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:
— Mikkel Svane, Founder & CEO of Zendesk
Tech March Madness: Fail Fast Bracket
- 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
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 Justin.tv 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
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
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 Refer.ly
Find out more and vote for Morrill here
The Contenders: Hiring/Team Mistakes Region
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
Liat Bycel is the VP of Customer Engagement at Airtable. She shares how they made the decision to bring all customer-facing teams under one roof and how that decision has furthered their growth and made the customer experience more cohesive.
Couldn’t make it to our fourth annual Product Led Growth Summit? Don’t worry, OV’s Jeff Curran broke down the key takeaways here.
Pendo’s CEO discusses how this team built the product and organization to deliver a winning solution to the world.