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Any time you take a chance you better be sure the rewards are worth the risk because they can put you away just as fast for a ten dollar heist as they can for a million dollar job.
// Stanley Kubrick
I flailed at my phone with futility, attempting to silence its incessant alarm. I had no idea what time it was or how long I had been sleeping. It was the week before Christmas, and I had been living at my desk since Thanksgiving, working every waking hour and napping on the cheap brown couch next to it when I needed to wait for simulations and experiments to run.
Both my sleeping and working arrangement during our first “deal season”
It was our first year of operations at Envelop Risk, just a few years after I abandoned a relatively safe Fortune 100 job to pursue this glamorous lifestyle. I designed and developed our technology and was now also responsible for operations as we worked to get our company off the ground. Envelop consumed my every thought, regardless of what was actually going on around me.
Apprehension and doubt
One evening my young son excitedly ran up to show me his new sabretooth tiger toy, mispronouncing its name. That’s it… CyberTooth! That would be the name of our model. Once again, my mind had turned back to work. Whether physically or mentally, I had missed most of the holiday season with my family.
The stress, uncertainty, and long nights were overwhelming. The log from my watch showed that my average bedtime over the previous month was 4:24 AM. Was it worth it? Should I just return to my safe 9 to 5 corporate career? The future of Envelop was uncertain, and all the work and sacrifice could be for nothing.
Hope
My motivation was freedom – to establish success early in my career so that I could then chart my own course and not sacrifice any more holidays or big moments. My son might not have been able to understand why I couldn’t take a break to watch The Grinch, but it was also my responsibility to provide him with future opportunities. I struggled to balance the present with the future.
I wasn’t just accountable to my family; my co-founders were making big sacrifices too. Nothing great is achieved without effort and risk, and another opportunity like this might not ever come. If I was ever going to take my shot, the time was now. At this point in my career, even if we failed the experience alone would be invaluable.
I had fought through exhaustion in multi-day endurance races before, and the lessons from those challenges were paying off. Relentless forward progress – one foot in front of the other – was the only way to push through the rest of this rough patch.
Turning the corner
I spent most of the week after Christmas in bed recovering, my mind and body completely drained. I knew I couldn’t continue like that every year. I would not fall victim to the sunk costs fallacy and miss my kids growing up entirely.
I remember going to see lights on Christmas evening, and trying my best to be jolly while feeling absolutely miserable
A few months later my family and I moved to the UK. At Envelop, we began expanding our team and gradually the risks and personal costs diminished. The returns on that early investment became clear – not just financially, but in experience gained and relationships built for both me and my family.
Today, Envelop is a mature company employing over 50 people, with a high priority placed on the wellness of staff. I share this story not to glorify overwork or burnout. In the long run those are counterproductive and unsustainable. Without realizing it, we can drift into a cycle where the ends no longer justify the means, squandering our most valuable resource – time – on diminishing returns.
But sometimes, we need to shoot our shot.
John Kelly is the original architect and developer of Envelop Risk’s core technology, CyberTooth. After spending a few years in the UK building the team, he now lives back in the US with his family. John is also an internationally recognized ultra marathon runner, one of only three people to complete the Barkley Marathons more than once and holding the speed record on many well-known routes, including the Pennine Way. The thoughts and views in these posts are his own reflections from experiences as an accomplished athlete and entrepreneur, and do not necessarily reflect the views of others at Envelop Risk.
