Legal Tech Trainwreck

LegalTech Trainwrecks #1 (No Confetti)

Over the past two years, I’ve prototyped and discarded about a dozen potential legaltech products. It’s a soul-destroying process in many ways, but a journey that I think is necessary to discover not only what the market wants, but also what’s the right problem and product for me to be working on.

I’m sharing the stories from these failures so you can learn from them, salvage from them, or just be entertained, because who doesn’t like a good trainwreck?


I’ve reviewed a tonne of wedding venue contracts for friends and family over the years. 

Why wedding venue contracts? 

While a seemingly random niche, these are one of the highest-value contracts a person will sign in their lives. Secondly, as a result of COVID, couples became super focussed on the contract wording, in particular around cancellations and changes of date.

It usually takes me an hour to review and provide written comments to a couple. This is fine, but what’s really good is when a couple asks me to review a contract for a venue that I’ve already reviewed for a previous couple. All it takes is a quick check to make sure the venue is still using the same standard-form as last time (which is almost always the case), and then it’s a simple copy & paste of the previous comments with, at most, some minor adjustments. 

This made me think – I was only helping couples that personally knew me (and knew that I would do this for free!). There must be hundreds of couples looking at the same venues, who could benefit from pretty much the same contract review, which I could do once and then scale to all of them for a very reasonable price.

To be clear, the idea wasn’t really about wedding venue contracts. Thousands of standard-form contracts are dished out every day to small and medium-sized businesses who then have to hire their own individual lawyers (or they don’t because they can’t afford it). Wedding venue contracts were just a convenient initial testing ground for whether legal reviews could be provided in a more scalable, affordable and accessible manner for standard-form contracts of material value and importance.

The prototype

The good news was that wedding venue contracts are easily obtainable. Many venues attach them to the back of their glossy brochures, available for download from their website. Couples also emailed me directly, after discovering my service on social media, where I advertised free wedding venue contract reviews. I stuck my reviews on a Squarespace blog (hilariously called No Confetti), and I was off and running.

I remember being around 8 reviews deep and getting good feedback. This included couples saying they were willing to pay for these reviews. However, I was feeling increasingly uncomfortable the more reviews I wrote (and no, it wasn’t to do with the lawyer who acted for wedding venues and who threatened to sue me).

It turns out it’s actually really hard to review a contract for a hypothetical ‘client’. Couples’ desire for a particular venue ranges from ‘it’s an option’ to ‘I’ve been stalking this venue for years’. Some couples have lots of outside vendors coming in, some have none. Some weddings have guests arriving by car, and others have chartered a bus. Some wanted confetti, others didn’t know what confetti was. All of these factors, and more, influence what in the contract should be raised with the venue, and what can be safely waved through. I had overlooked this critical nuance.

One option was to ‘cover the field’ with comments, but that would necessarily mean a number of needless changes being put to the venue. That wouldn’t be helpful for anyone.

A second option was to have some type of method to filter for a couple’s specific needs. This could, for instance, be built into the text of the comments (e.g. “This point is only relevant if you are planning to have photographers stay past 10 pm”). Alternatively, I could get couples to indicate upfront the attributes applicable to their wedding, and then use some automated conditional logic to display only the relevant comments. All unattractive workarounds that would be time-consuming, fiddly and overcooked from a UX perspective.

You might ask why I didn’t realise earlier that this would be a problem since I had in the past been asked by couples to review a wedding venue contract that I had already reviewed for a previous couple. While this was true, I wasn’t doing it at scale, so the act of making minor adjustments to my previous comments to better tailor for the couple at hand flew under the radar. In the end, this was a good lesson in the importance of breaking down a process into its component parts and interrogating each of those, no matter how seemingly benign.

Lessons learned

Legal and other professional services have traditionally been delivered as a customised service to a specific client. The problem is that these services are becoming increasingly unaffordable for most people, and notoriously difficult to scale for the service provider. 

I thought I might have found a way to scale it, but when I got into the weeds, I couldn’t provide the service without sacrificing quality, and I couldn’t find a viable way around that.

Does this mean reviewing standard form contracts once and leveraging that review for multiple clients doesn’t work?

It didn’t work for me, but that doesn’t mean it can’t work.

Term Scout are having a go (I have no connection to them). It’s interesting to see how their product started with something quite similar to No Confetti but in the SaaS contract space, and then evolved into providing solutions like benchmarking against comparable contracts or clauses in the market. Oh, and they’ve raised $7.3 million in funding. Best of luck to them, but it was onto the next project for me.

If you’re interested in reading about more legal tech trainwrecks, please follow me on LinkedIn!

 Daniel Yim
Daniel Yim writes and teaches on legal technology and transformation. He is the founder of technology start-ups Sideline and Bumpd, and previously worked worked at Gilbert + Tobin and Axiom.

Back to blog