Summary

The author reflects on the unexpected lessons and insights gained from working with a humble, risk-taking, and left-brained millionaire tech executive who serves as both a client and a mentor.

Abstract

The author, a ghostwriter, shares their experience of working with a wealthy and successful tech executive named John, who defies the stereotypical boss persona with his humility and respect for equality. Through weekly writing sessions, the author has learned valuable business and life lessons, observing John's passion for problem-solving and his willingness to take significant risks, such as leaving a lucrative job to start a new venture. The author, who identifies as right-brained and artistic, contrasts their intuitive decision-making with John's logical and framework-driven approach. Despite initial timidity and a significant age gap, the author has grown comfortable and confident in their professional relationship, appreciating John's empathy during personal hardships. The experience has provided the author with a unique blend of mentorship and a glimpse into the mind of a hypomanic individual driven by creativity and the constant pursuit of innovation.

Opinions

The millionaire tech executive, John, is perceived as humble and respectful, contrary to expectations based on his wealth and status.
John's passion for problem-solving and building from scratch with technology is highlighted as a key aspect of his personality and success.
The author admires John's courage to quit a well-paying job for the sake of entrepreneurial adventure, likening it to the hypomanic traits described by John D. Gartner in "The Hypomanic Edge."
The author identifies as a right-brained individual and notes a significant difference in their creative and intuitive approach compared to John's logical and analytical left-brained thinking.
John's reserved nature is attributed to his focus on utilizing time efficiently for his passionate pursuits, which the author respects and finds intriguing.
The author expresses personal growth and attachment to the mentorship provided by John, valuing the practical life and business lessons learned through their collaboration.

Working With a Millionaire Techie Isn’t How I Expected It to Be

Lessons driven by passion.

Photo by Juan Pablo Serrano Arenas from Pexels

There are people who are wealthy and sane, then there’s a special segment of people who are wealthy with a whole lot of crazy.

When I met this person, my perception of wealthy people was entirely different. Stanford-educated and working at one of the largest tech companies, he was too humble for the stature he carries in the society.

During my last few months of ghostwriting for him there’s so much I have learnt; we’ve had weekly lessons, like university classes to write his blog. During this journey, I’ve also gained insights about how I should approach my business and life after learning from his success and failure stories.

Here’s what make’s him so different from anybody I’ve interacted with before.

He doesn’t think he’s the boss

Even though he’s a super-senior executive. Even when he has hired a ghostwriter half his age. The boss attitude is just not there. Instead of a seniority vibe, there’s a vibe of a lot of respect and equality.

In the beginning, I was timid during our sessions. I second-doubted the work I delivered. In my head, I was so afraid of losing such a big client that my fear overruled me.

With time, as we spoke more, I got more comfortable. I gained confidence that writing is my game and what I’m great at delivering value for, and this was a consequence of John (name-changed) being empathetic.

When my grandfather passed away a few weeks ago, my colleagues at work dumped me with even more work whereas John (who pays me more than my corporate paycheck) was okay with me taking as much time off as I want and constantly checked up on me.

He takes risks that can burn him to the ground

John is incredibly passionate about problem-solving and building from scratch with tech. He has founded a few start-ups, worked in 3 major tech companies, and is currently doing incredible in his career. What are his next plans? To quit his safe job, where the money is pumping in and build another start-up.

There’s a concept called hypomania in terms of entrepreneurship. As John D. Gartner explains in his book, The Hypomanic Edge:

“Why is America so rich and powerful?

Hypomania, a genetically based mild form of mania, endows many of us with unusual energy, creativity, enthusiasm, and a propensity for taking risks. America has an extraordinarily high number of hypomanics — grandiose types who leap on every wacky idea that occurs to them, utterly convinced it will change the world. Market bubbles and ill-considered messianic crusades can be the downside. But there is an enormous upside in terms of spectacular entrepreneurial zeal, drive for innovation, and material success. Americans may have a lot of crazy ideas, but some of them lead to brilliant inventions.

Why is America so hypomanic? It is populated primarily by immigrants. This self-selection process is the boldest natural experiment ever conducted. Those who had the will, optimism, and daring to take the leap into the unknown have passed those traits on to their descendants.”

I’m not sure how many of us would have the courage to quit when we’re being paid well and enjoying the safety net. But as Gartner explains, some people have a gene of unusual creativity and the propensity to take risks. For John, he says he just needs to be on a constant adventure of building and problem-solving.

He’s extremely left-brained

I’m an artist and that’s all I have ever been. I’ve been average at studying and excellent at daydreaming. Theories don’t flow to my head as easily as my pen does on blank paper. Logic doesn’t align with me as humour does. My decision-making is more spiritual and intuitive with less logic.

As Nobel Prize winner Roger Sperry explained in his world-famous experiment, people have one side of their brain more dominant than the other:

Left: logic, facts, math, linear thinking, sequencing, thinking in words
Right: imagination, holistic thinking, intuition, arts, daydreaming, visualisation

I am right-brained, of course.

Now one day I asked John if I should quit my job and take up writing full time as he’s not just my client but also a mentor. I expected an answer from his previous experiences, telling me to follow my heart or pursue my passion… something along these lines.

Instead, he asked me to search up specific decision-making frameworks to help me figure out the answer because a situation has more to it than how the heart feels.

When was the last time you used a decision-making framework to make important life decisions? I’d never heard of them before.

He’s awfully reserved

When the right brain meets the left, it’s a disparate synergy. One side is chatty and wants to talk about life, and the other starts and ends at the time mentioned in our calendar.

John tells me he’s reserved because time spent chatting with people can otherwise be spent building something he’s passionate about. The left-side brain is always at work, and the hypomanic edge is always in the spur to create something new.

Come to think of it, they too are dreamers because just like artists, they’re constantly creating in their head in hopes for it to become reality. Wow, this was one hell of a plot twist.

I may just be getting attached…

In the last few months, the things I have learnt about work and life are the things university should’ve taught me. I have heard experiences of John failing so often with his business ideas, but he never stopped building new ideas.

He takes a punt on himself and his career every other year because he’s so driven with his passion.

In all this nerd-ness and differences between left and right, I’ve grown. But I’m also new to this freelance writing world, and I suppose regardless of how much fun it is and how fulfilling it is, clients have to come and go.

But these lessons are the ones I will carry forever.