Fleeing the McKinsey trap

Fleeing the McKinsey trap [or insert brand name firm]


Keep personal burn rate low

Take risks when you’re poor

Justin Kan


I have a friend who dreamed of starting something whilst still at university.  Cindy got great grades, killed the do curricular portion of school and started her career at McKinsey.  Who doesn’t take an offer from McKinsey and so her dreams waited. 2 years later, she doesn’t get fired which means she gets sent for Harvard Business School with all expenses paid for.  The catch is afterwards she is bonded for another 2 years.


During business school, she toys with the idea of startups and even does some free work.  She takes part in startup competitions and places third for her idea. At the end of 2 year business school, she contemplates her options.  She really wants to do her own thing but a simple expected return model will show that another 2 years at McKinsey for a 2 year holiday at Harvard is not a bad price – the expected return on her startup is likely 0.  In fact, most would die for her lot in life. Her idea takes a back seat.


Cindy does her 2 years and is promoted to engagement manager.  At this point she’s earning 6 figures, has a great life with soul cycle memberships, organic weekend bruches and lives in the best neighborhood. She weighs up her options.  It doesn’t make economic sense to jump and risk her clear path to partner for some idea which will likely fail. So she stays her path. Extrapolate the years but the decision framework never works out.  [Insert numbers]


There’s many versions to this story whether you’re in big tech, big accounting or chasing whatever you’re told by your circle is important. The message is simple.  Chasing your dream will likely never make economical sense to the good grade high achiever.


It only makes sense for the lowly immigrant with few other options.  It only makes sense if you’re poor and this is your way out. Your back is against the wall and the only way is to succeed.  Failure is not an option. When you look at Silicon Valley’s greatest icons, maybe that’s why the immigrant story is so strong.  Andy Grove, Intel’s famed CEO is the result of Holocaust survivors. If your only option is to succeed, then maybe you will.


“When your army has crossed the border, you should burn your boats and bridges, in order to make it clear to everybody that you have no hankering after home.”
Sun Tzu – Art of War


My grandmother escaped the Japanese invasion from China with what they had on their backs.  With no education and capital, they gathered dried sticks from the hills and walked 10km downtown to sell their wares.  Eventually, her brother got a goldsmith’s apprenticeship and introduced my grandfather to the same shop. Given this was his only skill, he launched his own business and within 30 years sent 9 kids to international universities.  Again, no options forces entrepreneurship and necessity is the mother of invention.


So what if we are fortunate then how do we pay this game?   How do we create an environment where we can force ourselves to jump off the cliff?  I’m with you and never want to get to the point of having to sell sticks. But there’s ready provokes to emulate in our lives to allow ourselves to shoot for the stars.  From what I’ve observed, you need these 4 principles to get to the zen state to jump off the cliff.


  1. Keep your personal burn rate low

As in the cautionary tale, people typically tend to expand their spending to their earnings.  Once you get that bigger TV or soul cycle classes it’s hard to go back. What this means is that when the time to jump comes, their liabilities trap them from being able to jump.  The economics don’t work out.


I spent less than $23,000 last year.  This means I can jump off the cliff and survive for a while before I need to find safety.  It means I have longer runway to try more things and try succeed. It means the economics of startups become less disgusting.  


  1. Cut off the safety net

Say no to the high flying job.  Quit that Goldman Sachs train. When your back is against the wall you’ll fight harder.  Anyway, if you really fail then you probably can get the same job.


After business school I had offers from Amazon, Google, Square and BCG.  BCG had me in golden handcuffs. I said no to 6 figures and instead jumped full time into Xendit.  No other income except the but we paid ourselves to pay rent, eat and exercise.


  1.  Change your measurement

Implicit in Cindy’s tale is a social expectation on success. Good grades, stable job, brand name companies are the mantra of our parents.  Once you’re sipping expensive wine and discussing how to optimize your Starwood preferred status or airline miles, it is hard to flee that social construct.  You have to be willing to get off that rat race ladder and be confident enough to strike out on your own.


During business school, there was a pride to get a Google offer.  There was status to going to BCG. There were bragging rights to join one of the greatest growing companies in the Valley.  But I said fuck it. Anyway, I didn’t really care about their opinions. Turns out we got into YCombinator, the biggest bragging rights for early stage companies.  Accel invested in us, bragging rights from a top tier VC. Within two years, I became Forbes 30 under 30. I wasn’t even the top 40% at BCG. I had to get off other’s metrics to make my own.  It worked out. I’m thankful I was never the best at BCG, else I likely may have never quit.


  1. Take risks whilst the opportunity cost is low

This is when the logical equation is most in favor to do your own thing. When you have nothing to lose you have everything to gain.  When you’re at the bottom, the only way is up. So I find that when people are poor, that’s is the best time to bet the farm.


During my first two years working for BCG, I was paying off my wife’s school debt. We lived on 30-40k that year.  The rest went to loans. Whilst at business school, I racked up 180,000 in debt. We graduated with a net worth far below the homeless person at the local train station. It was the lowest opportunity cost time in our lives.  So it was jump then or never. We jumped.



If you really want to reach the stars, the environment you need to create for the highest chance of success is to:

  • Keep personal burn low
  • Cut the safety net
  • Change your measurement
  • Take risks at the lowest opportunity costs


P.S. Didn’t get the ideal job you wanted that had the most status?  Not top of your class? Great, that may just be the best thing that happened to you.  You can now stop measuring to other people’s scales and create your own.

Proud to be Aussie

Today is Australia Day.  I am lucky to be able to call myself Australian.  The Aussie government asked me to be featured in a publication and I obliged.  Here is the longer version of what got printed.

How did you start? Tell us a little about what made you choose this career path, and where you studied.

I come from a family of entrepreneurs.  My grandfather escaped famines in China to settle in Malaysia, and with no education built a business that managed to send 9 kids to universities overseas.  My father studied in Australia and through fate, managed to build a business in Canberra that changed my family’s fortunes.  At the same time, my mother never let a moment go to waste and despite English being a second language I ended up representing Australia at Model United Nations.

This legacy meant that work ethic was instilled in me pretty early – “we may not be the smartest, but we’ll work harder than anyone else” was the sentiment.  The other important learning from my childhood years was that most things are games that can be hacked: UAI, competitions, hackathons, and school were all things that could be hacked once you understood the rules.

The most fun game for someone who likes to hack and work hard is startups.  I wanted to do something where we get to show up the big guy, show what can be accomplished by a dedicated group of young people. I also generally like doing things that I’m told I can’t do.

Study wise, I studied at Radford College, Canberra then went to UNSW, Sydney.  Radford College gave me opportunities pretty hard to get for most folks and expanded my brain beyond pure academics.  UNSW allowed me to pursue anything I wanted and gave me space to fail and try new things.  Whilst there, I stayed at New College which gave me my best friends to date.

How did your Australian experience (education, training, and upbringing) contribute to your success, and/or your approach to your work?

When I immigrated to Canberra, Australian values were pretty quickly instilled:

1.  I hate authority.  I feel like this is taught in our childhood heroes, from our convict roots to Ned Kelly and the Anzacs at Gallipoli.  My favourite data point here is the one part of Gallipoli that Aussies were in charge of (our retreat) actually had very few casualties, largely due to the unique inventions which made the Turks think we were still in our trenches.  I think this confidence in self results in a great view of the world for startups.  Australians have proven time and time again that a small group with counterintuitive or creative thinking can accomplish something a much bigger resourced group cannot.

2.  Australians have always had to do a lot with a little.  My two favourite examples are that John Flynn came up with a way to cast a “mantle of safety” over Australia to serve the sparsely populated outback with world class medical services.  The pedal radio came out of that effort and RFDS became an example for aeromedical services globally.  My other favourite example is that 100 light horsemen charged Beersheba and took over a city that a whole British army hadn’t in the preceding months.

This legacy of doing a lot with a little makes for good startup mentality too.  To get to our end goal, we have to come up with creative answers in the short term, and think of doing crazy things people with much bigger resources would never touch.

3.  My one gripe is that Australian tertiary education is poorly organised for real work.  UNSW gave me space to go on exchange, so I went twice.  What I quickly learnt was how much more practical the American tertiary educational experience was.  They focus very quickly on useful skills and provide the space to create startups quickly.

Australians also suffer from tall poppy syndrome.  Failure isn’t celebrated or forgiven (e.g. bankruptcy laws vs America’s) so it’s harder for us to build startups in Australia.   The flip side is that those of us who do do startups care even less about others’ opinions – a very valuable trait in startup land.  Finally, Australia is a small market, so (like Israel) startups have to think globally from day 1.

What made you take the leap overseas and why Indonesia?

Primarily adventure, but split into personal and business reasons.  Personally, my family is from this region, Southeast Asia is Australia’s backyard and I love the food/travel here.  Finally, not all Australians are willing to work overseas in a developing market where everything is difficult.  My personality is to be roughly happy wherever, so I’m designed to enjoy life on the less trodden path.

From a business perspective, as much as I love Australia, the market is too small to build a billion dollar idea.  Southeast Asia presents some of the most exciting opportunities – large, young and tech savvy population that’s undervalued and underserved.  This context is a fertile ground to build something new and big.

What were the biggest hurdles in building your business and how did you overcome them?

First problem I had to overcome was rewiring my brain.  Until I studied at Berkeley, billion dollar valuations were something you never heard of in Australia.  I remember I was discussing my ideas with a venture capitalist who ended up becoming a mentor.  He stopped me about 7 minutes in and said “If your idea isn’t worth a billion dollars, don’t talk to me about it”.  This paradigm shift was humbling and inspiring.  Firstly, it was a reprimand that I was wasting both our times with ideas that were less than that.  Secondly, I took it as a huge compliment that he expected that I could come up and execute on billion dollar ideas.  Two years in America rewired my brain so that I had the right attitude on startups.

Next is how do you learn to build a company that can grow 30% every month for more than 2 years?  We were lucky to make it into YCombinator, the world’s best accelerator that produced companies like Airbnb, Twitch, Reddit and Dropbox.  Through that process we got mentors who had made billion dollar businesses, received advice from successful entrepreneurs and backing from some of Silicon Valley’s best.  This was quite the foundation to build a startup.

Thirdly, we needed to understand the Indonesian market and context.  There’s no other way than moving and soaking in the culture.  We didn’t look to change it or judge it – we had to adapt to the local context.  Everything from hiring, inspiring, selling and doing deals changes from Silicon Valley to Jakarta.  We’ve relied heavily on hiring great people and surrounding ourselves with advisors who can help us navigate.

What do you think is the single most influential factor in your business success?

Work ethic – but not in the normal way. I believe success is roughly some function of luck, work ethic and smarts, i.e. success = f(luck, work ethic, smarts).  I have nearly 0 control over luck, except that working harder gives me more rolls of the dice.  Smarts can only improve to some asymptote already given to me before I was born.  But work ethic I have complete control over.  So I optimise for doing the best I can and measuring against that.

Whether I succeed or fail is not entirely in my control nor will it define my happiness.  So I focus on working hard and doing things I’m passionate about.  In other words “Do something so valuable that even if you fail, the world is better off for you having tried.”  If I’ve done the best I can, then I give myself an A no matter the result.

Is there something particular about the Australian character/culture that drives people to search out international experiences and to compete for success in other countries?

Yes, a few things come to mind.  Australia is small and we’re off by ourselves in our corner of the world.  This builds a curiosity that means we must venture off our island in search of the new.  This is our version of the British getting off the island and building a competent navy that explored the world.  For those of us who want to build something really big, then we also have to get off the island and find markets big enough for our ambitions.

Second, we’re extremely adaptable.  We have this confidence that things will work out and that we’ll be ok and shine in the worst of circumstances.  Our history is full of these proud moments and I think the legacy stays.  This means we’re well suited to going beyond the obvious routes and can plant our roots in a locale far from home.

Third, Australia is a story of underdogs.  We always cheer for them and praise their stories – Eric the Eel is a vivid memory from the 2000 Olympics.  Whether cheer or jest (or some combination of the two), we have this spirit to laugh at ourselves, yet really gun for the underdog to succeed.  This underdog quality is etched deep in my bones and means that I care little about the odds, I’ll still have a go.

Finally, we’re a bunch of immigrants.  We come from other places so there’s no fear to then travel somewhere else.  For those of us who’ve adopted Australian values, we get to demonstrate their goodness throughout the globe – and people generally love us for it.

What’s one of your most favourite things about living and working in Indonesia?

In a world of wonderful growth, there are unlimited possibilities.  Nothing is quite set in stone and everything is in flux, whether the traffic lanes or the regulations.  This beautiful state of flux means that there are great opportunities to design a new world and as a young person define the future of our industries.  This is a once in a lifetime opportunity and one I couldn’t miss.  We’re proving the statement “Never underestimate the ability of a small group of dedicated people to change the world.  Indeed, it is the only thing that ever has” (Margaret Mead).

Have you been inspired by the achievements of any particular expat Australians living and working overseas?

These guys don’t know it but the founders of Atlassian were the same degree, scholarship at UNSW and only a few years ahead of me.  I saw them grow from a name only known amongst a few friends to being a darling of the tech world.  That kind of tenacity and success from similar roots set an inspiring example of what someone in my position can achieve.

What do you know today that you wished you had known when you first started?

At the macro level, there are few things my current self can teach my earlier self. I’m a believer that once I’ve decided something, I don’t look back and I charge.  If I’m wrong, I run at full speed into the wall, pivot and run again.  I measure myself on internal metrics, so if given the same information, I would have made the same choice that was true to self; the result I’ll deal with as it comes.  Nearly nothing is irreversible in startup land.

At a micro level, I would like to know all the mistakes I was going to make so I could have avoided them.  Hindsight is 20/20, so I’d happily avoid the small mistakes I could have.  Hiring is really difficult and people in interviews are vastly different than people next to you in the trenches every day.  We now force everyone to spend at least 1 day working with us before we hire them.  It’s a self filtering mechanism and keeps the bar high.  It means we lose a lot through our hiring process but higher quality > numbers of people.

What makes you proud to be Australian?

We always bat above our weight category.  Whether international politics, gold medal count and founders with successful startups, Australia always outshines on a per capita basis.  Pound for pound, we outperform so many other countries across a range of disciplines and this makes me extremely proud.  I get to claim this legacy and hopefully extend its reach.

We’re sensible.  I know internally that we complain a lot, but we’re a pretty sensible lot when compared to what’s happening overseas.  When I read Australian news I find it flattering that we complain about relatively menial issues.  One day I was reading about how someone said something nasty about someone else in parliament, all the while in America, they were dealing with yet another mass shooting.  We’re structured to care about each other with healthcare, we have some of the world’s best beaches, most people have the ability to live a good life and even as an immigrant, my adopted home adopted me far before I adopted it.

We’re genuinely kind.  We may tell you about dropbears, laugh our heads off at your expense, swear more than a sailor, but when we ask “how are you?” we actually want to know.  We have far more capacity to think about others more than ourselves (sometimes to our detriment) and are far more giving than many other cultures.

Ultimately, every country I’ve visited (30+) whenever I mention I’m Australian I’m greeted with welcoming smiles and tales of other Australians that have passed through.  In Europe, we’re drunkards but the life of the party.  In America, we’re the country with strange animals, the Crocodile hunter and an uncanny ability to excel in our fields.  In Asia, we’re a great source of income and almost too cheerful in our giving.  All in all, these moments are the ones that codify how awesome it is to still call Australia home.


Daily checkins

I want to set the context for daily checkins and how to use them.  We’ve found these are the most effective ways to pass on the way we work and also ramp you up fastest in a very personal way.  


Daily checkins are the building blocks of coaching up our team and as time goes on becomes a great way to understand blockers and remove them.  It’s a great way to make sure you’re moving as fast as possible and iterating quickly.  Overall, we’ve found that it increases employee engagement and connects employees/managers on a very short feedback loop.  At nirvana level, it becomes a way for you to take control of your goals and get us to remove blockers and give you resources so you can excel.  


We are pushing towards more and more measurable targets so it’s clear for everyone.  This isn’t quite clean given we’re a startup and things change all the time.  However, we are wanting to set clear outcomes so you know what it means to be doing well.  

The first few chats, I likely won’t dictate KPIs yet.  It’s for me to understand what you’re up to and how you’re going.  After a while, I do want to push towards some measurable outcomes.  These goal posts may shift but it’s better than none.  These outcomes will then be formally measured as part of your performance assessments.  


When we first begin, I’ll likely ask questions about what you’re working on and how you’re doing it. I’ll quickly start to push the logic and push you for next steps.  I’ve been told I’m quite Socratic in my methods.  

Ultimately, this is your meeting.  The expected format is that you come in with your live tasks, status updates and direct questions/decisions for me.  We just work through your list of things and it’s up to you to prioritise what to spend the time on.  My nirvana is when you’ve done all the prework so I can easily say yes”.  

What I expect

  • You have an agenda for what we need to cover
  • You maintain a clear to-do list that we can walk through
  • You come prepared with status updates and questions
  • You do the work so I can just say yes”

What you should expect from me

  • Be engaged in what you have to say
  • Ask questions (hopefully intelligent)
  • Push you to achieve more faster
  • Remove blockers that you’re facing

Tips for new employees

This is a mix of part expectations and tips for what success looks like when you first start

What we’ll look for

1. Acquire one customer

Everyone on the business team is expected to sell to customers.  We’ve found a correlation between those who convert a customer in their first month and success at our organisation.  I suspect it demonstrates that you understand our product and have worked hard enough to convince someone else to use us.  This spells goodness for us.

2. Pick up hard skills quickly

There’s a basic set of skills required to be at Xendit, including Powerpoint, Excel, Postman.  The faster you learn how to use this the way we expect, the better you’ll perform.  We’re sticklers for Powerpoint and Excel because we’re ex management consulting and private equity.  Postman you’ll need so you can use our APIs.

3.  Earn trust by owning things

We want to see you say yes” and volunteer to get shit done.  We want you to become an owner on the things we give you, and not rest until they get accomplished.  You’ll get basic points by doing what we ask you on time.  We’ll be pleasantly surprised if you can put your hand up for more things and get it done.  Can be small things like doing some analysis or coming up with a strategy.  

Practical tips

Bring a notebook and write stuff down I don’t know why anyone would show up to a meeting without paper and pen.  One smart ass once told me they could remember everything to do.  That was disproven in about 30 minutes.  Writing helps you remember an order of magnitude better and gives you quick recall on context and to dos.  

Keep your own to do list We aren’t strict on a system yet but we do expect you to keep some sort of to-do list.  Many people use Trello, Todoist or paper and pen.  If you don’t have it recorded there’s little chance of you accomplishing it.  This is also in our basic test of trust to execute.’  

Write down what you want to say for those who struggle with summarising or presenting, you will do much better by writing down what you want to say, before saying it.  Most excellent leaders write down what they want to say before saying it, e.g. Obama and Martin Luther King.  If these orators need to write, you probably should too

Ask for feedback we’re often so focused on the work we don’t think about feedback until an 1-on-1.  We find our best performers tend to ask an outsized number of questions to solicit feedback and then execute on them.  When you get feedback, pick 1 thing to work on and just try it on for 2 weeks.  If it doesn’t work, iterate and try something else.  I tend to think most humans can’t focus on improving more than one thing at a time.  

Work hard we put an outsized amount on emphasis on working hard.  We want people who are willing to fight with us in the trenches and beat the competition.  That has historically been partly driven by working harder than the competition.  

Be willing to do anything we really hate it when people think they are above some task.  I have a standard that I won’t ask someone to do something I’m not willing to do myself.  To date, I think everything I’ve asked I’ve done before in some form.  Point being, to be a leader you have to be willing to do anything.  Those who aren’t don’t really belong here.

Status, Blockers, Next Steps this is how we do status updates.  It’s a simple and effective structure.  If you come to me without this, I’ll force this structure.  It’s an easy way to meet that structured communications dimension in performance assessment.  

Learning philosophy Xendit is probably one of the best way to grow quickly.  Whether we’re up or down, we have the opportunity to do things you can’t do in any other job, e.g. grow a business 30% month on month.  Therefore, I think your goals should be to learn as much as you can.  We’ll teach you until you stop being self driven about your growth, then we’ll likely put attention to someone else who is progressing and growing. If you decide that you’ve had enough and don’t want to grow our way, you may still be good at your job.  But you’ll find you won’t be promoted or get more responsibility, and in fact your responsibility may be diminished over time.  

A day’s thoughts to internalise

1.  Talk to the right person

We studied a case where the protagonist spoke to the “Internal head for magazine development” and got politely told to disappear.  4 months later the protagonist speaks wi the Editor-in-chief and leaves with a term sheet.  Moral of the story: make sure you speak to the right person who has the power and whose interest is aligned.  The internal head probably wants to do it themselves and doesn’t want you to do their job for them.  The editor-in-chief wants the best magazines.


2. If someone is willing to give me money, it is NOT necessarily a good idea

In this frothy venture environment, you really only want to be accepting money from experienced investors who can really get you some place.  There’s no point receiving money from someone with no experience to get you to where you need to go.


3. Don’t haggle over the terms, focus on people

When VCs/entrepreneurs haggle too much, there’s a sense of mistrust which seeps into the relationship.  This sets up for a bad relationship, the VC doesn’t work hard for you, their network isn’t tapped.  You don’t get the marquee Board, advisors or customers and the likelihood of your failing stays at 99%.  When you search for investors, search for someone you’re willing to be married to for a while.  Focus on the people on the other side of the table, not the money.


This time of life is all about learning.  Three thoughts:

1. Incorporate early

Start-ups don’t seem to nearly incorporate themselves early enough.  After hearing two lawyers speak on campus there is one clear takeaway – incorporate as soon as possible.  Get those shares out at 0.0000001 per share and figure out the basics.  It’s hard to try say a company is worth nothing the day before a Term Sheet is signed.


2. How to read people’s minds

I heard a great piece of advice from a VC Partner.  There are two things that he has always used to read people’s minds:

– Understand their incentives
– Learn to read body language

The combination of the two throughout a conversation will quickly highlight what someone is truly thinking.  A fascinating piece of wisdom.


3.  Don’t over optimise with a short-term view

We studied a case this week where someone over optimised a single point in time and screwed the other guy.  Turns out this came back to bite the guy in the ass as he disenfranchised others within his company and ruined his reputation.  He is now stuck at a mediocre company with no-one wanting to work with him.


I love all things sartorial.  At the same time, I have a desire for practicality and presentability that limits my forays into the fashion wild.  I also think the art of being a gentleman should not be lost, but that’s a separate matter.

In any case, the logical extension of makemysuit was a foray into the accessories that make men, men!  So became skinnytie, a first push into the world of classic accessories via ties that I would want to wear at a price I would want to pay.

These ties may not be the wildest ties you’ll ever wear but they’ll be perfect for standing out at work whilst staying within the bounds of presentability.  One of my favourite ties below…


2 inch navy blue tie


The holiday season is my favourite time of year.  I have a romanticised version in my head that the best of humanity comes out during this season: Sinatra over the sound waves, ‘Hi’s from strangers and friends, and generousity seen only during one month of the year.   Unfortunately, I’ve also seen some gnarly pictures of stampedes (Black Friday is at work), but my mind chooses remember the romance of the season.

I am thankful for three things:

1. Time

I’ve been blessed with the easy things in life, and now have the time to explore.  In the meta sense, I get to explore how I can play a part in disrupting the world for good; in the micro sense, the Thanksgiving break gives me time away from the MBA to think, relax and read.  With this time I read “David and Goliath” by Malcolm Gladwell.  He outlines amazingly how the underdogs come to win in many situations by overcoming their disadvantages, playing to their strengths and capitalizing on the weakness of those who should have won.

2. People

I get to meet amazing people every day.  I wake up to an amazing person every morning, go to school with a diverse group of experiences, learn from world class experts and listen to the most successful people in practice.

3. A natural curiousity

As I was reading David and Goliath, I reflected one of my favourite childhood books called “A 100 fantastic facts”.  I decided when I was young to commit these to memory and though I now have no recollection of what’s in there, I remember each fact sparking a research process that allowed me to chase my curiousity.   I then reflected on some of my internet searches this weekend: dyslexia, Rose Bryne, hobbies for a 14 yr old (my brother in law), Huguenots, Automatic millionaire, Logitech G5 mouse, Star Wars Millenium Falcon lego price, makani power, bodega bay and grandview house prices.  A huge spread of interests which I love to keep pursuing.

It means I get to discover a lot of things: Dyslexia is widespread amongst entrepreneurs and innovators (I have it too!); Rose Bryne is Aussie – which means I can be proud!; the Huguenots are pacifists though they have an amazing history for standing up to stupidity – the Nazis for one; my favourite Logitech G5 mouse is getting more and more expensive – just like my Star Wars lego collection; makani power has an amazing invention for harnessing wind energy and one day I’d like to own a house in America.