Chief Everything Officer

This book is the business memoir I have been waiting to write for many years but needed to wait until I was no longer CEO to write it, because it has more tales of my failures than successes. I was successful because of my mistakes. I learned more from them than my wins. I hope that you can as well.

My story as CEO began while I was a student on campus.

The year was 2007, and I had just had the most exhilarating year. The previous summer I did a work exchange in the UK and was using a cell phone like never before. Everyone in Europe texted one another. A lot. And it was addictive; I found myself looking at my phone constantly.

I also went on a study exchange in Hong Kong that year—my first time in East Asia—where I would watch TV on my phone while riding the subway, at a time when people were barely using cell phones for anything more than making phone calls in North America.

That was the initial spark for me. I realized that one day cell phones would be used primarily as consumption devices, not communication devices.

Studying Software Engineering at the University of Waterloo, in Canada, I was in BlackBerry’s backyard. At the time, they were Canada’s most valuable company and the most widely used smart cellphone in the world. Celebrities and politicians, including Barack Obama, Justin Bieber, Oprah Winfrey, Madonna, and more would all talk about how they were addicted to their “Crackberries.”

The chancellor of my university was Mike Lazaridis, founder and CEO of BlackBerry, and as a student leader on campus, I got to spend time with him and learn more about smartphones slightly ahead of the rest of the world.

I first dreamed of becoming a CEO at the tender age of six.

Whereas most kids dreamed of being a firefighter, astronaut, doctor, or superhero, my dream was to be in business. And to be the boss. Whereas most kids played restaurant, airplane, or house, my younger sister and I played office. I was busy making pretend phone calls, scribbling letters, and holding unimportant meetings. Fast forward to the present: things haven’t changed very much. At the age of ten, I was banned from playing the board game Monopoly. My sister, only one year younger than me, was the loud one back then. Tired of always losing to me, she waged a campaign amongst our friends and cousins against playing the game with me ever again. Her campaign was successful.

Fast forward to the present, I have a real estate business called Park Place, and play real-life Monopoly.

Business for me has never been work. From the age of six to present day, business for me is a form of play. And I love it.

In the Blood The year was sometime in the early 1800s, my great-great-great-grandfather on my dad’s side started one of the first bicycle stores in India. It was the original franchise model. His sons moved to different cities, each starting another bicycle store under the same name. Their sons continued the tradition, creating one of the earliest franchise networks in India, which gave them incredible negotiation leverage with suppliers as one of the biggest distributors of bicycles in India, at a time well before cars crowded the streets. The franchise lasts to this day—albeit a humbler size. My grandfather on my mom’s side was also in business. He was in the sugar cane business, buying the equipment and leasing it to farmers for growing sugar cane and processing it, turning it into all sorts of consumer products. Nearly all my aunts, uncles, and cousins in India, Canada, and the US, went into business for themselves. Business was so common in my family that it was rarely talked about at family gatherings.

Into my early teenage years, I began to imagine myself as CEO of a country one day, instead of a business.

My morning routine as a teenager involved waking up early while my parents were still snoring and my sister fast asleep, and sneaking downstairs quietly. Opening the front door, I would tip-toe on the snow-covered porch to grab the newspaper, The Ottawa Citizen. (Fun fact: decades later, they would be paying me to launch their mobile app and run their digital ads.) I would then sit on the carpet in the living room and read the entire newspaper, front-to-back, and fold it up neatly afterwards for my parents. Growing up in the capital city, I was exposed to politics everywhere I looked. Reading the paper every day, I knew what was going on locally, nationally, and internationally. I was interested in everything and began to wonder about one day going into politics. The Crush The year was 1996, and I was eleven. Only one student had their hand up. Her name was Nicole, and she was the first girl I had a serious crush on. Butterflies in my stomach, I put up my hand after the teacher finished asking the question. Maybe this was my chance to talk with Nicole, I thought.

As it happened, I had accidently put up my hand to be a class rep for student government. It was my first elected position, which I got by default, as there were only two of us interested and, luckily, two positions to fill.

Each week, we met with all the other class reps to discuss what was happening in the school. We’d hear about events like school dances, upcoming sports competitions, new rules for students to follow, and, of course, when the next bake sale was. There was always a bake sale.

My first footsteps onto the University of Waterloo campus marked the beginning of my journey into software engineering.

I had always known through high school that I wanted to go to the University of Waterloo and study engineering, as I had several older cousins who were role models for me, having already gone down that path. However, I didn’t quite know which type of engineering to pick. The initial spark for my final choice was a friend I made at Shad Valley, also known as “summer geek camp” in high school.

My friend Nishant had a bigger influence on me than he’ll ever know, unless he picks up this book. He was one year older than me and I admired and looked up to him. He was studying software engineering, so I decided that would be the best option for me too. How wrong I was.

By the third day of my first year, I was intimidated: everyone was leaps and bounds ahead of me and crazy smart. While I had dabbled in software before, the sheer depth and breadth of the software experience others had overwhelmed me. I realized at that moment that I was not going to be the best software engineer. However, I knew that I wanted to be the best at something. That is when I turned my attention to another domain, something I knew I could excel at. The Club The year was 2003. Having been raised in a family that embraced entrepreneurship, I naturally gravitated toward the world of business.

Waterloo was, and still is, renowned as a leader for innovation in Canada and the world. Yet, when I probed deeper, I found a surprising void. There was barely anything for undergraduate students to interact, engage, and be inspired by the world of entrepreneurship.

From the start of my university journey, one thing was clear: I wasn’t destined to fit into the confines of a nine-to-five cubicle life. While many dreamed of a stable job, I wanted to pave my own way.

One of the reasons I chose the University of Waterloo was for its Co-operative Education Program, co-op for short. Waterloo’s co-op meant that every other semester, I would work as a well paid intern at a real company. This allowed students like me to weave in and out of the workplace, gaining insights, skills, and perspectives. Picture graduating free from student loans, armed not just with a degree but two years of diverse, hands-on work experience at five to six different companies. My internships inspired and shaped me in surprising ways.

Working Corporate The year was 2004, my first foray into the professional realm took me to the heart of Canada's financial district at the Bank of Montreal. At eighteen, the corporate allure was undeniable. Slipping into dress shoes, matching them with sharp dress pants, and wearing a crisp button-down shirt each morning gave me a sense I was doing something important.

But as days turned into weeks, I began to realize that this formality covered a deeply rooted complacency. Conversations with coworkers seemed like reruns—weekend plans, the latest episode of a popular TV show, and an almost ritualistic grumbling about politics. The passion to innovate, the hunger to push boundaries was absent. It struck me that size wasn’t always an asset; it could be a liability. I was uninspired by being at such a big company and decided early on that I would be better suited to a small company.

However, I was hopeful and excited as I embarked on my second internship with TELUS, one of Canada's biggest telecom companies. What truly set this experience apart was the gravity of the role I found myself in. Within the giant company, I was part of a six-person project management team overseeing 2,000 people. The magnitude of our decisions was both daunting and exciting.

The word sales evokes the tired image of a used-car salesman who will say anything to get a deal. It has come to develop a poor reputation that is unwarranted. A Chief Everything Officer is always selling, but not in a sleazy used-car salesman way. As CEO, I’m selling to clients to do business with me, and to continue doing business with me. I’m selling investors to come along for the ride with me. I’m selling to potential competitors that I lead the market and they shouldn’t bother trying to enter. I’m selling job opportunities to potential team members. I’m selling to existing team members the reasons for continuing to work with me and why they should bring their best to the table every day. I’m selling stories to the press in a way that aligns with my interest. I’m selling the banks, lawyers, and auditors to prioritize me over their other clients. I’m selling a reason to vendors and suppliers for giving me a better deal in hopes of a longer-term partnership.

A CEO is always selling. Always.

The bad reputation that sales has is often associated with people who are pushing a product or service that's not useful or needed. A CEO fundamentally believes that what they are selling is useful. Every entrepreneur needs to identify as a salesperson; once they have, they can then be shameless about owning this part of their identity. And refining it to be really good at it.

Over fifteen years, I signed over five hundred enterprise client deals, so if my close-rate was a generous 20 percent, I likely pitched over 2,500 prospects. I became very comfortable with hearing “no” and learning how to not take it personally. Many technology entrepreneurs come from an engineering background and may not be naturally great salespeople. That was not my situation, but I know it is often the case for others.

There are secrets to business that are rarely discussed publicly. Pricing is one of them. A major lesson I’ve learned is that it is not a one-size-fits-all approach, contrary to popular belief.

When two clients, both purchasing the same product, end up paying different prices based solely on their capacity to pay or the value the product has for them, it breaks the logic, especially for engineers and finance people. It’s not a bug; it’s a feature though for early stage B2B businesses.

My team constantly challenged my decisions with pricing. Every month’s end, when invoices went out and revenue forecasts were analyzed, eyebrows were raised and the same question resurfaced: “Why is our pricing so inconsistent?" While the confusion was understandable, my stance remained unyielding: my strategy was to generate revenue, and how that happened was secondary. Get What You Can The year was 2007. I got so wrapped up in the energy and thrill of starting something, that basic principles, like pricing, slipped through the cracks. It showed with Canadian Business, our first client.

They had given us the nod for a pilot project. However, my focus revolved around the “how to,” not the “how much.”

After one meeting, the VP of Digital Media walked me from the boardroom to the reception to see me out.

“I can probably get you some budget for this pilot, what do you need?” he asked. At that moment I realized that I hadn’t brought up pricing or even asked for money. I had completely overlooked this part of business. Unsure of what to say, I responded with, “Well, how much budget do you have?”

He paused.

“About $10,000 for a three-month pilot”

I was sitting in my bedroom at my parents’ home while visiting for a weekend. I was still in school and getting ready to start my business, for which I needed a name. Staring out the window, I saw one of our cars in the driveway. It was a Toyota Camry. I started to reflect on the names of car brands. Jaguar is just the name of an animal, I thought.

I opened up Google and typed in “names of animals.”

The first search result was a link to Wikipedia and the page for animals. I clicked the link and started to scan the page. The names of animals were arranged alphabetically. I got to the letter P and saw ‘polar bear’ and liked the word “Polar.”

Easy to say. Easy to spell.

I went to a domain registration site and typed in polarmedia.com. It was taken. I paused and then typed in polarmobile.com. It was available.

I had it. That would be the name of the business.

Over time, I quickly developed a marketing story for the brand. The first logo was the tip of an iceberg because only a small proportion of an iceberg can be seen above the surface: there’s more going on beneath. That metaphor was representative of our team as a group of young students who had more depth than it might appear. It was also representative of our product: a tiny mobile app with a large server-side platform that did all the heavy lifting out of sight.

What I love about marketing, even more than sales, is that it can be an efficient “one-to-many” way to connect with clients versus “one-on-one,” which, after fifteen years pitching thousands of prospects, can get a little tiring. My framework for business marketing is quite simple and aligned to a three-stage funnel.

My father is an ideas person, always bursting at the seams with ideas for every industry, every market, every geography—and every business. People who work with me know that I, too, have an endless stream of ideas. It is a generative activity that fills and fuels me.

My mother, on the other hand, is the most stubborn person I know (after me, that is). Like a dog with a bone, she doesn’t give up once she’s set her mind to something, regardless of how important or unimportant the task is. People who work with me know that I, too, never give up.

It’s a dangerous combination to be able to come up with new ideas and have the confidence to try and execute them, and it gets me and my businesses into lots of trouble. Repeatedly.

Takeoff and Landing The year was 2008. I woke up at 8:00 a.m., having only gone to bed a few hours earlier. When I glanced at my BlackBerry, I saw I had seven missed calls and there was a barrage of messages waiting for me.

I sighed.

“This is not going to be a good day,” I said to myself.

It was January 24, 2008, and I was three months away from graduation. It was also launch day for our first mobile apps, for Canadian Business and Maclean’s. It was the first time any media publication had been put onto a smartphone. At least, it would have been the first time, had it worked.

“The app is not working, Kunal.”

That was the first of many voicemails I had from Kim, from Canadian Business. As I scanned the text messages and emails, it was clear the app was not working.

I started my business by spending $20,000, spread out over eight months, on my parents’ credit card without telling them. Had I known that I would be putting $20,000 at risk at the age of twenty, I probably would have decided not to do it. I went on over the years to raise over $80 million in capital for my business from angel investors, venture capital, private equity, and traditional banks. Had I known it would take this much capital to get the business to where it is now, I probably would have been too intimidated by the prospect to go for it.

There are generally more reasons to not do something than to do something. I am glad I paid less attention to the reasons for not doing something. How Much The year was 2008. I was the new guy and also the kid in the room. Everyone was twice my age. Some were three times my age.

A few weeks out of school, I had been invited to join a peer-to-peer CEO forum where a group of seven CEOs met each month in private to discuss each other’s businesses and lives, and lend support and guidance to each other. It was like a personal board of directors.

As I was new to the group, it was my turn to present my business that day. Over the course of the afternoon, everyone picked apart my business, to which my inner response was often, “Ah, you’re too old to understand how tech companies work.”

There was one comment, though, that penetrated my ego and stuck with me. “You need to pay your staff,” one fellow CEO urged me to consider. I explained that we were all recently out of school, most living at home with their parents, and no one needed a salary. Another CEO jumped into the conversation, saying, “They may not need one right now, but they will within a few months. You need to have a plan for how you’re going to pay your people.”

My mom would often congratulate me on my business success, saying, “You deserve this. You’ve worked incredibly hard for so many years.”

It was well intentioned, but it never quite landed for me. The reason is that I know so many people who work incredibly hard and do not achieve the business success they aspire and hope for.

Hard work alone is not sufficient. The next logical assumption about success is that it must be the idea that matters. Hard work plus a great idea equals success. Again, I don’t buy it. Most of my ideas have proven to not be that great, and I know many people who work hard and actually have great ideas.

Hard work and great ideas are not sufficient. The next thought, then, is that it’s the team that matters. Hard work, a great idea, and a solid team are what it takes. Again, I don’t buy it. Yes, my team was solid but we were kids right out of university with no absolutely no business or industry experience. I know many people who work hard, have great ideas, and an amazing team. There are countless failures that check all of these boxes.

What else can it be then? There is an element of luck for sure. But the intangible factor that I believe to be my greatest secret for success is simple. Adaptability.

Time and time again, I adapted the business. To do so, I adapted myself so that I could rise to the latest challenge or opportunity the market presented. Time To Change The year was 2013. It was a Thursday morning, and I woke up earlier than usual in my hotel room in New York, where I was once again trying to drum up business. I took a quick glance at my iPhone.

Each person I’ve interviewed, each handshake I’ve exchanged, and each team I’ve led has imparted invaluable lessons. Through all of these experiences—good, bad, and sometimes downright comedic—I’ve gathered a treasure trove of insights. But if there’s one overarching takeaway, it’s this: people are complex.

The first hire for Polar Mobile was me. The next half dozen were co-founders. I learned from my high school co-president chapter that any organization needs a single leader in charge. I saw firsthand how having two people at the top slows everything down. When Jenn and I were co-president, it didn’t bring out the best in either of us. I’ve also witnessed second hand the number of startups that have failed due to co-founder disagreements.

From the start, I was the CEO and Founder of Polar Mobile, and several other people were given the co-founder title; however, it was clear to everyone that one person would be in charge, and that was reflected in the structure, shareholder ownership, and culture. At the end of the day, when the difficult decisions need to be made, one person needs to feel responsible for them. I find it’s too easy with decision-by-committee to end up with suboptimal choices.

Over twenty-five years, including my student leadership days and in running Polar for fifteen years, I have been involved in hiring over 1,000 people to join me. This has brought with it the satisfaction of making those “magic hires” and the disappointment of “tragic hires” that didn’t work out, sometimes catastrophically. If my successful hires added to my confidence and trust in my judgment, my not-so-stellar ones taught me humility and the value of reflection. As the cliche goes though, I’ve learned more from my bad hires than my good ones. Here Is Your Desk The year was 2008. The early days of Polar Mobile had a certain charm that’s tough to put into words. Our first office was a tiny space situated in the heart of downtown Toronto, nestled in a meeting room within someone else's business. The setup was intimate. Our chairs were so close that anytime someone stood up, their chair would bump into someone else’s. No one had enough desk space for a second monitor. We didn’t care at the time, though. There was magic in that cramped room. The buzz, the unrealistic dreams, and shared ambitions to create something that we would be proud of. We genuinely believed, with every chair bump, that we might change the world, one mobile app at a time. Once Greg invested, and we had more capital at our disposal, the hiring began.

As a Chief Everything Officer, I have written dozens of termination letters. If you had asked the younger version of me about firing someone, I might have cringed, shuffled my feet, and changed the topic. It’s not a rite of passage any leader relishes; nonetheless, it’s vital to be comfortable with parting ways with talent when it is no longer a fit. And no one tells you how to do it.

Firing someone is a dance of the personal and the impersonal. On one hand, it is deeply personal—you’re potentially shaking the roots of someone’s financial stability and their professional confidence. On the other hand, it’s business: a rational decision made for the health of the organization.

Over the years, I’ve had many come to me months or even years after I let them go, expressing their gratitude. While being let go is daunting and destabilizing, for many it is a needed push out the door so that they can walk into a more interesting door. They discover roles they are better suited for, often thriving in environments they’d never have ventured into if not for that nudge out.

How an employee is treated during their exit speaks volumes about a leader and a business. Ensuring they leave with dignity, respect, and a safety net not only benefits the individual but sends a powerful message to the rest of the team that they will be taken care of.

Leadership isn’t just about driving growth or innovating. Sometimes, it’s about making the hard calls, standing by them, and learning to find the glimmer of positivity even in the most challenging decisions.

I often am asked to speak with university students about my entrepreneurial experience. One of the questions I am most frequently asked these days is, “I am working on a business, should I drop out of school and pursue it full-time?” My response is a strong “no” every time. I share with them that I almost dropped out of university on two separate occasions. I found software engineering challenging, as my interests were in business and entrepreneurship. I was also impatient and did not want to waste time on academics. However, getting my degree and passing every course taught me how to do things I didn’t want to do.

Alignment is everything, and I’ve learned the hard way how to get it. Understanding alignment and how to maintain it has been a long journey for me. Alignment breaks down into four categories.

Market alignment. Do the clients want what we have?

It’s easy to throw sheer force and determination as an entrepreneur behind selling the product, thinking “I just need to work hard”

. I’ve had many instances where the market was clearly telling me “no” and I wasn’t willing to accept it. In every instance, the market was right and I was wrong. In every instance, I wasted a lot of precious time and resources.

Team alignment. Do people want to work for me?

Continuing to motivate, inspire and excite a team is part of the job. I’ve noticed stretches where I’d be traveling 80 percent of the time for weeks on end, and the team felt disconnected from me and the vision. It started to show through in the productivity and pace of everyone. As a market-facing CEO, my attention was always directed towards our clients and the team was secondary. I’d cancel an internal meeting on a moment’s notice if a client meeting popped up. I learned over time the importance of communicating effectively with the team, a balance of optimism and realism, while not taking my eye off the clients.

Product alignment. Do we have the right investment profile?

There are different leadership styles. It took me nearly a decade to get comfortable with my style, which, like many ideas presented in this book, are countercultural. I’m no longer a big believer in collaboration for the sake of collaboration. It is likely an unpopular statement; however, it is my truth, informed by my experience. I have wasted a lot of my time and other people’s time in the name of collaboration, teamwork, and cohesion.

Deep down, I believe smart and talented people just want to be told clearly what to do. The ambiguity frustrates them. People like the challenge of figuring out how to get a goal accomplished, but they want to be told what the goal is. It’s intellectually lazy on management’s part to ask the team to devise the strategy. I was intellectually lazy for a long time on this topic. It requires a lot of courage to set a strategy when you don’t know if your company is going to achieve it. It feels safer to be collegial and come up with a strategy together, as a team. If it didn’t work, the leader doesn’t feel solely responsible for it.

However, more times than not, what a group comes up with reflects the lowest common denominator. And you want someone, anyone really, to feel responsible for the decision so that they are seeing it through. Just look at the United Nations or any other decision-by-committee institutions. A growing business that needs to act quickly, take risks, and be dynamic needs a leader at the helm calling the shots and getting everyone in line. Quickly.

Managing Crisis The year was 2009. Only a year into our venture, we were overwhelmed—not by failures but by an unexpected surge in demand. The iPhone had taken the world by storm, and every major media outlet wanted a piece of the pie. And who did they turn to for their app needs? Us.

“I heard you, but I didn’t believe you. Now I do.”

That was what Leah, our Chief Revenue Officer, told me a few weeks after she started working with me.

I had told her during the interview process of how anti-meeting I was. She reflected back to me that most leaders talk a big game on this topic, but she had never seen anyone actually walk the talk. Until she stepped into my team. Time Audit The year was 2014. It was the end of the year and my thoughts gravitated toward the concept of time. Amid the year-end festivities, there was a nagging feeling that time was slipping through my fingers like sand. In a world where time is the one thing you can’t buy more of, it seemed to be the very thing I was always short of. I stared at the screen of my laptop, my fingers hovering over the keys. The digital calendar was a stark reminder of my frantic pace, with every slot filled, leaving little room to breathe. Yet I felt I didn’t have enough time to do everything I was meant to have done that year.

I became curious to figure out where my time went. Creating a spreadsheet, I meticulously started categorizing every hour, every meeting, and every activity, dissecting my year, hour by hour. The buckets were Sales, Account Management, Administration, Travel, Internal Meetings, and a few more.

As the numbers started to add up, I was beginning to dread what the data was going to tell me. Where I spent my time is not where I thought I spent my time. As the lead salesperson in the business, I assumed that I was spending at least one third of my time with prospective clients. I was wrong. I had spent a mere 10 percent of my time on sales. On the other hand, I had spent 30 percent of my time in internal meetings. It was a hard pill to swallow.

Navigating the world of business isn’t a solo journey. My guiding stars have always been advisors, mentors, and board members. They’ve been instrumental from the get-go. Back in the day with Impact, the student entrepreneurship organization I started, our advisory board was a golden ticket. They gave us credibility and access to circles we could only dream of, yet desperately needed to advance the mission. As Polar Mobile grew, my needs shifted. It’s like starting with training wheels on your first bike, but as you get better, you replace them with faster gears. The early days required a board to guide and protect. Later, it was more about pushing boundaries and setting bigger visions.

In the beginning, each board meeting was a learning session, filled with strategy and some lessons learned the hard way. But as time went on, these sessions evolved into strategic discussions.

I learned the importance of having the right voices by my side, at the right moments. Don’t Party Together The year was 2008. I was knee-deep in launching the business, my BlackBerry pals nudged me toward Gary.

A veteran in the mobile world, Gary had a lot to teach me. With each of our conversations, the depth of his wisdom was evident, making me wonder why he’d even give a young upstart like me the time of day.

Gary was like the North Star in the sprawling universe of mobile tech. To be frank, I was just trying to plot my tiny spot in that vast sky, and Gary, well, he was a legend. But here’s the twist: he was oblivious to the profound impact he had on my journey. “Go to the US,” he'd often advise, his words echoing with the weight of experience. And though Toronto was home, we usually met in the streets of New York. The city’s skyscrapers stood tall, much like my aspirations, fortified by Gary’s counsel. And somehow, he always knew the right doors to knock on.

Being a Chief Everything Officer can feel like I’m the sole waiter at a restaurant and everyone has a different menu.

I’m not my own boss; I work for everyone else, but myself.

I work for my team, and everyone comes to me with their problems. I work for my clients, and they all come to me with their problems. I work for my investors, my competitors, my industry, and practically everyone I interact with. Everyone wants something from me. Collectively, they want everything from me. Being a Chief Everything Officer has, therefore, meant giving my everything to my business.

That involves sacrifice and trade-offs. That’s sometimes staying up late in the office instead of going out partying with friends. That’s sometimes allowing the business to occupy the most valuable real estate I have—my mind—on weekends, evenings, and vacations. It’s being all-in, all the time.

Being a Chief Everything Officer has also meant having everything about me tied to the business. My identity. My net worth. My time. My energy. Everything about my existence has felt, at times, like it was about the business. At times, I loved it. At times, I hated it. But it didn’t matter, as I chose this path, and it’s not a path one can easily stray from. OGs Your underlying motivation for being an entrepreneur shapes the type of entrepreneur you are. Over time I’ve learned there are three types of entrepreneurs. Each has distinctive characteristics and motivations—and specific strategies for how they navigate the business world.

The first type is what I call the OG Entrepreneur. OG is short for Original Gangster. There’s something about these individuals that is deeply inspiring. They’re often propelled by an underlying motivation and drive, and burning desire to prove themselves. More often than not, this desire is focused on proving themselves to their parents and being seen as good enough in the eyes of those who they depended on for love at an early age. They carry a chip on their shoulder and channel it in a determined way.

“How should I be a CEO?” my friend asked me innocently one day many years ago. The simple question prompted me to reflect more deeply on how to be a CEO. I had never been asked and started to think about how to explain the role to someone who wasn’t familiar with it.

There are so many different dimensions to a Chief Everything Officer: sales, marketing, client services, product, engineering, finance, HR, legal, governance, fundraising, management, culture, and the list goes on.

The simple label of CEO can take so many different shapes and sizes. However, I boiled it down to a simple framework. There are three basic roles the CEO plays, at the core, and you can imagine them in a Venn diagram overlapping with one another. Founder Leader Manager During a given year, given month, or given day, a CEO may be somewhere different in this diagram and focused on one role over the other, based on whatever the business needs at that moment.

Founder The hat I wore most often at the start of my journey was that of a founder. Founders see what others can’t. They spot opportunities before they become visible to the market. They gravitate towards interesting problems to solve and often chant, “This can be better.”

They don’t just find solutions; they create them from scratch. The moments when I was in founder mode were most memorable for me. At the start of our business, I became fascinated with mobile devices. I didn’t see them just as phones, but as a way to access information. We started building mobile apps before they were a thing.

All plane rides start with the same safety briefing: in the case of an emergency, put on your oxygen mask first before helping others. In life, too, I’ve had to learn how to take care of myself first, so that I can take care of the business. My tool for taking care of myself over the past ten years has been mindfulness. My journey into mindfulness was somewhat serendipitous, more by chance than by design. When I stumbled upon meditation during a yoga retreat over ten years ago, it felt like opening a door I didn’t even know existed within me. Suddenly, I was face-to-face with my own thoughts, my internal narratives, and my subconscious musings. It’s funny how sometimes the most profound revelations arise from the simplest experiences. Those first ten minutes of a yoga class were merely the beginning. Over the next decade, meditation became an unwavering pillar of my daily routine. More than closing my eyes and seeking tranquility, it was an exploration of the self; a deep dive into the corners of my mind.

While the exterior calm had always been a part of my personality, meditation offered me an inner stillness. The chaos of the world outside—the frenzied deadlines, the ever-changing business landscape, the inevitable curveballs—began to lose their edge.

And as I ventured deeper into this practice, its influence seeped into my interactions. Colleagues began to notice a subtle yet undeniable transformation. Inquiries soon followed.

“What's changed?” they’d ask, picking up on the newfound serenity that cloaked my decisions, my conversations, and my reactions. To their observations, my response was always simple: “Mindfulness.”

It was beautiful to witness the ripples of my personal exploration touch those around me. Meditation was no longer my solitary refuge; it became a shared conversation, a collective curiosity. The tranquility I found within began to echo in my team’s dynamics, fostering a more centered, thoughtful approach to challenges. As meditation became a bigger part of my identity, I naturally started to bring it into the business. We started to have weekly team meditations that I would lead—long before mindfulness in the workplace became a trend. I would start client meetings with meditation. Board meetings started with a short meditation. It became my signature, authentic to who I was at that moment. Literally thousands of people in the industry have meditated with me now.

Money is a rarely talked about topic, yet its influence on everything is clear. It holds both tangible and intangible power.

Many shy away from discussing it, partly due to societal norms, and partly due to deeply ingrained beliefs surrounding it.

For most, their professional journey begins with a job and a paycheck that arrives at the end of every month, marking a routine cycle of effort and reward. But for me, raised in a family of businesspeople, the contours of a typical job never quite fit me. Instead, I started as an entrepreneur right out of university, so monthly salaries and traditional roles are foreign to me.

To think like a business owner is to perceive the business not as a separate entity but as an extension of myself. To think like a business owner is to blur the line between personal and professional. With this mindset, the concept of money also transformed for me. Every financial decision, be it an investment or an expense, feels personal. Whereas at the start of the journey I was comfortable with burning money, like a typical tech startup, I matured over the years and fell in love with running and owning a profitable business. It is healthier for the business and for me as Chief Everything Officer. Cash In the early years, I prioritized the business’s financial wellbeing over mine. And that was a mistake, looking back.

When we successfully raised funds in September 2008, the other members of the founding team, who had worked diligently without any monetary compensation for months, started drawing modest salaries. I didn’t.

While our revenues climbed in the coming years and reached over $3 million by year three, and our business grazed profitability, I remained content without a paycheck. I shouldn’t have been.

As human beings, so much of what drives us is connection.

Sitting in the seat of Chief Everything Officer from my early twenties to my mid-thirties, how I connected with people often revolved around my professional identity. It’s been a journey for me to learn how to build relationships, both inside and outside the business, both with and without my identity as a Chief Everything Officer. However, there is no doubt in my mind that my role impacted my personal family, friends and romantic relationships in meaningful ways.

Family When I got into business, I had a fear that it may not succeed. However, I never had a fear that my family would judge me for trying. Quite the opposite, actually: they might have judged me if I hadn’t tried.

My relationships with my parents, sister and brother-in-law have taught me a lot about the importance of unconditional love and support. Every time I hit bumps in the road, my parents saw the failures not as markers of any ineptitude but as lessons for growth. They understood the unpredictable nature of businesses and respected the courage it takes to keep trying, even in the face of adversity.

Beyond my immediate family, my extended family also provided a cocoon of support. During family gatherings, cousins, uncles and aunts genuinely inquired about my business, offered their own experiences and insights, and celebrated the milestones with me. These interactions reinforced the idea that my worth wasn’t tied to the success or failure of my business. My worth was in the person I was becoming through the journey.

I remember times when I would vent to my older cousins about a particularly challenging period, and they would listen patiently, often sharing their own stories of struggle, reminding me that business is cyclical, and tough times can lead to better days.

There were moments I wanted to quit but knew that I couldn’t. There were moments where my ownership in the business had dwindled and the business was not worth very much, which effectively meant I had very little financial motivation to stick around. However, the loyalty I felt towards the dozens of team members, the hundreds of clients, and dozens of investors meant that I was not going anywhere.

There were also moments when I pictured myself as Chief Everything Officer for the rest of my life, continually pivoting, finding new layers of revenue growth, and making more money for the business and myself along the way.

The Motivation In 2020, I began to think about how to replace myself.

After so many years, I had gotten the hang of the CEO thing and was quite comfortable in the role. I had just fired my board, the business was massively profitable, and revenue had grown 65 percent the previous year. We were on fire. And yet, my motivation to find the next CEO came from a place of frustration. I was frustrated that the business was still not living up to my expectations. I saw the potential and felt frustrated that, despite my best efforts, we were not realizing it or coming anywhere close to it.

Over $150 billion dollars was spent annually on social media advertising. And our products enabled media companies to tap into that market to increase distribution across the entire internet. Collectively, our customers were generating a few hundred million dollars annually in revenue from our product: barely one tenth of one percent market-share. Our business should have been ten times the size, and even then, we would only have had one percent of the market.