Neil Patel

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Jai Shekhawat has built, funded, and sold companies. Now he’s investing in and advising other entrepreneurs on their own ventures. His startup, Fieldglass, has attracted funding from top-tier investors like Madison Dearborn Partners, SAP, HLM Venture Partners, and Grotech Ventures.

In this episode, you will learn:

  • Testing and validating your idea
  • Risk of failure versus the rewards of trying something big
  • Alignment with your investors and board


For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) that I recently covered. Thiel was the first angel investor in Facebook with a $500K check that turned into more than $1 billion in cash.

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The Ultimate Guide To Pitch Decks

Moreover, I also provided a commentary on a pitch deck from an Uber competitor that has raised over $400 million (see it here).

Remember to unlock for free the pitch deck template that is being used by founders around the world to raise millions below.

About Jai Shekhawat:

Jai Shekhawat serves as Board Member in 1871. He also serves as a Member of the FireStarter Fund. He also served as Chairman at Semantifi.

Jai co-founded Quinnox and serves as its Board Member. He is a Co-Founder and served as Chief Executive Officer at Fieldglass. He served as Board Member at Fleet Complete.

Jai also serves as a Member of the Advisory Board at Method Capital. He also served as Board Member at OfficeLuv and BlueCat Networks. He also serves as Entrepreneur Partner and Advisor at Chicago Ventures.

Jai has more than 20 years of experience with software development, information technology, and management consulting. He is ranked 7th on SI Review’s 2010 “25 Most Powerful People in Staffing.” He is also a two-time Supply & Demand Chain Executive “Pro to Know” and currently serves on the Mayor’s Council of Technology Advisors (MCTA) for the City of Chicago.

Jai is a regular speaker at industry conferences and has been profiled in publications such as Silicon India, Entrepreneur, and Chicago Tribune. Under his leadership, Fieldglass received a Stevie Award for “Most Innovative Company in North America” in 2007.

Prior to starting Fieldglass, He was a Co-Founder of Quinnox, an IT and Business Process Outsourcing firm located in Naperville, with development and sales operations worldwide.

Previously, he was a strategy consultant with McKinsey & Co. in Chicago, where he served clients in various industries in the areas of corporate strategy, sales effectiveness, marketing, and cross-border alliances.

As head of operations at Syntel, a software services firm, he helped build the company to nearly 700 consultants as well as create an international sales and service delivery organization to provide application management services to the Global 2000.

Jai holds a master’s in business administration with specializations in finance and strategy from the J.L. Kellogg School of Management at Northwestern University in Evanston; and a bachelor’s degree in management science from the Birla Institute of Technology and Science, Pilani, India. He serves on the Board of Directors at Signal. He also serves as Advisor at StarVest Partners.

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Connect with Jai Shekhawat:

Read the Full Transcription of the Interview:

Alejandro Cremades: All righty hello everyone and welcome to the deal maker show. So today. We have a really interesting founder. You know we’re going to be learning about coming to the us about building about scaling about financing about exiting all the good stuff that we like to hear so without. Waiting any longer. Let’s welcome. Our guest today Jay Shekawa welcome to the show. So originally born in India so give us a little a walk through memory lane how us live growing up there and then also being in a family that is involved with the military.

Jai Shekhawat: Thank you, Thank you alandro.

Jai Shekhawat: Yes, I was born in the city of Jeor in Northwest India it’s a desert town. Um and born into ah a military family. So my father was in the navy so we moved around a lot most of the. Most of the time when the coastlines of India but as a child also lived in the former Soviet Union my father was a submarine officer then and I think at the age of about 4 or 5 we lived in Moscow and then vadivostok and then upon coming back to India. When I was 14 my father was posted to the naval war college in the United States and that got me put into boarding school in New Delhi a place called the Delhi public school which is really sort of the last time I lived at home. So so it’s it was good I have only the best memories of growing up in that environment.

Alejandro Cremades: And obviously you know like moving around making new friends. The unknown your certainty. How do you think that they you know made who you are today.

Jai Shekhawat: Well I you know upon reflection I think it probably had quite a big impact because when it’s happening at the moment. It’s quite Disruptive. You know you’re young, you made all these friends and then you have to go to this new place and you’re not easily welcomed et cetera. But I think I learn to become. Quite independent and quite resilient and probably developed a pretty rich inner life with lots of reading and a love for sports actually eventually individual sports which you know we can figure out what that means but I was very much drawn to racket sports in particular squash. Tennis Raquetball. That’s something.

Alejandro Cremades: So in your case, you know you ended up you know going to school and and and that you know 1 thing led to the next and you ended up working at this company called Tata and. As a result of that you land all of a sudden in the us. So how was that transition like and and how shocking you was to all of us sudden and be in the land of opportunity.

Jai Shekhawat: Well, you know at the time it was happening I didn’t know any of these things so when I finished when I finished college at the age of 22. The only job offer that I had was from the phillips radio company and. It was to sell radios in the interiors villages of of India and that’s about all I had and you know my father ever the optimist said something to the effect that while you’ll at least get to know your country. Ah, and so I was within days of accepting that offer. When just by complete chances ran into a friend who was going to do an interview at this new company. Ah called Tata borrowrows. It was a joint venture between the ta company and the burrowers computer corporation I showed up there. 1 thing led to another I got an offer as ah as a computer programmer it was coil back in those days. And we knew very little about computers other than some classes that we took in college that involved working on a mainframe ah where the act of programming was really you know putting holes in punch carts and then stacking them and handing them to a computer operator who sat behind this glass cage. In an air-conditioned room and that was my experience with computers but lo and behold few months after joining I find myself being shipped to Atlanta Georgia where I showed up, you know in the mid 80 s with the 2 or 3 other people so it was a complete adventure.

Jai Shekhawat: I had no idea what to expect? You know my the first time I heard I was going to Georgia I thought it was Soviet Georgia which is the only one I knew back then and I think people corrected me and said no we think you’re going to Atlanta georgia not not not Soviet Georgia

Alejandro Cremades: Now now in this case for you I mean you you enter this really nice path of you know the corporate world in the us you know, having the um, the 9 to 5 um, the land of opportunity as we were saying you know earlier. But. After a few years you know, ah data then you did Intel then you realize that it’s time to shift gears and you do your and Nba program. What why did you decide. It was the right time to do an Mba at that point at Kello.

Jai Shekhawat: You know I stayed um in the it services business withintel ah for 5 years and it was a wonderful experience because the founders husband and wife team that I’m very close to to this day had really pioneered. The business of it services the offshore business e so and built a very substantial firm over the course of you know, a couple of decades I was there relatively early for about 5 years I learned a lot. Um, what it also taught me is what I don’t know. So with the complete support of of my then boss his name was baratteai um I ended up applying to business school and got into a few of them and I chose northwestern here in Chicago which is the kellock school of business so that was really the reason you know to expand on. My then relatively rudimentary experiences. You know most of them involved. You know one sector heavy on sales heavy on learning about entrepreneurship. But in hindsight I can just say unequivocally that it was an excellent move.

Alejandro Cremades: You know, kidding and in your case you know a career shift too because then you went into consulting you know is he solving problems to then solving your own problem with your first company. So how were how was that transition of events you know going from graduating to now you know you are. Mckinsey where you’re learning how to grab 1 big problem divide it up into small little problems and tackling one after the other to then hey I think I I have what it takes you know to to go at it and and start something on my own. Yeah.

Jai Shekhawat: You know the thing about joining Mckinsey which was completely. You know my dream at that stage. Ah and it was it was difficult to get into they were they were quite selective. It was hard to even get an interview. So I think I got lucky on several fronts there. Mckinsey back then was often referred to as getting a ph d in business. You know, metaphorically speaking and I would say for I stayed there for just under 3 years including a job as ah as a summer associate so it was ah it was a marvelous experience. We worked in these intense situations. And really got to take the Mba the you know the learnings from an Mba and put it to some sort of practical use. But you know 3 after 3 years went by the bug of entrepreneurship that I had that had been planted in me when I worked in Michigan with Satel. That had started to surface again because I I really wanted to get my hands dirty once again with operations. Um, and you know consulting at the end of the day if you’ve been in operations it it feels incomplete and there was there were several moments on different studies where I felt I would have liked to. Stay and continue to see this work through and you know build it out and run pnls and build a salesforce and you know bring on a team and that sort of thing and that’s what eventually led me to decide that it was time to leave but I’ll always credit mckinsey with just giving me the frameworks and the.

Jai Shekhawat: And the sense of confidence to go you know break down these big problems that you see if you leap off and try to start a company. It can seem overwhelming but but the stint at Mckinsey gave me the confidence to feel like I could tackle those.

Alejandro Cremades: So Then let’s talk about that the confidence because then you know Quinnox you know is what comes really? you know on the light of the day here. You know obviously the most immediate step to building your biggest success story which we’re going to get just in a little bit but. How do you get into quinnox.

Jai Shekhawat: Well Quinox which was actually originally I t twenty so the term quinox. It’s a merger of IT twenty and another small firm that a friend of mine had started. It was ah you know, frankly it was the only type of business that I really knew which was it t services. And you know it offered an opportunity to do on a small scale. What I had done backets and tell so I I jumped into that but I learned a couple of things very quickly that I had changed. You know myself and and what I really wanted to do is build product and not. Be in the services space and so you know within a year of starting that I handed that off to a couple of friends of mine that continue to run it and then I started field glass which I have to say was um, the. Probably the fifth company in that space to begin and and.

Alejandro Cremades: And but but 1 thing 1 thing really quickly there I mean quinnox is still up and running today and doing pretty well if I understand right? How many employees that that does the company have.

Jai Shekhawat: Yes, that is correct. You know I don’t know anymore because I’m not involved I was on or there for a very long time. But yes, the firm has done well and hopefully.

Alejandro Cremades: Yeah I mean we’re talking about thousands of employees if I understand that right.

Jai Shekhawat: Ah, no I don’t think it’s quite that many, but it’s ah it is It should be fairly substantial. It’s probably you know getting. It’s probably close to a thousand but I’m not like this. Yeah.

Alejandro Cremades: I mean that’s impressive. So I guess saying you know Ac company that would end up being so successful I mean looking back I mean do you think that was premature or or or what? what? What did you learn from you know, turning over a ah company that. Would be so successful.

Jai Shekhawat: Ah, no, it wasn’t premature at all actually because what what I did is the couple of friends that were running that we I gave them some equity in field glasss and in exchange I kept some equity in quinox and so it was all done on the basis that. You know back then these things are very small and the theory was look the chances of you know, even 1 of these succeeding statistically is quite remote and so let’s just set it up. So if even one of them succeeds then you know we’re going to be okay so that was the basis of it. Ah, and like I said. Ah, you know my heart really lay in solving a big new original problem and that’s when I started to write the business plan for field glass.

Alejandro Cremades: You know I mean pretty impressive stuff here Jay so tell us about field glass because for you to be running a business and then you know, really understanding that. There’s something much bigger for you. A bigger calling a bigger problem. You know something that you are that you can’t take over out of your head to the point where you are turning over you know the the operation that you’re in and and really venturing into something new. What was that level of conviction. How did you get that level of conviction that that was the right path. To take on at that given moment.

Jai Shekhawat: You know what I started to think is um rather than think about a company where I’m just you know doing something that thousands of other companies are doing which is what it services is could I tackle a problem. In a space that I understand that is such a large unsolved problem that the that the the dangers ah the risks are substantial to failure. But also ah you know the upside is tremendous and something that honestly offers a more interesting journey to me that’s. Criteria I optimize for is will it be a more interesting journey and ah that was the basis for even sort of starting the process of thinking about it and you know in my mind. The real risk is looking back. You know years later you know ten twenty thirty years later and thinking I could have done this and I didn’t do it that to me is a much greater risk than the risk of a business failure. This is failures come and go you know most of the people who have done well have had plenty of failures along the way and I would say even with field class. Even though we ultimately succeeded there were many moments along the way where we we might not have succeeded so that was really the the basis just trying to tackle a very large ah problem of which I felt I knew something.

Alejandro Cremades: So for the people that are listening to to get it. What ended up being the business model of field glass. How are you guys making money there. So.

Jai Shekhawat: So you know at at a very high level. Ah think of a large corporation as having 2 categories of talent 2 categories of workers. There is a category called the called employees and then there is a category called people who are not your employees. And that second category consists of contract workers people from staffing firms independent contractors consultants ITService providers you know all of that and what was becoming clearer is that large is that second group is getting. Bigger and bigger as companies. You know, talk about core competencies more outsourcing. You know if it’s not something that we have to do then we shouldn’t do it so that second group was just getting larger and there was no way for the corporation to effectively manage that group and. You know you could see the evidence everywhere the the things like the bill rates for the same scale were being. You know, not properly understood. There were compliance issues taking place you know on and on and so at that level all all. I thought off was that that second group is going to need some sort of a procurement slash hr platform to manage it and that really was the starting point.

Alejandro Cremades: So I guess say Also what was that the because building a company is not easy. But I guess saying for you All what was that turning you know moment you know where you realize you’re into something here.

Jai Shekhawat: You know I think it took a little while for that. But there was so much evidence that this was a real problem and one of the things I did is I did a lot of interviews so I laid out my thesis on a single page. You know here’s the problem here’s why there isn’t a. Solution then you know here’s my idea and so on and I did as many interviews as I could with people who who knew the space on the customer side and the thing is you know when you don’t have a product. We don’t have anything to sell people don’t mind talking to you because you’re not. You know you’re not pitching them anything I’m like I don’t have anything to pitch and people will give you the benefit of their thoughts and their ideas in those circumstances and it really helped me sort of refine. What I had and it did it validated 2 things for me 1 is that this conception my conception of the problem is very real. This is an unsolved problem and second that if someone showed up with a platform there was they would be you know, ah substantial revenues to be generated from solving this particular problem so that that was my naught star and it gave me the confidence to then. Raise money and build out a team and I’ll tell you you know, building out a team. It’s an act of risk. It’s an act of you know you have to be responsible before you ask? Ah, someone to quit their job and join you on this crazy journey because.

Jai Shekhawat: You don’t know where it’s headed and the only thing you can offer them is the promise that you’re solving a big enough problem. Ah you know that it’s worth doing and that’s you know that’s what gave me confidence but it still took a number of years before the market really validated these solutions.

Alejandro Cremades: And we’re talking all the late 90 s here. So um, so.

Jai Shekhawat: Well, this would ah this would have been effectively early 2000 so in fact I was sitting with an unsigned term sheet the day. The internet you know the early internet market crashed in 2000 it was March twentieth of 2000

Alejandro Cremades: Yeah.

Jai Shekhawat: Which actually happened to be my birthday and also the birthday of my chief technology officer who was my first hire. So the 2 of us sitting sitting there with an unsigned term sheet with yeah.

Alejandro Cremades: So what? What? what? what was like going through through that downturn in the market. Yeah.

Jai Shekhawat: You know it was ah it was it was difficult but we managed to get that round of funding done now we had to take terms at that stage that weren’t you know the prettiest but we got the funding done and I learned 2 things.

Jai Shekhawat: 1 is how to make money lost as as much as you can because it is scarce. It was hard for us to raise the cash and we found ways to make it last you know we we stretched it quite a bit. The second thing I learned is that the market this. When a downturn happens. It’s only people who are really serious about building something that remain all the dilettanes and the folks who you know just thought it would be a good idea. All of those people leave because it gets really hard so there is some advantage to building a company.

Alejandro Cremades: No kidding now you were talking about it. You know getting the term sheet. How much capital Do you guys? raise prior to the private equity firm. You know coming in. Okay.

Jai Shekhawat: And a downturn.

Jai Shekhawat: We had raised 38,000,000 over the course of 4 rounds and ah yeah, so that was the and that took ah probably 7 years over the course of 7 years to raise that money. And then the private equity firm which was Madison Dearborn Partners came in in October of 2010 and we essentially did a recap off and bought out the existing investors and so on. So yeah, that’s how long it took.

Alejandro Cremades: And why? why did you go from Vc to p you know because that’s ah, interesting transition there and and obviously a different way of um of dealing with an investor and I am sure that you know people that are listening. They’re probably more used to the Vc and. I think that that transition from Bc to b is quite interesting. So can you walk us through that.

Jai Shekhawat: Yes, of course you know in some ways we could have just stayed. We didn’t have sold. The company was profitable at that stage. In fact, the final vc round that we raised I think was ten or eleven million and off that we never spent more than you know 1 or 2 so. Our bank balance at that stage never dropped after that round less than I think 9 if memory serves me right? So we could have continued to build a business but you know at this point there’s the consideration that most of these venture funds have been in the business for a long time and some of them are running. To the end of the fund life and so they were looking for liquidity. So I think in large measure it was driven by their need for liquidity. Ah as opposed to the businesses need for additional funding.

Alejandro Cremades: And I guess you know for you. Also what has been a lesson you know learned because I know that they receiving that pressure of vcs that are. Looking for liquidity you know versus where you’re at to and what are your interests and your passion you know sometimes you know there is some type of misalignment there. So How was that for you.

Jai Shekhawat: You know there’s always I would say in hindsight I was lucky to get a good set of investors that doesn’t mean there wasn’t disagreement and you know the disagreements were often around what are we spending the money on how much we should raise and you’d often get conflicting. You know inputs there were when things were going well people would want you to spend more but you know when times were tight, they’d want to pull back but operationally that becomes very difficult when you made commitments to people etc. So I think one of the lessons for me is is actually just to be more tempered with the spending. So my bias you know back in the early days today I sit on a number of boards and so on and the the behaviors are quite different. There’s a lot more money available today people are you know at least until this relatively recent downturn people are willing to put lots and lots of capital at work. My views were old fashioned. But today’s standards I think you should try to build a profitable business as quickly as you can um and that would remain you know that would remain my position.

Alejandro Cremades: Now in that in that sense when the private equity comes in. You know you guys structure this as a minority investment so there was first the need the first tranch of money you know where where you guys were selling that minority ownership. And then you know as it happens with these types of deals. You know you retain certain amount of equity as well as the team members and so forth and then you know you would do um another transaction where everyone is is really you know, liquidating their position in full. So can you walk us through you know how those ah ah. Structures or transactions you know were actually how how did they happen and and what was the value.

Jai Shekhawat: Well the the deal with Madison Deo Born Partners was again going by memory approximately 220,000,000 and since we had only raised you know 38 and still had a lot left that was a. It was a pretty good return for everyone concerned, especially the early investors you know, given the vintage of the funds which were raised in the year two thousand you know this was a good return so people were people were quite pleased as far as our employees and management team was concerned. We. We took some chips off the table just because it had been a while but everybody at this point really believed in the firm and far exceeded whatever was required by the new private equity firm coming in and so we kept our money in um, and. Then you know things things actually became really good. So we started to ah you know one statistic that will be interesting is it took us approximately seven or eight years to close our close about 40 customers. And these were large firms you know fortune 500 firms. It was pretty global already. But then when the recession hit which I think was in 2008 in that one year we closed 40 new deals and it was the proverbial hockey stick and all because in that recession you know in times.

Alejandro Cremades: Wow.

Jai Shekhawat: Recession companies start looking at cost cutting tools instead of revenue generating tools and we were sitting there as a platform that could help a large company control costs on service spend and so all of a sudden there was just this wave of adoption. And it just accelerated so 40 deals that year that I think we did 60 and then eighty and you know then I think we did over a hundred new customers in a single year and for the private equity firm. This company was making its first bet in the world of software. They. They were more focused on industrials before so it turned out to be very good and then eventually we were acquired by sp just you know little over three years after that transaction and at this point, the firm was extremely profitable it on the on the rule of 50 we were. 70 or 75 so the farm was growing. You know 35% a year had nearly 40% ebata margins. It was just it was just a very good business at that stage and I would just say as an aside though, if there is such a thing as a work of art in the world of business. It would be a great business model that can stand up and essentially become your highly profitable. So yeah.

Alejandro Cremades: So so so what were the what were the terms of this transaction then you know the second time around with this a b.

Jai Shekhawat: It was ah approximately a billion dollars so it was one of the first tech unicorn exits in the midwest of a privately backed firm.

Alejandro Cremades: J a billion is a lot of Zeros you know any? what was you know some? yes bill the bins here. What were some of the things that you did you know? Obviously you know after this transaction that they that you couldn’t do before.

Jai Shekhawat: Ah, to to be to be honest is is going to sound a bit syrupy but 1 of my first acts was to to buy a home from my my parents could live in in bombay at a place that I could visit so that was really sort of the.

Alejandro Cremades: Wow, That’s amazing.

Jai Shekhawat: Only substantial purchase I don’t I don’t really like to own that many things that so I might have bought a New Paris new set of squash rackets and some new squash shoes but really nothing nothing more.

Alejandro Cremades: That’s amazing I’m sure there were there were very good shoes on very good racket now in your case you know, obviously an amazing chapter here that they that you were you know closing in you know after the acquisition with with sap what happened next for you. You know you’ve been now you know for the for the past few years you know, really you know getting involved with boards you know making investments. You know what what What has been this next chapter for you.

Jai Shekhawat: So you know one of the things that I learned is when you’re going to leave a journey that has been that intense and that long you know nearly fifteen years from start to finish. You have to prepare the landing strip so that you don’t end up with you know, nothing to do. So that was good advice and the way I started thinking about it. So I stayed with essay for a year and a half this a marvelous farm just you know great experience. Everybody bleeds blue there you know shows up for conference calls. You know 3 minutes early whereas a field glass. It was always 3 minutes late so that was a reset but I decided to. Think about life as a portfolio as opposed to a job and I didn’t want to go back into you know one more ant hillll where your entire world is consumed by just what happens inside that 1 antil and that’s what a startup is you are. 24 by 7 in 1 little thing so I decided to think of it as a portfolio so rather than you know allocating dollars. It’s a question of allocating your remaining you know hours, you know so to say hours and weeks you know and months of your life. Um, and. So I broke it down into I think what I’m good at is I can I can see how problems so solving problems can be translated into businesses you know which is the core act of entrepreneurship. So I love working with entrepreneurs. So I invest in a lot of them I have dozens of such relationships.

Jai Shekhawat: You know and some will fail and others will hopefully succeed but it allows me to to be involved in the act of business creation without being that person getting on that you know 6 a MSouthwest flight out of midway. Um. So there’s that set of activities I have a great deal of sort of personal learning interests. Ah I’ve been a mentor for duality which is the country’s probably only quantum computing accelerator illinois has become a bit of a hotbed for quantum computing because. 2 of the Nsf grants came to Chicago to Argonne and fermil labs and there’s University Of Chicago so it’s been really a good sort of a learning experience. You know, thinking about that. Um, and then I’m involved in a number of funds I chair one of the industry roundtables for Madison Dearborn partners and that involves sitting on some boards there I’ve been a trustee with the field museum of natural history for probably twelve years now and I like going into the field with the scientists so we’ve made trips into Madagascar I’m going again into Guyana into Peru Africa so that’s.

Alejandro Cremades: So you you experienced now the board from two sides you know that they will you know from the side of being the operator being the founder being the one that is executing now from the side of being someone that coms you know provides a strategic guidance. You know shares your opinion you know on on how to handle.

Jai Shekhawat: But my life is now.

Alejandro Cremades: Certain problems. So what are your thoughts on effective board dynamics What does that look like.

Jai Shekhawat: Um, you know that’s a good that’s a good question ah I would say the boards that I’ve enjoyed the most is where the board remembers that it is not working inside the firm. It’s not working inside the company it’s working on the company and ah great relationship is where the Ceo you know sits on the boundary of those 2 and is spending their whole day working inside. You know, selling talking to customers. You know, handling problems building product that sort of thing and when they bring it to the board they are presenting a picture that is a dashboard of the daily activities that are going on there. And then the board’s job is to help bring what they know of the outside world and different experiences. You know to the table when that happens well in a in a trusting way then you have excellent board dynamics and I felt like I had that in my final stint with Madison Dearborn where I will completely credit them with finding the right time to exit the business in its final sale because they started to pick up signals in the market that I would have never seen you know because we were heads down on building our business. So ah. It is that the my second point would be the board has to be a combination of of sponsors so investors as well as operators and then you can have a healthy discussion that factors in both I think if it’s only so financial sponsors then you’ll get a board that is probably.

Jai Shekhawat: Going to be a little bit difficult for the Ceo. So yeah, so those would be the few.

Alejandro Cremades: Got it now. There’s probably a lot of people that are listening you know J right now and and that are wondering you know hey how can I get in touch with J you know So why will be the best way for them to reach out and say hi.

Jai Shekhawat: Um, they could probably drop me an email and that would be at JRAndEY 1 2 3 at

Alejandro Cremades: Amazing. Well hey Jay thank you so much for being on the deal maker show. It has been an honor to have you with us today.

Jai Shekhawat: Thank you very much alandro. It’s been a pleasure.

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