My Journey



DISCLAIMER: ORIGINAL POST WAS MADE ON AUGUST 19, 2018



Two year ago, I walked into my universities registrars office and withdrew from school. They informed me that I had about two days before they were going to kick me out. I was limited to two days to figure out what I was going to do for the rest of my life. 



At the time, I knew that I loved startups, technology, entrepreneurship, and self-directed learning. I also knew that I needed to be in the epicenter of where innovation was happening.



So I thought to myself, what better place to be in than Silicon Valley?



I then did what any perfectly sane person would do. I went to the Airbnb app and literally found the cheapest place to live in California.



That same day, I booked a one-way ticket to San Jose unbeknownst to what my experience would be like.



I ended up in a “hacker house,” better known by its more formal name, a hostel.



At any given moment, I lived with over five people, and most of us shared the same bathroom.



I didn’t have much money, so I had to budget and spend wisely. This inevitably led to oatmeal, ham sandwiches, and Soylent being my primary source of energy and nutrition.





In addition to this, the hacker home didn’t have reliable air conditioning, so I was forced to open up the window which unfortunately led to a plethora of ants taking over my room.



I’m pretty sure you’re wondering by now why I put myself through all of this.



Well, it just so happens that I moved here to either build a startup or join one.



During this time, I was working on conversational AI startup where people would acquire knowledge in a simple, interactive, and fun way by talking to digital humans that embody the people they love (Steve Jobs, Elon Musk, etc.)



It was apparent to me that I didn’t have adequate computational resources to work on such an ambitious project, plus, the timing wasn’t the best, so I decided to stop working on that idea.



In December, nearing the Christmas holiday, I figured it was time to go home and spend some time with my family back in Washington, DC.



While I was home, I studied machine learning, freelanced a couple AI projects, built a powerful PC, and traded cryptocurrency.



There was one school that I believed would be an ideal fit for me — Stanford — I applied and was rejected.



With my new skills, I decided to apply to some AI fellowships, guess what? I was rejected by all of them. I honestly don't know what I was thinking.



After some self-reflection, I noticed that I had been running in the same place for too long, getting nowhere. I came up with a list of actionable goals and held myself accountable to accomplishing them.



Scrolling through my Twitter timeline, I saw a tweet by a startup COO mentioning a project they wanted to work on and was looking for someone scrappy to help out.



I immediately stopped what I was doing and DM’ed the startup exec.



He asked me a question, was impressed by my answer, then responded with:





I then bought another one-way ticket but this time to San Francisco — the most expensive city in the US.



I knew that San Francisco was a place where I could meet like-minded people and learn from some amazing founders and investors.



So, I texted a friend that I knew lived there and asked if I could crash at his place for about a week and he said “sure.”



After that week was up, I found a hostel to stay in. I couldn’t afford to stay a night anywhere else, so I had to resort to my last option — Couchsurfing.



I stayed at a random woman’s condo for a weekend in SOMA, in exchange for free lodging, I went swing dancing with her.



At one point, I thought I was going to be homeless, living in “The Tenderloin,” so I downloaded the schedule for a free, mobile shower.



Luckily, I found a family friend that lived right over the Bay Bridge in Oakland who welcomed me into her and her husband’s lovely home where I stayed for a couple months, helping out with the plants and chickens.









Throughout this process, I applied to a couple of startup jobs but was extremely picky, I was only looking for companies that met specific criteria (less than 50 people, mission-driven, pre-series A, etc.)



As you can guess, I was rejected by almost all of them. Submitting applications with my resume hoping to land a job was ludicrous considering that I didn’t have a degree or any “real” experience.



I changed my strategy, instead of applying for jobs the conventional way, I became a trailblazer and carved my own path.



I reached out to startup founders via email and Twitter and pitched them on how I could add value to their company. 



This landed me a couple coffee shop meetings and some onsite interviews but nothing stuck. One founder even told me “you’re too risky, we’re an early-stage startup we already have enough risk, de-risk yourself.”



By this time, I was reaching my breaking point.



I was contemplating on if I should just give up and go back to school but I knew that didn't necessarily fit my learning style and I quite literally came too far to do that.



A couple of days later, I received a notification on AngelList from a company that I previously applied to.



The CEO asked me to come in for an interview. I went to the HQ, rocked the interview, and was offered a full-time position within the same week.


Some of my learnings so far:



  • Learn to deny immediate short-term gratification in favor of greater long-term gratification

  • Don’t give up easily even if you can’t see the light at the end of the tunnel

  • Sometimes life is about risking everything for a dream no one can see but you

  • Most doors in the world are closed so if you find want you want to get into, you better have an interesting knock

  • If you want results, go straight to the top

  • Know your unique value proposition and communicate that concisely and effectively

  • Every opportunity may not be the right opportunity for you

  • When you’re largely unproven, you may have to create value before you ask for value

Published by DeWayne Roy (wayne) 3 weeks ago on Friday the 3rd of May 2019.

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