On the Necessity of Failure: A Founder’s Stories from the Trenches
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On the Necessity of Failure: A Founder’s Stories from the Trenches

 

As an entrepreneur, you live and breathe every moment of your startup. The highs make you feel ecstatic; the lows can be soul-crushing. It’s a constant roller coaster. With long hours, multiple stakeholders, and other people’s money invested in your vision, every decision feels like it could be make-or-break. This is a huge amount of pressure for any founder. So much, that it often feels like there’s no line between the company and you — your company is like your baby, an extension of your heart and mind in many respects. And when you’re “in it” that deeply, you worry that any misstep has the potential to take you down ... as well as the company. So, what’s one of the greatest things for an entrepreneur to learn? How to fail.

Crash & Burn... then Learn

We called it PickTeams. It was a social gaming startup that had the validation of a few VCs, our dedicated employees, college students across the company, and the media. It was five recent college grad co-founders on a mission to figure out how to generate revenue around a concept we were incredibly passionate about. But passion is no match for the financial crash, and when we were unable to raise an additional round of much-needed venture capital in 2009, we realized we were not going to be able to move forward. By summer of that year, right when I was set to graduate from from college and go to work full-time as co-founder of my own startup, over two years of nonstop effort and hard work came to an end — the dream had evaporated. Our startup hopes were dashed.

There was shock, denial, anger…every stage of grief (Steve Blank describes them all here). It all feels very personal, and makes you question a lot of things - including yourself. But in time, there’s clarity and there’s major learnings. It takes time to find that silver lining, but acceptance, insight, and personal growth are the light at the end of the tunnel that every entrepreneur needs to learn how to keep in focus.

In this case, there was the recession that played a role making it easy to point my finger at a significant macroeconomic factor. But there were also a ton of other learnings that were equally important to recognize, including: the difficulties of trying to compromise across five different co-founders’ points of view, trying to monetize through advertising without a clear strategy and short-term thinking when raising capital. All of these factors led to the first-time-founder mistakes we made.

But you learn from failing. What doesn’t kill you really does make you stronger. After shutting down PickTeams, moving to NYC, and taking some time to reflect and figure out what I wanted to do next, I knew that I wanted to get back in the driver’s seat and start something else. Over the next several years, I ended up co-founding two companies, both of which are growing and doing well — General Assembly & Daybreaker — but I fully appreciate that I would have not been able to contribute the degree of value, leadership, and expertise to those companies without having been through the full life cycle of my first failed startup.

You will fail. But that doesn’t make YOU a failure.

Starting at a very early age, we are socialized to associate the idea of failure with being the worst possible thing. An “F” on a test, getting fired from a job, or flunking a class all conjure up visceral ideas of a horrific, irreparable catastrophe. It’s our instinct to avoid failure at all costs. But if you’re an entrepreneur, you need to be able to take on risks and experiment constantly —which opens up many opportunities to fail. To take on the burdens and repercussions of each decision can weigh tremendously on a person.  

This may sound daunting, re-imagine key business or product decisions as science experiments: Create a hypothesis and then test it through data collection. Learn from the process, do what works and keep experimenting as you go. This approach to opportunities or challenges helps you to make sound decisions.

There’s no escape from separating yourself from the business. Winning a deal is a win for the company and might even make you feel better as a person. Conversely, a loss weighs on your own self-worth. But look to Kevin Systrom — whose Burbn app was a dead end. He kept experimenting and eventually built Instagram. Persevere like Jack Dorsey, founder of two massive tech empires (Twitter and Square) who actually had a few crash and burn moments himself before hitting on products that worked. And hold your head up like my friend Kathryn Minshew, who sunk her personal savings into a big lesson learned before founding The Muse.

Failure and experimentation helped shape these and so many other entrepreneurs. From my experience, there’s a lot of self-awareness that comes with failure and it’s made me a better person and a better leader. Granted, I’m not suggesting that you fail on purpose for the sake of learning. Rather, accept the fact that failures are inevitable in startup life and every successful entrepreneur has been through the ringer on multiple occasions. Take time to grieve, take time to process, take time to gain clarity, and then take a step forward, armed with a deeper knowledge of yourself and what it takes to run a business. Will you be defined by your failures or will you be defined by how you grow and learn from the requisite stumbles along the way to success? The decision is up to you.  

Benjamin Khachaturian

I help entrepreneurs grow personally & professionally. Digital Marketer, Real Estate & Crypto Investor

10mo

Matthew, thank you for sharing this. I really appreciate what you're doing. If you're interested in connecting, feel free to send me a request.

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Russ Turner

Helping CEO,s, Entrepreneurs, and Business Professionals take charge of their Personal Branding.

6y

Embracing failure is the key, Matthew thanks for sharing this extremely enlightening article.

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Christine Janssen, PhD

Pioneering the world of immersive learning

7y

Music to my ears. I agree 100%. More people need to embrace failure and see it as a learning opportunity instead of personal defeat.

Megan Weinkauf, Ph.D., MBA

Through research-backed strategies, I guide my students and coaching/consulting clients to realize their full potential, and become leaders that positively influence people.

7y

Great article and incredibly inspiring. I will not be defined by my failures, I will grow and learn from the requisite stumbles along the way to success. :) Thank you!

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Roulla Yiacoumi

Managing Editor, Information Age, ACS

7y

Thank you for your brilliant insights. So many of us take failure very personally instead of seeing the lesson it taught. PS Small typo, if you're interested: it's through the 'wringer', not 'ringer' : )

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