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.