“Essays was not written in neat order,
from beginning to end.
It grew by slow encrustation, like a coral reef” 1

All That Glitters

Don’t be scared to stand out from the crowd. But fight the urge to constantly present yourself as more successful than you are.

Anything vs Everything

Choose what you’re going to focus on, and then have the conviction to say “no” to everything else.

Be a Good Dictator

Think about the intersection of the things that you care about, have authority in and are prepared to take responsibility for.

Being Amish-ish

How do we decide what technology to embrace and what technology to avoid?

Being Spartan with Ideas

Do you leave your ideas to fend for themselves in the wild or keep them in a safe place?

Break Points

Startup teams often grow suddenly, in bursts. Can we anticipate these points where our ways of working together typically break?


Building An Ecosystem

How can we build an ecosystem of innovative technology startups in New Zealand?


We can choose to be busy or remarkable, but probably not both


Callaghan, Revisited

How do we build on Paul Callaghan’s vision for New Zealand, and update it for our current reality?

Clarity Metrics

Do our metrics help us to make decisions, or do they just make us feel good?


A startup that goes well can be very rewarding. How do we ensure that everybody involved gets their fair share?


What do we gain and what do we lose when we treat the world as binary?


How do all of the programs designed to support startups actually help?


Conquering challenges requires understanding our relationship with pain


A portfolio approach to early-stage venture investment doesn’t really help and probably hurts.


Those without naturally want more. Meanwhile, those who have a lot want less. How do we all decide how much is enough?

Feedback Loops

Be more explicit about the sort of feedback that is useful, right now.



Here is some unusual advice for people working on a startup, or thinking about it: swim.

Four Types of Fun

Is it fun in the moment or when you reflect later? Or neither?

Getting Lucky

How do we break luck down into its component parts, so we can create luck for ourselves and for others…

Good, Fast & Cheap

What are we prepared to compromise in order to get what we want?


How do we create an ecosystem? We plant a seed and let it grow!

Hockey Stick Growth

It takes a long time to become an overnight successs. But to get there we need to be growing from the beginning.

How to Be Wrong

There are actually only three ways to be wrong about our impact: neglect, error and malice.

How to Decide

When we’re faced with a difficult Yes/No decision, how do we choose?

How to Get Old

We only get to be each age once. How many will we waste trying to be something that we’re not?

How to Pitch

We realised that the most effective investment pitches we receive all start with the same two words…

How to Scale

What a founder in one of the poorest areas in Kenya taught me about how to start and how to scale

How We Win

How well does your team understand your plan to win? When was the last time you wrote it down or said it out loud?


Rather than trying to copy what others have done, what can we do first?

Inconvenient Values

Why is it so hard to articulate and document shared team values?

Investment Lessons

Here are four simple but uncommon ideas about investing…

Leap of Faith

It’s important that we don’t confuse risk with uncertainty. We need to be clear about what we know is true and what we hope might be true.

Learning Russian

Use the Metrics Maturity Model to improve how we measure and report our progress.

Lessons from #RedPeak

Let it go. It’s what you learn, after you know it all, that counts.



Lie, cheat or spin, and we allow a gap to develop between perception and reality.

LOAD * ,8 ,1

Stay curious about how things work, and how you can use them to make things of your own.


Long Enough

How would treating time as a variable that we can influence change the way we behave and the choices we make?

Machines & Phases

There are so many different ways to measure a startup. It’s easy to drown in metrics. How do we know what we should focus on?

Measuring Impact

How do we know when something is actually working?


What rugby teams and rowing squads can teach us about building and managing diverse boards and executive teams.

Most People

To be considered successful we just have to do those things that most people don’t.

People, People, People

When we ask the best startups what’s holding them back they all point to the challenges of finding and keeping great people.

Picking Winners

Imagine objectively selecting companies to receive government support, without the bureaucrats or consultants?

Pining for the Fjords

Be honest: can we get to the next milestone with the resources we have?

Preaching to the Choir

Should we categorise ourselves based on the conversations that are comfortable and easy or uncomfortable and hard?

Product Management

Try to complete as many loops as possible, getting a little bit better each time.

Reality Distortion Field

Rather than looking for reality television inspired short cuts, maybe we just need to embrace sucking while we get started?

Rich vs Famous

If you had to choose, would you rather be rich or famous?

Rocket Fuel

Rather than complaining about how difficult it is to raise venture capital in New Zealand, we need to start being honest about why it’s hard.

Say Something

Anywhere I would have followed you. But I’m giving up on you!

Scar Tissue

Working on a startup is much more like racing a BMX bike than riding a roller coaster.

Show Me the Money

Trying to decide how to fund a startup? It’s important that we ask the right questions.

Startup Theatre

To encourage more people to work on startups, we often try to make them fun. How does that hurt?

The Dip

Why do the most interesting bits of startup stories always get airbrushed out?

The Far Side of Complex

How do we get beyond complexity?


The Mythical Startup

Can we update the fairytale version of how a technology startup becomes a success?

The Pit of Success

It’s not what the software does, it’s what the user does that matters.

The Size of Your Truck

As we grow, take the time to understand unit economics.

The Tyranny of Distance

New Zealand is often condescendingly described as a small island a long way from anywhere. Is it, though?

Trading Up

When a startup is sold, in part or in full, it is just a trade. As a country that is entirely dependant on trade for our prosperity we should understand this better.

Unit of Progress

Be specific about where we are going and what it will take to get there.

Video Call Etiquette

Simple polite rules we can use to improve our video call experience

Visualise An Audience

Need help empathising with users? Just imagine they are all in the room!

We Are Still Divided

The world is still divided, between you and me, baby, you and me.

World Class

The expression “world class” gets casually thrown around, like a frisbee at the beach. But what does it really mean?

1. Sarah Bakewell on Montaigne … or these essays too.