Startups Seeking Sherpas

After we sold our startup Sombasa Media just over a dozen years ago, I embarked on two distinct “journeys.” The first was a month-long 1500+ mile cycling trip from the southern tip of England to the northern tip of Scotland (“Land’s End to John O’Groats”). The second was a trip where we hiked the “Inca Trail” in Peru to Machu Picchu. Both trips “rhymed” with each other in that the point intentionally was about the experience of the voyage rather than merely the destination itself. I think that the reason founders are attracted to entrepreneurial endeavors often stems from the same intrinsic motivations. It’s not fully about the eventual outcome or exit of the business (— yes, of course that matters), rather the process of creating something out of nothing and building a meaningful endeavor.

There are many differences between the two trips which I took, including that the cycling trip was a solo endeavor and the hike was a group one. But this isn’t an analogizing blog post about having “co-founders.” It’s one about having a sherpa. Obviously, I don’t mean literally a cultural Sherpa… but instead a sherpa who is a largely silent but proactive guide providing support along the journey.

Yes, my analogy description of a sherpa very much sounds like a mentor. But I think that there are subtle distinctions:

  • A mentor has been down this path previously; a sherpa has traveled the road too many times to count.
  • A mentor walks beside you along the way; a sherpa is often running ahead to help clear the path.
  • A mentor actively talks through the issues and challenges at hand; a sherpa foresees the challenges ahead and positions the journey for you to help overcome them.
  • A mentor is interested in both your personal growth as well as success; a sherpa wants both but also feels duty to protect when calamity is near.
  • A mentor brings a set of expectations about the relationship; a sherpa often surprises you with his involvement (or intentional lack thereof at times).
  • A mentor is typically one or two stages ahead in (career) experience; a sherpa has seemingly been doing this forever.

All along my professional career I’ve aggressively proactively sought mentors to help with the journey. However, it wasn’t until we started NextView a few years ago did I (along with my partners) find sherpas who possessed an extremely generous willingness to help in building our firm, and I discovered a kind of advisor which was really different. Startup founders similarly look to bring in outside help with both formal and informal advisors into the orbit of their companies. While accessible mentors should and do play an invaluable position, I think it’s helpful for entrepreneurs to also seek and individuals who can play a sherpa role. An unexpected clearing of a path ahead rather than just a warning about an obstacle can preserve energy and resources for bigger climbs ahead. And the wisdom from someone who grew up on the mountain rather than just someone who “knows” it is invaluable.

David Beisel

David Beisel is a co-founder and Partner at NextView Ventures. He has been focused on early stage Internet startups his entire career, both as an entrepreneur and venture capitalist. As an investor in the digital media space, David was most recently a Vice President at Venrock and previously a Principal at Masthead Venture Partners. Prior to becoming a venture capitalist, David co-founded Sombasa Media, an e-mail marketing company best known for its flagship product BargainDog. Sombasa was successfully acquired by where David served as Vice President of Marketing. David holds an MBA from the Stanford Graduate School of Business and an AB in Economics, magna cum laude and Phi Beta Kappa, from Duke University. He also founded and leads the Boston Innovators Group, an organization which holds quarterly entrepreneur events drawing a thousand attendees.