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 the University of Minnesota. My father never got to see me do 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 may not be able to properly articulate until I’m much older and wiser. He went to the Indian Institute of Technology (IIT), a school in New Delhi 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 of. 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. My thesis is that when I’m passionate about something, I give everything to it. I wasn’t passionate about academia. (Although, I am currently taking courses at Stanford’s business school and really enjoying it this time around). Back then though, I was hungry to learn and I read many books outside of my course curriculum during this time, such as Seneca’s “On The Shortness Of Life,” Plutarch’s “Lives,” “Walden” and the Complete Works of William Shakespeare. In fact, I did not read any of my course curriculum, which was a major contributor to my failure as a student, obviously.

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 me they were magicians for being able to make him do that, and I admired them greatly. 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 I understood him best.

To pay the bills 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.” -Ishmael

I found a job on the Aleutian Islands in Kodiak, AK on a boat called the Alaska Spirit, and that spurred my career as a commercial fisherman. I fished salmon, halibut, cod and crab- both opelio and king, on several different boats over the course of many years. Yes, it was dangerous. Yes it was hard. It was risky and uncertain, I got very little sleep and I fell in love with it.

Everything I just said in the last sentence prepared me for the world of tech and startups, and that’s what would eventually bring me to San Francisco. Looking back I think the bridge was this… after coming home from a particularly lucrative crab fishing trip, I read about the iPhone. The very first one wasn’t available yet. I pre-ordered it, and held it in my hand the very first day it was ever released to the world. “This tool is going to change everything” was my very first thought. I remember it so vividly, absorbed by it all, from the features to the applications, the perfect design… and the potential of it. That day, in 2007, I put my entire savings account ($48,000) into Apple stock and didn’t sell a single share until 2014. That was my first significant interaction with “tech.”

Crab fishing in the Bering Sea. I slept about 4 hours every 48–72 hours.

I’ll fast forward to where I am now. The last 8 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, 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 Leadpages 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. HubSpot is an incredible company (we’re hiring). At the end of it all 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.” Now, 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 partnerships. 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, although I will say, it’s harder work than crab fishing. You’re challenged in new ways everyday. Mentally vs physically. Our CEO urges us to challenge everything that we’re doing and ask ourselves “what would Steve Jobs do if he were running the show here?” Asking this question forces you to think against the normative grain, and 10, 20 years out into the future, and to always solve for the user. The world of tech and crab fishing are so 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, you will likely sink the ship and perish.

Strangely, I look at the last two CEOs I’ve worked with 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.

In tech, I like to win, and I like to pick winners. In 2017, I participated in my first two angel investments. In startups Sunsama and Kylie.ai. In the fall of 2016, I put more money than I could afford into an investment in Ethereum, a crypto currency like Bitcoin that I believe has incredible potential and will explode. (Not investing in it now would be like not investing in Jobs/Woz when they were in a garage. Shake my hand in 10 years… or punch me). Ethereum is primed as a platform for “smart contracts” but I believe it could also disrupt the way we transact within peer to peer networks like Uber, Airbnb etc. It’s a big, “risky” bet, and I’m basically all-in with ~1160 coins. The fun part about “risk” is learning how to mitigate and control it, and turn that into an opportunity.

The biggest risk for real venture capitalists and investors is not that they will make a bad investment but that they’ll miss out on a great one.

There are a lot of big time VCs and angels in San Francisco, whom I’ll never stack up next to, but I am making “sacrifices” to earn my way into these circles. I live in SF’s Tenderloin district (a notoriously gritty part of the city) in a small studio apartment. I’m not complaining at all about this. I’m not struggling, and I have a roof over my head. No complaints whatsoever. What I mean by “sacrifice,” is that I choose to not indulge in lavishness, and prefer the excitement of investing my earnings into calculated risk. That’s what I came here to do. This is the American dream in Silicon Valley.