How a former Y Combinator partner decided to drop out of law school

“It’s easy to avoid taking
the leap or doing something because you just have this gut-level
feel of ‘it’s too risky for me to do,'” says Harj Taggar,
pictured.
Courtesy of Harj
Taggar

• Harj Taggar is a former Y
  Combinator partner and the cofounder and CEO of
  Triplebyte.
• He was initially enrolled in law school in the UK, but
  he dropped out to move to the US and start a company.
• Taggar decided to leave law school by getting specific
  about the risks. It’s a strategy he recommends to young
  professionals and aspiring entrepreneurs today.

A decade ago, Harj Taggar couldn’t have predicted what his career
would look like today.

Taggar, a former partner at the startup accelerator Y Combinator,
is the cofounder and CEO of Triplebyte, a recruiting and
technical screening platform for tech companies. Back then, he
was a law student in the United Kingdom.

He had an idea for a business, and was considering moving to
Silicon Valley to pursue it. But the prospect of dropping out of
law school was intimidating.

So Taggar evaluated his options using a simple strategy that he
still uses and recommends to young professionals today: He got as
specific as possible about the risks of dropping out.

Taggar told Business Insider, “What I pushed myself on was, ‘OK,
what is the big risk here?'”

At the time, he said, he had no real expenses — and also minimal
savings. He remembers thinking, “The worst-case scenario here is,
I work on a startup, it doesn’t go anywhere, and 12 months later,
I re-enroll in law school.”

Suddenly, that worst-case scenario didn’t seem so scary after
all. He left law school and moved to the US to work on his
startup, Auctomatic, an auction and marketplace management system
for sellers.

Soon after, Taggar was accepted into Y Combinator, and his
startup received investments from Paul Buchheit, the lead
developer of Gmail, as well as the venture capitalists Paul
Graham and Chris Sacca. (The business has since shut down.)

A few years later, Taggar became a venture partner at Y
Combinator, which in the past decade has launched startups
including Airbnb, Dropbox, and Instacart.

It’s OK if you decide not to take the risk — as long as you know
exactly why

“It’s easy to avoid taking the leap or doing something because
you just have this gut-level feel of ‘it’s too risky for me to
do,'” Taggar said. He said he tells people, “If they have enough
curiosity to consider it as an option, but they’re afraid of the
risk factor, then I’d say be specific. What exactly is the risk?”

Say you’re worried about not having an income while you’re
building your startup. Taggar called that “a totally valid
concern,” but added that you can get more specific by asking
yourself, “How long could you go? What would happen if you went
six months without being paid a salary?”

Even if your ultimate answer is “this just isn’t for me,” Taggar
said, that’s OK. Maybe you have a mortgage and a new family and
it’s not the best time to take a risk. The key is to know exactly
why you’re avoiding that jump.

Taggar said, “Often people surprise themselves when they write
things out and are more specific about the risks and how big the
risks actually are for them.”