An introduction


I have straddled major cultures, spanned diverse demographics, and developed deep expertise. Here are some things I’ve picked up along the way.

I have had the great fortune of not having much handed to me, which made me appreciative for anything I did get. My immigrant family was tenacious, working class, and prided on our independence. Through luck and perseverance, I ended up at a prestigious boarding school and Ivy League university with a degree in Engineering.

But instead of becoming an engineer, I became a trader – starting at the very bottom of the hierarchy in the Eurodollar pits of the Chicago Mercantile Exchange.

Trading (essentially taking calculated risk) taught me an ethos of living, which I am eternally grateful for. Trading successfully through the Barings Scandal, Asian Monetary Crisis, the Dot-Com collapse, SARS, and the Global Financial Crisis gave me a firsthand view of the very limits of human fear and greed. Through trading, my existing paradigms were shattered and rebuilt repeatedly, and I learnt which human truths actually persevere. This is one key form of innovation.

My experience allowed me to pivot in 2006 (the end of my open outcry career as the Singapore trading pits closed and went fully “electronic”) to founding a small proprietary trading company called Grasshopper. I knew next to nothing about electronic trading; but I deemed it a worthy risk and I was willing to learn.

Now, I look back and marvel. Eventually “me” became “we” and my team grew (Grasshopper now employs over 60 people).  We built our whole trading platform independently, trained our talent internally, and never had any customers or outside funding for the last 16 years. Trillions of dollars go through our books, carried by digital packets in millionths of a second to exchanges around the world. We serve the markets, but also spar with the best trading firms in the world.

My days in the trading trenches are long over; but I relish, as much as ever, the pursuit of value. And when I say this, I mean value in its truest and broadest sense. I invest most of my time now in people and platforms vis a vis what I think will be the most tumultuous and technologically disruptive decade in history.

I sometimes wonder if that 11 year old, riding his bike across town to caddy at the country club, could ever have imagined that ride would take me to where I am now.

Here are some uncommon pieces of advice I’ve picked up over the years distilled on a single page just for you. I hope it provides some value to your journey!

Career Advice – For when you’re just starting out

Biggest takeaway from your first job?

My very first job was a golf caddy.  As a “fresh-off-the-boat” pre-teen, that was an eye opener and i realized that life goes far beyond one’s boundaries.

My first professional job as a clerk at the CME at age 21 taught me to be stoic.  While there were many friendly and helpful people on the trading floor, there is also an overwhelming sense that you must be competent and calm when absolute craziness erupts.  My adage during those difficult but exciting years was “wherever you go, there you are”. Just deal with it.

Would you still recommend trading as a career for someone just starting out?

Trading as a life skill is an amazing teacher that forces a tenuous balance between ambition and satisfaction, confidence and humility, aggressiveness and passivity.  But the edge of the old days is long eroded by technological speed and digital gamesmanship.

To be a trader now you have to either opt for a time frame that is free of the technological fray (for example, avoid time frames when your human reaction time could be a factor) OR you need to be comfortable with code, handling datasets, and market micro-structure.  I do not think there is much of a middle ground anymore…. Today, one has to be a technologist as well as a trader.

On the bright side, that is a potent combination!

People change jobs and careers a lot more these days. What are your thoughts on that?

People change jobs more because the world is changing faster.  Let me be clear I am not addressing chronic job hoppers here! For the ambitious and competent, once a role’s capacity is saturated, you must not fear pivoting.  Remove your fears, understand the situation fully, then act… without emotion.

What’s something a fresh grad should put up with in their first job? What’s something they shouldn’t?

I suggest that you have some tolerance for inertia. The larger the organization, the harder it is to overcome its inertia. It takes time for things to get moving, and recognizing this as a new and energetic employee is a sign of maturity. 

On the other hand, if your organization consistently demonstrates no appetite to overcome their inertia… get the hell out of there.

Career Advice – Management

What were your ambitions for Grasshopper? How did you decide how to grow it?

Grasshopper shaped me as much as I shaped Grasshopper.  I was not born a leader; rather I used to be a very reluctant leader.

My ambitions were simply to get to our potential, whatever that may be. I don’t like shallow metrics like ROI or share price; and I have never run Grasshopper that way. I think it’s important to have a much grander vision.

Be good to your people, pay it forwards, and demonstrate high standards. In trading everything is a transaction, but in life not everything is transactional. Manifesting these notions were my main goal. When you stop thinking about an end and start thinking about the process, it changes the whole paradigm.

Perhaps to my detriment, I rarely think about exits but I do think about smart pivots all the time.

How is Grasshopper organised internally?

We have a flat and loose hierarchy but are now evolving to a complexity leadership model with decentralized autonomy and power.

However, a good tech company also has to employ agile techniques to push forward and execute, and a good creative company has to embed design thinking in what they do to innovate.

I think a great company in 2020 has to have this holy trinity (complexity leadership, agile and design thinking) to really be robust.

What were some major growing pains, and how did you overcome them?

“I was once out strolling one very hot summer’s day
When I thought I’d lay myself down to rest
In a big field of tall grass
I laid there in the sun and felt it caressing my face
As I fell asleep and dreamed
I dreamed I was in a Hollywood movie
And that I was the star of the movie
This really blew my mind
The fact that me an overfed longhaired leaping gnome
Should be the star of a Hollywood movie…”

Lyrics from Spill the Wine, WAR

Here is a secret.  No one really knows what they are doing.  So just keep trying. Challenges will come no matter what.

Culture is such a key ingredient to any company. What’s Grasshopper’s culture like, and how did you nurture it?

I realized long ago that culture was king. What did we do? We copied and adopted from companies, teams, and people we admired. We also wrote a company handbook, called the Little Green Book.

Career Advice – Entrepreneurship

It must’ve been hard starting out when nobody knew who you guys were. How did you overcome that?

There’s no magic spell. It’s just persistence and thick skin.

How important were relationships in the industry, and what did you do to grow them?

I spent a whole career insulated from the old boy network of finance. We never had any customers and we were “buy side” so… I escaped the need to hob-nob. This is ultimately a disadvantage, but also a great luxury because we have full independence.

I approach relationships the same way regardless of industry or benefit. Act with competence, generosity and authenticity. Your reputation will follow and things will flow from there.

How did you find and convince people to work for you, when nobody knew who you were?

See above.

At the beginning, when money was tight, where did you scrimp and where did you splurge?

In our early offices, we had no air conditioning after 6pm –  that was a big problem in Singapore where we were trading until 4-5am! We literally had no remedy for this until moving to a new office with auxiliary aircon.

We splurge on quality with a critical payoff. Well designed office chairs, top notch servers, fun company offsites, and anything to do with improving our employees.

Trading as an industry…

How is trading now different from when you first started Grasshopper?

Trading is now largely void of human intervention.  There is human intent, but that intent is 95% executed by machine.

Where do you see trading headed in the next 5 years?

Exchanges are going to become dependent on wholesaling of flow (orders to buy and sell).  Less and less action will ever hit bids or lift offers on a traditional “lit” exchange. They will be forced into a tight corner from decentralized exchanges, dark pools, synthetic contracts (eg off-exchange, crypto-based), and shifting millennial mindsets on investing.

However, there is a fundamental human need to predict, protect, and participate, so some form of trading will always be thriving.  It will never, ever be like it once was.

What principles have remained the same?

Fear and Greed remain the harbingers of a downfall.

What principles have become irrelevant?

Great question.  I used to like the old adage “If there is a panic, panic first… or last”. 

I think this phrase has lost a lot of relevance in modern high-frequency/algo trading. There is too much sub-millisecond gamesmanship to think this way anymore.

You trade crypto… Where do you see Bitcoin (or other cryptos) in our future?

I see it as an alternative currency within a generation and a pillar for the new economy. Our current economic model is outmoded. Digital assets are but one incursion of a technological tsunami that is coming. I hope we harness it smartly.

Life Advice

You’re an avid sportsman. How has sports affected your life?

Practice. Discipline. Culture. Teamwork. Culpability. The list can go on and on.

What kind of people do you respect the most?

Competent but humble people with a high degree of empathy and ability to communicate concisely are a great start. 

If such people can also dream of and execute a grand vision… well, you are in the top 1% of all humanity.

How has having kids changed your perspective on life?

Kids are a blank slate.  Because of that, one must check all assumptions at the door!  That makes you a better leader (hopefully) and requires a regular checking and (re)defining of mutual goals.

Nothing enhances and screws up one’s life like kids.  I am ever thankful for my 5 kids.

You’re a very casual dresser and an avid junk collector. If you had to choose between wearing suits for the rest of your life, or getting rid of your junk collection, which would you choose? Why?

I’ll get rid of the junk. I love my junk (“I buy junk, but I sell antiques”) but.. They are just things and I can do without them.

Meanwhile wearing a suit, sans legitimate reason for formality, strikes me as rather foolish. I don’t like spending my time being that kind of foolish!

Music is a huge part of your life. Why does it mean so much to you?

1970s New Jersey was not really the melting pot it is today. During those first few years of assimilation in America (I spoke only Chinese until 5 years old), music was both a place of solace and a universe of discovery. Every summer my (much) older brothers would bring back the best of rock and roll, electronic, funk, disco. I loved listening to those old vinyl albums.

Music, in high school and university, provided not just entertainment, but a profound glimpse into human psychology and its ironies. I did not understand why Elvis was cool, but Chuck Berry was dangerous. Or why early underground disco was revolutionary, but pop-music disco sucked so badly. The first breakdancer I met was in 1982 and I had never, ever heard anything so darn mesmerizing before that cut of Jam on It by Newcleus which he played. I followed the Grateful Dead across the USA and saw the strength of dead-head culture survive generations. 

Music was culture to me. And culture, as a reflection of people fascinated me. Banjo bluegrass? Dancehall? Punk? Ska? Rock? Jazz? Motown? Hip-hop? I love all the funky authentic stuff and abhor the saccharine crap that’s pumped out to the masses. Understand a style of music, and you understand a facet of humanity. It’s as simple as that.

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Hi, I'm John Lin. Sometimes I succeed; sometimes I fail. But I always try.

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