Want Success? Fail Often and Fail Fast


Andrew Calderon has been a member of Founders Network since October 2017. He’s also been a prominent FN member in our Toronto Chapter. To receive peer mentorship from Andrew and over 600 fellow Tech Founders, please request an invite and join our global network.

Mike Tyson famously said, “Everyone has a plan ’till they get punched in the mouth.” For startups, it should be part of your plan. Plan on needing to counter punch and lick your wounds as you pick yourself off the mat. Every entrepreneur needs a delusion of grandeur when they start their business, the impossible goal to achieve. It’s that same goal that rarely changes.

Want to be a better and more profitable search engine than Google? Sounds delusional, right?

Good, next step…get there.

Assume You’re Wrong

This is where your plan needs to assume you’ve got things wrong, but you don’t know why yet. Your ability to learn, react and adapt to failure eliminates failure from your company. Own these failures and integrate what you’ve learned into your culture. When you accept responsibility and set the example from the top, every failure turns into a lesson learned for everyone after you. It organically creates a culture of collaboration where failures become group discussions on how to pivot and deflect into success.

Follow Your Delusion of Grandeur

Our product had a simple goal to achieve when we launched; eliminate bad interviews from the hiring process. You’re all familiar with it; you shake someone’s hand who comes in for an interview and before they sit down, you know they’re not getting the job. However, you feel obligated to give them 20 minutes, wasting both their time and yours, so that they can at least feel as though they got a fair shake. Our goal when we started was to close one of the 5 largest possible clients in the country within 24 months of presenting the product concept to investors.

We went through a lot of growing pains, pivots and failures to accomplish our first goal. Most importantly, we never lost sight of our delusion of grandeur and kept our direction true through all of our changes. The result was a tightly focused product that we tested with not one, but two of the largest companies in the country before we were at version 1… within 24 months, we were at three of five.

Four Lessons Learned From My Failures

1. Failure is a tough pill to swallow, remove ego from the equation as early as possible and don’t mock others for their failures… poking fun at your own is ok.

2. Create and embrace processes that force you to acknowledge and review failure and paths forward. Sometimes you just acknowledge, “yup, that was dumb… not going to do that again… Hey everybody, don’t do THAT.

3. Build a strong advisory board around you to help support your growth and provide honest feedback.

4. Most importantly (and this is out of left field): Keep things strong on the home front. Maintaining a  work/life balance is a tough and sometimes impossible achievement. However, your calendar can be your friend. Book time with your family and friends. It will keep you grounded and increase your capacity to work through problems in the long run.

Failure can be overwhelming and turn into quicksand; the harder you struggle to succeed, the faster you sink. Accepting failure keeps you from sinking any further. Analyzing and sharing failure gives you options and the ability to collaborate with others to find a way out and rise back up. 

Embracing failure is your secret weapon to succeed and make it look like you never failed.

Share With Your Network

Looking for startup advice, connections, and insights?

Tap into a global network that enables you to answer questions, build relationships, and gain the perspective you need to move faster.
Peer mentorship with fellow tech founders
Pitch practice with Tier 1 VCs
Accelerator grade discounts