Connecting The Dots : Part 1

The first 26 years of my life before discovering entrepreneurship - tiger parents, engineering degrees, and iPhones.

Welcome to That Dude Denis, a newsletter about a dude who left the Bay Area and moved to Paris. The idea is twofold:

1. To share my experiences in the most open and transparent way possible as I try to become an entrepreneur for the first time, and

2. To tell you about some important steps in my life that have led me to embarking on this journey.

My objective is simply to share my perspectives and experiences with you in the hopes that something may help you in some way, that’s all. If you’re in Big Tech, startup-land, or just interested in entrepreneurship, this stuff’s for you.

And if you haven’t yet subscribed but you like my stuff so far, subscribe here and follow me on Twitter - wouldn’t want you to miss any of the good stuff that That Dude Denis has in store for you :

Last week, I talked to you a little bit about the reasoning behind our move from Cupertino to Paris, almost 2 years ago. This week’s issue is Part 1 of a two part series that should help you understand a bit more about how moving to Paris fits into my entrepreneurial journey - over these next two posts, I’ll try to explain how I’ve become inspired to become an entrepreneur now at age 29 despite having had a truly non-entrepreneurial mindset and background for many years. This week is all about the “dark ages”, the first 26 years of my life I spent in ignorance of the entrepreneurial path.

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🤯 Wow, so I’ve been blown away by the mostly positive response to the post I wrote last time - very unexpected, to say the least. It was my first ever piece of long-form, semi-serious writing, and my first foray into sharing my life and my thoughts publicly, and so it means a lot to me that so many of you (90 signups!) found it entertaining and interesting. In the name of openness and transparency, here’s the stuff that you collectively enjoyed from my first post and the stuff that could’ve been better:

✅ casual tone + sense of humor

✅ brutal honesty + transparency

✅ little tidbits of knowledge / references

❌ too long

I love getting this kind of feedback from you, so keep it coming - it’s the best way for me to improve my writing, and I promise I’m not just begging for compliments.

If you thought the first post was too long, 1) I completely agree with you, and 2) you’ll be glad to know that I’ve made this post a bit shorter! 💪 Yes, I sort of cheated by simply splitting the post I had planned into 2 parts, but hey, the end result is a post that is a decent amount shorter, probably short enough that you can finish this in one toilet sitting without your feet getting tingly. 🤭 I’m releasing on a weekday, so I apologize again to your boss if you’re reading this while you’re supposed to be working, but at least this time, it’s shorter.

So let’s get right into it. What’s today’s issue all about? We’re turning back the clock and taking a look at my first 26 years of life to give some context into why it’s taken me this long to discover entrepreneurship.

Tiger parents

If you’ve ever met me (at least any time before this year), “entrepreneur” was probably not one of the words you’d have used to describe me to someone else. Quiet, laid-back, calm, relaxed, hard-working, funny, sure…but entrepreneur? No way. When I think “entrepreneur”, I think of someone with a go-getter attitude, always with a million thoughts and ideas flying around in their head, with the energy and motivation to do all of them but not enough time in the day to actually get anywhere close. That just wasn’t who I was.

I had a fairly standard Chinese-American upbringing, one that emphasized hard work, sacrifice, perseverance, and dedication over creativity and fun. I lived a very structured, organized life, one carefully constructed by my loving parents to give me the best chance at having a successful future. They were tiger parents, in both the literal (born in ‘62 for you Chinese Zodiac fans) and figurative (Amy Chua) meanings of the term. What that meant for me, was that my life was essentially a to-do list, with tasks and goals constantly being checked off only to be replaced by new items.

In 2011, Amy Chua wrote a book called “Battle Hymn of the Tiger Mother” which popularized the concept and term “Tiger Mother”. I never read it, but I do remember reading her article in the WSJ titled “Why Chinese Mothers Are Superior”, which really shined a spotlight on the Chinese approach to parenting vs the Western approach. The article and book generated tons of heated discussion and debate, but I remember thinking that it hit the nail right on the head. It’s honestly a must-read if you’ve always wondered why we weren’t allowed to do sleep-overs with you.

In that kind of environment, it was difficult to develop and exercise my creative thinking muscles. My parents more or less took it upon themselves to plan out the best path forward for me, and all I had to do was pull my weight and execute. They made it easy for me to focus on what we thought was most important at the time: excelling in school and on the tennis court in order to have the best chance at attending a top university. That was the ultimate objective, the key to a truly great and wonderful life. Figuring out a way to make 5 bucks a week selling candy to the sugar addicts in middle school simply had no place or value in this plan of ours.

As with all things in life, there are of course two sides of the coin. Even if my creative thinking muscles were slightly under-developed, the trade-off was that I developed an impressive capacity to put my head down, work hard, focus, and truly dedicate myself to achieving goals. It’s funny, my mom loves to tell me (even to this day!) that I became one of the top junior tennis players in the country not because I was more talented than the other kids (because I wasn’t), but because I worked harder than them. I personally like to think that it’s at least partly because I had a mom that pushed me harder than theirs did.

I had no entrepreneurial influences growing up, and that’s perfectly OK. My parents are research scientists. It’s not a profession they chose because of passion or interest, but a profession they chose because of the opportunities it meant for them, an escape from China to a more promising life in America. So do I wish they were small business owners, or that they had taught me more about running a business as a kid? No, not at all. Today, thanks in large part to the upbringing they gave me, I’m in the fortunate position of being able to choose a life of my own, even if it’s one with no stable salary and a high likelihood of failure.

Like many other Asian-American households, my family adhered to a fairly standard story of success and how to get there - we prioritized results, in both school and sports, over more creative endeavors. And so, with a very structured upbringing and without any inspiring entrepreneurial figures in my life, it’s no surprise that I left high school fairly ignorant of the existence of a different possible life journey, that of the entrepreneur.

Opening the door

And somehow that remained more or less the case even after I left the piano, the Chinese lessons, and the rigid rules of my tiger parents behind and found myself on the campus of Stanford. There, I was finally free to make my own plan, to set my own schedule, and to choose how I spent my time, and yet in many ways I remained tethered to the path that my parents had laid out for me.

At Stanford, the buildings are named after famous tech entrepreneurs (the ones who were generous enough to donate their money). You’re constantly reminded of the Silicon Valley giants that have graced those same corridors, sat in those same lecture halls, and ate in those same dining halls. Apparently, I was surrounded by the crème de la crème of future billionaires and world influencers. And yet for me, my priorities continued to be squarely focused on the classroom and on the tennis court.

Stanford is famous for producing some of the most well-known tech gurus of our era (see side-note below), but not everyone at Stanford wants to be an entrepreneur, not by any stretch of the imagination. I can attest to that. I never once thought about creating a business myself. While I was there, I only knew one person who wanted to start his own company (and kudos to Andrew, he’s actually gone and done it). Many students were like me, focused on maintaining a high GPA while also enjoying their newfound freedom and making bad life decisions (like unhealthy relationships or illegally downloading movies).

This adds little value to my story, but it’s interesting none the less.

As of Sept. 12th, 2017, adding up the value of 15 well-known public companies founded by Stanford alumni yields a ridiculous $1.39 trillion in value (data from Morningstar):

• Charles Schwab & Company ($53 billion market cap)

• Cisco Systems ($161 billion)

• Dolby Laboratories ($5 billion)

• eBay ($41 billion)

• E*Trade ($11 billion)

• Electronic Arts ($37 billion)

• Google ($651 billion)

• Hewlett-Packard Enterprise ($21 billion)

• HP ($33 billion)

• Intuitive Surgical ($39 billion)

• Netflix ($80 billion)

• Nike ($88 billion)

• NVIDIA ($101 billion)

• Tesla Motors ($61 billion)

• Zillow ($8 billion)

9 others have been acquired, which tack on a cool $42 billion to the total: Instagram, LinkedIn, MIPS Technologies, Odwalla, Orbitz, Silicon Graphics, StubHub, Sun Microsystems, and Yahoo.

In a naive kind of way, I guess I thought that doing well in school just meant getting good grades. I learned plenty of stuff in the process, of course, building up a solid understanding of engineering and math principles, picking up some coding basics (remember Karel?), and learning all about the design thinking process. Through trial and error, I even figured out the in’s and out’s of managing my time and my priorities, although pulling 2 all-nighters a week for an entire quarter probably wasn’t that healthy, in retrospect.

But despite the wealth of knowledge that I picked up in the context of my classes, I didn’t apply that knowledge to anything outside of the classroom, in my day to day life. I simply executed on problem sets, on class projects, on final exam questions. I never adopted the habit of constantly asking questions or searching for better ways of doing stuff.

My 5 years of effort in the classroom weren’t without reward though. Although I left Stanford woefully ignorant of the possibility of an entrepreneurial career, I was equipped with a useful set of grades, experiences, courses, and projects that helped open the door to the Big Tech stage. My time at Stanford had set me up perfectly for the next step in my journey, just a few highway exits away, at a small place called Apple. It was, as I’ve mentioned before, the dream job, at the dream company.

A cog wears few hats

And so down the street I went, to another highly idolized Silicon Valley campus, this one much less like paradise and a lot more like corporate America, with its badged doors, underground parking structures, and lobby receptionists.

With a truly inspiring origin story, maybe one of the most classic Silicon Valley started-in-a-garage-now-we’re-here type entrepreneurship stories out there, you’d think that there would still be some remnants of that entrepreneurial spirit to be found at Apple. But Apple is now a massive company, and down in the trenches, technical skills and engineering prowess are what matter most.

There are definitely many shared qualities that are valuable in both a good entrepreneur and a good Apple engineer, for example: the ability to think quickly on your feet, to operate at a high level even when put under extreme pressure, and to present arguments in a clear and convincing way. Both require an understanding of the nuances of not only communicating and interacting with others, but of navigating complex interpersonal situations as well. So I guess if you look at it that way, my time at Apple helped me develop in a number of ways that should theoretically make me a better entrepreneur (we’ll see soon enough).

However, there is one massive, glaring difference. Whereas an entrepreneur’s goal is to develop and run a functioning business, my goal at Apple was to develop and launch a product (not even the whole product, just a few parts of it). As an iPhone Product Design engineer, I was laser-focused on technology and engineering. Our objective was to make the best possible product within our time and budget constraints. Strange concepts like business models or marketing plans were far outside of our purview. We were encouraged to innovate and to be creative, but only within our limited scope of influence.

To use a simple metaphor, at a large company like Apple, unless you’ve been there for a long time and somehow claw your way up to the higher echelons, you’re essentially a cog in a giant wheel. You own and lead some stuff, and people make you feel like the world will end if you don’t finish your stuff on time. In the larger scope of things, though, your projects are highly defined and well constrained, leaving you with only a limited number of hats in your closet to wear. You learn how to be great at your job, but in the end, your job is still just to be a cog.

Being a cog is not necessarily bad. Each cog is clearly important to the functioning of the machine as a whole, and without the cogs, there is no iPhone in your pocket and no MacBook sitting in front of you. And as I mentioned earlier, my time as a cog in the Apple wheel taught me a number of valuable lessons about product development, communication, teamwork, and leadership that will serve me well for the rest of my life. But for me, personally, I found Apple to be better suited for developing my engineering chops as opposed to inspiring me to be an entrepreneur. I remained, even after all this time spent in Silicon Valley, somehow in the dark on the whole startup entrepreneurship thing.

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It wasn’t until my last year at Apple when I met a new coworker Jason that things finally changed, but it was a shared feeling of frustration and lack of motivation at work that brought us together and motivated us to pursue something beyond our jobs.

But more on that next time! Because this post is already too long, and it’s time for you to get back to work.

Bottom line: I wasn’t born an entrepreneur. For 26 years I followed the path that had been laid out for me. Despite spending 9 years in the Silicon Valley, I never once considered starting my own company. And yet today, I find myself about to embark on my first entrepreneurial journey. So how did I leave the “dark ages” behind and end up here? That’s the subject of Part 2 for next time, so stay tuned (and subscribe so you don’t miss it). 😉

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Thanks to Veronica, Shaan, and Will for editing, and my cat Taro for sometimes sleeping near me while I wrote this. 

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What’s coming up next? 

I’ll be back in a couple weeks to finish out this post by introducing you to 5 key things that have influenced me greatly over the past couple of years, and that have helped push me towards entrepreneurship. I know the end of this post leaves us in kind of a weird time and place, but I promise I’ll bring us back to the entrepreneurial journey in the next post.

Again, if there’s something you want to learn more about, please leave a comment or write me! I’ll give you a quick response or maybe even dedicate an issue to it if I think it’ll be helpful to other readers.

Amazed that you’re still reading, but I appreciate it greatly! 🙏 If you enjoyed this post, please subscribe below if you haven’t already.

🎄 Merry Christmas and Happy Holidays!

That Dude Denis

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Wow! You’ve just finished the second issue of That Dude Denis, a newsletter about a dude who left the Bay Area and moved to Paris. I’ll be sharing my experiences in the most open and transparent way possible as I try to become an entrepreneur for the first time, and also tell you about some important steps in my life that have led me to embarking on this journey. If you haven’t already, please help motivate me to write interesting stuff by subscribing here: