8 Failed Startups, 5 Lessons Learned

I used to think college was the path for success... Then something happened. I was catapulted back into reality. I began freelancing at my first startup.

Photo: Joshua Fechter, freelance entrepreneur and Content Marketer at 22Social; Source: Courtesy Photo
Photo: Joshua Fechter, freelance entrepreneur and Content Marketer at 22Social; Source: Courtesy Photo

I used to think college was the path for success.

I had just finished earning my economics and political science degree and was close to finishing my third, in finance – all in five years. The idea of earning three degrees in the time it takes most people to finish one gave me unfounded confidence.

Then something happened. I was catapulted back into reality. I began freelancing at my first startup.


Startup Reality Check

I quickly realized I had zero applicable skills to help this company grow. The worst part: everyone else knew it too. Each day I walked into work afraid I would lose my job.

The founder was struggling to raise funding and technical mishaps started to delay the product launch. As I suspected, three months in, I was fired. Three months after that, the company’s founder gave up on his startup.

This process repeated itself eight more times until I finally landed at a great startup. I don’t know many people who are willing to freelance at eight failed startups to achieve their goals.

It sure wasn’t easy. Reflecting on what motivated me to climb from the depths of hardship to help make a startup successful, I came to these five conclusions:


  1. I realized success is not about me.

    Entrepreneurs who don’t achieve success have one thing in common: it’s all about them. I wanted to be successful so my mom wouldn’t have to work another day in her life, so I could donate money to charity, and so I could lead others to fulfill their potential.

  2. Keep the feeling of accomplishment in mind.

    The desire to feel what it’s like to see charities react to donations I make, startups become successful from implementing my strategies, and my mom’s face from finding out she no longer had to work is awe-inspiring.

    Part of the satisfaction that comes from achieving your goals is a renewed confidence that you can go above and beyond the next time around. If you can see this feeling waiting for you at the finish line, you’ll work harder to make things happen in your favor early on.

  3. Read like you live in a library.

    It’s easy to get down on yourself. Whenever I found myself bogged down by negative thoughts, I opened up informative and motivational books. Reading prevented negative thoughts from taking a foothold in my mind and gave me the inspiration, creativity, and determination to take control over my life. The works of great authors and entrepreneurs like Dale Carnegie, Peter Thiel, and Seth Godin can inspire anyone to keep pursuing an extraordinary life.

  4. Be willing to give up your closest friends.

    One of the hardest things I had to do to become successful was to let go of friends who slowed me down. I quickly realized after leaving my third failed startup that I needed to concentrate more and put in additional hours. I couldn’t have friends who texted or called me asking to go to parties.

    I needed friends who could teach me useful business strategies or open doors for me. It sounds harsh, but that’s the reality of success. You need to surround yourself with others who want it just as bad—or even more. So, if you really want to help a startup become successful, or eventually start your own business, lose everyone who acts like an obstacle.

  5. Always speak out for what you believe.

    The biggest mistake I’ve made is not speaking out when it mattered most. I kept my mouth shut when I knew answers that could improve a company’s performance. Why? I was scared of rejection.

    If you believe in your ideas, always speak out. Without risking huge failure, you won’t ever have huge success. As soon as I started talking more about my failures, successes, and ideas, I found confidence in standing up for myself. As a result, I received more respect and responsibility.

Remember, failure doesn’t last forever if you stay motivated and make sure to learn with each step you take.


This article has been edited and condensed.

Joshua Fechter is a freelance entrepreneur and content marketer working on next-generation Facebook marketing software at 22Social. Josh is a serial entrepreneur, having worked at over ten startups. He also helps clients with branding and building 6-figure online businesses. He blogs at Digital To Community about what it takes to become a leader in the digital world. Connect with @joshuafechter on Twitter.


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