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At first glance, it may be hard to imagine similarities between tech startups and running marathons. A few months after starting at Scale, I completed the Boston Marathon, my ninth marathon to date, and the parallels were clear: both are ultimately endurance sports where crossing the finish line can happen only after navigating through many milestones and a great amount of energy, emotion, and unpredictability.

Every startup’s journey happens in its own way and is a different experience for each person involved. In the early miles, developing a core product, determining product-market fit, and simply holding course can require perseverance through many experiments and unsuccessful trials. At my previous company Box (disclosure: a Scale portfolio company), we took many different approaches to building out our go to market strategy around sales and marketing [many things worked, many didn’t], before finding a model that was truly scalable. The same could be said about my experiences at Tilt. While these were challenging stages for those involved, in broader scope, every step was critical in finding the momentum that would propel the company ahead over the long term.

Marathons are engendered by an oddly similar set of characteristics, they are also long journeys with steep roads and elusive final destinations. They involve a considerable amount of energy, intense focus, and a willingness to persevere through the unforgiving and often unexpected. Runners will prepare endlessly – train properly, hydrate accordingly, and study the course, but until they’re in the middle of the race, predicting how they’re going to feel [both physically and emotionally] is nearly impossible. And perhaps even more challenging is that there’s no owner’s manual, app, or even good advice that can be used as a frame of reference. Similarly, each journey, even for the same individual, is a unique and very personal experience.

For startups, keeping pace and finding momentum can be difficult when forging into a new market or entering an existing space with a novel approach [which many startups often do]. Within the Scale portfolio, Docusign is a prime example of how a company can simplify workflow for businesses of all sizes. The Company is competing on a landscape that is older than John Hancock, but the Docusign team is adding a level of ease and simplicity to a well-known problem area within the enterprise that we have yet to [or rarely] encounter. Or Hubspot, which continues to reinvent the marketing funnel for SMBs by helping convert new business from inbound traffic, has needed to build [and sustain] momentum to keep an edge on names that have been controlling the industry for many years. Without question, all of the companies within our portfolio that have successfully scaled have faced headwinds along the way. Any hyper-growth entrant with great expectations will almost never do so uncontested, just as any aspiring runner aiming to clock a competitive time will not do so without fierce competition.

In both tech startups and marathons, conditions often change unexpectedly. Within startups, Sales may miss their goals, Product might delay a highly anticipated launch, key leadership may transition from the company. During marathons, roadblocks happen, too. Physical exhaustion, dehydration, or feelings of overwhelming uncertainty may suddenly set in. These moments become significant barriers for many. For others, they become the richest learning opportunities and a place where perspective is built. Slowing down to speed up, as some say. Within marathons, dialing back the speed to regain focus or rejuvenate the body. Within a startup, easing back the pace [or cash burn] to produce more sustainable growth. Ultimately, in each case, the goal is to hit as many successive milestones as possible to keep the journey going.

And it may be this same set of milestones that will dictate the company’s performance going forward [or for a marathon runner, the remaining miles of the race]. Just as teams within a startup carve out market share one milestone at a time, marathon runners persevere through each step, crossing the finish line mile by mile. And although tech startups and marathons can be challenging – and sometimes unforgiving – work environments, crossing the finish line is worth every bit of hustle along the way.


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