For a brief period I’ve called myself Founder of Designladder. An app that would change creative careers. It was absolutely doing that, until we closed shop.
That makes me a failed startup founder. How to continue my life? For this session I invited my co-founder and you: my lovely reader. This is a safe space, so let’s all be honest and frank. How did this happen? How do we live on?

Tim:
Designladder was an app that helped designers build the career they desired. Users were handed all the guidance and tools they needed to sketch, prototype and design their careers – just like a design project. Awesome idea, right?

Freek:
Designers agreed! Oh, by the way, I’m Freek Wallaard, Tim’s co-founder – dealing with startup failure too. Our network’s showed strong interest in the idea. Good start. And you got some of design’s top dogs on board with us, Tim.

Tim:
Yes, we got to interview these wise men: Lockwood, Turner, Picaud. Friends, but also very experienced design leaders. We found out their thoughts and they gave us lots of confidence.

Freek:
Absolutely. I expected that this type of credibility and attractiveness would open doors at every design department in the world. We had already gathered a really nice group of testers from all corners of the world at that point too…

Tim:
Yes, and they paid 1 dollar for the service. I thought that that was soooo clever at that moment. We kind of forgot to ask them what they realistically wanted to pay for all of this.

Freek:
Scaling wasn’t our first concern. We found plenty of articles on Medium and HBR that said to worry about that later.

Tim:
Yes! Our test setup was basically doing 1 on 1 coaching with designers online. I soon felt overwhelmed by the idea that I had to do this for the rest of my life 40 hours per week. So we started to develop towards automation. Then I found this video by the founders of AirBnB and it helped to put this automation urge to some stop. Superficially. Deep inside I still felt that worry.

Freek:
I remember having so many worries. Us spending too much, focussing on product too much and not enough on marketing, but then seeing that the product needed more in order to market it with confidence, and then having to change our marketing with every new development sprint. I felt torn at times.

Tim:
I never had that, as I stayed on my own turf: product development.

Freek:
You had much more focus! I kept feeling that we needed to connect with more people. I liked building onboarding products. That gave confirmation that our ideas worked way outside our network. Goalsfordesigners.com was such an onboarding product. We got hundreds of designers posting their career goals and inspiring each other. Goals were posted in English, but also in Mandarin, Hindi and Spanish. A lot of people loved it, we even got featured on Producthunt.

Tim:
And I hated it. I felt like we were building fixes to our own flawed product.

Freek:
Sounds pretty agile?

Tim:
Agile! With all of experience in innovation processes we thought that we did everything well. We acted agile. We played agile. But we weren’t. Not truly. We were constantly pursuing the perfect vision. Offering a half-baked version didn’t feel good. Even if we told ourself that we were ‘iterating’.
What did we think? Spending €7000 on a logo…

Freek:
Add a €10K design sprint with a top digital agency. The least we could do as a for-designers-company, was treat designers well and work with the best.

Tim:
Large-company-behavior.

Freek:
It bought us motivation. We both thrive with high quality standards. Ambitious brand and product: we set the bar for ourselves with that. Everybody we worked with lived up to it. Even the users of our app felt this apparently, as they delivered really great stuff.

Tim:
Okay, so since we’re talking about feelings now: if I tell people about my failure as a startup founder, I feel a strange kind of pride!

Freek:
Ahh, that’s cute! Oh sorry, safe space ;-).

Tim:
I feel a sense of pride. Certainly when I add that I paid all this from our own money. I think it has to do with having chased a dream instead of putting it on ice. Also with so many lessons learned.

Freek:
Add passing a litmus test of our friendship to that!
And let’s not forget: the whole of the company failed, but we succeeded big time in elements. We both have grown immensely in our roles. You as Head of Product, me as Head of Brand. I like to say it’s been a highly valuable self-organized MBA. We did fail, but we chased a great vision, we worked day and night, we got far and harmed nobody. No bill was left unpaid.

Tim:
So, it balances everything that went awesome, or is startup failure actually good because you learn so much from it?

Freek:
It’s tough to be realistic about this when it’s about our own failed startup. I know how I feel: I’m making our failure worth it in every project I do now. I also know what I would advise new startup-founders.

Tim:
See, there are things we agree on! Making it worth it – that sums it up well. I’m working at this NGO, and we’re pretty much building an internal startup right now. I’ll still stick to the vision relentlessly, but with added wisdom and realism.

Freek:
Also you have gathered some highly intelligent readers, right? This seems like a good moment to ask them to join the conversation.

Tim:
Yes! My beloved readers! I’d like to ask about your personal style of innovating. I personally feel like my way of working, I’m holistic and uncompromising, might not fit a startup too well. I want to create the full vision, and do it very well. My question: how would you describe your innovation style and do you feel like it fits certain company types better than others, for example startup versus large corporates?

Email your thoughts to me at tim@sharppanda.com. I will personally answer or react to every single one. Of course.

Tim:
Well, Freek. That was …good. Yes. I feel a little lighter! Thanks everybody who had and will have this conversation with me.