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How Entrepreneurial Spirit and A.I. Helped LivePerson Bounce Back From Disaster

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Building a business is a path fraught with difficult decisions. For every hard-won success, there are equally hard-learned lessons. Fred Smith gambled FedEx’s last $5,000 to save the business, Henry Ford went through two bankruptcies before founding Ford Motor Company and for Rob LoCascio, the CEO of LivePerson, survival meant he had to do the unthinkable and cut two-thirds of his workforce just one year after taking the company public. He is the original bounce-back guy, having survived three major world disruptions: the dot-com bubble, the credit crunch, and now, the pandemic.

On this episode on Business X factors, LoCascio lets us ride shotgun on his journey, and he explains how LivePerson has been able to not only bounce back and become a massively profitable business, but how they have been able to revolutionize consumer communication with brands. He reveals his and his company’s  X factor and he looks toward the future of business and technology.

Main Takeaways

  • Hit the Brakes and Make a Turn: There are many entrepreneurs who hang on to their original idea long past its expiration date. It takes foresight and a good reading of the market to abandon an idea. But this tough step is necessary in order to move onto the next thing. Have a short memory and your eyes pointed ever forward, and don’t be afraid to make the hard decisions.
  • Get it Out: Whether you’re ready or not, sometimes you just have to get a product out to the market and iron out the kins later. In fact, by getting the product into the hands of the user, you are better able to understand exactly where improvements are needed and can then make adjustments with velocity.
  • A Different Point of View: Leadership is always one of the most important elements in the success of a company. As such, it’s easy to play it safe when hiring for key roles. But sometimes it’s useful to bring in a new perspective or a different kind of person for a role like CFO. When someone with a background counter to what is traditional is put into a role, that person can ignite a new spirit of innovation and bring new ways of looking at things that can spark growth in a company.

Key Quotes

I made a decision to restructure the company to get profitable. And that meant laying off 140 of 180 people. So firing 70% of your company in a day. I’ve never done that in my entire life, but I dealt with reality… The internet was collapsing, and we needed to just stay alive. So, I made a conscious decision to stay alive… and we cut our earnings in half as a public company. We said, we’re going to spend half our cash flow and shareholders didn’t like it and we went into a deep winter and everything would look bad from the outside, but inside we felt like we were really making progress, and today we’re a better company for it.”

“Bob Matshullat said, ‘He said just don’t bullshit them. Tell them the truth… People are going to look at you and they’re going to remember you for what you say and if you bullshit them, that’s what they’re gonna remember. So just tell them the straight scoop.”

“People say, when they come here, it feels like a start-up, but we’re not a start-up. We’re a public company. We have close to half a billion in revenues and almost a $4 billion market cap and it’s not a start-up anymore. But people feel that energy of the company is about being an entrepreneur. And, even though you’re working in a company and you didn’t start it, you can be an entrepreneur here.”

“We bought a number of businesses over the years and the entrepreneurs have stayed. I’m really proud of that. A lot of them have stayed. I mean, we must have about seven or eight of them in the company today and they’re running different businesses. They’re doing something because they can still flex the muscle. They have resources and can go after big, big ideas without raising venture capital and worry about raising money and all that.”

“Conversational commerce allows you to ask a question and get back that response, ask a follow-up and get back a response. So, you’re getting true personalization by using the conversational user experience. And that’s where the future’s going. My kids, their user experience is not going to be a website and app. They’re just going to talk it out… there’s a lot to happen to make that happen at that scale, but that’s the path we’re on.”

“The world I envision is a world in which primarily the machines are powering the conversations you’re having with brands and not humans because consumers don’t really want to be put on hold. They just want to have the information and want to connect with the brand. They want to buy things and, and we allow them to create this very personalized feeling by doing that over a messaging AI framework.”


Rob LoCascio is one of the longest-standing tech founders & CEOs, acting as the guiding force behind LivePerson (LPSN), a multibillion-dollar Conversational AI company that makes it easy for consumers to ask questions & make purchases in the messaging channels they use every day.

A visionary, inventor & disruptive leader, Rob’s grit & determination is how the company has survived & thrived for 25+ years, now with 18,000+ customers & 1,200+ employees. His mission is to share his successes, failures & learnings on his entrepreneurial journey to encourage those at any stage in the process.

Outside of business, Rob is a founding member of the NYC Entrepreneurs Council, as well as EqualAI, which fights bias in artificial intelligence. He started the Dream Big Foundation, which runs FeedingNYC, giving families in need Thanksgiving dinners & providing over 85,000 meals to date, & the Dream Big Entrepreneurship Initiative, which funds, mentors & empowers entrepreneurs in underserved communities. Rob also hosts a weekly podcast, ‘Over the Wall’ where he “shares his journey, invites industry titans to discuss their biggest mistakes and lessons learned and help real entrepreneurs work through challenges big and small.”

Business X factors is produced by Mission.org and brought to you by Hyland.

For over a decade, Hyland has been named a Leader in the Gartner Magic Quadrant for Content Services Platforms, leading the way to help people get the information they need when and where they need it. More than half of 2019 Fortune 100 companies rely on Hyland to help them create more meaningful connections with the people they serve. When your focus is on the people you serve, Hyland stands behind you. Hyland is your X factor for better performance. Go to Hyland.com/insights to learn more.

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