Rising From the Ashes

Article by:

Jesse Proudman
EO Seattle
Jesse Proudman - EO Seattle

Last month marked the twelfth year of my journey at Blue Box, a managed hosting company I bootstrapped in my dorm days at the University of Puget Sound. We’ve had tremendous success over the years and more than a few days in the gutter. The past few years, especially, proved very challenging.

In 2011, I made the difficult decision to fund the next chapter of Blue Box, and by the following October, closed a US$4.3- million initial investment. Everything was going great … until our largest customer left in December, taking 30% of our revenue with them. Three months later, we discovered embezzlement by an executive, which required an exhausting six-month repair.

To say this took a toll on my personal and professional life is an understatement— I was a wreck.As entrepreneurs are known to do, I clawed my way back from the bottom. But unexpected revenue loss and other distractions translated into unmet sales goals. We were forced to raise a convertible debt bridge loan, followed by a structured debt deal, in February 2014. If you’re nodding your head right now then you can understand how this process left me wildly depressed. I needed to mentally get back to where we all want to be: excited to tackle new challenges every day.

Here are a few approaches I took that helped me reposition my business and life:

Communicate Effectively

You’ve probably heard the expression, “Work smarter, not harder.” Communicating with the closest people in our lives is no different— it’s simply a matter of approach. As Brad Feld notes in his book, “Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur,” communication with our spouses can be one of the most challenging aspects of being an entrepreneur. His book gave me a blueprint of specific ways to interact at home without burdening my wife and family with my many professional struggles. Most crucial for me was being able to communicate my emotional state of mind, allowing those around me to understand the pressures of entrepreneurial life. I highly recommend adding this book to your reading list.

Commit to Being Well

It sounds obvious, but one of the first things I cut when the going got tough was proper self-care. That was a mistake. Shortly after my emotional dive, I reached out to my physician and a counselor. Having trained professionals to ask difficult questions and act as sounding boards proved wildly helpful, as did modern pharmaceuticals. When you don’t feel well physically, it’s hard to feel well emotionally. Also, when I began exercising consistently, I began to see a huge difference. Eating healthy meals and getting enough sleep were other necessities that I shouldn’t have taken for granted earlier but did.

Rediscover Your Passion

In November 2013, I read two entrepreneurial biographies that helped me get back on the right course: “The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers,” by Ben Horowitz, and “Steve Jobs,” by Walter Isaacson. Both books are about wildly successful individuals who went through hell and back to grow their companies. Horowitz’s story, in particular, is strikingly similar to that of Blue Box’s. For me, though, the details and outcomes of their stories were irrelevant. Just like my Forum experience, their testimonies helped me find commonalities and come to the realization that I wasn’t alone. Also, I learned that behind every successful startup there lies a certain measure of turmoil and catastrophe. Knowing this inspired me to start working on my passions again. I replaced myself as CEO, and the company benefitted immensely because I was back to working where I belonged.

Rising from the ashes is a part of what can make the entrepreneurial life worthwhile, but it is only rewarding if you are mentally present to witness it. I’m proud to say that IBM acquired Blue Box in June to leverage its technology platform as part of the company’s private cloud strategy. This marked the end of one personal and professional journey, and the beginning of the next.

Jesse Proudman is an EO Seattle member and the CTO of Blue Box, an IBM company and Seattle-based cloud provider. Jesse is a proud father who races cars in his spare time. Contact Jesse on Twitter at @blueboxjesse.

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