Those Tuesday evening sessions quickly became my favorite part of the week. It was like being back in college and attending philosophy class. And Rasanath had a wealth of knowledge about the scriptures which meant that so many of my previously unanswered questions about spirituality could be discussed. While visiting our apartment every week, he also watched our startup idea unfold (my cofounder, my wife and I were all living together at the time)…an online marketplace where people could discover, book and host unique experiences. And when we were preparing to launch, we persuaded Rasanath to be the first Sidetour host — Dinner with an Investment Banker-Turned-Monk at an East Village Monastery. That title sparked a curiosity in everyone (including our colleague Michael), and people loved the experience (it became the most popular experience on our platform with a 500-person waitlist). Our lives became further intertwined a couple of years later as Rasanath and Hari Prasada invited me to join Upbuild’s advisory board.

In 2013 I took Upbuild’s flagship workshop Excavating Your Ego on the Enneagram personality framework and the ego, and I now think about my understanding of myself in a pre-Enneagram / post-Enneagram way. My whole life came into stark relief that weekend as I realized how many of my choices (Harvard, McKinsey, MTV, starting a tech company) were driven by my desire to have other people think highly of me. I hadn’t realized that I had been painstakingly crafting an image for more than 35 years and I didn’t even know what I myself wanted…what were my own dreams separate from what everyone else would clap for? Of course, that weekend was just the beginning of a long journey of self-understanding and exploration.  

Sidetour was ultimately acquired by another company and after two years my cofounders and I left to start something new, but after more than six months of ideation all I could think about wanting to do was to help Rasanath and Hari Prasada reach more people and impact them in the way I had been impacted by their work. After months of struggling with questions such as “What about my identity as a startup founder and everything I had invested in to get me to this point? Am I squandering my fancy degrees that are really tickets to economic wellbeing? Will people think I’m going into HR? Do I want to be a coach or a player?” (clearly I was still living securely in the prison of my ego), I finally built up enough courage to take the leap regardless of what others (and mostly I myself) might think or say. And fortunately for me, Rasanath and Hari Prasada welcomed me with open arms when I declared that I wanted to work with them full-time.

I joined Upbuild with the intention of devoting the rest of my life to working together, AND I explicitly gave myself six months to prove to myself that it would be financially sustainable, fulfilling, and a fertile environment for my growth. Within a few months I knew that this was the work I was meant to be doing. The conversations I was getting to have about inspiring people, working through insecurities, mediating conflict, navigating careers, building healthy cultures, and becoming a leader were the conversations I was always most drawn to; now, instead of just a part of my work, it had become all of my work. And even more than that, our work is focused on the mission of self-realization, and what could be more important than that? Associating with Rasanath and Hari Prasada everyday was also changing me and bringing me closer to the person I aspired to become.

In a way, I had gotten here by accident. Except that there are no accidents :-). This is work I’ve been doing and preparing for (and secretly longing for) my whole life…I just didn’t realize it until I got here.