Connect with us


Taking The Leap: What Quitting My Job, Moving, And Going Into Debt Taught Me About Entrepreneurship


I’m sure you’ve heard of being in the right place at the wrong time, but have you ever felt like you were in the wrong place at the right time? 

I have. 

In May 2021, with $15,000 in the bank, I quit my job and moved across the country to pursue my dream.

I had an interview with Y Combinator lined up for my company that would eventually become Sonr. I knew that the acceptance rate for YC interviews was incredibly low—but I couldn’t help but go all in. When I compared following my entrepreneurial passion to continuing to work at a job I didn’t feel nearly the same way about, I quit my job, moved to San Francisco, and planned to figure it out.

It was the first in a series of high-risk decisions that looked scary on paper—but felt right. And ultimately, having gone from $14,000 in debt to raising $5 million for my dream company, the decisions paid off.

But what’s important to understand is that these weren’t complete leaps of faith. They were informed risks based on what I knew about the overlap between my skills, my passions, and the kind of technology the world desperately needed. 

For aspiring entrepreneurs, here’s the sequence of events that lead me to where I am today.

Leaps of faith (and what they taught me)

  • Quitting my job. Before all this started, I was living in Ashburn, Virginia, doing research for a federal government project. I had a lot of security—job safety, a steady paycheck, and things that could lull me into complacency.

    The catalyst for leaving might have been landing the YC interview. But the deeper reason was that I wanted to go from a secure situation to a make-or-break situation. I wanted more skin in the game.

    Key learning: Friends and family want you to be safe and secure, so they’ll probably discourage you from chasing a dream that involves risk. Listen to their voices, but don’t let them be determining factors in how you handle your life.
  • Moving across the country (twice). I moved to San Francisco before the Y Combinator interview—in other words, before I got rejected from YC. Later, I moved to New York City, chasing another incubator, Launch House, which I ultimately got into (more on that in a moment).

    Being in these places without job stability might sound insane. But I was surrounded by other young, hungry entrepreneurs who lived every day with a build mindset. I was in atmospheres that fueled me and had a hugely positive impact on my network.

    Key learning: Live among people who share your dream. Even if there’s no immediate financial return, there is abundant collateral benefit that will pay dividends down the road.
  • Applying to (and getting rejected from) lots of incubators. While in these locations, I continuously applied to incubators. First YC, then Hyper, then Launch House, each of which rejected me (Launch House would accept me in a later round).

    Some people might have gotten discouraged by that series of rejections. But I didn’t view rejections as Ls—I used them to refine my vision and pitch for the business.

    Key learning: The best incubator pitch proved to be the one that didn’t conform to the incubator’s expectations. The best pitch was the one that illustrated the ideal situation for my company. Don’t shape your vision to what the incubator wants; find incubators that can help fulfill your vision.
  • Fundraising before I was ready. In the early days building my company, peers would often urge me to start fundraising. I resisted on the grounds that I “wasn’t ready.”

    A quick story. When I was living in NYC, I heard that a competitor (who raised a round) was hosting an event. So, I went to hear their pitch as a sort of undercover operation. Realizing they closed funding with even less than we had in place was eye-opening and really put things into perspective. What did I learn? You’re never “ready” to start fundraising. If you wait until you’re 100% ready, you’ll wait forever.

    Key learning: Raise funding before you feel “ready.” And for a bonus, don’t think of investors as people whose attention (and capital) you’re lucky to get—think of them as people who would be lucky to get equity in your company.

There were some scary moments along the way for sure. Like when Goldman Sachs called me about my thousands of dollars of debt. But my vision of rebuilding the internet was worth taking on debt. It’s like what Steve Jobs said, “You can’t connect the dots looking forward; you can only connect them looking backwards. Trust that the dots will somehow connect in your future.”

If you know the risks, know your stuff, and you’re willing to embrace some uncertainty—it’s time to jump.

Founder and CEO at Sonr

Top 10

Copyright © 2019