The Resilient Founder

As acclaimed investor and entrepreneur Ben Horowitz once stated, managing your own psychology is the hardest skill for any founder or CEO. In The Resilient Founder: Lessons in Endurance from Startup Entrepreneurs, Mahendra Ramsinghani gathers insights from over a hundred founders to deliver an intuitive and insightful guide to understanding our psychology and navigating the psychological pressures of startup leadership.

Venture backed companies are expected to grow at high velocity, raise large amounts of capital, build teams effectively to achieve unicorn, no decacorn status. Yet the journey is long, filled with uncertainties, extremities and black swan events. It can wear out the best and the brightest. On the outside, a CEO can demonstrate sheer bravado, an invincible spirit as they behead dragons in the business battlefield. And on the inside, they deal with their dark side, subconscious struggles, emotional barriers, shame or guilt. The role of a founder can be lonely, frustrating and filled with high-highs and low-lows - all of this leading to anxiety, depression even suicide.

This book addresses the fundamentals of understanding our own inner workings and explores practical ways of overcoming our inner hurdles. Filled with simple, yet concrete strategies, lessons and insights, founders and business leaders can work with stress, anxiety, and other mental challenges presented by the life of an entrepreneur.

In this book, readers will learn to:

• Understand the basics of founder psychology, and how our inner workings can help or hurt us
• The importance of building a healthy ego, leading to resilience
• Draw on the lessons of established startup leaders on how to wrestle with their own mental and emotional challenges

Written for founders, entrepreneurs and Chief Executive Officers, The Resilient Founder leads a gentle path to self-awareness, compassionate soul-care and inner wellbeing. Entrepreneur, Investor and author Brad Feld calls this book "dynamite". Case studies, philosophical perspectives and a generous dose of poetry is sprinkled across this book, which can be a companion for all those misfits, rebels and the crazy ones. For all those perpetually hitched on the roller coaster ride of entrepreneurial journey, this book is first of a kind to delve into the dark side and present a balanced approach to building your inner core as you build your company. This is no quick-fix guide, and we are perpetual work-in-progress. Today is Day One. Let us start the journey.

Foreword xi

Acknowledgments xv

About the Cover xvii

A Note to Readers xix

Introduction-The Despondent Founder 1

Part I Running to a Standstill 9

1 When Suicide Seems Like a Good Option 11

2 Stepping Back from the Edge 29

3 How External Events Trigger Negative Feelings 39

4 Obstacles and Frustrations 47

Part II Understanding Our Psychology 55

5 Building Our Psychological Quotient 57

6 Ethics 65

7 Do the Right Thing 71

8 Ego – The Emperor and the Slave 79

9 Working with Your Ego 87

10 The Hidden Land of Desires and Motivations 93

11 Logos and the Mind 105

12 Pathos: Belief Systems 117

13 Putting It All Together 123

Part III Reassembling the Furniture 127

14 Toward Building a Healthy Ego 129

15 Psychotherapy: An Imperfect History of an Impossible Profession 143

16 Fearing Our Own Selves … and Other Mental Blocks 149

17 Stages of Therapy 159

18 Challenges and Pitfalls in Therapy 165

19 Medicating Our Way to Recovery 173

Part IV These Rituals Worked for Us 183

20 A Soul Made Cheerful 185

21 Prescription 1 – An Organized Diminution of Work 193

22 Prescription 2 – Get Out of Your Head 199

23 Prescription 3 – Feeling, Not Thinking 209

24 Prescription 4 – Spirit over Mind 217

25 Prescription 5 – A Promise to Yourself 233

26 The Elements of a Good Life 239

Postscript: How to Care for the Broken and the Depressed 245

Appendix I: A Founder’s Mental Health Manifesto 261

Appendix II: Founders’ Voices and Anonymized Surveys 263

Notes 265

About the Author 271

About the Website 273

Index 275

MAHENDRA RAMSINGHANI, B. Engg., MBA, authored this book as an empathetic attempt to support the wounded entrepreneur — the silent soldiers struggling on the startup battlefield, fending for themselves as they recover. In his fifteen years of investment experience, he has seen first-hand, the struggle with the siren call of startups. He is the author of The Business of Venture Capital (Wiley, 2021) and co-author of Startup Boards (Wiley) with Brad Feld and Matt Blumberg. His articles have appeared in MIT Technology Review, Forbes, and TechCrunch. He is the founder of Secure Octane, a San Francisco–based venture fund and has advised sovereign and corporate venture funds in the United States as well as the Asia-Pacific and Middle East regions.

Founders, entrepreneurs and business leaders, especially those who shoulder responsibility for high-growth, fast-moving startups, often struggle with stress, anxiety, depression, and other mental challenges as they race to reach the promised unicorn land.

In The Resilient Founder: Lessons in Endurance from Startup Entrepreneurs, veteran venture capitalist and entrepreneur Mahendra Ramsinghani delivers an eye-opening exploration of the relentless emotional pressure faced by startup founders and business leaders. The book draws on lessons in endurance from over one hundred company founders who share their own emotional difficulties.

The art of building resilience starts with the basics of psychology, and the importance of developing a healthy ego. Be it the pandemic, competition, or cash flow, crises are bound to occur. Why do some founders react differently, while some succumb to pressure? What about therapy and medication? The book provides a simple and a holistic framework towards improving the well being of those under the gun at high-pressure startups. The postscript outlines how to support all those who suffer from depression as a result of their entrepreneurial PTSD.

Filled with insights, tactics, solace, and guidance from those who have already endured the slings of startup life, The Resilient Founder is a first of a kind compassionate companion for empowering entrepreneurs. Because our society needs the innovators, the founders, the misfits, and the crazy ones to not just survive, but to thrive.

Advance praise for The Resilient Founder

“The Resilient Founder is the first step and essential guide in supporting founders through the dark nights of the startup journey. We understand valuations, cap tables, and exit multiples, yet we don’t fully understand the mysteries of our mind, how it builds its resilience muscle or why it breaks down. This book highlights the importance of protecting and strengthening our inner core.”

—SCOTT KUPOR, Managing Partner, a16z and author of Secrets of Sand Hill Road: Venture Capital and How to Get It

“The Resilient Founder is an important work precisely because it speaks to the most taboo subjects in leadership: depression, burnout, and, heartbreakingly, suicide. Mahendra Ramsinghani, bravely, wisely, intensely leans into the subject seeking answers to what helps founders withstand the vicissitudes of the entrepreneurial life. Too often such topics aren’t discussed leaving those who struggle feeling bereft, broken, and alone. You are not alone and this book proves that. Every founder should read this book. Indeed, every founder and everyone who loves them.”

—JERRY COLONNA, author, Reboot: Leadership and the Art of Growing Up.

“As a 5X entrepreneur, and an investor in over a hundred startups, I know the founders journey pretty well. It has its highs. This book can help manage the lows. It doesn’t offer a quick fix silver bullet but starts with helping us understand our psychology. And explores pathways towards building resilience. We are all fragile. This book is the first step towards antifragile.”

—JOSH LINKNER, author of two New York Times Best Selling books, Disciplined Dreaming and The Road to Reinvention.

“In this day and age of unicorns, beneath the surface founders are dealing with extreme challenges. This book offers insights on how to not only understand — but also effectively manage the founders most important resource — their own psychology.”

—HARRY STEBBINGS, Founder and Managing Partner, 20VC