Full Moon Over Honolulu

Connecting at a Human Level at Honolulu Tech Week

Walking to my Uber pickup at the Honolulu airport, I was greeted by the warm, humid wind. My flight from Seattle had taken me south by 26 degrees of latitude. My driver was a father. We talked about our children as we passed the orderly industrial outskirts of the City. He gave me a tip on where to find a good local fish lunch in Waikiki, then dropped me off at the wrong hotel. I had my first opportunity to wander Honolulu’s streets, the mile from the wrong hotel to the right one, and “orient” myself, as my father used to say when telling tales of exotic travels. I hung on to every word when my father spoke as we got to know each other as adults over lunches at Chinese and Vietnamese restaurants in Toronto. We were really talking about what he had been doing instead of being a father.

I’ve always felt soothed by the busyness of cities. I grew up in a city. As a young boy, I was free to roam the streets and parks. I walked for hours and miles through the streets of 70’s and 80’s Toronto. I always knew where I was. I disappeared into the crowds - an invisible child. I mumbled and muttered, ducked into laneways, cursed, sang, and danced along the sidewalk, free in my anonymity to express the feelings I guarded from the adults in my life. 

As an adult, traveling to cities was a way of seeing potential futures. Different realities I may choose to manifest. There have been corners, angles of light, views, and sounds I’ve noticed as a visitor that pulled me to change my life and spend years living in a new city – in the reflections. In Miami Beach, it was the sound of the ocean off South Beach and the angle of sunlight on Art Deco architecture. In Brooklyn, it was Grand Army Plaza looking down Prospect Park West and the mix of professionals and families walking outside the Brooklyn Library. And in Seattle, I watched and listened to teenagers jumping into Lake Washington from a dock in Kirkland on a hot July evening. I was visiting Redmond for a conference at Microsoft and at the end of the day took a taxi. “Just drop me off by the Lake,” I told the driver. Take me to the water. Five years later, on summer evenings after dinner, I’d walk with my daughter and son down to the same lake to swim in the light of the sunset.

This was my third time in Honolulu, but my first time visiting alone. I was there to speak at Honolulu’s inaugural Tech Week conference.  The topic was the mental and emotional health challenges and opportunities for founders, a subject I knew to my core. I was excited to meet a room full of founders and offer an invitation for them to see and feel themselves as whole people, more than entrepreneur personalities. To connect their bodies and spirits to the work of bringing new ideas into the world in the form of businesses. It was a long way to travel to share my experience with a room full of founders, and I didn’t know if it would matter.

I enjoy public speaking, but this conference was different. My intention for this talk was not to educate or convince with reason but to connect from the heart. It was an experiment, and I was trying on a new identity.

Honolulu is my kind of food city. A mashup of Asian, Polynesian, American, and European culinary traditions, fresh fish, lots of rice, and lots of street food. In 1996, after college and a year of working in the post-production department at a cartoon studio, I traveled once around the world, East to West,  and spent three months in Southeast Asia before flying to Turkey. A month in Vietnam, a month in Laos, and a month between Thailand and Malaysia, eating whatever the street stalls had to offer. I ate water buffalo, durian, and dog, selected a cobra for snake soup, and negotiated the price of grilled shrimp by the each. I was lonely and depressed for a full week after landing in Istanbul, stunned by the relative silence of Europe and longing for the chaos and spice of Kuala Lumpur. In Honolulu, I felt comfortable and welcomed by the rice.

I had three items on my agenda: a welcome reception headlined by the Mayor and Guy Kawasaki, a small dinner hosted by my gracious host Joey Aquino who had invited me to speak, and the session in which Joey was set to interview me, the multi-time founder who’s had the full range of experiences from building companies, exits, heart surgery, depression, healing, and building more companies. It was the first conference I could remember where I wasn’t there to sell anything. I was there to offer my presence and perspective. It was a leap of faith. What if my experience didn’t matter? What if the audience didn’t want to hear about my story? What if they just wanted us to give them instructions? What if I had fooled myself and I was really there for my ego to tell the story of how much I had overcome? How would I know?

My approach to work and life has transformed. After bottoming out after a complicated recovery from heart surgery, I learned I wasn’t ready to die. There was much I needed to change to be free and ready to move on when the time came for me to leave my body behind. Recovery and depression showed me it’s possible to die while living. My mind trapped my body in grief and sorrow as I worked my way through the trauma of surgery and down into the traumas that lay beneath; the feelings I had worked so hard to keep hidden. Awakening from depression showed me trauma could be cleared, though it felt like death at the time. Unshackled from repressed emotions, my mind and nervous system were freed to live in the present. I flew very close to the sun to melt away layers of ignorance, and I wondered how much of this experience I could or should convey and what would be heard by people I was meeting for the first time.

On the ride from my hotel to the conference venue, the Uber driver and I did not speak. I wondered about his life. He seemed far away. I walked into the event venue and felt the familiar discomfort of the outsider. A new city, new people, “What do you do?” What story should I tell? Why was I there? I didn’t have a routine or pre-packaged presentation to share. Networking events and conferences had become less devastating over the years, but the core discomfort never fully receded. I loathed networking events when I was younger because they reminded me of the schoolyard. There were questions I didn’t want to answer. “Where’s your father? Why do your clothes smell? Why are you so weird?” I took refuge in solitude. Walking through the city.

“What do you do?” I had always felt the judgment - lack of pedigree, education, credentials, and experience - did I deserve to be in this room? Conference people always seem so comfortable, smart, and accomplished.

Regardless of my age, it’s easy to spiral subconsciously back to childhood. The outsider, new school, new park, and community center, new threats - see those first - and sometimes new friends. But always at a distance. As I grew from childhood to adolescence and then into college, I created a perception of safety by being tougher, more athletic, smarter, and crazier than others. I separated myself, making myself better or worse. I built the identity of the entrepreneur to prove to others and myself that I was worth something. Starting companies didn’t feel risky. 

Ignorance of risk served me well. I never felt there was safety to fall back on and felt strangled and claustrophobic in every “job” I’d ever had. Putting others in charge of my safety was terrifying. I built companies because I believed I could only rely on myself.

Promoting my companies and myself had always felt necessary. But I wasn’t in Honolulu to pitch investors, recruit for new roles, shmooze with politicians, or interview with the press. I was just there to be me. Someone I was getting to know. A slightly older, wiser, more comfortable, experienced founder who’s recovered from major heart surgery and learned the heartbreak of how I had created my own isolation and difficulty.

How could I sum up my work when asked, “What do you do?” I spoke to the host and a few people in the crowd. I listened and shared why I was there. “I’m here to talk to founders about our mental and emotional health.” I shared stories, and I listened. I noticed how my nervous system responded to body language and voices as I moved in the concentric circles of the networking event. What was I attracted to? When did I recoil? What’s the nature of this network?

I left the reception early, before the Mayor arrived, to attend a small dinner gathering. My host Joey had invited me and a small group of founders, most of them Y-Combinator alum, to a restaurant in the Kaimuki neighborhood. Another Uber ride. The driver felt like an old friend. Perhaps a guru from a previous life.

“What’s going on in there?” the driver asked. His car was a mess like he had been driving for days.

“It’s the Honolulu Tech week opening reception,” I replied. “The mayor is speaking now. Mostly tech founders and politicians.”

“Tech week, huh? What do you do?”

“I used to run a company that made modular housing. Now, I’m an advisor.”

“Real estate?” He asked. “You do that with your money?”

“Some.”

“People in there have money?”

“Yeah, there’s some people with money in there, but most are just getting started.”

“Looks like a money place. Big housing problem here. Not enough money. No problem for rich people though.”

He dropped me off in a parking lot next to the restaurant. I stepped out, though I wanted to keep talking. He watched and waited, making sure I arrived.

Walking into the restaurant, I felt my identity questions return. There’s a code that founders use to develop a comparative position. How cool is your idea? How famous are your investors? How likely is an exit? We often pitch each other because we’re so used to pitching. I had my story, but it no longer felt real. I wondered how it would feel to stay present through the evening. No pitch.

It was lovely. Joey was a gracious host, the staff were patient and accommodating to my heart-healthy dietary needs, and the guests were thoughtful and caring people. The anticipated discomfort must have been my confusion this whole time. I wondered how others felt. It was lovely to be a different version of me. Less needy. Listening and hearing. We talked, switched positions, and met each other. I had an extended conversation with David, who was from Honolulu and had worked with Joey at Amazon in Seattle. David invited me to join him the day after my conference event for a morning swim in Waikiki.

After dinner, I walked three miles from the restaurant back to my hotel in Waikiki. The first mile was through a residential neighborhood. I walked along the sidewalk through people’s lives as couples returned from their chores and events, mothers and daughters watched TV, and men sat alone in open garages surrounded by tools and unfinished projects under bright fluorescent lights, gazing into dreams I couldn’t see. As Kaiumuki descended into Waikiki, I looked through an open door under a bright light into a small restaurant with seven or eight tables. This was the kind of place that subconsciously pulls me in. I made a note and looked up the name “Sunrise Restaurant.” It was an Okinawan restaurant, and I had never had Okinawan food. I felt an attraction, like they were waiting for me inside the restaurant. Back at the hotel, I looked up the Sunrise Restaurant to see if they had anything I could eat and then fell into a deep sleep.

The next day, after my Zoom meetings at the hotel, I returned to the Entrepreneur’s Sandbox for my talk with Joey. We sat on stage, both of us on stools, in front of an audience of eighty-five. The audience was as curious as we were. Joey talked about his struggles towards the end of his time as an executive at Amazon, then asked me questions about my journey: childhood, moving to the US, building businesses, selling some of them, moving from Miami Beach to New York City to Seattle, working at Amazon, building Blokable, and burying Blokable. And having heart surgery. Throughout the conversation, I focused on staying present. I didn’t want to get into my head with the stories and what I thought I wanted people to think about me. I wanted to look in everyone’s eyes and be there with them. See them and let them see me.

My emotions often rise when I speak publicly about my experience with heart surgery. That’s why I keep talking about it. In my peer coaching work with patients, I’ve seen the story can be liberating though for too many people, the story is buried and never told. There are quick comments and summaries designed to keep others at bay because they couldn’t possibly understand. Better to avoid the difficulty than be left managing someone else’s fear.

Surgery brought me to my knees - all my hidden fears and beliefs shot to the surface and it took me years to allow them to break through the thick crust of protections I created as a child. Speaking publicly is part of my liberation. When I’m honest with myself and others, there’s a connection made in the present moment that touches my heart and often sends tears streaming down my cheeks. The tears surprise, frighten, and delight me.

Midway through the interview, I noticed a few people in the room were uncomfortable and tearing up. I also noticed the full room was engaged and making eye contact. Often, at conferences, the audience splits attention between the words and the devices. Email, twitter, facebook, linkedin, news, texts, email, twitter, linkedin, txts, photos, email. Presenters vie for attention, but it’s hard to top the apps for attention. The audience in Honolulu was there, present, with Joey and me. I decided to experiment and go a little deeper. Connect more. Meet people’s eyes and attention and open up more. Opening up requires inner quiet and presence. Staying right there with no agenda aside from opening up the field of presence with everyone in the room. It’s like tuning an instrument. Matching my energy to each person and to everyone together. And to the birds, the breeze, and the ocean.

My story helps us connect. My near-death story - a heart attack, swimming in the lake a quarter mile from shore - helps jolt people out of their minds. “Wait, what happened?” People meet the story at different levels of depth, often depending on their experience with death. Their fear often rises. The fear they imagine I must have felt. I don’t know whose fear it is. In a room full of heart surgery patients, I find people are reminded of their own stories, which they’ve often tried to bury and forget. They remember the fear and pain. In a room full of founders, it feels like minds and bodies are trying to connect.

As the interview continued, Joey asked questions to tie together the experience of heart surgery with the emotional and mental health issues many founders face from the perceived stress of entrepreneurship. It takes a lot to build a company from the ground up. What it takes is an open question that founders get to consider and answer. It can take their health, ethics, boundaries, and material wealth. It can take growth, evolution, examination, and breakthroughs. It can take everything. It can lead to evolution, death, and the recognition of liminal spaces.

“Entrepreneurs see something that others don’t see, yet.” I told the audience. “At the start, it’s not clear, hard to articulate, and out of focus, but there’s a core. There’s a stubborn idea that lodges in our imaginations; deep enough we’re willing to take risks that don’t make sense to others. Bringing the idea to life requires the founder, the steward of the idea, to evolve and expand in unpredictable ways.”

The audience nodded and leaned further forward. They all knew about the obsession that grows from the powerful idea. The fever. But at what cost? Founders experience rates of anxiety and depression at much higher rates than the general population, which means founders are far more likely to experience chronic disease and, eventually, major surgery. I started to understand why I was in this room talking to these people. My story was their story. I was talking about our past, present, and future. 

Heart surgery taught me to be more honest with myself. Emerging from post-recovery depression, I became fascinated with trauma and depression. They became the stubborn ideas I couldn’t shake. I saw Trauma and its effects everywhere and for the first time.

Into my forties, I believed acknowledging trauma was admitting weakness. Feelings were thoughts to be labeled and fixed. Solve the thought, bury the feeling, and return to survival. My mind knew how to build systems and companies, but I was disconnected from my body.  My understanding of trauma was common, perhaps typical. But heart surgery had shown me a version of my future that didn’t feel right. It felt like there was more for me to do, and I needed to live to wake up. Repressing the trauma of heart surgery, I had walked a well-worn path to depression. Experiencing rather than repressing my depression, I had released the trauma, maybe multiple traumas, and seen reality from a different angle. From this altered point of view, I was able to see trauma as a character in the human story.

I was saddened to learn how common depression is among heart surgery patients and again to learn the rates are also high among entrepreneurs. Was one the road to the other? Was it my ego that wanted to offer relief or some kind of solution to the founders in this room to gain credit or a reputation as a wise elder?

I had experienced burnout twice: once in Miami Beach and once in New York City. I saw no choice but to plow through and persevere. I didn’t take a break or rest, and I had no tools or understanding of what I was doing to my body. I don’t know if I would have been able to hear anyone if they had told me about the risks of stress because I was disconnected from my body - I wasn’t listening. Stress felt like something to overcome.

Mental and emotional health issues for entrepreneurs demand urgent attention. The world needs solutions to big problems - housing, healthcare, climate, income inequality, energy - and founders, backed by private and public investors, will be the ones to steward new ideas into reality. This is a responsibility, and to accept that responsibility, founders must face the realities of what it will take. I sat on stage, in presence with my beloved audience, and shared my experience.

I don’t remember my Uber drive back to the hotel.

That night, I walked out of the hotel and through Waikiki, following the full moon. The moon pulled my body along the Ala Wai Canal towards Kaimuki. The air was warm and heavy. I was walking in a dream. I walked into the Sunrise Restaurant. They made me a special order: grilled mackerel and rice with salad. It was generous, delicious, and heart-healthy. I listened to conversations of the families, coworkers, and drinking buddies at the tables around me, but I didn’t understand the words.

In the morning, I walked to the ocean and joined my new friends for a swim. On the sidewalk near the beach, I heard someone call my name.

“Aaron!”

I couldn’t imagine who would know me here.

“Hello?” I said as two men approached.

“I was at your talk yesterday. I wanted to say thank you. I run a tech company - this is my partner.”

“I am speaking later today to a group of business students at the University. I feel nervous, and I’m not sure what I should tell them.”

“Speak from your heart,” I replied. “You can’t be wrong.”

Walking through the park that separated the street from the ocean, I passed an AA circle. Recovering men and women gathered on the grass under the shade of a giant banyan tree. I listened for a few minutes and wondered whether they were right about God. That God had saved them so they could show others it was possible to be clean. I had started drinking at an early age and struggled for years. The word alcoholic sounded like the word trauma - not for me. Too hard to admit weakness. A tear ran down my cheek as I connected with the circle. I wondered if I was dreaming.

I walked on and met David at his car across the street from the ocean. He loaned me a pair of his goggles, and we were soon joined by two of his friends, one of whom was a tech company founder who was eight months pregnant. I was the only one without a half-wetsuit, so I didn’t know what to expect. One of the swimmers strapped on a shark-deterrent anklet. I planned to stay close to the group.

I had spent the summer swimming in lakes, and I was surprised by the buoyancy of the salty Pacific Ocean as it held my body above the water. I felt like I could swim forever. We swam a hundred yards out and then parallel to the beach, resting and talking as we reached the first buoy, then the second, and third. We swam behind the break and surfers. It was quiet, and the Waikiki’s hotel skyline seemed far away. I could have stayed in the water for hours. I felt the power of the moon in the water. A current that felt like it was there just for us propelled our small group faster through the water as we swam out and then back again.

Back on shore, I dried off and thanked David and the group for welcoming me. I walked back to the hotel, spent most of the day on Zoom meetings, packed, and took an Uber to the airport for the redeye back to Seattle. I used to hate redeyes, but now they’re just another experience. Another dream. The driver was an older man who had grown children living near Seattle. He told me how his grandchildren would visit and how much they loved the ocean. He listed the Honolulu neighborhoods I should explore and restaurants I should try when I’m back. He used to work in advertising, working for retail clients, and now he’s glad he’s not so busy and stressed before Christmas.