Lead Your Life: hustle, failure, and purpose
Rob LoCascio started LivePerson by sleeping on an office couch and now, 28 years and two new startups later, we get into failure, purpose, and leading your life.
Rob started LivePerson after a previous company failed, putting 50 grand on credit cards and then landing in New York City. Instead of an apartment, he rented a small office space and lived there for two years, sleeping on an Ikea couch and showering at a health club. He lived on about 500 dollars a month. When the company went public, the auditors flagged his personal expenses as an anomaly. And yes, he still has the couch.
While he was living on that couch, a therapist told him to go volunteer at a homeless shelter. It was a move that gave him perspective. Seeing people who didn't have a family safety net or even a couch made him realize he was lucky. He says he has a genetic disposition to not quit, but he also believes that anyone has grit in them if you put them in an unsafe environment. The challenges, he says, are gifts.
After 28 years running LivePerson, he now has two new AI startups. The mission is to build products that create human connection, not addiction. He tells a story about his seven year old son scrolling on an iPad at three in the morning like an addict. He sees his new work as an opportunity to build a different kind of world, one with small AI models that people own themselves, instead of big tech models that make us feel dumb.
“Whatever life you're leading you just got to lead it. Not follow it, lead it.”
Notes
- For the first two years of LivePerson, he slept on an Ikea couch in the office and lived on about $500 a month.
- His therapist advised him to volunteer at a homeless shelter while he was living on the couch.
- After 28 years, he left LivePerson and started two new AI companies, Kid and Uare.
- He believes the two deadliest things for founders are the need for certainty and control.