Legaltech Careers: Sam Smolkin, CEO & Founder of Office & Dragons

Should lawyers learn to code? Well, Sam Smolkin did, built an enterprise app — Office & Dragons — and a growing customer base of law firm clients.

From humble beginnings, paying his way through college, Sam ended up as a private equity M&A lawyer at Kirkland & Ellis before launching his own start-up.

But it was an early interest in, and experience of, engineering that made Sam see legal processes differently.

For Sam, legal processes have too many repetitive manual steps crying out for simple yet powerful automations. Absent of targeted automation, these task types are inescapably time-consuming, often written off by lawyers, and demoralising for junior lawyers.

Yet they persist. Sam thought there must be a better way.

Hacking away during weekends and evenings, what started as a side project to automate his most boring legal tasks quickly morphed into the kernel of a business idea that he later validated via a variety of means before launching a start-up.

Sam’s story is a real-life example of how blending engineering and legal skills can allow you to reimagine legal work and find out ways to reduce waste in legal processes and improve productivity through targeted use of tech, creating great value for lawyers and their clients.

Take us back to the start. How and where does your career kick off?

My first proper jobs growing up in Michigan — the auto manufacturing capital of America — involved working night shifts in auto parts factories. My dad is a manufacturing engineer, so he set me up. Compared to the other jobs you could have as an 18-year-old in Michigan, it was actually relatively good pay.

Alongside working in auto parts manufacturing, I attended community college, which for non-US folk reading this is a cheap university you can attend without needing to get any kind of good SATs (entry exams) or anything like that.

My first two years of studies for my bachelor’s degree were done at community college, whilst living at home and working in an auto factory.

I saved money and paid my own way through college, so that’s what really got me started. Eventually I transferred to the University of Michigan, which is a well-established university in the States.

Working in an auto factory and studying at community college is something people usually find surprising given I later end up as a corporate lawyer at Kirkland & Ellis, which is pretty far removed from the experiences of many of my former colleagues.

What did you study before your JD?

I started off studying chemical engineering because I thought I would be some sort of engineer like my dad… but I got seduced by the dark side of liberal arts. I was a typical edgy teenager and into philosophy and that kind of stuff.

Or at least I thought I was.

The idea of not just doing math and science, and instead also doing some linguistics and philosophy was pretty appealing. Somewhere along the way, I got really into linguistics.

That led me to spend two years as a research assistant for a professor in computational linguistics, which is the science behind natural language processing. That was my next serious work experience. I helped with ordinary research, but I also spent a lot of time designing and running the North American Computational Linguistics Open Competition. I worked with faculty from universities all over the world to write computational linguistics puzzles for middle and high school students who, frankly, were much smarter than me if they could solve all of them!

Bizarrely enough, one of my linguistics professors seeded the idea of becoming a lawyer.

He said, “if you like analysing language but want to make a lot of money from it, you should try being a corporate lawyer.”

At the time, I didn’t really know what a corporate lawyer was, but I thought I’d look into it.

Needless to say, he was right about the money, but not so much about the analysing language, or at least not in the sense I enjoyed when studying linguistics.

So did you finish up your undergrad and do a JD?

Yes, I ended up going to Harvard Law School for my JD. In the meantime, I was also an LSAT instructor as well: the LSAT is the entrance test that you take in the US to go to law school.

While I was in law school, it was again, kind of an interesting path. I didn’t have much of a concept of what different jobs were out there within law.

In American law schools, or at least Harvard and similar, during your first summer you can do legal work pro bono, and the university gives you a stipend to do that throughout the summer. Into your second year, it’s all about getting internships at a Big Law firm.

I did something a little different for my first-year stint. I worked at the European Bank for Reconstruction Development (EBRD) in London.

That must have been quite an exciting and unusual experience for a student?

It totally was! It was really awesome. It’s a great organisation. I got to work with a great team of people, and it was my first time living abroad. I really liked it.

London in the summer is loads of fun, though everyone did tell me, that you shouldn’t ever make a decision about moving to London if you’ve only seen it in the summer because the winters are awfully long, grey and wet, but I thought, you know, “how bad could it be?”.

It was that opportunity that got me excited about London and why I eventually moved to London.

After the EBRD, before the start of year two of my JD, I did my interviews for internships with Big Law firms.

I liked London so much I decided to take an internship with one of the UK firms that toured the Harvard campus. That firm was A&O.

I got to spend my second summer working in the international capital markets team in London and in Moscow with A&O. I am a native Russian speaker, I had a connection to Moscow.

I loved the experience, and during my time there I got to do some derivatives work, which I thought was really cool.

I also did a lot of prospectus review work, your regular ECM (equity capital markets) and DCM (debt capital markets) relating to Rule 144A review work and so on.

Unfortunately, I didn’t find that particularly engaging, but it was useful as it made it a lot clearer to me what the job would be like, and which area of law I thought might suit me best.

Meanwhile a friend of mine had gone to the private equity M&A team at Kirkland & Ellis in London and was raving about his experiences there. Now he’s a partner there, and he continues to love it.

I started to think maybe there were other avenues within law I’d like to explore.

And did you start angling toward that track?

Not immediately. I actually took a gap year. Being a good entrepreneur, I was always looking for various ways to game the system to my benefit.

This was particularly crucial for me. Being at Harvard with its large American school fees and my humble beginnings, I had to take on a ton of debt every year to attend, but they also have financial aid, which was pretty generous in my case.

So, I was getting a lot of financial aid, but there were quite few catches. One of which is that for any Big Law internship in your second year you will generally be paid a first year associate salary for the summer, which is great. But this reduces dollar for dollar any financial aid you receive in the following year.

I sense a loophole coming. What did you figure out?

Well, the financial aid programme only accounts for your immediately previous summer and any earnings made during that period. I started thinking… “what if I took a gap year after my internships?”

I asked the financial aid folk about this and they said, “if you did that, we wouldn’t consider the internship earnings from the year before; we only account for the immediately previous summer”.

So that was my greenlight to take a gap year. I took my summer associate money and went on a world tour, which was awesome.

That’s very clever. Where did you go on the trip? What were the highlights?

I went to visited something like 40 countries in Europe, Africa and the Middle East. But the highlight was my time in East Africa, and especially the month I spent in the Democratic Republic of the Congo, trying to cross the country by land and riverboats.

The riverboats I took were crazy amalgamations of humans, chickens, monkeys and all sorts of goods. It was eye-opening to someone who had never travelled much beyond the US and London.

Floating down the Congo River

At the end of the summer, I did a non-profit internship in Tajikistan, which was very far away from anything I’d experienced before or since.

So yeah, it was a really fun year. And a smart decision financially.

And where did you end up after returning from your travels?

I went back to law school and finished up my JD.

My aforementioned friend introduced me to the partners at Kirkland & Ellis, and I got a job there, flying out to London very shortly thereafter to be a private equity M&A associate, where I stayed for about three and a half years, including a secondment to New York.

Given your mixed interests, did you get to do anything unusual at K&E?

At Harvard I’d cross-registered for various courses in advanced finance, statistics, linear regression and similar. That, plus my background in chemical engineering and general interest in finance meant I ended up doing two levels of the CFA exams whilst I was at K&E, which is a qualification that asset managers and similar pick up.

I naturally got really good with Excel, which unsurprisingly — or maybe surprisingly depending on how you look at it — made me valuable at K&E.

I was the guy who could understand how to read, and build, financial models that pertained to our PE clients. And I could also translate these into legal docs and vice versa.

Most lawyers will only understand the basics of Excel at best, so I was an unusual breed to my peers.

It was a great experience being invited into a partner’s office, them stepping out of the chair and inviting you to sit down and analyse their client’s spreadsheet and explain it to the senior lawyers on the deal.

I think there’s something junior lawyers could learn from that.

My advice is to invest in wider skills and experiences beyond your legal training. I know that’s harder in the UK where education, including legal education, is more linear, but definitely try to invest in other skills that make you stand out from the crowd and add some edge to your value.

Everyone in Big Law has legal skills. Try and find your unique selling point, some other skills or experience that make you stand out above the crowd. Sometimes it’s being good at stuff other folks avoid or aren’t good at, like Excel!

You’re a rare breed, a lawyer who can code, and rarer still, has actually built an enterprise application. How did you get into computer programming?

I studied computer programming back in my early days of college and university, especially when I was studying engineering and working as a computational linguistics research assistant.

However, I really got into computer programming around the time I got interested in crypto, sometime around 2017.

As I learnt more about crypto I came across the phrase “smart contract”, which sent me down a massive rabbit hole of resources explaining how code is law and that coded contracts would supersede regular contracts and so on.

That led me into learning how to write smart contracts in Ethereum.

And then from that I got drawn into computer science, i.e. the science behind how a computer actually works at a much lower level, but also how algorithms are designed and optimised.

I got really nerdy and was spending a lot of my free time learning, watching lectures, reading books, experimenting with algorithms and so on while I’ve continued to work as a corporate lawyer.

Did this influence how you thought about your job as a lawyer?

It absolutely did. I started to notice how my jobs to be done as a lawyer and my jobs to be done as an open source programmer overlapped.

For instance, in either case I was usually trying to take some complex system, whether it was a software or a deal, and I was trying to capture it in writing, whether that was source code or human language. In many ways, contracts are the operating system for how a commercial relationship is meant to behave and be governed.

But, as a software developer, I had access to these principles, paradigms and tools that made my job so much simpler, faster, and easier when dealing with, to be frank, a lot greater complexity than I was dealing with in my legal work.

By comparison, as a lawyer I’d be sitting there typing stuff into Microsoft Word, word by word. I would often have to open two or more documents and almost always make the same — or very similar — change multiple times within a document and often also across several documents. This was both when creating documents but also when updating or correcting them throughout a deal.

But the only way to do these things in my legal role was to open these documents, wait five minutes while they are opening, and manually make each change multiple times one by one by one… It took forever, was really dull work, you never learn much from this sort of thing either.

As dull as it was, this was the starting point for an idea combining my legal and software knowledge.

Partly it was also borne out of the idea in software that you don’t repeat yourself, and instead keep your code DRY.

By this I mean that when you write software you are always looking for ways to reduce repetition, replacing it with abstractions or using data normalisation to avoid redundancies. In other words, not working the way most lawyers work.

And is this how you started to generate the idea for what later becomes Office & Dragons?

Yes! I kept thinking:

“Surely there is a better way; it’s just data being transferred back and forth, and that means there must be a cleverer process and a way to tell my computer to carry out that process on my behalf so I don’t spend my evenings and weekend essentially doing legal data entry type tasks.”

So, on my weekends and evenings, I started hacking away at the problem.

The day I got things working was extremely cathartic.

I ran some dummy docs through the prototype that were representative of my day-to-day legal docs and tasks and… it worked!

It was such a great feeling.

Coding is very rewarding like that. When you solve a problem, you feel awesome. Coding is also very unforgiving — sometimes it’s crazy hard to unpick why something refuses to work the way you intended, or totally fails.

But once I solved my problem and found a way to automate these types of boring legal tasks, I was super excited, but also felt a little dumb that my colleagues and I — and peers elsewhere to be fair — were wasting so much time doing this type of thing manually, and that it was just the accepted way of working. Nobody was curious or challenging the status quo.

To be clear, I don’t think it’s necessarily deliberate, but simply ignorance borne out of the fact this type of thinking and experience is in no way part of legal education and training, both at university and on the job. Hopefully someday it will be!

This is when it started to feel like my germ of an idea had legs; that I’d like to transform what I’d built into an actual product I could show even my most tech-phobic colleagues, and get them excited about what it could do.

It’s worth bearing in mind that at this point I was the guy in the office who would come into your office, unsolicited, and talk to you about how smart contracts are going to replace regular contracts and how you should learn to code etc… and everyone probably found me very annoying!

In all seriousness though, I wanted those same people to look at what I’d built and say, “wow this is obviously a way better way of working that’s easy, quick and saves me a ton of time and delivers great client value”.

That’s when I decided I should make a UI, because at the time, what later became Office & Dragons, was a command line tool.

How did that go? How did you coin the name?

Well, at first it was still command line based but took on a wizard driven approach where it would ask if you wanted to do A or B and you could answer “yes” or “no” to drive the process forward in whatever direction you desired.

I didn’t want to call it a “wizard” per se, but I liked the fantasy emphasis of the word “wizard” and decided I’d call it a “dragon”, a dragon guided app. The dragon got me thinking “Dungeons & Dragons”, and when I was up late doing the kind of work the app was made to automate, the office felt like my dungeon, so I coined the name, “Office & Dragons.”

The prototype played heavy metal chiptunes while you conquered your docs

How did things develop from there?

It was gradual.

At first, I was hacking away on weekends and evenings when I wasn’t worn out from my day job as a lawyer. Once I got a good working prototype together, I started to think more seriously about the fact I knew several colleagues within K&E doing the same sorts of tasks manually that could probably benefit from what I’d built.

And when I got to that point in my thought process, I got to thinking: which other lawyers might use it?

As such, I reached out to folks at other firms and local counsel firms I’d worked with on K&E deals, showed them what I’d built and asked them whether they would use it on their work and where it would fit, if anywhere, in their process.

Very quickly I got a sense of the threshold features Office & Dragons would need to make the grade for large law firms.

Time and time again, the suggestion was that Office & Dragons needed to integrate seamlessly with their document management systems (DMS), which for most firms I surveyed was iManage.

I heard that enough times that I decided that was what I needed to do, to add that integration… but how? And where to find the information?

To find that out I went to the iManage site and found they had a partner program. That program has a contact form and so I figured, “what the hell, why not?”.

I filled it in and sent them a little email, pretending Office & Dragons was already a business, and enquiring about becoming a partner and integrating with their platform.

I wasn’t really expecting much, but I thought, “don’t ask, don’t get!”

Luckily for me, and somewhat shockingly, they replied a few days later! They asked me to put together a datasheet on the product explaining what it was, what it did, how it would integrate and so on and the value it provided.

At the time I still hadn’t created a graphical user interface, or any front-end for a non-technical user. Everything was still done via a simple command line interface.

iManage were actually interested, to my surprise, and said they hadn’t seen something like this before but that they liked what they saw and thought it very useful.

And thankfully they approved Office & Dragons as an integration partner.

I was even more shocked by this point — I totally wasn’t expecting that response. But it was a massive proof point for me, being accepted into iManage’s partner program, which meant a lot as iManage is one of the biggest legaltech players and used by most law firms and large legal teams.

We’ve come a long way in UI & UX

Did you know much about the legaltech market before this point?

I did not! I thought there wasn’t any legaltech at the time. That sounds bizarre, because obviously I was using a lot of tech to do my legal job, but I just didn’t equate the two necessarily, nor really appreciate some of the legal specific tools I just took for granted.

I thought I was the only lawyer who wrote software. Obviously, we hadn’t met yet! Nor had I met the other folks who I’ve since gotten to know who are lawyer coders or even career changers from law to development and similar.

I got curious around this time and one day I started Googling things like “lawyers who code”.

Coincidentally, LegalGeek had started a series on that very subject, and I came across their blog series and started to discover there were more people like me who were lawyer coders, of which you were one.

That led me to discover LegalGeek and its events, which I was excited to attend. Luckily, they offered free start-up tickets. I emailed them, pitched my soon to be start-up and they gave me free tickets.

As part of that I was invited to spend a week working at Barclays Eagle Labs, the legaltech incubator of Barclays Bank.

I decided to stop by during the week LegalGeek was running and was surprised to see so many major law firms — including Magic Circle, Silver Circle, and a handful of US Big Law firms — backing the initiative, and the number and variety of start-ups and scale-ups being incubated.

My initial impression was also that “hmm, maybe these are more scale-ups and I am way too small right now,” but I got talking to Shara Gibbons, LawTech Manager at Barclays Eagle Labs, and she encouraged me to apply anyway and see if I could become a resident start-up.

A short while later I was invited to pitch Office & Dragons to the Eagle Labs partners — all innovation, legaltech and ops folks from Barclays and the partner law firms, plus others from the Law Society and LegalGeek.

And they said “yes.” I got invited to become a full resident of the Eagle Lab. It was a little nerve wracking but worth it.

Around that same time, I also had the chance to show K&E’s CIO Office & Dragons when he was visiting London and he responded very positively to it, which was a big confidence boost.

Celebrating the day we moved into our own office in the Barclays Eagle Lab

So was it these various proof points — the iManage integration partner approval, being accepted into Barclays Eagle Lab, positive feedback on the product from various lawyers and K&E’s CIO — that gave you the confidence to consider making a go of Office & Dragons full time?

Yes, it was that combination of proof points. After that, I decided to go into my boss’s office and say, “well, it’s been a pleasure, but, remember that weird thing I showed you six months ago… well, I’ve decided to leave and launch it as a start-up”.

How did K&E react to your decision to leave and start a tech business?

They were very respectful and supportive of my decision. I think they were also a little concerned that I didn’t jump off into the deep end and make a bad decision.

The senior folks I worked with spent time with me asking me, very kindly, “are you really sure? Talk to me before you hand in your resignation letter.”

It’s quite an unusual path to take for a Big Law lawyer, so I think they wanted to be sure I’d thought it through, and if they could, help me out.

But in the end my mind was made up and they were sad to see me go but understood why I wanted to take a run at launching my own start-up.

Rather flatteringly a few of the partners said, “if I was going to bet on anyone to succeed at launching a legaltech start-up, I’d bet on you”, which was very kind.

And being a little cheeky, I did ask those partners whether they’d personally invest in the company, which they did, and for which I am very grateful!

Had you been thinking about leaving the law before then?

Good question. Leaving the law to start Office & Dragons was part of a broader equation, I think.

For some time, I had not seen myself as a long-term private equity M&A lawyer, or a lawyer in general. I increasingly felt I was being pulled in the direction of doing other non-legal stuff.

As I said, there is this meme that you go to law school and work at a BigLaw firm for a couple of years to pay down your student debt and then go onto your true calling. To some extent that had always resonated with me even though I knew it wasn’t often how people’s plans panned out. But I knew I wanted to do other stuff.

At the same time, I wasn’t certain what that “other stuff” was.

I think this is a common dilemma for lawyers who want to leave the law but are stuck as to what else they’d do instead, especially because you invest a ton of time and money along this long road to becoming a lawyer. It becomes part of your identity. Legal skills and experience can either be, or feel like they are, very niche and not very transferable. Depending on what you do, how you do it and how you present your legal skills, this isn’t necessarily true, but it’s a pervasive mindset. It can be limiting, at least in your mind.

Speaking to the UCL Legal Hackers club about moving from Law to LawTech

For me, I didn’t know if that “other stuff” was launching a start-up. At the time I really didn’t know much about start-ups. To me they were people in a garage making stuff and eventually, if you are lucky, people give you money and it either succeeds or fails.

I was also mulling over the idea of doing a computer science degree given how much I enjoyed coding and computer science in my spare time. I really do enjoy it and I thought I could be a professor or something.

And then I was also thinking about venture capital, possibly segueing there by becoming a venture capital lawyer.

I should add these thought processes were typical lawyer thinking, excessive de-risking, which I think gets in our way a lot of the time.

My thought process was essentially, “well, before I go and be a startup guy, I guess I should be a startup lawyer because then I’ll learn about startups. And before I launch a tech company, I should probably get a computer science degree… etc.”

What put me on the right track was one of my K&E friends.

He’s direct and says to me:

“Hey Sam, do you actually want to do those things, or do you just think you should do them? Do you have enough money to launch a start-up and survive for six months if that’s what you really want to do?”

And he was right. I started to rationalise the downside. I said to myself and to him, “worst comes to worst and Office & Dragons fails within 6 months, I could get a new job and survive for some time if I keep my expenses in check”.

So he said, “well, why don’t you do just that?”.

That was the nudge I needed.

Was Office & Dragons the idea for your jump into start-ups or one of a few you had in the works?

Not a lot of people know this, but I was torn between Office & Dragons and another idea I was working on in the crypto space.

That idea was a cryptocurrency driven by the value of user generated content. I even wrote a whitepaper about the idea, which I felt was very cool.

But it was Office & Dragons that had gotten the various proof points soonest, and most significantly. That was what tipped me toward Office & Dragons and not my crypto idea.

Before you got to that point, you must have been living a sort of double life: lawyering by day and building out Office & Dragons on the side in your free evenings and weekends? How did you juggle the two?

Office & Dragons was a hobby project for a while, and of course that meant my day job at K&E came first.

However, as a transactional lawyer, work comes in peaks and troughs. It’s feast or famine. Some weeks you work all-nighters and weekends. Other weeks you have very little to do.

Early in my career, the down periods were much needed respite from the busy periods. I would just want to shut off my brain, play PlayStation, watch Netflix, and generally pretend I didn’t exist and that I wasn’t going to be utterly slammed again any time soon.

And for a time that was fine. But then I realised it was avoidant behaviour and, to be honest, not a great use of my downtime when I had all these other ideas on the go.

As such, I started to actively try and turn my attention toward Office & Dragons whenever I got downtime from K&E.

Just on that, K&E does have a certain reputation for being a tough place to work, especially in terms of billable hours and work / life balance. I’m not going to say that it’s not deserved at all, but I will say that I worked with some really wonderful people and overall, it was a very positive thing for my career and a very positive experience, even if it was tough!

For me, the turning point was that I started to realise that I wasn’t fulfilled simply by lawyering. I was finding the time I spent studying coding and computer science around work, often late into the night during evenings and weekends, more invigorating. I started to look for more opportunities to maximise those activities around work.

What sort of resources were you using, or would you recommend to anyone generally interested in computer science or coding?

Too many things probably!

I think it depends if you want to learn coding, or if you want to learn computer science. The two are obviously related, but also quite different.

For me, I started with coding because I wanted to build things and, in particular, learn how to build smart contracts.

To do so I used medium.com a lot. It’s a great resource for explainers and how-to tutorials for a variety of technical topics, but also any topic really. Very quickly when studying Ethereum I got to understand that the language to implement Ehtereum smart contracts, Solidity, is based on a JavaScript type paradigm, so I quickly got into learning JavaScript.

My thinking was that I should learn this older language — JavaScript — which forms the basis of Solidity. One would help me better understand the other.

Also, JavaScript powers the web so it made sense from that point of view, i.e. to better understand the web and how to write internet enabled applications.

On a practical level, given JavaScript is a more established language, it is naturally much better supported in terms of documentation, tutorials, blogs and so on than Solidity, which is much newer and less well supported, albeit the Solidity community is growing all the time.

For JavaScript, I’d recommend Eloquent JavaScript, which is an interactive book filled with coding challenges that you can try to solve, and they have solutions that you can compare yours to theirs.

Another resource that is popular, which I’ve used a little but don’t personally like too much, is www.freecodecamp.com. It’s quite easy at first and is really a long list of small coding exercises. In my opinion it gets repetitive quite quickly, and I don’t personally learn by repetition but instead prefer to learn by building things.

Or more precisely, I learn by failing.

I find the best way to learn coding is to fail at trying to build something. Eventually you go from bashing your head against a wall in frustration to suddenly having this “a-ha” moment where you figure out or find a solution and suddenly things fall into place.

That was what I enjoyed with Eloquent JavaScript. You take a crack at a problem, and even if you get totally stuck and cannot solve the problem, having then seen the answer it’s suddenly much clearer why your solution failed, and you develop a much better intuition and understanding for the next problem.

One word of caution, I’ve since been told — and realised — Eloquent JavaScript is really an intermediate resource vs say FreeCodeCamp, which is more of a beginner resource.

On the computer science side of things, as I said earlier, I was really into philosophy in my younger years, and as such got into logic which obviously has a big role in computer science.

My favourite book by far in this vein is called The Little Schemer.

It’s this question-and-answer style puzzle book. Each page is split in half and there’s questions on one half; answers on the other half.

It’s quite clever. It subtly introduces computer science concepts as an extension of arithmetic and algebra; things that everyone studies in school.

It would be good for lawyers because it’s similar in style to the Socratic method via which most lawyers are taught.

Once you’ve read The Little Schemer, you should read The Structure and Interpretation of Computer Programs or watch the lectures on YouTube.

The YouTube lectures are by the MIT professors who taught what used to be MIT’s intro to computer science course back in the 80s, and this is the textbook they wrote for this course.

Be warned, it’s now considered quite advanced, so not a beginner resource, but well worth the effort to learn if you are really keen! The book really teaches you to think about computer programs and understand how they actually work inside of a machine, which is really fascinating.

Is there anything specific a lawyer or other non-technical person could focus their energies on when learning to code?

Yes, if you learn programming, you could very usefully learn how to build little scripts to automate your everyday work.

More generally, learning computer science or any engineering discipline will teach you how to think about a problem systematically and solve it in a repeatable, efficient, and scalable way. That is hugely valuable because this is totally missing from law school and most legal organisations.

You are not taught how to solve problems at scale. You usually solve a specific problem for a specific client, and are guided by the way clients present you information. You are not really taught how to think about spotting patterns between clients and transactions that can be turned into repeatable, scalable processes, products or services… or at least processes, products and services scalable beyond simply throwing more bodies at the problem, and generally treating all things to all people as 100% bespoke.

Unfortunately, the result is that lawyers tend to overlook opportunities for standardisation, augmentation, or automation of process, which is sometimes because of an “all or nothing” mentality that everything must be automated or it simply isn’t worth the effort.

In most cases, that’s not true. Automating parts of a process can deliver outsize value. But it requires a different mindset.

Any sort of engineering discipline will teach you these missing skills. And that is what got me to think about my own work, more than anything in a different way.

I agree. As someone who learnt to code and picked up pockets of computer science later in life whilst being a lawyer it definitely opens your mind to an entirely different way of thinking.

Sometimes it can be uncomfortable because it challenges a lot about the way lawyers work. This can make those modes of working seem needlessly inefficient, and that’s a deflating realisation. It’s also hard to convince your peers to work and think in that way if they don’t possess the mental models you pick up from engineering disciplines.

Do you think there is a difference between the learning curve for “learning to code”, and being able to get to a point where you can build an end-to-end application? I sometimes think the question of whether lawyers should learn to code conflates this distinction without understanding the difference.

Oh yeah, totally. Learning to code is one thing; learning to build software is another.

Going from zero to building software that works is a long, long journey. Even longer if you are talking about building scalable enterprise grade software with integrations and bulletproof cybersecurity.

It’s not a weekend course, or a few hours a week here and there and hey presto, you have an app that ticks all those boxes.

I distinctly remember learning a ton, feeling great and getting so many ideas flowing. Then I’d sit down, open my favourite IDE (integrated development environment) to start writing code, create my source files, name them something cool and then…

… realise, “where on earth do I go from here?”.

For a long time there it felt like there was a huge gulf between what I knew and what I wanted to do, and needed to know in order to deliver on those ideas.

The rollercoaster of confidence relative to competence

If you keep plugging away, filling the gaps in your knowledge and going layers and layers deeper, eventually you get closer to something that feels more manageable and actionable.

But you often still get stuck, hit a wall and in that scenario you think it might be better to try and find other people’s code or a tutorial that does something pretty close to what you’re after, and then really get into the weeds of how that works and, crucially, how you can adapt it (or not) to what you’re trying to achieve.

And this is before you even get to good user experience and user interface, which is an entirely separate, albeit related, and significant body of work to master. It looks easy, and we take great UX and UI for granted, but it’s tough to make stuff easy and enjoyable to use.

It’s not just pretty colours!

What you don’t want to do, and what people always do, is make something that only makes sense to them. Understanding what makes good UI and UX great is worth your time.

The elephant in the room before all of that is this: are you solving a problem people care about? Do they care enough about it to pay you to solve it? How can you find this out as cheaply and thoroughly as possible?

To do this you need to get talking to users, understanding what they do, where they do it, how they do it, with whom they do it, why they do it and a whole myriad of often unsaid drivers and context behind all of that. That will give you a lot of clues, and help you build a product that fits a need, or at least improve the probability of that happening. You should then test that product with users early and often to ensure it delivers.

In any one of these areas there are so many layers and it depends how many layers deep you need to get. Sometimes it’s hard to know how deep to go.

As with anything, it’s about taking stock of what you already know, what you don’t yet know that you might need, and weighing that up against what are you willing and able to learn given other constraints like free time and so on.

One of the reasons Office & Dragons didn’t have a UI for a long time was that I simply hadn’t learnt how to build UIs. Most of my programming was back-end and scripting. Books that I mentioned like Eloquent JavaScript are more about functions and algorithms than how to make a UI with buttons.

Because of that, I started to read about things like event handling and UI systems. At the time, I decided these were really complicated and that I’d park that area until it felt necessary, instead preferring to build a command line tool initially to test my idea because that was what I was comfortable doing with the knowledge I had.

Of course, I had to learn a ton of other stuff along the way, such as manipulating Microsoft Office files and file system storage.

It’s an iterative kind of process: eventually you hit the point where you realise, okay, there’s some functionality here, but there’s no escaping that no-one’s going to use it as a command line thing — I need a UI.

At that point, I knew enough to make the app achieve what I needed it to achieve and couldn’t really learn much more to take things forward, except to then skill up on UIs and build one for the app.

At any point did you start thinking about bringing others into the process, e.g. to help with the front-end or similar that sat outside your core expertise?

Yes, I did start to think about when that point would come. If you’re doing everything yourself, as I was, because it’s your project, after a while, things can balloon. You figure, “maybe I need a hand”, at least to divide and conquer the tasks more quickly without also having to learn how to do the tasks on the fly.

I think delegating and teamwork is hard for lawyers. This is a controversial opinion, but I don’t think we as lawyers work in teams. Or not in the sense of teamwork understood and practiced outside of law.

I see teams in non-legal organisations like a pack of dogs, everyone is pulling in the same direction and being led toward a goal and sharing in the spoils.

Lawyers are maybe more like a team of cats. We are solitary and proud, and I think barring exceptional circumstances we always try to solve problems ourselves before leaning on others for help.

It seems to work fine for legal organisations, but it isn’t how to run a company. Of course I can play nice with others, be a team player. Of course I can do that.

It’s more a weird pride thing, I think. An acceptance that there are things I don’t know how to do, that I’m not going to learn to do, and that I’m not going to be good at doing them, and instead, I am going to rely on other experts to do those things for me and entrust their skill and knowledge to that task.

I think this is a hurdle for lawyers to overcome when switching into a business role, or leading a company, and perhaps all the more if that company is also your pride and joy.

But getting over that is great. We’ve built a fantastic team at Office & Dragons, all of whom are way more skilled and knowledgeable about the stuff they do than I am, or I’m ever going to be.

I will say my job as the CEO at an early stage startup is to usually do everything for the first time, usually because we don’t have a person for that thing. I do that thing for the first time, figure out if we need it, how hard it was, and how we might find someone expert in it to do it better than me and take it from there to something really great.

How has your legal career, helped or not with starting and running Office & Dragons?

Not to be pessimistic, but… there are certainly ways it has not helped, which definitely stand out in my mind because they were really big struggles, and to be honest, also surprises!

I tend to find that the things that help you aren’t as noticeable as the things that stand in your way.

For instance, lawyer skills focus you on the minutiae and spotting differences where other people can’t find any and wanting to be 100% sure about this or that. These skills don’t lend themselves to start-ups.

As my earlier story about spending the better part of my gap year in the Congo evokes, I wasn’t a risk averse person prior to becoming a lawyer. In fact that was probably the opposite! I was pretty risk-seeking.

I loved to play poker. Absolutely loved it. One thing that happened to me when I started my legal career, maybe as soon as one year into it, I became horrible at poker and I did not enjoy it at all anymore because of the ingrained risk aversion I’d developed through lawyering.

It got to the point where I would not want to play any hands because I just couldn’t do it without certainty of victory. I couldn’t bluff because I just didn’t want to play those hands full stop. I wanted the certainty that I would win, which with a bluff you necessarily don’t have. It’s never certain.

As a lawyer, if your client says, “should we do X or Y?”, you need to be as precise as you can be and say:

“If you do X there’s an 80% chance of this and a 20% chance of that. Or you can do Y, but we don’t recommend you do Y because although 95% of the time the result is fine, 5% of the time it’s bad and might result in some big sum of taxes or similar.”

It’s hard switching gears, and I say that as someone who was a risk taker and became much less so the more lawyering I did. Some lawyers are naturally risk averse. That’s why they entered the profession, but that wasn’t me, I was a risk taker and I still find it hard turning down my trained risk aversion.

When you’re running a start-up you’re faced with making many decisions. As a lawyer it’s easy to fall into the trap of analysis paralysis.

I did this a lot at the start.

I literally spent days deliberating over where to incorporate Office & Dragons, whether in the UK or the USA. I tried to research the tax law in various jurisdictions. I tried to talk to specialists. I tried to map out my possibilities for tax gains and losses in different setups. It was a huge rabbit hole that stopped me making real progress. I was telling people who wanted to invest “sorry, I need to finalize the incorporation and tax structure”.

That’s just one example, but this would happen repeatedly with every decision or enquiry, no matter how unimportant it was in the grand scheme of things.

Anyways, many months of being like this went by. I became more and more frustrated, exasperated to be honest, and just decided that I need to make decisions with imperfect information and live with it if I wanted to make a go of running a start-up.

Have you managed to improve?

Yes, I’ve gotten a lot better at this, partly through experience and just doing it. I don’t find myself sweating those things anymore.

The challenge is that as a lawyer you don’t get to make decisions one way or another, at least not in the substantive sense of this will make or break something. More often you are advising a client on the matrix of decisions they wish to make and will make, not your own decisions, if that makes sense.

On the positive side, I will say that being a lawyer makes you build confidence at presenting, speaking and generally asserting an opinion with conviction that is hopefully persuasive.

That’s very important, whether you’re raising funding or you’re talking to a prospective customer. You need to win them over and present a clear value proposition, often quickly.

It’s all the more important because when you’re starting you have to back yourself. You’re just this one person and you made this thing and aren’t yet maybe a real company so you’re absolutely going to have imposter syndrome. You’ve got no track record. You’ve never done this before. Who are you to know or say anything? Why should anyone return your email, call or listen?

These are the scripts that can play in your mind.

It’s difficult to work around these generally. It does get easier I think, and I think is made easier if you have been a lawyer of some sort, particularly perhaps a litigator where there is even greater emphasis on communication.

On communication, another lawyer habit I’ve had trouble shaking is the time I spend on emails. As a lawyer you are hyper vigilant about what you do and don’t say in email and how you say it and who is copied etc because getting that wrong can have disastrous consequences for you, your client, the firm and so on. I still disproportionately agonize over emails, knowing full well I should be more proportionate in how I spend my focus. I’m making a conscious effort to improve this!

What do you think has been the most surprising and least surprising since you flipped over from being a corporate lawyer to running a startup?

I work way more than I did as a lawyer, which I totally did not expect.

Believe it or not, doing cross border Luxembourg-domiciled private equity transactions translates 0% to trying to figure out your own startup legal documents. As it turns out, the standard UK startup seed investment documents are alien to me. I would look for my Luxembourg topco and just not see it!

So yup, that was surprising, that I need to do all these legal things I thought that I could do on my own, yet in fact couldn’t do. I simply didn’t have the experience: despite being a corporate lawyer. It’s surprising how niche you become as a lawyer even very early into your career and how much legal stuff you don’t know.

Least surprising is that running a start-up is extremely satisfying.

I was always unsatisfied as a lawyer, and I hoped that launching a start-up — being the principal in a commercial situation not the advisor — would scratch that itch, and plug that need, which it has.

That said, it’s definitely a lot harder than being a lawyer. Obviously, the pay is way worse, that’s for sure, and hopefully that improves. But right now, I wouldn’t want to do anything else. I really like it: the dynamism, the decision-making, building a team. All that good stuff.

For anyone interested in working in legaltech or similar, what skills and experiences do you think that they should be seeking to acquire, how they might find them, where they might find them with who they might need to connect?

That’s a broad question and it’s probably hard to give a concrete or satisfying answer. I’ll do my best but open with the classic legal response: “it depends.”

Concretely, it depends on what you’d like to do within legaltech.

You did this really great article on this point, about non-legal tech, the idea of fully exploring general tech and its application to legal business problems.

That goes to my ethos, that legal as a field, and legaltech as just another flavour of tech, and lawyers as knowledge workers are, in each case, not very special categories — no offence!

A legaltech company isn’t very different from a tech company. Legaltech software isn’t very different from general software.

The challenges faced by the legal profession are no different from those affecting banking, accounting, or any other knowledge discipline. To be honest, they’re not necessarily that different from stuff in marketing or HR, which to most lawyers would seem a silly comparison to make, but it’s true in my opinion.

Take away the domain and a lot of the jobs to be done are pretty similar when you get back to first principles.

This is pivotal when thinking about software as a solution to those challenges. It’s all the same broadly speaking.

In terms of how this understanding might help people, I’d say it should encourage you to look beyond legaltech resources.

If you limit your knowledge about tech to only legaltech, you’re missing out on a lot of really good stuff and often more mature thinking elsewhere, or simply missing out on other people’s solutions to more or less identical problems, which might save you reinventing the wheel as, your article pointed out.

I’d also say read around tech topics.

A specific example might be learning about the means for process improvement, the tools and frameworks etc. This stuff is well trod outside of legal and only quite recently seeing wider application in legal. Instead of focusing on legal specific resources, Google process improvement generally and find case studies, explanations, and examples from outside of legal. The same goes for product management and design. If you can find a non-legal resource it will likely be more in-depth and time tested, and may highlight how to do something you need to solve and save you reinventing the wheel by shoehorning these ideas into legal ways of thinking.

That said, there are upsides to getting this sort of information from legaltech or legal specific examples. These nuggets however will be centred around challenges specific to legal, particularly some of the esoteric adoption challenges faced by law such as the billable hour model that butt up against the typical time savings and efficiency effects of good tech sat atop some refined people and process. All that to say, this — billable hours and adoption etc — are still really about incentives and how they enable or inhibit behaviour change, which is a time tested and well researched topic applied to a huge extent outside of legal!

What advice would you give to individuals wanting to start a company of their own, whether it’s a legaltech company or any startup business?

Test the market. Do what I did relatively little of and talk to a lot more people than I did. I did a lot, but not enough in hindsight.

There’s tons of resources on how to have those conversations. Your objective is to figure out what it is that you can deliver that people want and will pay for.

I think you also need to decide what type of business you want to build and why.

For some folks they want to build a lifestyle business, i.e. one that supports their lifestyle or a particular lifestyle and aren’t too fussed about simply seeing how big they can grow it. What you need there is a relatively high certainty of guaranteed income, or at least a relatively certain and near-term road to getting there.

If you want to go after a ton of VC money and do the cliché “change the world” type venture, that is something else entirely. Going down that road requires a market size in the billions and those are difficult things to find, to prove and to build.

Be very critical with yourself as well. Not in a pessimistic way, but in a realistic and constructive way. Most people aren’t, especially I think when they’re building in their own domain.

When building for your own domain the two biggest traps are these:

One, that you overestimate the size of and value of the problem. Just because you had it, and it really sucked, doesn’t mean it sucked for everyone or perhaps didn’t suck as much for everyone as it did for you. You need to find out how much the problem sucks for everyone, and how much value they place on it being solved by you.

Two, and tied to the above, how much are people willing to change their behaviour in order to solve the problem even if it really sucks. For instance, if you are trying to get a bunch of banks to work together and totally change their way of working, that is going to be tough whether or not the problem is one they all hate and would love to solve. The ease (or not) of changing behaviour needs to be outweighed by the value of solving that problem, often quite significantly so.

If you can solve a problem that is really painful and solve it with as little friction or behavioural change as possible then you are onto a winner. This is why Google search dominated. It was easy and 10x better than incumbents. Switching was a no brainer.

Another issue is trying to average out the requirements for the product. It’s very easy to build something that, as the user, I would like and understand very easily, e.g. that the button looks like this and sits over there and is this colour and has that label. The easiest way to break the assumption that your design decision makes sense to all users is to go and ask two users what they think.

Inevitably you will find that both have different opinions from each other, and they’re both different from yours.

You need to have these conversations, and keep having them otherwise you will build the wrong thing or solve the right problem in the wrong way, which is perhaps worse than building the wrong thing or solving the wrong problem.

What do you know now that you wished you knew earlier in your career?

Do the thing you want to do, do it earlier, be a little less safe, and don’t necessarily spend as much time building up to it or putting obstacles in your own way.

As I said earlier, don’t feel that “before I do this I have to do this other thing and this other thing and so on” feeling.

Ask yourself whether that’s really true, just a delaying tactic, or excessive de-risking. If you don’t, you may never get to where you truly want to be and take the chances you desire.

Take more risks. Don’t be reckless, but take some risks.

Don’t catastrophise about what if it doesn’t work out. Often, even if it doesn’t, you gain skills that lead to other things.

Tunji William’s career journey featured in one of your earlier profiles is really awesome.

He’s a good example of someone who took his lawyer skills, took some risks and put it all on the line running a tech start-up, which unfortunately didn’t work out, but after went on to work at Litera — a really large tech company — leading ways to attract, grow and maintain their customers and has folded these skills and experiences into his new role leading a really cool and different social enterprise.

You’ll land on your feet most of the time. It’s like they say, shoot for the moon, cause even if you miss you’ll land among the stars!

Wrapping up, do you recommend any books, podcasts or other media relevant to legaltech, startups, careers, anything that you’ve found influential for your career to date?

I definitely recommend Lawtomated. I think it’s a very legitimate resource, especially for folks that like the techier side. I like how you’re willing to take the extra step and lay out the techie side whilst striking a good balance. I don’t feel I’d be turned off or unable to follow if I didn’t have a technical background, but equally I get something extra from it because I do have that knowledge.

I will say that Nathan Corr at the University of Aberdeen is doing a fantastic job with their legaltech society. They put on some great events, real quality stuff.

Thinking again of students in mind, there is a blog called the Exploratory Journey by Ved Nathwani that has blossomed into something awesome. And I am not saying that because he also interviewed me! Ved has gone on to interview way more interesting people than me.

I do think that what Ved’s project teaches is the importance of network and not being afraid to put yourself out there. Ved is a high school student and is using LinkedIn to reach out to people and I’d imagine not everyone he messages responds or gives an interview, but over time, with enough tenacity you can — as he is doing — build something and in doing so, share some great knowledge.

I would also say that I often have people reach out to me on social, and I love helping out and giving advice where I can. So please feel free to reach out to me on LinkedIn or Twitter. I say that whether you are a law student, a non-law student, a lawyer or non-lawyer considering a career change or starting a business. I’d love to make myself a resource to you and help in any way I can!

In terms of books, and other blogs, I really like:

• Reforge. This is an amazing blog stuffed full of resources on growth hacking and many other cool business ideas. In particular there is this great article by Rahul Vohra, founder and CEO of Superhuman, an email productivity app that has grown like crazy. That article is about ways to measure product market-fit, using leading indicators and other techniques that they seem to have honed.
• First Round Review. This is a blog by the VC fund, First Round. They put out a blog that covers some excellent founders sharing practical and actionable knowledge for anyone in start-ups.
• Patrick McKenzie, who works at Stripe Atlas, has written a wealth of excellent material on SaaS pricing. This is a particularly detailed guide and well worth your time if you are interested in how to price SaaS. See also here for his essays.
• Aaron Dinnin who writes on medium.com and teaches entrepreneurship at Duke University. He’s a super nice guy. I reached out to him after reading his content and he was kind enough to meet. He writes about a lot of entrepreneurship ideas that I’ve not seen elsewhere.
• Saastr has a wealth of resources about SaaS businesses, how to build and run them. Jason Lemkin, who runs it, also shares lots of interesting observations about the SaaS market that get a good conversation going on twitter. Well worth a follow if you are keen on SaaS.
• Forentrepreneurs.com by David Skok has some amazing resources on unit economics, and how this breaks down. It’s a difficult topic, but one you have to understand when starting and running a business. His guidance — e.g. this article — on that subject is second to none from what I’ve read so far. The biggest problem for a lot of start-ups is that they don’t know their unit economics. His blog is a good way to understand these and be able to explain them to investors — very important!

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Originally published at lawtomated.