The Hardest Battle Is the One Within

What a 10-day meditation in the middle of startup stresses taught me about startups (and myself)

“Adversity introduces a man to himself.”
— Albert Einstein (attributed)

It was October 2022. I had enrolled in a 10-day silent meditation program called Vipassana to take a break from the day-to-day stress of running a startup. I launched Jumpcut in early 2020 with the vision of building the first AI-powered movie studio. Finding it hard to operate on venture timelines—the time from initial story development to releasing a movie was simply too long—we pivoted to integrating blockchain technology into Film/TV. Within six months, the Web3 market had collapsed. I went to my board with a proposal for yet another pivot, asking them to bet on our new direction rather than simply take their money back. The stress of pivots, not finding PM fit, and explaining all this to investors was starting to show. This is when I remembered a conversation with a former student, Chris, who had told me about the wonders of a long, multi-day, Vipassana meditation course.

Upon arrival at the Vipassana venue in Palm Springs on that day in October, I surrendered all devices and distractions to focus on inner calm. We were not supposed to make eye contact with anyone or read books or take notes. Daily sessions began at 4:30 a.m. and lasted until about 9 p.m., with only brief meal and restroom breaks (roughly 12 hours of meditation per day). While I expected calm, my mind was instead besieged by anxious thoughts every day—what if the company failed, if the next pivot cost us more money, or if I had to lay off employees, or if investors felt I had let them down? With nothing to do and no external stimuli, a mind under stress will progressively gravitate towards more problems. Sure enough, the questions got progressively worse. If I failed, would people respect me? (and more such questions)

There was a daily emergency office hour with Tim, our teacher, and some attendees came by on an occasional day. I was the “most loyal customer” at these office hours. When I mentioned that I was struggling to sleep, Tim said, “It’s OK. Buddha only slept four hours.” I looked at him in disbelief, wondering how the enlightened one had become a benchmark for a mere mortal just trying to get through the night. By the third day, I began having what I now realize were panic attacks but at the time felt like deathly terror. I had no past experience with that kind of fear, which made it all the more disorienting. “What’s the worst that can happen?” Tim asked me another day while recapping his (far worse) ordeal the first time he did Vipassana. He survived and so would I, he insisted. I was honestly worried I was going insane–a strange sense of panic had gripped me. I begged Tim to let me leave. “Would you walk away in the middle of a surgery just because it is uncomfortable? This is brain surgery in progress,” he said another day while convincing me to persist. Somehow, I soldiered on. By the time I was done, I was completely shaken. For months after that, I struggled to connect with day-to-day reality. Here I had thought I’d find calm and clarity and answers for questions facing my startup and instead I came out with bigger questions. How could I find myself feeling so much panic sitting all alone in a meditation retreat with no obvious threat? Was something wrong with my mind? What got me here? Would I come out of it?

Figure: We were not allowed to take notes but I found a napkin in the room and scribbled some notes of encouragement for myself

“The wound is the place where the Light enters you.” — Rumi

Returning home, I began to reflect on my journey as an academic entrepreneur. My very first venture was founded with a fellow CMU graduate student who had started a web business selling baby and maternal products. I joined later as her technical cofounder. We were early in the days of e-commerce, and while we managed to attract customers and our startup was even profiled in the New York Times, we soon encountered operational challenges and eventually shut down the business. The idea itself was sound; Diapers.com launched by two Wharton MBA students five years later, had a similar focus but a better outcome (acquired by Amazon). We were perhaps a bit early. More importantly, as first-time entrepreneurs, we erred by not surrounding ourselves with great advisors who could guide us through the journey. And to be honest, I wasn’t sufficiently committed to stick it out long enough for the venture to make it.

My next major venture, Yodle, was founded in 2005 with some brilliant undergrads at Penn. The startup did incredibly well and we managed advertising for nearly 40,000 SMBs by the time of our acquisition in 2016. I was active during the first five years having built our core ML and optimization algorithms for bidding and keyword generation. Key to our early success was assembling the right founding team: a founder, Nate, with relentless hustle and intimate knowledge of customer needs (his dad ran an SMB), a strong data-science-based product moat (which I ran), and exceptionally talented early salespeople. I recollect my first meeting with cofounder Ben, our first salesperson. He was probably around 20 years old then but looked more like 15. I doubted someone who looked so young could do B2B sales but Ben turned out to be one of the best salespersons I have met. Sometimes, magic happens when the right people serendipitously run into each other. Our CEO went on to build a great sales and BD org. But an important driver of success wasn’t something we did but simply that the market opportunity and our timing were just right. SMBs were moving their ad budgets from Yellow Pages to online at a rapid rate. We didn’t need to be perfect. We had to ensure that we were among the top 3 players in a fast-growing space. The rising tide would lift all boats including ours.

With Jumpcut, I hadn’t chosen the problem because the market opportunity and growth were right. It was because I was fundamentally excited about making movies and working with creative professionals. I started it to enjoy the process of building a startup and pursue a lifelong desire to make movies. But if my motivation was so pure, why did I feel stressed when things weren’t going as per plan? Along the way, I raised money and hired a team and struggled to hold on to the lightness and joy while meeting the expectations of a venture-funded business. Hence the series of pivots and desperation to find PM fit.

A New Me: The Mindful Entrepreneur

“Pain is inevitable. Suffering is optional.” — Buddhist teaching sometimes attributed to Haruki Murakami

The first few months after the meditation retreat felt like free fall. I felt like I was staring into an abyss with nowhere to go. I couldn’t go back to where I came from, but it was not clear where to go from here. Over time, I began to realize that what I needed to fix wasn’t the operational aspects of my company but the internal dialog. One thing the meditation made clear was that I had ignored – bottled up – a lot of my worries while trying to hunker down and stay focused on the mission. What I was calling (and many of us call) stress was a series of subconscious worries that I was not willing to consciously hear. “We’re the only species who will force ourselves to do something for years that we don’t enjoy by telling ourselves, ‘We have to do this,’” says author Dr. Martha Beck. The other issue was that I was simply not even aware of the internal dialog going on in my head until this meditation. It was through meditation that I learned to tune in and listen to my own self-chatter.

Something else happened. Previously, I’d put up a bold front in front of my employees and investors, worrying that fear can be infectious . That was a big load to carry. I started to be more transparent with my employees. I encouraged them to take on a bigger role in the Org and discover hidden superpowers within themselves. I encouraged my younger cofounder Dilip to be more of a leader. Slowly, things started to feel lighter. Dilip developed a prototype of Scriptsense, our AI tool to help Producers and agents process the massive volume of screenplays coming in (that were often lying in the unread pile). After a brief experiment to bring in an outside CEO, I returned to an active leadership role at the company. This time, I had all the tough conversations I needed to have – with myself, with investors, employees, and partners. We soon found product-market fit and started hearing from many of our users how our tool was like a godsend to them. The startup recently got acquired by another player in the space. It was not a massive financial outcome. But the story of a startup is multidimensional. We landed the plane in the middle of a storm. We built a great product that was not only considered best in class but was also the first AI product to find meaningful adoption in Hollywood, an industry that is slow to embrace tech. In 2024, the tool processed nearly 10,000 scripts for over 400 companies in the industry.

But most of all, the greatest personal growth was that I met many of my fears and worries. Initially, I wasn't even aware of them. Then, when I met them during Vipassana, I was afraid of the fear itself (“anxiety about anxiety” is a thing). Tbh, I wanted to run away from them, and briefly I did. Next I learned to recognize they were toothless tigers. And after being patient with them, I found a way to hug them, learn from them, and grow as a founder and as a person. So, whatever my next adventure is, it will be about discovering new fears and self-defeating beliefs and finding ways to grow.

Ultimately, the biggest battles are not the ones we fight on the outside. The battle is always within.

PS: Some people have emailed me and asked about meditation and Vipassana. Meditation is a great tool to cultivate presence and manage mental clutter. If you are in a high stress job (or otherwise), I highly recommend it (and other mindfulness practices). That said, Vipassana is extremely intense for most people. In fact, I have since been informed that it’s not a good idea when one is under a lot of stress. My analogy is it’s like an ultra-marathon. You don’t want to try it without sufficient training.