September 6, 2016 - No Comments!

Drive After Audacious Goals Without Regard For Their Improbability

I almost titled this article “We’ve Lost Our Naivety”. Here’s why:

As a senior in college, with no experience and no network, just a love of product design, I decided to start a company. Why?

In a course I was taking senior year — Design of Information — I hadn’t kept up with my “design journal” before the first journal check. Needing to fill 10 pages in one night, I picked a topic so hairy and difficult I figured it’d easily fill the minimum page requirement. That topic? Email.

By page 3 I was in love with what I had sketched. It captured every ounce of my fascination. It made so much more sense than anything I had seen before.

After months of discussing the idea with people and iterating on it, we turned to Kickstarter. This was January 2012. My life changed entirely that month.

Knowing no one in the industry, having no prior experience, no previous work to prove my credibility, no existing audience to leverage — just Photoshop, Xcode, and a passion for thoughtful and empathetic product design, we launched a Kickstarter campaign with a goal of raising $35,000. If that doesn’t sound impossible yet, it’s also worth nothing that no closed-source software project had raised that much on Kickstarter, let alone one from some no-name undergrads.

After 5 weeks, a feature in the New York Times as “Ingenious” and WIRED Insider’s Kickstarter of the Week, with praise from our idols such as Jason Fried, a “Staff Pick” listing on Kickstarter, and most importantly, with 1,623 backers, our humble Kickstarter campaign succeeded with over $54,000 in funding.

We went on to follow up the campaign with a handful of even more surprisingly successful launches.


Someone recently asked me what the key ingredient was.

Honestly, I think it was equal parts excitement for an idea that we really believed in, and thought should exist in the world, and naivety — not knowing just how impossible it was. We’ve been able to bootstrap the business for years since that Kickstarter campaign. If we had laid out what has happened the last four years as our plan back in 2012, and asked some pros in the industry what they think, they’d laugh us off.

We embarked on the journey because we didn’t know it was supposed to be impossible; we were blinded by ambition, and enabled by naivety.

The problem we have now is we aren’t naive anymore. I hear us more and more saying things like:

“No, there’s no way that’ll work”

“It takes years to build up an audience to do that”

“Big Company X invested hundreds of thousands to launch their podcast, there’s no way we could get close to their level of success”

“The best content marketing strategies are executed by teams in companies dedicated full-time to writing and publishing, we shouldn’t even try.


We’ve lost our naivety.

Our new secret to success, one I hope you’ll embrace in this new age where things that seem daunting are secretly possible, is a new focus:

Drive after audacious goals without regard for their improbability.

I write this primarily to myself, but maybe you’ll glean some value from it too.

The only people that find out impossible goals aren’t impossible are the ones who try to achieve them. If you know too much, and you’ve become cyncial — if you think of all the things you don’t have to achieve the things you want to do, if you’ve found yourself walking down more and more traditional, mediocre paths, then I’ve got a message for you:

It’s time to embrace willful naivety.

Your successes, failures, and everything else you’ve learned to get to where you are now are holding you back. Embrace the naivety that got you started. Drive after audacious goals without regard for their improbability.


If you want to follow on this journey with me, as I willfully return to the naivety that got me started — so that we can once again embark on impossible goals, then subscribe to my newsletter. I’ll send you a new article every Thursday, and soon enough, a book on product design and innovation.

Learn to make world-class products that sell themselves.

Get actionable insights on product design and product ideation each Thursday morning, so you can become a pro at creating products people will love.

Powered by ConvertKit

Get new articles before they're published.

Get actionable insights on product design and product ideation each Thursday morning, so you can become a pro at creating products people will love.

Powered by ConvertKit

Published by: Alex Obenauer in Bootstrapped

Leave a Reply