Venture Voice – interviews with entrepreneurs

Entertaining Entrepreneurship

Robert LoCascio of LivePerson

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Born into a family of entrepreneurs, LivePerson founder and CEO Robert LoCascio always had the entrepreneurial spirit, going back to his teens when he and a friend started an auto detailing business. After graduating college, he had a brief stint in a “real” job, but that experience — he ended up getting fired via fax — convinced him that he never wanted to work for someone else again. Determined to control his own destiny, he took out $50,000 on credit cards to fund his first business, IKON. When a customer asked them to build a website, he made a bold decision to shift the business and, in the process, get himself in the mental shape necessary to be the entrepreneur he wanted to be.

In this candid conversation, Robert reveals not just the business side but also the psychological and emotional journey involved with being an entrepreneur. His story is one of many ups and downs — from being hounded by credit card companies to taking his company public just before the dot com bubble burst to narrowly avoiding stock delisting and then ultimately steering his company to its current $3.5 billion value. In some uniquely disruptive times, Robert also hasn’t been afraid to disrupt his own businesses. He believes the doubts and the dark days have something important to teach us, and that’s why he says the biggest lesson all entrepreneurs should take away from his story is this: Never quit when you’re down.


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Highlights from this episode:

“There’s two parts of being an entrepreneur: One is you want to solve a problem that you think exists in the world, like, some problem you faced, and you think, man, I just want to fix that. And the second part is usually you’re like, I want to have a lot of control over my future.”

“When you think about the entrepreneurial personality, it’s probably a pretty high-control personality, which can lead to good behavior and not good behavior, you know. Because that’s the entrepreneurial spirit.”

“Somehow my brain put it all together and said, Why don’t you go after the college campus market? Because I realized I just came out of college, and college advertising was really bad.”

“It just gave me a sense that this was some future.”

“There wasn’t really the concept of venture capital and there was no AWS or anything. You hard-coded and hard-built businesses.”

“I hung up the phone, and I remember thinking, we’re done. Because I’d seen the web. I didn’t really believe in it. I thought digital video and interactive TV would beat it out. But at this point I kind of realized this was the future, like, getting access in a student’s room, versus walking down to a student union building.”

“It was hard, you know, at that point. I wasn’t paying the credit cards, the credit card companies were chasing me around. I didn’t get put into bankruptcy because I didn’t have any assets.”

“I opted for an office over an apartment.”

“I was down in the dumps…I felt like I was a total loser.”

“We felt like we were artists. You know, it wasn’t about technology; it was about the art of the internet.”

“What Frank [his psychologist] made me realize was that the way I was viewing the world was not serving me.”

“When I started the company I was not mentally prepared to do what I needed to do.”

“I’ve done quite well with this business because I always have a sense of uncertainty around, how am I viewing the world? I don’t take for granted that the way I’m viewing things is the right way. I have doubts. So, you know, I have enough doubts. It doesn’t paralyze me…It keeps you in a constant state of learning. It keeps you in a constant state of keeping, like, your ego in check.”

“The skills I need I’ve got to keep developing. I can’t be frozen in time.”

“I started to think deeply about the chat business and building websites, and I knew we couldn’t do both, and I kind of felt like it was a sign…I said, you know what? I don’t want to build websites anymore.”

“I think we had $10 million or $12 million in the bank, so we had six months of cash. So this was not enough room to do anything. So if we weren’t going public, we were having a problem, you know, staying alive.”

“I knew the end was coming.”

“A bubble feeds off itself.”

[On the day LivePerson went public] “I didn’t get to enjoy it.” 

“Even if this doesn’t work out, you’re going to have to have a career and you want people saying, at least he tells the truth.”

“A couple of months later, from our offices, we watched the towers come down.”

“That taught me a lot of lessons which, especially into the days of COVID, about how you manage people and work with people through external macro events.”

“We beat the delisting by, like, literally 2 days.”

“I thought we should do this pivot in strength…let’s go ahead and disrupt ourselves.”

“It’s really worth pivoting yourself than being pivoted on.”

“We lost something. But we gained something that allowed us to build this entire new business.”

“All these stories I’m telling are trades: What trade are you willing to make as an entrepreneur for your future…If you’re scared, you’ll end up staying where you are.”

“I said, [chat] is dead. I invented it, and I’m going to kill it.”

“You’re here for [your customers], but they also can help you transform your business, and they also can hurt it. So if you find those T-Moviles, they’re the ones that move you forward, but you may have to let some of them go that, you know, are holding you back.”

“If I was emotionally connected to it every day I would be a wreck.”

“There’s nothing more exciting than talking to a customer.”

“I’ve had my business for about 10 years now and that feels like a long time, but talking to you, it feels like I’m just getting started.”

“How many days can you go to work and have bad days and doubt? Usually those are instructive. There’s something telling you that this is not right. You gotta  listen to it.”

“It doesn’t get easier as you get bigger…it makes it harder, because I’m going after bigger dreams.”

“The business moves so quick all the time, if you’re not in it, you’re going to get lost.”

“The best thing I can do for my children is go to work, work hard, be happy, show them that it’s hard to do these things, and then when they grow up, they have lessons that I didn’t have to tell them.”

“The fear I have is that big tech will continue to dominate and, and they need to be disrupted.”

“At the end of our lives, you can judge us. But up until that point, we’re all in the game on the field playing.”

“Sometimes you can just outlive them, and that’s good enough for me.”

“Don’t quit when you’re down. Quit when you’re up, if you ever want to quit, but do not quit on your dark day. In my darkest days is where I found my greatest wisdom…those are given to you as a gift.”

“It all made sense when I told you. It didn’t make sense when we were in the middle of it.”

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