Why running a Tech Startup is like fighting MMA

Adrian Cartland
10 min readNov 29, 2019


Earlier this year I participated in my first MMA fight. I have been karate training for 25 years (3rd Degree Black Belt Goju Ryu) and have taken part in other martial arts (BJJ, wrestling) but this was, without a doubt, the hardest thing that I have done so far.

I have also been running a tech company that builds legal artificial intelligence (Ailira.com) for the last 4 years, alongside my law firm, and I was struck (pun intended) by a number of similarities in the experience.

I am not going to claim that I am a pro-fighter (I am not) or running a billion dollar company (I am not — yet). But I do think that the observations are pretty interesting.

It is Petrifying to take the Leap

Did you know that MMA cages lock from the outside?

Once that cage door closes you are locked in a 30ft space with a guy who wants to beat your head in, and the only way out is if one of you wins and the other loses. Even when you are training at your club it is much more nerve wracking being in a cage than sparring in a ring or on mats. When you fight you are there in front of your friends, family, teammates as the star attraction, just wearing some underwear and gloves, hoping to not embarrass yourself or your team (or get badly injured).

I have meditated for years, undertaken different types of sparring and competitions, and had enough real world encounters that I am not concerned with confrontations and challenges. As a lawyer I get to “do” confrontation on behalf of my clients for a living. But 2 days out from my fight I was unable to focus my mind, it was racing. Fortunately, my karate instructor (who has also spent time at a zen monastery) gave me some very sound advice.

He said, Imagine the absolute worst that could happen to you, and then accept that. Then you will be invincible.

So I imagined getting my limbs broken, terrible injuries, embarrassing failures, and then accepted that as a possible outcome. Once I accepted the worst outcome then there was nothing that could happen that I feared. I was so relaxed, and when I entered the cage I was so incredibly in the zone and mentally focused.

Entering the cage with a clear mind

My initial career ambition had been to be a tax lawyer at a mid-tier firm. I had worked my way through various the ups and downs of a legal career to that end (and boy can there be some bad experiences in law). I had a well paying job at a respected firm, with a great boss. My practice was growing and I was happy. (Yeah, being happy can be rare in law).

Then, I began to read about the future of law and came to the realisation that AI was an inevitability and that we were all at the cusp of a series of massive changes within the legal profession, both nationally & globally. I came to the realisation that I was going to have to pursue that change outside of the traditional law firm structure. So, that was that, I had to go in and tell my very kind boss that I was quitting a good job. Who quits a good job? I was shaking on the way to work it was that nerve wracking.

But once I had left it was a huge relief. I was now master of my own destiny. My resting heart rate literally dropped 20 points, even my body knew I was on the right path.

A step towards destiny: Ailira passes the Adelaide Uni Tax law exam

When you go, go

One of the concepts of Karate is ‘Fudoshin’ meaning ‘immovable mind’.

Meaning, when you do something, you entirely commit to it. A punch executed with Fudoshin will be one that is committed in its intent to hit the opponent, which will make it stronger and harder. Fudoshin is also a strategy in sparring i.e. To attack with fudoshin. When you decide to attack you fully commit to following through on it, because there is no weakness or hesitancy in the attack there is nothing for the opponent to exploit.

Another way of putting this is “when you go, go”. Therefore the attacker does not waste time with feints and distractions and half-attacks or fearful attacks. You make a decision to attack, and then see it through, whatever its consequences are. You either get ‘Ippon Issatsu’ (one strike, one kill) or you lose.

The pursuit of Ippon Issatsu through Fudoshin is why traditional karate matches (called ippon-shobu: one strike bout) between black belts will typically last less than 30 seconds. One side scores an ‘ippon’ and wins, or the other side does. Each commits to what they are doing.

Mae Geri: Committed front kick on opponent

This was uppermost in my mind when I entered the ring. I had told my MMA coach that my game plan was to end thefight within 30 seconds by knock out (he didn’t quite believe me). If it went longer than that then it would be a grappling match, which tends to go much slower (at least for my level of ability), and so the remainder of my strategy would be fighting to regain striking range where I could again try for Ippon Issatsu.

Watch the match for yourself below and see how my strategy panned out

A six second knockout is the equal fastest in Australian MMA ever

After some months of consideration I came to the realisation that it would be necessary to build legal AI outside of an existing firm structure for reasons explained here. At about that time, I was offered a mutually beneficial contract by my largest client that would reduce the legal fees they pay to a firm, and was larger than my existing salary. I could have just worked for them part time and earned more than my existing wage — the opportunity for a life of leisure!

However I also realised that I could use a contract retainer as an opportunity to underpin the cash flow for developing AI and giving me the time to work on fixing what is broken with the law. This was a once in a lifetime opportunity and meant that I would not have to seek external funding for development. So with 3 weeks notice I completely upended my career plan and launched my own tax law firm (also servicing my other clients) and began development of Ailira. I saw the opportunity to go, and I went, and will either succeed or fail, but I will not miss out.

I get to speak a lot about the future of law, professions and AI

Sometimes the world beats on you

Competitive martial arts is great for restraining the ego — because you can lose a lot. You spar with your team mates each week and sometimes you win, sometimes you lose. And you get better, and so do they, so you still lose. Or if you do well then you seek out better opponents so you can increase your chance of losing again.

But losing isn’t fun. And unlike other sports or competitions you cant reassure your ego and say ‘but I am better at X other thing’. Losing in a fight has a primal feeling to it, like you are objectively crushed. And to get better you have to spar a lot and hence lose a lot. And I cant explain it better than with this clip (hint: I am the one getting hit)

Ground & Pound

Developing new tech means that you have to be prepared to lose a lot, as well. I would say that 50% of my ideas and decisions are totally wrong. And that is me being complimentary to myself! I have made bad staff hires, bad design choices, bad uses of time and resources, executed bad marketing, and kind of excelled at a lot of other failure. But what matters is that I put an end to the bad decisions and ideas before they are too costly and retain the good ones. Darwinian evolution for ideas. Or to use the Startup vernacular: fail fast and pivot.

Admitting failure doesn’t feel good, but since I have a lot of weekly experience defeating my ego I am hopeful that I can lose less in the long run and not get stuck with a series of prideful errors.

And there is only one thing you can do when you lose: pick your self up and keep going.

Behind the scenes.. the lead up to the launch of the world’s first Law Firm Without Lawyers Was beset with problems to execute

Mostly, it is a grind

To prepare for a fight there is usually a 8–12 week ‘fight camp’ where you push yourself to a new level of fitness, hone your game plan and fix weaknesses in your skill set. MMA fights can be won and lost on cardio fitness. Unfortunately fitness is necessary but not sufficient. So you must have the fitness to go the full distance (3 x 3 min rounds for an amateur like me), but then once you have that fitness then you can compete using the striking, wrestling and grappling skills that you have.

A typical martial arts training schedule is 2–3 times a week. This is fun and is why I have trained for 25 years. During fight camp I trained morning and night 6 days a week. At first it was fun to get in all the extra training. But after a while it is tiring. But you have to do it, because on every early morning or late night when you want to rest, you can be sure that your opponent it out working hard. So training becomes a grind. And you just have to continue with that grind, because otherwise you will lose.

Here is a clip from sparring part the way through my fight camp. I had done a number of rounds of sparring, and was exhausted. But then I had to pick myself up and keep going.

Getting up exhausted to get hit again is not fun at all

Running a tech company seems like fun, you are creating something new, changing the world for the better, and it is so cool that everyone seems to want to call themselves an ‘entrepreneur’. But the old adage 1% inspiration and 99% perspiration holds true. Aside from the initial idea and creative burst, most of the time you have to grind through work doing mundane things to make it all happen. You have to build, and test, and refine marketing campaigns, and answer customer queries, and fix bugs, and deal with staff issues, and pay bills, and do your taxes and accounting.

Not only do you have all of the mundane grind of a regular business, you also have the problems from doing something that is untested and it goes without saying you will make a great deal of mistakes, meaning you then have to undo them and redo things over again. and probably again!

Unforeseen issues will always crop up, regulatory problems, customers or service providers (like banks) not fully understanding what you do, or just maybe your initial concept or idea just doesn’t work. While there isn’t a 8–12 week clock, there are definitely other people racing with you to do what you are doing and so you have to execute your Startup as quickly as possible before you get beaten in market share, or because your money or resources run out (including family willingness for you being absent or losing money compared to a ‘real job’). And so when you get beaten down (which will happen) all you can do is pick yourself up, and keep going.

South Australian Australian Young Lawyer of the Year. A few minutes before being awarded Young Lawyer of the Year I was given some tragic personal news. Behind the smile I was still in shock.

Teamwork makes the dream work

For my fight I had a striking coach, a wrestling coach, a stand-up grappling coach, a ground grappling coach, a cardio coach, a nutritionist, and a MMA coach who put everything together. I had a team of training partners who I would do striking, wrestling, ground and MMA drills and sparring with and of course I had a very supportive girlfriend who didn’t want to see her partner’s face beaten in!

Although it may look like MMA is a solo sport, there is a team and support network that is essential for getting the fighter there.

Celebrating With Coaches

Think it is a cliché to thank your coach, team and family? There is a reason why everyone does, and that is because they are indebted to them.

Similarly, whilst we make celebrities of successful founders of tech companies, running a company is not the act of a single brilliant individual. There are a huge amount of necessary skills that I don’t have and need others to do, not to mention a mountain of personal deficiencies and inadequacies that I need others to counterbalance. You also need a support network of family and friends who will accommodate your work and also make sacrifices, holidays, weekends, family events and more as they get dragged along on the rollercoaster of Startup life.

Adrian & Sarah Post Fight. I am very lucky to have someone as supportive as my fiancé Sarah.

Adrian Cartland

Adrian Cartland, the 2017 Young Lawyer of the Year, has worked as a tax lawyer in top tier law firms as well as boutique tax practices. He is now the Principal of Cartland Law, a boutique tax and commercial law firm. Adrian is also the Creator of Ailira, the Artificially Intelligent Legal Information Research Assistant, which automates legal research and information. Ailira has enabled non-professionals to pass University Tax Law exams and is currently used by hundreds of Australian tax lawyers and accountants for tax research and to unlock internal intellectual property. Ailira can also provide tailored legal information to consumers, initially in the areas of Domestic Violence (for which Cartland Law has already delivered a SA Government funded prototype), Business Structuring, and Wills and Estates. Ailira has powered the world’s first Law Firm Without Lawyers. Adrian is known for his innovative advice and ideas and also for his entertaining and insightful professional speeches.

The Winning Team



Adrian Cartland

Creator of Ailira, the Artificial Intelligence that automates legal information and research, and Principal of Cartland Law. www.Ailira.com www.CartlandLaw.com