From banker to entrepreneur: why would someone do it? [OES S01E04]

Most people would consider working at JP Morgan a dream job. But that was not enough for Vikram, who decided to quit his banking job after working there for 7-8 years to start his own business. He is currently the founder of Draper Startup House, a successful entrepreneur hostel chain that has hostels from Vietnam to Houston. At age 40, he is a rarity among young entrepreneurs. There were many ups and downs in his entrepreneurship journey, yet he did not give up. What kept him going? He shares his thoughts and more in this episode of Our Entrepreneurshit Show by The Financial Coconut.

One of Vikram’s most memorable entrepreneurshit memories was being arrested in Waikiki Beach for selling football jerseys on the street without a permit when he was just 17. Fortunately, that sounded worse than it really was. Vikram then reflects on the difficult moments that led up to him quitting his job and the pressures he had to face. To him, breaking away from his banker identity was one of the most difficult things he had to do.

While Vikram sees entrepreneurship as having the ability to create your own job and pay, he also recognises that it comes with challenges. One of the greatest challenges he had to overcome was finding talented business partners who can get along. Listen to this episode to find out how he learnt it the hard way and which book eventually helped him overcome his self-doubt and become a successful entrepreneur.

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podcast Transcript

Vikram: All right, my craziest entrepreneurship story is, I was arrested in Waikiki beach in Hawaii when I was 17 for selling football jerseys without having a permit to sell on the street.

Expand Full Transcript

Reggie: Have you ever wondered if you could travel the world and run a madly successful business at the same time? Living the dream, they say, our guest for today has quit his high paying banking job and travelled half the world. Okay, I know a little bit cheesy these days. What is interesting is he went to multiple failed ventures in Bangkok, breaking down and having a very hard time in a foreign land. He later tried to recreate this experience of backpacking and venture building into a pretty successful entrepreneur hostel chain.

So, let’s welcome Vikram, founder of Draper Startup House, that has a big entrepreneur lodging network from Houston to Estonia to Vietnam and what have you, to share his little cheeky experience of how he uprooted himself from corporate America to become a dirty startup founder in his forties, in Singapore. So welcome to an entrepreneur shit show. 

Vikram: Well, apparently, it’s very common thing. 

Reggie: Really? Okay, so share with us more alright? 

Vikram: Well, there is a sporting event called the pro ball and it’s a very big sporting event and people spend a lot of money on merchandise, buying t-shirts and all the full gear. And I was on the beach and I thought it was a good idea too. So, I partnered up with someone to sell merchandise and didn’t realize that we needed a permit to be able to like sell stuff on the street. And I didn’t have a permit and I got arrested for not having a permit, which I know it sounds worse than it is. It’s just, it’s not a criminal offense. I was put into a holding cell and sort of experience a little bit of what it could be like being a juvenile offense, I suppose. And yeah, so that’s as crazy as it gets so it’s nothing crazy. 

Reggie: But it’s pretty wild right? Like, that kind of started you off on this like whole entrepreneurship thing, and then you moved on to do other stuff, right? And then you joined corporate America. 

Vikram: I did. 

Reggie: So yeah, just kind of help us understand, like, how was that journey, from like, this crazy guy at the Waikiki to corporate America?

Vikram: Yeah well, truth be told, I feel my entrepreneurship journey is just starting. That’s how I feel and the reason for that is I started building companies much later in life. Generally, when you talk to entrepreneurs, you hear the success stories, generally it’s like someone started a company at 18, became a billionaire, or someone started a company at 23. So, there’s like a lot of these amazing stories of successes of people striking out on their own and building something, but I feel that moment hasn’t quite come for me yet. I feel that moment is still to come. 

Reggie:  How old are you? Just kind of give us an understanding, like, when you say late. 

Vikram: Yeah well, I’m 40. 

Reggie: Oh okay. You don’t look 40.

Vikram: No, you look young, but you know, Draper Startup House or at the time Tribe Theory, it was something I started when I was 3… 8 or 37, which is pretty late to be starting a company. At least that’s what appears, but if you look at the statistics and the data, you’ll see that most companies in the world have been started usually by people around, 40-ish, 40 plus.

Reggie: Yeah. 

Vikram: And I think that makes a lot of sense for me now that I understand what kind of person I am and what kind of things I like to do and not do and the experiences I’ve had. It makes perfect sense that this is actually a really good time to start a business. 

Reggie: Yeah, and I think we were looking at the same research, probably right. So that research talked about how the success rate of people that are older tends to be a lot higher, but the number of successful startups that come from the, quote unquote, the more experienced people for lack of a better way to put it, it’s lesser, right. Because there’s just lesser people trying, right. And why do you think that’s the case?

Vikram: Well, I think generally I feel in this stage in my life, even though, I have a family and taking a risk is probably not as appealing as if you were a single 25-year-old person, who only had themselves to worry about. Even if that is the case, I personally feel that I am more well-prepared to pursue something that I have done some analysis on, pursue something that I know is something that I want to pursue as in something that I’m passionate about. 

Reggie: Yeah, but why aren’t your peers doing that? Because what we’re saying is that there’s the lower tendency of people trying entrepreneurship at an older age. Yeah, so you’re probably an oddball amongst your friends.

Vikram: Yeah, I suppose so. And I totally understand why following or trying to do an entrepreneurial venture at this age would be very unappealing because it’s very risky, especially if you are someone who has a career that is good at say banking or good at being a chef or just good at a skill.

Reggie: Yeah. And you were good. 

Vikram: And I was, yeah. That’s right, so I spent 7 or 8 years in banking and I felt I acquired skills that people could pay me money for. Like, if I went and worked at a bank, I suppose I could probably, I hope, get a job where someone says, hey, Vikram has skills in banking or in client services or in sales or in reporting or whatever it is that we would like to pay him money for his time. I’m sure that is true, and I think people become comfortable with that and I think that’s totally fine. So, it’s just the later stage in your life, the more risks there are because you have to give up more, you have to give up, you have family, you have a set career, you don’t want to start from zero again, there’s social pressure, there’s family pressure. I mean, it’s more complicated at that stage of someone’s life to start a new company. Unless you already have wealth that you don’t want, that you’re not worried about wealth, and so starting things is a natural part of your life, but for most professionals who are in a career where they exchange time for money, starting an entrepreneurial venture is very complicated and risky and difficult. 

Reggie: So, you were saying, like, there are so many different kinds of pressure, family, social, financial pressure. What was the biggest one for you? 

Vikram: Well for me, I think the pressure was lower because even though I had a profession, doing something what I’m doing now was something that I’ve always wanted to do. And I got lucky, having a spouse who was very supportive, I think that’s a huge help. So, my wife, Anna, she’s been very supportive from the very beginning and if that was not the case, I guess it could have been a different scenario for me. But she was very supportive, and so I think that’s one piece. But I think the greater piece probably is that my assessment or risk is probably different than most people. The reason for that is I grew up with not a lot of stuff. I didn’t grow up with a lot of things and I didn’t grow up with having an ambition to have a status. So, it doesn’t take much to make me happy, like, I don’t need much to be materially happy. I’m not one of those people that wants nice cars, wants nice houses, wants nice things. I just don’t have the desires to accumulate a lot of nice things, and of course we all like nice things, but I don’t have this inherent desire to sort of have X amount of accumulation of wealth to be happy. I don’t need much. 

Reggie: Yeah, but you still left the banking sector in that sense, right? So, although you don’t need a lot, but that was paying the bills and after seven to eight years, you left banking. 

Vikram: Yes. 

Reggie: And you transit to being entrepreneur, right? So, if there isn’t a lot of pressure in terms of social pressure and in terms of material, financial pressure.

Vikram: Yeah. 

Reggie: Then what drove you out of a comfortable job? 

Vikram: Yeah. So, this actually it’s a really good point because I used to work at JP Morgan, which is 

Reggie: namedrop 

Vikram: It’s a well-known bank and it’s a brand that a lot of young people want to go work at. And when I was doing my business school, so I did my MBA while I was going to, while I was working. And you know, a lot of my peers in business school wanted the job that I had. So, I mean, it was clear that it was something that people wanted to be in. And you’re right, when you’re in a situation where when you go to a cocktail party and your identity becomes where you work, then shedding that is very difficult. And as you can see, like, you go to any sort of professional setting where you work and what you do for a living is your identity right? It becomes I am Reggie, I’m a banker. I work at this bank. That becomes your de facto identity. 

Reggie: Yeah. Even in startup networking events, it, there is a certain pressure.

Vikram: Right.

Reggie: When I go there, like, maybe I’m not here yet, like, because some of the startups, the bigger brands they’re doing better right. And then if you’re representing the brand right. So, I kind of get what you’re saying. Yeah. 

Vikram: Which is, it’s a very interesting phenomenon because if you think about companies, like what companies provide, in exchange for your time, is they provide you with a platform that gives you identity right. I work at this insurance company that gives you an identity and companies essentially are providing you with an identity and are providing you with a platform for you to build your credibility right. You don’t have to do it alone because if you’re trying to do it alone, it’s a lot more difficult, but joining a company that has that network has the brand, then that’s what they’re providing you more than just money right. And so, identity is such a powerful thing and letting go of an identity that other people covet is a very difficult thing to do. And that’s probably one of the reasons why people who work at great companies, they have a very hard time starting out on their own because they have a lot of things that tick the boxes of, I have a great identity, I have a great paycheck, I have a great career, I have a great future

Reggie:  Corner office.

Vikram: Yeah, but also, I mean, these are all things that are, I think, important in the sense that it gives you friendships, it gives you global networks and these are all very important, valuable things. I suppose, exchanging that for something, to follow something, and starting from zero that doesn’t have a clear probability of success, it’s a very difficult exchange to do. So, I totally understand why people don’t want to do it. I recognized that when I was thinking of, like, starting something on my own, I knew that I had to shed myself from that identity. And so, what I did was I literally put a very hard stop to that identity in the sense that I quit my job, I sold everything I had, I picked up a backpack and I went backpacking and I went to South America and I was hitchhiking, I was backpacking and staying in backpacker hostels. I did a complete 1 80-degree sort of change because I knew that identity that I had, the first thing I had to do was shed that identity. And once I shed that identity, became a dirty backpacker, it was kind of like I was, it was 

Reggie: Okay. We’ll do anything, right?

Vikram: Right, and that’s sort of, I think, well, part of it was intentional, part of it was unintentional, but looking back, I think that shedding of identity was such a critical part of me being able to embrace new things and take new risks and pursue new things. That was a very, very important piece of the journey, 

Reggie: From corporate America to where you are. So that’s the transition right. And during the traveling, going to all these different places, do you feel like you have redefined success or redefined your life in that process?  How did that feel?

Vikram: Yeah, definitely. It may sound cheesy, but I actually really feel that I’m very successful. And for the following reasons, I have relatively, I mean, I have good health as far as I know right. I feel healthy, I have a loving wife and a family, I have, just generally have loving friends and family all around me, brothers, sisters, friends I grew up with and I feel I have a relatively young mind in the sense that I don’t take myself too seriously and I feel,

Reggie: And that’s a good thing? Not taking yourself too seriously? 

Vikram: I think is a great thing. 

Reggie: Why?

Vikram: Well, my experience has shown me that if you take yourself too seriously, then you mess up more and it becomes more difficult to do new things because you become a bit more rigid. If you become so rigid, there’s no, it just feels more fun to not be rigid. And I suppose like not taking yourself seriously doesn’t mean being complete derelict but, I guess, if you’re not having fun along the way, what’s the point. And so, I think because of all of those reasons, I feel very lucky that I went to good schools, I feel just as educated as the next person in my stratosphere. So, I don’t feel I’m missing out on things from a learning perspective, so I think all of these things make me feel successful. I’ve travelled the world, which is a privilege, which I’ve had the privilege to do. I’m generally a very optimistic person and I’m generally a very positive person. I think these are good things and I think there’s a combination of all those things makes me feel I’m very successful. So that’s maybe from a social, emotional perspective, and then from a financial perspective, I’m definitely not wealthy, but I know that if I wanted to make money, if I wanted to exchange my time for money, I could do it. I think I’m still employable, so if I needed to go make money for the family to put rice and curry on the table 

Reggie: That’s all we have every lunch. 

Vikram: Yeah, I suppose I could do that. So, I think that gives me a sense of peace that I am still employable if it came down to it. And so, I think the combination of all those things makes me feel successful. And I just don’t have the ambitions to be a tycoon in any business cycle. I don’t have that ambition and because I don’t have that ambition, I don’t feel like, the bar for me is not, I’m not trying to become the Elon Musk. I’m not, I just, I want to pursue and try to create things that I want to, and if that happens great, if not, that’s also okay.

Reggie: Okay, so when you say you don’t have the ambition to become a tycoon, but you travelled half the world to this other part of the world and you first started your first venture in Bangkok. 

Vikram: Yes, 

Reggie: Right? Why do you decide to start a business then? No ambition. 

Vikram: Yeah. Well, I’ve always wanted to start businesses.  That’s for sure, even when I was in university in Waikiki. I think more than starting a business, I think controlling my own destiny and having freedom was something I think all of us want. And I just felt that if I worked, if I exchange my time for money working for someone or at a company that is not the freedom that I wanted. I wanted to be able to say, I’m paying myself, that gives me freedom to then make decisions and do things that is different. 

Reggie: And is that true?

Vikram:  Yeah, for sure. Oh, for sure. Yeah, I mean, definitely.

Reggie: You don’t feel, like, you’re creating your own job and then you’re in your own business, you pay yourself, but then you’re still within the job, you know what I mean?

Vikram: Right, that’s true. So, it’s definitely not a perfect scenario, but it’s a scenario that I prefer, over someone telling me what to do or what not to do possibly.

Reggie: So how was that first venture in Bangkok like? 

Vikram: It was fun at first then became very difficult. At first, I was very naive, so I thought, oh yeah, we’ll do these things, but then as you start to learn about how complicated things can be, how difficult it is to do simple things like registering a company and having contracts signed and everything is just so much more difficult. Once I started learning that and experiencing that, it became not so fun. And so, I started off like super, super fun. 

Reggie: What were you guys doing there?

Vikram: So, the first thing we did was, we’re building a startup incubator, which had just tons of ideas that we were incubating. So, things like accounting systems, there was one startup that was trying to build like a Xero for the Thai market. There was one idea where we’re trying to build a plastic surgery marketplace. There was one idea that was trying to build you know logistics last mile delivery kind of stuff. So, all sorts of ideas, that was our first project, just incubating all of these ideas. The second one where I spent a bit of time on and actually raised venture money for was to do a food delivery business in Bangkok. And the spin on the food delivery business was that we were going to do it completely through social channels, so all the ordering and everything, we would not build an app, it would be done through messenger, Facebook messenger. And this is when Facebook messenger was really starting to do all the APIs and integrate with different businesses, and I think, they were experimenting with a lot of the stuff in Asia. It hadn’t been rolled out even in the US, and because a lot of commerce gets done in Asia through social channels, like Facebook messenger, Instagram, we thought this would be a good way to build a food delivery business completely on top of social media. So, we raised a bit of venture money for it and we built it, and it was out in the market for a while, but I ended up leaving that company.

Reggie: Why? 

Vikram: Well, two main reasons. The first main reason there is a lot of founder challenges, we had a group of people who came together to build this thing, and after a while personality clash.

Reggie:  How do you even start with this group of people?

Vikram: Well, that’s the thing, I think, this is a good lesson for the future for me, which is the groups of people you come together start a company, you have to make sure that those groups of people are a group of people that are gonna really get along. And this group of people, great people, but we just at some point didn’t gel that well, and this is because we didn’t really know each other that well. We came together through social networks, we were all involved in something or the other, we met as friends and became friends and then said, hey, let’s launch this thing. And I guess we’re all acquaintances we didn’t really know each other on a deep, deeper level. And so, when things got really rough, personalities clash, especially if you don’t know each other well, and that trust factor hasn’t been built over time, so that was probably the biggest issue. And the second issue was, doing food delivery was not really where I want it to be, it was not a passion that I thought was worth pursuing over these major personality clashes that were happening. 

Reggie:  So maybe, just rolling back on the personality clash, I’m just kinda curious, like, do you think people should get partners that are talented?  Or should it be like people that they can trust? So that’s the thing, how do you then decide how much is talent? How much is trust? And how do you factor trust? 

Vikram: I think it’s both, especially in the beginning stages of a company, you’d need partners who have talent and those talents have to offset your talents.  If it was just people that you trust and they have no talents, it’s going to be very difficult to build something. So, I know it’s and that’s why it’s so difficult. It’s so difficult to find founders. And if you see a lot of startups where companies fall apart because of founder issues, and I think it has a lot to do with trust, but probably trust plus capability and ability. Because a lot of times I’ve seen two friends come together, they trust each other, they love each other, friends since childhood that come together to build something, and it turns out that none of them have the ability to do all the things that need to be done, which in the beginning stages to kind of have to do everything 

Reggie: Everything.

Vikram: Right, so if there’s some major abilities or capabilities that are lacking, then it means you have to go and hire someone else, which means that’s you have to pay someone else to do it. And so, I think it’s definitely both, but if I had to pick one of the other, I would say probably trust is, and the ability to really work together, especially when things get really, really hard is probably more important because you can go hire someone for ability.

Reggie: Okay, but best is both. 

Vikram:  I think it’s both.

Reggie: So is not just about pulling that random friend that you that you enjoy hanging out with. And it’s not also just finding someone that’s talented but you can’t gel with. 

Vikram: Yeah, because if that ability and the capability is missing, then that personal factor starts to deteriorate, because then when things get really hard, you go, well, I’m doing all the work. What are you doing right? Those types of questions, they start weighing on you. And so that’s why I think, having both the boxes checked is important. 

Reggie: It starts hounding, right, during tough times. And then when you broke up with them, what happened for you?

Vikram: Oh, I mean, it was very difficult for me. It was a period, it took me about six months to really get myself back up, and get over the emotional pieces that sort of fell apart during that time. So, I spent six months kind of recovering, to be honest. Yeah, I was kind of a bit in the pits.

Reggie: How did that feel? 

Vikram: Well, you start to really question yourself, and there’s a lot of self-doubt that creeps in. Why did this happen? What did I do wrong? This is how it’s going to be. Why can’t I get along with people? So, there’s a lot of self-doubt that creeps in, and it there’s a lot of blame game that you blame someone else for the situation. Why didn’t this person do this? Why didn’t that person? And then you start to blame people.  And when you start to blame other people for situations that are completely your own doing, because ultimately everything is in a way. We’re responsible for everything that happens right? And so, I think there was a lot of blame game in my head. And by the way, this is all of the psychological, monkey mind, just yammering on and the thing is like, after that, I didn’t really have something that I jumped into, so I had time, to really and that’s probably not the best thing. If you come up from, it’s like a relationship, if you come out from a bad relationship, from a breakup, and you jump into something that keeps you occupied right? Like, let’s say you’re on and training for a marathon or you’re climbing a mountain right. You’re doing something that keeps you occupied, so you don’t think so much about that relationship, but if you had a bad relationship and then you have a year of nothing to do, or you’re sort of sitting around then, that becomes a very difficult sitting around because you have all the time in the world to think about all the things that went wrong and could have gone wrong or could have gone better. So that’s sort of what on and happened to me, I had time and because I had time, a lot of blame game self-sabotage, self-questioning, all the negative things, that can happen sort of occupied my mind for six months and it took me that long to sort of just recover from the situation.

Reggie: So how did you go from, like, the abyss to where you are now? Which is like, okay, I think I value, if there’s anything, you know, I could go out and work? So that’s from shit show to become, like, confident right? So how did that happen? 

Vikram: Yeah well, so there was a very critical moment where I was on a plane and I bought a book to read at the airport, at one of the book things, I bought a paperback, and I’d heard of this book before but, it was not in the forefront of my mind. And it was a book called the power of now, I suppose you could say it’s a philosophy book or maybe it’s a self-help book. And I read the book on the plane. It’s an easy read and that literally shifted my perspective and shifted my thinking, and it just snapped me out of my condition. And it was so simple, the whole premise of the book is, you’re letting your mind go back to the past and just live there. Whereas you should be living today, now, in the moment, you should be living as things unfold and not, because that’s all said and done and it’s not real anymore right. It’s just, it’s done. So, it was really that simple but maybe the intensity of the book and how well it’s been written and how well it’s communicated sort of connected with me, and I snapped up and that’s all it took. But that’s what I think now, but I think I had to go through that pain.

Reggie: Yeah. You have to analyze all those, internalize the thoughts and just kind of look at all these things to finally, that was like the last thing. 

Vikram: Well, that was the thing, if I hadn’t gone through the pain, I don’t think that book would have made sense to me.

Reggie: Yup.

Vikram:  And that made that book spoke to me because I’d felt all the negative things associated with what happened and the pain was strong. So, reading this book, I was ready to get the medicine in that sense. So yeah, so that was a pretty critical sort of switch in my mind, which helps me even today.

Reggie: Cool and one last question right. I just want to know, like, why despite all these, sounds like crazy right? Why do you see do it? 

Vikram: I genuinely love doing this most of the days, but really in terms of like ideas that I want to be pursuing right now, this is it. This is the one that I want to pursue. This is the one despite all the challenges, right? Despite COVID, despite all the shenanigans that are happening that are, like, literally like, winds in our face right. I still, this is the idea that I want to pursue and because this is the idea I want to pursue, I feel energetic about it and I feel this is not wasting my time that this is worth pursuing because it’s something I really want to pursue

Reggie: Working with people that you can trust, but are also talented right. And that is, from a personal experience, that is a real challenge right. Finding people that are really good, but also you can trust them right. So, from my experience is a lot about spending time together to test out some things, so we don’t commit, we don’t over commit to each other. We just kind of test each other out, do some small little projects, and from there then we decide that, okay actually, this person is quite good, pretty talented, and I feel comfortable talking to them and working with them. And the comfort goes beyond just work by a lot, but also to the person right. So, I think it’s kinda where I stand from this interview, I hope you learned something useful and hey, since you stay all the way here, Vikram has something additional for you after this. So just if someone wants to start entrepreneurship right, what is one advice you would share with them?

Vikram: The advice I give myself is, you have to be willing to be embarrassed. And this is something that I have to tell myself all the time. This is what I had to tell myself, when we first started this idea was you have to be willing to be embarrassed because not everyone’s going to get it. People are going to laugh it off, whatever ideas you have, someone’s going to, like, give you all the wrong signals right. So, you have to be willing to be embarrassed for an idea that you think is worth pursuing. 

Reggie: Okay, thank you. Thanks for today. Thanks for your time. See you soon. All right, bye.


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