Chirag Gupta

Chirag Gupta


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Venture Capital | Startup Mentoring | DeepTech

Asking the right questions to structure thinking – Chirag Gupta

“What works very well is not necessarily to share the knowledge but to use that knowledge to ask the right questions to the startup. To help them arrive at a conclusion is more powerful than sharing my knowledge with them.”


Chirag is the Managing Partner at 8X Ventures, a Deep-Tech focused venture capital firm. He invests and enables startups that will lead disruptive innovation and create sustainable value.

Prior to 8X, he has held leadership positions at 500 Global (most active early stage Venture Capital firm with $1.8+bn AuM), Careem (MENA’s first unicorn acquired by Uber at $3.1bn), McKinsey (best management consulting firm worldwide), PwC/Strategy& and Korn Ferry. During these experiences, he helped 10+ corporations build their unique startup “explore” strategy, helped multiple startups grow to unicorn status, and partnered with govts of 8+ countries to grow their startup ecosystem.

Chirag holds an MBA from University of Chicago: Booth (#3 top MBA globally) and Nanyang Business School (#5 top MBA in Asia-Pacific). He studied Business Analytics at Harvard University (with Harvard scholarship). He also received 100% scholarship for his Bachelor degree in Finance from Faculty of Management Studies, Delhi University.



Chirag Gupta

The full #OPNAskAnAngel talk

Jeffery: Welcome to supporters fund ask an investor I’m your host Jeffery Potvin let’s please welcome Chirag Gupta managing partner at 8X Ventures as our investor for today welcome Chirag it’s a real pleasure having you join us.

Chirag: Thank you Jeffery uh thank you for having me on your podcast and I am very excited about talking about us and I’m Sure they lose some opportunity to talk about you I would love to know more about you and yes but let’s Dive In.

Jeffery: I love it well I’m pretty excited too chirag because only a couple times in in all of the podcasts that we’ve done that. I love it well I’m pretty excited too chirag because only a couple times in in all of the podcasts that we’ve done that we’ve actually had the opportunity to talk deep Tech and that’s what gets me excited because it’s not really a common subject and I think from all of the different YouTubes that I’ve listened to on yourself that they’re you’re in the same boat and you feel the same way that there isn’t really a lot of people diving into deep Tech because of the lack of understanding and background so we’re pretty excited to be able to dive in and talk a bit more about that but before we start and the way we love to start is that we want to learn a bit more about yourself so if you could maybe give us a little bit of your background I know that you’re well educated you’ve done a lot of things in school and and have a lot of that and I think it’s really defines a lot of things as you progress and then all the way through to your startup and obviously McKinsey analysts just give us the real deal and then one thing about you that nobody would know.

Chirag: absolutely let me talk about the my academic career so I I studied in India and for my bachelors I studied business management and so honestly I wanted to study engineering but somehow I ended up with business management I still can’t remember why but the college I went to is the best college to study undergraduate Management in India um which is under university of Delhi after I graduated from there I went to join McKinsey in India and I spent three years working in at McKinsey amazing experience the amount of structured thinking McKinsey teaches you is unparalleled and a lot of problem solving skills they taught me are still useful suppose that I I went for my MBA where I went to a Technological University called nanyang Technological University and I did a a dual degree with University of Chicago Booth School of Business so very very exciting Place both the universities a great place to learn then I continued on my Consulting career uh post my MBA and so overall I did about 11 years of Consulting and about half of my time was uh was spent on doing consulting on Startup policies startup Frameworks and startup governance to help governments across different countries set up those policies especially in India especially in Asia actually and I say this because the the in the last 15 years a lot of governments in Asia hired Consultants to figure out how to build and nurture a startup ecosystem us was definitely ahead of the curve a lot of best practices from San Francisco were very useful but a lot of local practices have have to be built to develop and nurture the ecosystem so I spent about 10 11 years doing that so I I did about 11 countries doing that uh two of my favorite experiences happen in Singapore and Saudi they both have a very extreme end of the ecosystem but they both have uh have have very very unique strengths when it comes to pulling the startup ecosystem and they’re doing it very differently post my Consulting career uh I went on to join a company called Kareem which was uh the Uber of Middle East uh and I’m using the definition uh which was used about five years back a very exciting place um and so we we were the first super app and the biggest tech company in the Middle East I was a strategy director for the global strategy uh strategy and I looked at the certain areas of Finance as well and uh we got acquired by Uber then for about uh 3.1 billion dollars very very exciting Journey um and it was a great experience because we became Uber after acquisition um I moved to this company called 500 startups which is a global VC firm uh based out of SF and about two billion dollars uh AUM so I was part of the Saudi team very exciting on um looking at this of the overall Mina ecosystem sitting in Saudi and in January this year uh I together with a billionaire and to the multi-millionaires started this company called Eight expansions which is a deep Tech focused uh Venture Capital firm so that’s a long uh introduction uh that I that kind of covers both academic and non-academic side of it you asked me a question on one thing that almost no one knows about me um and there is something very exciting which I did and I’ve been very fascinated about it so I loved coding and I’ve always been fascinated with technology when I was eight years old I coded my first computer car race game and this was in 1994 when the computer technology was at an early stage in the programming languages used to be dos and basic and Lotus so I used uh those programming languages at that time to build a very simple car race computer game and that is I I personally was very happy about it uh because a lot of people I knew did not even have computer at that time I had a computer I built a computer game and I used it uh so that was probably the first time first uh in interaction that I had with the technology and I wasn’t successful about it.

Jeffery: That’s awesome great story um we have uh certainly a lot of um a lot of stories from from our early uh laptop computer uh man I’m trying to think of uh um the Intel side of things so many stories from from back then as well and it really kind of shows that how infancy the market was in but how exciting it was when it was just such a trouble shooting kind of process back then on trying to figure out how to get a modem to work or coding and how getting that to work on the screen with the modem being super slow and all these other things that you were trying to achieve so it makes it a lot more exciting especially when you share the stories um very nostalgic and brings back a lot of old memories so it’s pretty pretty exciting so I want to kind of take back to your time when as you mentioned you’re doing all this all this school and then you jumped into the Consulting side and you jumped in as an analyst and I know that um McKinsey and all of these great platforms I think what’s really exciting about them is that they they do teach you a lot of um process problem solving and how to get in and understand things before they become blown up and kind of get into a spot where things don’t work properly but you’re able to analyze them and I find that a lot of people that do get into the banking sectors legal side they tend to have a really strong understanding of how startups work and your approach that you went into gave you a lot of years of startup experience as you mentioned and globally can you share a little bit about how that structure actually has helped you today when you’re looking at companies and I I reach back to this because a lot of what we do in our past shapes our future and I see that a lot of that understanding is um pretty powerful and and I’m sure back then you weren’t thinking you were going to be a startup but what kind of things could you say that you took out of that and would you recommend that any any person that’s coming out of school to jump into this type of process to learn before jumping into a startup and what your thoughts are around that.

Chirag: So for anyone coming out of the University I very very strongly recommend going into uh some of the Consulting homes especially some of the top consulting firms and and same applies to the top banking firms as well and I say that because the even if you spend let’s say a year over there the kind of structure thinking that they teach you is very unparate I I think I learned more from my Consulting time than I learned from my MBA I learned more about my business management from Consulting then I learned by paying probably 200 000 to University of Chicago and to uh Technological University um and that that structure is very important to the startup ecosystem because if you realize one of the fundamental issue on why there is a winter coming the startup winter coming why there are layoffs happening and uh in some cases uh of course these genuine cases in a lot of cases it’s a it’s a business model flaw and if you think about especially uh let’s talk about fintech the in a lot of cases your business model itself is flawed it’s not meant to make money so now if your business model is not meant to make money you need to start thinking early on that what is going to be the source of your your Revenue it cannot be a venture capital fund or it cannot be Sequoias of the world it has to be it has to be the business model has to be strong itself to sustain and build and grow itself and that that learning I still carry because when we go into a due religions process for me as an in