The Founders Who Raised Huge Money Easily

It‘s the dream of every startup to have VCs begging to invest, but how these founders did it are important lessons to learn.

Parker Conrad is the founder of Rippling, a startup which is valued at US$11.25 billion. This is his 3rd attempt. When he started his first company back in 2006, it dragged out for what he called “seven years of slow, grinding failure”.

In an interview with Garry Tan, he spoke about how he approached “70 different investors” and everyone turned him down. Eventually he fell out with his co-founder and left the company.

The day he left the company, he also started a new one called Zenefits. This time, he was so disillusioned with fundraising that he decided he wasn’t going to go through it again.

Instead, he would join Y Combinator, “raise a few hundred thousand dollars”, and then use the cash flow from the business to keep going. His goal was just to become “a reasonably successful tech-enabled insurance broker”.

That was September 2012.

Beating the odds as a solo, non-techie founder

Conrad started Zenefits because of his own experience buying health insurance for his new employees in his…