When should you quit your job to pursue a startup? [EVENT]

Note to entrepreneurs on their first venture: get ready to lose the money you raised from your friends and family.

That was one piece advice offered by the panel of four entrepreneurs at the Philly Startup Leaders University event at Venturef0rth focused on when you should “take the plunge” and pursue your startup idea. Nearly every founder — Vuzit’s Chris Cera, DuckDuckGo’s Gabe Weinberg, RJMetrics’ Robert Moore — said he blew through the friends and family money he had raised for his first venture. (SnipSnap founder Ted Mann managed to avoid this situation.)

Maybe it’s just par for the course.

Failure, the founders agreed, certainly is. That, and the ability to bounce back. Like Cera did, after he had three meetings with First Round Capital and still didn’t receive any funding. Or Weinberg, who took his first venture’s failure pretty hard.

“Honestly,” he said, “I hadn’t ever failed at anything in my life and I was upset about it.”

You have to internalize that failure will happen, he said.

As for Moore, he admitted to drawing out his first venture’s failure.

Three years into RJMetrics, he said, he was still making his business manager send out $17 checks to clients of his initial business, an affiliate marketing venture.  He was afraid that if he shut the company down, there would be public outcry. Finally, he said, he came to his senses and shut the business down — and no one cared.

So what does it take to quit your job and take the path of entrepreneurship? Here are three tips from the founders.

• It helps to have “delusional confidence,” which Weinberg said he had, believing fully in his first venture from the first day he started it. Each of the founders agreed that confidence was an important trait to have for entrepreneurs looking to take the plunge.
• …or an accommodating boss: When Moore told his boss at New York City-based venture capital firm Insight Venture Partners that he wanted to quit in order to pursue a startup, his boss said he’d keep him on the payroll while Moore figured things out. Only catch was, he wouldn’t get a bonus that year.
• …or an accelerator: Mann quit his job exactly two years ago to found SnipSnap, and it helped that he had been accepted into DreamIt Ventures to develop his idea further.