CHAPTER ONE
WHY #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...