Take a look at what he’s writing about:

• Unsolicited career advice: You don’t need to know what you’re doing

• 10 startup lessons (early-stage knowledge)

• How long does it take to raise venture capital?

Ritika: For as long as I’ve known you since 2010, you’ve described yourself to be a stubborn entrepreneur.

Where did your founder journey begin?

Jesse: Technically, it started with a blog.

Back in 2005, my college roommate started a Blogspot site to document his summer in Europe. When I graduated and took a job in Thailand, I followed his lead.

I didn’t think much of it—I was just trying to keep friends updated on my life.

But when I moved back to LA and couldn’t get a job, I added “blogging” to my resume. That’s what finally got me in the door.

That moment flipped a switch for me. I realized: writing could be a way in. It could be a calling card.

Ritika: Did that open the door to entrepreneurship?

Jesse: Eventually.

Blogging helped me find my voice—and my community.

Around 2010, I started an anonymous dating blog. I’d give the women I dated nicknames—“Donut Girl,” “Circuits Girl”—and people got deeply invested. Like, really invested. They’d leave comments, root for certain people, even push me to go back to the ice cream shop and ask someone out.

It sounds trivial, but it taught me a lot about audience building. If you bleed, they read. I wasn’t performing. I was being real. And people responded to that.

Ritika: How did that translate into your agency work?

Jesse: I launched a social media agency and later evolved it into a digital marketing firm. Ironically, blogging wasn’t even one of the services we offered—but everything I learned from blogging shaped how I built brands.

Authenticity. Voice. Vulnerability.

These weren’t buzzwords for me—they were muscle memory. When I worked with clients, I wasn’t giving them playbooks. I was trying to help them connect. The same way I connected with strangers through stories about my awkward love life.

Ritika: At some point, you shut everything down and moved to Jakarta. What happened?

Jesse: I hit a wall.

The last startup I tried to launch had promise, but I couldn’t get the product together in time.

I drained my savings, piled up debt, and stalled out my career. I was burned out and stuck in zombie mode—not growing as a founder, not growing as a professional.

An advisor gave me an ultimatum. He said: “Give yourself a deadline. If you don’t hit your goals by then, shut it down. Move on.”

That date came. I let go. And it was a huge relief.

Three weeks later, I moved to Indonesia.

Ritika: What led to that move?

Jesse: A college friend helped me get a job at a global agency in Jakarta.

I packed a single bag and left. I didn’t even know Indonesia was the fourth-largest country in the world.

But it turned out to be exactly what I needed. I started over. I healed. I learned a whole new side of the business.

And for the first time in years, I took a vacation.

Ritika: When did the writing come back?

Jesse: Ironically, when I was writing an article about newsletters for a client.

I decided to start one just to test some ideas. At first, it was a roundup of links. But I’d add a personal paragraph at the top—and that’s what people really cared about.

So I dropped the links and just kept writing. Essays, reflections, updates from my life in Jakarta.

People I hadn’t talked to since high school started replying. People I barely knew from college sent thoughtful responses. It reminded me of that early blogging magic—the intimacy, the connection.

Ritika: What kind of things do you write about now?

Jesse: Whatever’s on my mind long enough to matter.

Aging. Health. Career pivots. Anxiety. Startup fears. I don’t post every week. I wait until something feels worth saying.

When I write, it’s not a therapy session—but it is therapeutic. It helps me see things clearly. Sometimes I don’t even know what I believe until I’ve written it down.

Ritika: You mentioned you’re starting a new company. What’s the spark behind it?

Jesse: Jakarta is an emerging market with real momentum. More startups, more capital, more energy. I see opportunities everywhere—and I want to build something that fits this moment.

In talking to investors, I’ve been more prepared. I’m more aware of what can go wrong.

Writing helps me process that. I’ll sit down and draft something that might turn into a newsletter—or maybe it won’t. But just by getting the thoughts out, I calm down. I see things more clearly.

Ritika: What keeps you coming back to the phrase “stubborn entrepreneur?”

Jesse: Because I know this is who I am.

Yes, I’ve failed. But I’ve also grown. I’m not trying to prove anything to anyone anymore. I want to build something real, something that matters.

I’ve done the hustle-until-you-break thing. I’ve had the identity crisis. I’ve let go.

And now I’m ready to start again—but this time, from a place of strength.

Portrait illustration by Kat Cao

• My billion dollar mistake

• You don’t have time for boredom

• How to focus when you’re overwhelmed by marketing options

Ritika: Every entrepreneur’s path looks different.

How would you describe the beginning stages of your journey?

What were the influences in your life that inspired you to start a business?

Hiten: My journey started when I was maybe 4 or 5, right after my family moved to New York from Zambia, where I was born.

My father, an anesthesiologist, told me that I would be an entrepreneur because it was one of the few professionals that would allow me to be creative and use my brain for the rest of my life.

He believed that his profession was one that he could do from memory—he didn’t feel challenged, and he didn’t want me to feel that way.

In the 80s, this way of thinking was unusual.

Most of my friends’ parents wanted their kids to be just like them—doctors, lawyers, and engineers. But my parents pushed me to be independent.

The way I would deal with my boredom was open every electronic device in my house and try to put it back together. I did that to my radio, phone—everything. I never got in trouble. I saw the inside of every electronic device in my apartment, growing up.

Every day, my dad would come home from work, and we would eat dinner together. After, he’d go back to work and take me with him to the hospital. My dad would leave me in the computer room. I’d take them apart and put them back together. I learned how to program in QBasic.

In high school, I continued on with my passion for learning how things work. I started fixing up my car. Then I started selling car parts so that I could pay for my car’s modifications.

Ritika: It seems like entrepreneurship, for you, was a perpetual state of motion.

At what point did you establish your first real company?

Hiten: It was when I graduated from college.

My brother-in-law, who was four years younger than I am, had a client paying him $3,500 a month for marketing consulting. My now-wife, his sister, suggested that we start a business together.

So we started a marketing agency together, and that’s what guided me towards the world of online software companies.

From there, we ended up launching a dozen company ideas within 2 years. This was from 2003 to 2005.

We started making money from these platforms pretty quickly and began pouring those funds into new ventures. That’s just how we were—we loved experimenting and having fun.

Neither of us were technical at the time, but we picked up concepts pretty quickly. We started hiring people and building up teams with all kinds of skills like design and engineering. We had a web hosting company, that we spent $1M of our own money on, that we never launched.

Eventually, in 2005 or 2006, we landed on an idea called CrazyEgg. That company is almost 15 years old—it’s still around.

This company struck a nerve with people because it solved an important website usability problem in helping people see heatmaps of clicking and scrolling behaviors. We built the company using our consulting business’s revenue.

Our second technical company was KISSmetrics, which we received venture funding to co-found in 2008.

I ended up leaving in 2015.

Ritika: How did you end up choosing your focus and concentration area in your business?

Hiten: I’ve always valued human relationships, whether they are one-to-one or in a group setting.

In society, we’re inundated with messages from our family members, partners, colleagues, teachers, etc.

Communication is everywhere and something that I always want to improve upon. It drives adoption and engagement in terms of people gravitating towards what you’re doing. There are so many platforms available to get your message out there.

But really, the value of communication runs much deeper. Think about the stories we learn even before we learn to speak from mannerisms, gestures, facial expressions, and all of the ways we learn when we are young. Think about our online lives. Everything that we put out on social media is about building affinity with other people.

Ritika: In addition to running businesses, you also spend a lot of time blogging, sharing knowledge on social media, and speaking at conferences. Why?

Hiten: I like helping people. I want to be authentic and genuine. This passion is very personal to me.

I want to help people take action immediately and be able to implement what I’m saying. I love when I feel like I’ve empowered someone.

I used to say stuff to people, and they would contact me 6 months later to tell me that I was right. After a while, I realized that this wasn’t my goal. If someone reaches out to me 6 months later, it means that I’m doing a poor job explaining to them what they can do, right now.

Being right isn’t important. Offering value is.

Ritika: One of your most helpful blog posts that you’ve written has been about the failure of KISSmetrics as a business.

Can you tell me more about that experience?

Hiten: It was called “My Billion Dollar Mistake.” The story begins with the success we found after navigating two failures. After a series of business pivots, we finally hit the right points in the market.

But after that, I really screwed it up. This is something that I’m willing to admit objectively and without emotion.

I kept dropping new ideas on our team, which made it difficult for people to focus and execute. Everyone at the company started calling them Hitenbombs behind my back. They were frustrated. Nothing could get done. It became a company-wide joke.

At the time, I thought I was being a great communicator in sharing my vision and balancing opposing forces. Instead, I tanked my company by refusing to let go of my own perspective and trusting my team. My Hitenbombs ruined our once-strong position in the market. We were always changing and never steady.

As leaders, we can do better—so much better. We need to be self-aware that we’re balancing a lot of forces. We’re human ourselves. What we need are systems and processes to translate our innermost thoughts into relatable ideas. Leadership isn’t innate. We need to manage ourselves.

Ritika: What’s your process now?

Hiten: I write down my ideas. I don’t share them with anyone until I’ve fully crystalized and synthesized them. I share my notes with my team to gather feedback, so that they have the same information that I do. I don’t tell them what to do. I don’t drop Hitenbombs. I’ve stopped sharing what’s on my mind.

I focus more on sharing things factually and keeping my opinions separate. If I’m navigating opinions, I write them down first to work through them. I make sure that there is a pattern to the things I’m learning before sharing them.

Ritika: How did the dots connect for you?

Hiten: For a few years, I wouldn’t talk to that many people. I realized that I needed to spend time alone, to focus on myself. My departure from KISSmetrics took a lot out of me. As you can imagine, I navigated a lot of negativity. I needed to find my footing.

I came out of my shell in a better, 2.0 type of way.

I needed to change.

Nobody wanted to see me puke out my crap.

I learned that lesson the hard way. Hitenbombs were me just puking what was in my head. There are venues and settings for that — outings with friends, therapy, decompression sessions — where there are rules and we can all just puke.

But if you’re doing this at your company and making people deal with your vomit, that’s not okay. When you start puking, other people start puking.

It’s my job to make sure that nobody has to deal with this, from me. If someone’s looking to do work, and the things I’m sharing are distracting them, then that’s inappropriate. Nobody has time to clean up my messes. That’s my own job.

We’re building a business. Nobody has time to clean up each others’ messes. My rules are simple:

• Be clear

• Be factual

• Label opinions as opinions

• Give people the space to open up with their own opinions

Ritika: Do you still have fun?

Hiten: We just spent the last 10 minutes of this conversation sharing profound life lessons through puke analogies.

Did we just have fun?

I mean, we’re laughing right now.

Clear communication doesn’t need to be sterile. When you talk to me one-on-one, there’s a lot of color. I get really passionate about certain topics, especially in business.

You can still have fun and be clear.

Ritika: You are constantly communicating, writing, and thinking.

How do you balance it all?

Some people struggle to write just one email.

Hiten: I have a strong set of relationships with people who help me level-up.

For instance, for a few years, someone had been teaching me and my co-founder Maria how to write better.

This person is our editor and has done an incredible job streamlining our work. It’s because this person knows how to write a certain way, has leveled up, and has worked with the best people around writing, email marketing, and communication. I have energy to improve my writing.

I have infinite energy for creating as well. That’s why I like building businesses — and more than one at a time — because I have infinite energy for learning.

If I had to give anyone advice it would be to figure out what you have infinite energy to do. You’ll naturally want to focus on these things. People think about time too much. Energy is what matters.

If you are passionate enough about something, you can do it — and do a great job — even when you’re tired. That’s when you stop focusing on time.

Portrait illustration by Kat Cao

Ritika: I’ve always perceived you to be such a dynamic person with a beautiful imagination and intellect. Your storytelling career path is something I admire quite a bit.

Have you always been this way? What were you like as a child?

Kathryn: I was an explorer.

A thinker.

A people watcher.

I read constantly—so much that teachers worried I’d walk into a wall with a book in my hand.

On planes, I’d have a stack of books with me.

As long as I had something to read, I was content. I loved learning. I loved following my curiosity, whether that was through a book or a bike ride out into nature.

I wasn’t especially social. I was happiest following whatever idea or topic had captured my imagination in that moment.

Ritika: When did you realize that storytelling would become such a long-term part of your journey?

Kathryn: Pretty early.

I wrote my first story in second grade, and people fussed over it enough that I thought: this is it. I also won a poetry contest around the same time. That kind of validation lit a fire in me.

I thought I’d be a fiction writer.

But I struggled with it. I’d get discouraged.

Maybe I overanalyzed everything because I studied English. Whatever it was, I couldn’t quite get it right.

But over time, I discovered I’m really good at nonfiction storytelling.

It took a while to accept that. I didn’t come from a writing family. There was no roadmap. It felt like I was missing a secret handshake everyone else knew.

Ritika: What happened next? How did your journey continue to unfold for you?

Kathryn: In my early 20s, I realized: maybe I’d built up my skills, but I didn’t have something to say yet. So I paused. I had kids. I lived life. And then one day, it hit me…I was helping everyone else chase their dreams, but I was ignoring mine.

I told my family: I’m not ignoring you, but I need to put this first. This is my time.

I went to a writing retreat. I started reconnecting with the writing community. And I came across a book by Bob Bly about making money as a writer.

At first, I resisted writing for business. I’d worked in a university PR department, and they wanted me to go pro in that space. But I thought, no—I’m a creative. I didn’t want to compromise my writing dreams. Eventually, though, I reached a point where I didn’t care what I wrote. I just wanted to make a living as a writer.

Bly made the case for copywriting. So I gave it a shot.

I read books, taught myself the craft, and used my self-promotional writing as my portfolio. That landed me a senior copywriter role at a financial services company.

Ritika: How did freelancing come into play after this time of career exploration?

Kathryn: I stayed in that financial services job about three and a half years, then jumped back into freelancing. I wanted more freedom. I wanted to work on different projects. I wanted to see what I was capable of.

The day after I quit, I sat at my desk thinking: Now what? But then it hit me—I’d already done everything I needed to do for that company.

I just needed to do it for myself.

So I created my own marketing systems. Started a blog. Got on social media.

That’s when I realized: content had been my thing all along. I’d been doing content marketing before I even had a name for it.

Ritika: And then came a major life disruption.

Kathryn: Yes.

In early 2011, I had a car accident. At first, it didn’t seem serious. But within days, I was in excruciating pain. A back injection caused bleeding inside my spinal cord. I became paralyzed. Not immediately—but over a few days, my legs stopped working.

Emergency surgery saved my life, but the prognosis was bleak.

They told me I might never walk again. I went home unable to feed myself. I was in bed, mostly flat, for four years.

Ritika: In all of this, you chose to keep your business going…

Kathryn: That first year, I kept the blog going. I did a few client projects.

Every morning, my husband or son would set up my laptop next to me. I couldn’t hold it or sit up, so we rigged a way for me to type.

I worked from bed. One post at a time.

After a year, I was stronger. I decided it was time to grow again. I couldn’t go to events. I couldn’t network in the usual ways. So I went all in on digital. I tweeted. I blogged. One of my posts caught the eye of Russ Henneberry at Crazy Egg. He brought me on as a writer.

Within a few months, he recommended me to take over the blog.

That role was a turning point.

I discovered what I’m best at—content strategy, writing, helping others find their voice. I loved it.

Ritika: And then, another curveball.

Kathryn: Yes. Years later, just as I was getting back on my feet—literally—I was diagnosed with breast cancer.

I chose not to do chemo because I’d been doing stem cell therapy, which had helped me regain mobility. I didn’t want to undo that progress. I did surgery and radiation.

And I kept working.

Right as I finished treatment, Sales Hacker reached out. They offered me a content manager role. I’d always resisted full-time jobs, but this one felt right. It reminded me of Crazy Egg—only better.

I was tired of working seven days a week to juggle clients. I wanted a five-day week.

So I said yes.

Ritika: What helped you keep going during the hardest moments?

Kathryn: Planning helps me stay sane.

Having something to work on—even a single blog post—gives me purpose. The first year after my spinal injury, I could barely move. But I had four weeks of blog content scheduled, and that gave me a cushion. From there, it was one post a week.

Then social media. Then client work. One step at a time.

Eventually, I made a rule for myself: I wouldn’t take projects that didn’t bring me joy. If I didn’t like the work—or the people—I let it go. When your circumstances are hard, you have to create joy wherever you can. That meant being more intentional. More selective. More honest about what I wanted.

Ritika: Looking back, what surprises you most?

Kathryn: Honestly, that I built a career from bed.

Everything I’m doing today grew out of those years. It wasn’t part of some grand plan. I didn’t have a vision board. I just kept layering the next thing on top of what I’d already built. It was intuitive. Step by step.

Ritika: And what have you discovered about yourself along the way?

Kathryn: That I’m more of a people person than I thought. And more of a leader, too. I always saw myself as task-oriented. Head down, get things done. But I’ve learned I care deeply about people. About helping them find their voice. That’s been powerful.

Ritika: You now work with sales professionals. What drew you there?

I’m not a sales expert—but I’m a content strategist.

I help sales leaders tell their stories in a way that resonates. I help them sound like the best version of themselves. That’s where I shine. I love helping people feel confident in their message.

Ritika: What’s your broader mission?

Kathryn: To teach people how to use their voice. Through content. Through storytelling. Through writing.

I want to help people communicate clearly, confidently, and with purpose. Whether that’s in business or in life. Whether they’re navigating a personal challenge or just trying to build something that matters.

I’ve also got a lifestyle blog—Vivacity—that I’ll return to one day. It’s about resilience. About choosing joy. About building a life even when things fall apart.

Ritika: What advice do you have for aspiring writers?

Kathryn: Don’t wait for clients to give you permission. Just start.

Start a blog. Start building your space. Use your own projects as a sandbox. Learn how to express your ideas. Learn how to run your own platform. It builds your skills—and your confidence.

When clients do come, you’ll know what works. You’ll understand what they need. Because you’ve done it for yourself.

Portrait illustration by Kat Cao

Adam’s work blends deep literary analysis with cultural commentary. His mission: to reveal how the artistry of language—whether in a novel, a poem, or a rap verse—shapes identity and speaks to power. Learn more about him on his website.

Ritika: You shaped the direction of my life as my professor. I was so lucky to have you as my senior college thesis advisor.

It’s amazing how you’ve influenced so many students through your work and mentorship.

Where did your own journey begin?

Adam (AFB): I can trace it back to a moment of failure. In first grade, my teacher told my mom, "Adam's the sweetest boy in class, but he’s just not that bright."

I struggled with reading. A lot.

My mother pulled me out of school, moved us in with my grandparents in Utah, and my grandmother—who was a high school English teacher—quit her job and said, "I can teach this boy to read."

Within weeks, I was reading. Then writing.

She sent me into her garden with paper and a pencil and told me to describe what I saw, felt, heard, smelled.

I was six years old, writing poetry, learning that words could change the way people see you—and the way you see yourself.

Ritika: There was a turning point for you in college.

You became connected with Ralph Ellison’s literary estate.

How did that happen?

AFB: When I was a college sophomore, I took a class at Lewis & Clark with a professor named John Callahan.

He happened to be Ellison’s literary executor. When Ellison passed away in 1994, Callahan hired me as a research assistant. I was 19.

That summer, I helped him edit Ellison’s unpublished work.

To be entrusted with those pages—some never seen before by anyone except Ellison and his wife—was transformative.

It shaped everything.

It gave me the courage to apply to graduate school, to pursue literature professionally, and to honor the kind of rigorous, honest storytelling Ellison believed in.

Ritika: What was it about Invisible Man, Ellison’s book, that impacted you so deeply?

AFB: It’s a novel that is unapologetically Black and yet insists on its universality. It starts with "I am an invisible man" and ends with "on the lower frequencies, I speak for you."

Ellison had the audacity to say: my story, my pain, my lens on the world—it’s not just mine.

It’s yours too.

That blend of particularity and universality—that’s what literature can do. It helps us connect the dots between our individual identities and a shared human story.

Ritika: You also became one of the first scholars to study hip hop as poetry.

How did that thread develop?

AFB: During my time as a PhD student at Harvard, I was studying Chaucer and Shakespeare by day, and listening to Tupac, Biggie, Wu-Tang, and Lauryn Hill by night.

One morning I walked into my generals exam with "Triumph" by Wu-Tang Clan blasting through my headphones.

I realized the same rigor we apply to canonical poetry could—and should—be applied to rap lyrics. When I started teaching at Claremont McKenna, I took the leap.

I wrote Book of Rhymes, and later co-edited The Anthology of Rap. I wanted to bridge communities: the poetic and the street, the classroom and the cipher.

Ritika: What was the reaction to the anthology? Did you face resistance?

AFB: Absolutely.

I submitted my first proposal to top university presses. Harvard returned it with a three-line rejection.

Said it wasn’t "academic enough."

Then a young agent reached out.

Within two months, I had a book deal with Basic Books. When the anthology came out, it landed alongside Jay-Z’s Decoded and the early days of Rap Genius.

Suddenly, we were having real conversations about lyrical craft.

I like to think we helped spark a cultural shift—where rap lyrics are treated with the respect they’ve always deserved.

Ritika: You’ve talked about how literature connects the personal with the collective. How do you see that playing out in your teaching today?

AFB: Every year, I meet students who remind me of why I do this. Students who want to send books to incarcerated people. Students who want to use their rage as fuel for change. Students who care deeply about justice and identity but don’t always have the words for it yet.

My job is to help them find the words.

And to remind them that their stories—like Ellison’s, like Baldwin’s, like the best of hip hop—can speak on the lower frequencies for all of us.

Ritika: You’ve spent decades on projects that don’t fit into our fast-paced world. What keeps you going?

AFB: Some of these projects span decades. I spent years working on the authorized biography of a major rapper, and after 200+ interviews and a 200,000-word manuscript, the estate shelved the book.

It hurt. But the long game is the only game I know. That’s why I’m working on an expanded edition of Invisible Man for today’s readers and updating The Anthology of Rap to include the last decade of music.

Legacy takes time.

AFB: What advice would you give to young people navigating today’s identity politics, media fatigue, and cultural divisions?

Stay human. Don’t mistake noise for substance. Cultivate your interior life. Read more. Write more. Spend time in real conversation. Be willing to live in tension—not everything needs to be resolved in a tweet.

And remember that the struggle toward justice and clarity isn’t new. You’re part of a lineage. Honor it. Continue it.

Ritika: Where can people follow your work?

AFB: I keep a low profile. You can find my books in libraries and bookstores. That’s where I’d like the conversation to start.

Portrait illustration by Kat Cao

In addition to his entrepreneurial accomplishments, he’s authored several books about calmer workplace cultures. You can learn more about the impact of his contributions on his website and read one of his most popular blog posts, Reconsider.

If you want to give your eyes a break from reading, you can listen to a high definition recording of the conversation on SoundCloud.

Ritika: You’ve lived life experiences that people can only think of in dreams.

You've driven 5,000 kilometers through France.

You've started one of the world's most notable companies that changed the way that people work online.

People learn from you.

I'd love to go back to the very beginning of it all, before any of this unfolded, before it manifested.

What was life like when you were first getting started?

David (DHH): I was born in Copenhagen, Denmark, and I lived there until I was 25.

As I was growing up, I always liked computers, so that became a focal point of the hobbies that I had.

I loved video games.

I played a lot of video games.

I thought I was going to be a video game creator at some point.

I tried to learn programming to basically make computer games, and I failed a bunch of times.

I think it took four times, trying to learn programming over the years until it finally clicked for me.

The real opening for me was the internet. Just as I was coming through high school and trying to figure out what I wanted to do and what I wanted to pursue, the internet was kind of blowing up.

I thought this was just amazing.

I was into video games, as I said, and before I could go on the journey of thinking about creating them, I thought, well, let me just write about them. So I did video game journalism for quite a number of years. The internet was just a perfect position for that, because I was still in high school.

No one was really going to give me a column or whatever in a magazine, a printed magazine, but here's the internet, and I can just put whatever I want online.

So that's exactly what I did.

I started a couple of websites and built up the skills of organization.

We had a whole distributed team, actually, back there in, what's this, '96, '97, where we didn't have any funding.

We didn't have any money.

I would go to a video game shop in town and basically walk up to the guy who ran the console division and ask him if I could borrow the games, such that we could review them, so we could write about them, and so could put that stuff online.

That taught me a lot about the constraints. It taught me a lot about organization.

It taught me a lot about remote work.

We were all distributed over the country of Denmark, and I would send out the cds with the games to the different reviewers in different towns. I kind of just got a lot of satisfaction out of building something. There was nothing.

There was not a website.

Then I started working on a website.

All of a sudden, there's a website.

There's a community.

There's readers.

There's writers.

I'm interfacing with publishers.

We started going directly to the people importing the games in Denmark and asking if we could just get the games from them, rather than having to go down to the local shop to borrow them.

I was building up all these skills that are still, today, the main things that I rely on to do the work that I do.

And it all sprung up out of just a passion for video games, and a passion for publishing and making something of my own, and to be in an environment where I could do what I wanted to do with nobody telling me any different.

Ritika: What happened next?

DHH: I took a number of jobs working for technology companies in Copenhagen.

In some ways it felt like, wow! I'm getting paid to do this stuff.

For years, I hadn't gotten paid. We hadn't made any money whatsoever. We'd only spent money trying to publish all these video game reviews and so on, and all of a sudden I'm getting paid, and that feels, oh, that's amazing!

I quickly learned that just having a paycheck was by no means enough.

Working for other people is not inherently a problem. I mean, I've worked with lots of people who I respect or enjoyed working with.

What I had to give up to get that paycheck was not worth it for me.

I was just building up all this ... I mean, it sounds harsh…but I kept thinking, “I don't want to run my company like this. This is a shitty way to run a company. Why are they doing it like this? Can't they see that we, as workers, ended up miserable from their actions, and completely needlessly so. They're not making any more money because they're acting in these ways. And I was just building all this up. ”

Justin: How did you make that chance, ultimately, to branch out on your own and leave the workplace and start your own company?

DHH: It happened sort of slowly.

After I had worked in a number of startups in Denmark, around 2001, everything came crashing down. The dotcom boom turned into a bust, and I saw the writing of the wall in 2001 and thought, you know what? I don't have to stick around for the crater.

So I quit the company I was working for at the moment and thought, let me just go to school for a while.

That seems like a good place to hide out while all this rubble is being sorted through.

So I got into the Copenhagen Business School, and attended a joint program of computer science and business administration. And it says computer science on the label, but it really wasn't computer science.

It was some very introductory courses to computer science that weren't really that deep.

But what it was was information system design. It actually had some great classes on that, and that was something I was really interested in.

I quickly learned that the part of the computer that I was interested in was not the computer science part. I was not fascinated by compilers.

That was just not a topic of interest.

I was really fascinated about building information systems, and building systems in general for actual human beings.

I didn't know at the time, but that was a great foundation that I'm happy that I've gotten out of it.

But towards the end of the three year program, I had already taken up consulting, writing software for clients.

I had connected with Jason Fried, who is now my business partner at Basecamp, and started working with him, which is sort of a roundabout way we got involved. He had a blog he had started in 1999 alongside the company 37signals. It was called Signal v. Noise. I'd been a reader of that blog since '99, and was just a big fan.

And then, in 2001, Jason was trying to learn PHP programming and asked a question on the blog. I was like, wow! This is my moment to give something back. I've gotten so much away from this philosophy of how they were designing things.

The 37Signals website, for example, here's a design company that does design for clients, and the website has no design.

Or it has no graphics, I should say.

It had a lot of design. It had no graphics.

It was a manifest of 37 short, punchy essays on how 37Signals saw business. And I just thought that was fascinating.

Because, especially at the time, everything had flash intros and mouse over animations and all of this graphics, and here's a design company that doesn't do graphics.

What is that?

So I just became a big fan, and I wrote Jason back with a detailed answer to his question about PHP. We started trading emails, and Jason decided it was simply easier to hire me than it was to learn how to program in PHP.

So we started working together.

We'd worked together on a number of client projects and around 2003, we had some trouble dealing with those client projects.

Everything was just managed on email, and as with anything that's just managed on email, eventually it falls apart.

There's got to be a better way.

We're making technology. We know how to program. We know how to design.

Can't we just make a system so it isn't such a mess, so we don't have to lean on email so much?

So that's what we did.

And that was Basecamp.

We started creating Basecamp in the summer of 2003, and I built it alongside going to school, again, with heavy constraints of pursuing my degree and I also liked rollerblading.

I liked to go out with friends.

I'm not just in it for 100 hours a week. So I had all these other things going on, and then I was building Basecamp on the side with Jason and the rest of 37Signals.

So I had about 10 hours a week to make that happen.

It took us just over six months.

We released the first version of Basecamp in February of 2004. During that process, I was also learning a new programming language.

I had just picked up this little known programming language at the time called Ruby. And Ruby, when I picked it up, didn't have a lot of stuff to help you learn how to build web applications or websites.

So I built what was needed to basically just build Basecamp.

That was what became Ruby on Rails, which I then released open source in late 2004.

So I think that's pretty much the trip.

Ritika: Wow. That's amazing!

One of the things you said that was interesting was that you were spending around 10 hours a week working on this.

I wonder if you could shed some light on this kind of work/life philosophy and balance?

DHH: Yeah.

The question I often get, or the accusation, I should rather say, that I often get when I talk about 40 hours a week being enough is, "Yeah, that's fine for you to say now.

Basecamp is this big success, and you don't even have to program Ruby on Rails anymore. There's all these contributors. But I'm sure when you got started you probably worked 100 hours a week, right?"

It's just taken as an assumption that anyone who ends up building something of note, they started out pouring everything that they had, 100% of their mental capacity, into the thing, because otherwise it would be impossible.

So when I say, well, that's not how I did it. That's not how we did it, usually I'm faced with this look of incredulity.

They just cannot believe that that is actually true, that we were building Basecamp on 10 hours a week. And the funny thing about the 10 hours is the reason I know so specifically was that I was billing 37Signals for the time.

This was a consulting project.

The first version of Basecamp was billed at about 385 hours, spread out over the time it took us to build it. So I know in quite specific detail how long it took, because this was how I was paying for my technology.

It's funny to look back at now, but Jason was paying me $15 an hour in early 2000.

This was, obviously, at a time where the dollar was a little bit stronger against the Danish Krone, and I wasn't even getting paid in dollars, right? Because what I wanted most of all, I just wanted some technology.

So he would send me an iPod when that came out, the first iPod. I would get an iBook, one of the first Mac laptops that ran OS10 that was new at the time.

So I'd just get all this stuff that Jason would order, and then he would pay the invoices in that, basically.

I think sometimes origin stories…they get more airbrushed over time. And I'm sure there's some airbrushing involved here, too.

It wasn't just ... So I spent, or I billed 10 hours a week. But I also spent some time above that doing some Ruby programming and so on. So it's not like it was just exactly that.

But it wasn't 100 hours a week. It wasn't even 80 hours a week. And it surely was not even 40 hours a week, because I was going to school full time, and I was doing the things that someone going to college would do, and participate in life, and not just lock me into a room and do nothing else than the pursuit of business or whatever else have you.

And that's what It Doesn't Have to be Crazy at Work is about.

Push back against this idea that to do great things, or even to do good things, or even to be content doing things, that you have to be completely absorbed in just one activity for however long it takes for that thing to be a success. We try to put out a different ideal, and say, first of all, what are you chasing?

A lot of people are like, well, I have to put all this in because I want to be this enormous thing.

What are your aspirations, and start there.

What are your goals? Why are they the biggest thing ever? Why is that a goal in itself? And maybe if you've set your sights on something that's both more plausible, realistic, and fulfilling in many ways, you'd be better off.

And then once you have those goals packed into a more sustainable place, you can design work practices around that that are healthy, sustainable, maintainable.

And being in technology, I often also get the question, so what's next?

Essentially, when are you going to sell your company, or pursue something else?

Because there's this assumption that no one could keep up the rigor of building a technology company for 20 years and come out on the other side and want more.

Because there's just this stereotype that it is one definition of hell, right?

That it is this death march all the time.

And if that's the image you have in your head that someone is just sleeping under their desk, working 100 hours a week, yeah, of course you'd ask when are you done with that torture regimen?

When are you getting out of that?

But if it's not, then why would you get out of that?

What is it that I'm going to do that's so different than what it is that I'm already doing?

Justin: One of the really interesting things that Ritika and I have experienced as we've been building our business is a lot of times, we've either put things off to the side and come back to them months later, or run into these delays.

And when we did, we often found that we came up with better ideas for ways to do what we wanted to do that got us father along than if we had just been sitting there, working on them the entire time tirelessly.

DHH: A hundred percent.

Taking breaks, recharging, that's where the big leaps of productivity are hidden.

And it's so funny, too, because there's lots of people in technology who believe the heroic myths, for example, of the 10x programmer, that some programmers and some people in general are just 10 times as productive as other people.

How do you think that is? Do you think it's because they type faster?

That they type 10 times as quickly as another programmer, that that's how they're so much quicker?

Of course it's not.

It's because they have better insights. They have better ideas. They think more clearly.

They have insights that are leaps, not just strolls, right?

And to get those insights, you have to be in a special place, and that place is well rested, well nourished, well slept, well situated.

At least that's my belief, that there's where I got my great insights from.

It was not when I had worked all night, which I've done several times in my career.

The ideas that I would get at the end of an all nighter were usually the ideas that I would then have to spend another three days cleaning up afterwards, because it would be a total mess.

Ritika: I ask you this question from the perspective of someone who doesn't game, who's fascinated with gaming, but what are some things that you learned as a gamer that you have carried through to adopt these philosophies?

DHH: That's a great question. I have three boys.

That has forced me, or invited me, to take a look at parenting as a general concept, and to think about what were the things that worked for me when I was a kid?

And how do I want to put those same opportunities in front of my kids?

One of the answers is video games, is play, is focused play. I learned so much from video games. I credit video games with all sorts of things, but the perseverance of getting better at something, leveling up, and sticking with it, and realizing that you have to put in the time. Again, it's not about putting in the 18 hours, although I surely did game for 18 hours some days, I'm sure.

But just that there is this trajectory where you can get better, that video games have this amazing opportunity of especially allowing kids to influence the world in ways that are quite limited for a lot of kids outside of that domain.

Most of the time, most kids don't get to call the shots.

They don't get to decide when to get up in the morning.

They don't get to decide whether or not to go to school most days.

They don't get to decide all sorts of things that they want to decide.

So here's video games offering them a universe where they can make all sorts of choices, authentically, on their own, and learn just how much power is in that.

I took that away from video games.

Ritika: What does “leveling up” mean to you?

DHH: It’s really the pursuit of mastery.

Leveling up your skills, leveling up your capabilities, getting better.

And I think that is the feedback loop that I’m addicted to—of seeing where I’m at, realizing there’s a whole other level, and then figuring out how to get there.

A lot of the time, leveling up is just about widening your field of view.
You start to notice things you didn’t see before.

Like with photography—I got into it maybe fifteen years ago.

At first, I didn’t know what made a photo good. I just had this gut feeling like, “That looks nice.”

But when I really started paying attention, I began learning all these layers: rule of thirds, white balance, focus, ISO, focal length… all these factors that go into how something looks and feels.

You absorb the vocabulary.

You start recognizing what’s going on inside a picture.

You can break it down. You can replicate it. You can improve it.

And I love that.

That process of going from “I don’t know what this is” to “I understand this domain”—that’s something I chase in so many areas: writing, programming, building a business, racing, photography, even something as weirdly specific as indoor air quality systems.

Ritika: Wait—air quality?

DHH: Yeah.

So we built a new house recently. And my wife got sick from formaldehyde poisoning in one of the rooms—because of poor ventilation.

That was shocking to me.

We just built this house… how is it making us sick?

So I dove in.

I started from zero—no knowledge about HVAC systems or VOCs or anything. But I went down the rabbit hole. I read everything I could, talked to experts, learned how to measure air properly, how to understand airflow and filtration.

And I ended up solving it.

More importantly, I leveled up.

That’s the theme that connects all of this for me.

Whether it’s racing, writing code, or figuring out air flow—I’m always following that thread of: how do I get better at this?

And if I hit a plateau? I start looking for new angles. New routes. New ways to keep climbing.

Because when I can feel myself growing, when I can see that I’m objectively better than I was before, there’s just nothing more satisfying than that.

Justin: Changing directions a little bit, one of the major things going on right now for a lot of people who are doing things in Silicon Valley especially, but elsewhere, is this idea of imposter syndrome and self doubt.

I wonder if, going back to when you were consulting and starting out and building your first company, were there ever any moments where it wasn't so clear that you were necessarily going to create this incredibly successful thing?

And how did you deal with those?

DHH: A hundred percent.

When I first started doing programming, I never thought myself as a programmer, or that I was going to do programming. This was sort of just something I had to do to get the things I wanted. And I wanted to publish video games reviews online. So I had to figure out how the ASP and the PHP and the other systems we used back then kind of worked, because it was just such a hassle to constantly have to go to another programmer and ask that person to make the changes I wanted. It would just be more immediate. I would have a more direct influence on the world if I could do these things myself.

So I learned programming as a skill in that regard, not as a pursuit.

And it took a long time, until I fell in love with programming, as it was something I was going to do for the rest of my life. And I just didn't ... I didn't treat it in that way.

I didn't treat it in the way of, oh, I'm learning programming now because I want to get on this path of making something great in programming.

No.

I learned programming because I wanted to build some specific things, and this was just what I needed to do.

Given the fact that I hadn't internalized the idea of being a programmer, I had a very distanced relationship with programming, that I didn't know a bunch of things, and I had to ask people all the time. And I was very inefficient, and very just poor programming.

The funny thing about programming is I tried to learn programming probably about four times before it clicked.

I tried to learn programming at six years old, when I got my first computer and tried to type in a game from the back of a magazine.

Then I tried to learn it again, I think, at about maybe 12 or something?

And then I think I tried again around, like, 15 or so.

These were all failed attempts.

I wanted to learn programming, because I wanted to do some stuff with programming, but I couldn't figure it out.

And I can still remember the things I couldn't understand, which is just a fascinating concept. Like, variables, for example.

And then I can remember other programming techniques like recursion, methods of functions that call themselves. It was just something that I could not wrap my head around. And I have these vivid memories of trying to crack it, of getting my brain to somehow turn the wheels in the way that this would be understandable. And they just wouldn't. And it then took sometimes years where I had to leave it, and not think about it, and then come back to it. And then, the fourth time was when some of it clicked. And then, later on, more of it started clicking faster.

So I've been in those exact shoes, as well.

What I perhaps didn't have was this constant bombardment of imagery and Tweets and people telling me how wonderful and great they already were for me to compare myself against poorly. I think that was one of the wonders of the early internet, that we didn't have those things. I was learning most of my programming from actual books

Ritika: That's interesting you talk about social media, because now you can't escape it.

It's pervasive.

And you're still building, you're achieving new levels of mastery and new areas in education, and social media's such a part of what you do.

How do you strike that balance?

DHH: I have a very ambivalent relationship with social media. I recognize all the ills of it, and I also recognize that there are many goods of it.

But it's also part of a system and a machine that's incredibly unsatisfying and detrimental to people, to societies, to professions.

I think there's all sorts of nasty things in the sense of the addiction that it causes, and I'm not about that.

That's the insidiousness of it, that they're hacking core human functions that it's just lizard brain reacting. And even if you're observing it, and even if you're aware of it, the lizard brain is still acting. You can know that these things are unhealthy.

Justin: One of the things that I learned about you recently is that stoicism is important to you, and it's something that has a large influence in your life.

I wonder if you could talk a little bit about what its meaning is to you

DHH: The reason I came to like stoicism is because I recognized a lot of my own thoughts in it. I recognized a lot of my own unpolished thoughts and thought patterns, really, not just thoughts, but thought patterns and techniques of how to deal with experiences in the very refined framework that is stoicism. Well, at least comparatively refined to my beta, home grown ideas on these things.

There was just such a revelation to ... Here I am, processing the world in a certain way, thinking, maybe I'm the only one who thinks like this. And then, encountering stoicism and stoic ideas and going like, wow! 2,000 years ago, someone thought in exactly these same ways?

That is amazing.

That recognition of some of the core principles, for example, negative visualization, was something that just went, like, okay. There's clearly some kindred spirit here that if I independently arrived at a very similar technique to one of the stoic core techniques of negative visualization, then let me see what else they have.

I kept pulling on the thread, and kept finding things, and kept finding perspectives and a way to view life in a really grand, yet practical, sense.

So I've been exposed to all sorts of philosophy over the years. Some of it had been sort of mildly interesting, and I've always had a sort of an affinity for reading about that, and how people think.

But what struck me about stoicism was just how utterly practical it was, and that it was derived from the same way and the same challenges of life that 2,000 years ago, they were worried about the same things. They were worried about overwork.

They were worried about what other people thought. They were worried about, essentially, imposter syndrome. They were worried about all the same anxieties and problems that we face today. They were the same. And the human mind, in that regard, hasn't evolved very much. In fact, maybe it's regressed in some regards, that there was a greater focus and attention to try to wrestle with that in productive ways.

When I first started reading books, I read mostly technical books. I've never been big on novels or what have you. I wanted practical tools. So I read a bunch of technical stuff, both in terms of programming and then I read a bunch of business books. Out of maybe the hundred books of more that I read in those two domains, I can count maybe two that I wanted to read again.

Then I found books on stoicism.

I found that here were books that I wanted to read again. Not because I didn't know what they had to say, but because I needed to be reminded about what they had to say. That was a breakthrough in some regard of it's not just about the accumulation of knowledge.

It's about the constant rejuvenation of the ideas that are truly important and that will naturally decay from your present mind if you don't frequently refresh.

Ritika: You speak of leveling up, and that you're still wrestling with stuff, and many of the people listening, they'll look at all of the things that you've achieved, and they want to achieve just one.

They want to write a book.

They want to start a software company.

They want to race. They want to get somewhere racing.

I'd love to learn, what are you wrestling with right now? What is that next phase of leveling up for you?

DHH: One of the great insights I've taken away from learning a lot of different things to a reasonable level of mastery is that the process is quite similar, whether you're learning how to drive a race car, you're learning how to program, or how to write a book, or start a business, or photography, it's not that dissimilar.

You start out knowing nothing, and that's a gift. It's a very special time.

The beginner's mind is a magical place that lots of people keep trying to get back to.

There's whole branches of philosophy focused on trying to recapture the beginner's mind.

It was the beginner's mind, it was the ignorance, that led me to create Ruby on Rails.

If I had known everything that I know now about what it takes to run an open source project at this level and that had been presented to me, oh, yeah.

Here's 20 years of work with lots of ungrateful strangers on the internet yelling at you constantly over all sorts of decisions, maybe I would have gone, like, that doesn't sound like a good idea at all.

Let me not do any of those things.

But the ignorance of not knowing the limits of my own capacity ... I was just learning Ruby at the time when I created Ruby on Rails. Essentially Ruby on Rails is more or less like my first project in Ruby. I just stuck with it. But it was the beginner's mind that allowed me to do that. It was that gift of ignorance that got me started.

But then, of course, after that, you go through these phases of learning what the grand constellation is, of what the terms are, what the major things are, and they're really fuzzy still, and you don't know how they all work together.

Then things get clearer, and you feel like you have ... Okay, I have somewhat of a solid ground.

I know what people sort of are talking about most of the time. But I don't have any input of my own. I'm just still absorbing.

Then you get to some level of proficiency where you understand, okay, now I know what people are talking about. It's not that fuzzy anymore, and I know how things work together. And I'm starting to form some opinions of my own about how things interact, and how you can do things better, or how you can do things differently.

And as you go through all these phases, it's the same progression.

Once you've been through that once or twice, you're no longer surprised that when you start in a new domain, that you are ignorant.

When I started learning about air quality, I knew going in, I knew nothing. I have the beginner's mind here.

That's a gift that'll allow me to ask a bunch of questions of professionals that seem maybe dumb or irrelevant, and sometimes insightful because I'm taking just something I know from some other domain of systems thinking or whatever and applying it to this new domain. In any case, this is just a phase I'm going to go through.

There's no way I'm going to learn something where I can just jump over those phases, or just jump over being a beginner, where I just jump over being an intermediary. When you've been through that process, you simply accept that that is the process, and it takes some time.

So for me now, that's sort of where I am with a lot of philosophy reading.

I'll read some philosophy book, like Being in Time, where I go, this is really dense in a way where I don't really understand most of what's going on here. But if I stick with it, I will at some point.

And then, you read more and you read more, and you read more, and you try to get it from different sources. I found, especially for learning philosophy, YouTube is wonderful. There's a bunch of great YouTube channels where you have someone else basically re-tell the material to you in a modern interpretation. And you go, ah! Now I kind of understand it. And then you can go back to the original text and all of a sudden, that starts making sense.

That's the step. I'm at such a beginner's phase on the quest of philosophy right now that I can just ... I can cherish it, because what I've also found is of all the different phases, mastery's not necessarily the best.

Race car driving is another example. I've been driving race cars now for over 10 years. I still enjoy driving race cars, but I don't enjoy it as much as I did when I was first learning.

When first learning to drive the car, it was so overwhelming, it needed 110% of all the brain power I had available in such a way that I would close the door, turn on the engine, boom!

Flow.

Just enter the stage, right? Be completely engrossed in the activity to the point where there's nothing else in the world than throttle, brake, steer, counter-steer, making it around the corner.

Such an engrossing experience, it's a version of bliss.

Now, because I've actually gotten so much better at driving race cars, it doesn't require, most of the time, 110%, it's not as enjoyable. So I wish, in some regards, that I could just go back and be an intermediary or even a beginner and erase some of that, and then get to have those experiences again.

Justin: The 24 hour Le Mans race.

What was your mindset while you were doing that? It's such a battle of wits, almost, to keep driving for 24 hours on a competitive level.

I'm curious to know what you were thinking.

DHH: The first time I did the race ... was just magical, because you show up, and you have all this conception of what it takes to drive for 24 hours, and then you actually do it, and in some ways it's that, but in many ways it's very different.

It was such a battle against how much have I leveled up?

Have I leveled up enough to do this?

And realizing that, in the physical sense of doing it, and getting up after an hour and a half of sleep at 3:30 in the morning, and then they're like, "All right. You've got to get back in the car in 35 minutes. Get ready!"

And you're like, whoa, what? And get all your gear up, and you're standing there with excitement and thinking, I got to go out there and I can't fail.

I mean, I have two co-drivers. There's a whole team. It's not just me here. I'm not just playing a video game where I can just hit reset. There's a criticality that's a different level, and not withstanding just a mortality part of it, too, of driving a race car 200 miles an hour in the dark. There's a sense of obligation that you don't think about, perhaps, as much when you're fantasizing about what this is going to be.

But that's the fun of it, right? The fun of it is just actually experiencing these ideas that you have, and how it's going to be, and realizing, yeah, okay. In some ways they were what you thought. In many ways, they were not. This is why we do things, to be surprised, to be challenged, to live through it.

I kept doing the race.

It was just such a wonderful physical challenging, too, especially when I drove the race in the prototype cars that are extremely physical to drive, pull upwards of 4Gs. There's just a satisfaction from fatigue, and from pushing that boundary that's really satisfying in a way that is so alien to how I usually work.

Because as we talk about, usually I don't have any of this stuff. I don't do all nighters. I don't do ... And all of a sudden, there's this, I've got to be awake for 36 hours. I got to drive a race car. I got to ... It's such an alien experience that that's why it's good.

I don't have a stressful job. Maybe sometimes it looks like that from the outside, but that's not what it feels like. I feel like I have very little stress in my work.

I do think that having constant stress is one of the key killers.

Having constant stress will lead to all sorts of medical complications, and will kill you. But having some stress, sometimes, of your own choosing?

That can be good for you.

Justin: Have you found stoicism to be helpful in these competing at a high level? Things like racing or trying to do something that requires a lot of performance outside of racing?

DHH: Hugely, especially in racing, I'd say. In racing, there's so many things you cannot control.

As a driver, you have the power of steering the car, but you didn't make the car. And there are different kinds of cars, and there are different cars that are better on some tracks and worse on other tracks.

You didn't even put it together.

You didn't set it up.

There's engineers, there's mechanics, there's all these other people you have to rely on that have a great impact on your performance. So you cannot derive it down to just like if we fail, that's my fault.

Or if we succeed, that was my fault.

I think that's a good metaphor, in general, for society at large. It's never your fault, solely, if you fail. It's never your fault, solely, if you succeed.

Also, the stoic mindset helps you keep that in mind, that why am I getting worked up over this?

Race cars fail all the time.

If my race car fails, that is natural. To get upset about that, okay, there's an impulse where you go, like, oh, man, that's a shame. But then, this is the natural order of things.

This is what happened.

So I think the primary takeaway I have from stoicism is to separate the perception from the reaction.

You see something that happens, then you choose how you want to react.

Most people don't choose very consciously how they want to react. They simply react out of instinct or passion. And those reactions are often poor. They're not adjusted for the reasonable.

We get mad over all sorts of things that make no sense getting mad about.

Right now, there's probably 2,000 people complaining that their flight is delayed.

Just that fact alone. If there's 2,000 other people complaining that their flights are delayed, this is common. Why are you not expecting that flights are delayed? Why are you getting all riled up over the common nature of things? What good does that do you? Are you better off being mad about the completely expect-able? I don't think you are.

So learning to separate perception from reaction, and practicing that, is one of the, if not the greatest, lessons of stoicism.

You can choose.

You can live a better life if you are more considerate in your reactions. And almost all of life is inside of your reactions. Almost anything that happens, whether it's good or whether it's bad, is only bad or good depending on how you take it.

Portrait illustration by Kat Cao

Previously, Amy Nelson was CEO at Venture for America, a nonprofit that trained recent graduates and young professionals to work for startups in emerging cities across the United States. Rad more about her work:

• Rethink’s 2024 Annual Impact Report

• Welcoming Amy Nelson to the Rethink Education team

• Once a struggling single mom, Amy Nelson takes over Venture for America

Ritika: Let’s start with a big idea.

You mentioned before we hit record that America’s economic potential is strong—but entrepreneurship is in decline.

When did you start noticing this, and how did it become your mission?

Amy: I've always believed one of the most beautiful things about America is its vibrancy and openness to people from all walks of life. What sets us apart is our ability to create opportunity not just for ourselves, but for others through entrepreneurship.

When I joined Venture for America, I thought I was there to help solve the jobs problem in cities like St. Louis, Baltimore, and Detroit. But what I discovered is that the deeper issue is a collapse in entrepreneurship itself.

Since the 2008 recession, we’ve been creating fewer new businesses than we lose each year.

Millennials are on track to be our least entrepreneurial generation. And that’s a crisis.

Ritika: What’s standing in the way?

Amy: There are structural and cultural barriers.

Structurally, debt is crushing. If you ask people why they aren't starting businesses, that’s the number one reason.

Then there’s access to capital and networks. We celebrate tech entrepreneurship, but many of the ventures we really need—advanced manufacturing, clean tech, biotech—have steep upfront costs. If you don’t already have access, it’s almost impossible to break in.

Culturally, we’ve created a generation of excellent hoop jumpers. Kids are trained to follow the syllabus.

But no one tells them it’s okay to take risks or think differently.

Ritika: How did your work at Venture for America address those challenges?

Amy: We invested in people, early.

We helped aspiring entrepreneurs find their footing by embedding them in startups, helping them learn from founders, and building the confidence to launch something of their own.

We also supported them financially. We’ve forgiven student debt for some alumni using donor funds. We explored new funding models. Not every business needs VC.

It’s about alignment. When private enterprise, public institutions, and community partners share values, it creates the kind of conditions where founders can actually thrive.

Ritika: You didn’t start your career with a vision to steer entrepreneurship forward. How did this become your path?

Amy: I was raised by a single mom in a small town outside of St. Louis. I was the first in my family to go to college. In school, I studied philosophy. I thought I’d go into international development or law.

I worked in nonprofits and global development for a while, but I got frustrated. The work was good, but the systems weren’t sustainable. I started to wonder: what if markets could be used as a tool for good?

That’s what led me to business school, and eventually to Venture for America. I joined to lead fundraising. Four years later, I became CEO.

Ritika: In an era of cynicism, how do you stay optimistic?

Amy: Abundance. That’s my mindset. I used to operate from scarcity, especially in the nonprofit world. But I learned that if you believe things can work out—and you keep moving forward, they often do.

I also surround myself with people who are excited about solving real problems. I avoid the 24/7 news cycle. I try to read instead of scroll. I filter out the noise and focus on what I can control.

Ritika: What traits make a great entrepreneur, in your eyes?

Amy: Adaptive excellence. Can you drop into an unfamiliar environment, learn quickly, and start adding value?

Resilience. You have to hear "no" 125 times and still show up the next day.

Optimism. Entrepreneurship is a bet on the future.

And integrity. Your reputation is everything.

Ritika: What advice would you give to someone who wants to start something meaningful?

Amy: Start small. Don’t chase perfection. Run the smallest possible test. Try to make $1,000. See if your idea fills a real need.

And fall in love with the problem, not your first idea. That’s how you stay flexible and build something that lasts.

Portrait illustration by Kat Cao

He is known for championing underrepresented founders and driving systemic change through strategic investment. Read more about him:

• Social impact in 2025

• The man of many hats

• This poet turned financier is raising millions of dollars to fund Black and Latino investors and entrepreneurs

Ritika: You are such a known force and pillar in the VC community. So many people look up to you.

What were you like when you were younger? Could you have imagined that you would be a venture capitalist?

Taj: Absolutely not. I always say my parents were rich with knowledge, but not rich with wealth.

I grew up in an area of Dallas that was majority African-American, majority working class. Most kids my age back in the 80s had two aspirations: to be in sports or entertainment.

I loved to read.

I remember it was dangerous in our neighborhood, so I often stayed inside. I was just curious. I wanted to know what words meant, how to say things differently. I spent most of my time with the Encyclopedia Britannica and the thesaurus.

My mom saved up so much money to buy that encyclopedia set.

I didn’t learn about startups or venture capital until college. There was a gentleman named Reginald F. Lewis, a member of my fraternity. He was one of the first Black millionaires—before Oprah, before Bob Johnson. He made his money in private equity.

That was the first time I learned what alternative investments were. I remember seeing what he did, how he changed the food industry, and thinking: I want to do that.

Ritika: What was your path into VC? What were your college days like?

Taj: My path was definitely unconventional.

I studied poetry and literature. To be honest, I thought I was going to be a rapper.

So I figured, let me study the craft. Let me study poetry.

I didn’t become a rapper. I ended up working at Wells Fargo, which was my first job out of college.

And here’s the funny thing: I realized my background in literature helped me. I was able to attract customers because of how I told stories. That’s when I realized storytelling mattered. There’s a saying in sales: features tell, benefits sell.

And to sell benefits, you need to tell a good story.

I was horrible at math. I flunked college math courses. I never thought I’d work at a bank, but there I was. I had wanted to work at a newspaper, but the local paper in Dallas folded. This was 1997, right at the beginning of the internet wave.

I moved to Nevada on a whim. My roommates and I were sitting at home, and I said: I want to move. I threw a dart at a map. It landed near Vegas. The next day I packed my bags. I called apartment complexes on the drive over.

That move taught me I had an appetite for risk. Which later became useful as an entrepreneur.

In Vegas, I stayed with Wells Fargo and kept getting promoted. I ended up in California. I spent about a decade at Wells Fargo. Then I went to UBS Investment Bank. That’s where I started meeting high net worth folks—early MySpace investors, startup founders.

From there, I joined a private equity fund as Chief Economist. I’d finished my MBA and was working on my PhD in economics at Claremont. Around that time, I started investing my own money into startups. The first company I advised was in digital marketing. Then I got into e-commerce and social media.

I also became a COO. I ran a few of the companies I invested in. That gave me the founder perspective, which I think is critical in VC.

Eventually UC Riverside called me. They liked my work in the wine space. Wine is agriculture. It’s farming. Riverside is focused on agtech and cleantech. I became the first accelerator director at UC Riverside. We did a lot of outreach. We made Riverside the #4 place in the country for minority entrepreneurs, according to Forbes and Money Magazine.

Ritika: What needs to happen at a systems level to truly unlock funding for underrepresented founders?

Taj: To me, it’s never been a pipeline issue. It’s a relationship issue.

I’m in a historically Black fraternity. These relationships last beyond college. I know so many people with degrees in engineering, business, economics. The talent is there.

The problem is, VCs tend to back people they already know.

I’m glad groups like Backstage Capital and Harlem Capital started shifting that. Arlan Hamilton was often the first check for founders who went on to raise millions. But we need second checks too—who’s writing the Series A?

Ritika: Why does cleantech, particularly as a source of new value creation, need to prioritize diversity?

Taj: Because it’s not just tech. It’s infrastructure. It’s survival.

I’ll give you an example. When scooters came to LA, they all showed up on the west side. None in East LA. None in South LA.

At the Los Angeles Cleantech Incubator, we worked on a deployment strategy for scooters in those areas.

And guess what?

The scooters look different. They’re three-wheeled. They have baskets. Why?

Because people are using them for groceries. For commuting. Not just short joyrides.

Ritika: What do prospective cleantech founders need to know, particularly those who may be overlooked or disregarded for opportunity?

Taj: Start by educating yourself.

I love The Boy Who Harnessed the Wind. A young kid in Malawi builds a windmill for his village after reading an engineering book. He solved a real problem.

There are a lot of problems left to solve. You just have to listen. Cleantech isn’t just apps. It’s fashion. It’s food. It’s waste. It’s logistics. It's survival.

Founders need to understand capital too. It’s not just venture.

There’s venture debt, grants, philanthropic capital, city pitch competitions. In one of my startups, we couldn’t raise traditional VC. So we strung together hundreds of thousands through pitch wins across the country. Non-dilutive.

Ritika: When you’re considering potential investments, what makes a founder stand out to you?

Taj: Resilience. Clarity. And no fear.

A few years ago, I was diagnosed with FSGS. It’s the same genetic kidney disease Alonzo Mourning had. It was life-threatening. It changed everything for me.

I stopped being afraid.

Most of the decisions we make in life are about fear. We stay in jobs because of fear. We delay our dreams because of fear. Once that was gone, I started making decisions that mattered.

We’re all going to die. That’s not morbid. That’s freedom.

If you’re not scared of losing everything, you can start building the things that last.

Portrait illustration by Kat Cao

After overcoming a troubled youth and discovering programming during rehab, Dan went on to build and exit multiple companies, advise billion-dollar startups, and coach thousands of entrepreneurs through his platforms and YouTube channel.

His story is one of radical transformation, driven by clarity, community, and relentless self-investment. Learn more about him:

• From prison to prosperity: How Dan Martell mastered time

• I’m 44. If you’re 20 or 30, watch this.

• How to make so much money, it feels like cheating

Ritika: It’s been fascinating and inspiring getting to know the unique way that you run your businesses over all these years. Working for you was an adventure in intensity.

What stands out most is your unshakable true north. You’ve dedicated your life to helping entrepreneurs. What drives that mission?

Dan: I got into a lot of trouble as a teenager. At 13, I was addicted to drugs. By 17, I’d been arrested twice. I ended up spending 11 months in rehab. That program saved my life. It was there I discovered programming. When I got out, I found the internet, and that changed everything.

Software became my new addiction. And entrepreneurship? That became the ultimate personal development program.

I truly believe that every business issue is really a personal issue in disguise. If you want to grow a company, you have to grow yourself.

I had people who believed in me before I believed in myself. I made a promise that if I ever got the chance, I’d pay it forward.

Ritika: You didn’t always share your story publicly.

How did you reach that point of openness?

Dan: For 15 years, I never talked about my past. Not even with my fiancée. Only my family and a few close friends knew the extent of it.

Then I was invited to speak at MMT, my friend Jason’s event. It was packed with incredible people—Tim Ferriss, Marc Ecko, founders, investors. That morning, Jason announced there’d be a prize for best talk: $25,000 to the winner’s charity of choice.

I wanted that money to go to the rehab program that saved me.

So I scrapped my usual slides and spent two hours in my hotel room rewriting my talk. I shared the story I’d never told. How I tried to take my own life by pulling a gun on the police.

How I was saved.

How I started over.

When I stepped off that stage, people I’d known for years told me they had no idea. Tim Ferriss said, “Nobody looked at their phones during your talk.”

That day, I felt something I’d never felt before: a deep, real connection with the audience. I realized I’d been holding back the most meaningful part of who I was. I made a commitment to never hide that story again.

Ritika: You’ve talked about JFDI: just f*ing do it. What are the philosophies that have shaped your life?

Dan: Three core ones:

1. Become the person who can deal. Don’t wish life were easier—become better. Every challenge I’ve faced has made me stronger. I want to be the kind of person who can be sued for a billion dollars, like Oprah said. That means I’m playing big enough to matter.

2. You are your community. That’s why I moved to San Francisco at 28 with nothing but a suitcase and a bike. Within 2.5 years, I built and sold Flowtown. Surround yourself with people two years ahead of where you want to be.

3. JFDI. If your gut says go, go. Don’t wait until you have proof. Don’t rationalize your way out of it.

Ritika: What helped you go from chaos to clarity in your entrepreneurial journey?

Dan: Every painful experience was a teacher.

I failed at building teams. So I learned to lead.

I didn’t understand finances. So I learned to read statements.

Every time I hit a wall, I asked, what skill or belief do I need to upgrade?

I believe entrepreneurship is the only path that teaches you in real-time. The feedback loop is intense. It forces you to grow.

Ritika: You’ve been through burnout, rejection, and chaos. How do you keep showing up?

Dan: Reputation with self.

If I say I’m waking up at 5:00 a.m., I do it. That’s where confidence comes from. The promises you keep to yourself.

In my early days, a bad moment could derail me for a week. Now? Maybe a minute. I say to myself: “Not useful.” And I move on.

Challenges don’t get easier. You get better.

Ritika: What’s one decision that’s changed everything for you?

Dan: Hiring a coach. It’s not a weakness. It’s what high performers do. Olympic athletes have coaches. Why wouldn’t I?

My coach helped me through one of the craziest times in my life: newborn babies, building a startup, moving houses, running on empty. She gave me space. She reminded me what mattered. That changed everything.

Ritika: What advice would you give to entrepreneurs just getting started?

Dan: Invest in yourself. Books, courses, mentors. That’s the highest ROI there is.

And don’t let rejection define you. Get clear on your long-term vision. Trust yourself. Reframe failure as data. And keep showing up.

Ritika: Where can people follow your journey?

YouTube is my home base. I’m publishing videos to help software entrepreneurs scale with freedom. It’s part of a bigger goal: to reach 10 million founders.

Portrait illustration by Kat Cao

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Ritika: You’re incredibly sought-after for your ability to inspire and uplift others.

Were you always this way? What were you like as a kid?

Could you have imagined the life you live now?

Dorie: I grew up in a small town in North Carolina. A golf resort town, which wasn’t a great fit for me—lots of golf, not a lot of culture. I couldn’t wait to get out. I was a tomboy. I hated dresses. I hated the expectations that were put on me.

But I was lucky.

My mom was very open. She let me do what I wanted: sports, reading, getting out into the world.

When I was 14, I found a way to enter an early college program at Mary Baldwin College in Virginia. Two years later, I transferred to Smith. I finished college at 18. It gave me a head start.

Ritika: And then? What happened after college?

Dorie: I didn’t feel totally ready for the workforce, so I went to Harvard Divinity School and earned a Master’s of Theological Studies. I finished by age 20.

My career started in journalism, but that was short-lived—I got laid off in 2001. The newspaper industry was collapsing.

So I shifted to politics. I had covered campaigns as a reporter, and I figured I could work on them. But every campaign I worked on lost.

Eventually, I ran a nonprofit. And it was through that experience I realized I wanted to build something of my own. That’s how I became an entrepreneur. I’ve been doing that now for over 13 years.

Ritika: When you were starting out, could you have pictured this version of yourself—best-selling author, advisor, speaker, educator?

Dorie: Yes.

I’m one of those people who always wonders, why aren’t I further?

I’ve always had a sense of drive. I feel a sense of mission. I’m grateful for everything I’ve accomplished.

But I’m not done.

Ritika: Where does that drive come from?

Dorie: I wish I knew. It wasn’t pressure from my parents. My mom would’ve been happy as long as I was happy. But I’ve always held myself to a high standard. I don’t need to do something extraordinary to please anyone else. I need to do it to please myself.

Ritika: Along the way, you've faced rejection. How do you keep going?

Dorie: The key is to stop assuming the gatekeepers are right.

People treat rejections as absolute.

But gatekeepers are just people. They’re fallible. They have biases. Sometimes they just don’t get what you’re doing.

When I first pitched Harvard Business Review, I got a polite blow-off. The editor told me my writing needed to be different “somehow”—without explaining how. A lot of people would’ve given up. But I knew I had something to say. I wasn’t going to let someone’s vague dismissal stop me.

If you’re talented and persistent, you’ll find your way in. The problem is when people take one person’s rejection and decide they’re broken. That’s a perverse way to think. Don’t do that.

Ritika: What role should gatekeepers play?

Dorie: They serve a purpose. Not everyone can be on the TED stage. Not everyone gets a column in the Times.

But gatekeepers have a responsibility, too. They need to see the human dimension in all this.

Most of the time, when people get rejected, they hear nothing helpful in return.

Just: not this. Not now.

If you’re the one pitching, don’t internalize that. Their lack of interest doesn’t mean you’re unworthy. It means you need to keep refining.

If there’s a fence in your way, climb the damn fence. Dig under it. Go around. Figure it out.

Ritika: How do you set goals for yourself?

Dorie: I think in two layers: ten-year goals, and six-month goals.

The long view gives me direction. The six-month goals give me focus. I don’t try to map every year—too many variables. But every six months, I pick one or two major projects to push forward.

Ritika: How did you find the topics that resonate most with your audience?

Dorie: You listen.

If you’re in conversation with your audience, they’ll tell you. Their questions will tell you. One piece I wrote for HBR was about how to write a cold email to someone you admire.

It took off.

Because we all have people we look up to, and the internet makes them feel closer.

But the question is: how do you actually reach out? What do you say?

I’d been on both sides of that exchange. So I wrote it.

Ritika: How did you get your first book deal?

Dorie: It was slow until it was fast.

In 2009, I set a six-month goal to get a book deal. I wrote three proposals. They all got rejected. I wasn’t famous enough. I didn’t have a platform.

So I went back to the drawing board. I spent two years writing for high-profile outlets. First the Huffington Post. Then Harvard Business Review. One of my blog posts for HBR took off. They asked me to turn it into a full magazine article. After that, three agents reached out. Within a few months, I had a contract.

My first book, Reinventing You, came out in 2013.

Ritika: You often talk about resilience. What gives you the confidence to keep going?

Dorie: I know what I have to say is useful. That’s it. I’m not saying I’m the only one who could say it. But why not me?

Too many people get stuck in this loop: Who am I to say this? Why should anyone listen? But I think: Why not me?

If you believe your ideas can help someone, it’s your responsibility to share them.

Ritika: Do you ever deal with haters?

Dorie: Of course.

Especially on platforms like YouTube. Sometimes people email me criticism out of nowhere. I don’t let them get away with it. I respond.

People think they can say awful things with no consequences.

I want them to know they can’t. That’s not just for me. It’s for everyone they’d try to intimidate next.

Ritika: What are some of the biggest turning points you’ve experienced?

Dorie: There are two that come to mind.

One was when I realized my business was shifting.

I started out consulting for companies. But after Reinventing You came out, individuals started asking me about coaching. At first I said no—that wasn’t how I saw myself. But enough people asked that I eventually said yes. That flexibility opened up a whole new part of my business.

The second was ending a long-term relationship. I cared about the person, but staying together would’ve compromised my career.

She was jealous of the time I spent working. She was emotionally volatile.

It was hard.

But I knew if I stayed, I wouldn’t be able to do the work I wanted to do. Leaving was one of the hardest things I’ve done. But it gave me back my freedom.

Ritika: What advice would you give someone who's afraid of uncertainty?

Dorie: Reframe how you think about risk. Having one job, one employer—that’s not secure.

Diversifying your income, working with multiple clients? That’s real security.

And when it comes to sharing your ideas, here’s the truth: most people won’t even notice at first.

It’s not that they’ll hate your work.

They just won’t see it. And that’s a gift. You get to experiment in obscurity.

You get to improve. So that when the spotlight finally lands on you, you’re ready.

Portrait illustration by Kat Cao

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Ritika: Tell me about your incredible career journey.

You achieved what was, for many, a dream at a young age in your 40s.

How did you find your stride on this path?

Sunshine : I declared that I was going to be a writer before I learned how to read.

As soon as I learned how to write, I would buy little books and start to write. Sometimes, I would staple pieces of paper together.

Throughout my life, I felt like the dream was getting hammered out of me. But I kept going, and in college, I got published in a small newspaper.

I continued doing journalism.

That was before the Internet in the ‘90s. I would write for very little money or sometimes no money at all. Eventually, I got a short story published in a literary journal.

When the Internet started taking off, I was able to find my first writing job, at CNET. That was in 1997. I wrote about shopping online and computing for newbies. Meanwhile, I started working on a novel that had some promise. I spent three or four years on it. But it didn’t gain any momentum. I gave up. I wrote another novel. I gave up again.

Along the way, I held various roles in high-tech industries.

Eventually, I moved from San Francisco to a small town in Massachusetts, to write tiny pieces of news for a small town publication. I spent hours refining my craft until eventually, the newspaper hired me as a business reporter. It made a positive difference in my ability to write, and eventually, I was able to get a full scholarship to Columbia University for a master’s program.

Afterwards, a job at a tech magazine, Red Herring, brought me back out to Silicon Valley.

Around the time that the financial crisis happened in 2008, I decided to start my own business.

My timing was not great, but I did it. I don’t know how I did it, but a client from my full-time job really liked working with me, so I took them with me.

I wrote for their blog, I did their marketing, and I kept working on building up my skill set. I took a workshop and met a very encouraging teacher. She helped me write a memoir.

By 2014, I published my book. I was making quite a bit of money as a writer for the tech sector. Things were going so well that I could afford to hire a publicist. I had speaking engagements lined up for TV and radio. Everything seemed to be falling together in this perfect way. I was starting to succeed as a writer. My business partner and designer was my husband. Everything was lined up. I didn’t even need an agent or publisher—I was getting press.

Ritika: So you went out to celebrate, of course. You had spent four decades working towards this milestone.

Sunshine: One night, I went out with some friends to celebrate the book, and life in general. We went to this place in San Jose, in Silicon Valley, where there are little food stalls. There's a picnic table in the middle of a plaza.

We went there to sit, and it was kind of cold. So I sat under one of the big heat lamps that they use to keep people warm outside.

One of the workers came out to change the propane tank. He lost control of it. It fell on my head. It threw me forward.

I didn’t know what was happening. I didn’t pass out. It continued rolling and hit my friend in the face. Everyone was worried that he had been injured. Nobody was worried about me because I seemed fine.

But then I felt some tension in my neck. The EMT came and checked me out to see if I had a broken neck. They thought I was fine — just a sprain. I went home. But I wasn’t fine. There was something seriously wrong. It got worse and worse. I had to cancel all of my TV and radio appearances. I started having vertigo. I couldn’t work. Everything went haywire in my life.

Ritika: What happened next?

Sunshine: We were in a downward spiral. It felt like everything was spinning out of control. I was losing weight. I couldn’t find the necessary doctors in-network for my insurance plan, and had to pay a whopping $20,000 deductible. I relied on out-of-network doctors. All of a sudden, we were broke. I couldn’t work. I was sick all the time from the vertigo, and no doctors were able to figure out what was wrong.

My MRIs were normal. My CT scan was normal. The doctors thought that I was having emotional problems — some kind of psychosomatic reaction to trauma. Nobody wanted to treat me.

So I sank like a stone. I was falling through the cracks. My husband Leor was going out of his mind trying to help me. There wasn’t a straightforward treatment plan because there was no diagnosis. We tried going to alternative practitioners. Things got worse.

Ritika: What happened next?

Sunshine: I had a friend, Dr. M.R. Rajagopal (“Raj”) a prominent physician who runs a nonprofit palliative care organization, Pallium India that serves people who are dying or disabled. I had volunteered for this group, spending time in India.

Raj was visiting his son in San Jose, and we met up. He didn’t realize how bad it was. So he sounded the alarm to everyone in his network. He helped me get into the University of California, San Francisco (UCSF) medical system.

They saved my life by giving me much needed pain meds and muscle relaxers. But they still couldn’t figure out what it was — maybe my brain was having a phantom reaction. There wasn’t anything physically wrong with me that they could find, and they didn’t refer me to their neurology department even though it’s one of the best in the country. Had they done so I might’ve gotten diagnosed and treated right away instead of it taking years.

The vertigo was under control, so I started working again. By then, I had lost so much more weight. I worked for my highest paying client, from a hospital bed in my bedroom. There were nurses and social workers coming around.

Eventually, the client had a management change, so I lost them as a client. It was tough for me to network to find more opportunities. I hung in there. I ended up back in the hospital and spent a summer there.

Eventually, I was diagnosed with something that you can’t see on an MRI. It was a neurological condition similar to Parkinson’s, dystonia. A year later i was diagnosed with a second condition, stiff person syndrome, a rare autoimmune immune disorder. Both can come on after an accident.

Ritika: What happened next?

Sunshine: I had been up and down physically. At one point, I was doing so well that I could get out and about. I was able to meet with clients on-site.

One day, I went to go meet with a client at Stanford University campus. We had lunch, and I had a cup of tea and some food with me. She didn’t have any awareness that there was something wrong with me.

We decided to go upstairs. Suddenly, I was cradling everything in my arms, grasping on to the bannister. I was barely able to get up the stairs. I realized that I had been in the closet about being disabled. I was able to pull it off.

Ritika: What happened next?

I moved into a teaching career. There was a CEO of a known tech company who decided to step down. He wanted to learn how to blog rather than hiring a ghostwriter. So he hired me to teach him how to write. I really enjoyed working with him. That got me thinking seriously about teaching.

I’m not as sharp as I was before the accident. But I’m still able to write. I need to be more vigilant about staying focused. It doesn’t come so easily anymore, but I still put in the work. I still keep going. It’s hard to maintain a career with disability and chronic pain.

Sometimes, I take a step back and think how amazing it is that I became a writer. I pursued a childhood dream. I failed so many times along the way, and people told me I wasn’t good. I’m amazed that I pulled this off.

The book is still doing well. It still continues to sell. At one point, it was on a list of top memoirs.

Ritika: What inspired you to keep going…and continues to inspire you to keep going?

Sunshine: I’ve always known that my purpose on earth is to be a storyteller and writer. Even when I fumbled around and failed, there was something about just knowing that I was going to do it anyway that was powerful. It never went away, even after the accident.

It’s just still there. It’s a basic sense of who I am and what I’m here to do.

One of the great things about my book is that it’s been a resource for people with family members who are going through a gender transition. It’s helpful and affirming to them. I receive touching emails from people who the book has helped. Not to mention, it’s a nice story. It’s romantic.

I love what I do. I always have. My passion in life is something that has never changed.

Ritika: So what did change?

Sunshine: Most of my friends evaporated when all of this happened. Like most people in Silicon Valley, I had a super busy social life. I had friends. I had girlfriends—you know, people with whom you’d go out.

But they all just disappeared. There was nobody there. A few people from the palliative care community volunteered to help us. But it was all really bleak. The people who I assumed would be there for me just backed away. They were scared.

I was 47 when this happened. I was in perfect health. I wasn’t someone that you would ever imagine being in a wheelchair. But it happened.

People are scared of this stuff—very scared. I didn’t understand it at the time. I do now, but back then, I was just devastated.

It was horrible at the time. But it’s a gift, in hindsight. I didn’t have to wait until I was really old to find out what it’s like to be really vulnerable. I figured out who my friends were. I was no longer living in a delusion about people—I’m now far more careful about who I allow into my life.

Knowing these things is a gift. I no longer feel that I’m floating along, allowing others to take up my valuable time.

I remember I used to tell my husband that I wasn’t a strong person — that I couldn’t face what I was going through. But it turned out that I was a strong person. I could face it. That was an important thing to discover about myself.

I began to develop more of a spiritual life. I had always had one, but it was never a consistent thing. I meditated a lot.

There was one point in which I was in the hospital and couldn’t move. I couldn’t read. I couldn’t watch TV. I couldn’t work. I was just lying in bed, in pain.

At that point, my spiritual life was all I had. I began to realize that there’s a consciousness beyond ordinary everyday thinking—a kind and wise presence that will support you through the hardest of times. Without that, I don’t know if I would’ve made it.

Ritika: Do you ever wish you could go back?

Sunshine: As the years pass, I do wonder if I could have done without this gift. It’s been six years, and I’m still in it. I’m not sure, but it looks unlikely I’ll ever get out.

I wonder why I needed to go to the restaurant. Or why I made certain decisions. I have those kinds of thoughts. But I’ve stopped crying. The suffering is just there.

Would I rather be the person who runs when a friend gets sick?

Would I rather be afraid of suffering?

That, to me, is so much worse.

When I go out in public, I look at people. They all have this look on their face that I know very well. I just look at old pictures of myself, and I see it.

I see things in other people that they can’t see in themselves. Most people don’t have this ability. It takes a period of suffering to see it. People lack awareness of their own mortality, you know?

It’s something that I think about all the time. It’s a gift. I don’t know how long I’ll live. I don’t know if it’s going to get worse.

I’ve had periods of time where the pain was so intense that I couldn’t think. All I could do was essentially pray, which wasn’t a normal activity for me because I’m not religious. But I found myself in complete connection with the universe.

These are the peak experiences in my life.

After I was in the hospital, I was released to a nursing home type place—a rehab facility. In the hospital, I was in a room with no windows for three or four months. Then, suddenly, I was in a room where there were windows and fresh air. There were women speaking in Russian outside.

I lay there. I couldn’t move. I was basically paralyzed at that time. The sounds of the women talking was like listening to the most beautiful music.

It was one of the happiest moments of my life.

And then, when they got me sitting up, I saw a crow fly from a branch. Just seeing this crow, something so common, felt like the most beautiful thing I had ever seen.

Ritika: Do you see yourself as a role model?

Sunshine: I think anyone who gets up and gets through the day is a superhero.

So many people are struggling — with depression, physical stuff, or something else entirely. They have this super-human strength to get out of that.

Sometimes, I look back at the person I was before this accident. I feel jealous of her. I think, “Oh, come on, you could just leap out of bed.”

I had no problems. I’d wake up, exercise, and do all of these things. That could have been me for the rest of my life. But more often, I accept this. I’m grateful for the many gifts it’s given me. Empathy for those who are suffering. Patience. Understanding that the world we think we’re in is a delusion.

I did a lot of volunteering. I really thought that I understood people and had empathy. I did have some. But now I realize that what I had wasn’t empathy. It was sympathy. I felt sorry for others. I didn’t know how to step into their shoes and understand what they were going through. I didn’t get it at all.

Portrait illustration by Kat Cao

• Thoughts about AI and life

• Investment vs. speculation

• How to lose

Ritika: Brad, thank you so much for taking the time to talk with me and for everybody who's going to be reading, whether they be new entrepreneurs, whether they be career changers, people really looking to find their own path, the path that you've taken in life from using your intellect as your gift to becoming such a force in the venture capital world to empower generation upon generation of founders.

I can't thank you enough for that, and I can't thank you enough for all of the good that you are doing to for the global commercial ecosystem.

It's really wonderful to be talking with you today.

I'd actually love to go back to the days before all of this materialized.

Before you became such a notable venture capitalist, did you ever see this path for yourself, perhaps when you were younger or before you ended up at MIT?

What were you like as a child, as a teenager, and when did things start to become clearer for you as to what your purpose on this planet would become?

Brad: I don't know that I ever had a deliberate plan at any stage along the way.

Even when I sort of reflect about where I am today, I'm not sure that I have total clarity on my forward looking plan.

I don't think I ever do.

I'm sort of constantly allowing the things that I do and the people that I know and the stuff that I'm involved in and places that I'm curious sort of take me wherever they take me.

As a kid, I grew up in Dallas, Texas.

I was really fortunate. I had two loving parents of a younger brother that I'm very close to. My dad's a doctor, my mom's an artist.

It was definitely a privileged American upper middle class upbringing.

My parents had value systems around education and the importance of learning. These cultural norms were very deep.

From a very young age, I was always a very curious learner on a wide spectrum.

My parents held us to standards.

They gave both my younger brother and I lots of space to explore what was interesting to us.

A very memorable example I have…my dad was a doctor. I'd heard the stories from his father about how important it was for my dad, who was the oldest, to be a doctor…just in terms of my grandfather's view of what my father should do.

I hated everything about what my dad did as a doctor.

He would take me on rounds with him to the hospital.

I hated the smells.

But I loved to read.

I'd always curl up in the corner somewhere with a book, oftentimes under a desk to try to hide out of wherever the activity was.

When I was about 10 years, I remember very vividly walking into my dad's office.

He had study at a little office at our house.

At the end of the day, after we'd had dinner together as a family, he'd go into his office. He'd call patients and do the manual part of the charts that you would do as a doctor and sort of catch up on everything.

I was very nervous.

I sat down with him and he could tell I was nervous.

He says, “Brad, what's up?”

I just sort of blurted it out like a little kid blurred something out when they're nervous.

“Dad, I don't want to be a doctor.”

He looked at me and he sort of paused for a second and he said, “Brad, when I was your age, my dad said that I could do anything I wanted to do.”

“Brad, you can do anything you want to do.”

He set me free.

Ritika: What were some of the things that you began to explore after you felt that freedom?

Brad: Winding the clock forward as a teenager…the personal computer came out.

I bought a very early Apple II computer.

I was into computers. I played a lot of tennis. I liked running.

Something I learned about myself is that I love to be alone, and I love to be outside, whether that means going for a long hike or contemplating what’s going on.

I was a typical high school nerd. I was very into math and science. I also have always been and will always be a voracious reader of lots of different kinds of things. I read a huge amount of fiction…and also a lot of biography.

What I’m more interested in is stuff that challenges me intellectually. Science writing, ideas that are unfamiliar or hard to wrap my head around, new concepts that require me to think differently. That’s where I get a lot of energy.

Back in high school, that curiosity kind of set the tone for everything. I went to MIT, but even before that, during my junior year, I really wanted to spend a summer in Europe. So my parents helped me land a job with this little computer company in London. The company was called Tronix, and I spent the summer living with this older couple—a World War II vet and his wife. I was 16, living in London, getting to work and explore and just have that experience. It was incredibly formative.

Then in my senior year, I got a job working for a husband-and-wife team who had started a company in the oil and gas industry. They were writing software for that space, and I came in as a developer. I made $10 an hour, which at the time felt like a ton. And I learned really fast: if I worked 80 hours a week instead of 40, I made twice as much. They didn’t give me equity, but they gave me 5% royalties on all the software I wrote.

So as a freshman in college, I was getting these checks. Sometimes it was $1,000 a month, sometimes $2,000. One month, I got a check for more than $10,000 for something I’d written that they were still selling. It was kind of wild.

That early overlap—between business and entrepreneurship and software—was really powerful. But again, I wasn’t doing it because I had some master plan. I wasn’t trying to “be” something. It was driven by curiosity more than anything else.

Ritika: And at some point, as we’re jumping through time in this conversation, something started to really catalyze for you.

You’d been pursuing these curiosities, exploring these different avenues to find what you loved.

And all of a sudden now you are running multiple VC firms, including Techstars, which is one of the most notable platforms to empower entrepreneurs in the world.

How did this happen?

Brad: Well, first—an important point—I don’t run Techstars. That’s very deliberate. There are two co-CEOs, David Cohen and David Brown. They’re two of the four co-founders. I’m one of the other co-founders. I’m still on the board, I’m involved in strategy, I’m an investor, but I don’t run anything anymore.

And that’s true across the board. I was a CEO once. I started a company in my early twenties, and I ran it for seven years. We were self-funded, had to be profitable—there was no safety net. And we pulled it off. We sold it to a public company. After that, I stuck around for a couple years and got exposed to a whole different world—acquisitions, integration, being part of a much larger business.

That’s when I started doing angel investing, mid-’90s. Writing checks with my own money. Helping start companies. Even as late as 2000–2001, I still had one foot in operating. I was co-chairman of a couple companies, very involved. And then the internet bubble burst.

My world kind of collapsed. It was a mess. That’s when I made a conscious decision to stop operating. I didn’t want to run companies anymore. I wanted to focus entirely on the investor side—but not just writing checks and walking away. I wanted to be involved. Just not in charge.

And that’s where the shift happened. I reframed how I work with founders. Since around 2002, my personal mantra has been: as long as I support the CEO, I work for her. If I don’t support her anymore, it’s on me to either find a way to get back to a place where I do—or help the company make a change.

That mindset has shaped everything. I’m there to help. I’m not there to run things. And that’s been true with Techstars. It’s been true with Foundry Group. Nobody’s the boss. It works because we respect each other and we stay aligned on values.

Ritika: And to that point, I remember reading an article that you wrote a couple years ago, Falling Out of Love with Being CEO.

It struck me deeply. I grew up in Silicon Valley, where the CEO is often seen as the ultimate point of success.

I’ve seen that over and over again—especially in the early stages—this pressure to perform can really mess with someone’s sense of self.

I’m curious… what kind of introspection helped you see leadership differently?

And how did you start to separate yourself from that traditional CEO narrative?

Brad: Yeah… there’s a lot packed into that. The definition of success is always interesting to unpack. There’s the external version—money, power, recognition—but I think when you get to the end of your life, when you’re looking back on everything, none of that really holds up.

But that insight didn’t just show up one day. There were a few moments in my life where I had to really face it. One of the first was right after we sold my first company. I was still in my twenties. I’d been CEO for seven years. And I just… didn’t pay much attention to how I felt about it while I was in it. I was doing the job. I wasn’t really evaluating it.

Around the same time, I went through a divorce—my high school girlfriend and I got married young, and it didn’t last. And I also got kicked out of a PhD program. I wasn’t doing the work. I deserved to get kicked out. I was running a company and just didn’t care about the academic stuff anymore.

So all of that hit at once. Business success. Personal failure. A lot of identity stuff. And I dropped into a deep depression. It lasted a couple years. And I didn’t have language for it back then—I didn’t call it depression—but it was.

That was the first time I really had to reflect. Like: what am I doing? Who am I doing it for? What actually matters to me?

Then again in 2001–2002, when the internet bubble burst, my world just collapsed again. It was brutal. I had another depressive episode after 9/11. It lasted a few months. And that’s when I had this realization: I liked being involved with companies. But I didn’t like running them. I didn’t like being CEO. I was good at it. But it didn’t bring me any joy.

So that’s when I made the shift. Not because I had it all figured out—but because I started paying attention to what felt true for me. That’s really been the throughline ever since.

Ritika: You mentioned you’ve had multiple depressive episodes throughout your life.

One that really stuck with me was the one you wrote about in 2013—where from the outside, everything looked great, but internally, you were unraveling.

Can you walk us through that time in your life?

Brad: Yeah. That one was kind of sneaky. Because if you had looked at everything on the outside—on paper—things were awesome.

Amy and I were great. We were living in Colorado, which we both love. Foundry Group was doing well—my partners and I had a super close relationship, our funds were performing. Techstars was growing like crazy. I was in good shape physically. I had two golden retrievers. Like, everything you’d use to check the boxes was there.

But I had just worn myself out in 2012.

It started with an ultra-marathon in the spring. A 50-mile run. It took a huge amount of training to get ready for it. And I did it, which was great—but then two days later, I was on the West Coast working again. No recovery.

And then I just kept going. Traveled constantly that year. Didn’t slow down at all. In the summer, I went on this bike trip in Slovenia with my partner Seth and a few friends for his 40th birthday. On the second-to-last day, I had a near-fatal bike crash. Hit someone, bounced off them, landed wrong—if I’d gone over the guardrail, I probably would’ve died. Matter of inches.

I was pretty banged up, but I didn’t take the time to recover. I went straight to New York with Amy, and we spent the next month there celebrating her birthday. September is Amy’s birthday month, and we go all out for it. So we’re out every night, I’m still working during the day, and I just kept pushing through.

Then in October, I ran a marathon I had no business running. I hadn’t been training properly since the crash, but I did it anyway, mostly to support my partner Jason who was running his first. And I finished it, but… again, no rest.

In December, I got a kidney stone. Needed surgery. Went through that, and I remember thinking: okay. 2013, clean slate. Let’s go.

I flew to CES in January. Got there, walked into the hotel… and within two hours, I was lying in my room with a pillow over my head and the shades drawn. I couldn’t deal with people. Couldn’t deal with noise. And I thought: something’s really wrong.

That’s when the depression hit.

Ritika: So what did you do after that? When you realized it wasn’t just exhaustion—that you were really depressed?

Brad: The first thing I did was just acknowledge it. To myself. That’s step one. If you’re struggling with your mental health—whether it’s depression, anxiety, mania, whatever—you’ve got to be able to say, “Okay, this is real. I’m in it.”

That doesn’t solve anything. But it gives you a place to start.

So I started making changes. Tactical things. Not big philosophical shifts, just daily stuff. I stopped drinking. Cut out caffeine. No more coffee. I made sure to go outside every day—at least an hour—to walk or run.

I canceled a bunch of travel. Looked at my social commitments and just said no to the stuff I knew I wouldn’t enjoy. Not everything. But enough to give myself space.

I also stopped waking up with an alarm clock. That was a big one. For almost 20 years, I was that guy who got up at 5am no matter what time zone I was in. It was like part of my identity. But I let it go. I told people: I’m not starting my day until noon.

And I slept. A lot. Like 12 hours a night. For months. My body just needed it.

I also told the people close to me what was going on. Amy, obviously. My partners at Foundry. A few other friends. I wrote about it on my blog, too—by then I was comfortable being open about it publicly.

One of the best things that happened was my old business partner, Dave. He’s known me forever—probably better than anyone besides Amy. He didn’t ask, “How can I help?” He didn’t make me explain anything. He just showed up.

He’d check in with my assistant, find a time when I had a free hour, and then he’d come by and say, “Let’s go for a walk.” And we’d walk. Sometimes we didn’t say a word. Sometimes we talked the whole time. But he knew…it was about showing up, not fixing anything.

Ritika: You’ve been on both sides of this—going through it yourself, and supporting other people who are struggling.

What’s something you’ve learned about how to actually show up for someone who’s in a dark place?

Brad: Yeah… I think the biggest mistake people make is thinking they can fix it.

Like, you see someone struggling and your instinct is to say, “Hey, how can I help?” And that seems nice, but honestly—when you’re in it, when just getting out of bed feels like a win—that question is overwhelming. It gives the person another thing they have to figure out. “Now I have to come up with an answer that makes you feel better about what I’m going through.”

So one of the best things you can do is just be there. Don’t try to solve anything. Just show up. Sit next to them. Go for a walk. Be quiet if you need to. If you know them well, do something you already know helps—without asking for permission.

And if it’s serious—if you think they might be in real danger—don’t try to be their therapist. Encourage them to talk to a professional. Get help that’s appropriate for what they’re going through.

But yeah, a lot of it is just about being available. Being empathetic. Not judging. Not cheerleading either. “Come on, the sun is out! You’ll feel better soon!”—that stuff doesn’t help. It might actually make someone feel worse.

Instead, it’s about timing. Being steady. So that when they do finally peek their head up, when they reach out—even a little—you’re already there.

Portrait illustration by Kat Cao