Hey Founders- It’s OK If Things Don’t Go As Planned

Thursday, March 19, 2015 2 No tags Permalink 1

A few weeks ago, I met up with a friend who has his own startup. I could see from the look in his eyes, things weren’t going well. He was exhausted, burnt out after years of hustling without seeing the outcome he wanted.

I recognized his pain and told him what he needed to hear- “It’s ok. You’re not a failure. So what if things didn’t turn out the way you expected? You learned a lot, and this isn’t your last company.” His eyes lit up, and I knew I had to spread the word to other founders who were feeling like failures.

Last year, I was in a similar position. My own startup, matchist, wasn’t going as planned. We had won New Venture Challenge at Chicago Booth, but we hadn’t been able to pin down the customer acquisition model we needed to grow our startup. Tim, my cofounder, had taken a full time job months before and I was faced with the tough decision of figuring out my next steps: continue working on matchist, or pursue a few other opportunities that presented themselves.

The biggest part of this realization was coming to terms with the fact that my business wasn’t a success. As a founder, I hadn’t succeeded in the way I imagined. But, the things I realized were that this was totally fine. Lots of people have to go up to bat multiple times before hitting a home run. While I felt like a failure, those around me- friends, advisors, family- didn’t see me that way. And over time, I came to realize they were right.

Life moves on, and if you’re a founder, you’ll do it again. I also realized that you don’t have to be CEO to be part of a startup’s success. About 6 months ago, I joined Trello to head up marketing. While I was not anywhere close to being founder (more like 20th employee), I still felt enormous excitement and pride at being part of the startup’s success, and feeling like it was part of my own.

This was my state of mind when I sat down to talk to Amina Elahi from the Chicago Tribune. I wanted to share with other founders that even though they hear success stories all day long in the media, there is a more important message of what happens to the others startups and founders who aren’t written about. I shared our story frankly- in a positive perspective given the months of introspection I’ve done. I really wanted other founders to know it was OK- life moves on.

That part of the message was somehow lost, so I want to make sure I do my job of sending that message to other founders, which was my reason of talking about something not so pleasant publicly.

  • Chris Lynn
    April 22, 2015

    Hey Stella,

    I got here after looking at your inspiration boards on Trello (I love Trello).
    I went to Matchist to see what it was all about and thought. Wow! I have a couple of projects that need exactly this kind of service.
    I started to go through the process and very quickly discovered why you may have had problems getting this to “take”. Feel free to contact me if you’d like to get my perspective on your startup.

    A litlle about me. I too am a serial Entrepreneur who, currently works as a Business Analyst/ IT Project Manager in Healthcare.



    P.S. I have an idea for another inspiration board. How would I add one to your Trello Org?

    • Stella
      August 24, 2015

      Hi Chris- Sorry to just be getting back to you. Easiest way to get a board added is to tweet us @trello. And feel free to email me your ideas- startupstella at gmail. Thanks!

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