Monday, 26 October 2026

An Inscrutable Witness: Exploring the Admissibility of AI-derived Evidence

This article was originally published on Law News. It is republished here to include the acknowledgements section at the end!

The integration of Artificial Intelligence (AI) into criminal investigations is no longer a theoretical exercise for legal scholars. While much of the recent discussion around generative AI (genAI) in legal practice has centred on workplace efficiency and the risks of hallucinated case law, a far more fundamental challenge has arrived in the courtroom: the admissibility of evidence derived from AI systems.

As law enforcement agencies increasingly leverage automated analysis, such as connecting common cases together through series linking, matching biometric information such as facial recognition, and inferring behavioural analytics such as keystroke analysis, the criminal justice system must grapple with tools that are inherently probabilistic and opaque.

At the same time, as technology advances and people find more utility in the outputs of AI systems, societal expectations around the use of AI-derived evidence will shift. If AI-derived evidence can help establish the truth, holding offenders or responsible parties accountable, then we must consider if that type of evidence can help uphold an effective and credible system of justice.

In August 2025, this challenge was put to a rigorous practical test through a series of mock trial hearings hosted in the High Courts of Christchurch, Auckland, and Wellington. Presided over by real judges and argued by experienced counsel, the hypothetical case of R v Popper examined the evidential and statutory friction points created when Police rely on AI-derived intelligence to obtain warrants.

The Fictional Facts of R v Popper

The moot proceedings were based upon an invented AI software tool and an invented scenario: an application to exclude evidence seized during the execution of a search warrant, when the warrant had been obtained using information ultimately provided by AI.

Following the proliferation of MDMA pills bearing a distinctive "Goodnight Kiwi" logo at various music festivals, New Zealand Police identified an anonymous vendor operating on a dark web marketplace. Lacking investigative leads to uncover the account holder's identity, Police deployed a (hypothetical) novel, commercially-available AI software tool named TraceLex.

TraceLex utilises advanced "lexical analysis" to compare input writing samples against a massive, continuously updated database of publicly available online text, also referred to as Open Source Intelligence (OSINT). The system outputs candidate text matches along with a ranked list of prospective authors accompanied by confidence scores.

When Police put the writing samples from the dark web marketplace into TraceLex, the tool flagged matching content on Reddit. Police intelligence analysts examined the Reddit content for that account and discovered a screenshot of a utility invoice displaying Mr Popper's name and address, as well as a vehicle photograph containing a partial facial reflection matching Mr Popper. Analysts concluded there was a "high likelihood" (defined in intelligence standards as 75–85%) that Mr Popper operated the dark web account.

Relying primarily on this intelligence analysis, Police applied for and was granted a Surveillance Device Warrant under s 51 of the Search and Surveillance Act 2012 to track Mr Popper’s vehicle. Officers subsequently conducted a controlled drug purchase, observing Mr Popper leaving a package at a dead drop location. This observation formed the basis for a search warrant executed at Mr Popper’s residence, where Police seized substantial quantities of MDMA powder and pressed pills bearing the "Goodnight Kiwi" stamp. Mr Popper was charged with possession of a Class B controlled drug for supply.

The pre-trial hearing focused on two primary questions:
  • Was the Surveillance Device Warrant validly issued given its reliance on TraceLex?
  • If the warrant was invalid, making the evidence improperly obtained, should the resulting drug evidence nonetheless be admitted under the balancing test in s 30 of the Evidence Act 2006?

Designing TraceLex: The Technical Anatomy of AI-derived Evidence

To reflect the reality of modern machine learning tools without impugning existing proprietary software, and to mirror the legal pain points seen in the jurisprudence to date, TraceLex’s design in the R v Popper moot problem incorporated features of leading commercial AI applications which have been tested in international case law.

1. The "Black Box" and Commercial Sensitivity

TraceLex operates similarly to generative AI detectors, evaluating complex stylistic markers such as word choice, sentence structure, and punctuation syntax. However, the exact weightings behind its neural network remain an inscrutable "black box". Unlike traditional forensic handwriting or linguistic analysis, where an expert witness can explain the precise stylistic anomalies pointing to common authorship, an AI model cannot articulate why it reached a specific conclusion.

Furthermore, because TraceLex is a cloud-based, proprietary third-party product, its vendor invoked trade secrets and refused to supply source code or technical representatives for cross-examination. This mirrors controversial US jurisprudence such as State v Loomis 881 NW2d 749 (Wis. 2016), where the Wisconsin Supreme Court allowed the use of the COMPAS risk-assessment algorithm in sentencing despite its underlying code remaining a proprietary secret, so long as the risk-assessment report warned judges of its algorithmic limitations. In R v Popper, the Court had to rely on an independent expert who could only conduct external "black box" user testing.

2. Probabilistic Inconsistency and Non-Deterministic Models

Unlike deterministic, rules-based software that produces identical outputs for identical inputs, advanced AI systems are probabilistic and stochastic. This introduces variability and unpredictability. In the US decision Matter of Weber 2024 NY Slip Op 24258, an expert witness used Microsoft Copilot to produce his damages calculations. When the court performed its own cross-check by re-entering the same damages calculation prompt three times, Copilot produced three distinct figures, none of which matched the expert’s evidence. In R v Popper, defence counsel highlighted that TraceLex could produce variable and inconsistent results. They also pointed out that cloud-side updates by software developers could alter model behaviour over time, severely compromising the scientific requirement of repeatability.

3. Misinterpretation of Confidence Scores

TraceLex outputs a numerical “confidence score”, which (as seen in the R v Popper moot) humans often erroneously interpret as a linear percentage. In fact, AI scoring models are non-linear: an increase from 0.67 to 0.68 does not represent the same quantitative increment as a jump from 0.66 to 0.67. Inappropriately setting thresholds can become subject to challenge, as demonstrated in R (Bridges) v South Wales Police [2020] EWCA Civ 1058, where the UK Court of Appeal noted the dangers of a live facial recognition system’s similarity score threshold being set in an unclear way.

4. Mass OSINT Data Sourcing and Privacy

TraceLex relies on continuous scraping of public domain data, which may not be reliable in itself. Beyond accuracy, continuous scraping raises severe privacy concerns under s 21 of the NZBORA 1990. Defence counsel drew parallels to third-party data aggregation systems, such as automated number-plate recognition networks, where private databases are accessed by Police for law enforcement purposes.

Core Evidentiary and Legal Arguments

Common themes emerged across the three moot hearings.

1. Human-in-the-Loop vs. "Rubber-Stamping"

The prosecution contended that TraceLex was never used as a sole determinant of guilt, but merely as an investigative lead reviewed by experienced Police analysts. This "human-in-the-loop" framework was argued to cure any underlying technical opacity.

Conversely, defence counsel argued that human oversight is illusory if the analysts inspecting the output lack the technical literacy to understand the tool's error rates and failure modes. Although human analysts endorsed TraceLex’s match, manual lexical analysis across such volumes is challenging for humans. The technology ethics literature refers to the common consequence of this as “automation bias”, where humans tend to agree with the automated computer systems over time. Relying on TraceLex’s unvalidated vendor claims without independent evaluation before applying for a warrant was characterised by the defence as a breach of the applicant's duty of candour to the issuing officer.

2. Assessing Reliability under the Evidence Act 2006

Under New Zealand law, novel scientific evidence is evaluated under the opinion evidence rules of the Evidence Act, requiring expert evidence to be "substantially helpful" (an amalgam of relevance, reliability, and probative value).

In expert experiments conducted for the trial, TraceLex correctly identified the seven out of ten authors under realistic conditions in a single test. The Defence submission was that a 70% accuracy rate under small-sample test conditions demonstrates substantial unreliability, which cannot be cured post hoc simply because the defendant was found with the drugs in his home.

The Prosecution argued that s 51 of the Search and Surveillance Act requires only "reasonable grounds to suspect" an offence and "reasonable grounds to believe" probative evidence will be obtained. Scientific certainty is unnecessary; the threshold is lower than proof beyond reasonable doubt, and the tool's output formed part of a compelling "global picture".

3. Evidential Analogies: Informants, Calculators, or Hearsay?

Counsel tested several legal analogies to categorise AI evidence:

Anonymous Informants: Like confidential informants, AI outputs cannot be cross-examined, requiring independent verification to move beyond mere suspicion. However, unlike human informants, AI lacks human motives like malice or financial reward.

Scientific Instruments: The prosecution analogised TraceLex to calculators, breathalysers, or radar guns, where courts routinely accept technical outputs without inspecting underlying source code or electronics. The defence countered that breathalysers and other devices enjoy statutory presumptions of accuracy under the Land Transport Act 1998 and s 137 of the Evidence Act in part because they operate deterministically, whereas AI outputs are non-explainable and stochastic.

Hearsay: Academic commentary suggests treating AI outputs as hearsay. However, case law suggests that automated machine generation should be treated as documentary evidence, as hearsay requires a human declarant.

Expert Witness: Experts in criminal cases are generally expected to abide by the Code of Conduct for Expert Witnesses (Schedule 4 to the High Court Rules 2016). These require expert witnesses to give their sources, to state their reasoning, and generally demonstrate that their opinion or evidence is reliable. As a demonstration of how quickly the technology is developing, these requirements would have been difficult for early genAI models to meet in 2022/2023, but now in 2026 many products can provide their sources and explain their chain of thought. Where an AI is replacing the thinking of a human, could it be treated as an expert?

Section 30 Balancing Act & The Shadow of Tamiefuna

The secondary battleground across all three moot hearings was s 30 of the Evidence Act. If the warrant was invalid due to insufficient grounds or lack of candour, should the resulting physical drug evidence be excluded?

The prosecution and defence offered contrasting arguments across four key factors under the s 30(5) balancing test. Regarding probative value and reliability, the prosecution emphasised that the seized MDMA matched the festival pills, confirming TraceLex's accuracy; the defence countered that an opaque, unverified AI process should not be retroactively justified by post-search results. Regarding the seriousness of the offence and the importance of any rights breached, the prosecution highlighted the public harm of commercial Class B drug supply, while the defence contended that the fundamental privacy rights under s 21 of the NZBORA must be upheld regardless of the charge's severity.

The prosecution argued that there was a lack of other investigatory techniques for the untraceable dark web account, whereas the defence submitted that a lack of options does not excuse deploying unvalidated mass surveillance tools. Finally, the prosecution claimed Police acted in good faith based on international practices, while the defence argued that the use of TraceLex was reckless due to a failure to disclose the tool's known technical limitations to the issuing officer.

A central focus in the s 30 analysis was the Supreme Court’s decision in Tamiefuna v R [2025] NZSC 40. In Tamiefuna, Police took and indefinitely retained a photograph of a passenger during a routine, lawful traffic stop, later using it to link him to an unrelated robbery. The Supreme Court excluded the highly probative photograph under s 30, holding that the unlawful retention and database collation infringed s 21 of the NZBORA.

Tamiefuna is a reminder that improperly obtained evidence should not necessarily be admitted simply because it is reliable or because Police acted in good faith. Applied to AI, Tamiefuna could signal that, without careful attention to privacy obligations, long-term data scraping, intelligence retention, and reliance on black-box tools without clear statutory frameworks may constitute systemic impropriety. Such impropriety may be sufficient to warrant exclusion, even when the tool "gets the right person".

However, the s 30 balancing test must be applied in a context-specific way for every case, which can lead to difficulties in translating the outcomes to other cases. The Supreme Court has signalled that a recalibration of the balancing test is best left to Parliament to help address inconsistencies in applying the test.

The Verdicts: A Split Bench

The three High Court mock trials produced distinct rulings that reflect the current state of judicial uncertainty:

Christchurch High Court (Associate Judge Paulsen): Held the Surveillance Device Warrant was invalidly issued. TraceLex did not provide a sufficiently reliable foundation, and the warrant application was deficient and incomplete. On the s 30 balancing exercise, the Court tentatively leaned towards admitting the evidence due to the seriousness of the offending, though noting severe reservations.

Auckland High Court (Blanchard J): Held the warrant was invalidly issued. The probabilistic match did not satisfy the "reasonable belief" threshold required by statute, and Police lacked foundational reliability data. However, under s 30, the Court provisionally admitted the evidence, holding that Police acted in good faith and that the tool ultimately proved accurate.

Wellington High Court (Radich J): Held the warrant was validly issued. The Court analogised TraceLex to traditional technical equipment, ruling that an issuing officer needs to understand the nature and corroboration of the output, not the underlying software code. The Court added that even if invalid, the evidence would be admitted under s 30.

Practical Takeaways for Legal Practitioners

The R v Popper mock trials offer critical lessons for criminal barristers, prosecutors, and legal advisors navigating the emergence of AI-derived evidence:

For Prosecutors & Law Enforcement
  • Pre-Deployment Validation is Necessary: Police should not rely on post hoc expert validations commissioned after a legal challenge has been lodged. AI tools must undergo rigorous, independent baseline testing prior to operational deployment.
  • Heightened Duty of Candour: Warrant applications relying on AI outputs should explicitly state the tool's error rates, non-linear confidence scores, and limitations. Suppressing technical uncertainty risks invalidating the resulting warrant.
  • Meaningful Human Oversight: "Human-in-the-loop" processes must involve trained analysts capable of critically questioning AI outputs, rather than executing a box-ticking exercise.
For Defence Counsel
  • Challenge the "Machine Accuracy" Presumption: AI tools are not speed cameras or calculators. Highlighting their non-deterministic, probabilistic nature, and challenging any failure by Police to provide error rates or repeat-query testing, may undermine the apparent reliability of their outputs.
  • Interrogate Confidence Scores: Unpack numerical outputs to expose their non-linearity. The court may need education to understand that a "75% confidence score" does not equate to a 75% mathematical probability of guilt.
  • Apply Tamiefuna towards open source data collection: Mass data ingestion and retention practices may be challenged under s 21 of the NZBORA 1990. Arguably the State does not have unfettered rights to aggregate and profile personal data even if it is publicly available on the Internet.
Conclusion

While the moot hearings in R v Popper demonstrate that New Zealand courts may currently lean toward admitting highly probative evidence under s 30, law enforcement cannot rely on s 30 as a permanent safety net. As judicial technical literacy matures, opaque "black box" algorithms that bypass statutory safeguards will face increasing skepticism. To maintain an effective and credible justice system, the courts must balance the use of new innovative technologies against fundamental constitutional rights.


Watch the recording of the Auckland Mock Trial on YouTube: (https://www.youtube.com/live/0ofLQSC85hU).

The Mock Trial Document pack, including the intelligence profile, warrant application, and technical expert statement, is available here: https://tinyurl.com/ai-in-court-pack-2025.



Many hands make light work, and the success of the AI in Court events relied upon significant contributions from the many. We acknowledge:
  • The judges and the Courts of New Zealand for hosting the events;
  • Counsel: Claire Boshier, Kerry Cook, Helen Brown, Jacob Parry, Anselm Williams, and Chris Wilkinson-Smith;
  • Student counsel: Olivia Pearce, Helen Houghton, Nikita Gundawar, Yichen (Alex) Yang, Claire Graham, and Lara Hopkinson;
  • The Law Association and Meredith Connell for sponsoring parts of the events;
  • New Zealand Police for supporting the development of the moot problem;
  • Organising committee: James Foubister, Rebecca Thomson, Lloyd Gallagher, Jacob Parry, Matthew Mortimer-Wang, Prof Kris Gledhill, Dr ZoĆ« Prebble, Dr Olivia Erdelyi, Dr Briony Blackmore, and Lewis Mills.

We also acknowledge the AI in Court event hosted by Monash University’s Artificial Intelligence for Law Enforcement and Community Safety (AiLECS) laboratory, which served as inspiration for the mock trials.

This article was drafted with the support of Google Gemini, and the author takes responsibility for the writing and analysis.

Thursday, 18 July 2024

One weird trick to solve cap table ESOP calculations

A common challenge for capitalisation table modelling is the requirement for a fixed ESOP percentage post-investment. It’s hard to figure out exactly how many share-equivalent options should be allocated to that pool, when the valuation is changing, when the amount of capital raised is changing, when new shares are being issued and/or some old shares are being cancelled.

The standard experience of figuring out the ESOP pool size is:

  • Our proposed lead investor says we need to have 10% of equity post-investment allocated to an ESOP pool so that we can sufficiently incentivise staff and new hires.
  • We can model the current number of issued shares plus the number of new shares that will be issued as part of the capital raise, to calculate the total number of shares post-investment.
  • So if we take 10% of that number and allocate that to an ESOP... wait why does the spreadsheet tell us this is only 9.1% of the post-investment equity?
  • If we just keep trying differnt numbers... yeah that’s close enough to 10% to call it a day.

The problem is that the number of shares allocated to the ESOP changes the total number of shares used to calculate equity percentages on a fully diluted basis. If you increase the number of shares in the ESOP, the total number of shares increases, so to get to your target percentage you increase the number of shares in the ESOP more, and the total number of shares increases, and so on. Eventually you reach an equilibrium that is close to your target ESOP percentage, but if you’re off by even one share then the percentage isn’t going to be a nice and round number.

But there is a solution! It just requires some math... and you’ve already got a spreadsheet in front of you so the math shouldn’t scare you off. If we look at the first principles method of calculating the ESOP share allocation, we can express it with this formula:

Where SE is the number of shares to be allocated to the ESOP, SO is the number of shares allocated/issued to all others, and E is the targeted ESOP percentage. So for example:

The problem is that SE appears on both sides of the equation, and Excel doesn’t like that and will give you the dreaded circular reference error. But you can do some algebraic rearrangement to solve this:


As long as the ESOP percentage is 0% or 100%, then this equation will work – note that in Excel it has to be a percentage (i.e. between 0% to 100% or 0.0 to 1.0). It may look a bit odd with the 1s appearing in the formula, but I promise that it does work. Let’s look at a practical example:

So in E9 we can enter the formula =SUM(F3:F8)/(1/G1-1) and hey presto...

And now we can change the pre-money valuation...

Or change the amount of capital being raised...

Or change the target ESOP pool size...

Or just have some really weird numbers that are not round at all...


It shouldn’t take a PhD to do some algebraic manipulation, but I keep seeing cap table spreadsheets with hardcoded ESOP guesses that immediately break when you change any of the high-level parameters. So if you’ve read this far, just use this formula and everyone will have more flexible spreadsheets!

=SUM(“range of cells containing other shares”)/(1/”ESOP percentage”-1)

P.S. What if there are already ESOP shares issued? Just subtract the existing number of ESOP shares from the outcome of the formula, and leave that in the New Shares column:



Sunday, 10 March 2024

New Zealand Start-up Valuations Are Too Low. We Should Fix That.

This article is written from my personal perspective, and does not represent the views or policies of any past, present, or future employer or organisation I am associated with. 

The dark art/science of valuation - determining a fair value of a company so that investors can deploy money into a company, calculate a price for the shares, and therefore determine how much of the company they will get in return. I’m going to stick in an equation in a different font here so we can scare away most of the investors from reading the rest of this article:


V = C / E

(Post-money) Valuation = Capital Invested / Equity (as a decimal fraction in the range [0,1])

It’s one of the most important yet difficult points of negotiation in any capital raise. Important because it has long-lasting implications on financial returns, difficult because there is so little data to objectively determine a fair valuation when companies are in the early stages. Every investor, founder, consultant, ecosystem cheerleader, and their academically titled cat has a different view on how to approach valuation - here are some of the most common narratives:


  • How much money does the company need? I’ll buy 20% of the company for that, thanks.

  • How much money does the company need? I’m not giving up more than 0.24% equity so that determines the lowest valuation I’m willing to entertain.

  • What have other start-ups been valued at recently? Let me copy your homework, I’ll change it up a bit so it’s not obvious.

  • What was the company’s last valuation? Surely it can’t have tripled in the last 18 months, let’s call it 2.5x and move on.

  • Let’s apply a market multiple to your annual revenue. Don’t have any revenue yet? Well guess what it might be in 5 years time and we’ll discount it backwards, despite every single number in this process being a made-up assumption.

  • Here’s a spreadsheet that my third cousin’s physiotherapist gave me that has a lot of numbers in it, and it tells us the valuation is this. Just trust the spreadsheet.

  • What stage is the company? Someone in the US said to use these rules of thumb so now you’re worth a clean round $1 million.

  • How much would it cost to rebuild everything that the company has so far? Oh, that number’s really small, what if we also add in *waves hands* future potential?

  • What valuation does the company want to raise at? Whatever the number is, they have rocks in their head and we’ll slash it in half.

  • I was involved in a similar company ten years ago with a different product selling to a different market with a different team, so this company should be worth about the same.

  • Let’s propose this valuation. Oh, the company is using AI? We can triple it then!

  • Let’s use a convertible note so we don’t have to talk about valuation (yet).


If many of these narratives sound a bit… dumb, it’s because they are. Yet people will spend a lot of time debating valuation numbers, with little evidence and mostly vibes.


Ideally, the valuation should be the result of any other free market pricing mechanism - a willing buyer (investor) is happy to pay the price agreed with a willing seller (founders/company). But there are no pure free markets, and investing in start-ups is no different. There are supply constraints (limited investment capital), imperfect information exchanges (everything is confidential), and huge power differentials between the investors and the founders/companies (one party has all the money, the other party needs some of it, please). And despite the inherent unfairness in the market, you do still have to come up with a number that everyone can live with.


So now onto the controversial bit - New Zealand start-ups valuations are too low. Investors don’t want to hear it, because they think they benefit from low valuations (and are also mostly responsible for setting the valuations). Founders don’t want to hear it, because it’s depressing to know that keeping your company at home puts you personally at a financial disadvantage, and who wants to deal with the cost of living in San Francisco anyway? And my cat doesn’t want to hear it, because if it’s true, there are much broader economic implications that could be holding the New Zealand start-up ecosystem back from success (and therefore, after several jumps in logic, lead to less regular wet food and fewer treats). But firstly, let’s look at the evidence.


Is the claim true?

Exhibit A

Everyone has their stories (and I share a few in the below sections), but quantitative data paints the clearest picture. Pitchbook is regarded as the imperfect but most comprehensive data aggregator for the private investment industry. They scour the internet for press releases and they ask investors to update the data on their deals - while they might miss some capital raises or get some data points wrong, it’s mostly better than their competitors. Licences to access the data are pretty expensive, but anyone who wants to do valuation properly needs to have access to data about market trends and comparable start-up companies.


A few years ago, I participated in an exercise to compare New Zealand start-up valuations to those found in a handful of other geographies. Shout out to Liam Rollo (now in Australia with Breakthrough Victoria) for doing the heavy lifting of analysing the Pitchbook data. We looked at Deep Tech and SaaS companies with Seed, Series A, and Series B capital raises for the three year period between 5 July 2019 and 5 July 2022. All figures in the below tables are standardised to USD.


Deep Tech Valuations


SaaS Valuations


Before anyone gets too excited, yes the New Zealand sample sizes are small, and there is a feeling that there should be more data points in there (particularly on the SaaS side), but the medians seem consistent with other data sources like the Startup Investment New Zealand report. These are medians, as to minimise the impact of outliers, so that one company you’re thinking of that bucks the trend isn’t really relevant to this discussion. The stage definitions are based on how the capital raise was classified in Pitchbook, so there may be differences in expectations between jurisdictions. We can and should challenge the robustness of any claims made on the basis of this limited data, but it’s also the best data we have, and the size of the effects are just so large that we need to pay attention.


The data shows that NZ start-up valuations are lower than in jurisdictions we like to compare ourselves to (like Singapore, Israel, UK, Australia), and a lot lower than in the USA, especially for really early-stage companies (Seed). To describe the percentages in the opposite direction, NZ Seed-stage deep tech valuations are about 70% lower than in the USA, and NZ Seed-stage SaaS valuations are about 53% lower than in the USA.


We also looked deeper into the data - both more historically (back to 2010) and more longitudinally (for companies up to Series D). There are a lot of data tables that I won’t include here, but we found the valuation gap to be persistent (60-70% lower Seed valuations than USA from 2010-2022) and reducing as companies become more mature (Series D valuations were much more similar to international counterparts). On the latter point, we identified that NZ company valuations “catch-up” to other jurisdictions as the companies grow, because as the rounds get larger the higher the likelihood of NZ companies raising capital from international investors, with international investor valuation expectations.


Exhibit B

Some of the local investors know this claim to be true, because they say so in their pitch decks when raising capital for their Funds. Out of the slides that I’ve seen over the years, one pitch deck from 2021 says New Zealand has “many undervalued startups: 30% below the Bay Area”; another from 2022 says NZ “Valuations are ~50% below US startups”. Peter Beck is quoted in TechCrunch saying “New Zealand’s valuations on average are about 50% lower than most companies coming out of Silicon Valley”. As the data in Exhibit A shows, these estimates might be generous to NZ.


Why is this a relevant point to put in a pitch deck for a fund? International investors are being told “hey, invest in New Zealand start-ups because you can score yourself a deal!” Buy low(er), sell high! The implication is that companies of comparable quality and likelihood of success are significantly cheaper in New Zealand than in California. In economics terms, if there is such a significant arbitrage opportunity for investors, where are the market corrections? Or is something keeping the market inefficient? More on this later.


Exhibit C

Most early-stage start-ups (particularly pre-seed/seed) are funded by local New Zealand investors. They’re the investors that understand the ecosystem, know how to navigate the regulatory landscape, and can most easily develop connections with the founders. But every now and then, an international investor sees opportunity here, and blows all the local investors out of the water.


Just last year, a promising start-up attracted the interest of an Asian VC fund at Seed stage. Local investors submitted term sheets with a (pre-money) valuation around NZD$5M, and even then it was like pulling teeth, with most local investors commenting that it was way too high. The international investor offered a (pre-money) valuation of NZD$12M. No chocolate fish for guessing who the start-up went with! Why was there such a big gap? This was the international investor’s first term sheet in New Zealand, and they didn’t come to play the New Zealand game - they were already competing in a global game that most local investors have no idea how to play.


Exhibit D

The recent Callaghan Innovation Technology Incubator Request for Proposals has an answer to a question about equity expectations that says “Our policy settings state that Technology Incubators are expected to use their investment to purchase up to 20-50% of equity in the start-up. Requiring 20-50% equity is intended to ensure that only sufficiently early stage and complex/deep tech start-ups are invested in.” That’s a government agency telling the market that they expect valuations to allow for 20-50% equity to be taken in exchange for a $250k investment (plus the $750k Repayable Grant that should be treated as debt, not equity). In a worst case scenario, that’s effectively a (pre-money) valuation of $250k for a pre-seed company, and in the best case a (pre-money) valuation of $1M. This is worse than just signalling, because this is an active intervention that is suppressing valuations below what the market might otherwise provide. [To be fair to Callaghan, they also say that a lower 10-20% equity holding can be approved where there is a strategic investment syndicate - but you can cross-reference the recipients of Repayable Grants with ownership data on the Companies Office to see how frequently that has happened. And to be fair to Callaghan, if the intervention is supporting companies that otherwise wouldn’t have raised capital, then arguably it serves its purpose.]


What are the consequences? 

So I think the evidence shows NZ start-up valuations are low, but also that they’re probably a lot lower than most people might have expected. And moving away from evidence towards reckons, I believe that a NZ Seed stage start-up should not be 30%, 50%, or even 70% less valuable than a comparable company in the US just because it’s working out of New Zealand. Sure, US companies draw from a larger pool of founders, there is a stronger network effect, and they are operating in larger markets, but 70% seems too much of a difference. Some might claim that this is the impact of exchange rates, but at most that would have a 33% impact (and given that it is a more predictable element of valuation, more priced in).


If valuations are artificially lower than where they should be, then there are two key consequences for Kiwi start-ups. The first is that, assuming the company needs a fixed $x to be able to get to the next capital raise, then a low valuation will lead to investors taking a larger proportion of the company. The people working in the company (including founders and equity-remunerated staff) will therefore earn less of the financial reward if they are successful. We might say, who cares, they’ll still be rich - but the main problem is that when the companies seek subsequent rounds of capital, bigger (and often international) investors claim that the “cap table is screwed” because the “founders are insufficiently incentivised to outperform”. And then they say the dreaded word that no one really wants to talk about: recapitalisation. A bunch of pain and difficult conversations, because the earlier valuations were too low. Or worse, no capital raise (and therefore company failure) because no one wants to do the work of a recap, or the investors can’t all agree before the company runs out of time.


The second consequence is that, assuming the investors want a set percentage of equity (some investors have a minimum requirement to make it worthwhile for them, some investors have an upper limit that they are willing to hold for risk diversification reasons), then a low valuation will lead to the company being undercapitalised. That is, the company won’t be able to make enough progress, or be able to spend on things that would make the company successful, and then fail to impress investors at the next capital raise. The Startup Genome report for NZ states (slide 72) that “The Median Series A round for NZ startups is quite small compared to peer ecosystems… and make[s] them look less attractive to future investors.” Kiwis are proud of their Number 8 wire mentality and being able to make a dollar stretch further than overseas competitors, but efficiency doesn’t necessarily lead to winning, and it can also be another source of failure risk. A bunch of wasted talent, time, effort, and sweat, because the earlier valuations were too low.


These are both generalisations, but they also happen far too often in the New Zealand market. And unlike other reasons that a company might fail (lack of product-market fit, competition, regulatory/legal challenges) which are mostly external and beyond the direct control of the company, valuation is entirely within the control of the company and its investors, who should be aligned in wanting the company to succeed.


Even where the company does manage to make progress, start-ups where the founders have less equity are more likely to exit early, for lower amounts of money. This limits the potential returns for both founders and investors, which reduces the amount they have to invest in further ventures, which delivers poor performance and track records for the ecosystem, and the flywheel of growth never really kicks off. This is where the problem can be hard for individuals to rationalise but is actually really consequential - it's not a problem that just affects individual companies, but the performance of the ecosystem as a whole, and therefore its contribution to the national economy.


I note here that there are some claims that valuation is negatively correlated to failure rate (i.e. companies with lower valuations are more likely to fail). I don’t think this correlation is relevant because companies also get higher valuations as they make progress and succeed and get to subsequent stages of capital raising. Success breeds success, so to say that a metric that is a proxy for success is negatively correlated to failure isn’t that interesting. If the described correlation was within a funding stage, then maybe there is a point, but I haven’t seen any data demonstrating that yet.


Are the (systemically) lower valuations hurting our ecosystem as a whole? 

To be clear, valuations that are too high present their own set of challenges, so jumping to sky-high valuations isn’t going to solve the problem for New Zealand either. Why we shouldn’t immediately copy Bay Area valuations requires another standalone article that talks more about culture and hubris. And an important point for companies seeking an acquisition exit pathway - valuations that are too high might eventually price your company out of an acquisition.


It’s hard to concretely make a claim about the ecosystem though. In theory, low valuations disincentivise founders from taking on the risk of going on a start-up journey because they will probably get less reward out of it, but I don’t believe many founders in NZ think in that way. No one wants to leave money on the table of course, but most founders are doing start-ups because they are passionate about their idea and want to make their mark on the world [and sometimes they want to be their own boss and exercise a high locus of control but find out quickly that even CEOs have bosses - that dynamic is worth another article]. 


Something that we are missing in the NZ ecosystem is a rigorous, broad study of start-up company failures (also morbidly called post-mortems) to produce evidence for any common themes (and therefore inform potential interventions to mitigate risk). Probably because most people don’t like to talk about failure, so the stories get swept under the rug. Do we have more start-ups failing in NZ than other comparable jurisdictions? We have no idea.


But I think that low valuations are symptomatic of investor behaviour where the emphasis appears to be on “scoring a deal” in the short-term, and forgetting (or wilfully ignoring) the long-term impacts.


Take the issue of high founder dilution leading to difficult capital raises later down the line (and likely recapitalisation). All professional investors know that future investors will need to see the founders holding sufficient equity, yet we still see Pre-seed and Seed rounds where the investors are happy to take up to 50% equity. I’ve seen multiple companies where the founders have told their existing investors that potential future investors are signalling that there are cap table issues - and the Board/investors do nothing because they hope that it will all work out for them. While company failure can usually be attributed to multiple reasons, there have been a bunch in the last year alone that can likely be attributed to cap table structures making it that much easier for potential investors to say no in a tough capital market, and then the company running out of money.


A significant factor in the New Zealand ecosystem is that there is relatively low competition amongst investors, which leads to cartel-like behaviour (which, to be clear so that no lawyers get mad at me, is not the same as cartel behaviour). Local investors all talk to each other about potential investments, and while there isn’t price-fixing via closed-door agreements to offer low valuations to start-ups (that I know of), there’s plenty of social signalling and pressure that leads to herd behaviour. Most people don’t want to look dumb or be judged by their peers for offering high valuations - and even those who don’t care have Investment Committees or other governance entities that try to ensure that the investors are getting a good deal. And consistently high(er) valuations can make it hard to syndicate/work with other investors who still have low valuation expectations, which can leave you quickly isolated in an ecosystem that needs a lot of co-operation to succeed.


Unfortunately, investors thinking they are getting themselves a short-term win can often become long-term losers. Owning 50% of a company that has failed is still a $0 outcome. And an ecosystem that is full of short-term wins has to be pretty nervous about its long-term prospects. It’s hard enough to generate a win, so we shouldn’t let valuation add any more risk than absolutely necessary.


What do we do about it?

There are two parties that could do something here. NZ investors could realise that (artificially) low valuations actually hurt them in the long-run, and start benchmarking their expectations to international numbers. We keep telling our founders and companies that they need to play in the international markets and set their sights overseas as soon as possible because New Zealand is too small - why don’t investors take some of their own advice? Investors are in a position of power in most investment discussions and negotiations, and I believe there is a duty of care owed to the founders - remember that most founders have N=1 experience (i.e. their own company), whereas investors are acting with N>1000 information. If the investors don’t know how to set a valuation well, then maybe they should consider using convertible/SAFE notes to reduce the likelihood of making a mistake (even if it might come at the cost of lower short-term returns).


While some people reading this article might sagely nod their heads, most investors will be frothing at the mouth and deleting my phone number from their contacts, so I don’t think we can realistically hope for a collective Eureka moment. When markets are inefficient or imperfect, we have to call upon governments to introduce interventions and regulations. Telling founders that investors should take up to 50% of their company for a pre-seed round is wildly in the wrong direction - it’d be like the government saying that all houses should be worth at least $2 million. Removing that poor signalling would be a good start. 


Collecting and releasing better (anonymised) data would help reduce information asymmetry and allow all investors and founders to make fairer decisions about valuation/pricing. New Zealand Growth Capital Partners (NZGCP) already collects a lot of this data, but hasn’t been resourced sufficiently to produce benchmarks (but maybe the new Dealroom database will help). Promoting competition by supporting the establishment of more professional investment firms, rather than supporting the same existing ones, could also force incumbents to have tougher conversations about innovating on their investment models. Other policies to increase the attractiveness of investing into start-ups generally (another article in itself) would also hopefully increase capital supply and therefore likely have an upwards effect on valuations - but we’d need a lot of capital (like perhaps a 1%-of-all-Kiwisaver-funds amount of capital) to close the gap on other jurisdictions.


These are pretty mild as suggestions go. It’s not like I’m saying the government should establish price controls and say all start-up companies have to be valued at a certain minimum level, or to do ~something~ to the tax system. I once pitched the idea of a government-backed founder insurance scheme and a relatively prominent investor called me a Communist (which he probably thought was more insulting than I took it), so big ideas don’t scare me. But I get that it can be costly to make noise and kick up a fuss in an ecosystem that is small and encourages conformity, and the engineer in me asks for realistic and achievable answers. 


If you have read this article and also believe that start-up valuations are probably too low in New Zealand, then keep talking about it to as many people as you can. Remember, the market is actually made up of people. Talking about these issues encourages people to actually think about what they’re doing rather than defaulting to the norm. Eventually, the norms might just shift. Maybe my instagram should be exclusively focused on start-up company valuations. Might be a bit niche.


Maybe I don’t have the answers on what to do yet, but hopefully what I’ve written here is some food for thought. My point is simply this: that higher valuations (closer to international levels) for New Zealand start-up companies could increase the likelihood of success and mitigate failure risk, giving us more winners to cheer on. Isn’t that something everyone wants?


Thanks to my awesome friends and colleagues Will McKay, Kiri Lenagh-Glue, Olivia Ogilvie, and Liam Rollo for reviewing this article and giving valuable feedback. Opinions, errors, and mistakes are my own.


If you’d like to learn more about this topic, here are a couple of resources that I read (mostly in the US context, mostly in the SaaS context) while working on this article: