Technical Due Diligence Checklist

29 08 2016

From time to time, I get asked to perform technical due diligence on investment opportunities.  I have a checklist, and I thought I’d share it with others in the hope that it might be useful.

If you have anything you think I’ve missed or got wrong, please let me know in the comments, and I’ll [potentially] edit the list to suit.


  • Describe the overall architecture of the system.
  • Well documented?
  • Easily understood?
  • Industry standard components?
  • Many vendors (eg AWS, Azure, etc)?
  • What’s the next big architectural leap?



  • Any monitoring happening now?
  • Ever done load testing?
  • What are the potential bottlenecks and remedies?



  • Load balancing?
  • Separation of functions?
  • Any single points of failure?
  • Automatic [ability to perform] scaling?
  • Cost structures (eg licenses)
  • What isn’t automated that should be?
  • What’s the next scalability hurdle?



  • How are {passwords, sensitive information} {stored, backed up, transmitted}
  • HTTPS?
  • Protection against obvious stuff covered, eg XSS, SQL injection
  • Ever done penetration testing?
  • What requires root access; who has it?
  • What are your upgrade / patching regimes?
  • What’s backed up? Where? Ever done a disaster recovery (DR) test?
  • How would you make the site more secure?


Development processes

  • What languages and frameworks have you used? Why?
  • Who’s in the dev team?
  • How is the team organised? How do they communicate and make decisions?
  • Revision control on all platforms (eg iOS, Android, and back end)? Which – Git, Github, Bitbucket, etc?
  • Test Driven Development?
  • Doing Continuous Integration? Which tools?
  • How does deployment work?
  • Describe the accumulated technical debt, and how this is managed.
  • How would you improve the development team?



  • Is the source code readable and/or beautiful? Is there consistent style?
  • Are there copious comments in the code?
  • Is there narrative commenting for each code unit (object, method, etc)
  • Are they running on current releases of underlying software? Any big changes on the horizon?
  • Are there any unexpected or obscure dependencies?
  • How hard would it be to pick up and move to (AWS, Azure, Rackspace, etc)
  • Any long-term viability issues with specific vendors?
  • How could you improve maintainability?


Licensing issues

  • Do you own all of the code necessary to run the system?
  • How is it licensed?
  • Does anyone else have rights over the code? Could anyone else claim to have rights over the code?
  • If you’re using any licensed code, what are the terms of the license(s)? What are the risks associated with those licenses? Are there any plans to re-engineer these bits over time?
  • Is there an IP strategy, eg “SaaS black box running our proprietary code, accessible only through the web site and our API’s”



  • Are there any other interdependencies with stuff beyond your control?
  • If you were investing in this company, is there anything else you’d like to know that we haven’t asked about?
  • Any other comments?

Brian Christian on Algorithms to Live By

17 07 2016

I’m a member of the Long Now Foundation, whose mission it is to “…provide a counterpoint to today’s accelerating culture and help make long-term thinking more common. We hope to foster responsibility in the framework of the next 10,000 years.”

One of their main activities is producing Seminars about Long Term Thinking, which are available as podcasts, and are my favourite listen on a long drive or trip to the supermarket.

The latest episode is Brian Christian on Algorithms to Live By, which covers recent developments in computer science. He spends much of the talk discussing the “Optimal Stopping Problem“, in which you try to determine the optimum time to stop looking for the ideal house, partner, or similar. It turns out there’s a mathematical answer to this question – if you determine how long you’re prepared to engage in the search process, then you should spend the first 37% (1/e) of the search period examining the choices, and then select the next option that is better than any of the previous choices. There are a significant number of other gems in this talk, but Christian’s parting shot really cracked me up.  According to Computer Science he says, we can rethink rationality in a mathematical way that includes the following principles:

  • Don’t always consider all your options
  • Don’t necessarily go for the option that seems best every time
  • Make a mess on occasion
  • Travel light
  • Let things wait
  • Trust your instincts and don’t think too long
  • Relax
  • Toss a coin

It leaves me tempted, for a few milliseconds anyway, to retake my Computer Science degree.

See the video at:

Access Granted

17 06 2016

The great folks at the Access Granted podcast published a wide-ranging interview with me today on “the mosaic of my life”, which you can listed to below:

I cover a quite a lot of ground, including:

Enjoy, and thanks to Mike and Raj!

Not because they are easy, but because they are hard

5 05 2016

Every once in awhile, you come across something so inspirational it sends shivers up your spine.

While watching The Martian the other night with Mr 12, they included a snippet from John F Kennedy’s Rice Speech, which JFK delivered when I was two years old.  I’d seen the quote before, but I’d never seen the entire speech. It’s worth the 17 minutes to watch, not only for the inspirational content, but for the inspired way in which the speech was constructed.

This notion is at the heart of every startup, and indeed of most worthwhile human endeavors.

“We choose to go to the moon. We choose to go to the moon in this decade and do the other things, not because they are easy, but because they are hard, because that goal will serve to organize and measure the best of our energies and skills, because that challenge is one that we are willing to accept, one we are unwilling to postpone, and one which we intend to win, and the others, too.”

“But if I were to say, my fellow citizens, that we shall send to the moon, 240,000 miles away from the control station in Houston, a giant rocket more than 300 feet tall, the length of this football field, made of new metal alloys, some of which have not yet been invented, capable of standing heat and stresses several times more than have ever been experienced, fitted together with a precision better than the finest watch, carrying all the equipment needed for propulsion, guidance, control, communications, food and survival, on an untried mission, to an unknown celestial body, and then return it safely to earth, re-entering the atmosphere at speeds of over 25,000 miles per hour, causing heat about half that of the temperature of the sun — almost as hot as it is here today — and do all this, and do it right, and do it first before this decade is out–then we must be bold.”

Which begs the question: what happened to America in the last 54 years? Perhaps that’s the subject of a future blog post.

The Residents of Wellington

27 04 2016

Thanks to Lucy Revill at The Residents of Wellington for doing a really nice article on me.

An enthusiast, investor and business mentor he can often be found coaching startup companies through the Lightning Lab Programmes or mentoring teams of early-stage entrepreneurs at Wellington Start Up Weekend.


Why is Wellington such a great place for startups? It all comes down to scale. “We are not so small we don’t have resources but we are not so large that we fragment into self contained inward looking groups. People really do want to work with each other in Wellington, even with people they don’t like. We all want to make Wellington better. And it helps that you can walk across town in 20 minutes – although it takes you 30-40 because you keep on bumping into people you haven’t seen in a while – it’s great. If I go to the airport and I don’t run into someone I know I feel cheated. It’s like family. That scale is very important and I don’t want to lose it. That’s all.” With Dave on board, I feel confident as a Wellingtonian that Wellington will continue to be a great place to start something up, for years to come.

The essence of creativity

16 02 2016

Creativity is the spark that occurs when you combine seemingly unrelated things, shove an uncooperative idea into an unexpected context, or look at something familiar in a radically unfamiliar light. That spark of creativity is fun and essential, but much more difficult and rewarding is turning that spark into a steady flame or bushfire of enterprise through experimentation, empathy with your audience, and dogged determination. This is the task most start-up founders face

See more quotes on Idealog.

Convince me to invest in your startup

13 12 2015

What do angel investors like me look for in investable early-stage companies?

It’s all about:

  • You and your team
  • Your market
  • Your startup
  • Your progress
  • Your financial plan
  • Your investment terms
  • Your other investors
  • (and a few other things too).

Watch the video of a talk I gave on the subject at CreativeHQ‘s Startup Garage last week, as part of an introductory series for Lightning Lab XX.

You’ll also find my slides below.

Two aerial photos

1 12 2015

I recently arrived back in Wellington from the Startup Nations Summit in Mexico. On my flight from Auckland to Wellington on 29 November 2015, I passed over the Karori Rip just south of Mana Island.

The Karori Rip

The Karori Rip is an interesting phenomenon, basically a standing wave formed in specific tidal conditions in Cook Strait.  In this case, it was high tide on the Pacific (left) side, and low tide on the Tasman (right) side.  In the photo, you can see the wave roiling.

Then, on the same flight, approaching Wellington Airport from the north, I was welcomed back home by this:

Wellington City

I fall in love with Wellington over and over again. After being in the cities of North America with dubious air quality, she was truly a sight for sore eyes.

The New Christchurch – You Beauty!

6 11 2015

There’s only one thing I want to say today: Christchurch, you beauty!

When people ask me what I’m about, I tell them I’m building the future I want to live in. We’re all doing that today, here at Lightning Lab Christchurch Demo Day.

Look around you. The New Christchurch is filled with diversity and entrepreneurial spirit. We are transforming the brain drain from the quakes into a brain gain.

The New Christchurch was not prototyped with number eight wire and built in brick, it was laid out in a CAD system and is being fabricated in high-tech materials.

In The New Christchurch, the first question people ask you isn’t “what school did you go to”, it’s “what startups are you involved with” or “what countries are you doing business in”.

We’re building the future we want to live in, right here, right now. It’s a job too important to be left to government – they’re an important partner, but it must be led by people willing to take risks. Investors, that’s us!

While we mourn the losses from the quakes, we’re excited about that future.

Cantabs, you’re the most resilient people I’ve ever met. I want you to know that today, the rest of the country is here backing you.

So investors, don’t hold back. These Lightning Lab companies are The New Christchurch, and the future of New Zealand.

Let’s build that future together.

Address to the investors at Lightning Lab Christchurch Demo Day, 5 November 2015



The cohort at Lightning Lab Christchurch 2015



Legal Māori Resource Hub

22 10 2015

One of my “day jobs” is providing lexicographical software development for a number of dictionaries around the place.  One project using my Freelex software that’s recently been launched is the Legal Māori Resource Hub, by Māmari Stephens at the Victoria University Law department.

Māmari recently gave a talk about the lexicon, corpus, and resource hub at the National Digital Forum conference this year.

I’m really happy to have been involved in providing the underlying system on which this is built.