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Amit Gupta

by Josh Pigford. Last updated on February 06, 2024

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This week I talk with Amit Gupta, Founder of Photojojo and a dozen other things! We talk about dropping out of college, working with Seth Godin, starting Photojojo, being diagnosed with leukemia, beating the 1:20,000 odds of finding a stem cell donor, how community has played a role in business in life and what Amit is up to now!

Josh Pigford: Hey Amit, how is it going?

Amit Gupta: Good how’s it going with you?

Josh Pigford: Going well, thanks for hopping on a call. The way I kind of like to kick these things off is really starting with you as kid, so I’d love to hear what your childhood was like. Growing up where you grew up that kind of thing.

Amit Gupta: Sure that’s such a broad question. I grew up in Connecticut. My parents immigrated to the country in their 20s and I was born about a year after. I think I had a pretty normal, pretty nice childhood. Very supportive family. I’m trying to think of anything notable I guess. Probably the most relevant thing is just that I was super into computers earlier on and I have no idea why but I feel like it ended up defining a large part of my childhood and then later adulthood.

Josh Pigford: Was there anybody in your family that was into computers or did you get a computer at a young age or anything like that?

Amit Gupta: My uncle, my dad’s brother was an engineer but not a computer engineer. He lived on containerships and worked as the engineer in these ships. Whenever anything broke he was the one who fixed it. He’d be gone for months at a time on sea and I just thought that was the coolest thing ever. When he visited he would tell us all these stories and he would basically come for a week or two and stay with us and fix everything in the house. I think that just made me so curious, like how is this even possible? How does this guy know how to do all these things? I think it may be very interested in taking things apart and trying to put them back together, which I find out I was not nearly as good at as he was but it you really got me into figuring out how things work.

Josh Pigford: Were either of your parents, did they have an entrepreneurial bone in their body or was it … You know a lot of times it’s kind of polar opposites on either you’re really super into business stuff or you’re very hardcore get a job, this is what you do kind of thing.

Amit Gupta: I think they’re pretty traditional Indian parents. This is a cliche but I’m supposed to be a doctor or an engineer or if you can’t do those things you can be a lawyer and that’s okay too. My dad is a doctor, my mum stayed at home until we were a little bit older and then helps my dad with his medical practice. When I was in my late teens, I remember going to a doctor summer camp and watching autopsies and stuff. This was very much not the direction I was supposed to go. Not that they were forcing it but it was just like of course I would do this. I was super interested in computers but it was like be doctor. I think it was not till college that I decided I didn’t want to do that. They were very supportive about that. Not super entrepreneurial. Although my dad’s medical practice is a small business. When he moved to this country which itself is kind of an entrepreneurial move.

Amit Gupta: Then he set up this practice which was, began a small business, had to figure out how to do payroll, figure out all these things and he did somehow even though he didn’t know anybody in this country. My mum’s extended family, like her brothers, her dad they were all [inaudible 00:04:19] so I guess there was entrepreneurial influence but I didn’t see it that way.

Josh Pigford: The medical stuff did it interest you at all or was it just sort of this is how we’re going to do this? You just did it going through the motions.

Amit Gupta: You know interestingly I watched Doogie Howser and that seemed really cool it’s like the actor totally … I’m not going to be a doctor at 14 or whatever but this person seems to be and I think it was cool what my dad did. I thought it was cool whenever we went out to eat or just out anywhere he’d ran into a patient and they’d all seem so happy to see him and so grateful for what he’d done for them. That seemed very exciting. There was a part of me that was definitely interested in that. I think it was until I got to college and started taking the advanced chemistry and I just do not like this. I don’t want to spend the next four years in college and then a few years years after that doing this stuff that I don’t like. I just decided on a change course.

Josh Pigford: Your into computers as a kid. I guess what age were you when you were first introduced to the internet.

Amit Gupta: I know we had gotten an Apple 2GS relatively early and that didn’t connect to the internet but I think I had lobbied my parents for years to get a mac and we got a quadra 610 with a really cool adjustable keyboard and everything in it. I think it had A 144 modem. I think my introduction to the internet was a AOL probably or prodigy or copy surf. I’ve used all of these but I don’t remember which ones came first. Just a lot of time spent in message boards and spending time blocking the phone line to my parents.

Josh Pigford: For you was the internet this platform for being able to create things or was it more for you this way to connect to other people? Almost like a community aspect.

Amit Gupta: It was definitely in the community aspect. I was into computer programming kind of early. I would go to Barnes and Noble and buy the magazines that are printed in the UK that had the CD full of software and the printed software and the pages that you could type into your computer and then basically do that stuff. I went to camp to learn about computers and programming and then later was a counselor teaching logo to the kids. I was into making stuff or at least trying to make stuff but earlier on at least the internet was nothing. It was just talking to people and meeting people in far-off places who are into weird stuff. I don’t even remember what we were talking about but that part was just fascinating. Just being able to talk to people far away who I’d never seen or met and never would.

Josh Pigford: What is this in college when you got into this or why you still then a high school kid?

Amit Gupta: High school.

Josh Pigford: High school yeah. To me that’s really interesting because same experience for me. I was a high school kid when stumbled upon AOL and all that stuff. Just the idea that you could interact with somebody any instantly got me hooked. You’ve been introduced to the internet, you’ve got a computer and then you decide to head off to college. Did you start college with the intent of pursuing medicine?

Amit Gupta: Yeah in high school my high school had one class. I don’t think it was in classes, it was at a club or something where you could learn pascal so I had done that. I had started this small business in high school helping teachers upgrade their computers and add memory to their computers and drives and things like that. I was into computers but I got to college I was in the premed program and that was the [inaudible 00:08:39].

Josh Pigford: You mention helping people upgrade their computers and things like that. Do you feel like you had any sort of entrepreneurial bent then or was there a different motivation behind it?

Amit Gupta: No totally I did. For fun I’d be reading the story of Richard Branson biography or the story of Sony, or the story of Starbucks, or Ben and Jerry’s. That’s the kind of stuff I would find at the library or find a these bookstore. I just inhaled that stuff. Specially stuff about Apple and Steve Jobs I was probably obsessed. I think the legend of entrepreneurs are most definitely something that was very attractive to me. I don’t know if I saw myself as being able to do that at that age but I was definitely excited by it and I don’t think I saw the little business I started with my friend to help teachers fix their computers as an entrepreneurial venture but I guess it was. Yeah I don’t know.

Josh Pigford: In college at some point you decide medicine is not for me. Was the transition to computer science specifically?

Amit Gupta: Yeah I started taking computer science classes, I took a lot of studio classes, a lot of psychology classes. I think all of it was interesting. The studio stuff was probably the most interesting to me but computer science was too and I think studio just felt good in a way that the other things didn’t. For whatever reason it didn’t feel to me like a serious major. I felt like I couldn’t just do art. I did computer science and then later I also did economics, so I ended up as a dual major economics –

Josh Pigford: Got it. At what point did you start what you would consider … Obviously you said you didn’t consider the little business with your friends to fix teachers’ computers and stuff a business but what was your first for you official here’s I’m starting this business with the intent of making money from it?

Amit Gupta: Yeah, so my freshman year I learnt HTML and I started helping clubs on campus make websites. I helped the student newspaper make their first website and just the career counseling office and a bunch of other organizations. This fellow student Tom in my class had started a business where he was helping small businesses create websites. I don’t know if he knew HTML himself but he wasn’t making the websites himself so he hired other people like me to make these. I remember learning a lot in the process but also being so frustrated because I’d make what I thought was this beautiful intuitive wonderful website and then all this feedback would come back from the pizza shop owner and it was. “Make this logo really big and make this other thing really ugly.” I would do it because that was a job because I was like I can do this better.

Amit Gupta: I think it was around then that I decided I wanted to do my own thing. I didn’t want to do that for other people. I’m still friends with Tom and maybe he’ll enjoy the fact that he inspired my entrepreneurialism in that way. During freshman year I found an internship working for a dot com in Boston called Thing World and I moved to Boston that summer, found an apartment with a friend of mine and we started working for this company together. I was already super into the internet. In freshman year I remember I was reading business 2.0 and Red Herring and Fast Company and all these magazines that probably don’t exist anymore. Internet 2.0, so I don’t know what they’re called. Just absorbing these stories about internet fandom basically. I went into this internship and kept learning a bunch there and that … I don’t remember what happened. Actually I’m mixing things up. Sorry freshman year I didn’t do that.

Amit Gupta: It was after sophomore year that I did that. In sophomore year I had started this website, so this is a year after I started working with Tom. It was called Amherst central and it was just like a home page, a one page website that had the campus dining hall menu, what was going on, on and off campus. Like campus events. Some funny quotes of the professor said, things that people send in and then links to useful resources around campus. The campus website wasn’t very useful to students at that time so we made this website. My roommate and I that was all about just being a useful home page, a useful portal and it became super popular. I think more than half of the campus was using it on a daily basis. I thought this is something I should take to other campuses this is going to be huge. This is when I was reading all those magazines.

Amit Gupta: That summer I got this internship and I started learning a lot at Thing World and after that summer I decided I was going to drop out of school and make this website that I had made from Amherst but for other colleges. There are three other friends involved at that point and I tried to convince them all to drop out with me and I convinced one.

Josh Pigford: The purpose of dropping out was to see if you can go all in and see how big you can make that thing become?

Amit Gupta: Yeah exactly. I read all about how people or kids basically were just writing business plans and going raising zillions of dollars and just pulling all nighters. It was this very romanticized nation of a notion of just investing everything into it. That was what I figured you had to do that’s what I wanted to do. I wanted to just go all in, find a bunch of money and make it as big and as fast as possible.

Josh Pigford: Was the goal to essentially … Did you want to connect any of those schools to each other or was it mainly the self-contained intranet thing for each given school?

Amit Gupta: It was really self contained. At that point, each campus we had I think two or three campuses by the summer. Each campus had its own discussion forum and people were spending hours and hours a day on this just talking about all manner of things. It was kind of creating those discussion forums and chat rooms that I had when I was a kid but it was specific to a campus instead of a whole bunch of random people from all over the place. I think that was really powerful because it became this place for all these people to talk about things that were going on in their lives in a way that they couldn’t easily before with people that were also experiencing similar things. The forum ended up taking on a whole life of its own but we were very careful to make each campus a silo because we wanted it to feel custom to your campus. We wanted it to feel that it was a website made just for students at your campus. There was very little cross campus communication.

Josh Pigford: What happened with that? I assume it ultimately did not pan out.

Amit Gupta: Yeah so I took time off and so did my friend Mike. We were 19, writing a business plan shopping it up and down in Manhattan and I think I recruited somebody from Thing World who was in [inaudible 00:16:36] to be our CEO. Found and an advisor. Basically talked to anyone and everyone who would talk to me to try to understand what I should be doing. What should go in a business plan? Who should we talk to? What are we supposed to do and leaned everything as I went. We ended up writing this plan we grew to 23 schools we raised money from angels. We raised like one and a half million dollars which seemed … I guess what really happened was we got two offers in the process of shopping it around and trying to learn everything we could. Got two offers to sell the company to other college focused companies.

Amit Gupta: One was public and one was private and we decided to eventually because we were having trouble raising money, we decided to sell it to one of the companies and we were supposed to go up to Boston to sign the papers. We basically agreed to do it. Then one of the people we talked to about investing called me up and home and he … I guess his son had told him about Amherst Central and the Daily Jolt which is what it’s called now because his son went to Amherst and he was a successful entrepreneur out in California and I told him what was going on, that we were about to sell the company the next day and he said something like when would your decision change if I was to wire a million dollars into your account tomorrow? I said yeah I guess it would.

Amit Gupta: Then he did and we ended up putting together this round with a few other people for a million and a half. That began this crazy adventure where we had started this tiny company in this room above my parents garage and now we were moving to Boston and hiring a guy away from the company I’d interned for. Renting an office space and hiring 27 people over the course of the next year and expanding to over 100 schools and having Ford as one of our advertisers. Getting in the Wall Street Journal. It was crazy times but you were correct it ultimately did not work out. We had this crazy year where it just we’re working like mad, had bunk beds in the office and I went home half the time and other half the time I slept at the office. Then bubble burst and we were supposed to be raising our next round soon and it was becoming more and more clear that that wasn’t going to happen.

Amit Gupta: The company wasn’t profitable yet and our advertisers started going away because when the bubble burst everyone decided the internet is just this fad, it wasn’t really a thing. Advertising on the internet is never going to take off, it’s never going to work so we knew we couldn’t raise money and we had to let half the company go and so it had … Probably the most painful experience in my life up to that point was half of the people in this company. All of them were friends, all of who were older than me and just doing it in the responsible way like on the right day of the week, with the right paperwork and just feeling so cold about it but also so pained that I have to do this to all these people who had bought into this dream that we were pursuing together.

Amit Gupta: Eventually I had to lay off another half of the company, but we did get it back to breakeven and made it work. Then a year later, I was pretty burnt out and I handed the company over to one of our first employees, and went back to school via a trip to India where I ended up working for the WHO. The company, survived for a few years, it was sold to somebody else and they sold to somebody else and then eventually it died in a whisper. I think I got a check for $3000 or something somehow. I’m not sure where it came from.

Josh Pigford: Big payout.

Amit Gupta: Yeah.

Josh Pigford: I think of like … You started this as … You would have been a junior in college I guess. Would have been as far as age goes 18, 19 … 19, 20 I guess.

Amit Gupta: Yeah.

Josh Pigford: What was that like as essentially a teenager having to take on all of … That’s a heavy burden to bear? What was that like for you being of that age?

Amit Gupta: It was just exciting. I don’t remember it being heavy. I remember it being hard just like physically taxing. Because I was working so many hours, but I was so excited about what we were doing, and so excited about the potential. It was just … I felt like I was really in the flow of it for two years straight basically. Even though … I felt like I was learning so much. I think it’s easier to get through something that’s difficult or get through something that’s taxing when you’re absorbing and growing and becoming better at what you’re doing all the time. It was super exciting. I’d never hired anyone before. I’d never rented an office base. I’d never negotiated a lease, I’d never done anything that I was doing there basically. We were doing a good job. We were doing a good job at the website, we were finally making mistakes everywhere, but it was working and that was incredible exciting.

Josh Pigford: You wrap up at daily jolt, step away from that stuff, and ultimately decide to go back to school, right?

Amit Gupta: Yeah.

Josh Pigford: What was the reason to go back to school? Was it just to finish what you had started?

Amit Gupta: I think the inner … Like I said, the internet bubble had just burst and I was really burnt out. I didn’t know if … It didn’t seem like there was going to be a way to continue to work on the internet at that time. School just seemed like the only other option really. Like I said I ended up leaving the daily jolt, in the middle of the school year. I went to India for three or four months. I just wanted to be in a completely different environment and I applied for this freelance position with the WHO to help with analyst and mental health program and development. Not computer programing, just making this course. I did that for a few months and it was something completely different. I came back and started school with this fresh perspective. Actually school was incredible the second time around.

Amit Gupta: I can’t believe that I didn’t even consider taking time off before or time off between high school and college. I think it’s something that everyone should either do or at least consider. Because it’s just … It opened my eyes to the fact that I’d just been marching through life just doing what I was supposed to be doing, and now is back at school. Everything seems so easy compared to working in the real world and starting a startup. All the things that I thought mattered, and all the things I used to care about or the insecurities I had just went away because I had done this stuff, and I’d done this difficult thing. School felt like a joy.

Amit Gupta: There’s just people everywhere who had gobs of free time, and incredibly smart professors who their sole job was to just teach you what you wanted to learn, and wow what an opportunity and what a waste of those two years that I made … Freshmen and sophomore year. Not that I didn’t go to classes, but I didn’t really appreciate it for what it was. It was an amazing experience to go to college twice and have the second time be so different and so much more fun.

Josh Pigford: My oldest kid is … She’s 15. It’s like approaching that … She starts high school in a few months and it’s getting those conversations started about what are you going to do after high school. To me the idea of … I think most people call it a gap year. The idea of going off on your own and just … To me whether it’s starting a business like you did, or going and traveling or just seeing the world and experiencing a lot of things. Then you get to come back and, I think the word you use is marching. For most kid’s lives their entire first 20 years is essentially being told, do this, now do that now follow these steps. You need a chance to do a reset I think. Like you said, start back with a fresh perspective. That’s interesting.

Amit Gupta: Totally, I think being in a real world shows you how hard the real world is even if you’re not working, if you’re traveling by yourself or something. That too would I think just show you how rough it can be out there and you’ve had just … Probably had this very protected life if you’re that old and you’re going to college.

Josh Pigford: Absolutely. You mentioned-

Amit Gupta: You just don’t realize it.

Josh Pigford: Started working at WHO. You get a frontline look at, or how hard it can be for a lot of people.

Amit Gupta: Yeah, totally.

Josh Pigford: You go back to Amherst again. Did you basically finish up your degree there?

Amit Gupta: Yeah I went back to Amherst.

Josh Pigford: After that, get your degree and then what?

Amit Gupta: Well I thought after I graduate that I would just move to Hawaii. Because many times in your life … Yeah why not. I wasn’t working it and it wasn’t like I would have to leave a job or something to do this in Hawaii or some place I always loved, because I’d visited a couple times with my family. I thought okay I’ll move. I bought a bunch of books. How to move to Hawaii, and I found an apartment on Craig’s list with a roommate. I figured all this stuff out, and then my mom got breast cancer. She’s fine now, but I decided I was going to stick around while she was going through that process. I was back at home now in Connecticut where she was. I think I’d started reading Seth Godin’s blog in college. He had posted something about looking for people to help and start something. I wrote to him, and I ended up meeting with him and he hired me.

Amit Gupta: Then it was my job to hire the rest of the team. I hired the rest of the team to start thing called Change This which was this nonprofit. Whose goal was to change people’s minds through blogs and spreading ideas virally through the internet. This is when blogs had just exploded everywhere. People just constantly talking of blogs. It was an incredible experience. I was able to stay at home with my mom and commute by car. I learned so much from Seth. Some because he taught me and gave me feedback on things that I was doing. A lot just from observing him, and the way he was acting and the way he would counsel people in our company, and how he would make decisions. After that launched, I ended up moving to New York City because I was already living in New York City at that point to work on Change This.

Amit Gupta: My mom was done with her stuff, and I figured everyone should live in New York at least once, at least for a year and so I ended up in New York. I ended up being there for about four years. In a lot of ways those four years jump started my career and really sent me in the direction that I ended up going.

Josh Pigford: What was it like working with Seth Godin, I guess I think on the front end of it. What was … How do you think you ultimately were able to get the job with him?

Amit Gupta: I don’t know. I wrote his this letter, and I think I told him what I had done in my life. I started this company in college, I dropped out, didn’t work out. I just told him what I was into, and I think I just wrote him an honest letter about who I was and he was interested. I didn’t think I would get the job because I wasn’t super into marketing and I wasn’t … I just felt I wasn’t exactly the right type of person that he was looking for. I think I just played to my strengths. I told him I was entrepreneurial and I was looking to start more companies in my life and that was what got me excited. I think he saw a use for me so he hired me.

Josh Pigford: That’s cool. You work there for a year or two or?

Amit Gupta: I think it ended up like a year-ish.

Josh Pigford: What did you do after that?

Amit Gupta: After that I moved to New York and I had known about this other guy Mark Hurst. I don’t remember how I got to know him either about I knew about his firm Creative Good and he did some really interesting usability consulting work. He was one of the first people if not the first people who did that kind of research for websites. He did them for really big name websites and has started this company around it and a brand around it. Like a conference around it. I reached out to him just because I was interested in him, and he made me coffee and I just told him I was really into what he was doing. If there’s any way I could help I’d love to do that. He ended up hiring me as the contractor for some projects and I learned how to do usability consulting, enlisting labs. Those things where you’re sit in a room and somebody and they’re using a computer, and there’s a way mirror and other people are watching behind it.

Amit Gupta: Trying to understand why the person is doing what they’re doing and what’s going on in their head as they’re doing it. That was actually super useful too. The work was consulting work and to me as a young kid in his 20 years is super exciting because I got to travel all over the place, market these big companies. I’m sure it would have gotten boring after a while but I didn’t stay at it long enough that it would become boring. Like I said I idolized Apple when I was a kid. One of the companies I got to work with was Apple. I spent out in Cupertino doing these listing labs. I was moderating them, someone else was, someone who was way more experienced that I was. I got to take the notes and do the analysis. I ended wire framing a bunch of screens for the online store, and they still use those layouts and everything, but updated colors which was cool.

Amit Gupta: The useful part is that I got to see how Apple worked on the inside a little bit. I got a peak into that because they were a dozen people from their team who had been on these session and we’d be talking to them after. Gosh they’re just like any big company, they’re so boring and they’re … They worried about the wrong things and they were arguing about things that seemed obvious to me. I was this head strong 20 something, so of course I thought this. I think the lesson was just every big company is the same on the inside. Everyone, whether we were working for Pearson or Apple people were just people and it was so much more fun to do my start up and to make decisions quickly and to do the things that we were doing than it seemed like it would be to work for this company. I think that was also a turning point. I realize didn’t want to work for a company even if it was one I idolized.

Josh Pigford: Where would you say at this point in your career you … At that point in your career that your interest lied? You had obviously started your own company. You were doing … Had done probably just about everything you could as far as tasks within that company. At this point would you say you were more interested in the usability side of things or I guess what was … Where were your interests at that point?

Amit Gupta: Yeah, I think from the start my passion was in design. From the point I learned HTML and started designing websites that’s how I saw myself as a designer. The usability stuff was useful to me as part of my design practice in understanding how the user actually fits into that and how the assumptions I make as a designer may not actually be true. How important it is to … Actually talk to users and watch the users even more so and to understand what they’re running into. I still saw myself as a designer. When I was living in New York I ended up doing a lot of other stuff. I ended up … I was getting really into the internet. The internet was popular again and gaining steam. I was really in tune with what was going on out on the west coast. I ended up organizing this thing called bar camp which was on conference for just internet and tech.

Amit Gupta: I got a friends company to loan us their office space over the weekend and basically organize this two day event with a few other friends. Where everyone slept over between Saturday and Sunday and no sessions were planned. Everyone had to participate by running a session or helping someone run a session and it was all planned ad hoc. Anyway it was I think, 200 people showed up too from all over the place, and I ended up organizing a couple more of those. After that other events in the tech space in New York because, through organizing that first one I became really visible in that space and the New York tech scene was still really rapidly developing but it was very small. Again I saw myself as the designer but I was doing all this other stuff. I was doing usability consulting, and I was organizing these tech conferences which I’d never done before.

Amit Gupta: Just I was looking for what was interesting, what was going on. Where I could learn something or meet interesting people.

Josh Pigford: You started doing thee … Were there multiple bar camps at the time or was it just a one off thing?

Amit Gupta: The first one was out here I think in Silicon Valley and the second one was the one I organized in New York. Then I don’t know where the third was but there were hundreds after that all over the world. The original organizers set up a template that help people organize them and coach them through it.

Josh Pigford: After you had spent at Creative Good, what did you do after that?

Amit Gupta: Well I think I was still doing Creative Good when I start Photojojo. Creative Good was just a consulting gig. Every time a project came along I’d be working on that for a few months or a few weeks whatever it was. It made me enough money that I could live in New York and I could also organize these events and work on my own projects. I think over the course of my career up to that point I probably designed six dozen websites that I had never gone live. Just ideas that I had for things or projects or whatever and I was constantly talking with other people about things that I might make or things we might make together. I remember bouncing a lot of ideas against Seth and against people he had introduced me to. I was always tinkering at something, always trying to come up with some idea for some website or some project that I would want to do.

Amit Gupta: Photojojo started in that time period. I think that I … I was super into photography as a kid and then later in college I was really into it. When I got to New York, it’s just such a photogenic city and I had finally … Digitals were finally cheap enough that I could afford one. I got one as I was doing “street photography” started a photo blog. Photo blogs were really big then because everything in the internet was exciting. I remember getting to do a talk about my tinny little photo blog at the Apple store in Soho, which was so cool. I saw more and more people getting excited about digital photography, and it was getting cheaper and possible. It really seemed like it was something that was going to make photography a lot more mainstream. Because before that, it was an incredible amount of work to take photos and each photo cost you money because it cost film.

Amit Gupta: Cameras were expensive, and it took a week or two from when you submitted your film to the cheap places to get it developed to when you got it back. Unless you’re really artsy, you’re really into it or really serious about it, you weren’t taking photos except at birthdays and holidays. Which is something that seems so foreign to us now because we take photos constantly, back then you just didn’t. I saw people taking all these photos with their digital cameras after they got them and those photos would just end up on their computers. They would forget about them because there wasn’t really anything to do with them. I was familiar with all the photo magazines and the media out there on photography because I was into it in high school. It was really for gear heads. It was for mostly guys and it was for guys who wanted to know about the latest canon lens or the latest high tracking thing that cost $5000 and there wasn’t [inaudible 00:38:38].

Amit Gupta: I thought I could make something where I helped ordinary people do more of their photography. Be more creative, do more with their photos after they took them. In other words it would be for ordinary people. It wouldn’t be a site with a black background and white text, which for some reason all photography websites here. It would be a white background and it would have lots friendly looking pictures and it would be short and easy. I also felt there were just too many blogs, too many blogs. Every blog was posting 100 posts a day because that’s what you had to do, and so I decided to go the opposite direction. Which is probably something influenced by Seth because he always gets you challenge the ideas that you’re absorbing and try to find different ways to do things. I thought okay, I’m going to go retro, start this email newsletter.

Amit Gupta: It’s only going to go out twice a week instead of blogging 10 times a day. It’s going to be three paragraphs long, and just have one picture. I’m going to make it easy so to mimic the email easy to just look at and archive. Because at the time mostly newsletters, they were super long full of a million notes and just too much text.

Josh Pigford: When you started Photojojo, did you think of it as a business you were starting or just very much a way to scratch your own itch with this hobby?

Amit Gupta: I did think of it as a business. I had seen daily candy become really successful. It was newsletter mostly for women in New York City original. I saw that there was potential for a business like that. I thought yeah, I’ll start this email newsletter, and it will be for people who are taking photos and maybe after I get thousands of followers I’ll be ready to sell ads.

Josh Pigford: Got it. How did you transition? Eventually it turned into like an e-commerce operation where you had actual products.

Amit Gupta: Yeah. It morphed a lot. I think well it launched kind of by mistake. I’d send it out friends for feedback and somebody sent it to … Someone at 37 signals who put on their blog and that’s like no. There’s only one email that was on the site and I scrambled to get it going after that. I think that I just … I was caught in the momentum of it for a long time for several months. Because it kept growing, people were telling their friends about it. I wasn’t doing any advertising, I wasn’t spreading the word in any other way, friends would just tell people. The list kept growing, we kept getting good press. I was just scrambling to write quality content and write good stuff every week. I started trying to sell ads and I sold some, Mailchimp was a really early supporter and several other companies. It was working but it was such a hustle to sell ads. I realized I was pretty much the world’s worst ads salesman.

Amit Gupta: I didn’t want to do it, I had no fun doing it and I was crappy at … I was really bad at doing things I didn’t like to do. Selling ads is one thing I didn’t want to do. It was unfortunately the only way we could make money. I think maybe six months in or something I saw this product that was really interesting for showing off your photos. It was just this metal wire with a bunch of tiny magnets you can use it to attach your photos to the wire. I couldn’t write about it because it wasn’t available for sale in the United States. Most of our audience back then It was in the United States. Then it occurred to me that maybe I could just buy a whole bunch of them and then sell them on the site and that would help me learn about them. That’s what I did. I found somebody who would sell them to me after making all these phone calls to the UK and trying to send emails to people who wouldn’t respond to me and eventually finding someone who would sell me a whole bunch of them.

Amit Gupta: I set up a fulfillment center on the kitchen table in our apartment in Manhattan. After I was working on the newsletter all day, it would be 10:00 o’clock at night and I would look at all the orders that had come in, and print out PayPal, shipping labels, box up these things and then wheel them to the 24 hour post office. Do that and come back home at like 1:00 in the morning and then start all over. I just did that for days and days and it seemed to be working. People were buying this thing. I did more of it.

Josh Pigford: What? Were your customers coming from the newsletter, was that the primary source for you?

Amit Gupta: Yeah, almost entirely from the newsletter, I think eventually I got … Started realizing that I could promote these products outside the newsletters. I would also start to write different blogs that I thought would be interested about them, and that was huge. Figuring out which specific blogs would be interesting in which specific products.

Josh Pigford: After you realize people continued to buy this products, you decide to start selling more of them, different types of products?

Amit Gupta: Yeah. Every time I came across something interesting I would think whether or not it was something I could sell. I was trying … I was looking for stuff that was small and easy to ship and unique. Something that you didn’t see a lot or something that people Something that if I sold it I’d be introducing it to people, and that felt really important because, there’s a million places online where you can buy stuff. I wanted to … I want it to be the exclusive place where you could buy the things that we were selling. Or at the very least I want them to be the first place that people found the thing that we were selling.

Josh Pigford: At what point did it transition from hey this thing is a newsletter to hey this thing is a store?

Amit Gupta: I think took quite a while for me to realize that. I think it was after I’d moved to San Francisco, after I’d hired some people. I think my second or third … I guess my third hire was somebody to help with the store. She was somebody who was basically just out of college. Had done an internship after college but that was it. I wanted somebody who was pretty inexperienced, but wanting to try something new and try it in different ways. I tasked her with exploring this idea of doing more with the store. I think we had a dozen products at that point. The revenue was mostly still advertising. I saw so much potential in the store, and eventually I think that I only took another year or so, but eventually I stopped caring about the advertising and really focusing just on the store.

Amit Gupta: Then the store really took off. People had started to come to us not because of the newsletter but because of the store. We were finding stuff that was incredibly interesting, and we started to make trips all over the country, and then eventually all over the world. Looking forward to source stuff that you couldn’t find elsewhere. The business became about the store, and we eventually started to make our own stuff because at some point we run out of interesting things that other people were making that nobody had ever heard about. We started to manufacture which was a whole another adventure.

Josh Pigford: Between the newsletter, basically producing content, between that having an eCommerce where you’re selling products and then actually manufacturing them yourselves, what was your favorite part? Which one of those I guess really interested you the most?

Amit Gupta: Well, I think I like them all, but I loved making your own stuff. Because it’s just so exciting to design something from scratch, design a new product and the thought should exist in a world. The process of doing it was miserable. It was something like selling ads, working with these factories and finding people to make something well was just so difficult. There’d be so many issues and so many quality problems you had to deal with, and it would just take so much longer than you had thought it would. It’s so satisfying at the end of it to have something that you just thought up in your mind and then it existed in this perfect object and in this beautiful package that you designed and then got to send out. I think that end product was really satisfying.

Josh Pigford: Did you guys get to 100% selling or manufacturing your own stuff or was it always a mix of the stuff you were sourcing plus your own stuff?

Amit Gupta: It’s always a mix. I think that was important because we wanted to be a source of stuff that we thought was the coolest stuff even if we didn’t make it. We didn’t want to cut out the things that we liked or thought were really amazing just because we didn’t make them.

Josh Pigford: You’re doing that for a few years you were manufacturing your own stuff. I’m assuming and then, did you … At what point did you decide to sell the company.

Amit Gupta: Well so we were … I think we’re maybe six or seven years in and we’d grown quite a bit. Our fulfillment wasn’t out of the kitchen table anymore. I moved to San Francisco. We’d found a warehouse … I guess at some point we moved the fulfillment to my mom’s house, and my mom and I were doing it together. Then I moved to San Francisco and then we found a fulfillment warehouse. My mom ended up doing customer service and later inventory management. She ended up working with the company for seven or eight years. Aside from her the company grew to maybe 28, 29 people. Some local, some remote, some freelance. I was just having a blast with it. I think we were growing in lots of different ways. Certainly in revenues and profits, doubling every year, doing well. I was really passionate about starting another brand like Photojojo both for work. For products around work in the office and so I was working on that.

Amit Gupta: I think this is 2011. When I got a cold and I was home for a week feeling sick. For some reason I couldn’t kick the cold, so I went in to the doctor and had a blood test because he thought it was mono. The next day he called me and he told me that I had leukemia. I said what are you talking about? He’s like yeah you have leukemia and you … I can’t even believe you walked into the office. You should basically be dead right now. You should get to the hospital immediately and start treatment. I remember hanging up with him and calling my dad because my dad is a doctor and talking to him about it. Meanwhile Googling sites and Googling leukemia, looking up everything I could to try and understand what was going on. He suggested I go to the hospital and get some antibiotics and get some blood transfusion that I would need, and head to Connecticut to start treatment.

Amit Gupta: That’s what I did. I spent the night in the hospital getting these infusions and antibiotics and then go on the next flight the next morning. I got there and got to New York. My parents drove me to Yale New Haven, I got admitted to the hospital that night, and then I was basically set into this hospital bed and they started pumping me full of chemo. It was just … It didn’t seem real. It didn’t at all seem like real life because-

Josh Pigford: What was the timeframe here between the time you’ve like, hey I’ve got this little cold to I’m in bed getting chemo?

Amit Gupta: I think I got the cold a week before I went in to see the doctor, and then the day after I got the diagnosis I was at Yale. It was about a week.

Josh Pigford: That’s insane.

Amit Gupta: I woke up the next day and I just … I remember thinking what is … This does not seem real. This is some weird dream that I’ve no idea what’s happening but it’s not real. Then obviously that subsided after a while. I accepted that it was real. Unfortunately I still had this company to run because I had 20 something people depending on me and I’d been out for week and still working from home. Now what was I supposed to do? To make matters worse, it seemed like what I had was an aggressive for of leukemia. My odds of surviving it were not very good. If I got stem cell transplant the odds improved to 50–50. I was likely going to be in the hospital for a month and it just … It was a shock. The next two years of my life I don’t know how much detail you want me to go into but that was … The next two years of my life were very different.

Josh Pigford: I can’t imagine going from the, everything feels right in the world, this thing is actually working. Photojojo is working really well. You’ve mentioned you’ve got all these ideas for a new brand and then … Overnight the entire thing completely changes for you. What was going through your head at that point?

Amit Gupta: I think it was a lot of different things. At first thinking it wasn’t real and then later just feeling sorry for myself thinking it was so unfair, and then feeling angry interjected. Went through all the emotions that you’re supposed to go through I guess.

Josh Pigford: Sure.

Amit Gupta: I think that first week was really painful. One other thing that was really hard was just having no control when you’re a patient in the hospital. Your life is governed by the staff of the hospital, and they’re there to make sure that you stay alive. It doesn’t really matter if you’re happy or comfortable. It matters just that you’re still alive. I remember almost this feeling outrage that I was never allowed to sleep for longer than an hour or so because someone had to run a blood test. That happened to me for weeks and weeks. I never knew when was … When I would have time to do work or time to myself and had no privacy whatsoever. I was constantly being … My body was being manipulated in different ways to treat me. It was such a stark change from being your own boss and being in control of your days and your time and knowing exactly what’s going to happen.

Amit Gupta: That was difficult too. After that first week I think I’d come to terms with what was happening. I had written an email to my staff and to my friends. I had told them what was going on. At that point I’d found out that the transplant wasn’t going to be possible, the one that was going to raise my odds to 50–50 because there was no matching stem cell donor in the registry. Apparently for minorities, it’s pretty difficult to find a match because there just aren’t many registered donors. I shared all this news with my friend and the staff and family. I just started getting this outpouring of emotions from all these people. There was like 30 people that I had emailed, so many more people started to find out and to write me and to send me things, and to ask me how they can help.

Amit Gupta: Several friends of mine decided that they wanted to do more. They asked if they could organize some events to try to get some more stem cell donors in the registry and of course I said sure. The first event was organized by my friends Tony and Isuru in New York, and then my roommates in San Francisco organized an event there. A few other friends decided that they wanted to help organize more of these events. They started doing a daily call where they would checking in with each other and brainstorm new ideas for getting more events going, getting more donation events going, more places that I could do press outreach. The stuff I feel in a lot of ways saved me. Not only because it ended up saving me but because, emotionally it gave me something to do. It gave me something to fight for, it gave me some hope. Even though the doctors had told me it wasn’t … It wouldn’t hurt anything to try to do drives. They told me the chances of us finding a donor in the time period I need one were more basically zero.

Amit Gupta: It was one in 10,000 or one in 20,000 odds if any one person could be a donor. It was technically almost impossible to get that many people in the registry that quickly, especially south Asians. Especially if you’re targeting so narrowly. They said go ahead, but don’t raise your hopes. I did. Of course I raised my hopes because how can you not? The next several months were so painful, a lot of chemo, a lot of … My hair falling out, a lot of physical pain. Just things about my body breaking and feeling that I didn’t even know could break or fail. Pain that I had no idea I could feel. Working through all of it, keeping up with what was going on with Photojojo and doing conference calls, in between conference calls, doing press for donor drives. Then we got press in all this different tech sources like Wire and tech crunch. We also got newspaper press we also got NPR. Seth did an interview on the ethics of bone marrow donations.

Amit Gupta: Someone else introduced us to Sanjay Gupta who did an interview with me on CNN. Someone else got Aziz Ansari and Chris Pratt to do a PSA, and we just had all these different people working on all this different angles to get the word out and to get these events organized. We did hundreds of these in United States and dozens more on the world, India. Those places we had to raise the money ourselves. People were contributing money to make this happen. Eventually we found to one but two perfect matches for my stem cell. Quite literally saved my life. The registrants that we got because of those drives that my friends organized had ended up benefiting dozens more people that I know about and maybe more years to come. Not only did it save my life but it saved all these other people’s lives. Holly crap, I guess the most-

Josh Pigford: Honestly it’s one of the amazing stories of people just coming together and then this thing snowballing more than anybody could have ever hoped for. You couldn’t have planned for something like that to take off the way it did.

Amit Gupta: No, definitely not. I think personally I’m just … I’m really bad at asking for help. It’s a weakness I have and I don’t think I could have asked for it unless I was dying. I couldn’t have asked all these people, and I didn’t really have to. These people came to me, but I … Once people started helping I saw there was hope. I started reaching out to people that I knew and people that I’d known. I think years of nurturing the various communities around the internet or in New York City or in San Francisco. Helping people wherever I could, all those things came back to me in those months. All those people that I had somehow touched or influenced decided that they wanted to help keep me alive. I’m so thankful because there’s no way I’d be here otherwise.

Josh Pigford: What did the doctors say when you found two donors?

Amit Gupta: I think they were very pleased, very surprised. They also got interviewed by many of the … By a lot of the press that was coming into my hospital room which a minor annoyance at times. Because they’d had to find times when the nurses weren’t coming in and get someone to hold the door closely while I would do the interview or whatever. I think it helped a lot because they’re always trying to get more people into the registry and get more donors and raise awareness. I think they were blow away by what started to happen around me and very pleased by it too.

Josh Pigford: You’re doing all this stuff for months, chemo. You found some donors three or four months in or longer or?

Amit Gupta: Yeah, about three or four months.

Josh Pigford: You find a donor, and they do the stem cell treatment and then what?

Amit Gupta: Prior to the stem cell treatment they give you basically the highest dose of chemo that you can withstand without dying. Once you get the chemo, your bone marrow is dead, you have no ability to produce blood cells and these new stem cells go in, and they’re waiting. For several weeks they’re waiting to see if the stem cells take hold. If they make their way to your bone marrow and start producing blood, and eventually they did. Which is totally like science fiction because now you’ve got this other person’s blood with this other persons DNA and this other persons … Basically identical to this other persons red blood cells and platelets and white blood cells but you’ve got your own organs. You’ve got this big problem actually because you’re a new immune system. Those white blood cells see your body as a foreign body because it doesn’t match.

Amit Gupta: The next year is really about recovery because you’re on a whole lot of drugs, something like 25 different drugs that you take several times a day, and a lot of them are all about trying to keep your new immune system from killing you. Eventually you taper off all these different things. I was very weak, could barely walk. Would get fatigued really, really quickly. It was just really hard to do anything in the next year. For anybody who goes through this it’s really about trying to get back to a new sense of normal. Where you’re still … You probably will never get back to where you were before, but hopefully you can go back to work and hopefully you can be normal. The first 100 days you’re in isolation, you can’t go outside you can’t see strangers or be in crowd places. Your house has to be a clean room environment because your immune system is so young and so delicate and you can get sick easily.

Amit Gupta: For me it was really … I was so grateful to have this time because when I was in the hospital room and I was going through it initially I really didn’t think I was ever going to leave. I thought that hospital room was going to be my prison. I remember thinking about all the different things that I’d never done in my life and all the places I’d never gone. I’d lived a really rich life and I’d gone to all these places but there’s so many more places I wanted to go and so many things I wanted to do. I’d made money with this companies. None of that money was going to help me if I was just going to die in this hospital room. When I got out I think I was really … I was itching to go do those things.

Amit Gupta: I was itching to travel or to learn how to fly a plane or get a delorian or just do all the things that I wanted to do in my life that I hadn’t got a chance to do. Get a dog. In a 100 days I adopted a puppy and I started making plans for a travel and for all those things that I would-

Josh Pigford: I guess at what point did you step back from Photojojo in that whole process?

Amit Gupta: In that first year I think I realized that I needed to sell the company because my odds with the stem cell are better, stem cell transplant were better, but they’re still only about 50–50 that I would make it through the next five years. I didn’t want to end up back in the hospital with leukemia again, and have regrets about how I’d spent the time I’d gotten outside. I knew that I couldn’t go back to San Francisco and just be working crazy on this thing that I loved even though I loved it because I would regret it, or might regret it. I started the process of finding a buyer which meant hiring people to replace me, hiring a designer to replace me. Hiring other people to show other roles and similar to how when I raised money, [inaudible 01:05:10] boot straps. I didn’t have any investors. I didn’t have anybody who was connected to it in a way that would incent them to look for a buyer, so I was on my own.

Amit Gupta: I basically just started talk to everyone calling up people, other entrepreneurs, investors I’d met over the years and asking them what I should do and how I should do it and who else I should talk to. That process just spidered. I eventually found someone to sell the company. It took me I think two years from the time of transplant approximately, to be able to leave it. Because I didn’t want to just … I didn’t want to let it go. I wanted it to be in a good place, it was important to me that it survived. That the people who worked there continued to have their jobs and to enjoy their work, and it just took a long time to find the right fit.

Josh Pigford: What do you feel … We touched on this a little bit earlier how you had been involved and all these different things over the years. You felt like that community aspect had come back in a really positive way obviously to help rally around you when you had your leukemia diagnosis. Do you feel … Do you feel like the community aspect of it was, you forming these communities was an intentional part as a byproduct of your personality or were you … Were you always wanting and looking for a community? Has that always played a role for you?

Amit Gupta: Well I’m an introvert. It’s not something that often comes naturally to me, but it’s something I’ve really pushed myself to do. I think that I … I don’t know, I love hearing people’s stories and I love hearing how people do what they do and how they got where they got. It’s very easy for me to talk to people one on one and just ask a million questions and get to know them. It’s much harder for me to be in a group and do something like that. When I organize events and had to get up and talk in front of a lot of people that was super hard. Forming those relationships ended up helping with … Eventually helping with saving my life, those were largely formed one on one. There are conversations that may have come out of bar camp or the other developer events that I had organized or Photojojo or Daily Jolt.

Amit Gupta: They were relationships that I had formed through lots of just one on one conversations and things we organized. It just was a lot of once on one relationships that eventually paid off. I don’t think there’s anything intentional behind it. I don’t think I was trying to know or trying to meet people or trying to meet a certain number of people or anything like that. It was just that I was interested.

Josh Pigford: I guess what are you up to now?

Amit Gupta: Well so I have done a bunch traveling and knocked off a lot of the things on my bucket list since I got out. Then since then I’ve really been searching what it is … What is it that I should be doing or how do I want to be spending my life. It’s a tough question for me to answer because there’s a lot of things I want to do. I’ve also started to realize how important my family and friends are to me. Spending time with them is really important, spending time with my brother’s family and with my parents. I’m optimizing for that and I’ve also started writing. It’s something that I’ve always enjoyed but never really done seriously, never done fiction. For the past year or so I’ve been doubling in writing short stories and trying to improve my craft and seeing if that’s something that I might eventually enjoy. Right now I just find it torturous.

Amit Gupta: I like the idea of exploring some other concepts that people around me here right now in San Francisco are working, on some of the things we’re working on what those things were ubiquitous might look like 5, 10, 20 years in the future.

Josh Pigford: To me the idea of almost being … I don’t know that constantly exploring or searching, but I feel more people are much more comfortable now than say our parent’s generation of not doing the same thing for 10, 20 30 years. We can just hop from thing to thing that’s fine.

Amit Gupta: Totally, and some of that is out of necessity because I think that stability is just unavailable to our generation. I think in some ways it’s a blessing. I don’t think anyone has only one thing that they’ve wanted to do in their lives. I think that’s pretty rare. I see it as an opportunity. It’s part of what’s driven … Actually some of my stories because I’m interested in what happens in the future if universal basic income becomes a thing. If people can work less because they chose to or because they have to, what does that world look like? I’m pretty optimistic. In general I’m pretty optimistic. I see a lot of good coming from changes like that because, it seems crazy to me that we have this default where we work 40 or more hours a week, and most of our weekdays are just taken up by work and often our evenings and weekends too.

Amit Gupta: Not that work isn’t good but a lot of people don’t really enjoy their work. It’s a tragedy that we spend so much time on something that so many of us don’t enjoy. I really hope for a future where that is less the case.

Josh Pigford: I totally agree. How can people get in touch or keep up with what you’re doing?

Amit Gupta: They can follow me on Twitter or Instagram I suppose. I’m always available on email and my website has my email on it.

Josh Pigford: Fantastic, cool. Well that’s all I got man. All this stuff we could really, really deep dive into. You’ve got an amazing story and I’m glad that I got to hear it. Thanks for hoping on the call.

Amit Gupta: Thanks for having me.

Josh Pigford: Alright there we have it. Amit Gupta thanks for listening this week. If you need revenue analytics and insights check out If you have any feedback I would love to hear it. Shoot me an email or on Twitter @shpigford. Head to to listen to lots of other episodes, with lots of other founders. If you enjoyed this a rating on iTunes goes a heck of a long way. Thanks again and see you next week.

Josh Pigford

Josh is most famous as the founder of Baremetrics. However, long before Baremetrics and until today, Josh has been a maker, builder, and entrepreneur. His career set off in 2003 building a pair of link directories, ReallyDumbStuff and ReallyFunArcade. Before he sold those for profits, he had already started his next set of projects. As a design major, he began consulting on web design projects. That company eventually morphed into Sabotage Media, which has been the shell company for many of his projects since. Some of his biggest projects before Baremetrics were TrackThePack, Deck Foundry, PopSurvey, and Temper. The pain points he experienced as PopSurvey and Temper took off were the reason he created Baremetrics. Currently, he's dedicated to Maybe, the OS for your personal finances.