Gautam Gupta On Co-Leading A $460 Million Fund Focused On Consumer And Enterprise Startups

Gautam Gupta has gone from VC investor to startup founder and is now back to investing in other entrepreneurs. His $460M fund is open for business and may be one of the few actively looking to fund good startups right now. The fund, TCV, has invested in companies like ByteDance, Cognite, Celonis, and Klarna.

In this episode, you will learn:

• What the Velocity Fund is looking to fund right now
• How TCV helps founders grow their business
• How to get in touch with Gautam
• His top advice when launching a business

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About Gautam Gupta:

Gautam Gupta serves as General Partner at TCV. Mr. Gupta served as Partner at M13. He serves as Board Member at PrizePool. He served as Board Member at NatureBox. Previously, he served as Chief executive Officer at NatureBox.

Gautam focuses on investments in the consumer technology space, including commerce, consumer-facing healthcare, education, software, and financial services businesses. He serves on the board of directors at Grow Therapy and Passport.

Most recently, Gautam was a Partner at M13 Ventures, an early-stage venture capital firm focused on consumer technology, where he led investments in the marketplace, consumer subscription, and B2B2C models.

Gautam started his career at General Catalyst in 2004. He was initially an intern while in college and later became a member of the investment team.

He left to launch NatureBox and, as CEO, helped build the company into a nationally recognized brand with millions of customers.

Gautam has seen the highs and lows of entrepreneurship first-hand, which greatly influences the collaborative way he works with founders. He is a graduate of Babson College, earning a B.S. in Business Administration.

Connect with Gautam Gupta:

• Crunchbase
• LinkedIn
• PitchBook
• Twitter

Read the Full Transcription of the Interview:

Alejandro Cremades: Alrighty hello everyone and welcome to the deal maker show. So today. We have a very exciting guest. You know I guess that has been on the investment side has been on the founder side now back on the investment side. So we’re going to be able to really hear you know from both sides of the table especially when it comes to early stage so without farther ado let’s welcome our guest today Gautam Gupta welcome to the show. So your parents came from India you know immigrants.

Gautam Gupta: Hey thanks for having me. It’s a pleasure to be here.

Gautam Gupta: Um, for me.

Alejandro Cremades: You know I’m an immigrant Tomb. So I Know what that looks like you know I’m sure that for you was quite inspiring and and you know I’m sure they had to work a lot. You know, just like all the ones you know of us that we come to this Country. So I Guess what was that experience. You know, growing up, give us a lot of a walk through memory lane I’m sure that you found a lot of inspiration from your parents too. So tell us how was life growing up and.

Gautam Gupta: Well I did find a lot of inspiration for my parents. So my dad moved here first in the early 70 s and and you know I often think about just the the juxtaposition of our generation with his generation when he came here. He. Told us that you know often he would have to skip meals because you know they just didn’t have enough money to to you know, feed himself every day. Um, and if if I think about you know in our generation. We never have those struggles right? Um, and so. Ah, it’s it’s definitely an inspiration for me. Um, you know my childhood I would say um, was very much influenced by um, not just my parents but also grandparents. Um who are still in India or were still in India um, both my ah. Grandfathers on my dad’s side and my mom’s side had been entrepreneurs. Um and ran their own businesses in India and so from a young age I was always exposed to business. Um, that was sort of the dining room conversation and so. You know I kind of picked that up and I was always the kid with something to sell I always had something that I was selling out of my backpack in the playground or you know online in high school um and and was always really interested by.

Gautam Gupta: Business and and startups and and and technology.

Alejandro Cremades: And and probably that’s there. What got you to Babson now Babsson The University you know, really known for entrepreneurship. So.

Gautam Gupta: Yeah, so I hadn’t heard about babson until I was in high school and a family friend told us about Babson he had known that I was really interested in in business I went there for a college visit and fell in love with the place and so I decided to apply to Babson. Um, and I would say that that probably that 1 decision changed the course of my life more so than any other because it was at babsin that I started getting involved in the entrepreneurship activities on campus and through that when I was a sophomore of Appsin I met the folks at general catalyst. Ah, and they offered me an internship and so when I was a sophomore in undergrad I started interning for general catalyst which was still a very young firm at the time I mean the firm was maybe 4 years old I think investing out of the third fund at that time. Um, which. By the way at the time we thought it was a huge fund. It was a $300,000,000 fund I think ah general catalyst just announced that they’re going to raise 5,000,000,000 for their next fund so you know times have definitely changed. Um, but it was incredible opportunity and that shaped the rest of my career.

Alejandro Cremades: And obviously you joined them after graduating and you were there for about 8 years but you were that kid selling. So what really sparked the interest you know on the investment side of things. So.

Gautam Gupta: Well I always thought that I would be an investor for a couple years and then I would go back to starting a company or maybe join a portfolio company. You know that that dream and vision that I had of of running a company. Um, and. You know a couple couple things kind of changed for me one is I realized how much fun the job was ah and being able to meet entrepreneurs and see them build companies was incredible. Fun. It was really inspiring the team that I was working for at general catalyst if you think about kind of the founders of the firm. Had all been entrepreneurs themselves and so I felt like I could learn a lot from the business experiences that they had and then lastly you know what I didn’t realize about the investing world. Ah when I first joined was how much of the venture capital job is really a sales job. Um, and and I love that aspect of it of being in front of you know what? I would call the customer as the founder ah and convincing that that customer who has many options in the marketplace why they should go with you. Um, and and are really fed off of that. Um, you know the competitive dynamics of of the industry and and really enjoyed that part of the process as well.

Alejandro Cremades: And when we’re talking about like finding that customer or selling to that customer I mean there’s this thing called pattern recognition when it comes to the investment side to being a Vc and how do you go about finding that customer that you want to go and and sell to an. Ah, what point do you are like you’re like you know what? this I really got to get you know to invest in this company right.

Gautam Gupta: Yeah, the you know the funny thing is the longer that I’ve been an investor I’ve I’ve realized ah how much you have to challenge your own assumptions and how much you have to keep reminding yourself or at least for myself I have to keep reminding myself I don’t know anything. Um, so you know the the thing like I always try to remind myself is the past patterns or paradigms may not be applicable for the future right? And so the next great success. Story may actually look very different from the past. Um, but you know. We were in in those early days of general catalyst. Ah, the the firm didn’t have much of a brand. Um, and so a lot of the conversation or how we were finding entrepreneurs was outbound. We were going out into the market. You know, cold calls going to conferences ah reading a lot of just press and and media right and trying to understand oh this company is you know someone in. Atlanta is you know, getting talked about by the local media and you know seems to be doing something really interesting that could apply globally well, how do we get that person on the phone and and hear their vision or hear their story and so a lot of in those early days was a lot of outbound sourcing.

Gautam Gupta: Um, and and a lot of cold calling. Um, you know the general catalyst model was sort of built after a very prominent firm called Summit Partners who had a similar outbound sourcing cold calling program. Um, so we kind of mirrored a lot of what what they had built um and and that’s ah, a big driver of how we were meeting companies in those early days without much of a brand. Yeah.

Alejandro Cremades: And I got to tell you cold calling is quite humbling you know because you I’m sure you called to a lot of people and they’re like who the hell are you? So So how do you? How do you navigate that you know so that you’re able to really as you were saying you know you didn’t have much of a brand. So.

Gautam Gupta: Um, yeah.

Alejandro Cremades: So what do you do? to? really gain that trust of of of that customer in this case. Okay.

Gautam Gupta: I mean I think it it comes down to you’re always, you’re just trying to find common ground you’re trying to find commonalities between you and the customer um and build rapport right? and so often the lead message that we would have at general catalyst was hey. The firm has been built by operators and founders not financiers and that was you know, very true of the early days of general cows right? All of the 4 founders of of the firm had been very successful ah operators themselves prior. Starting general catalyst. Um, and you know had taken companies Public had exited companies and so that was the lead message right? was hey we’re different right? We’re not like your other investors we have. We’ve been operators and we can help and and that built a lot of rapport in a very short amount of time. With with entrepreneurs that we’re trying to get in contact with.

Alejandro Cremades: So you were there for about 8 years and I’m sure those were very fulfilling years but eventually you realized that it was your time to shift gears and to go to the other side of the table. So what was that moment like and. And why did you think that was the right time to do so.

Gautam Gupta: Well looking back on it. Um I feel like I wish I could have told myself maybe now maybe that wasn’t the right time because it turns out that the tech industry just exploded from there. But you know I had there were a couple things that created. Ah, perfect storm for me. Um I had a cofounder ah someone that I had known from Babson. Um, so I’ve known them for a long time and he and I wanted to be in business together and so we wanted to start something the timing felt right for both of us at that point. Um, where he was just coming out of a venture that he had sold and I was um, you know I had kind of done my tour of duty at general catalyst and I was kind of at an inflection point of either I was going to stay and really commit to you know spending the next eight ten years of my career at the firm or do something else. Um, and and so from that standpoint the timing made sense. The other piece was I had this personal passion around health food and nutrition up until going off to babson I really struggled with obesity. Ah, but. Luckily I learned about nutrition and I was able to lose £70 in six months through diet and exercise. Um and I had always wondered since that experience I had always wondered why the food system in the United States is the way that it is and why do people? um.

Gautam Gupta: Why we have an obesity problem in this country and what can I do to try to help and so I was always interested in trying to build a business around that space. Um, and so just you know things just aligned where my cofounder and I were starting to talk about Ideas. We found an idea that I felt like I could be really passionate about and that was a good business and so it just felt like it was the right time to to make a leap.

Alejandro Cremades: And how did you guys go about testing the idea as well.

Gautam Gupta: So we knew nothing about food by by the way maybe just stepping back. The company is called naturebox and the product is essentially our own brand of healthy snacks sold primarily online. Um, ah. Ah, as we scaled the business. We started selling products in retail stores and that sort of thing but primarily online. Um, we knew nothing about the food industry and so when we were starting to think about this idea. Um we thought well we think this is a good idea. But. Does anyone else think this is a good idea and so we went to a farmer’s market. We bought a bunch of snacks that we thought could be. You know they matched the vision that we had for naturebox. Um and we went back to the office. You know, slapped together. Ah a 1 page website a landing page with a photoshopped picture of the stuff that we had bought at the farmer’s market and there was a buy now button there was you know 4 bullet points of what the you would get if you bought bought the box and then there was a buy now button and if you clicked that buy now button. You would be taken to Paypal where you could paypal my cofounder money right? So it was a pretty messy setup but lo and behold. We started advertising for this website. We got 100 people over the course of a weekend to actually pay pal us money for this product.

Gautam Gupta: Now. The only problem is this product did not exist right? It was a photoshopped image of stuff that we bought in a farmer’s market and so my cofounder and I looked at each other and we said well we have 2 options we could either refund everyone’s money and go figure out how to build this product or. We could force ourselves to figure out how to ship something to these people that had paid for the product. Um, so we said listen if we want to start the business if we’re serious about starting a business. We have to go with the second option we have to ship them something and we thought a little bit about it and we said well where do you get enough? food. To ship a hundred boxes of snacks. Um and both growing up in suburbs the first thought in our minds was go to Costco so we went to Costco we loaded up 2 shopping carts full of Kirkland branded snacks. Um, and we came back to my apartment and we started repackaging the Kirkland snacks into nature box bags and that was the first shipment of boxes that we sent out was literally product that you could buy at Kirkland or at Costco. Um, you know, but but in these branded nature box bags that we bought off the internet.

Alejandro Cremades: And then what was you know that moment to because I mean obviously you also went through some ups and downs with the business. What was that moment like you know where you feel like you’re like running out of cash. You know you’re like with you know, ah well. 1 1 1 ne month left of payroll and and things like that I mean how was that experience too for you. Guys.

Gautam Gupta: Yeah, yeah, so you know fast forward from those early days. We had this incredible growth spurt where we got the business from 0 to 50,000,000 of revenue in 3 years um but we were burning a lot of cash and the venture market had started to sour on direct-to-consumer brands and so we weren’t able to raise another round of funding and we got to a point in lets say this was 20 ah maybe yeah, beginning of 2018 um, where we literally had 1 payroll left in the bank. Our lender had put us in default because we had some outstanding venture debt and you know it was pretty clear that we weren’t going to be able to pay the debt. Um, so we were operating the business under default. With one payroll left in the bank and and look it was an incredible stressful time I mean incredibly stressful. Um, you know I had never managed through a situation like that. But I’ll say a couple things that you know I learned in that experience one is ideas and people are way more durable. Then we give them credit for and so you know I think we as a company people just banded together. Got what needed to be done done. Um, and we were able to keep the business going. Um and and then I would say the second thing is it’s never you know there’s there’s always.

Gautam Gupta: Ways to to you know, figure out even the the messiest of problems and so it took us a little time but we were able to find a new investor to come in and help us do a recap of the business and help you know the business continue to survive and so. Incredibly stressful three month period of time but but it ended up with with a decent outcome.

Alejandro Cremades: So what does it look like when you do the recap of a business for the people that are listening to get it. So.

Gautam Gupta: Yeah, unfortunately recaps are very messy and they’re they’re hard to get done and rare in the venture industry but essentially what you know happened for us was. Some of our initial investors decided hey we don’t want to put more capital into the business where we sort of have reached our limit but we’re happy to essentially sell off our position. Um or be diluted. Ah, if there’s a new investor who wants to come in and recapitalize. You know, put New capital on the balance sheet and so you know there’s a lot of different ways that these things work. Um for us. It essentially meant that a new investor came In. Um, our existing investors had the opportunity to participate in the round if they wanted to some did some did not and so for the ones that did not their equity was diluted. They essentially chose to to you know, not participate in the future of the company. Um, but we’re able to put new capital on the balance Sheet. You know the new investors were able to get a large piece of ownership in the company. Um, and then we’re also able to you know, have enough of um, an option pool and enough stock.

Gautam Gupta: Ah, to incentivize the management team to keep going. Um and so you know very complicated situation but but I think everyone you know, kind of came out with with um you know the the outcome that they had hoped for or or that they had had wanted would happen. So.

Alejandro Cremades: Ah, what point do you realize that you know it’s time to get a Ceo for this and to perhaps you know like look at greener pastures.

Gautam Gupta: Yeah, so I think getting the question of when to bring in a Ceo is incredibly tough and and I think it’s a very personal question for for every founder for me probably in 2017 I realized that I didn’t want to be a Ceo anymore I I sort of felt like um I had learned a lot but the stress of running the business just wasn’t for me I just didn’t want to keep doing that. Um and I also felt like you know there were a number of things that I wasn’t great at. I wasn’t great at management I wasn’t great. You know, ah learning obviously and getting better but I wasn’t great at managing people and and you know really delegating and being focused on kind of high-level strategy I really more enjoyed being in the weeds and kind of. Ah, on the front lines. Um and and so in 2018 once we had had the recap once the recap had been finalized. We were able to find a new Ceo to take the business forward. Um, and and that’s when I decided to go back into venture investing. Um, and and you know my thought process there was I had managed a business through some ups and downs learned a lot in that process of being a Ceo and felt that I could be.

Gautam Gupta: Ah, much more valuable capital partner to the next generation of founders. Essentially I felt like I could be the Vc that I wish I had had when I was running a company and and so that’s what I’ve been doing for the last five years

Alejandro Cremades: And how much capital did the ah company raise.

Gautam Gupta: Raised a total of about $70,000,000 of debt and equity some something like that.

Alejandro Cremades: Got it and it what ended up being the outcome of the of the company because I know it went through an acquisition too. So.

Gautam Gupta: Yeah, yeah, exactly so the company then was later sold I want to say two years ago to a larger tech business called Hungary and it’s still the brand exists today. You know there’s actually. Still team members that were there. Ah from from you know back in 2018 when when I was running a company still still there and and moved along on the acquisition so still around spill operational. It was not.

Alejandro Cremades: Got it amazing and were the terms of the deal disclosed to know okay got it now in this case, you got the Ceo you know you take a look at the what’s next for you and you realize as you were saying Ceo you know was not your thing. So. Going back to venture investing you know, which is what you are excited about doing before you know taking the jump here I’m sure that now with this backro operational expertise. You know you knew that you could be much more helpful to founders. You know, sitting on the other side because you knew exactly what they were going through now in your case what you did is. You went to m thirteen you helped them with their operation. But then while you were doing that you know you you got approached by tcv and that’s where you are now why? tcv.

Gautam Gupta: So tcb I’ve known the folks at tcbforovert decade I have a very close friend here who’s another one of the partners at Tcb But interestingly even outside of that I had pitched Tcb when I was running naturebox and. Um, had gotten to know the partnership ah through that process of seeking capital from tcb ah, and in fact in that process I had met a Tcb venture partner. Ah who ended up becoming my independent board director at naturebox. So I really felt like I had a good appreciation for not just the quality of people at Tcb um, but probably most importantly, the way the firm has thought about company building and I really admired that you know approach and the fact that you know it wasn’t just. Um, ah a focus on you know capital deployment as much as how you build great enduring companies and build you know seminal technology leaders and so yeah, it was very exciting to to you know, kind of join up with a firm that I had a lot of respect for I knew pretty well. Ah, and and so it was ah you know bittersweet to to leave m 13 but decided to join Tcb about two years ago and help them launch an early stage fund ah which we call our velocity fund.

Alejandro Cremades: How how big is the fund.

Gautam Gupta: Yeah, so we raised for the velocity fund which we closed in December Twenty Twenty one we raised four hundred and sixty million dollars ah and the strategy has been focused on series a b and c stage companies. Um, we can lead or follow. Ah, and we invest in consumer b two b two c and enterprise um, and you know we’re we’re about a year and a half in post closing the fund. Um, but we’ve got 8 portfolio companies today. Ah so you know off to a good start. Plenty of of. Ah, you know we’re open for business. So we we are very much actively looking for for ah new investments but off to a good start.

Alejandro Cremades: And obviously you know Ttv has been around I mean we’re talking about a firm with I mean according to crunchbys which is not accurate. But at least you know it’s something 396 investments ah hundred and ninety seven exits 12 different funds. So what is the approach and how for example. Ah, you go about? Perhaps you know like the different the different team players the different funds that you have how does that work and how that ecosystem that you guys have built at tcd how they can support founders. But.

Gautam Gupta: Um, the end.

Gautam Gupta: Absolutely so Tcb has 2 strategies. We have our early stage strategy called the velocity fund and then we have our crossover strategy which is what Tcb pioneered um, which we internally call our growth fund. Ah, the growth fund is in its eleventh fund. So the most recent vehicle was tcd 11 and then velocity is obviously on velocity one which is the first fund in the velocity strategy. Um, so that’s how you get to kind of the 12 total. Um, but. You know what I would say a couple things 1 is given the breath of tcv we can invest from series a all the way through public markets. So there’s very few with very few exceptions. We can be a capital partner to many companies. Ah, whether you’re raising your series a you’re raising a pre ipo round you know or or maybe something even a bit later. So so we have a huge amount of breath across the Tcb platform. Um, it’s a relatively small team and so the velocity fund is 6 people. Um, just to give you perspective the total firm. Ah, all employees um is about 130? Um, and so you know we coordinate and collaborate ah all the time and so you know on the investment side.

Gautam Gupta: Ah, we’re in the same meetings across the 2 funds ah and leveraging the insights and the network of the overall platform and and for companies I think the reason why that’s important is not only do you have a capital partner that can go the distance with you but you have the reach of. Everyone in the firm their personal networks their experiences all of the you know past portfolio companies that we’ve been involved in and so yeah, that’s a ah little bit of of you know how to kind of think about the the breath of the firm.

Alejandro Cremades: And you know it’s interesting when you talk about Networks because you know in your investment thesis I so you were as you were saying is series a series B but mostly you know like around those say cycles when we’re talking about series A we’re talking about. That day validation. There’s revenue not significant, but you know there’s revenue. Ah and now it’s all about figuring out how you go from early stage and transition into grow stage which is you know a really tough cycle to ah to shift from So. How do you guys go about. Really adding that level of value or plugging in your network so that you’re able to help the founder in crossing that incredible. You know, ah a lifecycle.

Gautam Gupta: So one. Ah, we we have a few different ways that we think about just helping companies scale and and obviously there’s a lot that’s situational right? So it depends on the company the market that they’re in.

Gautam Gupta: Scale of the company today and their aspirations. But I would say a few of the things that that we’ve done and and you know we are I think pretty helpful around. So the first is around talent just given the network of companies that Tcb has worked with in the past and. The number of executives that are in our network. Um, we think we can be really helpful at bringing the right people into a company to help a founder scale the business and so whether you’re looking for. You know a head of people. We actually have a venture partner at Tcb who was the chief people officer of Netflix um, you know whether you’re looking for whoever it may be right? The the next head of engineering to help you scale your your engineering efforts or product efforts those are areas where we think we can be uniquely helpful. Um, the second is we’ve built this advisor and venture partner network I had just mentioned one one of them. But we’ve built this advisor and venture partner network of industry leaders and executives who can be both informal and formal advisors and board members for companies. And so as you think about you know that series a or b stage company. How do you get the smartest people in a room around you who have taken companies public or who have scaled a business from 0 to billions of dollars of revenue billions of dollars from market cap. Um, we think we can also get those people in the room with you. So not just.

Gautam Gupta: Full-time employees right? and and the executives that you want on your team but also executives around you to be a sounding board for you and and to help you think through issues and and paths to to scaling so I would say those are 2 of the primary ways that that we try to help companies. Um, and and you know obviously ah through the network of the firm whether it’s you know you’re looking for m and a opportunity you’re yeah looking to buy a company. Um, you’re looking for help scaling internationally like. All of those are also areas where we’ve had experience and where we can help but it’s obviously very situational right? Like if you’re in the us and you’re looking to scale to Europe you know it’s an area where we can help. But how we get involved. There may be very different from a company that’s in. Asia looking to scale across the rest of Asia.

Alejandro Cremades: So imagine I was to give you the opportunity of going back in time and I put you into a time machine I put you into a time machine where it brings you back to the babson days. You’re a student at Babson. You really love the whole venture world.

Gautam Gupta: Boof.

Alejandro Cremades: And you give you have yourself there the opportunity of giving that younger gotam 1 piece of advice before launching a business so question will be why would that be n why and then also you have the chance to give that younger gotam 1 piece of advice before investing in your first company. Ah, would those be those 2 pieces of advice for.

Gautam Gupta: Interestingly, they would probably be very similar which is that it’s all about the people and talent. So from an operating perspective I think I would tell you know the the founder ah Chapter. Of of my life that it’s all about ah the quality of people around you and the talent density in the company and that to achieve a greater talent density in the in the business you’ll likely need to make hard choices or hard decisions. Ah. And almost every time you’re faced with a hard decision like that. The answer is actually so more simple than you think and and so you know if you have just to contextualize this if you have a great you know head of Sales. Or excuse me maybe not a great head of sales If You have a head of sales and and you’re struggling with hey ah should I Keep this person should I go find someone Better. You know, whatever chances are by the time it’s you know on your your mind right? that you might need to make a change that. It’s already. You know the the time to make that change I’m not saying that it’s too late often. It is too late or it’s it’s you know, ah beyond the point that you should have made a change but by the time you’re thinking about it. It’s almost always in my experience the case that um.

Gautam Gupta: You know you you have to make a change but you’re delaying the inevitable and and you know procrastinating that similarly with investing it comes down to investing in great founders I mean obviously ah, there’s a lot that we want to understand as investors about the business. The market. Unit economics all of those things at the end of the day especially in early stage investing those data points are slices in time and you may talk to a business where maybe some of those data points don’t look good today but they might look better tomorrow. What doesn’t change or maybe set a different way. What will canalizeze the change of the business getting better and healthier over time are the founders right? and and the team and so if you don’t have the right team in place. Even if the metrics are great today. They might not be tomorrow. Conversely if the metrics aren’t good today. They might be getting better because of the quality of the team. Um, and so it all comes down to the quality of the people and and really just keeping a very high bar on that.

Alejandro Cremades: I agree a hundred percent now for the people that are listening that will love to reach out and say hi. What is the best way for them to do so.

Gautam Gupta: Twitter Linkedin on Twitter it’s g ramblings and then you know on on Linkedin.

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

Gautam Gupta: Thank you for having me really appreciate it.

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