3 things I learned from my biggest failure (so far!)

I had the largest and most public failure of my career today. (okay, so it was really about 2 months ago but that didn’t sound quite as dramatic...). I was the lead organizer for an internal project called the Accelerator. The goal was simple. Give engineers an opportunity to build their moonshot ideas.

Teams of engineers would put together a pitch for their idea. The most promising among them would get 2 weeks to bootstrap an initial version.

Over the course of 6 months or so, I wrote proposals, pitched higher-ups on the idea, booked rooms, organized brainstorming sessions in an attempt to make the Accelerator a success.

There was just one problem. When the time came, no one showed up. Literally not a single team signed up to pitch their idea. None.

So what could I have done differently? I’ve come up with 3 main things I would change if I could do it over again.

Don’t get too caught up in your own hype

Whenever I talked to my work friends about the Accelerator, I got a lot of positive reinforcement that this idea really had legs. Apparently though, what they were saying was, “That sounds like a really good idea… for someone else or at some non-existent point in the future.”

Your friends and family don’t want to be unnecessarily critical of your idea to your face and potentially people are conveying honest interest. The reality is that, unless your social circle overlaps with your pool of customers, their positive feedback is a weak signal. Importantly, the converse can also be true. Just because people tell you it’s a bad idea, doesn’t necessarily mean it is. So how are you supposed to avoid this problem?

Talk to your potential customers

There’s a common mistake discussed on sites like Indie Hackers where startups essentially guess what features customers want without having real feedback about what they’re building.

I made this mistake with the Accelerator. I designed the program that I would have wanted, in particular the opportunity to work on a passion project for two weeks. Unfortunately, people didn’t feel like they could budget the two weeks of time for the main part of the accelerator so they decided not to pitch any ideas.

The core value proposition of the Accelerator was turning people off from participating! But we didn’t learn that until we surveyed people after the first attempt crashed and burned.  Talking to potential customers before we even put on v1 could have led us to understand how our current version wasn’t working for them.

All that said, there’s still a big difference between people saying they’d be interested in something and them actually “buying” when you launch the product, which leads into the next thing I’d do differently.

Get your V1 out there

Another mistake I’m going to avoid in the future is creating a big and polished V1. In our case, this manifested itself as going too big for the first version. Our first iteration of the project included around 400 potential participants across two internal teams.

Coordinating for this many people between the two teams was a major drag on our ability to move quickly. By the time we put on the initial version of the Accelerator, we had been planning it for around 6 months. In retrospect, it would have been better to put on a trial within our own team (around 50 people) to prove out the idea before trying to ramp it up.

All of this is to say that it’s much preferable to put together something quickly and get it in front of people to start learning what people really need. You don’t want to wait months or years before getting any feedback and only learning then that all your assumptions were wrong.


I wish I could say that I’m going to pick myself up and dust myself off and put on a shiny v2, avoiding all of the pitfalls of the first round, but I’ve stepped back from my role coordinating the Accelerator, so I won’t get a chance to do that. Nevertheless, I’m going to take the lessons that I learned the hard way this time and apply them to my future projects.

The larger, meta-takeaway for me is that I tried something and it didn’t go well but that’s okay. I didn’t spontaneously combust because I didn’t succeed. I’m going to take this in stride and try and try again.

Matthew Keller