“You never know when and where you can be “bitten by the entrepreneurship bug.”   

Something similar happened with our guest Shashank Bijapur. A graduate of Harvard Law School, he was working with a New York-based top-tier law firm; when he came across the news of Elon Musk launching Self-driving cars. He realized his manual work on Legal contracts was easily replaceable by AI automation soon.

This led him to start SpotDraft, an end-to-end contract automation platform for companies of all sizes. In this episode, Shashank talks about his initial hiring struggles, getting new clients, some of his mistakes as an entrepreneur, the future plans for SpotDraft, and much more.  

Notes – 

01:19 – Starting SpotDraft and meeting his wife for the 1st time

04:51 – First few years of struggle

07:28 – Timeline of Shashank & SpotDraft’s Journey

10:34 – Switch of TG: From Enterprise to Startups

12:58 – Early customers: Unacademy & Chargebee amongst others

14:36 – Hiring A+ talent: Referrals from existing employees

17:01 – Mistakes in 0 to 1 Journey

22:18 – Competitive edge over large competitors

25:23 – “Let’s get SpotDrafted.”

Read the transcript here

Shashank 00:05

This actually happened at an investor meeting where we did not understand what growth was. The idea of growth was we had one client two months ago, we have three times now for us, we were happy in that. And then somebody used the word PMF. And I didn’t go to business school, so I don’t understand the three-letter acronym. So I went and googled and looked it up. And I’m like, Okay, we need product-market fit. And one of the key elements of product-market fit is, you’re able to replicate the use case and the outcome of the software, for example, in our case, repeatedly for a given problem statement within a given market, none of that existed for us, then.

We did not have a repeatable sales process, we did not have a repeatable product that was there. It was almost like a custom built software that we had to build for each new client. And we could have become a great family business, but this wasn’t going to be a rocket ship that we were really looking to build. That’s when we realized that hey, there is this entire mid-market segment where I keep saying this if you want to go buy a car, the two showrooms you don’t land up at are Ashok Leyland and Bajaj.

Siddhartha 01:28

Dear listeners, this is your host Siddhartha Ahluwalia, founder of 100x Entrepreneur podcast. Before we begin, I would like to thank our sponsors Prime Venture Partners. Prime is the first institutional investor in the category-creating tech startups like Mygate, Neo, Dozee, PlanetSpark. Prime is now investing out of his fourth Fund, which is more than 100 million dollars. And today we have with us Shripati Acharya Managing Partner, Prime VC. Shripati, when entrepreneurs are looking for money in the company, how do they evaluate the quality of their money? 

Shripati 02:06 

While money itself is a commodity, the people behind it are not. Your investor is also your board member for the life of the company. So, the key thing to figure out as a founder is, do you see your investor as a strategic partner with whom you can have critical conversations, founder issues, hiring and firing decisions, acquisitions, partnerships, the exit of the company, and everything else. And the way to figure that out, is to not only have meaningful conversations with the partner, but also deep reference checks with the portfolio CEOs of that investor.

Siddhartha 02:46

Today, I have a founder who I’m very close to as a friend. And he has built a journey, which I haven’t seen any other. He returned from the US. Had a fledgling career in the US, returned to India, lock, stock and barrel with his wife, and now has built a global product, of which 50% of the users are in the US. So welcome, Shashank Bijapur, founder of SpotDraft, on the 100X Entrepreneur podcast. I am grateful to have invested in your journey of SpotDraft. Shashank, welcome to the show.

Shashank 03:25

Thank you, Siddhartha. And thank you for that introduction. And it’s really our pleasure to find a mentor, an investor, and a friend in you. We’re all big fans of 100X Entrepreneur, we follow the podcast. My pleasure to be here today and share my thoughts on what we’re building here at SpotDraft.

Siddhartha 03:49

Shashank I’m very excited to share with listeners your journey. So tell me your journey before starting SpotDraft. And also I want to know how you met your wife.

Shashank 04:02

Yeah, so the journey was, I started out as a lawyer, so I would like to call myself a recovering lawyer right now. I studied in India, worked for a couple of years in India then did my masters at Harvard Law and went on to work with this firm called White & Case in New York, which is a Wall Street Law Firm. And it was this day, which was just before New Year. My office was in Times Square. And everybody was outside but I was sitting and doing some due diligence work. And I read this new story about this guy called Elon Musk who’s building a car that would drive themselves and then it hit me. Cars are driving themselves and I’m still here copying pasting words in a contract and there’s something that needs to change. So, I went around looking for whatever specific software and automation tools were built for lawyers and there were none. 

And that and I had an entrepreneurial bent of mind, I’ve always wanted to be an entrepreneur. I think that was the time in 2015- 16, when India’s startup growth journey had started. All of us were sitting in the US looking at India and going like, we need to be part of that growth journey. And that drove us to come back.

And how I met my wife is the same place where I met my co-founder at a Diwali party. So I was at the Diwali party where there were just designers and I met my first co-founder, Madhav, and now we have one more co-founder, Rohit. So Madhav and I met at that Diwali party, and where I met my wife, so a lot of startups started at that Diwali party.

Siddhartha 05:52

Wow. That’s a very interesting journey. Were you married before you started SpotDraft? 

Shashank 06:01

No, I wasn’t. I was working on the idea of SpotDraft, and I got married. And three months after marriage, I said, Hey, I’m going to no longer pursue what I’m doing and do this thing called startup and build something in legal tech. So I knew the legal part of it. I didn’t understand the “technology” part of it, Madhav and I got together, Rohit joined in on the product side. And we started building SpotDraft, which was slightly different when we started, though.

Siddhartha 06:32

And were your in-laws, and your wife got a shock that we married a stable guy, a lawyer, and now he’s going crazy on building a dream of his own.

Shashank 06:46

Thankfully, I’ve been lucky in that way where everybody around me has been supportive. and I’ve never had a question being asked, What are you doing? Or is this even relevant? My in-laws, my parents, my family, have been very supportive of what I do. If you ask me as a founder, a lot of what goes into building a startup is borrowed time from your family that you’re taking away from them to do what you want to pursue as your entrepreneurial journey. And having that support was very important. And I think I found it in that.

Siddhartha 07:26

Tell us the first few years of struggle of building the product, finding the right market, finding the first few investors, what went into it?

Shashank 07:36

Yeah, so I think what we started doing was, we started speaking to a bunch of our customers who we thought were our customers. And at that point, we thought every founder was a customer. For those of you who don’t know what SpotDraft does, we are an end-to-end contract automation platform. So, think of us like the Salesforce for contracts, contracts get created, managed, analyzed, and collaborated upon using SpotDraft, so you can close deals faster. Now, we thought that the founders had this problem. So we started speaking to founders, and then we realized that, no, it’s probably the lawyers who have the greater problem around contracts. And the mistake that we made at that point is, we ended up asking what do you want as a product? And the answer was, I want a machine to come and read my contract and tell me the good, bad and ugly, which essentially replaced me with a machine.

That sounded exciting as an idea. AI, NLP was still in its infancy compared to today. It’s grown manifold from where it was. We said, Hey, this is a very challenging problem, there seems to be a big enough market, everybody seems to be taking a lot of time to review contracts. Let’s build this out. We built a very successful pilot on it, where you would put an NDA and it would tell you whether this NDA is compliant with your internal standards or not. Where we struggled, there was a scale from going from one client to the other, we realized that that knowledge and that training was not easily transferable. There was a dearth of training data, if the document is called in non-disclosure agreement, companies are not going to disclose it for our training purposes as a data set. 

So those were the challenges that we saw. And we realized, how do we build this entire analysis piece in a way where the user doesn’t even know they’re training the system, but we are getting the learnings out of it. And that’s how SpotDraft, for the first year and a half was a slightly different version to what it is today. We are about four years old now. So it was in the early days of the pandemic that the 2.0 of SpotDraft was really born.

Siddhartha 10:00

Can you describe the timelines? Exactly If you remember what month year you returned to India, when did you launch the first product? And what took it from there to the first few customers?

Shashank 10:13

So late 2015, early 2016 was when I returned to India. So, I have had zero interaction with startups, founders, technology, I was a lawyer doing m&a for my living. So, I wanted to experience what a startup life looks like, what does it mean, other than listening to podcasts and reading news articles, so I ended up working with my cousin who runs a very successful FinTech company called Rupee power. It’s a b2b software provider for banks. I worked there for a year just to understand, hey, what is product, what is technology, who does what? And 2017 April was when I started working on SpotDraft, in the form and manner it is. 2018 was when we raised our seed round, and which was, again, we were grateful to have some amazing early investors, including in that round Hunch, 500 startups and Singapore Angel Network. And then the next round was 2019, which is a pre-seed round, where zero to one capital, which is Sailesh Tulsian, and a fund that is anchored by Binny invested in us, that was surely the tipping point of us being this very enterprise-focused business that was going from deal to deal. These were large deals, but they would take months to close and months to implement, to get something that was agile, immediate, and sort of implementable in a few days, not a few months or years.

And then zero to one has been, and you may know we are closing a pretty large round as our Series A right now. And we’ve grown almost in the context of this podcast 100x, from where we were, a few years ago to today. 

Siddhartha 12:25

And can you describe the current round? How did it happen? 

Shashank 12:30

We’ve been lucky to have you onboard as well. And you’ve made some phenomenal connections for us even before the round closes. So it’s really to ease our growth and what we are doing next.

Siddhartha 12:44

And by December 2022, where do you think SpotDraft will be?

Shashank 12:52

Yeah, we are on target to hit $5 million in ARR. I think that is almost a 50x or 500x  journey from where we were two years ago to where we are right now.

Siddhartha 13:08

And as a founder, you were earlier building for enterprise? When did you start to realize that enterprise is not your ideal customer profile? And when did you fish from enterprises to mature startups as your TG?

Shashank 13:26

So this actually happened at an investor meeting where we did not understand what growth was. The idea of growth was that we had one client two months ago, we have three clients now and we were happy in that. And then somebody used the word PMF. And I didn’t go to business school. So I don’t understand the three letter acronym. So I went and googled and looked it up. And I’m like, Okay, you need product market fit. And one of the key elements of product market fit is you’re able to replicate the use case and the outcome of the software. For example, in our case, repeatedly for a given problem statement within a given market. None of that existed for us, then.

We did not have a repeatable sales process, we did not have a repeatable product that was there, it was almost like a custom built software that we had to build for each new client. And we could have become a great family business, but this wasn’t going to be a rocket ship that we were really looking to build. That’s when we realized that hey, there is this entire mid market segment where, I keep saying this, if you want to go buy a car, the two showrooms you don’t land up at are Ashok Leyland and Bajaj. That was what was available for the mid market segment in terms of contract management. And we started building SpotDraft for the mid-market right after that and we started seeing some extremely phenomenal growth after. 

But one thing I’ve realized out of this is, I don’t think any startup today can start an enterprise first business and really find product-market fit in the first year or two years. That journey is very hard. It is not scalable and repeatable. And the idea of your product is very different from the idea or the requirement of a product that the company is that the enterprises want to have, they always want 20% of your product and 80% of their ideas stack on top of it. And that means you’re building everything all over again, which are perhaps not reusable pieces for clients over and over again. And that’s just a very difficult journey to do. And if you look at the SaaS playbook that we see these days, you always start mid-market now and then much more enterprise as you grow.

Siddhartha 15:54

And who would be your first 10 right set of customers, if you can recall?

Shashank 16:01

Yeah, So the first, we had these enterprise customers who were there, but some of our first customers were Indian unicorns, who started using us. So, we had Whatfix, Chargebee, Unacademy, cred, PhonePe all of them. And some of them really took a bet on the fact that, hey, these guys will figure out the product. But we have a problem and they understand the problem. Nobody was speaking to us about the problem that the legal teams had till now.

And right after that, it has pretty much been, we’ve gotten almost a large chunk of the Indian unicorn market. We’ve got a bunch of customers outside of India now 50% of our revenue is coming from non-Indian customers.

Siddhartha 16:54

And today, if you can share a ballpark number of the customers, which SpotDraft has.

Shashank 17:01

 We are right now at about close to 100 customers of which 50% are in India and 50% are outside of India.

Siddhartha 17:12

A real quality, which I admire in you as an entrepreneur is being able to attract the A-plus talent, that really goes out of the way. Even early on, how did you build that, was it natural for you? Or is this something you learned over a period of time?

Shashank 17:30

It’s definitely not natural. And I feel there is some amount of luck. The luck came from the professional networks that each of the founders came from. For example, Madhav and Rohit come from Carnegie Mellon. A lot of our early employees came from Carnegie Mellon from that circle. And what we tried to build is an incredible culture and a set of people who are really passionate about what we were doing at SpotDraft, they became our most vocal supporters. So they would go and find the talent that was there, the people that they had worked with, that they loved working with, and they would refer and come in. So a bunch of our current set of employees is all referrals from existing employees. And that’s how we’ve grown. We struggled a lot Siddhartha in the early days, when we would not find the talent, it was very difficult for us to explain what we were doing and why that was relevant. But now that the mission and purpose is a lot clearer, and people are enjoying the growth that we are seeing, we are also able to attract some really good folks on board.

Siddhartha 18:45

And you have recently become a Dad. Congratulations on that. How do you balance your work life and the growth pangs of a very fast growing startup?

Shashank 18:58

Yeah, that’s a good one. I have tried to figure out what startups take importance on which part of the day. We figured out a model where during the early mornings and evenings is my baby duty and most of the day is where I focus on the other baby SpotDraft. It is a different journey. It’s an amazing experience. And I’m really enjoying being a father right now.

Siddhartha 19:31

And if you can recall, there are like 1000s of founders listening to this podcast, the zero to one journey, what are the mistakes that you made? And in hindsight, which you wouldn’t have made today?

Shashank 19:44

This is very important. I think the few mistakes were we did not focus on ACTIVE SELLING and distribution earlier. We focused way too much on listening to the customer and building for the customer, and not building for the problem that the customer had. So people wanted a button to be posted somewhere, they wanted a certain way in which the page looked, we would just go and make the change. We never questioned the customer as to why do you need this, that has started, I felt like we spent about almost close to a year in that space where we were just going and speaking to customers building for them, and not being able to reuse anything, and not having a set of team members who are delivering the value of the product to others externally.

So, if I had to go back and change something in time, I would build the sales and marketing functions way earlier in the life cycle, and focus more on compounding and delivering that value that software has, that we are building and showing that to the end customer rather than going to the customer and speaking a lot more product and trying to build for them.

Siddhartha 21:07

So there is a very important nugget of wisdom here in what you said. So you mentioned that you listen to the customer and build for that. Whereas there’s a very different problem, which as a founder, you have to identify which may not be there in what the customer is saying.

Shashank 21:27

Well, you’re right. I’ll tell you what that means. If you go and ask, What do you want, and you’re looking to buy a car, they’ll probably end up describing a car that is completely fully self-driven, goes 0 to 100 in 3 seconds, none of which are really useful. Those aren’t the problems that the customer really cares about. They want safety, they want affordability, they want spaciousness, and none of them really come out as features. So if somebody before Uber, if somebody had to describe the problem that they had, and the solution that they wanted, they probably would not describe Uber in the form and manner it is right now, and the solution. They would describe what in their limited understanding, they think could be a great solution. Doing that, replicating that without really thinking through what is the outcome that is needed, and engineering it that way, was a mistake that we made. Listen to the customer for the problems they have, and build for the solutions yourself, not the solution that is asked by them, but meet the outcome that they desire. That is what this is about.

Siddhartha 22:44

And how do you differentiate between the outcome you think the customer wants and the features that the customer wants? They’re two very different things.

Shashank 22:58

So this took us a long time to understand, were they asking for a feature? Or were they trying to ask for an outcome? One thing that helped was we have a lot of lawyers that work at SpotDraft, who are legal engineers who do a lot of other functions, but come from a legal background. So we were able to translate a lot of what they wanted as what they thought as problems into desirable outcomes.

It did take some time, because it doesn’t come naturally to me as a founder on what the outcome is, but I could where this sort of legal and pseudo product had to understand what that outcome was. What we realize today is people don’t want a system that can read your contract and tell you what is good, bad and ugly. What they really wanted was a faster turnaround time on their contracts. That was the outcome that they desired. What they described as going into my contracts and telling me the good, bad and ugly, was their version of the car that they wanted, not really the outcome that was there. So we started building for this. A bunch of automation tools around contracts that could answer a few questions, your contract is ready in less than 30 seconds. That will take a couple of days before SpotDraft. 

So one of our customers was telling us that the journey of before and after SpotDraft is pretty much like the journey before and after Uber where you would stand on the road, wave your hand and say your auto, and now you’re just looking on your phone and booking a cab at your convenience and requirement that is the sea of change that they see.

Siddhartha 24:46

And when customers compare you and the biggies, let’s say ironclad icertis what helps you win that battle.

Shashank 24:58

I think the biggest one is the fact that we are end to end in our form and manner that we are, they want one integrated system that does everything around contracts. And that does it beautifully. The second is very simple to use and very beautiful to look at. It is something that a lot of lawyers struggle with having clunky age-old software. The third is we’re very malleable as a product. Given our experience in enterprise and our learnings there, we realized that if we build the base as malleable as possible, where you could put any contractual use case, any contract related use case on SpotDraft and make it work, that really helps. So there isn’t an edge case that cannot be solved using the SpotDraft system. As far as creating a contract negotiating them collaborating on them is concerned. 

That is a differentiator and last is, I think we give a lot of love to our customers and really focus on them with what we do. We went and read all the one-star reviews everywhere for our competitors and said, Let’s build these pieces out first and focus on these pieces and make them as our differentiators, which has worked well. In fact, Inc42 now rated us as amongst the best contract management software’s to use when we were in 2021. And we were amongst the fastest growers there.

Siddhartha 26:27

And if you have to think about your journey from 100 customers right now to 1000 customers, what are the things that you would like to keep the same in SpotDraft as a team, as culture, or as a process? And what are the things that you would think would change or need to change?

Shashank 26:43

Yeah, I think what we want to keep as is the customer centricity in terms of delivering outcomes, and doing that, right, that’s one process. And second is having a human-led onboarding and initiation experience, which people like, rather than having to come in and just click a few buttons and get onboarded. I think that the human touch works a lot. Our inspiration was the superhuman onboarding that happened for us, I don’t think without that onboarding experience, I would have been able to use superhuman. But that really made a change, and we are going to keep it the same. What we want to change is to make a lot of product lead growth initiatives, get plugged into the platform. Right now, a lot of that is human-driven, it is a push, we can make it a pool with some smarter design smarter, segmenting, and letting people grow into a larger customer without a human being involved. 

Siddhartha 27:50

Shashank, what’s your biggest vision for SpotDraft and for yourself?

Shashank 27:58

I think the vision of SpotDraft is to turn from a noun to a verb. Somebody should say what happened to the contract? Let’s just SpotDraft it. That is where we want to be, we want to be the number one contract automation platform in the world. And there is no reason we won’t be able to do that. We have a solid product, we are growing at the pace that we would have liked to grow. We have found the right product-market fit. I think now is the time where we want to put fuel into the fire and expand our outreach and sort of multiply the efforts that we are doing and grow. A lot of the critical learnings that we wanted have come in for this expansion. If you asked me the same question a year ago, I probably would not have been able to answer but in the next three years we will be a $100 million ARR company that is extremely doable. We have a plan for it. We are executing on that plan, we will get there.

Siddhartha 29:09

And if I asked you how Shashank changed as a person pre SpotDraft and today.

Shashank 29:16

I think I have a lot more patience and resilience for failure than I had before. As a founder, I have heard more no, either in sales or in fundraising or in recruitment than ever before. Had that happened to me earlier in my life, I would have felt really dejected. This has made me way stronger, way more resilient. That’s one. Second is, there was a time when I thought being a founder was for the money and the fame that is there. I think that mindset has completely gone away.

I love being the founder for the value that I’m able to show to our customers, as SpotDraft and some whatever change that we are able to enable for the people who work with us. And to see them grow. I think that joy is the most amazing thing. So, it’s gone away from being a business to being a real passion of wanting to solve a problem that customers really care about.

Siddhartha 30:37

And I see a lot of books behind you. So do you get the time to read them? 

Shashank 30:46

Yes, I am a voracious reader. I’m reading Good to Great right now. It’s a great book, if you guys haven’t read it, it’s written by Jim Collins. I read almost every day. These days it’s more of ebook reading rather than paperback reading. But whenever I’m on a flight, or in bed, it’s usually a book in my hand reading.

Siddhartha 31:14

And what are your systems for your own learning? You mentioned daily reading, is there a system that you have to read half an hour of a certain number of pages? And what are the other things that you do to grow yourself as a founder?

Shashank 31:26

Yeah, I think one thing that I do is, I read a lot. There is no specific time or a specific number of pages I read, as long as I like it. The other thing I do is, I run here and there and try to keep myself fit. Physically, I meditate a fair amount in the morning, usually about 30 to 40 minutes before I start working.

The other things I do is read news, and what is happening in the competition around us with fundraising, where’s the market going, just getting a slightly more macro viewpoint around the world because as founders, you tend to be so ingrained into your own problems at the company and your own growth objectives in the company that you forget how the world is thinking and where that is going. I spend a lot of time doing that. Then I also try to do activities that have nothing to do with work, which is that I love cooking. I used to track a lot but now I stopped that but I love cooking and I continue to do that like a stress buster.

Siddhartha 32:44

Thank you so much, Shashank. It’s been wonderful to step in your shoes, learn from you and experience your life in this conversation.

Shashank 32:53

Thank you Siddhartha, it is absolutely my pleasure to have the opportunity to be able to speak with you and share some of our thoughts. It’s been incredible and I’m looking forward to our journey going ahead.

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