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- Herausgeber: John Wiley & Sons
- Kategorie: Fachliteratur
- Sprache: Englisch
Unlock the secrets of business resilience in this indispensable survival guide
In a world of disruption and uncertainty, Still Standing: What It Takes to Thrive and Innovate in a Messy World by Cherry Rose Tan emerges as a beacon of resilience, offering the essential strategies for navigating the pressures of building and leading our organizations into the future. Drawing on her vast experience as a veteran entrepreneur, speaker, and advisor, #REALTALK founder Cherry Rose Tan provides a roadmap for cultivating the mindset, heartset, and skillset necessary for enduring success. Her impact on the mental health movement within the tech industry has been nothing short of revolutionary, helping leaders come to grips with the real stress and pressures associated with their daily work.
In the book, you'll learn how to:
- Cultivate a resilient workplace culture that embraces change and innovation, battle tested with 40,000 leaders across 27 verticals
- Master tough conversations, learning how to effectively communicate with yourself, your team, and key stakeholders to execute in difficult environments
- Empower yourself and your team with actionable strategies, combining leadership wisdom and practical tools drawn from the crucible of real-world entrepreneurship
Still Standing is not just a book; it's a tactical roadmap for businesses and their leaders, who are determined to create everyday resilience in the face of constant change. Whether you're seeking to enhance your leadership skills, navigate the challenges of business, or manage workplace burnout and wellbeing, this book offers the insights and strategies needed to thrive and innovate in these uncertain times. Join Cherry Rose Tan in exploring the three capabilities that will empower you to not just survive, but flourish in the competitive world of business and innovation.
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Seitenzahl: 383
Veröffentlichungsjahr: 2024
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Table of Contents
COVER
TABLE OF CONTENTS
TITLE PAGE
COPYRIGHT
DEDICATION
FOREWORD
INTRODUCTION
CHAPTER ONE: WHY #REALTALK?
THE DARK NIGHT OF THE SOUL
MY WHY
FOR FOUNDERS, BY FOUNDERS
THE LONE WOLF
THE GLIMPSE OF #REALTALK
THE SECOND PANDEMIC
CHAPTER TWO: BRAVE NEW WORLD
A NECESSARY CONDITION OF LEADERSHIP
THE GAME OF INNOVATION
WHAT WE CAN LEARN FROM VENTURE CAPITAL
THE URGENT NEED FOR REALNESS
THE RISE OF MICROCOMMUNITIES
A WORLD THAT WORKS FOR HUMANITY
THE CALL TO COURAGE
UNDERSTANDING THE THREE CONVERSATIONS
PART I: THE FIRST CONVERSATION
CHAPTER THREE: STABILITY
WHY STABILITY MATTERS
THE BIGGEST MISTAKE YOU CAN MAKE
CREATING STABILITY IN THE JOURNEY
#REALTALK LEADERSHIP
QUESTIONS TO CREATE STABILITY
INTERNAL EXERCISE: WHEEL OF LIFE
EXTERNAL EXERCISE: NEEDS AND NOURISHMENTS
PREPARING TO SPRINT
CHAPTER FOUR: INTEGRITY
A FRAGILE SOCIETY
THE TRAGEDY OF TONY HSIEH
THE IMPORTANCE OF LISTENING
THE BUSINESS VALUE OF LISTENING
FROM LISTENING TO SPEAKING
INTERNAL EXERCISE: LISTENING FROM EMPTY
EXTERNAL EXERCISE: SPOKEN VS. UNSPOKEN
LETTING GO OF BEING RIGHT
CHAPTER FIVE: WORKABILITY
A GAME OF RISK
HOW WE SELF-SABOTAGE
THE WORLD OF WORKABILITY
THE STANDARDS YOU HOLD
KNOWING WHEN TO LEAVE
INTERNAL EXERCISE: RADICAL PRIORITIZATION
EXTERNAL EXERCISE: TAKING RESPONSIBILITY
WHEN THINGS WORK
PART II: THE SECOND CONVERSATION
CHAPTER SIX: AWARENESS
BEING THE STRONGEST
THE WILLINGNESS TO FEEL
WHAT #REALTALK WITH YOU IS ALL ABOUT
WHY AWARENESS MATTERS
A CAUTIONARY TALE ABOUT BURNOUT
THE POWER OF LABELING
INTERNAL EXERCISE: THE COLOR PALETTE
EXTERNAL EXERCISE: HOW ARE YOU REALLY DOING?
ANSWERING THE CALL
CHAPTER SEVEN: COMPASSION
THE WORLD OF EMOTIONS
OUR RELATIONSHIP WITH SHAME
ACKNOWLEDGING MEN’S MENTAL HEALTH
THE CYCLES OF DISEMPOWERMENT
FROM DRAMATIC TO EMPOWERING
BUILDING YOUR EMOTIONAL STAMINA
INTERNAL EXERCISE: HELL YES OR NO
EXTERNAL EXERCISE: HOLDING SPACE
THE CLEARING
CHAPTER EIGHT: FORGIVENESS
THE WORLD OF RESENTMENT
THE RELATIONSHIP BETWEEN ANGER AND SADNESS
WHAT IS FORGIVENESS?
HOW RECONCILIATION UNLOCKS PERFORMANCE
INTERNAL EXERCISE: RELEASE CEREMONY
EXTERNAL EXERCISE: I FORGIVE
THE SPACE FOR COMMUNITY
PART III: THE THIRD CONVERSATION
CHAPTER NINE: IDENTITY
FROM LEADER TO AUTHOR
THE UNRAVELING
WHY IDENTITY MATTERS
HOW IDENTITY AFFECTS COMMUNICATION
WHAT IS INTERSECTIONALITY?
CREATING TRAUMA-INFORMED SPACES
INTERNAL EXERCISE: THE STORIES WE CARRY
EXTERNAL EXERCISE: WHAT THEY SAY
MOVING TOWARD THE GREATER GOOD
CHAPTER TEN: RECLAMATION
THE COLLECTIVE ILLUSION
FROM ANGER TO RECLAMATION
HOW I DISCOVERED RECLAMATION
THE MISSING PIECE
HOW RECLAMATION TRANSFORMS US
INTERNAL EXERCISE: THE OTHERED SELF
EXTERNAL EXERCISE: YOUR PEOPLE
HOLDING THE LINE
CHAPTER ELEVEN: SOVEREIGNTY
THE AGE OF MISTRUST
THE UNWORKABLE WORKPLACE
SOVEREIGNTY IN PRACTICE
RESILIENT, SMART DESIGN
YOUR CIRCLE OF TEACHERS
A FRANK CONVERSATION ON ACCESS AND POWER
INTERNAL EXERCISE: NORTH STAR
EXTERNAL EXERCISE: CALLING FORWARD
MOVING FORWARD, TOGETHER
CHAPTER TWELVE: BEING THE BRIDGE
A WORLD WITH #REALTALK
A CULTURE OF COLLECTIVE OWNERSHIP
THE IMPACT THAT LIVES
CHAPTER SUMMARIES
WHAT’S NEXT?
ACKNOWLEDGMENTS
ABOUT THE AUTHOR
REFERENCES
CHAPTER 1
CHAPTER 2
CHAPTER 3
CHAPTER 4
CHAPTER 5
PART II
CHAPTER 6
CHAPTER 7
CHAPTER 8
CHAPTER 9
CHAPTER 10
CHAPTER 11
CHAPTER 12
INDEX
END USER LICENSE AGREEMENT
Guide
Cover
Table of Contents
Title Page
Copyright
Dedication
Foreword
Introduction
Begin Reading
Acknowledgments
About the Author
References
Index
End User License Agreement
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ADDITIONAL PRAISE FOR STILL STANDING
The performance of every business leader hinges on their ability to respond quickly and clearly. Still Standing gives leaders the ability to adapt by using their most underutilized asset: tough conversations.
—Dan Martell,Wall Street Journal best-selling author of Buy Back Your Time
A clear, clarion call for high performers to focus on the resilient, powerful skills that matter. It’s time to open the door to connection, care, and humanity.
—Seth Godin,New York Times best-selling author of Linchpin and The Dip
Still Standing was written with entrepreneurs and leaders in mind. A practical resource, this book gives leaders the tools to thrive and to lean into the tough conversations that unlock our greatness.
—Giovanni Marsico,three-time Emmy-winning producer and Founder and CEO at Archangel
Still Standing is needed at a time when business leaders, especially founders, are navigating tough times. Being a founder is a rollercoaster ride, and in the most difficult times, there are few resources available. This book is genuine, uplifting, but most of all, empowering to those who need more real talk in their lives.
—Bedy Yang, Managing Partner at 500 Global
This book is an important contribution to our innovation ecosystem. Cherry Rose gives business leaders the actionable frameworks to build their resilience, so they can thrive in the workplace for years to come.
—Brice Scheschuk,Managing Partner at Globalive Capital and Co-Founder and CFO at WIND Mobile
Having spent over 20 years as an entrepreneur, operator, and now VC, I can attest to the critical importance of workplace mental health, and yet how often this is overlooked or brushed aside. Still Standing is an honest and compassionate look at the conversations founders and leaders need to have today to ensure long-term health and vitality.
—Janet Bannister,Founder and Managing Partner at Staircase Ventures
Managing trauma and its impact on decision-making is increasingly the issue of our time. We have more tools available than ever before, yet the need has never been greater. Still Standing is a thoughtful dive into leadership mental health… a must read for all aspiring entrepreneurs.
—Bruce Croxon, Managing Partner at Round13 Capital and Co-Founder and CEO at Lavalife
STILL STANDING
WHAT IT TAKES TO THRIVE AND INNOVATE IN A MESSY WORLD
CHERRY ROSE TAN
Copyright © 2025 by Cherry Rose Tan. All rights reserved.
Published by John Wiley & Sons, Inc., Hoboken, New Jersey.Published simultaneously in Canada.
No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning, or otherwise, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, or authorization through payment of the appropriate per-copy fee to the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, (978) 750-8400, fax (978) 750-4470, or on the web at www.copyright.com. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, (201) 748-6011, fax (201) 748-6008, or online at http://www.wiley.com/go/permission.
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Library of Congress Cataloging-in-Publication Data is Available:
ISBN 9781394279029 (Cloth)ISBN 9781394279043 (ePDF)ISBN 9781394279036 (ePUB)
Cover Design: Wiley|Concept: Bill Falloon
To my dearest Keane,the greatest entrepreneurof all time
FOREWORD
As a venture capitalist, co-founder of multiple companies, and a startup community builder, I have experienced the unique challenges a founder faces on their journey. Tech founders have a unique job: to be the leaders creating and building the companies of the future. Over the past three decades, I have worked with and invested in numerous early-stage companies, and I believe deeply that founders need a startup community that supports them.
In early 2023, Cherry Rose reached out to me and asked if I would walk alongside her and contribute a foreword to her book, which is resolute and earnest in its stand on workplace mental health. More importantly, it is her deep belief that the lessons of this book will not only support and lift founders, but leaders of all organizations who are now faced with navigating the treacherous waters of innovation.
I currently host a podcast called Give First with my close friend and Techstars co-founder David Cohen, where, among other things, we discuss the importance of being positive and influential members of the innovation ecosystem. During the pandemic, I worked with the team at Techstars to produce the short documentary Entrepreneurship & Mental Health, which included a segment on my struggles with anxiety and depression. We do this because we know that founders and leaders struggle with mental health, often in silence, due to the stigma associated with mental health in the workplace.
Cherry Rose’s book matters. Our industry is one of trailblazers: making bold moves and trying to change the status quo. During this journey, many founders face the most difficult challenges in their lives.
Working with tens of thousands of founders, Cherry Rose found that the answer reveals itself. We can become better, even thriving leaders, by mastering the art and science of tough conversations. Real talk is the key to creating an innovation economy where founders and leaders ask for help when needed. Real talk is the key to destigmatizing mental health and recognizing that most leaders will go through at least one adverse mental health experience during their careers. Real talk is the key to building adaptive and resilient leaders who set the example and strengthen our innovation economy.
In this book, you will find that you are not alone and will discover a way forward. This conversation on real talk and tough conversations may make the difference between a founder or leader who rises to the occasion and one who crashes and burns. Cherry Rose provides a step-by-step system that business leaders can apply and scale so that they and their organizations can thrive and succeed.
I hope the words and stories on these pages move and inspire you. Cherry Rose’s book cuts through the noise because of her authenticity and bravery. She’s had her own lived experience but has also been in the trenches with the thousands of tech leaders who have struggled with mental health, enabling her to convey the tools and the lessons that empower every leader to thrive and innovate in a messy world.
Whether you are a first-time founder or a veteran leader, Still Standing is a must-read. This book will challenge you to be honest with yourself, embrace your humanity, and lead with empathy and strength.
—Brad Feld, Partner at Foundry and Co-Founder at Techstars
INTRODUCTION
A few years ago, I sat with the CEO of a very successful, publicly listed company. This individual was wise beyond their years, weathered over the decades spent as a CEO. I will never forget the words they said, “If there is anything you need to do, anything you need to say, Cherry Rose, it is to tell entrepreneurs that trauma is inevitable. Loss is inevitable. Pain is inevitable. I wish I knew that going in so that I could have been kinder to myself.”
After experiencing my own trauma, loss, and pain, I was inspired to create #REALTALK, the mental health movement for the tech industry. I have dedicated the last five years of my life to this work. I traveled around the world, holding space for over 40,000 leaders as we cried, laughed, and connected over our victories and our demons. Then I met some incredible founders, who are now dear friends and who encouraged me to tell my story and share my message with all of you.
Writing this book has been the most difficult, yet most rewarding experience of my life. It has been triggering and confronting, as I process my trauma and live by example. I have spent the last several years cleaning up my life to bring you the book that lies in your hands.
This book is not therapy. This book is not treatment.
But what this book can be is the first step – a shared space and understanding of the ups and downs of entrepreneurship and innovation. It can be an admission, an acceptance that it is okay to struggle and that you aren’t alone. You are not any less of a human, of a business leader, just because you struggle.
In this book, I invite you to keep an open mind. Allow your walls to come down and know that you are in a safe space. At #REALTALK, we are experts at what we do. We are founders first, with a deep desire to help our own. We know you because we have raised money, scaled companies, and dealt with the chaos of bankruptcies, lawsuits, defamations, and the good old drama of personal and professional stress.
As leaders of the future, our ability to create and transform industries is dependent on our stand – on our ability to say yes, to go all in, and to declare a possibility that others deem crazy. It is my stand that this book ends up in the hands of every business leader who is determined to survive and even thrive in these challenging times. I wish for real talk, the decency to be honest and there for one another, to live in the hearts and minds of every business leader who is committed to this path. To know that when you are struggling, when you find yourself at rock bottom, I, our champions, and our community will be there.
We have been where you are and we can help.
We will take a journey curated for you, inspiring you to build and lead in these changing times. This book is your safe haven, your eye in the storm.
Let’s begin.
CHAPTER ONEWHY #REALTALK?
It was 26 December 2017, and it was the worst day of my life. Something was wrong. I could feel it in my bones. I woke up that day with a sense of dread. Inexplicable, stomach-turning dread.
For the last 48 hours, I had been trying to reach my little brother, Keane. Keane was my only sibling, and I missed him. We owned a Canadian blockchain company, a first mover in the space, that provided infrastructure and liquidity to global financial markets. I was involved as an early investor and Keane was its co-founder and chief operating officer.
Even though there was a fierce determination to make this company work, entrepreneurship was hard. Really hard. Keane was working long hours, the 100-hour weeks familiar to tech founders. It was workaholism – a common and even expected condition in the tech industry. A few weeks prior, Keane said he would be harder to reach. The year was ending and there was a frenzy to complete as much as possible before we saw each other for the holidays.
Despite our busy lives as sibling entrepreneurs, Keane and I had an unsaid agreement. Even though we were constantly busy and stressed, we always made time for each other when the other asked. Always. It was nonnegotiable. We made time for the things that mattered, like birthdays and tough times.
That day felt bizarre. Multiple people, from our mum to his best friend, were sending texts and calls to Keane. I left so many messages that day: texts, Facebook messages, WhatsApp messages, and phone calls. No one heard back and everyone was worried.
Keane was nowhere to be found. Everyone was wondering, Was Keane okay? Where was he? Had something happened to him? I had this weird, unsettling feeling that was building in my stomach.
Something was wrong. We needed to do something now.
I ended up calling his building and talking to a security guard. They knocked on his door to see if he was home. No answer. They guessed that Keane was outside, shopping on Boxing Day like many others in the city.
At that moment, I had a visceral reaction in my body, a whisper that said, “No, he’s in there. I don’t know how or why I know this, but he’s in there.” I asked them to open his door and they refused. I wasn’t listed as his emergency contact. What was I going to do?
With one choice left, I called the police.
No one could have prepared me for what I saw. I remember rushing my way downtown with my parents and seeing paramedics and police surround his building. Watching the red and blue lights, the night felt so loud yet so silent at the same time. I ran to the elevators ahead of my parents, who were parking the car. I was trying to see what was happening.
As the elevator doors opened, I ended up on Keane’s floor. Running toward his condo, I was stopped immediately. In the hallway stood a police officer with a solemn look on his face. The officer told me he was so sorry.
“Your brother is gone,” he said.
Keane was gone. He had passed away in his sleep on Christmas.
THE DARK NIGHT OF THE SOUL
I share this experience of loss with you because, for many years, I grappled with my dark night of the soul and the aftermath that ensued across my family, our friends, and the tech industry.
Keane passed away from massive and sudden organ failure, a combination of prolonged overwork (120 hours a week, in fact) and a misdiagnosed condition. What do you do with that?
At the time of writing this book, the planet has been ravaged by the COVID-19 pandemic, followed by the economic recession. For the first time in decades, our planet is collectively grieving as millions of loved ones have passed away: sons and daughters, fathers and mothers, and even friends. So rarely, when we need the support the most, do we allow ourselves to be seen. So rarely, when we are struggling in the darkness, do we allow ourselves to be heard.
When was the last time you were able to be real with someone?
In this book, in this journey we share together, you are safe. You are seen. I wrote this book for people like you and people like me, who are navigating this messy world. I wrote this book for the business leaders of the future, the bold and the ambitious, who are innovating and building the new world we live in. Leaders, founders, and entrepreneurs who seem indestructible on the outside, but are just as human as everyone else.
This book is your eye in the storm, a space to return and rest when you need it.
In the media today, the game of innovation is glamorized. We celebrate the founders, the money they have raised, and the companies they have sold, but rarely do we see the journey it took to get them there. The sweat, the tears, the times when we doubted ourselves. The things we lost as we chose work and the pursuit of success over relationships, safety, and even our own health.
Innovation is an all-in sport. It is intense, emotional, and confronting for even the strongest of leaders.
As a serial entrepreneur, I am often hired by clients around the world as an innovation and mental health speaker: to share my real and hard-won experiences in navigating the game of innovation. This game includes exponential technologies like artificial intelligence (AI), blockchain, and metaverse, where all corporations, associations, and even universities are feeling the pressure to catch up. It is in these high-pressure, high-stakes environments that our workplaces are suffering.
Regular folks are struggling to make ends meet, and there is a general level of discontent (or as my clients like to call it, “rage”) that has resulted from years of prolonged suffering on multiple levels: physical, mental, emotional, financial, and political. Regular folks are trying to find their way in this weird and wacky world, while being faced with the real and looming threat that their jobs and their livelihood can disappear at any second due to layoffs, offshoring, or even AI. In such a pressure cooker where so many of us feel the need to be excellent and to stand out to survive, the ability to share our true selves with others has lessened over time.
In working with many of my students as a university professor, I see them struggle to pause or even admit to needing help for fear of losing out on an opportunity or showing weakness. These pressures are at the individual level and also occur in teams and finally organizations, who are facing the largest wave of uncertainty they have seen yet: the extinction of 300 million jobs this decade due to AI.
How do you operate in a world of never-ending stress and change? How can we still stand as leaders, despite struggle after struggle?
MY WHY
Back in 2019, I ended up at a private event hosted by Jayson Gaignard, who founded the company MastermindTalks. His community of entrepreneurs is one of the most exclusive masterminds in the world, attracting 8- to 10-figure entrepreneurs and thought leaders from various industries.
At a restaurant in downtown Toronto, I met Tucker Max, a four-time New York Times best-selling author. As we chatted privately, our conversation became emotional. I had been following Tucker’s work because he was public about his own struggles as an entrepreneur and how deep-seated trauma (and his subsequent healing journey) had affected his life. Being with Tucker, I remember leaning in and sharing my story. My story of what I had lived through and lost.
It took the 20 years of trauma that I had experienced and the 15 years of healing I had done prior, in order to have that conversation with him.
I told him that I was running #REALTALK, the mental health movement for the tech industry – my most important work yet – a platform for entrepreneurial stories, resources, and support through executive training, peer circles, and podcast interviews. Like the name of this movement, our superpower was talking: I was spending my days, fresh from my brother’s death, sitting with tech CEOs and realizing that I wasn’t alone in my lived experience. I was having mental health conversations with friends and colleagues in tech and it surprised me. There were so many of us who had struggled with mental health.
In those rooms, behind closed doors, these conversations opened a floodgate in my heart. These conversations felt tender and precious; despite the successes of these business leaders, they had struggled with depression, grief, addiction, and more.
In being with Tucker that night, he told me in no uncertain terms that I needed to write this story. That there are leaders we have lost in our families or in our circles due to mental illness and suicide. That this book could be the difference to the business leaders standing on the edge.
I know you, fellow leader, because I was one of those people.
When I lost my brother, my only sibling, I was confronted by my existence and the experiences I had lived. Before #REALTALK, I would walk into every room, thinking that I was alone. Despite being respected in my personal and professional circles, I felt like no one understood me. I had the accolades and the degrees, but no one knew the intensity of my despair.
I was a Filipino-Chinese Canadian and a first-generation immigrant. I was a Woman of Color (often the only one in the room), surrounded by other C-Suite leaders. As much as our industry pushes to be progressive, we have a long way to go. For instance, 7 to 10% of all venture capitalists are women, yet 52% of them are White men. This stat matters because career opportunities and upward mobility are dependent on who makes the decisions and who holds financial power. When we look at tech founders who are venture-backed, less than 1% are Women of Color, with 0.32% being Latinx founders and 0.0006% being Black founders.1
I share this context because the impact of mental health and trauma can feel absolute. Mental health impacts every part of our personal and professional lives, and it has a disproportionate impact on those who are already underrepresented.
When I began in the tech industry, in the game of innovation, I came as a trauma survivor. I was young, but I had already lived through so much, being surrounded by years of abuse, trauma, and mental illness. I had a family history that was rich with entrepreneurship yet steeped in painful experiences around colonization, war, and poverty from the Philippines.
By the time I came into this world, the odds were already stacked against me.
Even though I have suffered great losses, I understand that I am lucky. I could have ended up a statistic like my late brother, but I survived. Thrived even. In my grief, I was able to create a platform like #REALTALK and turn something horrific into something beautiful in this world.
I know Keane would be proud.
Through the unexpected ups and downs of life, we can choose to do better. We can say: It is time to support our own. It is time to see this book in the hands of every business leader and for them to know they are not alone.
FOR FOUNDERS, BY FOUNDERS
In the early days of our movement, there was pushback. Lots of pushback.
Our branding was particular, aimed at tech founders and only tech founders. People would approach me at events and say, “Why is #REALTALK for the tech industry? Why isn’t #REALTALK for everyone?” As a trauma survivor myself, I know many industries and many communities struggle with mental health.
People found our obsession with tech founders very peculiar.
Many people assumed that #REALTALK was influenced by Keane’s death, but the stakes are much more than that.
It is my deepest belief, being one of you and building the companies of the future, that business leaders of all walks of life can change the world. It sounds cheesy, but it’s true. Despite what I have lived, I am lucky that I discovered entrepreneurship and innovation at such a young age.
When I was a little girl, I didn’t know better. I didn’t know that I was an anomaly or that my upbringing was unique, sitting at the dining table with Keane and our parents as they asked us what business idea we wanted to build next.
In every great loss I have ever experienced, I have created a company or a community to solve that problem.
In seeing how the tech industry has evolved in just a decade, we are the future. Technology is the future, not just for the founders, but for every industry on the planet. The business leaders of the future, individuals like yourself, are some of the biggest dreamers I know, declaring their moonshots and building their literal or figurative rockets to the moon. Each of us has so much potential, so much to give to the world, but we forget that.
We forget our roots and our why. Most importantly, we forget our hearts.
Our decisions and the way we lead can harm or inspire the people around us. In climbing the very steep hill that is building #REALTALK, I am certain that we can do better. That we must and can support our own, especially when leaders are stumbling in the darkness that is mental health. I know that being a leader in these times is tough, but we don’t have to do it alone.
We can be friends. We can be allies. We can speak out and reconnect leader to leader. That was the vision of my late brother, who built and left his legacy in his own way.
Back in 2014, Keane was fresh out of university and working at one of the best mobile development firms in North America. When summer came, he flew with his close friend to Cape Town.
That trip was a big deal for him. Growing up as first-generation immigrants, we were poor. It was only when we were adults, making money from our jobs and our businesses, that we could afford to travel outside of North America.
He desired to see the world.
When he arrived in Cape Town, he noticed something: his entire itinerary was full of tourist traps, rather than authentic experiences to meet and understand the people who lived there. At the last minute, he changed his itinerary and booked a local guide, who arranged for him to stay in the villages. These villages were far away from the glamorous hotels. These were the villages where many of the locals stayed.
In the village that hosted him, Keane’s life would be forever changed. In the weeks he stayed there, what moved Keane were the South African people who were entrepreneurs. Business leaders just like you and me, who have a dream. Who utilize their gifts to create something from nothing.
As Keane often reminded me for years to come, they were the original entrepreneurs. The original founders.
He admired them for their tenacity and resourcefulness, the way they used their hands and their lands to build goods. As he got to know them, there was one person who stood out: a grandmother. She had lived in this village her whole life and her presence was formidable. For decades, she would weave baskets by hand and then travel many miles by foot, selling these baskets to neighboring villages. Afterward, she would save every piece of money from those sales, allowing her to purchase her first house years later.
This is my brother Keane from this trip. He reminds me why #REALTALK standsfor founders, by founders.
In her example, she embodied a glimpse: an opening, an image showing what was possible for every other person in her village. It was her heart and her devotion to a better life that inspired Keane to become a founder.
In the same way that she was a glimpse for her village, Keane wanted to be a glimpse for her and all of the other entrepreneurs who dreamt of a better life. She reminded him so much of our ancestors, who experienced colonization, war, and poverty. Humble roots across generations, my ancestors planted the entrepreneurial seeds for our lineage and cultivated these seeds into successful businesses.
Keane saw this woman’s potential.
It was his belief, our belief, that entrepreneurs like her deserved equal access to opportunities – that it didn’t have to be so hard. In Canada, we are fortunate that services like banks are just a walk away. In that village and many regions like it, there are no physical banks for miles around. Banks didn’t build in those places because they didn’t see those individuals as “profitable” customers.
Was there a way to empower her, leader to leader?
It is this glimpse, a world for founders, by founders, that birthed our journey into blockchain.
THE LONE WOLF
We are more connected and disconnected than ever. I know this sentence to be true because of the 40,000 leaders we have worked with at #REALTALK.
In many ways, my experiences have led me here. A potent combination of a trauma survivor, psychology expert, and tech founder has led me to you. #REALTALK started organically from the need to be connected, knowing that as business leaders we could and will support our own.
In technology, we are heading there. Coming from the world of blockchain, Trust (with a capital T) is significant. Blockchain is a record-keeping technology that was built to restore and secure Trust, restoring functionality and progress in people and institutions where power and money reside. Blockchain and crypto have made their mark on the world because inherent in their nature is the ability for stakeholders to engage with each other, even in initial conditions where there is low or no trust amongst individuals. When you make a transaction, blockchain is what serves as the discerning and vetting intermediary, protecting both sides from harm. It is this trust that allows people to transfer and invest their money at whatever level they wish to participate. It is this trust that is the bedrock of our financial systems for the twenty-first century.
I share this observation because, unlike blockchain, our interactions with humans lack this foundation. We lack trust in one another, and thus, we are lonely.
We operate like lone wolves.
We live in a world where instead of connecting with others, we pretend. Our social media feeds are examples of how hard we try to hide and show people that our world is perfect. It is this foundation that has led to other trends like cancel culture and fake news.
Despite our technological advances, we are the loneliest we have ever been.
In a 2020 study, health insurer Cigna found a 13% rise in loneliness since 2018. Surveying 10,000 adult workers, they found that 63% of men are lonely and 58% of women are lonely.2 This trend is increasing with every generation too: Gen Z (18–22 years old) reporting the highest loneliness average, with Boomers having the lowest.
Not only are we facing a dramatic increase in loneliness from a generational perspective, but it is occurring in our entrepreneurs as well. For instance, Startup Snapshot conducted a 2023 study focused on North American tech founders and found that founders spend 60% less time with spouses, 58% less time with kids, and 73% less time with friends and family.3 Despite the hype around startups and the latest technologies like metaverse and AI, entrepreneurs are facing an average level of loneliness at 7.6/10.
The path to success can and has been incredibly painful for many. In a world of pretend, we have eroded trust completely. With the erosion of trust is the erosion of our dignity, connection, and support of other human beings, and a standard in the workplace where every person is left to fend for themselves, lucky if they survive. What is even more troubling about this growing pattern is that when I speak to audiences around the world, all companies from now until the foreseeable future are tech companies.
No company will be able to survive in the long run without being able to innovate. No company will be able to ignore the effects of technologies like blockchain, artificial intelligence, augmented reality (AR), and more. Instead of allowing our people to drown in the workplace, unable to keep up with modern-day pressures and technologies, we need to come together. We need to create a shared language to acknowledge the difficult realities of the workplace, so that ourselves and others can feel safe to drop the mask. To stop pretending and operating as lone wolves.
What is a world without trust? What is a world without real talk?
THE GLIMPSE OF #REALTALK
When I talk to strangers, the most common question I get asked is, “How did #REALTALK start?”
In my world of startups and venture capital, we are inundated with the mythical figure of the founder, akin to an entrepreneurial superhero. Instead, my dive into #REALTALK was humbling, messy, and profoundly human.
Right after Keane’s death, I was in huge amounts of pain. Not just physical pain or emotional pain, but spiritual pain. I was questioning everything about the fundamentals of life, principles that I once saw as resolute. I was questioning my purpose, my family, and my career. I had stayed awake for three entire days, my body in shock and heartbreak.
I couldn’t sleep. I went from being an older sister, building companies with Keane for 10 years, to being an only child.
It destroyed me.
What was worse was the onslaught of struggles, of uphill battles, that came.
I was organizing my brother’s funeral of 400 people and writing the eulogy. I was creating his Celebration of Life video and pouring through thousands of his pictures and videos; it was heartbreaking. My mother, who was grieving, was diagnosed with Stage 3C cancer less than two weeks after Keane’s death.
She got the news four days before the funeral.
The company that Keane and I shared felt the loss too. His best friend was its co-founder and CEO, and the leadership team was like family to Keane. In the aftermath of losing their co-founder and COO, there was so much personal and professional stress for the team. Like any other startup, there were relationships to manage from employees to investors. There was years’ worth of hard work on the line and they needed to keep going.
It was at this moment, when everything in my life was burning, that I saw a glimpse. Akin to my brother’s glimpse in South Africa, I saw something different for the first time.
Before this moment, I had moved through life using intelligence and willpower. I worked very, very hard to escape my demons. I came from an abusive and dysfunctional environment, the byproduct of a family member whose trauma and hurt went unprocessed. However, there was a key difference between my experience and theirs: I had the privilege (and eventually opportunity) to access mental health support, while they did not
I felt so alone at that moment, grieving Keane’s death. Who else could understand what I had survived and what I was going through?
In that moment of rock bottom, of finding a way to survive, my glimpse whispered, “This can’t be true. You’re not alone. Surely, there must be others like you.”
Four weeks after the funeral, I delved into this glimpse. Tactical and lean like a founder, I emailed 50 tech founders and asked if I could sit down with them one-on-one. I wanted to know:
What was it
really
like for them, being a founder?
Was I the only one who lived through this kind of pain? Was I alone in my experience?
When they look back at their business failures, what was the number one reason why they failed?
I was a ball of nerves. Tender and exposed, I had never asked my peers these questions before. Before this moment, our conversations were safe and even predictable: fundraising, legal, and operations. This, right here, was a different ball game.
It was real talk.
The conversations I had over the next several months blew me away.
The more I sat with the founders, the more I heard something. Something small, subtle, and repeating, especially around their business failures:
“I knew my co-founder wasn’t the right person to scale this company. I should have asked them to leave. I waited until the last possible moment to talk to them.”
“We were running out of cash flow and I didn’t want to admit it. I waited until our company went nearly bankrupt to ask for help from my investors.”
“I was burnt out. I was so good at what I did, but I hated my life. I was so embarrassed to admit that I didn’t want to be the CEO of my company anymore.”
In the glimpse, the pattern I saw was avoidance. Thirty-five of the 50 founders (70%) cited avoidance as the number one reason for their business failures. People were holding on to their secrets and masks and they were hurting themselves, their families, and their companies. Highly successful people, hiding in plain sight, not allowing themselves or anyone else to see what was real.
And what was more remarkable?
We had so many of these founder stories intertwined with mental health and trauma that there were more survivors (people with direct experience) than allies. Despite their large and affluent networks, they had been hiding for long periods of time. I had people in hiding for six years, all the way to three decades.
That’s a long time, pretending to be someone you’re not.
THE SECOND PANDEMIC
This book has gone through hell and back. I meant to release this book in the fall of 2023, and six weeks before the finished books arrived at my house my former publisher became insolvent. It was shocking and sudden and it hurt.
It hurt to be so close to the finish line and to feel the opportunity, the opportunity to impact thousands or even millions of people, to be taken away from us. That after 2.5 years of tolling away to bring this book to you, I had another marathon ahead of me.
I share this part of my story because I am grateful to my publisher, Wiley, for taking the leap with me. We spent eight months talking behind closed doors to see whether or not this book, a book that is essentially about the importance of tough conversations, was a good partnership for both of us. In discussing with my Executive Editor Bill Falloon (thank you, Bill!), we came to the mutual conclusion that this book was and is needed more than ever on the planet.
The fact is, every organization and every workplace in the world is going through what I call a second pandemic – not a physical one, but a mental health one. Every entrepreneur, leader, and organization out there is faced with the threat of their survival as a business, in the face of the most massive and systemic problems of our lifetime, from climate change to artificial intelligence.
For far too long, leaders have risen to this challenge by doing more. Working harder. And asking their direct reports, their employees, to do the same. But people are tired and are fed up. Every day, I check Reddit for the latest news to get a pulse of how people are thinking and really feeling – and it’s not good. New subreddits like r/antiwork and r/canadahousing convey a sentiment where the American dream is broken and even nonexistent: no longer can the security and success we dream of be achieved through hard work. Working as hard as you can, for as long as you can, is no longer an acceptable solution for my generation and the generations to come.
