Winning Pioneer After A Radical Change Of Direction

Lewis, Harry and I have become the latest team to win the Pioneer tournament 🥰 It was actually several weeks back but we were asked not to share the news until they had announced the latest batch of winners...which they did today 🎉

Pioneer is a tournament for startups, we competed for a total of 26 weeks before winning, but we actually won after ditching our project and starting something completely new that lead us to victory in just 6 weeks!

The radical change of direction was to create HackerStash - a community-lead micro finance initiative for hackers and entrepreneurs. It's a bit like if Indiehackers and Pioneer had a baby, and that baby really wanted to help early stage projects succeed, and raise cash without giving up equity.

This isn't going to be another 'tips and tricks' post for Indiehackers wanting to learn about how to participate in Pioneer. We've written at length about our experience in the tournament here, so if you want to know what it's all about, and what the journey was like for us, then feel free to check it out. It's also not a success story - we've not even launched and it's still more than likely that we'll fail. Instead, I wanted to share on Indiehackers what went wrong with our first project, why we undertook such a big pivot (well...we just canned our previous project), and whether there were any lessons learned.

Digging A Hole

We first started Pioneer when working on Codefree. It was a no-code CMS, with a focus on maintaining feature and UX parity on any device. With 5.4 billion people soon to be mobile-only internet users, I still believe a viable mobile ready CMS represents a huge opportunity (in fact I've controversially explored the opportunity of mobile-only apps just recently).

We were already 7 months into our project when we joined Pioneer and started posting our progress updates. Honestly Codefree was/is pretty damn cool, there's some incredible design thinking that's gone into the app, and some pretty ground breaking technological innovation, but frankly it was a gargantuan undertaking that we fell out of love with.

So what happened? Well, in time honoured tradition for those of us that fail to launch early, the project snowballed. We were perpetually kicking our launch date down the road, adding new features, fine tuning the UX, refactoring the code etc...and always with an eye on new features we deemed 'essential' for launch. Not only that, but we were building a CMS to let people build websites and we had no dedicated frontend expertise on the team 😂.

One day it dawned on us, we hadn't enjoyed the project for months. Sure, starting a business should be tough, but you need to love the challenge you've taken on if you're going to make a success of it. We'd spend the best part of a year working on it around our day jobs, family lives etc, and had simply dug ourselves a massive whole with no clear way out. So with heavy hearts, we pulled the plug.

Honestly, there's loads of indiehackers that have felt this pain, I know I've read enough horror stories about misplaced years and failed endeavours, but somehow we made the same mistake - our project had died having only graced the screens of a handful of alpha testers.

Get Back On The Horse

So, when your dreams of SaaS application glory implode with little more than a squeak, what do you do next?

In some ways we were lucky, we had learned a lot during the Codefree project, and our team spirit and desire to work together was as strong as ever. We'd been doing great work, but in the wrong ways, and we'd failed to find a project meaningful enough to inspire ourselves through the darkest hours.

We used the down time after Codefree to contemplate the struggles we'd been facing, not just during the project, but as veterans of other failed or struggling side hustles and startups. After lengthy discussion, we ended up defining 5 principles that we felt should inform our next project:

• We truly believe in the transformational potential of great ideas, and we want more hackers and entrepreneurs to succeed.
• Too many projects and businesses fail due to a lack of access to fairly small amounts of early capital.
• Learning from early, regular feedback, from your peers and/or users, is key to most successful projects.
• Being accountable to people outside of your team (or outside of your own head if you're a solo founder) can be like rocket fuel for productivity.
• Your network truly is your net worth.

Alongside agreeing that these should be the focal points of our next project, we also found ourselves reflecting on our time using Pioneer. We loved the tournament format and it was a good fit for our project, but there are plenty of projects and businesses looking for something different.

Not everyone wants or needs to join an accelerator, or get on the VC choo choo train - they want to bootstrap their way to success without giving up equity or acquiring massive piles of cash to burn through.

We seemed to be settling on a new direction: a tool for hackers, entrepreneurs and bootstrappers that will help them fund and launch awesome projects without the need to give up equity.

A Horse Named HackerStash

Excited to get started, we snapped up a URL that matched our ambitions, and quickly threw up a landing page for HackerStash.com and we reached out to the IHer community for feedback on the project.

In summary, HackerStash is a community-led micro finance initiative for hackers and entrepreneurs. A private community with a monthly tournament where you share progress on your project, get great feedback, and have the opportunity to win cash prizes to support your project. The community votes for the winners each months, and the project could be a new business, but it might even be a non-profit or open source endeavour where you're not especially concerned about making money - you just want the idea to succeed.

The feedback from Indiehackers, and fellow pioneer competitors was super positive, people immediately understood the value proposition and we were quickly garnering waitlist signups...just the sort of early validation you need for a new idea!

So, we started design and building the app, and sharing our progress on Pioneer and Indiehackers. We climbed the Pioneer leaderboard consistently for a number of weeks and then, just 6 weeks after throwing up the landing page, we became Pioneer Winners!

Again, I'm not going to dwell too much on what it means to be a Pioneer winner, you can read about that at length here, but needless to say it will be a big help for our particular project.

Lessons Learned(?)

It's very hard to draw concrete lessons when our latest project is still in its infancy, but at least in terms of the life and death of Codefree, and the birth of HackerStash, these have been our key takeaways:

• Get a landing page up, seek immediate feedback on your proposition, and see if there's an appetite amongst your target users by creating a waitlist. You can do all this before you've even written a line of code for your product.
• Launch early and get feedback asap - remember, you can launch more than once. Honestly, we're still learning this, we've been working on HackerStash for 3 months now(!), but then again, we're genuinely just a matter of weeks from launching, we've learned loads from waitlist subscribers already, and have users testing the product this coming week.
• Seek meaningful and productive relationships with your cofounders. Most ideas and products will fail but you'll be able to move onto the next exciting project faster and stronger than before, if you've learned hard lessons together.
• When you've finally accepted a project has run its course, you'll feel terrible. You've failed, and you've invested a stupid amount of time to do so. But there are likely valuable lessons to be learned, new values to be formed and perhaps even the sparks of the next idea.

It's all still very recent, and we've been somewhat swept up in the momentum of our next project, so I'm sure further lessons will continue to be drawn from Codefree's failure. For now though, we're focusing on building something new that will hopefully help others avoid some of the same challenges and mistakes we encountered!