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Introduction The Despondent Founder

In the mythological epic, Mahabharata, the narrative begins with its warrior-hero despondent, dejected, and frozen in the middle of a battlefield. Enemy armies surround him. He needs to act. Yet he is overwhelmed. Written in circa fourth century BC, such a timeless story about a warrior-hero, could very well be about the modern day entrepreneur.¹ One who often feels lost, confused, and despondent. Unable to apply his mind, stuck in a funk. Like a Formula One race car that sputters and coasts slowly to the side, he stalls.

      Meanwhile, the commercial battle rages on. Payroll needs to be managed, cash is low, competitors are chomping at the bit, and the team needs motivation and guidance.

      Why do entrepreneurs make a conscious choice to jump into the battlefield, to put themselves in positions that most would not dare to? We know that at a deep level, all entrepreneurs are fundamentally abnormal, even irrational, because rational people rarely try to change the world. The irrational spirit is aching to fill a void, both in their psyches and in society. They suffer from cognitive dissonance, which is a fancy term for beliefs or behavior that are inconsistent. The odds are stacked against them. Start-ups fail at a very high rate, as much as 90% or more, yet entrepreneurs choose this path. We wonder why.

Working against all possible odds and every possible challenge, the founder chooses this form of self-torture in promise of a reward. She decides to leap over hurdles of innovation and technological development, building teams, gathering resources, selling products, ensuring growth, retaining healthy gross margins, defending her turf against competition. Under immense pressure to perpetually grow at a rapid pace, start-up founders are encouraged, expected, and cheered on to pump up revenues and valuation to keep the motivation and the momentum. If growth drops, everything scatters. People escape. Investors flee. Down rounds occur, and the company is declared as damaged goods. Pressure extends over into publicly traded companies, as the CEOs live and die by their quarterly earnings guidance.

      While aiming for hypergrowth, the founder undergoes a stressful journey managing the unknowns of developing products, go-to-market tactics, managing sales momentum, attracting high-performing teams, raising capital, fending off acquirers, and beating the competition. If start-ups are the new war zones, the founder is not fully prepared to wield the weapons with courage, and finds herself pushed over the top, burned out, exhausted, afraid – a wounded soldier. Those who chanted the “move fast and break things” mantra find their own psyches broken. Founders have now started to open up and publicly describe the toll of the start-up journey.

       I recently chose to step down as CEO of the technology company I co-founded … It wasn't an easy decision; ongoing struggles with mental illness and a desire to prioritize my mental health were the primary drivers of this choice.

— Matthew Cooper, co-founder, Earnup ²

      In my research for this book, over 150 founders and business leaders opened up to share their own journeys in these dark domains of stress and depression. They have provided answers, which have been encapsulated into these chapters.

The following pages are voices of the founders who have often struggled to understand how to seek help, while being at odds with the demands and realities of running their businesses. Should we soldier on silently, fighting these demonic battles alone? How should we seek therapy in the chest-thumping, macho, passion-driven start-up world? How should we respond to the classical loaded question–answer greeting “So, how is it going? Crushing it, aren't you?”

      Should we “always be crushing it” and then one day our selves feel crushed? Simone Weil, the French philosopher, urged that the only suitable question to ask another human being was, “What are you going through?”

PSYCHOLOGICAL QUOTIENT – AN INTRODUCTION

      This book is a rough guide to developing awareness of your inner resources; you could call it your psychological quotient. Just as we have developed frameworks for IQ and EQ, knowing a bit about our own psychology can help develop emotional resilience. Even possibly address the unspoken challenges of depression in any business leader's journey. Most entrepreneurs often struggle with the dark nights and suffer from anxiety, depression, and breakdown. Some get help; they keep going. Some train themselves to get out of the funk. Some give up. Like any grueling marathon, the number of people at the finish line is far smaller than those at the start.

       Starting a company is like eating glass and staring into the abyss.

       — Elon Musk

We know IQ and we know EQ – the impact of our intellect and emotions in the world of business is well understood. Psychological quotient can be best defined as the ability to identify and develop our inner resources – the ability of entrepreneurs to tackle challenges and flourish. With psychology and the study of our behaviors, we can identify and eliminate subconsciously self-constructed barriers and skillfully navigate the game of business. And if our resources fall short, how should we identify early warning signs of our flailing mental states? Is this burnout? Is this depression? Where is my “battery about to die” sign? What are some tools and techniques to build self-awareness of our psychology and build endurance? When the waves of external stress factors engulf the founders, we find we can no longer swim as skillfully as we once did. “It never stops,” says one founder. The competition is trying to kill you, your team members are arguing, asking for raises and everyone wants to be on a CEO career path,” says one founder. Although we cannot control the external factors, how we perceive and react to them is the heart of this game.

      In the following pages, we will explore lessons of endurance shared by over 150 founders – how they wrestled with the dark angels, one day at a time, and reached the other side. We live in a world where passion is an overblown fetish. Bravado and chutzpah is the only currency of champions. Emotions are buried deep. To express the full range of our emotions would be considered unprofessional, weak, immature.

      Amidst these social constraints, these founders share their authentic and honest insights. Theirs is the real bravado. In sharing their journey, they offer strength, solace, and guidance. While founders who absorb these lessons may benefit, I believe it can also provide some guidance to the investor community. For venture capitalists, the ones who have gladly provided the ammunition for the disruption wars, encountering the wounded soldier is somewhat uncharted territory. We thought we were being helpful, strategizing, connecting, adding value, cheering, supporting, but how did we get here? What stance should an investor take when founders reach the end of the rope? Instead of pointing the founders to the nearest friendly therapist, or funding the next meditation app, how can investors take a proactive approach to address the crux of the problem?

In putting this book together, my somewhat meager attempt to highlight the importance of psychological

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