Guests: Parker Conrad, CEO of Rippling, and Mamoon Hamid, partner at Kleiner Perkins

How long did it take for Parker Conrad to stop wanting revenge? “I’ll let you know when it switches over,” the Rippling CEO and co-founder jokes. He resigned from his last company, the buzzy HR unicorn Zenefits, in 2016 and then quickly realized that the company’s new leaders would never return it to its former glory. He still loved the problems he had been trying to solve, and launched Rippling because “there was an opportunity there, [and] if it works ... it’s going to be fundamentally and foundationally better as a product.” It worked. As of March, Rippling has been valued at more than $11 billion, more than double Zenefits’ peak.

In this episode, Parker, Mamoon, and Joubin discuss what happened at Zenefits, avoiding press coverage, FOMO and expectations, Paul Graham, fixing corporate insurance, Ryan Peterson’s “revenge portfolio,” CEO coaches, Mike Vernal, approving expenses, anecdata, and the Costco of SaaS.

In this episode, we cover:

How Parker and Mamoon met (00:56)
The Zenefits Series B (06:29)
“Stuck in a nightmare” (09:20)
Entrepreneurship is “soul-destroying” (12:46)
Parker’s first company, SigFig (17:17)
Starting a company for the right reasons (21:02)
Starting over after Zenefits (27:06)
Avenging Zenefits (31:57)
Rippling’s unusual Series A (38:40)
What it does well (43:13)
“Go and see” (46:35)
The compound startup (51:44)
Who Rippling is hiring and what “grit” means to Parker (01:00:39)

Links:

#162 CEO and Co-Founder Rippling, Parker Conrad w/ Mamoon Hamid: Compounding

Grit