How to win the 'Pioneer' startup tournament in 1 month

What is Pioneer?

Pioneer.app is an online startup accelerator that helps founders track progress, get advice, and get funded. At the core of Pioneer, there is a tournament in which participants are scored primarily through weekly peer-review of progress updates.

The top 50 startups are eligible to get selected by an expert (Marc Andreessen and Patrick Collison to name a few). When your startup is selected, you win the tournament and get the Pioneer offer including a trip to Silicon Valley (after the pandemic), access to a network with other pioneers, an online accelerator program, mentorship, potential funding and much more.

So, how did we get to the top of the leaderboard and win Pioneer in a single month?

How we got started:

All of us, the 3 co-founders at Emcee, had worked on a startup before and we know that startups are built on speed. We started working on Emcee a couple of weeks earlier and were directly focussed on building momentum since that was what was going to make this work. We built the MVP and got our first testers in a couple of days and started brainstorming growth ideas while building out features for our first users.

One of our growth ideas was to participate in the Pioneer tournament and see if some of the other participants knew someone with a webstore or even better, owned one themselves.

What does a good weekly update look like?

The bread and butter of the tournament are the weekly updates. If you want to win the tournament, this is an excellent place to start.

Here are a few rules of thumb we used ourselves:

Make it engaging:

• All participants vote and give feedback on multiple updates so make it as fun as possible to read yours.
• Adding emojis to your update makes it look fresh! 🍋

Make it quantifiable:

• Make sure everything is trackable and clearly shows the progress you are making. “Sending emails to potential clients” → “📧 Prospect and email 50+ leads”

Use links:

• You have a limited amount of characters for your updates, use them wisely.
• Post links to your blog articles, a demo video, and images with more information.
• How we did it:
  • Posted images on Imgur (unlimited characters)
  • Posted a video demo on Loom. This could be a whole separate section on its own. A video makes it a lot easier to communicate what you are doing.
  • Used link shortener (Bitly)

Overperform weekly goals, overconfident long term goals!

During your participation in the tournament, you are able to specify 2 types of goals: ‘What do you want to have done by the end of next week?’ in your weekly progress update and KPI’s.

For our weekly progress update, we set goals that were easy to track and overperformed on them. Whenever we said we were reaching out to 50+ prospects we made sure we contacted at least 75+. Whenever we said we were optimizing something we also implemented a new feature.

This is an example from our second weekly update:

Looking back at it, ‘optimize mobile MVP’ could have been better.

Unlike progress updates, your KPIs should look to the next several weeks or months, not days. The KPI’s we set for ourselves and that we have tracked over the following month were very ambitious and we knew we were probably not going to make all of them but it put us in a spot where people knew that we are in it to win and we’re not interested in an average outcome.

Give constructive feedback

Not only will giving constructive feedback earn you more points. You will notice that the people you gave feedback in previous weeks might be asked to give feedback on your project later on.

Participants will remember when you gave them constructive feedback that helped them progress, we even got in contact with a few of our biggest potential customers so far through Pioneer referrals.

That doesn’t necessarily mean you have to be overly optimistic about another participant's project, but make sure you take time to write something that has meaning and helps the other participants out. Pay it forward!

Time management

It’s easy to forget all the progress you make during a week when you are working on a startup. We started creating a list of all the things we do during a week so we don’t have to remember it for the weekly update. This is not only a good exercise to see your momentum build up but it also makes writing the update a lot easier and less time-consuming.

Conclusion:

In the end, it all comes down to putting in enough work to make fast progress and how clearly you can communicate that progress to the other participants.

Doing this gave us 90%-100% upvotes for multiple weeks and skyrocketed us up the leaderboards until Pioneer couldn’t ignore us anymore and sent each of us an email with the magic subject line: ‘You're a Pioneer!’.

Here is an example of a weekly update we submitted:

If you liked it perhaps like or retweet the thread on Twitter:

Good luck & we hope to see you on the leaderboard soon!