What is your Big Why?

investor profile

February 09, 2026

by an investor from Wesleyan University in Dedham, MA, USA

“Why are you here?” “What is my gift to the world that I need to get out there?” Whenever I interview potential searchers, search CEOs, or search investors, I ask a million questions all geared towards one question, really: "What is your Big Why?” There is no final answer. It is refined through experience, getting deeper and deeper through time. Life Goals, motivated by your BIG WHY, are impossible to complete. But you have to start somewhere. I have come to the centrality of unconditional love and true humility in life. These concepts are thrown around a lot but are rarely understood deeply. Neither idea is a destination, but rather a practice, embraced but never perfected. My gift is the experience of extremes. Extreme success and failure. In business, in athletics, and in my personal life. I have been to the mountaintop, and God knows I have been to hell, too. My calling is to mentor and explain at least some of this to younger people so perhaps they don't have to suffer the way that I did, that they don't have to feel as alone as I did most of my life, that they can begin to sort out the false messages and promises they are being fed day in and out, and think for themselves about matters on this earth more deeply than greed and ego, the skin deep fetishes so beloved by our society, but that led me to so much misery. All of this comes through my passion for sponsoring men in AA, teaching this class, and mentoring young CEOs and searchers...ultimately to model unconditional love and humility. So they and you can begin to see and feel your why, too. This is a day-to-day, sometimes moment-to-moment, experience of grace, suffering, and learning for me as I continue to refine and live out my Big Why. Last week I met with two young men. Both handsome and brilliant. But from elite colleges. Identical in age. One is a potential ETA searcher seeking counsel, the other a physics prodigy seeking comfort. The searcher, like so many other young CEOs I have encountered, led with brash arrogance. I tried and tried to speak radical truth to him. But he wasn’t ready. Many, many times, the drunk has to drink some more, and the arrogant CEO can’t allow himself or herself to be vulnerable, to admit their ignorance. Fear is always there, but they hide from it, peacocking as if that will work. All I can do is plant the seed. And hope it will take root at some point later. Many, many times it does. But not on my timeline. It is often, frankly, well after I have given up all hope. Those miracles sink deepest into my heart. The physics prodigy was shaken, suffering, but in a way that cracked him open. A mixture of pot, AI, and mental illness had obliterated all his plans for 20-something greatness. His story had me on the edge of my seat, because I have seen so many times that, out of such devastation, truth and a firmly planted Big Why can emerge. He had been locked up in a mental hospital twice, gotten sober in AA, and was still receiving ECT (shock) treatments when we met last week. He was shaky and had some memory loss. But I could see something remarkable in his eyes: hope. The two young men are not very different, honestly. Both needed unconditional love, radical honesty, and someone who could model humility even as each battled their demons. Two of many that I have come to see as my Big Why. This is a safe space and community. Our most important mission is to try to give a voice to our why, to be vulnerable, and speak the radical truth while being respectful and supportive of all other members here. Remember, there is no good or bad, right or wrong here. In this realm, all that matters is honesty from the heart, not the head. What is your Big Why as far as you have been able to figure it out so far?
22
21
954
Replies
21
commentor profile
Reply by a searcher
from California State University, Long Beach in Delray Beach, FL, USA
For me, My Big Why are my kids. I model for them growth and contribution, constantly learning and transforming and always finding opportunities to add value to people around me. I enjoy building systems in business and in the family that create stability, ownership, and agency for other people. I grew up around enough volatility to know what the absence of structure does. Business acquisition became less about “buying companies” and more about creating durable platforms where people can operate, grow, and not feel trapped. On the surface, I facilitate and teach acquisitions. Underneath, I’m trying to help operators avoid preventable pain: Buying ego instead of cash flow. Confusing growth with leverage. Building businesses that own them That’s probably my current version of my Big Why: Build, mentor, model growth and contribution
commentor profile
Reply by a searcher
from University of Oklahoma in Oklahoma City, OK, USA
This is one of our #4 company core values! "Driven by Our Why" Driven by Our Why We each know our own unique “why,” a personal purpose we hold true with unwavering conviction. This “why” compels us to go beyond, time and time again, fueling our actions with relentless passion and meaning.
commentor profile
+19 more replies.
Join the discussion