The Lawntrepreneurs: Saahil Dama

In this edition of The Lawntrepreneurs, we interview a former Trilegal lawyer who went on to get selected by Entrepreneur First as a founder-in-residence.
Saahil Dama
Saahil Dama

The Lawntrepreneurs is a series where we chronicle the journeys of lawyers who have left the profession to start their own business ventures.

A 2017 graduate from National Law University, Jodhpur, Saahil Dama set foot on his journey as a lawyer with Trilegal, where he worked for 2 years before deciding to venture into legal tech entrepreneurship.

After a brief stint as a lawyer, Dama began his professional journey as an entrepreneur as co-founder of WorldWise, a profitable legal edu-tech company. Through WorldWise, he sought to democratize access to knowledge by bringing on board senior lawyers to teach courses launched by the company.

He later went on to secure a seat as one of the founders-in-residence at Entrepreneur First (EF), and was one among the 6 teams at EF to have secured funding from investors for his current start-up.

In this interview, he discusses his decision to switch careers, the journey that led him to EF, and more.

What was the turning point in your life that led you to venture into entrepreneurship?

It was a combination of different events which translated into becoming an entrepreneur. I think of the quote that Steve Jobs gave in his commencement speech at Stanford University - "The dots only makes sense when you join them when looking at them backwards."

The dots that really stand out from my journey was - while engaging in transactions work at Trilegal, the most interesting part was interacting with founders. I saw people not much older than me running these companies, overseeing 50-500 employees. Whenever I interacted with these people, I was just inspired by their ability to create something. I wanted to be on the other side of reviewing documents and actually start something of my own - to create an organization which has a legacy, and I really enjoyed that sense of ownership.

I enjoy being responsible for a lot of different things and not just responsible for one piece of the puzzle. It wasn't until recently that I could join all the dots and figure out this is where life will take me.

How difficult was it to quit a cushy Tier-1 law firm job at Trilegal?

Saahil Dama
Saahil Dama

It wasn't very difficult, because when working at a Tier-1 firm, they pay you handsomely. This allowed me to stay calculated and create a cushion, so I could have a runway of 2-3 years where I could afford to do whatever I wanted to within the realm of reasonableness. The decision was also made easy by the influences I was consuming - so I was reading and listening to a lot of Naval Ravikant's works and he talks a lot about taking calculated risks and pivoting away from doing a stable job to building something of your own. Jeff Bezos has this idea called the 'regret-minimization framework', which says that you should take decisions today which you won't regret when you're 80 years old.

All of these influences played a part, which allowed me to convince myself that this is something I wanted to do. That's where the journey really starts - you need to convince yourself before you convince anyone else. I then had to convince my family, which was the most difficult part.

What were the learnings from the company you first started that helped you set up World Wise?

The first company I started was Leagle Technologies, which was essentially a marketplace that connected lawyers with clients. The problem I identified while working at Trilegal was that it's great for big clients to hire fancy law firms, but there are a lot of smaller companies which struggle to find the right lawyer for their needs. As an insider, I wanted to change that, so I set out to create a marketplace which would allow clients to connect with lawyers for their needs.

As a solo-founder I was learning everything on the go, but six months in, I realized it wasn't scaling as quickly as I wanted it to, and that's when I decided to move on to WorldWise. The biggest learning was that I wanted someone to do it with me...The second learning was to push hard to reach where I saw other successful entrepreneurs reach...Given that I had carved a period of two years to establish myself as an entrepreneur, I decided to persist with another idea instead of going back to a conventional job. This is a thought I had before taking the plunge.

Tell us about your time at WorldWise.

Saahil Dama and his team at WorldWise with Senior lawyer Gopal Sankaranarayanan
Saahil Dama and his team at WorldWise with Senior lawyer Gopal Sankaranarayanan

With WorldWise, it was a whirlwind of a ride. I had a great co-founder and friend working with me...Given that we were building something together, we had a lot of enthusiasm which sustained us for a long time. At WorldWise, we were creating really high quality courses with the best lawyers in the country, which looked like documentaries. The idea was to democratize access to knowledge, and not just to study constitutional law from professors at law school, but also study it from a senior advocate who has argued the Puttaswamy case, or study arbitration from a Partner at Shardul Amarchand Mangaldas who is also on the board of the Singapore International Arbitration Centre (SIAC).

After about fifteen months of running profitably, we came to a realization that the legal education market was not actually very big. We were considering the option to move beyond legal education and create similar courses for other fields...that's when we realized that we didn't have the expertise to create courses with doyens in other fields. We also pitched to investors at that point in time, and they expressed the same concerns. By then my ambition had become bigger.... and I wanted to created a larger venture-scale business. So my co-founder Sanjay and I discussed and decided it was best we went our separate ways... Coincidently, at that point, we approached UpGrad who eventually acquired all of the courses and the intellectual property.

What did it take to get selected to EF among over 4,000 applicants?

This was my 4th attempt at EF...By this time, I had made something out of WorldWise, so I could actually say I am a profitable entrepreneur. Before that, I was only an aspiring entrepreneur. The application was very exhaustive, but by then, I was already comfortable with all the questions. Two rounds of interviews followed, after which I was selected.

Can you elaborate more about EF and what your stint as a founder-in-residence was like?

EF is a global talent incubator. They have operations in London, Berlin, Paris, Toronto, Singapore and Bangalore... they are not investing in companies, but in people as entrepreneurs. They gauge whether you as an individual are capable of starting a ground-breaking company or not - so you don't need to have an idea or a co-founder. You only need to convince them that you have it in you to start a large successful venture.

Once EF makes its selection, the program goes on for six months, where the first three months called the "form" are targeted to finding a co-founder among the 40 selected entrepreneurs during which process EF mentors you. During this period, EF also pays you a very healthy stipend because they want to de-risk the exploration that individuals have taken up. At the end of these three months, if they like your team and the progress you've shown, they invest a small amount of pre-seed funding into your company and they help you incorporate the company... set up more calls with investors, etc. So my co-founder Avi and I were able to raise funding from EF, with which we have been building a product in the legal tech space since January this year.

What are you working on currently?

I knew I wanted to build something in the legal tech space, because EF strongly emphasizes on finding your edge. Given that I had a legal background, and having had experience as a lawyer, I identified that one of the problems that law firms face is the time consuming and inefficient process of drafting and reviewing contracts...We are building AI to streamline this process, where the AI acts as an intelligent assistant while reviewing or drafting a contract...Having worked as a lawyer I understand a lawyer's work...We are trying to create a tool that is so accurate that every lawyer would want it when reviewing or drafting a the level that it becomes a must-have product, as against a nice-to-have product.

What advice would you have for young lawyers or law students looking to step into entrepreneurship

Firstly, it is important to cap your downside...I didn't see entrepreneurship as a plunge, I knew what my exit plan was. I knew I had the financial runway for two years and my boss at Trilegal was kind enough to leave the option of returning to the firm if things didn't work out...Whenever you're doing anything unconventional, it's very tempting to go all out, maybe it works for some people, but for me, knowing that there was a safety net made the experience lot less scary...else it might have gotten frustrating on the bad days that are inevitable.

Secondly, training as a lawyer teaches you skills crucial to entrepreneurship like sales and marketing, building relationships, pitching to investors, etc...When preparing a pitch deck or writing an email to an investor, they really don't care whether the comma is in the right place or not...they care about what is happening under the hood of the start up. So I had to re-train myself. As a founder, you have to work a lot faster and don't have time to nit-pick on the smaller aspects. Being open to re-training is therefore important.

The third piece of advice is that, knowing why you want to do this is critical. It is not a good idea if you are doing it for external reasons like peer pressure, or wanting to impress someone...the motivation at its core has to be true. The motivation for me was that I enjoyed building stuff, taking ownership, being the topmost person in the hierarchy as opposed to being the junior-most person. This kept me going even when things weren't working out...I like the freedom this gives me, to brainstorm and modify the product, sales strategy, etc...For those who want to make the switch, getting the motivation component right is absolutely critical.

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