How the internet helped save Amit Gupta


Amit’s colourful career path has only two constants: purpose and fun. The first opportunity to prove his entrepreneurial spirit came early, when he oversaw a staff of 27 as a teenage CEO of his own web startup. With various roles and stopovers along the way, Amit then turned a simple newsletter for friends into a quirky, popular online store for photography aficionados, called Photojojo. It’s hard not to admire Amit’s dedication for creating meaningful opportunities while putting fun first. And as it turns out, even a life-threatening illness has no chance against his tenacity.


This interview was first published in Offscreen Magazine Issue 10. This issue is now sold out, but many other back issues are still available.

[Offscreen] Amit, can you please describe your childhood growing up in Connecticut? How did your background influence the career choices that followed later on in your life?

My parents are from India, and none of the other kids at my school had immigrant parents. I didn’t even know English when I started school. It’s funny in retrospect, as a kid I wanted to fit in so badly — to be like everyone else. Then I grew up, and it turns out that everyone is the same and it’s our differences that actually make us interesting. I spent a lot of time trying to reconcile my life outside versus inside the home, trying to fit in. I don’t do that anymore.

My dad is a doctor. He would leave for work before I woke up and return late at night. He worked weekends, and sometimes got called in the middle of the night. He’s incredibly nice to people. If we went out to dinner within 100 miles of where he worked, there was a good chance someone would come to our table and gush about him and make him blush. Working hard and being kind was something he really valued, and it’s something I subconsciously took from him. My mom worked hard, too (I can verify this, as years later she would work for my company) but she also had a mischievous and playful side. She liked making trouble, pushing boundaries. I definitely took a lot of that from her.

I went to a very competitive high school, but was a pretty quiet kid, always glued to a novel. I took photography classes and talked my way into doing an independent digital photography study before digital cameras were widely available. My camera at the time was an Apple QuickTake 150! I wrote games for the TI-84 calculator, learned programming by typing in BASIC code from the backs of magazines, and deployed prank programs on the Macs in the computer lab (and once, dry ice in the school toilets). I learned QuarkXPress to do layouts for the school newspaper, was in the Stock Market Club, and started a little business making computer upgrades and repairs for teachers at my high school. I was a little Steve Jobs fanboy.

[Offscreen] Do you remember that crucial moment when technology ‘clicked’ for you and you wanted to get involved more heavily?

I don’t think there was a single moment… I was just always a tech geek, always working on some tech projects. Among my friends I was the first to have the Internet at home. In high school, some friends and I programmed a little remote-controlled car using a Basic Stamp to solve and navigate a maze. Whatever little money I made usually went into getting some tech toy or making a project.

My college major was in computer science, but I was also taking a lot of studio classes like drawing, printmaking, etc. Then I discovered the web. I had a little crush on a girl that lived upstairs in my dorm and she knew HTML, so I got her to teach me. And the web became a way for me to bring together my interest in art and in computers.

I probably made a dozen variations of a personal website. Silly stuff, stupid stuff. Then I offered to make websites for anyone — I just wanted to get better. When I finally got paid, it probably worked out to be a few bucks per hour, but every project was making me better.

At one point a friend started a company making websites for small businesses, and I began doing contract web design work for him. That was the time of online communities like k10k, Dreamhost, and so on. When I discovered magazines like Fast Company and Red Herring, I started getting excited about the business side of the web.

[Offscreen] In 1999, before the first dot-com bust, you dropped out of college in the second year of your degree to start a venture-backed company as a 19-year-old. How did that come about?

During the first summer break of college, my roommate and I created a website called Amherst Central. It was a site for students, by students: on- and off-campus events, dining hall menus, class schedules — everything a college student needed. Suddenly the whole campus started using it. Mid-way through that year we changed our name to The Daily Jolt and expanded to other colleges. By this point my grades were starting to suffer because I was so distracted by the work, but I somehow made it to the next summer break.

During that break I interned for a startup in Boston by day and worked on The Daily Jolt by night. By the end of the summer I knew I had to choose between school or our startup. And so I decided to drop out of college. My parents were incredibly supportive despite the fact that I moved back in with them and set up an office above their garage. My partners and I lived and worked there for six months. I was 19 when I put together my first pitch deck, hired a CEO, went to VC meetings, fielded acquisition offers, and worked non-stop. Eventually we raised an angel investment round of $1.4 million and moved to Boston to ‘make it happen’.

The next year felt like it was on fast-forward. We had bunk beds at the office; I used them often. For a year I did nothing but work and sleep, mostly the former. We grew to over 100 campuses and 27 people on staff. Rolling Stone and The Wall Street Journal wrote about us.

Then the bubble burst. I was the youngest person in the company when I laid off three quarters of our employees. The next year was the hardest of my life up to that point. I got the company back to profitability, but was completely burnt out by the end. I left to live in India for three months and joined the World Health Organisation doing work far removed, both in character and geography, before returning home to finish college.

In the end, The Daily Jolt didn’t make me a zillionaire. But I learned more in that year than I ever have since. I learned how to manage and inspire people (and how not to). I learned that hiring good people is really hard, but having to let them go because you can’t afford them is ten times harder. I never wanted to do that again. And I learned that I loved working hard and loved making things. I’d been bitten by the entrepreneurial bug.

I learned that hiring good people is really hard, but having to let them go because you can’t afford them is ten times harder.

[Offscreen] At one point a particular book caught your attention. It would change your career path, see you move to New York and eventually return to the web and tech industry.

I had finally graduated college when I came across Unleashing the Ideavirus by Seth Godin, after having followed his blog for a while. So when I saw him put up a callout for interns to help build a new project, I eagerly applied. I met Seth a few days later, he accepted my application and I got to work building the rest of the team for that project.

In just three months, under his leadership the five of us created ChangeThis, a platform for spreading important ideas via blogs. It was still super early days for blogs and RSS back then, so a lot of what we were doing had never been tried before. Our advisors were folks from well-known companies, like NPR and Union Square Ventures, and our authors included Malcolm Gladwell, Tom Peters, and Guy Kawasaki. It was incredibly exciting to take principles from his book and turn them into an actual tool.

Working for Seth is hard to describe. He’s quick, smart, kind, generous. He’d come in for an hour to brainstorm and leave us with two weeks worth of ideas. He’d push us hard, but he’d listen, too. And he seemed as concerned with our personal growth as he was with the project’s success. I’ve learned more from him than from any other person.

After the project launched, I moved to New York. Everyone should live in New York at least once, I thought. I continued to run ChangeThis while taking on new freelance projects, like web usability work for Mark Hurst at Creative Good. New York was a lot of fun. I lived in a commune for a while; organised huge tech ‘unconferences’ that involved sleepovers at the offices of CollegeHumor and Microsoft; camped a night in the middle of Times Square; rented an entire floor of a building in midtown for a couple of years and threw parties with friends. I met an amazing array of people!

[Offscreen] Does Seth’s work still have a particular influence on your outlook on life and work? What principles did you take away from working with him that still guide you today?

Undoubtedly. There are too many takeaways to count. But let me share one.

When I first met Seth, deep down, I really thought marketing was evil. A necessary evil, maybe, but still an evil. Working with him changed my attitude. I realised that building something awesome is only half your job as a creative person; the other half is making sure the people who would benefit from your creation hear about it. It’s not advertising, it’s not spam. If you have something that will improve people’s lives, it’s your moral obligation to spread the word. And if whatever you’re making doesn’t make people’s lives better, why are you making it?

Like any designer, I had folders full of old projects. Websites that never found an audience or took off. After meeting Seth, I never again started a project without knowing exactly how I’d reach the people who would love it.

[Offscreen] During your time working with Seth you came up with the idea of the Jelly. To be honest, I was a little confused by the concept when I first heard of it several years back, but I’ve now been to many Jellies and really enjoy them. Can you explain what it is and how it came about?

My good friend and roommate Luke Crawford and I both worked from home. We both missed the camaraderie and idea-exchange that came from working with people face-to-face, though we didn’t miss the office politics or interruptions. So once a week, we opened up our apartment to friends to come and work on their projects. We got writers, programmers, artists, industrial designers, and everything in between. We called it Jelly because there was a bowl of jelly beans on the table when we were brainstorming, and it sort of just stuck.

A year later, Jellies were taking place in more than 100 cities and NBC brought a camera crew to our apartment to do a story on this odd phenomenon. Coverage in Wired, on NPR and CNN followed. The quality of conversation and people were really astounding. My friend Jake Lodwick, co-founder of Vimeo, was an early attendee, Guy Kawasaki came to speak at one, and so did Seth Godin. Our San Francisco event was hosted at the apartment of my pal Joe Gebbia, who launched Airbnb at one of them.

[Offscreen] In the midst of all this, you launched Photojojo as a personal newsletter for friends. Did you always hope for this project to grow into something bigger?

I was always a shutterbug and had spent a lot of time in school developing my skills. When I moved to New York an incredibly photogenic city and a sea change in photographic tools intersected. I couldn’t stop shooting. At the time I was more interested in starting small things and growing them slowly. I saw how some other email newsletters, such as Daily Candy, had been able to monetise through advertising. I figured if I wrote something specifically tailored to digital photography as a newsletter and got a few thousand subscribers, I could do the same.

Initially I just told my friends about it, so I could work out the kinks, but they told their friends, and they told their friends, and it started to build up momentum. I wrote photography tutorials and tips that I know certain blogs would want to write about — like showing people how to print edible photos onto cupcake frosting, then reaching out to cooking and entertaining blogs. This is how I grew the audience piece by piece.

As you said, Photojojo was just a mailing list at that point. There was no store or any way to sell photography-related things directly to my subscribers. A few months after launch I found a simple photo hanging solution called a ‘photo rope’. Inexpensive and casual, it seemed the perfect antidote to frames for people who couldn’t be bothered to spend a lot of time decorating. The only problem: it wasn’t available in the US. As an experiment, I imported a bunch of them, created a Paypal button, and started selling them.

It was so exciting when those first orders started coming in. People on the Internet were giving me money — for physical objects! I recruited my roommate Sahadeva Hammari to help me pack up orders and we’d wheel them to the 24-hour post office in the middle of the night. I kept writing and sending newsletters, kept adding more unique photography accessories and tools I’d find all over the world, and kept experimenting. And sales kept growing.

Approaching Christmas that first year things got a little insane. I couldn’t fit all the inventory in our Manhattan apartment, so we moved everything to my parents’ house in Connecticut. They very understandingly gave up their living room to yet another one of my ‘projects’. This time I recruited my mom as well, and she, Saha, and I would pack up boxes all day, stack them in her minivan, and drive them to the post office the next morning. Then we’d start all over again. It was back-breaking, exhausting work. We made tonnes of mistakes, but learned much more.

[Offscreen] I vividly remember visiting Photojojo the first time because it was scattered with jokes and puns. There were unicorns and rainbows, and a ‘Do Not Pull’ lever next to the price tag. It looked like the guys behind that site didn’t take themselves too seriously.

People love that ‘Do Not Pull’ lever! I think it’s being pulled a million times every year now. We’ve tested it — because we test everything obsessively — and it actually lifts conversions, too.

But for us it’s all about being human and treating people like we ourselves would want to be treated. That principle forms the bedrock of our (internal) customer service manifesto, and it’s core to who we are. When you visit our site, we consider it our job not just to show you some great photo stuff you didn’t know existed, but also to make sure you leave with a smile on your face.

We do that with our writing, which is friendly and playful, and with Easter eggs hidden throughout the site: scroll to the bottom of our homepage and a photo dinosaur pops up and takes your photo. We also do it with jokes in our emails, like our own take on the run-of-the-mill order tracking page: your order is traced from our warehouse to your home on an animated, tattered parchment treasure map, complete with mythical monsters! Recently, we even launched a ‘secret’ store hidden in our checkout flow. For a dollar or two, you can add things like pizza-scented soap, or the scent of freshly-baked cookies to your order.

Why? Why not? It’s fun. In the biography of Ben & Jerry (the ice cream guys), Jerry says, “If it’s not fun, why do it?” and that really stuck with me. Our time is incredibly limited and precious, and we spend so much of it on our work. If it doesn’t give us joy, and doesn’t bring joy to others, then why do it?

With large, generic stores taking up more and more of consumer spending, there’s tremendous value in having a point of view.

[Offscreen] Looking at Photojojo’s success, what major lessons did you learn that can or cannot be applied to other businesses trying to sell things online?

Ecommerce is hard. It’s harder than it was ten years ago, or even five years ago, and Amazon is a beast that even has companies like Walmart shivering.

To be successful selling stuff online today you have to pick your audience and your niche incredibly well. Not only do you need to understand who you’ll serve and what they care about, but you need to live and breathe that stuff. I think we’ve thrived because we love photography like no one else. It comes out of our pores. And when you visit our site, ask us for help, or see how we use the products behind the scenes, it’s obvious.

With large, generic stores taking up more and more of consumer spending, there’s tremendous value in having a point of view. My theory going into this was that people want to buy from someone who cares about the things they care about, someone who’s like them. It’s been gratifying to see that theory validated as our fan base grows.

I believe we can continue to grow as a friendly ‘neighbourhood’ photo store that just happens to be online, and I think that the Internet has plenty of room for others like us in a variety of verticals. I’ve certainly toyed with the idea of starting a sister brand many times.

[Offscreen] It’s interesting to think that before the iPhone came about, most of the products you sell didn’t even exist. If we’re now in the age of mobile photography, where are we heading next?

The past four years have seen us make a drastic change in our product lineup. When we started, we were all about digital photography, be it SLR or point-and-shoot. And that already was a new thing at the time! Photojojo has always been about experimenting with the new, because that’s what we’re most interested in.

And yes, we’re definitely in the age of mobile photography! A high-resolution, pretty-damn-good camera in every pocket. And a video camera, to boot. That’s a renaissance. That’s a level of access that’s never existed before for this art form. And it’s the biggest thing that’s going to happen to photography for quite a while. We’re still seeing the aftermath.

The photo has become a medium of expression on equal standing with words. Our primary use of photos today, for most people, is not to create a work of art, or document something for posterity, it’s simply to communicate — whether through Facebook, or Snapchat, or WhatsApp — the photo has become a quick, core building block of how we talk to each other. And it’s not just personal communication. Think about the last long-form article you read online. Chances are, it had a large header image, embedded image slider, or full-screen images throughout.

The accessibility of photography and video, combined with the opportunities provided by the screen as a medium, are very literally changing how we communicate. In the coming decades, we’ll use words far less, and photos and video — as interactive content — will take over.

[Offscreen] Sounds like the future is looking bright for Photojojo! But in late 2011 none of that seemed to matter anymore, as you were forced to face your own mortality…

In late September of 2011, I came down with a fever. I became weak and stayed home for a few days, took cold medicine, drank plenty of fluids. But I didn’t get better. I made my way to a doctor and got checked out. He thought I might have mono, so he did a blood test and told me to get plenty of rest. The next evening I got a phone call. It was him, and he got right to it: “The results of your blood test came in. You have leukemia. Your white blood cell count is extremely high. You need to get to the hospital right now.”

While he made arrangements, I packed a backpack and googled ‘leukemia prognosis’ and ‘leukemia odds’. I spent that night getting antibiotics and blood transfusions at a San Francisco hospital. The next morning, with a face mask to protect me from germs, I boarded the first flight to New York. There was no time to say goodbye to friends or Photojojo. I was admitted as soon as I arrived in New York and spent the next several months imprisoned in a hospital room at Yale-New Haven Hospital getting intensive chemotherapy to fight back my Acute Myeloid Leukemia.

It’s hard to understand or even believe it when something like that happens to you. I cried, I felt sorry for myself. I wrote a painful email to my friends and co-workers explaining what had happened and that I wouldn’t be back for a long time. I called Jen, my protege at Photojojo, and told her that I needed her to take charge, to hold things together. I would suffer incredibly over the next year and would discover my limits in many ways.

So yes, the Internet very literally saved my life.

[Offscreen] I didn’t know you back then, neither did I follow you online, but I remember coming across several donor drives and online campaigns calling for help. Is it fair to say that the Internet saved your life?

My friends and family are truly amazing. I needed a matching stem cell donor to survive. With a donor, the odds were scary, but without a donor, the odds were grim. Unfortunately, they had no matches in the National Marrow Donor Registry, so my friends began to hustle and organise.

First, a registry drive on the east coast, then another one on the west coast. My Daily Jolt co-founder started coordinating drives in India, where the odds of finding a match were higher, but we had to bear the costs at $50–$100 per test. So another friend started fundraising to help pay those costs. My parents and other friends helped orchestrate drives at Indian temples and college campuses around the US. Then even more friends started coordinating press requests, and made websites to increase our reach. Seth Godin pledged $10,000 to the first person to match and donate, Jake Lodwick and Michael Galpert followed suit. I did interviews on NPR, a live Skype interview on CNN with their top medical correspondent Sanjay Gupta, and online interviews with every major tech blog. TV actors Aziz Ansari and Chris Pratt made informational videos about the disease and how to help. Pretty much everyone I knew through every project I’d ever worked on volunteered at drives and helped spread the word. It went on and on!

Over the course of three months, we held hundreds of drives. Friends started Twitter, Facebook, and Tumblr campaigns to spread the word. These posts got thousands, then tens of thousands of reblogs. One day, one of my attending doctors came in on rounds and told me that a college friend of his had sent him a Facebook message asking him to enter the bone marrow registry for me. We actually brought down the National Bone Marrow Registry’s website by sending them more traffic than they’d ever had!

Several months later, we finally found a donor through one of these drives. So yes, the Internet very literally saved my life.

To this day, I still hear from people who registered at a drive to help me, then later got the call to donate for someone else in need. Knowing that we were able to save not only my life, but so many others, is an incredible feeling.

[Offscreen] How is your health today?

I’m doing well, but it’s a very long path to recovery. Treatment required six months in and out of hospitals. The recovery back to ‘new normal’ takes one to two years.

I don’t think I’ll ever get back to where I was — your body gets chemically and physically beaten in the process of treatment for cancer — but I feel good now, I’ve worked hard to get my energy back, and I’m happy with where I am.

[Offscreen] Your experience must have changed your perspective on… everything. As a result of your illness, how have you reshuffled your priorities in life?

When I arrived at the hospital, it was unlikely I’d survive. I felt sorry for myself. I made lists of all the things I’d do if I ever got out. Sure, I had led an interesting life, but I had made sacrifices in the present for a payoff in the future, as we all do. Now I saw the cost of those sacrifices when there is no future.

I also realised that I had made no backup plan for Photojojo. I was still writing work-related emails and taking conference calls from my hospital bed while getting poison pumped into my veins. I hadn’t taken an actual vacation, ever. With no investors and as a solo founder, what would happen to it if I didn’t make it? I hastily executed a power of attorney and gave my mom instructions for what to do just in case. I promised myself I’d do better if I had a second chance.

When I started to get back on my feet I began knocking some of the items off my list: I lived in New York City again for a summer, I adopted my first puppy, I learned to motorcycle and rode across the country. And then I went back to Photojojo. For the last two years my most important task has been finding Photojojo a new home and a way to live on without me. After talking to many people and considering a lot of possibilities, I sold the company. I’ve been transitioning my role and responsibilities to Jen since I got back to San Francisco, and officially handed over the reins to her late last year. It’s strange to step away from something I’ve spent so much of my life building, but I’m excited for what the future will bring, for Photojojo and for me.

Being forced to realise that your life will soon end, quickly changes what you deem worthy of your attention. I stopped wasting time on Twitter. I stopped idly reading websites when I didn’t have anything better to do. I was angry at myself for having wasted so many minutes, hours, and days on meaningless consumption. Furious! It’s hard to gain this kind of perspective, and it’s equally hard not to lose it, not to start slipping back into old habits.

Partially for that reason, I’m leaving San Francisco. I love the city, and I can’t say I won’t be back, but it’s a siren that lures me back into my old life — a comfortable life for sure, but not the one I want to live now.

I plan to wander for a while; to take a sabbatical. To spend three months at a time in different cities. I have ideas every day for new projects and companies I’d like to work on, but I’m writing them all down. In three to six months, or maybe longer, I’ll come back to them and see what still excites me, see what common patterns emerge and what I’m drawn to over and over.

And in the meantime, my job is to remind myself every day that my time is limited. And so is yours.



First published in January 2015 in Offscreen Magazine No10. 
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Questions by Kai Brach, photos by Helena Price.

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