My Startup Journey: How I Became the First Hire at a 4-Month Old, Pre-Seed Stage Startup

At the end of 2014, I joined Jopwell, a minority recruitment tech platform that connects Blacks, Latinos and Native Americans to top companies for internships and jobs. I joined the company four months into its establishment as the first official employee, to lead business development. Since my start, I have received many questions from family, friends and even strangers, curious about my decision. Here is my story.

I admit, I wasn’t initially blown away by the idea of Jopwell and the need for a tech solution to diversity. I was a beneficiary of some of the more well-known non profit organizations providing access to educational and professional opportunities for ethnic minorities from underprivileged backgrounds. As far as I knew, there were plenty of existing solutions to America’s diversity problem.

Despite this however, my decision to join the team was very simple. It came down to one thing – the people. At the time, Jopwell consisted of two people and a dog.


Porter – Co-Founder and CEO, Ryan – Co-Founder and President and Max – office pet, all crammed into a 12×6 room in WeWork (shared office space for businesses, usually start-ups) in SoHo. I’ve known Porter since high school. We became fast friends at Lawrenceville when he started as a new boarding student sophomore year. There weren’t very many students of color at the time, so we were happy when new students of color were admitted and quickly grew pretty close trying to navigate the new environment together socially and academically.

During our junior year, a Vice President in Diversity Recruiting at Morgan Stanley launched a program to expose students of color to Wall Street and the world of finance at an early age through an internship. Porter and I were selected to interview and fortunately received the opportunity, at 17, to intern for one of the best banks on the street. One summer, on a bus ride from Morgan Stanley’s Westchester office to its Manhattan headquarters, Porter was bouncing some of his random, eccentric business ideas off of me, as he often did. I would weigh in and attempt to pick them apart for fun. But that day, he definitively put it in the universe. He promised that he would start a company one day. And I promised that if I could, I would help him build it. One day.

I went off to UPenn, continued at Morgan Stanley for 4 summers and eventually started my career in management consulting. He went off to Yale, spent 5 summers at Goldman Sachs and eventually started his career in finance there, selling foreign currencies. We still managed to keep in touch over the years and caught up at a high school reunion event, where he filled me in on his decision to leave Goldman Sachs and on his early progress with getting Jopwell off the ground. Since high school, I had always known Porter as a passionate and determined person who dreams big and gets things done. So when he told me he quit, I knew he wasn’t blindly chasing a lofty dream, but diligently working towards a clear goal.

Coincidentally, I also went to school with Ryan. We were one year apart at UPenn, but we met for the first time in that cozy 12×6 SoHo office. After spending many hours talking to Ryan – getting to know his story, understanding his role in fulfilling the Jopwell vision, understanding how he and Porter were executing on that vision and watching him field tough questions from investors to close Jopwell’s first large round of funding – I knew this was going to be a special team. The unique combination of our personalities, backgrounds and personal experiences made us the right team to tackle America’s diversity recruiting problem at such a critical time in this country’s history. We had all received amazing opportunities through diversity recruiting initiatives and wanted to provide the same access to people who may not have had the same resources that we did.

I am a relatively risk averse person, so before joining an early stage, pre-seed startup it was important for me to have the utmost trust in my teammates’ sheer hustle and leadership abilities. I am a Jamaican immigrant who also coincidentally grew up in South Jamaica Queens, New York before educational opportunities led me to a completely different environment. I have found my way to success in both gritty, resource-strapped environments and in ritzy, opportunity-rich ones despite numerous challenges and failures along the way. As a result of this unique upbringing, I am confident in my ability to succeed, no matter the odds or the playing field. Before diverging from the path I had mapped out for myself in the corporate world, I needed to have the same trust in Porter and Ryan. But observing their interactions, was just icing on the cake. Their natural business acumen, keen salesmanship, unwavering passion and clear vision combined with their scrappy nature reminded me of myself in so many ways. I saw how in sync they were with each other’s thoughts and how they resolved problems when they weren’t so in sync. I saw their individual strengths and weaknesses and how well their strengths complemented each other’s weaknesses. Lastly, I saw how resourceful they were with both their financial and social capital. This gave me all the confidence I needed to ultimately join the pair on the journey to leading Jopwell to success.

Six months in and looking back, I am confident in my decision. Before joining Jopwell, my life experiences have never been more relevant to the work that I do on a daily basis and that is a truly amazing feeling.

Anastacia Gordon is a tech investor, writer, and (former) operator born in Jamaica, but raised in NYC. She’s currently an MBA student at Columbia Business School and spends her time consumed by all things music x media x culture x tech. While in school, she has invested alongside incredible people at Kapor Capital, Cross Culture Ventures, Lerer Hippeau, and Comcast Ventures. Prior to that, she was a founding team member at Jopwell (YC S’15). 

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