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Jay Mandal

Jay Mandal is an entrepreneur, executive, and lawyer. Currently, he is the vice president of corporate development and strategy...

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Monica Bay

Monica Bay is a Fellow at CodeX: The Stanford Center for Legal Informatics. She also writes for Thomson Reuters, ALM (Legaltech News),...

Episode Notes

Jay Mandal saw a problem with access to legal information so he sat in a Starbucks for hours until he figured it out. This was how his startup was born. He now helps law firms solve their own problems (minus spending hours in Starbucks). In this episode of Law Technology Now, host Monica Bay talks to Jay Mandal about his own startup experience and how his startup bootcamp for lawyers helps students learn cross-disciplinary skills that can make their legal businesses thrive.

Jay Mandal is an entrepreneur, executive, and lawyer. He was co-founder and CEO of LawPivot, an online legal Q&A solution, which the team sold to Rocket Lawyer.


Law Technology Now

Startup Bootcamp for Lawyers


Intro: You are listening to the Legal Talk Network.


Bob Ambrogi: Hello. I am Bob Ambrogi.

Monica Bay: And I am Monica Bay.

Bob Ambrogi: We have been writing about law and technology for more than 30 years.

Monica Bay: That’s right. During that time we have witnessed many changes and innovations.

Bob Ambrogi: Technology is improving the practice of law, helping lawyers deliver their services faster and cheaper.

Monica Bay: Which benefits not only lawyers and their clients, but everyone.

Bob Ambrogi: And moves us closer to the goal of access to justice for all.

Monica Bay: Tune in every month as we explore the new legal technology and the people behind the tech.

Bob Ambrogi: Here on Law Technology Now.


Monica Bay: Hi. I am Monica Bay and welcome to Law Technology Now. I am delighted to have Jay Mandal as my guest today. We have known each other for quite a long time. He has had a fantastic and very, very interesting career.

So Jay, I am going to start you off please by telling us a little bit about what you were doing when we first met and it was at Rocket Lawyer.

Jay Mandal: Right. So at Rocket Lawyer I was in charge of the Legal Advice Business, all the products to connect individuals and consumers to lawyers, and my CEO Charley Moore gave me about two or three days notice that they needed someone to be in Los Angeles to speak at a Legal Tech Panel, and I immediately got connected to Monica.

Monica Bay: I remember it. It was one of these last of the minute things and I was literally sitting in the hotel and going, oh my god, I really, really, really need a person and it was — we decided to do a whole track, and my boss just basically said you do it. I was eating dinner when you called and said you could do it, and I was so happy. It was absolutely delightful. That was a good event.

Jay Mandal: It was fantastic. I think I flew out two or three days later to Los Angeles and met Monica for the first time and it was the beginning of a great friendship and great collaboration that ended in us both being at Stanford as CodeX Fellows.

So great, great start to a great relationship.

Monica Bay: So tell us a little bit about how you ended up with Rocket Lawyer buying your product and how you got into legal tech?

Jay Mandal: Absolutely. So my path to legal tech, like many people, was quite circuitous. I spent the first nine years after law school as a corporate M&A attorney at firms like Pillsbury, and my last legal gig was as the head mergers and acquisitions lawyer at Apple. And even at Apple as a so-called sophisticated attorney even I had difficulty finding the right attorney to meet my needs for my questions. And so after a few years at Apple I thought, hey, why don’t I jump out and try to solve this problem.

So I thought I could harness some of the ideas of legal technology or at the time I guess nascent legal technology and social media to figure out how to connect clients and lawyers instantaneously. And so that was the genesis of the idea we called LawPivot.

So I left my job, as did my co-founder Nitin Gupta, and we sat at Starbucks for three months thinking about an idea that would address this. And we came in with our aha moment at a table at Starbucks I remember even to this day, which was basically the idea of a confidential legal Q&A service that would allow small business and lawyers to ask questions on our platform and get up to three confidential answers within one business day.

So that was the idea. And we built that company over three-and-a-half years and were very lucky after being rejected by over 40 I think VCs, going up and down Sand Hill Road, to be funded by Google Ventures and Sequoia, and that’s where we then connected with the folks over at Rocket Lawyer.

So it was about two rounds of funding and we were pitching Rocket Lawyer for a partnership, and they said, hey, why don’t you join forces with us and that was the beginning of our relationship. And they eventually acquired us and said that we would be the ones that would build up their Legal Advice Business using our online legal Q&A product as the cornerstone and that was how we were acquired by Rocket Lawyer and the team over at — Charley Moore and his leadership team.


Monica Bay: It’s so funny because it just brings back so many memories, because I think that was for me the very peak of where we were really starting to see a change in how lawyers were dragging along for a long time, but it was one of the first times where we really started to see how law and startups could really kick in. And there’s so much resistance to it, particularly the baby boomers, it was so hard and very few people were in there.

And the exponential way that this all has worked is just so amazing, and I look now at what we are doing at Stanford and it just blows me away. It’s such a phenomenal change we are going through. I kind of wish that we all had two more lives, because it’s just going to be so interesting in the next 50 years, it’s absolutely amazing.

So what happened then, you got to the point where you got the deal done and so Jay, how was your transition when you left Rocket Lawyer?

Jay Mandal: Yes, that was tough because I was leaving my baby of this legal Q&A product at Rocket Lawyer and had spent a couple of years working with the team incorporating the product and had serviced over a 100,000 consumers and businesses using our product and other products. So I felt like my job was done there and it was time to move on.

And the overall mantra I have in my career is to try to find ways to use technology as a way to democratize access to services and that could be legal, where I started with, but it also could be marketing technology, it could be finance and accounting. So I decided to expand my wings and move on to the next challenge, which was Optimizely.

At Optimizely the idea there was — or the technology there was providing A/B testing to online legal technologies to be able to better optimize their sites.

Monica Bay: Excuse me Jay, what’s an A/B?

Jay Mandal: A/B testing is the idea of giving users on any website two different scenarios to go through in their user experience and the underlying technology tests whether scenario A or scenario B leads to greater conversion.

And so Optimizely had created a disruptive technology that allowed websites, from small websites all the way to websites like ESPN be able to present the so-called an A/B test scenarios to test user optimization through their site.

So back to your original question Monica, so I had a chance to be a product strategy and corporate development executive at Optimizely and then moved on to be a executive for product strategy over at SAP, which is my recent job or most recent job, in which I have the opportunity to lead the product strategy for our ERP business, which is essentially financial accounting platform for small and medium-sized businesses. And our current platform services about 60,000 companies worldwide that are using our service to help them build their business using our online and on-premises technology platform in accounting.

Monica Bay: Jay, we are going to take a quick break for our sponsors and then we are going to come back and talk about the Startup Bootcamp for Lawyers. We will be right back.


Christopher Anderson: I bet you didn’t think about running a business when you were in law school, but now that you have your own practice, you are constantly looking for tips on marketing, accounting, practice management, and so much more. I am Christopher Anderson and you can get expert business advice on my podcast, The Un-Billable Hour, found on  HYPERLINK “”, iTunes or wherever you listen to podcasts.


Monica Bay: So we are back. Thank you very much. And Jay, let’s talk a little bit about the incredible program we had at CodeX for the CodeX FutureLaw and then following after that you did an inaugural group for a Startup Bootcamp for Lawyers and I was so thrilled that you invited me to participate in it, and it was absolutely amazing.

Jay Mandal: Yeah. Thanks Monica and thanks for your involvement in the Startup Bootcamp for Lawyers. I have been actually speaking to Roland Vogl, the Executive Director at CodeX for many years, since my days at Rocket Lawyer about the idea of teaching law students cross-disciplinary skills to better prepare them to become 21st Century lawyers.


And what I mean by that is that lawyers nowadays are expected to provide business-oriented advice to their clients, there are disruptions in legal technology, there is automation in legal technology, and there’s this idea or expectation of instantaneous legal things that that clients now demand.

In order to do that, lawyers need to be trained differently. That actually percolated over a few years and then it resulted in this idea of the Startup Bootcamp for Lawyers. And so the essence of the Startup Bootcamp for Lawyers is this idea of providing lawyers the skills in product and design and pitching to learn how to be more entrepreneurial-minded as practitioners in law firms or as in-house counsel or startup founders.

And what we did essentially is we asked a group of 25 Stanford law students over the course of a few days to act as startup founders and take a business idea all the way to fruition to a VC pitch and pitch that to a group of three VCs at the end of our course and learn the skill sets and product design that would be necessary in order to do that.

And that was our attempt at giving them a taste of some cross-disciplinary skills that would help them better be prepared as lawyers coming out of law school.

Monica Bay: So tell us more about in terms of the logistics of it. How did you pull it? Where did we go? I think a lot of young lawyers are really starting to think about, can I do this sort of a thing, how do we incorporate tech? Can you walk us through the planning and how we physically did it and what was the biggest surprise for you on that?

Jay Mandal: Our whole agenda for this class at Stanford was to treat again lawyers, the law students like startup founders. So we created a whole lesson plan and hands-on training session of helping them think through what it takes to ideate a business idea, to take them through the process of designing a product, then developing that product, testing it with each other, learning how to create a pitch deck and presenting that idea and then how to go through the process of actually actively pushing it to VCs.

So giving them skill sets and product design that they never — in some cases, never had come across. That was the idea. And we gave them four areas, actually six areas, which they developed their businesses in, which were completely unrelated to law, areas like virtual and augmented reality, education, legal tech, health fitness and IoT to develop their business ideas.

So the thing that really surprised me through this process and that surprised my co-organizers Susan Salkind and also Jose Torres was that these lawyers were thirsty for this type of knowledge and took their assignments incredibly seriously, to the point where at the end of our class when they pitched it to our group of three VCs, our VCs even commented that, hey, it seems like you guys have been working on this idea for many months instead of just a class.

So I think that’s what surprised us is the passion and the true interest by the law students in pursuing this idea and taking some of the teachings to heart.

Monica Bay: And it was interesting too because you had told me that you did not expect the number of people who wanted to apply and it was limited for 25 and they had to be members of the law school at Stanford. How many people did you have to turn away?

Jay Mandal: Yeah, we were pleasantly surprised. We expected just maybe a dozen or so students would be interested in our class and when we sent out our registration invitation, we ended up getting 100 people who were interested. Of those 100, 50 of them were actually practicing lawyers, including folks like judges and senior attorneys, which was very surprising to us, because we specifically said this class is only for Stanford law students.

So we ended up choosing of those 50 law students, 25 law students to join our class and prepared our coursework accordingly for a slightly bigger class than we expected.


Monica Bay: One of the big surprises for me was the number of women who were there, we counted it and it was literally I think 50/50 with the guys and that was a huge surprise. Silicon Valley is notorious for having only 20% of women in tech shops and that’s not just legal, that’s broadly, but the legal community, particularly big law, is really struggling. There is still a 17% gap between men and women on their money. It’s 80% in big law.

It’s really been amazing and I was blown away, not only by that, but the diversity of the people that were there. It was just obvious that we had a really good mix. Did you make any particular attempt to attract those folks or was it just serendipity?

Jay Mandal: No, we actually — that’s a really good point, we were very pleasantly surprised by the diversity, but we made a concerted effort, Jose and myself, to make sure that we had strong representation of women and minorities, not only amongst the students, but also the mentors, the panelists, and the organizers of our event.

This is a personal belief of mine, but I think we should have as inclusive a tent as possible to make sure that the best talent rises. And so we made sure that we had five women panelists, mentors, organizers involved in our session.

We went out of our way to have a very diverse pool of VCs who were judges. To the point where I got on the phone and was actually calling one of the VCs I didn’t even know to make sure that we had good representation on our panel. So we were very happy with that.

Monica Bay: That’s something that I write about rather intensely now. We are both Stanford Fellows and I have just been very, very happy about the opportunity, because I do a lot of blogging for CodeX and it’s just so exciting to see this happening. Was there anything that disappointed you in the process or that you had to learn from that was maybe a surprise?

Jay Mandal: Yeah. So I think the thing that disappointed me was we did not expect so many students to be interested in this course and so had we known we would have made the course even longer and we would have figured out a way to accommodate more students in the course, which is a mixed blessing, because that means that we will have the opportunity to have another class next year, which we are planning to do in the next calendar year to make sure that we meet this demand for law students to learn these so-called cross-disciplinary skills and be better prepared for the future. So that was something that we are actively preparing for next year.

Monica Bay: Another thing that I thought was very, very interesting was the location that we were in, because we were not in the law school, we were in the D School, the Design School. That environment was so open and so airy that I think that that makes a big difference compared to trying to pull that off in a traditional law school venue. What triggered that for you to get involved in that and to connect with that aspect of it?

Jay Mandal: So we were very fortunate, my co-organizer Jose Torres actually introduced us to that venue, and it goes with our theme of cross-disciplinary thinking that we chose this venue outside of the law school, which is the Center of Design at the Stanford Campus, as a way to introduce law students to a different environment, to think differently. And that whole venue and the room and the way it was set up and the collaborative environment I think fostered and facilitated kind of the success of these law students in building businesses in areas they had no idea about before they came to the course.

So I hope that in our future classes we have the chance to also choose other venues to create, not only intellectually, but also physically the idea of cross-disciplinary environment.

Monica Bay: Absolutely. Well, I know we are running out of time and we could talk forever on this because we are both so passionate about it. And Jay and I sort of mutually put together a very, very long post on the CodeX blog, if you are interested in the link you can reach me at  HYPERLINK “mailto:[email protected][email protected] and I can send you the link. Again it’s  HYPERLINK “mailto:[email protected][email protected].


We are running out of time my dear friend, is there anything else that you wanted to share before we say aloha?

Jay Mandal: No, it’s great to have this conversation with you and share this experience with the listeners. I think the idea of this Startup Bootcamp for Lawyers I hope is one small effort toward the bigger idea of trying to help law students become better prepared as 21st Century lawyers. And my hope is that we have more courses like this that teach these cross-disciplinary skill sets like product design and beyond in order to help lawyers be more entrepreneurially-minded and meet the demands of clients who are technologically savvy.

It’s not only for them, but it’s for lawyers, because lawyers down the line, they could be thinking about practicing law, also going in-house at these tech companies and even starting companies themselves. So I think efforts like these and more efforts like these will be necessary to be more responsible as legal educators.

Monica Bay: Well, I can’t agree with you more. And before I let you go, would you let our listeners know how they can reach you if they would like to.

Jay Mandal: Absolutely. So they can reach me via email at  HYPERLINK “[email protected][email protected] if you want to discuss the ideas about legal education or you want to talk about legal tech ideas and how we can push this whole area forward.

Monica Bay: Well, I was so delighted to participate in it and very, very, very much appreciated it. Every time we get together good things happens, so let’s keep it going again.

Jay Mandal: I agree.

Monica Bay: At least on my end. I was just so absolutely delighted to be able to participate. It was an amazing situation and I would encourage everyone to look into these, and there’s other ones going, it’s going to keep getting better and better and better.

So with that, thank you very much and we hope you will visit us on the next issue of Law Technology Now.


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The views expressed by the participants of this program are their own and do not represent the views of nor are they endorsed by Legal Talk Network, its officers, directors, employees, agents, representatives shareholders, and subsidiaries. None of the content should be considered legal advice. As always, consult a lawyer.

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Episode Details
Published: May 30, 2017
Podcast: Law Technology Now
Category: Best Legal Practices , Startup Law
Law Technology Now
Law Technology Now

Law Technology Now features key players, in the legal technology community, discussing the top trends and developments in the legal technology world.

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