don’t scale? That’s okay, but what’s your long-term strategy? Is there a cost associated with acquiring each customer? If so, find out how much.
  6. Revenue Model: What’s your billing model? Do you charge per signup? Freemium? One off payment? Subscription-based? Make sure this shows how you can actually make real money. This past weekend a team of 8 people pitched that they could earn $120k/year if they cornered the market. Don’t be those guys.
  7. Growth Plan: You solve a real problem with a solution that customers want, and you’ve shown you know how to acquire a few customers to make money from them. How do you grow the business? Do you expand horizontally or vertically? Is your potential customer base growing? How do you automate some of the things you’re currently doing manually? In other words, how do you scale this company for hockey stick growth? For example, our food truck app discussed expanding into other states vs expanding to pop-up food stalls at local farmers markets, or including ice cream trucks and coffee mobiles in their model.
  8. The Last Slide. The last slide is a great place to put up information on your team — photos, names and title/background, as well as any call to action that you might have for participants in the crowd. We throw this up as we finish and leave it up while questions are asked.

Importantly, each slide should only have 3–4 dot points with no more than 5–6 words per dot point. Your slides are only there to prompt you, and to give the audience a quick idea of what each slide is about. If you haven’t watched Guy Kawasaki’s video on the 10/20/30 rule of presentations, you should. If you have to read off of your slides, it’s because you don’t know your material.

But overall, the most important thing is that your deck flows and that you’ve validated your business model.

The Pitch

Beyond the above, I have a few tips for delivering your presentation:

  • Do a tech-check before you present. Make sure your slides load, that they work on the projector, and that the slide controller works
  • Only one person should be presenting. This maintains a consistent flow throughout. Have the rest of the team off to the side of the stage (depending on the event configuration)
  • Any time where you’re not actually presenting can be used to influence the audience and the judges. For example, while you’re walking to the stage you might make a joke to warm the audience up.
  • Use your slides as a prompt. You don’t have to memorise your speech, but each dot point on each slide is a talking point. Understand the flow, and use those points to remind you of the key things you need to discuss. When you change slides, don’t be afraid to take a quick pause to turn and look at the slide behind you to remind yourself.

Question Time

After your pitch, this is when the whole team comes out and the judges ask you questions — about what you’ve produced, about your validation, about the team, everything.

This is typically the time that gives you an opportunity to address any gaps that might have been in your slides. For example, if you don’t cover how you plan on growing the business in your presentation, you better have an answer for it when the judges ask you.

This is also the time when the judges might raise any problems that the business could potentially encounter — these might be legal, moral or just general issues related to the business. You need to be realistic about your business and have answers for these questions that show you have thought about these problems. Eg, if you talk about expanding nationally but one of the competitive advantages you discussed was strong connections in the local market, then you better have an answer when they ask you about that.

Question time is also a great time to get other members of your team involved, and to show how well your team works within its roles. Eg, in one of our presentations we got asked about the financial estimates that we’d put together. This was a great time to pass over to the person who had prepared those, to have them justify the costs and revenue that we expected.

As long as you know your business, and have given serious thought to the challenges you might face, then question time shouldn’t be a challenge.

Winning Startup Weekend

With the world’s best five minute pitch, you’ve wowed the judges and earned a standing applause from the audience. You had bulletproof answers to the questions that the judges asked and after politely hearing out the other teams, the judges have come back with the inevitable conclusion that your team has won Startp Weekend! Congratulations — venture capitalists will be waiting outside, ready to fund your business idea with their millions of dollars.

Or maybe not. Maybe your team didn’t gel over the weekend, maybe you couldn’t get validation for that idea, maybe the MVP couldn’t get built, maybe it all just fell in a heap.

Whatever happens, remember this — it’s all for fun. Unless you have especially generous sponsors, the prizes at Startup Weekend aren’t all that great, and many of the businesses started over the weekend will fail to last out the rest of the week. Hopefully you’ve at least had a chance to explore an idea that you were interested in, and learnt something new which you can apply in your own entrepreneurial endeavours. If you’re really lucky, you’ve even met someone who you can work with on a different project (our designer from Crowd Control later helped me with some of the branding for Squishy Forts).

With Crowd Control’s victory, a group of us from the original 11-person team decided to continue on with the idea. Within a few weeks we had rebranded (so we could get a decent .com) and winnowed the team down to just 3 people — our designer, one of the developers and myself. 18 months later, we’re no further ahead. We all got busy on our own projects, and the business is all but defunct.

But that’s okay — I met some great people, had a great time and now I get to brag to everyone I meet that I won Startup Weekend. #StartupStreetCred