The power law of venture capital dictates that only a small percentage (2.5% of all venture-backed startups) will go on to become unicorn: companies that redefine innovation and yield thousand-fold returns. Identifying these elusive outliers, and the founder most likely to start one, is both the challenge and the privilege of being in venture capital.
Several years ago, I discovered a book that forced me into deep self reflection on my life’s journey and offered me a new mental lens for identifying a class of founders with an increased likelihood of joining the 2.5% club: second mountain founders.
In his book "The Second Mountain," author David Brooks draws the analogy between life and mountain climbing. During our lifetime, most of us start and finish climbing a singular mountain. Reaching the ‘summit’ of this mountain involves the pursuit of the classical definition of success. We seek success through achievement and status. For example, attending specific schools, working for certain companies, having job titles, and accumulating wealth. The irony is that, while many of us eventually summit this first mountain, and achieve society’s definition of success, we often find the summit is, in fact, a false peak. Rather than self-actualization and accomplishment, we’re instead left experiencing profound disappointment (what Brooks calls the “arrival fallacy”). I have observed this first hand with many friend who are successful entrepreneurs. They achieve crazy levels of success early, but then struggle to figure out their next chapter (i.e., goldilocks paradox).
Second Mountain Founders
However, there is hope! As we climb that first mountain, we sometimes we catch a glimpse of a new peak on the horizon. We feel drawn to this new peak by a deep sense of purpose and meaning. Pursuit of this second mountain is a journey to serve something greater than oneself. Sometimes we must squint, change our orientation, or proceed on faith in order to pursue this new journey. The most challenging mountains are not conquered by following well-trodden paths and following-suit, those on a second mountain climb are likely to face trials and tribulations.
Second mountain founders are founders driven by causes and problems that are deeply personal. The pursuit of this new mountain is seen as their life’s work. These are founders in touch with what Boyd Varty dubs “the wild self”.
→ Note: I also highly recommend the book: The Lion Tracker’s Guide to Life
So what makes for a second mountain founder? It’s more than simply being mission-driven. Second mountain founders have a deep sense of obligation and see their entrepreneurial journey as a conduit to create meaningful change. It’s something that’s hard to fake. You know recognize it as an investor from the vibe, and feeling.
There are several traits further characterize second mountain founders:
- A Purpose-Driven Journey. Second mountain founders are motivated by a deeper purpose. It’s less about a specific market opportunity, or business model, and more about the personal nature of the problem. Second mountain founders seek truth, not external validation. As a result, they are biased to action, driven by an internal compass that helps orient the path forward. Urgency is often manifested by rapid execution and fast progress.
→ A great essay by Trea Stephens on “choosing good quests”
- Quiet Confidence & Inevitability. Second Mountain founders also operate with a sense of inevitability. They are comfortable with obstacles and uncertainty, because they are confident on their path. As an investor, you get a vibe that the founder is going to make this happen with or without your help. Many of the best founders I have backed projected a sense of inevitability in their quest from our first meeting. Not in off-putting or ego-centric way, but more from a place of quiet confidence. In part, this is driven by second mountain founders operating with with Ikigai, a Japanese concept that encompasses doing a combination of what you love, what they are skilled at, and what the world needs.
→ Note: The Courage to Be Disliked is another fantastic book
- Earned Secrets: Second mountain founders are deeply immersed in the realm of their ideaspace. These are individuals who have accumulated earned secrets from years of being in the trenches and having wrestled with the problems for years. This accumulated wisdom is often apparent from the founder’s growth mindset; recognizing their entrepreneurial journey as a marathon, not a sprint. They are prepared to persevere through the enviable challenges and setbacks, and find meaning in the face of adversity. The resiliency of second mountain founders drives their personal growth, unique insight and ambition. They are founders best defined by lines, not dots.
- Gravitational Force: Finally, second mountain founders are infectious. They have a natural ability to attract other talented folks into their orbit. These are founders who spark and lead movements. Despite operating with extreme drive and urgency, the best founders still prioritizing collective success over individual achievement. This mindset tends to attract other mission-aligned individuals and opportunities. This is a powerful gravitational force, and often results in a founder attracting impressive early employees, co-founders, or customers who otherwise wouldn’t likely take a chance on a startup.
In conclusion, while rare to find, the venture community would be well served in striving to identify, nurture, and invest in second mountain founders. If you find yourself resonating with the concepts above and feel driven by a deeper sense of purpose, you may be on the path of a second mountain founder. If so, please don’t hesitate to reach out.