Fail Fast March Madness: Picking the Best Startup Fails & Recoveries

Fast Fails = Fast Learners: See the contenders in this year’s Tech March Madness Tournament

They say the tech world celebrates failure, but it’s how you bounce back that really counts. We chose 16 entrepreneurs who learned from their mistakes the hard way — now it’s up to you to decide who did it best.

In the world of entrepreneurship, failure is reality. Once promising businesses collapse every year. Smart founders find themselves up against the wall needing to pivot or surrender. Seemingly infallible products fall short of expectations. Even successful founders and teams come up short at some point.

Accepting that reality — that failure, in some form, is an inevitable aspect of building an innovative business — is critical to every tech company’s development.

Let’s Stop Celebrating Failure and Celebrate Resiliency, Instead

That said, failure is not something to celebrate, despite what certain tech hubs would have you believe. It’s not a badge of honor. It’s not absolute proof of innovative risk taking. And it’s certainly not something to be glorified or bragged about. Yes, failure can be evidence of a valiant (but failed) attempt to achieve something great. But it can also be indicative of foolish decision making, poor vision, and condemnable hubris. The difference matters and the latter shouldn’t be commended.

Instead, failure must be viewed through a different lens to reveal what it actually is: An opportunity to learn, grow, iterate, improve, and rebound. As Zendesk founder and CEO Mikkel Svane writes in his new book, Startupland:


“Failure is not what we have rewritten it to be. It is not something to be proud of; it is not something to flip about; it is not something to celebrate. No, failure is simply something we can learn and recover from.”

— Mikkel Svane, Founder & CEO of Zendesk

Tech March Madness: Fail Fast Bracket

Tournament Schedule

  • Round 1: Tuesday, 3/17 (voting ends Sunday, 3/22)
  • Round 2: Monday, 3/23 (voting ends Tuesday, 3/24)
  • Final Four: Wednesday, 3/25 (voting ends Thursday, 3/26)
  • Championship: Friday, 3/27 (voting ends Monday, 3/30)

On that note, we’d like to welcome you to OpenView’s third annual March Madness bracket.

As you might have guessed, this year’s theme revolves around tech founders who have failed. But this tournament isn’t about honoring the startup world’s most notorious fails or complete disasters (you can find a list of those here). It’s about acknowledging entrepreneurs who have successfully leveraged the experience of failure to catalyze new innovation, improvement, or growth.

Below, you’ll find a March Madness style bracket with 16 profiles grouped into four “regions.” Each region has its own failure-related theme and we’re leaving it in your hands to choose which entrepreneurs are most deserving of moving on to the next round. Again, the goal is to focus on founders who tried, failed, learned from it, and bounced back in a big way.

Which entrepreneur has done that best? It’s your job to decide. So, get to voting — and please feel free to share your picks (and this bracket) with your network!

Who Has the Best Failure/Turnaround Story? Cast Your Votes!

Deadline for Round 1: Sunday, 3/23

Click here or on the bracket image below to cast your votes!


The Contenders: Pivot Region

[new_royalslider id=”83″]

Mark Organ, Founder of Eloqua and Influitive

Pivot Region #1 Seed

The Fail: Targeting the wrong market with the wrong features

Find out more and vote for Organ here

Stewart Butterfield, Co-founder of Flickr and Slack

Pivot Region #2 Seed

The Fail: A “never-ending” online game that flopped — twice

Find out more and vote for Butterfield here

Justin Kan and Emmett Shear, Co-founders of and Twitch

Pivot Region #3 Seed

The Fail: A 24/7 reality show live-streaming Kan’s life

Find out more and vote for Kan and Shear here

Ben Rubin, CEO of Meerkat

Pivot Region #4 Seed

The Fail: A live-streaming video app with no heartbeat

Find out more and vote for Rubin here

The Contenders: Pricing Mistakes Region

[new_royalslider id=”84″]

Reed Hastings, Founder and CEO of Netflix

Pricing Mistakes Region #1 Seed

The Fail: Qwikster

Find out more and vote for Hastings here

Jason Lemkin, Co-founder of EchoSign

Pricing Mistakes Region #2 Seed

The Fail: Launching without a pricing plan

Find out more and vote for Lemkin here

Robin Chase, Founder of Zipcar

Pricing Mistakes Region #3 Seed

The Fail: Having to tell her users to take a (pricing) hike

Find out more and vote for Chase here

Chris Savage, Co-founder of Wistia

Pricing Mistakes Region #4 Seed

The Fail: Scaring away a major early customer with a price that was way too high

Find out more and vote for Savage here

The Contenders: “Un-Lean” Region

[new_royalslider id=”85″]

Nick Woodman, Founder of GoPro

“Un-Lean” Region #1 Seed

The Fail: FunBug, a dot-com boom gaming and marketing site that went bust

Find out more and vote for Woodman here

Brian Chesky, Joe Gebbia, and Nathan Blecharczyk, Co-founders of Airbnb

“Un-Lean” Region #2 Seed

The Fail: Not recognizing people want to actually see what they’re going to get

Find out more and vote for the Airbnb guys here

Hiten Shah and Neil Patel, Co-founders of Crazy Egg and KISSmetrics

“Un-Lean” Region #3 Seed

The Fail: A web-hosting company that never saw the light of day

Find out more and vote for Shah and Patel here

Danielle Morrill, CEO and Co-founder of Mattermark

“Un-Lean” Region #4 Seed

The Fail: “Affiliate-for-everyone” marketing startup

Find out more and vote for Morrill here

The Contenders: Hiring/Team Mistakes Region

[new_royalslider id=”86″]

Kathryn Minshew, Founder of The Muse

Hiring/Team Mistakes #1 Seed

The Fail: Seeing her founding team self-destruct

Find out more and vote for Minshew here

Parker Conrad, Founder & CEO of Zenefits

Hiring/Team Mistakes #2 Seed

The Fail: Getting ousted from his own startup by his co-founder

Find out more and vote for Conrad here


Tony Hsieh, CEO of Zappos

Hiring/Team Mistakes #3 Seed

The Fail: A series of bad hires that cost Zappos over $100M

Find out more and vote for Hsieh here

Anthony Casalena, Founder of Squarespace

Hiring/Team Mistakes #4 Seed

The Fail: Waiting too long to hire and fire

Find out more and vote for Casalena here

Senior Content Manager

Jonathan Crowe is Senior Content Manager at Barkly. He was previously the Managing Editor of OpenView Labs.
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