313: Surviving a Failing Startup and Thriving in the Midst of Crisis, With Rippling Founder Parker Conrad

Parker Conrad is no stranger to hard times. His first startup, Wikinvest, failed to take off during the seven years he was with the company. He then had a falling out with his co-founder, which caused him to leave and start over. Conrad’s next venture, Zenefits, faced scrutiny while he served as the CEO. And now, his current company Rippling is feeling the effects of the Covid-19 pandemic. But Conrad’s strength has always been approaching problems with a realistic and humble attitude. Despite the fact that Rippling’s existing customer base has shrunk since the pandemic hit, the company's top-of-funnel performance hasn’t been impacted. They’re setting up record numbers of demos and doubling down on product investment. Most importantly, Conrad is being strategic about finances and still has three years of runway left. In this podcast episode, Conrad shares his most honest thoughts on the challenges of Covid-19, what he’s been doing to get through this transition, and what he thinks other struggling founders should do. If there’s any other type of content you’d like to see that would be valuable to you during this time, please don’t hesitate to reach out at [email protected]. Key Takeaways Conrad’s most challenging chapter as an entrepreneur of a failing startup, and why he chose to stay for seven years The pain point that inspired the idea for Zenefits How Rippling provides an employee system that goes beyond HR How the pandemic impacted Rippling’s existing customer base Why Conrad is focused on burn, and what he’s doing to maintain runway The importance of acknowledging what’s not working while also looking toward a more promising future Why Conrad hates working from home, and how he got through the difficult transition Conrad’s unpopular advice for struggling founders