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The Rollercoaster of Startup Life

In our business of supporting startups, we experience so many ups and downs. We also live vicariously through the founders and execs we support. It’s thrilling.

And also exhausting.

In my current state, I feel in supreme control of my company and these emotions, and I’ve found perspective and balance in my work and life. But that wasn’t always there. Any founder or startup employee knows it doesn’t always feel wonderful on this journey. And that’s OK.

Cracking Under Pressure

When thinking about the rollercoaster of startup life, I picture myself back in the scaling journey of Dyn circa 2015. To the outside, we were building a monster success story, but I was feeling the fragility of the opportunity in our grasp more than any other.

I feared that what was once an inevitability — a strategic exit or IPO — was losing its certainty.

So many lives, careers and balance sheets were on the line. I didn’t feel supported by my board or CEO. Everyone with visibility to our challenges felt the pressure, but I knew I was uniquely suited to persevere, figure it all out and ensure we ended up on top. Because of that, the walls felt like they were collapsing around me, and it was tough to regain the confidence and control that enabled me to get into my seat in the first place.

I started to crumble. Nobody but me knew at first, but once I began to develop migraines for the first time in my life, it became impossible to hide from.

This seeming lack of control created immense anxiety and stress, leading to a demise in my mental and physical health. I still remember missing a Fourth of July parade, laying in bed all day in Florida on vacation and sitting through Christmas-present opening with kids euphorically yelling while I had a piercing headache.

It wasn’t just my head. I had a constant, uncomfortable pit in my stomach. I hated it. I hated how I felt. I hated how I was dealing (or not!) with it.

Getting Help

So, what did I do? Well, after I got an MRI on my brain and ruled out any brain tumor or the like, I went to a mental health counselor.

Yes, I went to therapy. I listened to soothing audio programs in that office, in the dark. I sat on a couch. I got help.

Last week was a busy and high-stakes one at York IE, as we hosted our annual investment partner meeting, prepared to announce our sixth investment cohort and more. As I closed out the week, I opened the gift box my wife Katie gave me on the day we closed the Dyn acquisition to Oracle, and I read the note my counselor wrote to me:

“See & feel your accomplishments.”

Katie said to me back then, “Wow, you really did make your dream come true.” She had a front-row seat to it all and knew the thrill and relief that came with the acquisition. I open this box when I need a reminder.

Through sheer will, a tremendous support system, loyal team members and a heck of a lot of perspective and balance, you can figure out the challenges of startup life too. Be sure to find time for yourself!

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