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.  

Why you should (not) join Xendit

We’re always on the recruiting bandwagon and I’m a big believer people should know what they’re getting themselves into before they jump on the bandwagon. Taking a page from a previous professor’s book, if we bare all and they still want to join, then they’re likely going to be the best. His was more perverse – he discouraged everyone to become an entrepreneur – I suspect the ones who still do just might have enough intrinsic motivation to make it.

There’s lot of great reasons to join us. We’re growing fast, we are a team of underdogs and it’s us against the world. You will accomplish more here than likely anywhere else and you can take on as much responsibility as you can handle. This part goes on and on and if you pass our case interviews you’ll see the sell.

I want to focus on why you shouldn’t. I say these in all our interviews but it’s easy enough to post here too.

1. We’re direct

For Indonesians, we’re direct.  For Americans we’re indirect.  One of our cultural phenomenon is that we’re super tight.  We live, work, play and eat together so it’s a little like family.  This tightness is actually very different from other startups and a great benefit for the way we work.  It does mean we’re very open and less willing to take shit or ignore shortcomings from people.  We also move too fast to beat around the bush.  This means we’re very direct: with instructions, feedback, comments, written words.  So if easily offended, try something else.  If American, then we’re super nice 🙂

2. We work harder than anyone else we know

Like actually.  We work nights, weekends and whatever we need to to get the job done.  We’re results and customer driven.  If our customer needs something and you’re on holiday – you still get to reply.  If it’s 10pm on Sunday, you get to reply.  We know we’re not as well pedigreed as other companies, not as Indonesian as Indonesians and not as Silicon Valley as Silicon Valley.  This is the one input we do control and so we work it hard.  Not Chinese Chinese/Japan/Korean hard, but Chinese American hard.

3. Trust is super important

We rely heavily on trust.  When you come in, we trust immediately.  We’ll be super optimistic else we wouldn’t have hired you. We’ll give you the keys to the safe, we’ll pile your plate up till you say “I can’t handle it” or you perform poorly.  You’ll get as much responsibility as you want as long as you’re performing.  This is super cool for most because you’ll do more interesting stuff than most people your age, (this includes the girl who was 7 years in PE before us).

However, the flipside of this trust equation is that once it’s lost, it’s really hard to gain back.  In fact, most people who reach this point end up leaving.  It’s just too hard to perform well over a period of time to impress us and get back on the horse.  This means we’re not a 3 strikes out kind of place.  We’re a perform your best all the time kind of place.

Accidentally ending up with a Mustang

A weird decision

When I arrived at the rental car service, they asked me if I wanted something fun or something fuel efficient.  For some subpar reason (jet lag, temporarily low ego and a wanderlust for something cool), I opted for the “fun”.
Rarely, do I ever make such uncalculated decisions, so much so when skipping my wife she didn’t believe me, her mum or brother that I had rented a 2017 Mustang.  It took her brother going outside with a camera to make her believe*.
Her first question “Do you feel like a tool driving that car?”

3 things I’ve noticed since being in a Mustang

  1. People give way when they don’t need to
    This may be confirmation bias but I was in several situations where someone else had equal or slightly more right of way, but they let me go.  First, I was in a carpark where I was merging onto the main thoroughfare.  I stopped to let a driver pass by on the main road.  He instead stopped and signaled for me to go.  An hour later I was in the carpark of Best Buy, I had a stop sign and a lady on my right had none.  I stopped.  She stopped and signalled for me to go.  I signalled for her to go.  She insisted I went.  Finally, some lady was being a bit retarded and I beeped her preemptively to avoid the rental getting touched.  She said sorry, which is the first time anyone has said sorry.This could be attributed to coincidence but reflects a different experiment where people gave in to richer cars like BMWs when they didn’t have to.  Also, fun fact BMW drivers are jerks.  Incidentally, I’m not purposely less willing to give way to a BMW because of this research.
  2. I don’t appreciate it
    I’m not a car geek.  I consciously made a decision not to be.  About 13, I was choosing between cars and computers.  Most of my friends went to cars but I went to computers.  1) cheaper depreciation activity  2) I could actually make money and so I made a bunch of computers for my friends and maintained others as my first side income.So I’ve noticed I don’t know how to “feel” the horsepower from behind the wheel.  I wouldn’t know what constitutes a ‘good ride’ so I can’t fully appreciate whatever awesomeness I’m meant to be feeling.
  3. I’m more stressed using it
    When I was a kid, my mother never let me run near glass without a good chiding or yelling.  I think that data point represents an innate fear instilled – I have an irrational fear being around rich things.  It turns out this extends to the car.I drive even more like a grandma around it, am way more cautious and generally scared of it getting touched.  Such luck as I’ve never had a car roadside issue and today I have a flat tire from a screw on the side of the road.

*As more context, all the other vehicles I’ve owned.  TL;DR – a bunch of otherwise very average rides because I’m cheap.
  • Hyundai Excel 1991 (Manual) – roof leaked water, no zircon and everything was cracked or worse for wear.  When I tried to sell it, I didn’t get one bite and the shop wanted me to PAY to take it away.  I ended up giving it to a friend of mine
  • Suzuki GSX-250F Across – motorbike that was way to heavy for my small frame and wiggled violently in the wind.  Otherwise a lovely ride
  • Acura TL 2001 – my first ‘luxury’ car with automatic windows, air conditioning and a working radio.  Bought it for $3,500 from the original owners and that car so plenty of action.  The radio even worked.

Neophyte leadership

As our team as quadripled this year, my role is starting to change. I’m starting to replace “doing” with reviewing and managing. Given the YC mantra to focus on building a great product I feel angst when not directly working on product. I’m on a bullet train in between two South East Asian cities. It’s a rare moment to reflect on what has been thus far in a growing leadership role.

1. 1 on 1s are powerful

BCG taught me to institute process. I am naturally averse to adding process but I’ve found that honest 1 on 1s allow me to manage my people better than any other technique. It allows me to truly hear their dreams, issues and what I can do make it better.

More good suggestions have come from here than any other forum. For example, our current set of publicised metrics are the result of someone’s feedback. Feedback has also helped warned about someone’s unhappiness which allowed me to prevent churn. As we continue to grow, 1 on 1s remain my favourite process activity.

2. Coaching as a method

I’m a wartime CEO. I thrive under pressure, when things hit the fan and I love making calls when things are crazy. However, wartimes require fast decisions from the top executed well – which is a poor method for developing your team for initiative.

I took some coaching classes at Berkeley and underwant some professional coaching myself. I’m now convinced that for me, the 1 on 1 style of gaining rapport, leading by example and coaching through feedback in the first 30 days yields the best results.

3. Hire for long term, fire fast

The hires that have been the best are closely correlated to the ones which we interviewed and closed within a week. The worst performers are the ones we’ve made when we’ve been desperate and an applicant has just been below standard. “He is good but…”

I’m now convinced that even when we’re desperate we have to be patient for the right person. Chemistry has to click straight away. For us that means intelligence, work ethic and ownership mentality. Cultural chemistry normally means an underdog with the humility to learn and the willingness to work harder than all their friends.

4. I have become more impatient

I’ve noticed that my willingness and ability to tolerate bullshit has dropped.  The subconscious frame is that I want to leverage my time well.  If someone comes up with a well thought out problem, proposed solutions with a recommended one based on logic, then time spent with that person has high leverage. I can make an informed decision and trust the assumptions on which it is based.  However, when someone hasn’t done the work to go the extra mile, time spent with them is a wasted hours I’ll never get back.

If someone’s slides don’t meet expectations, they’ll need to humble themselves for review by someone who is good. If people haven’t thought through a problem, then I don’t really have time to think through it for them. I now realise why some of my managers were pissed off – there was a tonne of pressure to perform and people who hadn’t put in the extra mile were more negative than useful for the cost of switching context to talk to them.

It does mean I can recognise performance easily.  It’s easy for me to assess what someone’s strengths and weaknesses are.  In an impatient world, you clearly can see how someone can outperform.  When I ask someone in passing to register a website, they quickly come back with options that I need to care about and then a few days later it’s done and connected to the existing one in the right way. That’s a good leverage on my time.


How to onboard your users successfully

(Summary of book “Intercom on Onboarding”)

“We’ve discovered the only proper way to onboard people is to understand where they are, what capabilities they have, where they want to get to, and then use a combination of interface, communication, tooltips, nudges, and messages to ensure they’re never stuck on the path to achieving their outcome. That’s what successful onboarding looks like – unifying a successful business outcome and a successful customer one.”  Des Traynor, Cofounder, Intercom

Start with a story

The first task is to understand your user’s journey to success.  This journey is rich in emotions and stories that will expose what your customers truly care about, what help you can provide and when you can help them.

Likely, you need to talk to those who have just become highly engaged users, e.g. when they’ve started paying or some other equivalent metric for your business.

In executing these interviews, you’ll want to accomplish the following:

  • Understand their motivations and frustrations before they chose you. This gives you a basis for your future marketing content and channels.
  • Understand their definition of “success” with your product. This is the magic moment when they realise your purpose and value
  • Recount the steps from decision to use you until the point of success, e.g. signup to first email campaign created
  • Be specific in your questions to draw out emotions and specific actionable information “Which part was hardest?” vs “Was it easy?”
  • Who else did they need to adopt successfully, e.g. budget holders. You’ll want to be able to empower tech people with data to convince the budget holders.  Or you may need materials to help a business person convince dev teams an integration is easy

Here’s an example email to use to solicit time from your users

Hello [name],

My name is Moses and I’m trying to make our setup process better. I’d love your personal take on it.

Could we schedule a 20-30 min chat in the next couple of days?



Actionable takeaways:

  • Conduct in-depth interviews with all fully integrated users
  • Make credible PDFs to allow folks to fight your case, e.g. tech team to bring to budget holders

Design an onboarding path

Based on your starting points and “success” endpoints, create an onboarding experience that makes sense to a user trying to complete a “job”:

  1. Free trial is your opportunity to sell
  2. Before they’re signed up:
    • Webinars, 1:1s, Docs, How to videos, Best practice blog posts,
    • Get customers to tell their stories of success with Intercom,
  3. After they’re signed up:
    • Build data driven onboarding messaging schedule
    • Trigger updates for pro users who aren’t using all the features
    • Every customer support ticket should have two tags 1) product area and 2) type of convo, e.g. confusion, bug, feature request


1. Doing a trial

Successful trial should have people going up to the right.  People that are going to churn have a very predictable path downwards.  The danger zone is before they’ve failed and realize you’ve charged them.  That’s too late, you got to get them in the middle.

Trial usage graph

(originally from www.intercom.com)

To achieve a successful trial:

  • Understand “success” outcomes
  • Ensure you have targeted docs, tutorials and case studies to help them succeed
  • Each definition of success should have a corresponding action you expect to be complete by Day 3 and Day 7, e.g. has not messaged a user but signed up <3 days ago
  • Understand what failure looks like and once you see the signs, you need to intervene

Actionable takeaways:

  • Build per user usage (txn count and volume)
  • Build targeted docs, tutorials and case studies
  • Create success journey and intercept when not being achieved
  • Build targeted messaging schedule based on behavior (good and bad)

Hacks for before they’re signed up

Social login

  • 1 click signup which reduces friction
  • Increases monthly authenticated users / monthly unqiue users
  • Facebook is most popular preference for C2C, Google for business

Social login preferences










(originally from www.intercom.com)


Contextual tutorial

  • The more they complete these actions, the more likely they are to self trigger into a retained user
  • For example, Pinterest waits till you click on the picture to kick off the tutorial

Clear path to completion

  • Less likely to abandon if people know how long is left
  • For example, these could be steps, progress bar and checklists

Early value for the user

  • Focus on the job they want to complete
  • Twitter’s KPI on 20 users, so help you follow 20 people with 1 click

Progressive profiling

  • As for “just enough” information, e.g. LinkedIn asks you over time with “Strength rating”

Connect teams

  • Slack lets new team members join without additional permissions if you’ve verified with company email
  • If group is required to onboard then provide method to skip parts a user can’t do (e.g. business person can’t do javascript snippet).  Let them skip to the part they can accomplish.  Then provide invites to those who can unblock integration.



(originally from www.intercom.com)

Actionable takeaways:

  • Build social logins
  • Always show path to completion
  • Push to magic moment
  • Only ask for information when you can demonstrate value
  • Allow invitations so a team can join

3. Hacks after they’ve signed up

Onboarding new features

  • Bring on new features In the right context, i.e. when they’re feeling the pain or are in the right part of the site

new features


(originally from www.intercom.com)

  • Use educational content as your empty state, e.g. Trello provides welcome board with pre-made To Do cards which provide an explanation
  • Anticipate questions – give information in hints when they need it.
    “One of the best ways to do this is to center information around the intent of the customer. For example, when a customer creates a new campaign, by clicking on the create button they’ve shown intent. With new users interested, now is a good time to start sharing more advanced information like best practice guides. This type of careful consideration really does drive engagement.”

Actionable takeaways:

  • Build data driven messaging schedule – new features, risk of churn
  • Trigger updates for pro users who aren’t using all the features
  • Make sure every customer support ticket has two tags 1) product area and 2) type of conversation




6 months in

I’ve spend the last 3 weeks spending time with my alma mater, my investors and YC folks.  It’s been a rare opportunity to abstract myself from the grind of a startup and zoom out to 10,000 feet and think.  Here’s my learnings from the most recent experiences:

Successful people are human

A recent weekend brought the second ever YC Camp.  YC alums are invited to get offline for a weekend of mountain air, campfire chat and conversations with some of the most intelligent and successful folk in our part of the world.  Topics ranged from Trump to what’s more likely to end us: AI or synthesized biology.

You would be chatting to someone for 15 minutes around some smores about something interesting like what’s the real potential of chatbots, then I’d ask hey, what do you do.  Nearly always, my mind would be blown.  Amongst the ranks were Dan Ingalls, pioneer of object oriented computing; Justin Kan, founder of Twitch which sold to Amazon for $1b; Kevin Hale, who with little investment led a remote team to win in the online form space; Jared, who built Scribd and John Collision, who founded Stripe.  An illustrious list of successful folk.  There were lesser known names who demand just as much respect.  Oh, I just got acquired for a cool hundred million.  I’m from XYZ, which later research would reveal was worth a few billions dollars.  Yet, we invariably wore the same things: nike shoes, chinos, collared shirt and patagonia jacket.  We talked as equals and I was treated like one.  

Takeaway: success or failure – be human.

Be bold enough to have a conversation – they’re human too.

Be humble enough to never talk down – they’re human too.  

Think Big

I had many conversations with investors and advisors.  There were as many great pieces of advice relevant to our situation.  However, I was having lunch with one of my mentors when he  blew my mind.

We are going into a period of experimentation and had unconsciously drawn some constraints around our future paths: geographically and functionally.  Given our current status, we were looking to launch experiments that are a slight extension from our current product.  Instead, he smashed those thoughts by reframing our path to date.  We’re in a highly enviable situation.  We have time, a team, exciting markets and a willingness to fight.  We should think about solutions that can scale globally to solve the biggest pains we can find rather than limit our option set.  Mind blown.

Takeaway: reframe your current situation based on your strengths.  Now think global and do forward planning.

Think Small

Some of my favorite moments were outside, breathing in the crisp Bay Area air and contemplating life with some of the folk I get to call my close friends.  It seems our generation is one of contemplation with a willingness to change often and a desperate desire to find purpose and profit.  A recent Tim Ferris podcast had incepted stoic philosophical discussions amongst many of the conversations.

Strangely, it’s in these small moments I’m happiest.  When I abstract myself out and watch our conversation from above.  When I see a smile in my wife’s eyes.  When an investor/advisor or mentor blows my mind.  

In the grind of startup life I hadn’t had many of these moments in the past few months.  The last one was when one of the team sent me a Slack message that joining us was the best decision her career and that we felt like her family.  

Takeaway: I’m going to go for more small moments

Let me introduce Xendit


Let me introduce Xendit.  We are building mobile P2P payments in South East Asia.  We’re going to leap past debit and credit cards so people can transact via their mobile phone.

Check us out at www.xendit.co