Interview: Amit Gupta

On Founding Three Startups, Being Saved by the Internet, and Saying No to VC

Amit Gupta is a serial entrepreneur and founder who has helped shape the trajectory of technology and creative communities through multiple ventures. Born to Indian immigrant parents in Connecticut, Gupta's entrepreneurial journey began during his college years at Amherst, where at age 19 he dropped out to run his first startup, The Daily Jolt, during the dot-com boom of the late 1990s. This early experience—which included having to lay off staff during the market downturn—would prove formative in shaping his future approach to building companies.

In 2006, Gupta founded Photojojo, a pioneering photography brand that began as an email newsletter and evolved into a successful e-commerce business known for its distinctive personality and design aesthetic. The company stood out in Silicon Valley for its strong brand identity at a time when most tech startups focused primarily on engineering. Under his leadership, Photojojo grew to encompass a book deal, TV appearances, large-scale events, and its own line of camera and phone accessories.

In 2011, Gupta's life took a dramatic turn when he was diagnosed with acute myeloid leukemia and given just days to live without treatment. His search for a stem cell donor became a remarkable story of community mobilization, with hundreds of drives organized across the country and support from celebrities and media outlets. The campaign successfully found two matching donors, and Gupta underwent a successful stem cell transplant that saved his life.

This experience profoundly changed his approach to both life and business. After recovering, Gupta sold Photojojo and embarked on a series of personal adventures, including learning to ride a motorcycle and traveling across the country with his dog in a motorcycle sidecar.

Today, Gupta is the co-founder of Sudowrite, an AI writing tool for authors. Unlike his previous ventures, Sudowrite reflects a more balanced approach to entrepreneurship, intentionally structured to maintain work-life equilibrium. The company raised $3 million from individual investors including founders of Twitter, Medium, Gumroad, and Rotten Tomatoes, along with writers and directors. Under Gupta's leadership, Sudowrite has chosen a path focused on sustainable growth and profitability rather than traditional venture scaling.

---

Amit! How are you doing?

It's been a while.

I know, I know.

I want to start this one a little differently and first acknowledge how I met you. I don't even know if you remember, but it’s interesting because it was so random and now here we are, more than 15 years later.

It was while I was on vacation in San Francisco in 2007.

I didn't know that.

Yeah, well before I even knew I would live here. I just kind of ended up meeting your friend group on vacation, and I was invited to your house for that miracle berry party. Do you remember that?

Okay. Yeah.

Without context, that sounds very sketchy. But for the reader—it's just a berry, but if you eat it, it turns off the sour taste receptors in your mouth. And so I went to your house for this miracle berry party, which was basically a bunch of us sitting around a dinner table full of plates of sour food that tasted different because our sour receptors were off. That was it. We just sat around and ate sour food for several hours.

And I remember thinking, “If this is what San Francisco's like, I feel like these people seem kind of strange and awesome and fun. And I'm coming from North Carolina, which isn’t anything like this.” It made me think, “Maybe this is where I want to live.” So you actually played a meaningful role in my coming here.

I'm so happy to hear that.

Yeah. Very grateful for that. Your company at the time, Photojojo, also eventually played a role in my life. But first, I'd like to step back to the beginning for just a minute. I don't know anything about your early life or where you come from.

Yeah, so I grew up in Connecticut. My parents came from India. My dad moved here after finishing medical school, and then he went back to India to visit his parents. What happened next is like family legend. He went into a room with my grandfather, and nobody knows exactly what was said in that room, but when my dad came out he was in tears. It turns out, he’d been told he had to get married before he could go back to the U.S. They had already pre-selected three candidates for him, and he met them and chose my mom.

They got married just like that, all within a week, and then he flew back to the States. My mom had to stay behind in India because she didn't have a visa. She joined him months later. She's told me about how she wasn’t sure she would know what he looked like, because, you know, she’d just met him, gotten married, and then he’d left so quickly. It was a blur. And then away she went, never having been on a plane before, never left the country, barely spoke English, leaving everything and everyone behind.

When she finally landed in New York it was winter, and she was just shocked by how cold it was, like, “Oh my god, what planet is this?”. My dad was in his residency, pulling 20-hour shifts, would be gone for days at a time. He often had to sleep at the hospital, and she was at home with no one to talk to. Long-distance calls were a luxury, exorbitantly expensive, and in India, you couldn't even receive them at home; you had to go to a special place to make or receive a call. So she was completely disconnected, didn’t know anyone, didn’t know how to get around, couldn’t drive or speak the language.

It’s my parents’ story I’m telling, but it feels like a part of my story too. Their lives were more difficult than mine will ever be. Compared to them, I grew up in this cushy life in America where there’s infinite opportunity. Infinite! And yes, America isn’t perfect, there’s bigotry and racism and economic disparity, but compared to what my parents went through, my childhood was pretty much perfect. They did everything to give my brother and me a good life, investing in our education and supporting us all the way. So, yeah, that's the story of my childhood and how my parents made it as perfect as anyone could.

Wow. And they're still together.

They're happily together. In Indian culture, PDA isn’t really a thing, or at least it wasn’t back then. People don’t usually go around saying “I love you”, though maybe that's changing now. I think they're totally interdependent, supporting each other in so many ways. Over time, they've really become this beautiful team. And I think that's love, even if I can't really recall ever hearing them say “I love you” to each other.

You say that you know now how amazing your childhood was, and you have that perspective of comparing it to your parents. Did you know that as a kid?

I felt so entitled as a kid. I would think, "Man, I hate my parents. They're not like everyone else's parents. Why can't I have ham sandwiches? Why can’t I ever have Big Macs? Why can't I eat meat? Why does my house smell different than my friends'?" All those things that immigrant kids worry about and then feel guilty for later on when they grow up. But back then, I really didn't love it. I didn't even like going to India, which is funny because now it's one of my favorite places. But as a kid, we'd go in the summer, and it was just ungodly hot, full of mosquitoes, and no air conditioning. I couldn’t wait to come home. But then we’d come back and I'd bawl my eyes out because I missed all my cousins, uncles, and aunts.

When I met you, you were in San Francisco. That's very far from Connecticut. Did you want to get away?

No, I don't think so. By then, I wasn't trying to run away anymore. In fact, during college, I started a company and even dropped out for a couple of years to focus on it, around 1999. That whole two-year period was really eye-opening in many ways. One of the pivotal moments was towards the end of my time with the business, I went to India for about six months to work and experience something different. I spent a lot of that time with my mom's side of the family, and it really helped me understand and appreciate her on a deeper level. When I came back, my perspective on my family had changed significantly.

My move to San Francisco was about my career. I saw all this interesting stuff happening with technology, and I had been living in New York, starting conferences and events to bring tech people together, but it wasn't anything like San Francisco, which was the center of it all. I visited San Francisco a few times – consulted for Apple, attended a friend’s conference – and it was just so clear that I needed to be there, so I moved.

So you had a startup in college. Can you tell me about that?

Yeah, during the go-go '90s, think Yahoo, Excite, and all those search engines battling it out. The internet was brand new, and I was in college, and so excited about computers. So, my roommate and I started this little project. It was essentially a start page for college students at our campus because college websites kind of sucked back then. Our site had everything a student at Amherst College might need daily, and soon we began expanding to other campuses. After a summer working on it, I decided to drop out of school, which surprisingly got my parents' support. They're Indian, dropping out is like heresy.

I was 19 when we raised angel money. Our team grew to about 27 people, and I was the youngest person there. We were living the typical startup life; we had bunk beds in the office. I slept there a lot of the time and just worked nonstop for two years. Then, the dot-com bubble burst. The company had expanded to 100 campuses, but we struggled to raise money. I had to lay off half the company, then lay off half the company again. I was this 19-year-old, sitting down at a Starbucks with people much older and way more experienced than I was, explaining why we didn’t have enough money to employ them anymore. It was terrifying.

I eventually got the company to break even, but I was burnt out and ready to go back to school. My co-founder had left a year before, so I put someone else in charge, went to India for six months, then went back and finished college.

Wow. That's a lot to experience at 19. Looking back, were you like, thank God I was just young and naive, uh, and didn't understand the sense of responsibility I had. Or did you really feel the heaviness of that?

Oh, it was tough, definitely the hardest thing I'd had to do up to that point in my life. Laying someone off is never easy. Letting anyone go is one of the most challenging things you face as a founder. And at 19 without any support system or anyone I could really turn to for advice on how to handle these situations it was even harder. I mean, I had to fire the CEO I’d hired–obviously, I couldn't ask him for guidance. I had to lay off people twice my age. So yeah, it was rough, but I learned a lot from the experience.

What do you think helped you get through that time? I'm asking because I know there's a bunch of people that are about to go through this for the first time. It's happening to a lot of founders right now.

I remember the sheer panic that we had to lay people off and there was no one else to do it but me. I didn't have any guidance. It would be a lot different today. My views on employment have changed a lot over the last two decades. If you'd asked me, “does it make sense to be an employee?” back then I would have said no, you should always just be a founder. Why would you ever work for somebody else? That was a very self-centered point of view, because I never wanted to work for someone else, so I couldn't imagine why anyone else would.

Back then, letting someone go felt so life or death. I thought I was ruining people's lives, that they’d hate me forever. Of course, that's not true. Being laid off or firing someone is traumatic. It’s really painful. But it's also a part of life. People get fired and laid off and they find new jobs.

I'd say in most cases, long-term, it's a good thing. If it’s not working out, they probably don't feel good about it either. And they're not going to succeed in this company if they're not a good fit. And if they're let go, they can go somewhere else and find something that's a truly wonderful fit for them. But that moment of transition is always still really painful and difficult. At least knowing that the future is better makes it a tiny bit easier for me if not for them.

Are you historically a people pleaser?

Oh yeah, I don’t know if you’re into Enneagrams–it’s kind of like business horoscopes. Back then, I was definitely a strong nine, all about avoiding conflict and building harmony. Now, I’m a seven, seeking excitement and adventure, but there's still a lot of that nine in me.

Funny—I had someone tell me recently that your Enneagram type can't change. I thought, well, they obviously haven't met me. I mean, if you've changed your wiring or values as a person, why couldn't your Enneagram change?

Thinking about layoffs, that was probably the first time in my life where I couldn't let my actions be driven by a desire to please everyone. It was a moment of realization for me, like, "Oh, man, there's no way to make everyone happy here."

And honestly, going through that was good for me. It forced me to face the fact that whatever I did, the person on the other end wasn't going to be happy with me. So then I had to come up with a new system that wasn’t about pleasing people. I had to ask myself, "What are my values, and how can I approach this situation in a way that aligns with those values?" That was a major turning point in how I made decisions.

Yeah, I heard a founder talking about this idea they had, or maybe they were already doing it, about letting employees sign an optional contract when they start. The contract would say that in exchange for getting real, honest feedback should they ever be let go, they agree not to hold it against the company. I found that intriguing because one of the saddest parts about having to let someone go is that you can't share feedback if they ask for it, because legally, it's too risky. Not everyone wants to hear feedback in that moment, but some people genuinely do, and it could be a real growth opportunity.

That is true.

So eventually you ended up in San Francisco. When I met you, you had Photojojo, and I believe it was already quite successful when I met you, eating miracle berries on vacation. What's the story with Photojojo? How did you start it?

It started in 2006 when I was living in New York. I had come to New York to help Seth Godin start a nonprofit called ChangeThis. I had always been into photography, I did it a lot in high school and dabbled in college. I got back into it because New York’s such a photogenic city. It’s hard to live there and not want to be taking photos constantly. I got into photo blogging, got into the photography community, and decided I wanted to do something in the space.

I started playing around with ideas, and eventually, I came up with the concept of a simple email newsletter focusing on tips and tutorials, aimed at making photography more fun. At the time, most photography media was gear reviews, quite technical and serious—think black backgrounds with white text. I wanted to create something more approachable and friendly. That was Photojojo. It started as just a free email newsletter. I didn’t do any promotion, people just told their friends and it grew.

That first year, I saw an opportunity to sell a product I’d seen in Europe that wasn’t available here in the States. I figured out how to import it and started selling it, packing boxes right from our kitchen table in our tiny Manhattan apartment, making runs to the 24-hour post office at 2 am, figuring it all out as I went. I did that for months and the email newsletter evolved into an ecommerce business. After moving to San Francisco, I hired our first full-time employee to work on the newsletter.

We went on to get a book deal, made TV appearances, hosted massive events, and designed and manufactured our own line of camera and phone accessories. But through it all, the core mission was always about helping people have more fun with photography.

It just occurred to me how ahead of your time you were as a brand in Silicon Valley. It was 2007 when I first saw your company. And Photojojo was a BRAND. It had a robust visual identity, and a personality, a voice—it was very sophisticated for its time. Totally different than all of the other startups, which were very engineering-MVP-focused and visual design wasn’t even really a thing yet. Do you think New York was an influence on that?

Yeah, thanks! Growing up, I was totally obsessed with Apple and Steve Jobs, Ben & Jerry, Disney, Ricard Branson. It was clear to me early on that I wanted to create a brand where the personality and vibe mattered. And you're right about New York. New York had Vimeo and Etsy, which were imbued with this amazing art and spirit, San Francisco had YouTube. YouTube was more like an empty vessel for videos, while Vimeo was art itself.

Today, Vimeo has evolved to resemble YouTube more closely, but with a slightly nicer interface. But I think that New York startups are still a different breed, they care more about branding, vibe, and voice.

So all of this happened. Photojojo became quite large and successful.

I want to take a turn to the dark side for a minute because during this time, you got very sick. Can you talk about that?

In 2011, while running Photojojo and starting a second brand with my friend Diana Berlin, I started feeling incredibly worn down. One day, I felt out of breath just going up stairs. I stayed home from work for a few days, which was unusual for me, and I just wasn’t getting better. I went to see my doctor, and the next day, I got a phone call from him, and he said I had leukemia. He was like, go to the hospital right now, otherwise you’ll be dead in a week.

So, I crammed a bunch of clothes into my backpack and headed to the closest hospital and they started giving me transfusions and antibiotics. I caught the first flight to the East Coast the next morning to be near my family, going straight from the airport to Yale’s Cancer Center. I hadn't even had the time to tell my roommates or friends or Photojojo employees about what was happening. I just up and left.

Once in the hospital, I pretty much ran through every stage of grief—denial, bargaining, etc. They told me I had acute myeloid leukemia, which is very aggressive. The only potential cure was a stem cell transplant, but they had to find a precise match. Barring that, I could get a lot of chemo and maybe make it another few years. With a perfectly matching stem cell transplant, my odds were better: 50-50 for making it through five years.

I didn't have a match. There's a national bone marrow registry, where people sign up to possibly be a match for someone in need. But it’s very hard for a non-white person to get a match.

So I was in the hospital for a month, getting a ton of chemo to beat back the cancer. At the same time, I was trying to run the company from my hospital bed—taking conference calls, doing press interviews, and, well, dying, which, you know, takes up quite a bit of your time. And then, my friends—they started to rally together. People had heard about my situation and wanted to help out, so they started donor drives to find a matching stem cell donor, since it was the best shot I had. This was the one thing that could potentially give me life. But the doctors, they were kind of like, “Sure, it’s a good thing to try, but don’t expect it to work.” The odds were just so slim, like one in ten thousand people would match me. And there was this tight window to find a match—we had about a month because of the processing time before we needed to start the treatment for it to have a chance of being effective.

So, I figured, "Let's just try." My hospital room turned into a war room. Every day, my friends were holding daily stand-ups, brainstorming ways to spread the word, encourage more donor sign-ups, get them to host trials, organize swabbing events. Some of my friends took time away from their jobs to help. We organized hundreds of drives across the country—on college campuses, corporate offices, and even temples. We organized drives in India, raising funds for those efforts. We did a ton of press, and Seth Godin, helped out a lot with PR. Professor Aaker at Stanford got students there involved, Porter Gale, VP of marketing at Virgin America helped. We had celebrities like Chris Pratt and Aziz Ansari doing PSAs, it kept getting bigger and bigger, and I was interviewed on NPR, CNN, NBC news, etc. and all this time I’m just getting sicker and sicker.

Amazingly, we did find a matching donor. We found not just one, but two matching donors, which was pretty fantastic. And then I had the transplant.

So, now it's about 3 or 4 months into this whole ordeal, and I've been through numerous rounds of chemo, and they were harsh. My parents are beyond stressed, especially my mom, who's constantly crying because she thinks I’m going to die. The chemo you get right before the transplant is basically the maximum dose they can give a human being without killing them. The goal is to eradicate every last cancer cell in preparation for the new stem cells. This process completely destroys your bone marrow, which is what creates your white blood cells, your red blood cells, your platelets. So if the transplant doesn’t work, then your body can’t make blood anymore. You kind of need blood.

So, I get the chemo, and the stem cells arrive. It’s this small bag of what looks like yellow pus, and they start dripping into me. Very anticlimactic. Then, for the next 2 or 3 weeks, it's a cycle of constant blood tests and transfusions while we wait to see if my body will be able to make blood again. These stem cells have to make their way through my body, into the marrow in my spine, and start making blood.

And miraculously, it works. It feels like science fiction that we can do this. My new blood is a different DNA than the rest of my body. For the first year post-transplant, I’m on immunosuppressants to stop my new immune system from killing me since it sees my organs as foreign bodies. I’m a chimera now. There are even stories of people with transplants leaving blood at a crime scene, and the DNA leads back to the donor, not the person who was actually there. It’s wild, really. I’m walking around with two sets of human DNA in me.

But it saved my life. The next year was really tough. I was dealing with constant fatigue and getting sick all the time. Eventually, I started making my way back to San Francisco. While I was in the hospital and didn’t think I'd survive, I had made a list of all these things I wished I'd done. I'd lived a pretty full life, traveled, started my own company, had a blast. But when you realize you’re not going to get any more time, you realize there's a lot more that you wish you'd done. So, now that I had a second chance, I had all these things I wanted to do. I learned to ride a motorcycle. I got my first dog, and took her across the country in a motorcycle sidecar. When I got back to San Francisco, I realized I needed to sell Photojojo, because I still had those 50-50 odds of making it five years hanging over my head, and I knew if I ended up back in the hospital without having done these things, I'd be really pissed at myself.

The next question I was going to ask you was… how you did all this while keeping a company alive.

I mean I had a great team, and without them, none of this would have been possible. They really pulled together, and did everything they could to keep things moving forward. And they had to, because I didn’t have a co-founder, and being a bootstrapped company, there were no VCs to swoop in and put in someone new. Everyone stepped up. So I was working hard, but I couldn’t have done it without all of them. After the transplant, they had to continue to carry a lot of the weight, because I was just a broken human being, I struggled to concentrate, to think clearly for hours at a time. It took a while before I could even function at half my usual capacity.

I realized then that I needed to sell the company. I wanted to find the right owner, because this company felt like me, like an extension of who I am, like my child. I couldn’t bear the thought of it not being cared for properly. I spent about a year, maybe a year and a half, getting the company ready, covering roles and tasks I typically handled myself, and then looking for a buyer. And that was hard. There’s a saying that companies aren't sold; they’re bought. Someone comes to you with interest, and then you leverage that interest to attract other bids. But I didn’t have time for that, my clock was ticking.

So, I essentially spent months on the phone, reaching out to anyone I thought might have a connection or could lead me to someone interested. I’d share why I was selling, tell them my story, and then ask, “Who else should I be talking to?” Each call would branch out to two or three more. I’d be on call after call until about 1 or 2 in the afternoon, by which point I was just completely drained and couldn’t even sit up anymore. I’d go home and just crash.

Eventually, through all these calls, I found someone who was interested. Then, suddenly, there were several interested parties, and I ended up selling to one of them. I negotiated a deal that allowed me to leave the company after a really short period—about six months—which meant taking a significant cut in the payout, but that was a trade-off I needed to make.

After the sale, I tried my best to not think about Photojojo for the next year or two, which was hard, but it gradually became easier to let go.

Yeah. I mean, hearing you say you had that same relationship with the brand that I felt like I had with Haus. And then having to say goodbye to it. What was the mourning process for you like?

Yeah, I remember the day I got emails saying that the due diligence was finally complete and we were ready to sign off. I was sitting on my bed, staring at the emails, and I realized after all that work, I wasn’t sure I wanted to go through with it. Luckily, I’d hired a banker, and he was ready for that uncertainty—it's probably something many founders face at that moment. He talked me through it, but yeah, it was really hard. That company was a huge part of who I was, of my identity.

Leaving San Francisco helped a lot with unwinding that identity. I wanted to travel and experience all these new things. If I’d stayed in SF it would’ve been really difficult. Even after stepping away, I found myself still engaged, attending board meetings and staying involved in ways I didn't need to. I just couldn’t help it.

A year later, Photojojo looked very different—it became venture-funded, the new owners threw a lot of money at it, moved to fancier offices, and hired rapidly. Within a year, it just felt like an entirely different company, which made it easier for me to separate from it.

Yeah, that makes sense.

It's so different from now. I had a health scare a couple of weeks ago. I was dealing with a rotator cuff issue, and when they did an MRI, they found something weird in the bone marrow of my arm, so the doctors wanted a bone scan immediately, hinting they were concerned the leukemia might have returned or that something else was wrong. I was scared. I remember thinking I would quit the company I’m working on right away—very different from my reaction when I got sick while with Photojojo.

I've been reflecting on why my reaction to this was so different. I think there are a bunch of reasons.

One reason is that I was very intentional when I started Sudowrite, that I didn't want it to be the same type of relationship that I had with Photojojo. I always care deeply about my work, probably too much, but with Photojojo, it felt like way too much. After selling Photojojo, I hadn't planned on starting another company. I thought I was done with that chapter of my life, I was focused on writing. So, when Sudowrite came into being, I decided it would be just a part of my life, not consume it. I believe I've been somewhat successful in maintaining that separation, because during that temporary health scare, I did feel like, “Okay, I can walk away.”

The other piece was that I have a co-founder this time around. James is not just amazing as a co-founder, but he’s also one of my favorite people in the world. He even introduced me to my wife. With him, I know that everything would be fine without me.

You’ve already touched on this a bit, but how did all of these experiences change you, and ultimately change the way that you wanted to approach this new company?

There was this moment when I first got leukemia and was in the hospital in New Haven. I wanted to email people to tell them what was happening. My instinct was to alphabetize all the email addresses, you know, to make sure no one felt like an afterthought, which is something I would do back then. But suddenly, I had this flash, like, “Fuck that. I’m not doing this." I decided to just write down names as they came to me, in whatever order that was. It felt like such a big deal at that moment for some reason.

When you go through something that traumatic, it changes you. There's some level of unlearning that happens. This is my experience. Whether or not you intend for that, it just starts happening. It's a little scary. You change, and that's not only going to impact you as a human and how you interface with the world, but it will inevitably impact how you start a company the next time around.

I agree. Because of the experiences I’ve had, with psychedelics, with almost dying, I’ve learned a lot about myself and how I view work. One of the biggest takeaways was that all of life, including work, is a game. Work is a game you can choose to play. You can be really good at it, you can take it super seriously, you can have fun with it, but no matter what, it's just a game.

Despite running a company all about having fun, I used to take everything so seriously, everything seemed super high stakes. It doesn’t always feel that way anymore. Sure, it's easy to slip back into old patterns, but for the most part, I can hold that thought that it's just a game. If I lose the game, that's okay. I can play other games or I can restart this game. Life will go on; that was a big learning.

We were at a company retreat a few weeks ago, just the seven of us. While hanging out in a hot tub, Josh asked me what I was looking forward to for Sudowrite next year. We've gone through all these planning exercises and stuff for the past few days. I mumbled something about how I was excited to return to the level of growth we were seeing in early 2023. Josh gave his take, something about engineering challenges, and then it was Ginny’s turn. She talked about how she felt honored to work with writers, and to be here in this moment in time where she got to influence how people were going to tell their stories in the future—it was really inspiring. And I remember thinking, "Oh man, that’s what I should’ve said.” I realized I had gotten caught up in the game again, focusing on growth and operations instead of the real reason I’m doing this. I slip in and out of it all the time, but it’s something I want to hold onto more, but man, it's hard.

After I got back to San Francisco, post-Photojojo and leukemia and stem cell transplant, I went to see a life coach. I was trying to figure out what to do next with my life. The life coach asked me: "What would you do if you only had one day to live?" And I shared this elaborate plan about renting a private jet and spending it with family and friends, all this stuff. Then they asked, "What about two days?" and I adjusted my answer accordingly.

But the thing is, that just doesn’t scale to an indeterminate amount of time. It doesn’t apply the same way if you’re looking at 20 years or any unknown span of life ahead of you. I remember feeling so frustrated by that realization. It’s like, if you know you're playing the game for just a day, you know how to play that game. If you know it’s a game for a lifetime, you know how to play that. But when you don't know which it is, which is the truth for all of us, it becomes much harder to play in a rational way.

I was recently having some existential thoughts, trying to figure out my life. I was going through thought exercises like… "What would I do if there was a comet heading to Earth right now? What would I choose to be doing with my life?”

And then I go on Netflix and I see that there's a new show about this exact thing. About a comet hitting the Earth, and that everybody has seven and a half months before impact to do whatever they want. That’s the backdrop of the show—most people are like—half of them are walking around naked. Everybody's sky diving, like, it's kind of just chaos.

Anyway. You've actually had this near-death, months-left-to-live experience. You lived it, and in a way, continue to live it. And with your time right now, you’re building your third startup. I want to know how all of this impacts your strategy as a founder this time around. I know you didn’t take VC, for instance, when you could.

I dropped out of college at 19 to start my first company, The Daily Jolt—I actually started the company in college, then dropped out to raise money for it. That was a venture scale business. After that, I started Photojojo, where I bootstrapped and never intended to raise money or exit, and now I'm working on Sudowrite, which is kind of in between.

All of these approaches can work. James and I took a different approach with Sudowrite because we had both had successful exits already and neither of us was planning to start a company. I was writing science fiction and surfing three times a week, enjoying my freedom and flexibility. James was also writing and enjoying being a dad to his two young kids.

So when we started working on Sudowrite, it was a side project. And that's how it stayed for the whole first year. But as we got to the end of that first year, we were writing fiction less and less and working on the “side project” all the time. But we didn't have the resources of a company, so we were doing everything ourselves. It felt like we couldn't do it justice without bringing on more people, and that meant it needed to graduate to being a company.

So, we opted to raise money, but exclusively from individuals. We were upfront about our goals–to create a better product, and a self-sustaining, profitable business. Crazy, right? Dozens of friends invested, founders of Twitter, Medium, Gumroad, Rotten Tomatoes, and tons more, along with writers, directors, and screenwriters.

Neither of us was eager to ride the VC rollercoaster, reaching for unrealistic goals, burning tons of money chasing growth, and working to appease investors. We wanted to spend our time building this tool for writers that we believed was important and needed to exist.

I'm sure some of our investors might have thought, "Ha, yeah right. Once they're successful, they'll change their minds." And honestly, that possibility has crossed our minds, but we're still committed to this path.

Did you come up with a format and structure yourself, or did you talk to people and find that there is a certain way people are doing this? Is there a standard?

We used a SAFE (Simple Agreement for Future Equity) for our seed round, which means there our investors convert to equity if we do raise more or exit. That's one possible outcome. Another scenario is we never go through another funding round but we buy out our investors or pay dividends. We opted for the SAFE because it’s familiar and all our investors have used it before.

Interesting. Okay. Yeah, we used SAFEs for Haus, and my understanding is that if you don't raise a priced round, nothing will happen. Essentially they won't convert to equity. So you didn't amend it or anything? The plan is that you would amend it if needed?

Yeah, we really have no desire to screw anyone over. We're committed to taking care of the friends who invested in us. So, I think as long as the company performs well, we'll be able to find an outcome that makes sense and keeps everyone happy.

And I mean, it speaks to the trust that people have in you. And I also think it speaks to their assumption that you're going to change your mind and raise a round. (laughs)

Yeah, totally possible.

Have you found that you're alone in this, or are you finding people in your world that are making the same decision to not raise VC, who've done so before?

Yeah, definitely. I'm seeing a trend where people are starting companies that don't require a lot of capital and might not target billion-dollar markets out of necessity. And then there are those who are doing it by choice, often second or third-time founders who want to take a different path this time around. They're exploring more sustainable or personally fulfilling ways to build their companies.

I am curious about your decision to raise from a few dozen people—was it intentional that you wanted a lot of small investors versus a few larger ones?

Yeah, I think so. We raised $3 million, and our hope was that each investor would contribute enough to be engaged, to read our updates and respond when they can help, but not so much that they would feel compelled to try to exert control.

James and I both care deeply about others' opinions, especially those we respect. If we had just a few investors and they wanted us to run the company differently, it might have been hard for us to stick to our own vision and resist that external pressure. It was important for us to have the freedom to manage the company as we saw fit.

Our investors have been amazing! They’ve made introductions, offered advice in key moments, connected us with people we hired, and tons more. All of our investor experiences has been positive so far.

This all resonates with me and the way Haus had so many small investors. It was a lot of support and the pressure was distributed.

And it also made more room for interesting people. We've brought in novelists, directors, screenwriters whose names you'd recognize, Emmy winners. I don't think that would have been possible if we were limited to a few large checks. We wanted people we knew well and liked, or those who had some connection to what we were doing, and ideally both.

Did you find that it was a fast process? Did you raise it all at once or have you done rolling notes or anything like that?

It was really fast. I think we spent a month-ish raising. My memory's a little fuzzy, but this was in 2021. I think it got really frothy in 2022, 2023. So we timed it well.

And when you set that valuation, was that completely your choice? Did you find that it had to be a negotiation or anything?

We capped it at 20 million. We probably could have made it uncapped. I don't think anyone would have objected.

How did you decide on the fundraising amount? Did you decide on three, or was three what ended up happening?

We decided on two and three is what ended up happening.

And when you picked that number, obviously you didn't need that to get to launch. Were you hoping to buy several years of runway or was that the amount that you projected to profitability?

We had a few key people that we wanted to hire, mostly people to build, engineers and a designer. And so we had a sense of how much we would need to pay these people, and we wanted two or three years of runway.

Are you hiring differently than you would have with a past, VC-backed company? I know that headcount was historically a vanity metric for Silicon Valley and there seems to be a major cultural change happening with hiring, and spending in general. There's a virtuousness to frugality now.

Yeah, I mean, my last company, Photojojo, was bootstrapped, so I never experienced the vanity of having a lot of people, and I wasn’t flush with cash when I started it. I grew it profitably from the very beginning. James went through YC with his previous startup, Parse, and they were gunning for significant growth and eventually sold to Meta. For Sudowrite, we landed somewhere in the middle. We’ve spent more in the first year than I did at Photojojo since we have money in the bank, but our ramp-up was much slower than if we were gunning for a Series A. Today we’re well past the traditional metrics for hitting a Series A in terms of users, revenue. And we’re profitable.

At our current ARR, I think most VC-backed startups would probably have twice as many people. We’re doing things differently, not just because we want to stay profitable and avoid the exhaustion of the funding treadmill, but also because it's more enjoyable to have a smaller team. If you can hire great people who can wear many hats, you’ve got so much less B.S. to deal with than in a big org with management layers and tons of communication overhead.

But also, it’s just a different game. I can see how other people have fun building the empire and amassing headcount. I personally just prefer the energy when you’re 10, 20, or 30 people. Everyone knows each other well, and you can move fast.

How do these employees think about compensation? Are they coming from VC-backed companies? Do they care about equity in the same way? How have those conversations gone?

That's a good question. We have employees coming from small startups, VC-backed companies, and others from big tech, so the compensation needs to be competitive. We use PAVE as our benchmark.

For equity compensation, we borrowed ideas from Y Combinator and Buffer. We have a method that determines equity based on an employee’s role, how senior they are, and how much the company has been de-risked by the time they’re hired.

We typically present two offers to choose from: one with a higher salary and lower equity, and another with higher equity and lower salary.

Compared to other startups, we’re competitive on cash and likely offering more equity, considering we've remained relatively small. Given our revenue level and how much we've de-risked the business, other companies might offer half or a third as much equity as we do now, but staying small has allowed us to be more generous with equity. People coming from big tech might take a pay cut, but they get more equity and make the move for more interesting work and more responsibility.

Yeah, yeah. And I guess they're not getting diluted five times over, which is nice.

Yeah, totally. And last year, for the first time, we did a profit share, so that's another aspect of our compensation that's a little bit nontraditional.

Yeah. How does that work? How did you come up with that?

I always wanted to implement profit sharing at Photojojo, but for various reasons, we never got around to it. Sudowrite had a profitable year for the first time last year, and I wanted to experiment with it, so we just decided to go for it. I had some worries—what if we're not profitable next year, or what if we have more employees and the profit’s the same, but everyone gets less? How do we manage expectations?

We just tried to be as straightforward as possible. We told everyone that we were trying this new thing. It might not happen next year, or ever again, or it might be very different. It was an experiment.

At Photojojo, I’d read about how employee-owned businesses operate. Some local Bay Area businesses, like Cheeseboard, are run this way, and there are a bunch of co-ops too. In our case, we set aside 10% of our profit and distributed it among employees, adjusting shares based on the portion of the year they were with us.

The choice to distribute 10% was somewhat arbitrary, but felt right for how young we are as a company. It allowed us to reward our team while still having the flexibility to reinvesting most of the cash into the business.

Have you found that that has impacted employee culture at all, having that as a very clear monetary incentive?

I'm not sure it has, actually. We didn't introduce profit sharing with the expectation that it would make people work harder, but it was clear that people really appreciated it. It came as a surprise.

We present comp differently than others. Many companies, especially public ones, calculate total compensation by adding up the potential value of equity, cash, and other benefits. We haven't done that. We don’t estimate the future value of equity or add potential profit sharing into a total comp figure. Sometimes I wonder if by not presenting comp packages this way we’re underselling our offer. But keeping things straightforward and honest feels like the right approach for us.

Well, I can imagine. VC teaches us all to overpromise, right? To dream big and to present the biggest vision you can possibly present, knowing that the expectation is that most will fail, but you have to have a big vision. And there's just something so appealing to me about the opposite now. Overdelivering.

If you can.

It requires not over-promising, which can be hard to unlearn.

Yeah, for sure.

Another common conversation these days is the increasing availability of tools that make starting a business easier. These days, more people can build companies that operate at scale—ventures that might have required VC backing in the past. With all these new tools, starting a company has become more accessible. Considering your experiences, have you found any tools particularly helpful this time around?

Yeah, absolutely. It's interesting because these tools have become so embedded in our processes that it’s hard to even single them out. But if you look at any part of our company, we’re likely using AI in some capacity to make things easier and faster. For example, our customer support is handled by humans, but we realized we weren’t responding to chat as quickly as we’d like. So, we use AI to speed up our reply times now. That’s a clear example.

We also do a lot of customer research, which means spending thirty minutes to an hour with each person. It can be really fun, but it's still a big time commitment. During these sessions, we have an AI agent that transcribes the conversations. This allows me to go back later, highlight the most important parts, and easily turn them into clips to share with the team.

And it’s so integrated into our process that I hardly even think about it anymore. But if I were doing this manually, I’d be recording the calls or perhaps conducting research in person, setting up a camera, and later spending hours editing the video. Now, it takes just seconds to scan through the transcript, find the relevant text and select it. I have transcriptions for all my meetings now. Years ago, I might have needed someone to sit in on all my meetings to take notes, but now I have instant notes and can easily search them.

I just met with a founder this morning who’s using AI chat for research—they don't run traditional surveys; instead, they have an AI research chat popup when a customer fails to convert. When they conducted surveys, the response rate was about 2%. With AI user research, they see 30%. And customers aren’t just dropping brief comments; they’re writing paragraphs of feedback. He thinks it’s as valuable as a full research interview. And if this happens at 2:00 AM, in the moment instead of days after the fact, that’s hard to match without AI.

Do you feel like there are roles that you just love having in human form and you would keep in human form?

Absolutely. At its best, AI isn't so much replacing us as it is freeing us to focus on more human aspects of our work. When AI handles tasks like taking notes, I have more time to engage directly with people, empathize with them, and really understand their needs.

The same is true for our product team. As AI takes on things like generating repetitive code or summarizing customer feedback, our team members can dedicate more time to devising thoughtful solutions to their problems.

Sudowrite is an AI tool for authors, and it can help in all stages of the writing process. We tell people, yes, you can do everything yourself, but most writers have parts they love and parts they don’t. Some might love writing but hate marketing their book. Or they might love getting that first draft out, but dread the editing—or the opposite. We encourage writers to bring AI into their workflow to help with what feels like a chore. When they're operating in their zone of genius—where they excel and feel most alive—they don’t need AI.

Yeah, cool. We've talked a bit about how much you've changed as a person, and I'm curious— today, what do you aim for your life to look like, both as a founder and as a balanced human with a wife and new baby on the way. What do you desire that to look like?

For me, the most important thing is having control over my time. Being fully remote helps. Currently, I dedicate a lot of my time to work. It feels like a game that I'm good at, one that I enjoy playing every day. I'm also passionate about mentoring and supporting people’s growth within the company. I value these parts today, but I value even more having the flexibility to shift my focus as needed.

I love spending time with my wife, and working from home means I get to see her more. Being able to see my parents a few times a year has been really important to me, too. I’m sure everything will change or nothing will change once the baby arrives, who knows!

Okay. I'll ask you one more question related to everything we just talked about. What advice would you have for folks thinking about starting something today in their own unique way?

Talk to people, read biographies, listen to interviews like this. Send that cold email or DM to someone you admire. In my experience, most people are very open to talking, helping, and mentoring others. One of the coolest aspects of tech is how approachable people are. Talking to more people will help you understand what you want and how you can get there. Because there are so many paths, and you can certainly make own path, but knowing what’s possible can be really eye opening.

Cool. Thank you.

Can I ask you some questions now?

Sure.

How would you do it today, if you were to build something again?

I would do something very similar.

Do you think you’d raise from individuals?

Yeah.

Would you do dividends or would you keep raising as you grow?

I would choose to build a profitable business. I think that's just the best leverage you can have. I couldn’t say never—there could be a world in which I’d do another VC or PE-backed thing down the road. But it is hard for me to wrap my head around putting a future business under that kind of risk. If it goes wrong, then I have to sell another business in a fire sale and I just don't want to do that ever again.

Your pacing is also different in that scenario. You’re not coming at it with the same urgency—having to reach venture scale quickly or you lose your business in 18 months. That pressure feels insane to me now. I would take my time.

And also, like you said, I would want it to be more fun this time around. You use the game analogy a lot. I’d want it to feel like that. To really enjoy the process of figuring things out and solving problems. To remember that that process can actually be fun.

I have more questions for you, so now I'm just going to interview you if you have time.

Yeah.

Okay. Well, so I know a lot of people in software and SaaS do this build in public thing, and I'm curious if you've considered doing that for a CPG startup. I feel like it's not as common in that space, but it would be so much more interesting to me as a consumer to understand the whole process of building a CPG startup.

Okay, interesting you bring that up. So this summer is five years exactly from when Haus launched, and it's made me nostalgic and made me think that enough time has passed where I feel like I can start writing about this stuff with perspective. I have a pretty good idea of what was a good decision and what was a bad decision. And you’ve known me a long time—you know I am no stranger to sharing online. I've been sharing stuff online for 25 years now, if you count my Geocities website I built when I was 12. So I'm definitely pro-sharing.

But I went through a number of traumatic experiences building Haus—I was clinically diagnosed with PTSD afterward and am still recovering. And so I'm still trying to wrap my head around what to share and what is actually helpful, while also being mindful of my own privacy and recovery. But that's a long-winded answer to your question of yes, I've been thinking a lot about it.

I wonder, given your experiences at Haus, how much we as founders often hold back from sharing our experiences. A lot of founders have stories about nightmare investors. You might hear them private chats, but they're not shared outsid. Obviously, the reluctance usually comes from fear—fear that speaking negatively about one investor means other investors might hesitate to work with us.

But I wonder if that's really the case. For example, if you were to publicly share your experiences with a particularly bad investor—assuming their reputation is known in the investor community —I think other investors might empathize. And it could serve as a warning to other potential bad actors that such behavior won't go unchallenged.

Yeah, that’s all valid. But the risks—both of retaliation and of general blacklisting—are real. It’s a big part of why I haven’t wanted to jump back in.

I mostly just want to move on, but like you said, I also grapple with the responsibility of how that is not necessarily helping the greater good.

Yeah, yeah. Totally.

I am just hoping that with time it will sort itself out, right? I think people who make mistakes deserve a chance to do better next time. And if they keep up the same behavior, eventually they will cross someone who will either press charges or worse. I have to trust that either they learned from the experience or will improve, or they won’t. But I am ultimately not responsible for changing their behavior.

And I think the real offering to the greater community is teaching them how to spot someone with bad behavior—but not necessarily to call out individuals, because then you’ll still get taken advantage of by the next person. It’s about doing the work on yourself to understand why you let these people into your space to begin with, and learning frameworks that can protect you.

Can I share an idea with you?

Yeah.

I read this book a while back, so forgive me if I get some details wrong, but it reminded me of an issue I had at Photojojo with copycats, which really bothered me. Now, we're experiencing the same thing at Sudowrite. The book was about Benetton's founding story—stop me if you've heard this. Benetton was essentially the precursor to mass-produced fashion, at a time when much clothing was made to order. They started producing high-quality, colorful, yet affordable clothing. It began in a small Italian town and quickly caught on because people loved these suddenly affordable stylish clothes. Benetton soon realized that dealing with copycats was just part of the business.

So what they did was kind of ingenious. They started copying themselves, launching their own knock-offs, flooding the market with competitive storefronts under different brands. This made the market seem unattractive to new entrants because it seemed saturated. Every time I start a business, I'm reminded of this approach because I anticipate being copied. I often talk to James about the possibility of launching several other AI writing tools, each targeting slightly different segments of the same market under different brands. Create your own competition to discourage others from competing with you.

Oh boy. This definitely resonates. A lot of brands have been “inspired” by Haus. I don’t think that a lot of people understand that directly copying a successful brand won’t make your brand successful—if anything, it signals the opposite to me. When I see a brand that is an obvious copy of another, I immediately know that the founders are lacking in vision and creativity, and probably take shortcuts in all areas of their business. I’d argue that brand actually has very little to do with aesthetics—it’s about your values, and the brand that ultimately manifests from that.

What I wish people could copy from me, if anything, is the thoughtfulness that went into the work. Just be thoughtful, and you’ll go much further than if you take shortcuts.

That makes sense.

Do you care what people think about you anymore?

Yeah, I do. I wish I didn’t, but it seems like it’s always going to be there. I think this is another learning for me. I found this old notebook recently, where I'd made a list of things that I’m good at and things that I’m not good at. Flipping through it, I noticed many areas I wasn’t good at before, but I am good at now. There were also things I wasn’t good at back then and I’m still not good at today. LIke ignoring what people think. But now, I’ve reached a point where I’m okay with that. I don’t have to be good at everything.

Do you have a new method of self evaluation now?

I picked up something years ago from reading "The Effective Executive" by Peter Drucker, this very sexist, but classic tome of management theory. You meticulously log everything you do for a week, down to five-minute increments, then go back through it and mark which of those things gave you energy vs took energy away. It’s a very productivity-porn type of thing to do, but it’s effective.

But there's a part of me that wonders what it would be like to swing to the complete opposite end of the spectrum—away from productivity maximizing to just doing whatever you want. I do enjoy some of the productivity optimization, and I think it’s fun to introspect. Recently, I've gotten more into coaching, something I never did before. It's helped me pay more attention to my emotions and try to understand what they mean rather than pushing them away. We've also started working with a coach for the company, which has been super valuable, and also something I haven’t done before.

The Enneagram framework is another new tool for me. It’s been a good way for us to understand each other and how we all interact within the company.

You just got married, which is very exciting. That's a big commitment. Do you feel like you naturally have more of a balance between being a founder and your personal life?

Absolutely, 100%. And I think it’ll change again when we have kids and life gets even busier. It’s going to evolve. But my wife Nancy is also an ex-founder, so it’s easier for us to understand each other's ups and downs and to make space for what the other person needs. That’s been a huge help. She’s good at pulling me back when I get too sucked into the game. She pointed out, when I was stressing over wedding planning—that I always find something to stress about, whether it’s the wedding or some company issue. So it may not be that there’s anything wrong or in urgent need of attention; it could just be that I need something to fix. And I realized, “Oh, shit, you’re right. This is something I can try to change.” And even if something is wrong, I don’t need to let it bother me.

Looking back, how do you think your parents’ love story impacted your own journey in love and partnership?

It's fascinating, isn't it? It seems we either emulate our parents or do the complete opposite. I've noticed that Nancy is quite disagreeable, which is something she has said herself and takes pride in. My mom is the same way, and both wield this trait skillfully. They're also both incredibly capable—among the most competent people I know. Interestingly, my mom actually worked for Photojojo even longer than I did, staying on after the acquisition.

The traits that used to annoy me about my mom growing up became such an incredible asset when she worked with me. I knew she would never let anything slip through the cracks—nothing was ever forgotten. Anything that she said she would do, she would do, and she would expect the same from everyone else. Nancy isn’t that, but the similarities are there. It's something I'll have to think about more, but it's curious how we might be blind to the qualities that attract us to each other.

Okay, we’re running out of time here. What advice would you offer someone who is starting to build a company today?

The most high-leverage action I took was just meeting loads of people. In New York, I was constantly meeting new people and connecting them to each other, not because I thought it would help me, but because it was fun to do. I became the center for all these connections through hosting events, and inadvertently built this huge network. And then it saved my life. I doubt I would have received the same level of attention and coverage for my leukemia journey without those connections. Those same people I helped have ended up helping me in some way in everything I’ve done since.

If I could give advice to my younger self, it would be to invest even more, invest in bringing people together. Whether it means spending more on a great space for hosting dinner parties or hosting conferences, or just meeting people for coffee, whatever you can do to bring people together, do it.

I very much resonate with that.

Advice for myself at this moment, too. I want to do more of that today.

Yeah. For sure. My last question is… how can the community support you?

Hmm. Well, I do want to connect with more people. So if there are people out there who want to connect with me after reading this, or if I can help them in some way, I would love to talk to them.

I love that. Thank you so much.