Launched a year ago to inspire people to take on daily bouts of creativity through drawing challenges, DrawQuest, reached 1.4 million downloads, 550,000 registered users, 400,000 monthly users, 25,000 daily users, and 8 million drawings but still failed. No one is guaranteed success. No matter how hard you work, things never go as planned.

Chris Poole, the founder of DrawQuest had raised about $625,000 in seed funding from investors Ron Conway, Marc Andreessen, Chris Dixon, Kenneth Lerer and Joshua Schachter in 2010, TechCrunch reports.

After that came another $3 million in 2011 from Union Square Ventures’ Fred Wilson, SV Angel, Lerer Ventures, Andreessen Horowitz, Founder Collective, and Joshua Schachter.

The original funding was to develop Canvas, a forum for sharing and discussing online graphic and art images. But then Poole’s team switched to DrawQuest instead about a year ago.

Luckily for aspiring entrepreneurs, Chris (also the founder 4chan, a successful image-based bulletin board) shared the DrawQuest postmortem with the public.

Here is why DrawQuest was shutdown (as shared by Chris)

He said “I’m incredibly proud of an amazing team and all that they have accomplished. Our most recent product, DrawQuest, is by all accounts a success. In the past year it’s been downloaded more than 1.4 million times, and is currently used by about 25,000 people a day, and 400,000 last month alone. Retention and engagement are great. And yet we still failed. It may seem surprising that a seemingly successful product could fail, but it happens all the time. Although we arguably found product/market fit, we couldn’t quite crack the business side of things.

Building any business is hard, but building a business with a single app offering and half of your runway is especially hard (we created DrawQuest after the failure of our first product, Canvas). I’ve come away with new found respect for those companies who excel at monetizing mobile applications. As we approached the end of our runway, it became clear to us that DrawQuest didn’t represent a venture-backed opportunity, and even with more time that was unlikely to change.

No soft landing, no happy ending!

Chris further explained “I’m terribly saddened that this may spell the end for our wonderful community, but it’s my goal to use what little money we’ll have left after the wind-down to keep the service alive for another few months. However as of today the team has gone their separate ways, and our doors are effectively closed.

I’m disappointed that I couldn’t produce a better outcome for those who supported me the most—my investors and employees. Few in business will know the pain of what it means to fail as a venture-backed CEO. Not only do you fail your employees, your customers, and yourself, but you also fail your investors—partners who helped you bring your idea to life.

In my case, I am extremely lucky and grateful to be partners with people who are simply the best. What separates the best investors is not how they help you when you’re a rocketship, but when your ship is on fire and you’re venting atmosphere. In this case, our investors have demonstrated what sets them apart from the rest—they’ve supported me throughout the ups and downs, and especially the downs.

With that said, life goes on, and the best path forward is not a wounded one, but a more learned and motivated one. I’m definitely not itching to start another company any time soon—it will take time to decompress and reflect on the events of the past four years—but I hope that if I do some day decide to pursue a new dream, I’ll be in a much better position to.

As for what’s next for me, I honestly have no idea. This is the first time in four years I’ve been at a crossroads like this.

One thing I’ll be doing more of is writing about my experience. Partially because it’s therapeutic, but also because if there’s a silver lining in all of this (and there is), it’s that I can help educate others about a path fraught with hardship, but rewarding nonetheless.

I’m also particularly inspired by what Everpix has done by making so much of their story public, and hope many others will follow in their footsteps of radical transparency. I don’t wish to glorify my failure, but it’s certainly something I’d rather embrace than hide behind for the next five years.

“There’s a lot of glorification of startups and being a founder. People brush the failures under the rug, but that’s the worst thing you can do. You kind of have to face it head on,” says Chris Poole. 


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