Today’s guest is Gautam Gupta, Founder and former CEO of Naturebox, and current Partner at M13, a venture capital firm based in Santa Monica. You’ll want to be sure to stick around, because Gautam shares a story about how he landed his first internship – and it has nothing to do with resumes or cover letters, he shares the story behind a company taking a chance on him to start a branch, and he shares the struggles of starting a business if you’re thinking about making a leap and taking the risk!
Ash Faraj 00:03
Hey, it's ash. Now today's guest is Gautam Gupta, founder and former CEO of naturebox and Kurt partner in 13. ventures a venture capital firm based in Santa Monica, you want to be sure to stick around today because Gautam shares a story about how he landed his first internship, it has nothing to do with resumes or cover letter, he shares a story behind a company taking a chance on him to start a bridge. And he shares the struggles of starting a business if you're thinking about making a leap and taking the risk. From the time that he could remember, Gautam always wanted to be an entrepreneur, his grandparents and his parents were entrepreneurs and dinner table conversations would always be about entrepreneurship. So it seemed like it was just part of his DNA. As an elementary school kid, he would sell all sorts of stuff to his classmates.
Gautam Gupta 00:55
I was born to immigrant parents, my parents immigrated here from India, and both grandfathers, my grandfather, on my father's side and mother's side had been entrepreneurs in India, the dinner table conversation was always around business and entrepreneurship, from a very young age, I sort of was exposed to the concepts of business. And I became enamored with this idea of building companies and you know, kind of selling things. And obviously, I was very young. So I just, you know, didn't know much about the word or the concept entrepreneurship. But, you know, I would read like Fortune Magazine, and, you know, pretend to do some stock trading and things like that. And so when I was a kid, you know, the first stroke of entrepreneurial ism came when I just basically started selling products out of my backpack to other kids in school. What were you selling? So the first thing that I sold was, apparently, you know, I don't know why, but I was enamored with these colored pencils, like these decorative pencils that were being sold at school through a vending machine. And so I found out that you could buy these things in bulk at Costco. So I asked my dad to go buy a package package of these from Costco and basically started selling them, I would stand next to the vending machine at school, and just sell them for a cheaper price, you know, out of my backpack. And so that was the first thing. You know, I think that was seven or eight years old or something
Ash Faraj 02:34
the school the school didn't expel you.
Gautam Gupta 02:36
Yeah, you know, there were some some times where I got into trouble at school for sure for selling stuff. Like I remember I had a business selling CDs when when Napster was big, I would sell like mp3, us, you know, put a bunch of mp3 is on a CD. And, you know, there were definitely times where the school shut me down on some of these things. But you know, I mean, it was kind of all for fun, you know?
Ash Faraj 03:02
So after high school, Gautam attended Babson College because they were known for their entrepreneurship program. And during his time there, he was very involved with extracurricular activities that related to entrepreneurship. Through his extracurricular activities. He met a partner at a venture capital private equity firm that invited him to be an intern, his first internship experience what happened because he meant someone made a good impression, not because he beefed up his resume.
Gautam Gupta 03:29
So I went to school at Babson College, you know, really, because Babson was known for entrepreneurship. And so I wanted to eventually start a company. So I thought, let me go to Babson feels like the best place to prepare myself for sort of that career. And then, you know, once I got on campus, I started to get involved in the entrepreneurship activities on campus. And part of those you with would be entrepreneurship club and things like that part of what we were trying to do is get people from the Greater Boston community business community, to come to campus and meet student entrepreneurs and hear ideas from student entrepreneurs and give us feedback and that sort of thing. I'd met some of the partners at General catalyst, because they were a Boston based venture capital firm, we were inviting some of their partners to come and listen to pitches and give feedback and things like that. And so on my way, you know, at the end of one of these events, beginning of my sophomore year at Babson I was walking one of the partners out to the parking lot. And he said, Well, what are you going to do this summer? And I the only response I could think of was, I guess I'll find an internship or like, I'll look for an internship, what else? You know, could I do? And he said, Well, you know, let us see if there's something we can do to help. And that was October of my sophomore year. I ended up starting in insurance. Tip with them that next month, and so I started interning for them. November of my sophomore year of college spent the next two and a half years, interning for the firm. And then I joined them full time after I graduated. And yeah, it was great. I ended up spending eight years of my career working for general catalyst.
Ash Faraj 05:21
So have you met him before you walked him out of the parking lot? Have you met him and met him before that day?
Gautam Gupta 05:25
No. So I've met some of the other folks at General catalyst, but not this specific partner. So, you know, because the whole thing we were trying to invite VCs and things like that to listen to pitches. And so it was really and you know, how it is when you're student, you're just anyone that has the time and, you know, generosity to come and listen to pitches. And so we were, you know, just thrilled that that someone from general callus would come and listen to these these, you know, pitches and provide feedback and stuff. So didn't really think anything would come of it, other than we were just excited that, you know, somebody, a prominent VC was actually going to come to campus and kind of give their feedback.
Ash Faraj 06:12
So after college, you went to work for p&g for a little bit. Is that right before going back to general callus.
Gautam Gupta 06:18
So I spent a full summer at General catalyst. And then my junior is sort of, in between my junior year and senior year, I spent a summer at Procter and Gamble, because I really, even though I wanted to be founder, and eventually and work in startups, I felt like I wanted to also just see what a big company was like, and sort of have that experience before graduating. And so and Procter and Gamble does an incredible job with their internship programs. So I was lucky enough to spend a summer in Cincinnati, working for Procter and Gamble. And I basically came into senior year with sort of the thinking that, you know, I could go back to Procter and Gamble and start, start my career working for a big company and, or I could, you know, stay at General catalyst, learn from the entrepreneurs that were coming through the door every day, and then go start a company. And so I ended up deciding to stay at General catalyst and kind of go that route.
Ash Faraj 07:24
What was that experience? Like? Like your first experience with a big company? Like, how do you remember it?
Gautam Gupta 07:30
I mean, I, the way that I remember it is I felt like I learned a lot. And there's big companies are big and successful for a reason, right? Like, Procter and Gamble has been around for I think, something like 120 years or something crazy like that. That's not an accident, right? These large companies do things really, really well. They're very smart people that work in these companies, obviously, there's bureaucracy, and red tape and things like that. But, I mean, these companies have survived for an incredible long period of time, not just, you know, stumbling over themselves. And so I think I gained a much deeper appreciation for how hard it is to operate a big company and for just how sophisticated large businesses are in running their, their, you know, p&l and running their companies. I think I also figured out that, you know, just to have the level of impact that I wanted to have, you know, it just the one downside with a big company is it can take time, until you get to a place where you're making decisions that really impact a business in a meaningful way. And, you know, for me, I you know, coming from more startups, or, you know, being around startups, I was excited by the potential to have that type of impact much sooner in my career.
Ash Faraj 08:56
I think you probably know the stat but like, in the past 70 years or so, only 10% of Fortune 500 companies still exist. So you're right. Yeah. Wow, the last that long, it's unreal. Yeah. Now, after college, Gautam committed to a full time job at General catalyst, because partners at the firm had been entrepreneurs. And his thought was that if he could be around successful entrepreneurs, the learning and the growth he would experience there would be very impactful. Eventually, the partners recognized Gautam's drive and hunger to build. So they asked him to start a West Coast office in San Francisco.
Gautam Gupta 09:27
idea in my head was let me go learn from people who had started companies, and all of the partners in general catalyst had been entrepreneurs. So I thought, let me go learn from people that have done it before. And then by virtue of being in a position to meet 1000s of entrepreneurs every year, I felt like I could learn from the entrepreneurs that I was investing capital into, right and I could figure out okay, this is what this company does really well. And here's how they Do it. And let me you know, take the the sort of good things from each company and try to synthesize, you know, what it takes to be a good founder and run a strong company. And so that was the thinking the thinking was actually not learn how to be a good investor, it was actually learn how to build a company from people that had done it, and people that were doing it,
Ash Faraj 10:25
I know that at some point, I think it was either 2009 or 2010, from what I read that had kind of given you the opportunity to just go start your own like branch or start your own office and the West Coast, he moved to the west coast
Gautam Gupta 10:38
to end of 2009, I become very interested and excited about the potential to invest in India, and the startup community that was building in India. Now, mind you, I grew up in the US, right. So I never lived in India, although spent a lot of time visiting and things like that. But I became very interested in the idea of, could I help, you know, find investments in India. And interestingly, General catalysts, like bless the partners, lgc, for giving me this opportunity, but they were actually going to let me move to India, and continue to do my job, looking at both us and India investments. And then what happened was, like, two weeks before I was going to move to India, two or three weeks ago, it was like very short notice. The partners came back and they said, hey, we've made the decision to start a West Coast office. And would you consider going there instead of going to India, and really helping us get the ground, you know, get off the ground in California. And I thought about it. And I was just super excited by that opportunity. Because I think in some ways, when you're in the startup world, you view Silicon Valley as the big leagues kind of I mean, I'm sure it's I don't know if it's even fair to, you know, make the analogy, but I think there's, there's something about Silicon Valley, when you're in the startup world that is very alluring. And, you know, it feels like the like, biggest stage for technology and startups and venture capital. And so I was, you know, thrilled to have the opportunity actually to go to California. Obviously, that meant the India plan wasn't gonna work out. But But I was very excited, you know, to sort of have the option to help build the firm's presence in California.
Ash Faraj 12:48
I know, sometimes when people ask you, when people ask like, questions that like, seem you're trying not to self promote, but at the same time, you want to say, why would I want to ask is, why do you think they they gave you that opportunity? What was it about your activity, or your time there? Or the impression that you made? Or, like, why do they believe in you? I guess what I'm asking.
Gautam Gupta 13:06
I do think one part of it was just right time, right place where I had been thinking about going to India, and so they knew that I was willing to move, and I was kind of flexible from that standpoint, I think the other piece of it is, I, you know, I had the hunger drive to sort of want to build something. And so I think the partners could probably tell that, that, you know, I wanted the opportunity to try to build and have that level of impact. And then probably the third is, you know, I think throughout sort of my career, I've been good or, you know, decent at managing, you know, a bunch of different relationships and conversations at the same time. And I think part of what was needed on the West Coast was to really talk to as many VCs, angel investors companies as possible to get the brand out there. And so, you know, it was one of these things were in order to build the brand and, and sort of compete in what was, you know, 10 years ago, pretty competitive environment. And today even more, you just had to, you know, sort of do the number of reps, right, you had to, you know, sort of do the work to put the brand out there. And I think folks felt that that I could I could do that confidently.
Ash Faraj 14:34
I assume you had a lot of rejection, what were maybe some techniques or methods or things that increased your your ability to kind of get your foot in the door, if that makes sense.
Gautam Gupta 14:44
Yeah, yeah. Pleasant. Persistence is the thing that comes right to my mind. So there was one company that I sourced at General catalyst called Big commerce. That's probably a good story here, which your company was based in Austin. Australia doing helping ecommerce merchants put put up a storefront online. And for a year and a half, I was reaching out to that company, they were responsive, and we would do phone calls and things like that. And you know, these were different. This is 10 years ago, this was zoom wasn't a thing at that point. But we would do, you know, phone calls and stuff like that. And finally, after a year and a half of staying in touch with them and trying to convince them to take capital, the founders decided that they wanted to raise some capital, and we were, you know, right at the end, kind of had the front row seat there, to be able to invest in that company. And so, you know, it's a good I think it's just a good example, pleasant, pleasant, trying to be pleasantly persistent. You know, and, and there's obviously a line between pleasant and not so pleasant. And, you know, but so, you know, being mindful of that, but but I do think persistence pays off. And time and time again, I've seen in my career, how much follow up and follow through matter. You know, basically, you know, following up on the things that you said, You're the action items, and things like that, and then following through, right, like doing the things that you promised you were gonna do. And and so I think that's been, I learned that in firsthand experience at GC, was that if you just stayed on top of these conversations, and if you weren't persistent, you know, sometimes Yeah, people wouldn't respond. And then there was definitely rejection. But if you were persistent, eventually, you know, someone might respond, and they might give you, you know, 10 minutes out of their day to chat.
Ash Faraj 16:53
Where do you draw the line between? Like, how do you find the cadence? Or where do you draw the line between persistence and annoyance? And I think, you know, whether it's somebody reaching out for a potential internship or a job or just like a reaching out for somebody as like, like an A mentor position, or mentorship position?
Gautam Gupta 17:13
Yeah, I think two thoughts on this one is, if you can come to the conversation, or to this task, with the mindset of give versus receive, so what can I give this person of value? I think that helps immensely. Right? And so, you know, rather than emailing someone, today, you set up an interview for an internship, is there something that you could send to them a white paper in Article, you know, some information, maybe that that, you know, you've heard through other conversations, you know, that would be relevant to their day to day job. So that you're, you know, you're not just asking for time, or an interview, or whatever it may be, but you're, you're really trying to start that sort of relationship or that communication off with the process of, of give, you know, give, and then get to I think that's the first thought is just to come with that mindset. And then I think the second thought is, eventually, you know, it's, it's, you want to find a message that resonates. Which means that, look, I think just trying the same message over and over again, is probably unlikely to succeed, right? That's where I think people get annoyed, and where you have the risk of running into annoying annoyance versus, you know, pleasant. But I think the main point is just to test different messaging, right? You know, if you're constantly sending the same email, the same thing, week after week, you know, maybe that's not the way to do it. Maybe it's, you know, change up what you're messaging about yourself and why you're relevant and why you have the conversation makes sense. And, you know, hopefully you find something that co nnects.
Ash Faraj 19:13
I love that's great advice. So research is very important mean, like reading news, articles, even books. information like that's how you gather for research is key.
Gautam Gupta 19:24
Ash Faraj 19:25
So at a certain point in his career, Gautam decided to make the jump, fulfill his lifelong destiny of starting and building a company and he did it with a friend from college. And a company started naturebox uses consumer data to make healthy snacks available to people in a very short amount of time. This was something he was deeply passionate about because he had a weight problem growing up. So you decided at a point that goes 2012, you decided that it was the right time to jump and start your own company? First question I have is how did you know it was the right time?
Gautam Gupta 19:59
Yeah, so I can To handle the confluence of three things happening in my life at that point. So one is I felt like it was the right time in my career where I had been at General catalyst for some time, I had helped source, a handful of companies, those companies were still pretty early stage. So it was going to take time for those companies to grow into the next stage. And so, you know, it was just the right time in my career where I felt like I could claim, like I, you know, the path at General catalyst had been successful, I've learned a lot I had contributed to the firm. And now, you know, it's kind of at the next sort of, I was at a decision point of whether I was going to stay in venture capital or do something else, it was just a natural inflection point. The second is, I had a co founder, a friend of mine from college that wanted to start a business together. And so the timing for he and I to do to start a company together was the right time, he or he was also at an inflection point in his business. And then the third is, we had an idea for a company that meant a lot to us. I didn't mention earlier, but you know, one of the challenges that I hadn't childhood was I was very overweight. I had very bad eating habits. But luckily, right before going off to college, I learned about nutrition. And I lost 70 pounds in six months. And I've kept the weight off ever since. And so this idea around healthy food, was something that was deeply personal to me was deeply personal to my co founder. And so we, it was those three things, right, I felt like it was the right time in my career, I had a co founder that wanted to be in business with and we had an idea that we were both passionate about,
Ash Faraj 21:55
do you remember it being kind of difficult, because it was like a general catalyst? We were, you know, relatively successful, right? Like you had you had been on a trajectory of like, if I stay here, I assumed you had like a partner Trek. It was like, a very, you know, clear path of like, you know, I guess, you know, being successful was ever like, oh, man, I'm taking a huge risk here, like,
Gautam Gupta 22:15
Oh, yeah, totally. Um, when I had that panic, or that that fear of Am I doing the right thing? I remember, when I made the decision to leave general catalyst and start naturebox. I called my mom and she was, you know, her response was, are you sure you want to leave? Right? Are you sure you want to leave? Gen galettes? I mean, definitely a lot of fear. And, and a lot of anxiety around whether that was the right choice. And, and and by the way, that that continued even after the decision to leave, right, like, and I think this is true for many entrepreneurs is that you have these near death experiences that force you to sort of re examine, hey, was this a good decision? Right. And, you know, I think the perseverance to just ride the those sort of valleys, peaks and valleys is one of the things that I feel like every entrepreneur learns how to do in their own way. Because it's, it's just a necessary part of the journey. It was deeply personal to me all and was a good business opportunity. Right. And so, it was, I think, we felt like we were making a responsible decision, where we're starting a company that not only was something we were passionate about, but also it was a good business opportunity.
Ash Faraj 23:44
When you started your company, I, it was personal to you should should, whether somebody is deciding, hey, I want to go, you know, should I stay in my job in the corporate world? You know, or look for a job in the corporate world? If they don't have one? Or should I go start a business? Should that be like a more of a logical decision? Or should it be like an emotional decision like this, I'm so fired up about it. This is what I'm gonna go do the decision to do something to mean not to do something, but to start your own company or you know, find a job or standard job
Gautam Gupta 24:13
starting a company is super hard. And there's going to be some really tough days where you're going to want to quit or maybe you're going to go into at least question that decision of should you started this company. And so I do you think that the emotional side of it matters a lot. If you're just starting a company because you think something's a great business opportunity? Look, I think that can work. But I just worry that, you know, you may not have the emotional, you know, sort of passion or commitment to the business to get through some of the really tough days. And so I do think that having that emotional sort of connection to what You're building matters a lot. Because you, it's hard. And to be fair, it's really hard to not have that emotional connection. Because I think we would all founders, what you're building becomes part of you, right, it becomes part of your identity. And so I do think that like, I don't know that I've met a founder that doesn't have some emotional connection to the company. But But I would say like, if you if you're making the decision, to leave a job and start a company, it really helps to be passionate about passionate and committed, you know, to the mission behind whatever company it is that you're starting,
Ash Faraj 25:39
you made the jump from being founder and CEO, to, you know, go back to being back to an investor, what made you decide to do that? I mean, why, why not just continue your path and naturebox continue to grow? Continue? Because you've been there only for? Like, what, seven years? Six years? Seven years? Yeah. And it wasn't, you know, for me, I guess for a company that's seven years is a long time, but in general, but for a company, it's not a very long time. So what what made you decide to leave,
Gautam Gupta 26:08
I was just tired. I've been CEO for six and a half years, the business had gone through a lot of ups and downs. We were lucky and fortunate that we got with the business got through many of those hard moments. But we definitely had our fair share of near death experiences. And I was at a point where, you know, we really had improved the profitability of the business. And I just wanted, I didn't want to be the CEO anymore. I just wanted to take a break. And so I transitioned to a new CEO at the end of 2018. And I took some time off and and, you know, in that time off, I realized, I think I had known this subconsciously. But I kind of consciously realized that I wanted to go back into investing. And I really wanted to try to use what I had learned as an operator to help entrepreneurs have avoided some of the mistakes that I've made.
Ash Faraj 27:17
If you were to meet the 25 year old Gautam, what advice would you give to him?
Gautam Gupta 27:21
And so two things take more risk, and be more thoughtful around people and people decisions?
Ash Faraj 27:32
What in your life do you feel like has given you the greatest sense of fulfillment,
Gautam Gupta 27:35
I get a lot of joy and fulfillment from what I do. And so I think, work, you know, hear about their teen, even at naturebox, like, I just get a lot of fulfillment from from, you know, building and, and sort of working with entrepreneurs and sort of seeing, you know, seeing the the sort of how you can create something from nothing, you know, and that is, that's what sort of fires me up.
Ash Faraj 28:04
What has been the happiest day in your life so far?
Gautam Gupta 28:07
probably getting married. So I got married, right, before I left naturebox. In 2018, probably that at this point,
Ash Faraj 28:17
if you could be remembered for just one thing, what would you want that to be?
Gautam Gupta 28:21
I think for me, that would be that I helped moving either fund or, you know, impact a company that really changed the way hundreds of millions of consumers live. And so, you know, I would love to just be involved in a company that has that level of impact on the world.
Ash Faraj 28:41
In your opinion, what is the most important life skill?
Gautam Gupta 28:45
Probably selling, I would say selling communication. I just think so much of especially in entrepreneurship, so much of the job is you're you're selling not only the opportunity to investors, but you know, teammates, and partners and customers and vendors and all that stuff. So probably selling
Ash Faraj 29:07
what is the best advice someone has ever given you?
Gautam Gupta 29:10
So I think it's funny. One of the books that I read, maybe a year ago or two years ago is shoe dog with Phil Knight, Phil Knight about, you know, sort of the Nike story and he talks about how, you know, never listen to advice or never give advice. But the sort of biggest thing that he says is like, you should just never give up. And I actually think that for most companies, and most people, often they just have to hear that. Right. And so I think probably the best the most impactful advice that I've heard at different times has been some variant of don't give up right? Because usually when you're thinking about it, it's it means that like you're staring you know, down dark tunnel and you know, like are staring towards a dark abyss and so you got to you know sort of that that encouragement to not give up is a big deal.
Ash Faraj 30:09
Last one is if you were stranded on an island and you had access to one meal, hold them up for you.
Gautam Gupta 30:16
That's a great question. So I love I'm a big ice cream pan. Unfortunately growing up I was too big of an ice cream and way, but I think it would have to be you know, some type of, you know, tub of ice cream or something. I don't know,
Ash Faraj 30:31
Gautam Gupta 30:33
You know, I oscillate between mint chocolate chip and cookies and cream.
Ash Faraj 30:39
Is my two favorite flavors.
Gautam Gupta 30:40
Oh, yeah. Yeah, you know, I like cookies and cream.
Ash Faraj 30:45
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