Tips From The Top: One On One With Rob LoCascio

I spoke to Rob LoCascio, founder and CEO of LivePerson, about his journey and best advice

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Adam: Thanks again for taking the time to share your story and your advice. First things first, though, I am sure readers would love to learn more about you. What is something about you that would surprise people?                 

Rob: I started LivePerson after my first company went under in November of 1995. I moved to New York City, with a U-Haul containing a couch, a little desk, my computer, and some clothes. I didn’t have the money to have both an office and an apartment, so I sublet a small office and I basically lived there and worked there. There was no shower or anything, so I got a health club membership at New York Sports Club so I could shower there. The beginnings of founding a public company aren’t always as glamorous as they might seem!

Adam: ​How did you get here? ​What experiences, failures, setbacks or challenges have been most instrumental to your growth?                                              

Rob: I come from a long line of entrepreneurs. My grandparents, who came from Sicily, my dad, my sister, they all started their own small businesses. I originally took a different tack and started off working for someone else while I was in college, but there was a recession going on and I was fired via fax machine. It was then that I decided I would never work for anyone again, so I started my first company building interactive kiosks for college campuses. 

I learned from my father, who would build a company and rip it down every few years to build a new one, that the stress of being a serial entrepreneur would take a toll. He had a heart attack in his 50’s, and the impact on the family because of the ups and downs was pretty severe. It left me with the impression that if I could focus and build something over time, that would be the real entrepreneurial challenge, and I’ve been working on LivePerson’s success for 25 years.

Between showering at the gym and ringing the bell at NASDAQ, there were a lot of ups and downs, and they continue even as the company continues to grow. I’ve hit many bottoms building this company over 25 years. Some have been public, because I’m running a public company, but I always look at the winding road as a great challenge. Leaders go into the forest, go into uncertainty and try to create something new in the world. 

Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?             

Rob: When I think of my heroes, I think about my grandfather and my father: people that I admire because of what they built even though it was hard. They had nothing when they built their companies. Unfortunately, my grandfather had to shut his business down during the war. He had been making handbags but never opened the business up again. He taught me a valuable lesson: he made it to the age of 106 but every day he used to say, “Oh, I could have been Gucci. I could have been so-and-so.” The lesson he taught me was that you really shouldn’t quit. And when I think of one of the main mantras in my life, it’s that, never quit. 

Leaders can get to the next level by realizing that failure, or things not going right, is really an opportunity to learn lessons. You can either sit there and wallow in why things aren’t happening, or you can basically just embrace it. That’s when you open up and learn. When we’re doing our best and we’re at the top, we rarely are in a learning process. 

Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders?     

Rob: First: always tell the truth. Many years ago, my chief financial officer and I presented our board with a restructuring plan that would, among many things, see 75% of our staff let go. Bob Matschullat, who was on our board and would later serve on the boards of Disney, Visa, and Clorox, pulled us aside and shared this advice. “You’re young and you have a long career ahead of you regardless of LivePerson’s trajectory. Just tell everyone the truth, don’t bullsh*t them,” he said. Telling the truth is really difficult when you are standing in front of employees and telling them that their jobs are gone. But the truth earns you respect and credibility. It’s the reason why I’m still at the helm of the company in good times and bad.

Second: it’s a tall order to consistently try to better yourself while running a company or project, but it’s always worth it. This manifests differently for everyone, but it’s the greatest challenge that I find and that’s what excites me about it.

Third: take off the glasses. I was pretty much in the dumps when I lost my first company. I remember I saw a psychologist at the time, and every week we talked about the company and my life and family, just went through everything. And then one day he said, “Think of it this way, you’ve got a set of glasses on.” He said, “You have these glasses that were put on you, and you don’t even know you have them. And the way you’re perceiving the world is not serving you for your dream.” 

Adam: How can leaders drive innovation and disruption?

Rob: One of the things I’m most proud about at LivePerson is that, our culture, there’s really an entrepreneurial spirit, even at our size of about 1,300 employees today. We’re trying to break the rules all the time. When you build a culture, it’s never perfected. Your principles and how you live them are constantly evolving, but there are usually one or two that just have to be there, and if somebody breaks those, it’s a non-starter. So figuring out the culture that works for a group of people across different cultures, across different time zones, and unifies them is the way to move forward. We work at it every day to try to get it as close to perfect as it can be while staying true to those must-haves.

Adam: What is your best advice on building, leading and managing teams? 

Rob: One of the things that COVID has reminded me of is that we have to lead through empathy. When you’re going through difficult times in the macroenvironment like we have with COVID, the financial crisis, 9/11, and others, you learn that people all experience them very differently than you might. Empathy is all about trying to understand how others are being impacted. You have to be open to leading people who are affected in different ways than you and need different things to work through them and come out more resilient.

Adam: What is the single best piece of advice you have ever received? 

Rob: When I was sleeping on the couch in my small little office when I got started, the psychologist I mentioned told me, “Do yourself a favor. Go down and give. Even though you’re sleeping on the couch, and you’re eating ramen noodles, and you can’t shower at home. Give. Give back. There are people far less fortunate.”

So I used to help the people in the homeless shelter at St. Bart’s on Park Avenue. People would come in at night, and we’d feed them. And I got to hear their stories. And a lot of them, they just didn’t have the safety net that I did. Today, I try to keep giving back through programs I founded like FeedingNYC, which gives thousands of Thanksgiving meals to families in need every year.

Adam: ​What is one thing everyone should be doing to pay it forward? 

Rob: Remember that the impact you have on one person gets multiplied. When I started FeedingNYC after 9/11, we started small. We had about 40 employees in New York, and I told one of them, “I’m going to go deliver a couple of turkeys. I’m going to go to the supermarket, and pick up all the trimming and stuff and deliver it.” A bunch of people from the company said, “Count me in.” We ended up going to a shelter run by Women in Need, a phenomenal organization in New York for women that have been in bad relationships who can go with their kids to their shelters.

At one of the last doors I knocked on in the shelter we visited, which was called Jenny Clark, a little kid opened the door. He was about six- or seven-years-old. He looked up and said, “Are you a good person or a bad person?” True story. And I said, “No, I’m here to bring a turkey dinner for you.” His sister came out, and then the mother, who was in the bathroom, opened the bathroom door. She saw an adult male with her children, and she probably been through a very, very difficult situation with men to be at the shelter.

She bee-lined toward me to get me away from her kids, but when she realized what I was doing there, she stopped and looked me in the face, and she started to cry. Then she just hugged me. The hardest hug I remember. She said, “I thought people had forgotten about us.” 

I remember I walked out visibly changed. Funny enough, a woman who sold us the turkeys from a distributor up in the Bronx was there with us. I couldn’t figure out why, but she had come with us to deliver the food. I told her the story, and she said to me, “I used to live in this shelter. I lived in Jenny Clark.” And from that point forward, we’ve fed about 80,000 families. You start small, but when you do what you can, paying it forward just grows and grows.

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