Chasing the American Dream in Silicon Valley
“I don’t recommend the path I took,” I tell a small group of high school seniors that I am mentoring in Oakland. After telling them what that path was, most of them agree.
In 2004 I dropped out of College. My father, an immigrant from India, would never get to see me accomplish much of anything, unfortunately. In 2007 he had a sudden heart attack and passed away at the age of 58. This would affect me in ways that I would only begin to discover nearly a decade later. This has been a major driver in my career, in ways that I can’t properly articulate. He went to the Indian Institute of Technology (IIT), a school in Bombay that’s considered more competitive than Harvard or MIT. He then immigrated to the U.S. to get his Masters at UC Davis, and his MBA from Northwestern. My mother received her PhD from the University of Chicago. My sister graduated from Reed College in Portland. Interestingly, Reed is where Steve Jobs dropped out before starting Apple. Perhaps, I wasn’t sure if I could live up to the academic standards my entire family had achieved. I think it was something deeper though. It’s clear now, that when I’m passionate about something; I give everything to it. I wasn’t passionate about academia or proving myself to others back then. But I was hungry to learn, and I read many books outside of my course curriculum during this time, from Seneca to the Complete Works of William Shakespeare to Foucault to Joyce. I was and still am a very curious person, and wanted to consume and learn from as many different perspectives as I could discover.
My strongest memory with my dad was watching David Letterman and Johnny Carson on the couch with him. I remember being young and he would laugh loudly at the monologues. That hearty dad-laugh. To this day they are still some of my heroes for being able to make him laugh like that. Letterman would be on, and I’d just watch my dad the whole time. I liked his laugh and I remember enjoying listening to Carson & Letterman tell jokes and I would watch my dad react to them. I never felt terribly close to my father, but in those moments it felt like I understood him best.
To pay the bills and tuition in college, I was working at AutoTrader, a subsidiary of Cox Publications, and balancing that with school. My mother was (and still is) a professor at the same University that I dropped out of, so it wasn’t a popular decision. (Although, I’m fortunate that she’s always been wonderful and encouraging). I really had no direction at the time, but I had a plan to correct this. I would go camping in Alaska, and if I could find a job on a commercial fishing boat I would pursue that until I figured out what my calling was. This would turn out to be one of the best decisions I ever made in my life. It was the first time I had ever challenged myself aggressively.
“Some years ago — never mind how long precisely — having little or no money in my purse, and nothing in particular to interest me on shore, I thought I’d sail about a little and explore the watery part of the world.” -Hemingway
I found a job in the Aleutian Islands- Kodiak Alaska, on a boat called the Alaska Spirit, and that spurred my early career as a commercial fisherman. I fished salmon, halibut, cod and crab- both snow crab and king, on several different boats over the course of 6 years. It was dangerous. It was hard work. It was risky and uncertain, I got very little sleep, and I fell in love with every aspect of these adventures. However, it was stressful. I’ve seen a man’s arm fall off in front of my from the tension of a taught rope, a man on my boat lost his life once and I’ve fractured two bones.
This experience prepared me to manage stress & hard work very efficiently, and this translated well in the fast-moving and volatile world of tech and startups. Looking back, I think the bridge into tech was this… after coming home from a lucrative crab fishing trip, I heard about an upcoming piece of hardware that Apple was releasing called the Iphone. I was interested enough to pre-order it, and the day it was available in June 2007, I held it in my hand for the first time it was ever released to the world. I remember it quite vividly, examining it; speechless. “This tool is going to change everything about the world” was my very first thought. That day, in 2007, I put my entire savings account, all my crab fishing money, (about $48,000) into Apple stock and didn’t sell a single share until 2014. That was my first significant interaction with the tech industry and it was rewarding.
Crab fishing in the Bering Sea. Sleep = Ø.
I’ll fast forward to where I am now. The last 13 years or so have been a blur of being one of the early employees of Groupon, the fastest growing company of all time and experiencing an IPO. To being one of the first employees of Leadpages (Now Drip.com), a hyper-growth startup which in 2015 we were told was the 3rd fastest growing software company in the US, behind Zenefits and Slack. I was recruited out of Drip by HubSpot, where I currently work.
The interview at HubSpot was memorable. They flew me to Boston, I had several back to back interviews, and really liked everyone I met. At the end of it all my hiring manager kind of fell silent. I said, “I feel like that went really well, yet, I sense some hesitation. Let’s talk about it.” The interviewer glanced down to my hands which were poking out of my blazer, which happen to be tattooed with memories of Alaskan fishing trips, and said “well… I guess I wonder how people would perceive you.” TBH, I really respected and appreciated the transparency here. Most people would not want to address this, and I could see he was also gauging how I would reply. I assured him that I’d been doing this for a long time, successfully, and it even helps to put people at ease in meetings, open up conversations which ultimately I assist to build better and more authentic relationships. When I arrived back home from Boston, I had an offer letter in my inbox. 6 months later he would tell me that my ability to perceive that hesitation and address it, really impressed him. I too was impressed with his question and openness.
I couldn’t be happier professionally, working in Platform Partnerships & Strategy. Although I will say, it’s harder work than crab fishing. You’re challenged in new ways every day. Mentally vs physically. Our CEO at HubSpot urged me to challenge everything that I was doing and ask myself “what would Steve Jobs do if he were running the show here?” Asking this question forced me to think against the normative grain, and 10, 20 years into the future, and above all, with the end user in mind. The world of tech and crab fishing are strangely similar. You have to move quickly and cautiously at the same time. If you fall asleep at the wheel or you aren’t paying attention or get too complacent, you will likely sink the ship and perish.
Strangely, I look at the last two CEOs I’ve worked for as something close to father figures. I want to have pride with them in ways I never could with my dad. I don’t need praise or recognition from them, but I know I will not fail them, and I will work hard to ensure that.
The fun part about “risk” is learning how to mitigate and control it, and turning that into an opportunity. The biggest risk for many venture capitalists and investors is not that they will make a bad investment but that they’ll miss out on a great one.
HubSpot going public, graciously, provided me the opportunity to mentor and invest in founders. This has been one of the most rewarding experiences that this life has taken me into. It’s risky, yes, but startup risk doesn’t scare me much anymore. Risk is an opportunity to succeed. Or. Learn, pivot and do better.
Current Portfolio:
The Light Phone, Coda.io, Directly.com, Sunsama, Drip.com, Typeform, Verblio.com.
