He Built A $6Bn Business and Left To Start Over… Here’s Why!

Rob locascio, Founder & CEO kid company

Episode Timeline

0:00
INTRO & GUEST
BACKGROUND
05:52
NAVIGATING CHALLENGES
LESSONS FROM THE DOT COM ERA
12:53
GROWTH THROUGH ADVERSITY:
THE IMPACT OF COVID-19
29:53
FROM PUBLIC COMPANY TO
START-UP: A NEW CHAPTER
34:22
NAVIGATING EXISTENTIAL
THREAT IN BUSINESS
47:08
LESSONS LEARNT FROM
LEADERHIP CHALLENGES

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Show Description

Robert LoCascio went public at 33, helped invent web chat, and spent nearly three decades building LivePerson into a $6 billion company. What followed was not the ending he expected.

In this episode of CEOs & ABCs, Kevin Rice sits down with the founder of LivePerson for a rare and deeply honest conversation about leadership under extreme pressure, navigating macro events like the dotcom crash, 9/11, and COVID, and what happens when the greatest threat comes from inside the system. Rob opens up about activist investors, an unplanned exit from the company he built over 28 years, and the emotional toll that season took on his identity and his family.

Rob shares the hard-earned leadership lessons that shaped him, from the moment a board member told him “just don’t bullshit them,” to why the best response to chaos is often no response at all. He explains why slowing down during crises creates clarity, how fear-based decisions compound risk, and why your weakest links matter most when you’re under attack.

The conversation also explores fatherhood, marriage later in life, and what it looks like to rebuild from scratch. Today, Rob is starting again in a completely different space, building a kid-first AI product designed around safety, creativity, and bringing families back into connection. This episode is a masterclass in resilience, integrity, and what it really means to begin again when the game changes.

In This Episode You’ll Learn

  • What it’s like to take a company public at 33
  • How to lead through layoffs with honesty and integrity
  • Why slowing down is critical during macro crises
  • How fear distorts decision-making at the executive level
  • What activist investors really do behind the scenes
  • How leadership pressure spills into family life
  • Why rebuilding sometimes means starting from zero
  • How fatherhood reshaped Rob’s definition of success
  • Why imposter syndrome may actually be your inner child
  • How to think about AI, kids, and creativity responsibly

Top Takeaways

  • Truth builds long-term trust, even in the hardest moments
  • The worst decisions are made when fear is driving
  • Macro events should be observed before they’re reacted to
  • Weak leadership links are exposed under pressure
  • You cannot dump the business onto your family and stay connected
  • Success brings visibility, and visibility brings risk
  • Resilience is modeled, not taught
  • No one can take your ability to create and rebuild
  • Starting over can unlock deeper purpose

Episode Transcript

Kevin Rice (00:12)
Welcome back to CEOs and ABCs. My guest today is Rob Locascio. Rob, thank you so much for being here.

Robert LoCascio (00:18)
Kevin, thanks for having me.

Kevin Rice (00:21)
Before we get into your career and your business story, we just had the holidays. How was your holiday season?

Robert LoCascio (00:29)
Good. It was a little interesting. We launched a product I’ve been working on for about almost two years. So it’s for kids and it was sold during the holidays. I was on like a 3 a.m. war, we call it the war room to handle any issues. So it was a different type of Christmas, selling a Christmas type AI product to children. But it was fun.

Kevin Rice (00:55)
Sure,

mean like Christmas, the holiday season is like the Super Bowl for retail. So

Robert LoCascio (01:00)
my God, I’d never been involved in

this software. So it’s like, this is whole different world for me.

Kevin Rice (01:06)
It’s funny when we my old company built software for the restaurant industry. So our biggest day of the year was actually the Super Bowl and we would hold war rooms because we would get tens of millions of dollars of orders per restaurant that we work with all on the Super Bowl. And it was quite the stress test every year.

Robert LoCascio (01:24)
Yeah, I felt the same thing. I’m like 3 a.m. up. It’s Christmas. It’s Christmas Day. know, I’m with my team. We’re all there waiting for people to come in. Luckily, small percentage had issues. I’m like, okay. But you still, you know, if you’re a professional like yourself, you know, you know, war room, the launch war room. you’re always, you know, we used to when I was at Running LivePerson same thing during the holidays, all that traffic.

People were chatting and we used to the war room set up. We’d lock everything down for like four weeks. It was fun. So.

Kevin Rice (01:53)
I can’t wait to hear more about KidCompany because I love the product and it’s something that I would love to have for my kids. But before we do, I kind of want to go into a little bit of your backstory. In 1995, you founded LivePerson, which became a hugely successful publicly traded company. And so could you share with us, what was that journey like? Because you navigated the dotcom bubble, the financial crisis, COVID.

And then eventually had an ending that you didn’t really see coming. And so I’d love to hear kind of what that experience was like.

Robert LoCascio (02:29)
Yeah. I mean, I started in 1995 building websites in 1998. I invented web chat on websites, so it didn’t exist. And I thought it up and, cause I had these e-commerce customers who were trying to sell online. thought about, you know, put the human salesperson on the website. And then from there built it up and then took it public in April 7th of 2000. We were really like one of the last internet IPOs of the dotcom age.

and we went from $8 a share straight down to seven cents a share a year later. I witnessed 9-11, you we literally watched the towers come down, I was in New York City. So there was a lot that happened, it was kind of trial by fire. And I was really young, I was 33 years old when I went public. So I was kind of dealing with many different things.

Kevin Rice (03:20)
So you were a

publicly traded CEO at 33 years old?

Robert LoCascio (03:25)

  1. was

33 only. Yeah. And there’s no like real lessons or, you know, things for how to run a public company. I was very fortunate to have some board members who, ⁓ you know, had run public companies or been involved with public company stuff and have been really amazing. And I remember this guy, Bob Matchlot, who was on my board. He was on the board at Disney. He’s like vice chairman of Sieggrim’s one time. He was a pretty big guy in the business world.

when we were going to fire like 80 % of the company to survive during the dotcom. And I remember he pulled me aside after the board meeting and said, you know, this plan was like pretty from to go from like 200 people down to 40. And I said, you know, we if we don’t do it, we’re to go bankrupt. And anyway, he said, look, you’re a young guy.

and you got a whole career ahead of you. He goes, I don’t know if this is gonna work, like if LivePerson make it, it’s not clear, but I’ll give you one piece of advice. he said, “just don’t bullshit them.”

your investors, your employees, they’re gonna remember you for this moment. And your career may end here. If you you have a full career ahead of you, you’re young, but it can end here by just not telling it the way it is. And I remember where that really came to light was when we laid off, we brought everyone into the, everyone was in the office, we assembled everyone in main area and said, look, we’re gonna do layoffs today. we gave everyone an envelope.

and said, if your envelope says, come back for lunch, you’re staying. And if not, you’ve got 15 minutes to leave. And we had guards at the time because there was a lot of weird stuff that was happening. People were like really upset. And there were things where people were getting hurt at companies and we just whatever. And ⁓ I remember when we reconvened with the group that was going to stay, the first question they asked me is, will there be more layoffs? And I remember Bob’s voice in my head and I said, I can’t tell you

whether they’re gonna happen or not, and you should make a choice based on that. And the normal thing you wanna do is tell everyone it’s gonna be great. No, it’s never gonna happen again, everything’s okay. And the reality is you don’t know. And when we got hit with the Twin Towers and we all witnessed it, I had the same sort of thing happen there. One of my heads of sales was like, Rob, we gotta fight the terrorists and this and that.

Kevin Rice (05:29)
Hmm.

Yeah.

Robert LoCascio (05:50)
And I told people, you know, I remember people really didn’t like him for doing that. And people were just absorbing the fact that thousands of people died. And we were in New York City. And I just said, look, if you have to go home or if you need to leave the company, I we cannot be responsible for your person and you have to do what’s good for you. But I can’t rah, rah people through you can focus on. But but people know when you’re bullshitting, you know.

Kevin Rice (06:16)
Yeah. Yeah. I had one layoff experience in my career and we were probably at, I don’t know, 40 employees or something like that. And we had to reduce about 15. So at a small company size, it was substantial. And I think unfortunately a lot of companies don’t cut deep enough. Like when it’s a necessity, right? Like today it seems like there’s a lot of layoffs that aren’t a necessity where it’s like,

this is actually almost become a publicity stunt where it’s like, we’re going to lay off 10 % of our staff because we’ve invested in AI and oh look, our stock price goes up. We’re talking about a different kind of thing where my company was going to go out of business. We had our revenue dropping by like 50 % over the course of a one month period. And so if we hadn’t done that, we wouldn’t have sustained the company, but it’s, it’s such a difficult thing to do.

Robert LoCascio (06:52)
Yeah.

Kevin Rice (07:12)
to go to people who you’ve worked incredibly hard with and tell them they don’t have a job anymore because as a leader, it rolls up to you. And ultimately, it’s your responsibility to run a sustainable business. And at the time, I felt like I had failed them. And it led to a lot of changes in how we positioned, how we operated, how we invested in the company. And thankfully, those changes led to

with our growth and eventually a successful exit. But man, that was such a tough period ⁓ in my career.

Robert LoCascio (07:41)
yeah.

And I mean, we, ⁓ you know, just, for people that are out there, I mean, we, we, myself, my CFO and like my head of the kind of customer success got together one day and we is that this bar called Blackards, which was downstairs. literally 10 o’clock in the morning. It was one of these bars. was open all day. We’ve sat in there. Didn’t didn’t drink obviously, although I wanted one. I we made a list of all the employees names.

Kevin Rice (08:05)
Yeah.

Robert LoCascio (08:07)
I had three copies and gave it to each of us. I said, there was a column said skill and the other column said will.

And we honestly went through it and you had to check both boxes. And there was a handful of people we had debates on. There were three people who I was there at the beginning with me. They weren’t founders. I founded, but I hired them, the first employees. they were the founding team. And I was like, they didn’t have, some of them didn’t have the will anymore because they had a lot of money when we were in public. Now the stock was worthless and they were angry, you know? And so…

Kevin Rice (08:15)
Yeah.

Robert LoCascio (08:39)
You know, we made this list and it saved us because it wasn’t the people who stayed where people had both columns, regardless of whether they were the best skilled. They had to have the best willed and and skilled we we said, OK, this person isn’t the best at that job, but they sure as hell will fight for us. They came in early late late. can feel me. They came in early, loved the company and they’ll go through whatever we’re about to experience. We can’t have people getting off the boat.

That was what we did.

Kevin Rice (09:06)
Yeah.

So you got through the dotcom bubble. Ultimately, the company continued to grow. I think at one point you were a $500 million company.

Robert LoCascio (09:11)
Yeah.

We’re five billion. I mean, our top was six billion. That was our top. Yeah. So during COVID, we had about six billion in market cap. Yeah.

Kevin Rice (09:23)
Tell, you know.

Where does the story take you?

Robert LoCascio (09:31)
Yeah, from there, I ended up pioneering. I jump ahead, know, chat became a thing. Obviously we started to sign up a lot of big enterprises. I made a huge bet in 2016 that I could, I’ve started to see that the value of the business was all this conversational data sets we had. We were thinking about automating them. Now AI was machine learning at the time, but large language models were sort of coming about.

There was some hint to what they would do, but we, I made this bet that we would get into the AI game and we re-platformed and made a messaging platform so you could like message a brand instead of chatting on a website. That was the first part. And then the second part was building all the AI rails. So when COVID hit,

we basically, the contact center shut down and all these big brands like Verizon and T-Mobile and they’re all like, we want to, we need to automate everything. Like everyone’s, no one’s in the contact center. So we need chat bots and we just grew so fast. And we became a company, went from like 900 million in market cap in 2019 to I think 5 billion, six between five and 6 billion. And we hit six one day, but.

In a matter of like, I think it was 18 months. It was just some weird ride and, and I wasn’t ready for it in many different ways. we had become on a lot of people’s radar at that time. And for many years I was flying under the radar, and just doing my thing. And, know, I’ve already, at that point I’ve already been like 26 years into running the company and, ⁓

So yes, so that’s why that you kind of, know, we’re in the right place at the right time with the right strategy.

Kevin Rice (11:16)
Yeah, yeah. I had a very similar experience. We were building software for retail and restaurant. And in 2019, we did about 15 million in revenue. By 2020, at the end of it, we did over 20 million. And by the end of 2021, we did 42 million. So we saw a big lift because we were the only reason restaurants were able to continue operating. All their doors were shut. People couldn’t come in and get food. So it was all online ordering and delivery.

Robert LoCascio (11:39)
Right.

Kevin Rice (11:45)
or curbside pickup. And we weren’t sure when it first happened, we weren’t sure like, are we going to survive this? Are clients all going to go out of business and we’re done overnight? Ultimately, that’s not how it played out. And we realized our value is actually even higher than it was before COVID happened.

Robert LoCascio (12:03)
Well that, that.

That was the interesting part because I’d gone through dotcom. financial crisis was really interesting because we grew fast there too, because as companies were looking to cut cost, we were a way to get better leverage on labor in a contact center because people could chat with more than one person simultaneously as an agent versus phone calls. So we like did really well during then. And the stock got killed because we were a public company. And I actually ended up buying a lot of stock. Like, man, I’m going to and I should because I realized during the dotcom, I could have bought the entire company for two

million and I didn’t and we had 7 million in cash. And I just was afraid. I was afraid because it looked like the whole business was going to zero and we got the profitability at the end of 2001. I was like, let’s just like just hold on until in the 2003 things picked up. But anyway, I made it through all these things. when the COVID hit, I sat with my team. I was like, the lesson I’ve learned through macro events is don’t respond.

Don’t ever respond to the event as it’s happening. You almost, want to slow down time, like cut time in half.

slow it down to half your pace and let it get ahead of you. Because when the wave is coming in, you want it to pass you and then you follow it. If you are trying to go ahead of it, it can put you under. And what I mean by that is that you’ll start making a set of decisions based on fear, anxiety, doubt.

Kevin Rice (13:24)
It’s gonna close out on you.

Mm-hmm.

Robert LoCascio (13:33)
because you’re looking at a wave and it’s, and you don’t even know what the wave is. So my thing is like, I just saw a team, I don’t say the thing was first. He was like, Oh my God, like no one’s going to want to do things because no one’s at work. And then very quickly it was like, yeah, the contact centers are not going to work and they need to talk to their customers. So like we’re in, but the wave had kind of come through us and within like two weeks we saw volume go up by 40%. It was extraordinary. I still have the

Kevin Rice (13:52)
Yeah.

Robert LoCascio (14:01)
print out of it. So I often say like when you get hit with a macro event, stop, slow it down, just let it play out a little bit ahead of you and then you can start to respond to it, but you’re not being chased by it.

Kevin Rice (14:15)
Well, I think it’s not just a business lesson, but it’s a life lesson that you really hit on the head there is just don’t make decisions from a place of fear. If you’re making a decision from a place of fear, it’s probably not gonna be the right one.

Robert LoCascio (14:29)
Yeah, I mean, this is the thing and it’s being, running, you know, running a business. There’s a lot of emotion in it and how you regulate that emotion, which is very hard. I mean, I, you know, I’ve got two startups now and I talked to, you know, guys who run companies and give advice and stuff, but everyone’s in the same game. Like there’s a lot of uncertainty. There’s a lot of things going on. It’s easy to react.

And then what you end up doing is you’re in the wash. Like once you’re in a washing machine of decision making, you’re kind of in trouble. You know, you’re going to get dizzy and you’re not going to like, you’re just being cycled. You, you know, you always have to be the, the cycler. You can’t be cycled. You know, so, uh, you know, you just, like you said, if you can make decisions a little bit calm, you’re in a better place.

Kevin Rice (14:53)
Yes.

Sure. I never had the opportunity. my company was privately held much smaller than the scale you’re talking about. But I imagine running a public company is a different level of pressure, lot of visibility, you know, very high pressure, like decisions. What, you know, take us through like a high growth season, like what did a typical week look like for you travel meetings and then how did that, you know, like

play into your like family rhythms.

Robert LoCascio (15:45)
So I, you know, I, it was very interesting because when I got funded by a group of C there was a fund in New York city called Dawn Treader. And it was this guy, Bob Lesson, who was a banker and all of the limited partners were the greatest CEOs like, you know, in the country where we’re in this fund. And I got access to these people, these guys.

And I got to talk to them about their lives of being entrepreneurs and building these giant companies. And I heard the same story over and over again. A lot of it was they were divorced and they all had second wives. And I really started to think about that concept. And I kind of very quickly…

Kevin Rice (16:17)
Hmm.

Robert LoCascio (16:27)
It was very funny when I went public, had a girlfriend who was with me during the building years and we were at NASDAQ opening up the market and my parents were there and it was a dream of mine since I was a 14 year old kid. I read a book on going public and here I was going public. And my parents told me the story that she turned to me and said, like, are we getting off the bus? She asked me, are we getting off the bus? And I just ignored it. And because I was in the moment of opening NASDAQ and

And then what happened when we went through this restructuring that I talked about, she said something to me that really resonated with me. She said, what you do is not normal.

Cause I told her I’m about to go through a big layoff. It’s going to get hard again. This is going to get really, this will be really, and she saw me through the formative years of like sleeping on a couch. I mean, she saw the, and she said, you know, what you do is not, it’s not a normal life, And I don’t want to be a part of it anymore. Like this is just not normal. Like you’re, it’s all about the business and there’s no room for anyone else. And I was like, so I kind of, I stayed single until I was 47 because I realized I traveled over 200 days a year because we had offices around the world.

⁓ every 90 days I do a quarterly call and three day board meetings and it just is a lot and it’s hard not to be selfish. And like I said, I, I, I heard a lot of stories about, can understand people, losing their marriages and their families for their business. Cause it is a very selfish act building a business. I don’t care who you are. It’s a very selfish act. You have to be selfish at times, you know?

Not that think that’s good.

Kevin Rice (18:03)
At what point did you At what point in your career did you end up having three kids right now? Where were you at in your career when you started a family?

Robert LoCascio (18:12)
Yeah, so I, yeah,

so I met my wife when I was 46. I got married at 47 and we had our first child, you know, 10 months later. And, uh, so, yeah, so I was around 48 and, uh, and now I have these three kids, nine, uh, seven and four. And so, um, yeah, it was, I just felt like I was in a place in life with the business. The business was big enough and

I felt I could put time into having a family and, know, but also I got married later in life and my wife met me in my formation. You know, she met me in the world where I was traveling around the world and doing things. So she kind of understood to as much as a spouse can about, you know, what it takes to build business.

what it takes to run of that magnitude, you know, and be competitive.

Kevin Rice (19:09)
Mhm.

So you were still with LivePerson for at least a handful of years when your first child was born, right?

Robert LoCascio (19:21)
Yeah, yeah. Basically through ⁓ all three of them were born while I was still a liveperson. Yeah, exactly.

Kevin Rice (19:29)
Yeah.

During that period, you know, how were you able to stay connected with, your spouse, your kids, like, was there, you know, a tention between the competing priority of running this publicly traded company and being available for your family.

Robert LoCascio (19:47)
during COVID or just in general?

Kevin Rice (19:49)
Just in general, yeah, any specific, were there any periods where, you know, you felt that tension?

Robert LoCascio (19:54)
Yeah, mean, look, there were COVID was really interesting because you’re with your spouse and you’re with your family like all day, more or less, you know, so actually it was a very different experience. And it was really quite, there were a lot of good things about it, you know, on that side, because you weren’t in work and you didn’t I travel for like two years. So I was basically off the road and at home, which is a real benefit. When my kids were, my first two kids were really young and then

Kevin Rice (20:14)
Yeah.

Robert LoCascio (20:23)
third one came at the end of COVID. But yeah, I think it’s still a very challenging thing. I think anyone who’s a spouse to someone who runs a company, I think it’s a challenge. And I see all these things posted on social media by people. They have it all figured out. It’s like, you

I do date night and I do this and I’m with my wife here or with my husband there. we did, it’s like, mean, it’s so funny because we’re human beings and we’re trying to, you know what I’m saying? Yeah, but it seems like somebody figured it out. I have a friend who’s a CFO of a big public company. I see her, she posts the stuff with her family now and she’s amazing. But it’s like a little bit like, okay, you you know, I think God has his hand.

Kevin Rice (20:56)
We’re all just trying to figure it out, you know, like I’ve…

Robert LoCascio (21:12)
that shows up at times to kind of like, you and I talked about Tony Robbins before we were on air here and like, he talks about uncertainty and certainty and we get both of these things at times and humans almost want them. So at times when you get a lot of uncertainty, you’re gonna get focused on something and maybe it’s not your spouse, maybe it’s not your family. So I don’t think it’s a perfectly balanced life. you know.

Kevin Rice (21:14)
Mm-hmm.

Sure.

Yeah.

Yeah. Yeah. mean, I certainly, I mean, I’m trying, I’m trying to write a book about these sorts of topics. Obviously, you know, we’re doing this podcast. I don’t have it figured out. I’m a big reason I started this podcast was to learn from other people who are going through the same struggle of trying to, you know, have the career that they aspire to have while still like being present and available for their families. it

It is a really challenging thing. And I just wanted to create space for that conversation because some people have some great lessons and ideas and some people are honest and they’re like, I’m still really struggling right now. but I think it’s just such an important conversation to make available. So people don’t feel alone in that struggle.

Robert LoCascio (22:21)
But I think that’s that’s the big thing that I hear from people and you can feel is that People talk about being alone running a company part. I remember I remember my wife My wife because you’ve been married now ten years. So not a long time, but somewhere During the route during the routine of running the company I remember she said don’t you have a good life coach? she was like, I kind of was like going on about something and I

Kevin Rice (22:28)
Yeah.

Robert LoCascio (22:45)
I learned very early on with that first relationship I had before I went public. I said, I really wrote down some rules. One rule I wrote was like, nothing ever really happens in a day. Don’t take everything home with you. And it was very, I call it abusive in a way that…

If you take your business home all day, you’re kind of abusing people around you because you’re taking all the garbage. Now you’re throwing it on them and telling them. And I use that word. It’s probably maybe it’s not the right word, but I think for the people on the other side, it can feel that because it feels like you’re negating them as being important that emotionally you’re not available that,

that no matter what they say, it won’t be good enough to solve your problem. And because you want them to be like, you know, Tony Robbins and Deepak Chopra and the Dalai Lama and whoever else all in one because they’re your spouse and they’re just trying to do their thing too. So.

Kevin Rice (23:36)
Yeah.

Well, your

spouse or your partner can’t be 100 % of your support system. That’s not fair to anybody. You know, that’s where, you know, a psychologist, like a therapist, a coach of a community of friends that you can share, you know, more intimate, you know, life experiences with. That’s really important because yeah, you can’t just be dumping on your partner all day and expecting them to like, you know, hold space for that.

Robert LoCascio (23:55)
That’s what saying, yeah.

Yeah, and if you have a partner that has a, you you married him for the right reason and they have, you know, strength and love and they make a good spouse and a good parent.

They have their own strength and they have their own reason that they’re there live in their lives, which are intertwined with yours, but it’s not all about your life and your business. And the business can become very, very over consuming. And I’ve seen that over and over again. So like I seen it and it’s By the way, it’s hard. Like I’m in two startups now. It’s it’s back to like that jujitsu thing that at least as a public company, I could try to fake it a little bit, you know, running when I had

I had a bigger staff and people do things that I’m doing now. I haven’t done for years, you know, and so it’s a different game when you’re building businesses.

Kevin Rice (25:05)
Yeah. Well, tell us about how kind of the story of your time at LivePerson ended and how you are now in kind of back in founder startup mode.

Robert LoCascio (25:15)
Yeah, so I was interesting in 2000. It’s like 2022. We got we got attacked by an activist shareholder and my sector got really hammered. There’s come a call Zendesk and then Twilio and us and all three of us who are really innovative. You know.

in the industry, were shaking it up because we were going against the traditional call center guys and we were really, really taking them down and between the three of us. I’m actually friends with them and the other guys and we all got attacked by activists and for whatever reason.

Kevin Rice (25:44)
Yes.

Robert LoCascio (25:55)
We all had different outcomes with it, but we ended up all exiting. And, you know, I exited in 23 and, but I ended up fighting my board, you know, I like, cause we gave the activists some seats and, then I ended up whining. I consider it an existential threat to the business because

I, they didn’t have an understanding of the business and they were not there to be a helping hand. And today the business lost 90 % of its value. It’s almost half the revenue that it was when I left. And so I felt that they were there. And then after I left, funny enough, they sold their shares and just left like a day later after I stepped down.

Kevin Rice (26:27)
is.

Robert LoCascio (26:39)
So I, I, you’re in a business for 28 years and all you understand what existential threats are and they come in different shapes and sizes, external things like, you know, we’re saying the dotcom or financial crisis. And in this case, it was in the, in this, in this type of a shareholder. and so I ended up exiting my own company without a transition.

And it wasn’t really, uh, you know, I’ve never really talked about it, but it wasn’t the plan. And it affected a lot of people because I had deep relationships with customers. You know, some people I’ve known for 20 years, cut employees, you know, so.

Kevin Rice (27:09)
Yeah.

Yeah. I mean,

how does something like that happen? Cause I mean, I hear about it, but I’ve never heard like the inside track or inside story of like, build this company into a $6 billion business, you know, from the ground up being a, one of the top leaders in AI. And how does that end with you being exited from the company? Like, it’s hard for me to understand how an activist investor group can come in and, and completely like take control.

Robert LoCascio (27:43)
It’s very interesting because it’s a very corrupted system where the SEC has not created any real rules for this group of shareholders. so what happened was it’s very, it’s really interesting. The most 30 % of LivePerson was owned by passive shareholders. The Fidelities, the Black Rocks, they don’t even, I didn’t know, they didn’t even know who we were.

Imagine 30 % of shares. And when I first went public and for many years, I knew my top shareholders. I would go to dinners with them. I knew their families. You become friends in this. And they’re usually in early stage tech, they’re usually innovators in themselves. Like they want to be innovative investors. And that all changed somewhere as more capital came into the market, especially with passive funds. So it turns out in the end,

You don’t really, even the people who normally be close to, they’re just trading, you’re one of a basket of 200 in their portfolio. So that I realized like, I don’t know how many years it went over time, but the relationship definitely changed. That allows them to come in and play a game because nobody really wants to be active. And the passive shareholders are not even there. You can’t talk to them. There’s no one to talk to.

So there’s a, what we call a proxy contest that they can nominate every year, shareholders and shareholders can vote. And that process is so busted that they could make change that could hurt a company. And, and the general shareholders can’t do anything because sometimes the passives just vote because there’s these things called proxy advisors.

That will say vote against the the the company for whatever reason in our case It would be like because we had we had board members who were on for more than 10 years These are great board members. I like guy was the founder of zappos like fred moza like but because they’re on for 10 years You need to be refreshed every four years You should refresh your board. That was a five So all these weird rules anyway, not to get too technical It puts a threat it instantly puts a threat in your business instantly You could lose your business

And I remember just recently seeing a podcast with the founder of Whole Foods. And he said when he got attacked by the, he got attacked by an activist. They sat him down and said, look, if you don’t sell your company, we’re going to like destroy it. And, and it’s, and every CEO I’ve talked to who got faced with an activist, it’s like, get a Scarlet letter. This is how I describe it. It’s like, you’ve got a Scarlet letter now. Like the plague came to your business and you’ve got the plague and now you’ve been branded with that.

And then their whole job is to discredit you, discredit the company, discredit your big board members. And the one thing the board members, no board member wants is usually, I don’t really want to be publicly discredit because this is kind of like not a full-time job for me. So it’s really fine because it’s made for these people to walk in the door and take anything they want and destroy it over time. Now there are activists who’ve come in and saved companies and I get it.

Most of the time.

Kevin Rice (30:54)
Is the

end game just to get control of the company? Is that like?

Robert LoCascio (30:57)
I realized there’s

a many end game. So that’s the thing. It’s a game of chess. In some cases, most of the time, private equity puts them up to it to get you sold. The private equity people don’t want you. They’re like from Harvard and they’re the white gloves and they’re there to be helpful, but they don’t do the dirty work, but they may want a company to be sold. In the case of one of the companies in my world, Zendesk, they got sold. I fought.

The other guy left and someone else took his job, but it’s a yes, there’s different paths and they may want to destroy. Because it just takes you out of the market against a competitor that a private equity firm may have and

It’s my past. don’t have any like personally, I’m not like, my God, I’ve got two companies. I got a whole life. And it’s so far in the past, but it’s a very strange thing. And I’ll tell you the one thing is that I spoke to a lot of CEOs ⁓ who were involved even with my activist and like Aaron at Box, Box was attacked by the same guys and he beat them off. and

Kevin Rice (31:40)
Mm-hmm.

Robert LoCascio (32:03)
It’s always like, everyone’s like, I don’t want to be, I don’t even want to get involved with it anymore. I’m like, I got PTSD from this thing. It’s like, it’s, it’s like a weird world that those people come from and they’re not straight shooters and that we couldn’t put fake things out about anything we have to wear public companies. So everything we write about has to be in our knowledge factual. And on the activists side, they can write a bunch of lies and put out press releases and then,

Kevin Rice (32:11)
Yeah.

Robert LoCascio (32:31)
we would tell them like, hey, that’s a lie, what you wrote about me. And then they would file another like filing with the SEC at like a private filing, like an 8K saying, yeah, that was wrong. We admit that we didn’t, but the press release is out. Yeah, even today there’s stuff out on me on that. It’s like ridiculous about this. And they write about like my ratings on glass. was all they made fabric. I ran a company for 28 years. Like I’m not, I didn’t have anything to hide. was like, I knew it was.

Kevin Rice (32:43)
The damage is already done.

Yeah.

Robert LoCascio (32:57)
I was public since I was 33, but it was really funny. But it’s just, it’s a different world. So I decided I’ll take my exit package and leave. And I believed in God and I have a great belief that there’s a higher power and that this was given to me for a reason and I’m holding out in the company, you know, this isn’t my future. I know it sounds strange because if you built something for 28 years, you would think it’s your future. But I was like, I realized it’s not my future and nobody can take my ideas.

Kevin Rice (33:26)
Sure. How are your experience, you know, what you built? When you when you were going through this, how like aware of what you were going through was your family and your children?

Robert LoCascio (33:27)
We can take my company, the vehicle to make it. Can’t take my experience, can’t take that. Yeah, can’t take that.

I mean, they were very aware. I see they’re living through this and there was a lot of stuff with lawyers, know, like it’s mostly like we’re dealing with lawyers and battling stuff and filings and a lot of stress. And yeah, they were, it’s not a normal world and nobody should feel sorry for anybody, it was, it’s a very, these people are bullies and they.

Once again, I grabbed 100 CEOs who were involved with this, they would say the same thing. I remember one guy told me he was on the phone with one of these people and his wife was listening to it and she was almost ashamed. He told me this. She was fearful and ashamed at what was happening to her husband because she was listening to the conversations from these people on the other side.

because they’re bullies and they talk in language and they say words that are not, these are not business conversations. These are just make you be fearful. So obviously you try to process that and not bring it to your family, but you’re gonna bring it to your family. And they know that by the way, the whole idea is the whole job over there is to wear you down. Eventually you’re gonna get tired. To them, it’s unemotional. Remember.

Kevin Rice (34:31)
Mm-hmm.

Robert LoCascio (34:45)
If I come in as a third party and I attack a company, this is just a it’s a game like I’m 20 of these things I’m running or five and you’re one of them to you, It’s like existential threat. It’s your life. It’s your business. It’s your you know, it’s like whatever like so they get on it’s and then they do their shtick. It’s like it’s like a comedy act and but it’s not funny.

Kevin Rice (34:51)
Yeah.

Robert LoCascio (35:06)
And on your side, you’re emotional about it because it’s about loss of value, loss of employees, loss of credibility, loss of who knows what. And on their side, yeah, whatever. It’s like, you’re going to make money. making money one way or another.

Kevin Rice (35:22)
Yeah, what kind of lasting impact do you think or impression do you think that made on your family when they saw you going through this period?

Robert LoCascio (35:30)
You know, they just realized that my wife was pretty straight shooter about, she’s just like, what is this all about? She was kind of like, you’ve done well and you should be proud you built a company for 28 years. How much longer you gotta stay around on this thing? It’s a sinking ship.

Her perspective was like, you’re on a sinking ship and whether you want to admit it or not, it’s sinking because now you’ve got a crew of people who are on the board and this is not going to help keep the company afloat. So like either you stay on the sinking ship and go down with it or you get off the sinking ship. And what I realized like, because I’ve been through so much building liveperson and I’ve been through so much in my early life. After I left college, I had another company went under.

I kind of thought I was really curious what was out there. And so eventually, you know, I just talked to my family is like, you I got let’s do it. And then I flew out to California and then a couple of times came back and talked to my wife and said, Let’s go. It’s time for change. The powers on the out. You said the other things, the sink and ship. You’re right. I probably wasn’t. I honestly, Kevin, I wasn’t happy for many years.

Kevin Rice (36:38)
Yeah.

Robert LoCascio (36:45)
When the dot when the COVID happened and many of you are leading companies would understand it’s like I don’t think anybody cared anymore. Like not everybody, but it’s just law. used to be like a culture business because of our offices and people came together and we shared a personal connection and one of our one of our meaningful connections is one of our core values. Create meaningful connections. And.

Kevin Rice (37:13)
Yes

Robert LoCascio (37:15)
Nobody cared. Like I went to the offices in New York. Nobody showed up. It was like there were thousands, hundreds of thousands, couple hundred people lived in the, around that office and nobody cared. So I realized like, I wasn’t happy. There was a lot of other stuff happening, DEI stuff. There was all this stuff going on that didn’t have anything to do with our business, but we had to manage through it. And eventually I was like, you know, do I really love what I’m doing? Probably not you know.

Kevin Rice (37:39)
Yeah. When, when you were exited afterwards, like how did you kind of reshape your life and rebuild from there?

Robert LoCascio (37:48)
I went back to the foundational things that got me through when I was living on a couch. So I’m not living on a couch, but I went back to the foundational things that I brought into my life to help me steer through the change.

And so I’m saying one of those things like Tony Robbins. when I was sleeping on this couch for two years, I went to Tony Robbins and it really changed my life and I learned a lot. then I got a coach from there for many years. then I had stopped going for like, I hadn’t gone for many years because I kind of felt like I learned everything I needed. But I went back and I went back to Unleash the Power Within. was like, my God.

First, I brought so much into my business. I forgot how much of like the structural stuff I brought in. And then there’s so much I forgot. was like, so I was like, it gave me that jolt. I went back to my, you have to do your, you have to do a pattern of things to, to move forward. You emotionally want to be strong. And so I started to just bring back into my life. That’s not the only thing, a bunch of things that I remember would help me rebuild, you know, build the next foundational parts of my, of my life.

Kevin Rice (38:38)
Yeah.

Yeah, that’s awesome. I mean, we talked, we’re both members of Tony’s platinum group and I went to a date with destiny in 2018 and then I got my business partner to come to business mastery in 2019. and that was a big turning point for our company. You know, we set some goals that we exceeded that next year and then it was just like off to the races afterwards. Um,

Yeah, Tony Robbins and his messages have just been a consistent presence in my life.

Robert LoCascio (39:34)
Yeah, and that’s why when I went back to date with Destiny and stuff and joined the Platinum group and I like I was like, you know, there’s just so much stuff there too. And then they made it. It definitely changed since I had last gone and as much as what like a lot more programs on stuff. So I was like, this is cool. It doesn’t matter. Like if you go through this, I once again, I had this thing happen to me or for me

Kevin Rice (39:49)
Mm-hmm.

Robert LoCascio (39:58)
because you can look at it at, you know, is it for you or is it happening to you? Let’s say something happened for me and now I need to just kind of work through it. And we packed our bags, left the East Coast, came out to Silicon Valley and it all happened within like weeks. know, basically I, you know, I told my wife, go look, got, there’s nothing here for me anymore. I’m not going to, was in Connecticut because during COVID we got a place there and like.

I can’t build here. I’m going to go to where AI is happening and I have some ideas and really packed the kids up and took them out of school and came to here and just settled in. And I just started to work out of a WeWork. And it’s funny, I met with one of the top guys at Andreessen Horowitz, who’s a friend of a friend of mine. Actually, he’s now in the Trump administration, Scott and

And I met with him, he goes, know, he goes, you know, and I had some ideas. didn’t tell him. I was just there to meet. I started to meet people and said, guys like you, we don’t like to fund a lot. And I said, why? goes, because we find you hire like EV executive vice presidents and vice presidents. You’re not good startup guys anymore because you built these companies. said, well, said, Scott, I’m at we work right now and my, my EA is a virtual, virtual EA from the Philippines, 200 bucks a week.

Kevin Rice (41:06)
Big companies, yes.

Robert LoCascio (41:15)
I’m like, I’m doing everything. I said, trust me, I know what it’s like to be at a startup. I didn’t come from a big company. I came from a startup. So I tell that story because you got to get back to the roots, getting back to the roots of what it takes to build a business, rethinking how you want to build it differently. I have a lot more experience. What were the lessons I learned over the last couple of years? How do I take that into my future?

Kevin Rice (41:39)
Hmm?

Robert LoCascio (41:43)
So that’s the stuff that really was interesting to me.

Kevin Rice (41:46)
Yeah, what were some of those lessons that you learned from the experience that you’ve been able to carry forward or you plan to carry forward?

Robert LoCascio (41:52)
I mean, in the end over there with ⁓ it’s like I left a lot of deadbeats around and part of the activists because I couldn’t really fire people and stuff and I was usually pretty hardcore about that. like just.

There’s two big lessons I learned, like, they’re obvious, they may be very obvious. And so sometimes the obvious lessons are the hardest ones. I left, I gave people opportunities that didn’t have the right to have the opportunity. And I did that a lot and a lot. And sometimes it worked for me, but I put people into positions of power that didn’t have the qualifications thinking. I don’t know what I was thinking to be honest, who then when they got those positions, didn’t deserve them, knew they didn’t deserve them. When they got an opportunity to kind of take advantage of that, they would.

They don’t because they they know deep down they shouldn’t even be here Why would give them an opportunity to get there and then there were people who I left around? Especially on the board that really are like they’re not really winners they didn’t have jobs for many years Maybe when they came to the board they had stuff but over years their careers went kind of nowhere and I left them like why so why I tell that story is when something then happens

the weak, the you’re only as good as your weakest links and those weak links are really detrimental when you’re under attack. If everything’s great, it cares. So like.

Kevin Rice (43:07)
Sure.

Well, you’re under a microscope when you’re promoting people because maybe they’ve had the tenure and like they deserve it, but they don’t actually have the skills or qualifications to be in that role. Everybody else sees it and they judge you for it as a leader. And it creates problems beyond that one role, you know, throughout the entire organization.

Robert LoCascio (43:30)
Yes. And so like I said, to get 28 years, had to do a lot of like, I had different leadership teams. had a cycle teams and cycle people in the end. you know, like, and so that, I, and that goes to my second one, which was that when we went from like 900 million in market cap to multi-billion market cap, and it happened so quick, I wasn’t prepared to understand that I was now on a different radar of people in the world. And so.

And I wasn’t prepared to have people around me, not even just working with me, but advisors that I have today that are used to dealing with that kind of market cap and that kind of stuff. they know because, and when I started meet with these people or, or it was like one or two people in particular and they they’re working with other well-known people we know in the world, like very powerful people in tech.

There’s a thing that happens, like once you get on people’s radar, you’re like a target. And you find that a lot of people just want free rides. Like they want a free ride. And some people want a free ride in different ways, but a lot of people just want free ride off of your success.

Kevin Rice (44:33)
Thanks

Robert LoCascio (44:39)
because they think they can get it and they think they can get it in different ways without working for it. The easiest free ride is without work for it. And so I never realized I was kind of under the radar for most of time, even running a public company where we weren’t Salesforce and stuff like that. You know, we’re big, but they were, you know, they were on a different level and all of a sudden we popped up on everyone’s screen. Wow. These guys are there. Then now a bunch of people look at you and go like, I want a piece of that. And

Kevin Rice (44:44)
Mm-hmm.

Robert LoCascio (45:04)
I want to get that in a way that I don’t have to work for it. And there are people in the world who can help you and like advise you and who have dealt with that kind of situation of success and be like, well, this is how we navigate it. And this is how I protect the business or protect you. so just you never my lesson there is be aware where you are. Be aware where you are, even if it moved quick.

Kevin Rice (45:30)
Mm-hmm.

Robert LoCascio (45:30)
And then

be aware of who needs to be with you at that point. And then be aware that the more you are successful and more you’re on people’s radar, the more you’re a target.

Kevin Rice (45:39)
When, I mean, when you got knocked down from, you know, this being exited from this company that you’ve spent so many years building, and it was something your family experienced with you, how important has it been for you to show them your resilience and show them that you’re, you’re somebody who can get back up and how like,

Sorry, I’m going to rephrase that because that sounded terrible and this is recorded, so I get to edit. After building a company for 28 years and then getting knocked down, was it important for you to show your resilience to your family and that you can get back up and you can build something again?

Robert LoCascio (46:10)
That’s fine.

Well, I think it starts with it starts with you. Like, you have choices at that time. Do you want to continue forward? Do you want to? So I think yes, it like I felt I read somewhere or, know, as a parent that you you don’t teach your kids values. They watch how you act.

Right. Especially my kids are in the formative years, right? They’re they’re experiencing this literally in the middle of being three, four, five, six years old. You know, like they’re they’re in those years where they’re just they’re just sponges around what’s going on in the world. And so here they are experiencing something with their dad and their and their family. And they’re definitely observing. And I felt like, you know.

Like I’d learned from my family a lot of, because I came from a family of entrepreneurs and there were always these tough stories and coming from Sicily and with nothing. it was the whole thing. So just felt like I’m just, you know, I have the ability to show my kids that, you know, it’s just what it is. Move forward, build again, and you don’t get down and let them know that there’s nobody in the world.

My grandfather wrote me this great letter. He had a handbag business that he had in New York City. During the war, it stopped functioning because he couldn’t get the supplies anymore, like silk. Then after the war, he never went back. He ended up working for a handbag, Judith Lieber, and he regretted it in many ways.

He was a great man and a wonderful friend to me. And he wrote me a letter when I graduated. said, in the letter, he many things. But he wrote one line in particular. still have the letter. said, just remember that when you get out in the world and you go to follow your dream, because I know you’re going to want to follow your dreams, that there’s going to be a lot of people who don’t want you to succeed. But you cannot let them get in your way.

And it’s what I remember that my children, wanted them to see regardless of these, because in the scheme of life, all that stuff that even happened that liveperson with all these, activists and the board and all these people and who cares? I mean, who really cares? I mean, when you think about like in the scheme of things, like your kids look at you like.

I didn’t have a disease. know, I just was, ⁓ something happened. So they have to understand like it is what it is. Move forward, rebuild, keep, keep, nobody can take from you what you have, which is your ability to create, build and move forward. And that’s what I wanted to show them, you know, so.

Kevin Rice (48:40)
Mm-hmm.

Yeah,

absolutely. I think you’re right. Like they say more is caught than taught and your kids have this opportunity to see you rebuild, get back up, start something new. And I imagine something that you’re probably even more passionate about today. just based on the way you talked about this versus, you know, building a software company. So let’s move forward to today and you’re building something completely different.

⁓ you could have just gone back and started another software company because that’s like what you’ve done. That’s what you’ve known, but you’re building consumer product company in the ice AI. You’re building a consumer products company in the AI space for kids. What was the like inspiration to do to go down this new path?

Robert LoCascio (49:39)
Yeah, I mean the inspiration was really my kids and watching them with my with these devices, my iPhone and iPad and watching them really become like addicts to the device and you read about it, you hear about it. But once you become a parent and you see it.

It’s very troubling. then they’re being exposed to content through YouTube and YouTube Kids. That’s like giving my kids a different value set. Like my four-year-old says the F word because he saw it on something on YouTube. what they do on YouTube, especially YouTube Kids, is they make everything funny. So like if I hit you in the head with a baseball bat and I’m laughing and you’re laughing, it’s kind of funny.

But the kid thinks, and the kid will look at that and go, if I hit somebody, that’s funny.

Kevin Rice (50:24)
Right. But in real life, it’s not funny.

Robert LoCascio (50:32)
That’s a funny thing. And they don’t know any better. I started to see these things and I said, look, AI is a, it’s a, we know it’s transformate, it’s transformative. And for children, it could be really powerful if it’s provided to them in a way that truly is safe and empowers their creativity, like allows them to like take things out of their imagination, like make a image, make art, make a, a story, talk to characters, make a character.

So I have this whole thing like, you know, there’s a whole world out there that I think children can create content now, even as a four year old, that could be amazing. Like my four year old, if I give him video, an AI video model can make a pretty good 30 second film. You know, so like that’s cool. That’s Disney times a thousand. That’s like, if Walt was around, he’d be like,

It’s not about me finding the best animators, but about me finding the best kids to now power their imaginations through these amazing tools, which are built out of models.

Kevin Rice (51:28)
BLEH

Yes.

Tell us for anybody who’s not familiar with the product, what it does, like what’s your vision for it?

Robert LoCascio (51:40)
So it’s a device, it’s called KID, Keep it Dreaming. It has characters and in the middle you can make images and stories and buddies and music all by talking to the device. It also has a whole educational area where kids can get their own AI tutors and lessons and all of that.

So it’s really packed with all the power that AI could give a child to be their best creative self. Like I could just say, like, you know, I can talk to a character here. Let’s talk to one of the characters. This is Frost. Okay. He’s coming up. I’m dialing. I have to call Frost. I’m calling Frost. Okay. There he is. He’s like my little wolf. Hear the call of the mountain, little one.

I am Frost and the ancient paths know my tread. Frost, I’m here with Kevin and we’re talking about having a family and being an entrepreneur. What advice would you give on that? Although this is for my six-year-old, excuse me, this is my four-year-old Lorenzo. Hello Lorenzo. He’s Lorenzo by That’s a big and wonderful thing to think about. Having a family is like caring for a little forest.

Kevin Rice (52:41)
Sure, yeah.

Okay.

Robert LoCascio (52:51)
watching it grow and making it strong. Being an entrepreneur is like being a brave explorer, finding new paths. My advice is to be patient and kind, just like you take care of the mountain. Listen carefully to your family and what life is. So, yeah, so you feel like, and if I get it, like what’s cool about it, if I said, well, if I went to a space like somebody, my best friend was really mean to me.

Kevin Rice (53:08)
Beautiful. That’s so fun.

Robert LoCascio (53:20)
So it’s built for kids. it’ll off. It’s also about connecting with parents. Like part of the, like, say, well, why don’t you talk to your mom and dad about this? And it’s not all about tech. It’s about, I call building the bond back from kids and parents with devices. Like a lot of times it’s about get your mom here, dad, or whoever’s in your life. And why don’t we create something together? So it’s not all to be alone in a corner. So.

Kevin Rice (53:22)
Yeah.

Yeah.

I love that it kind of pushes you back to connection with your parents because other AI models that are available are really designed to create attachment with the individual and they’re designed to keep you really communicating with that model. And we’ve had some like tragic stories as a result of that. And so this is, that’s an awesome example of being able to like use this technology for creativity and imagination.

but also tying back into the whole family dynamic.

Robert LoCascio (54:16)
Yeah, cause we’re and I think it’s it’s look. It’s a reset right now. We have about 400 families that are going live with it, which is really interesting. I’m watching the statistics of what’s being used. I’m talking to the families and it’s just fascinating because it’s a different type of thing. Normally we’re used to handing a device. The kids run away. We’re like, you know, you take the device back. The reason I wanted to do a device so the kids could have their own thing. I think it’s like their own little world.

take it in their room, you don’t have to worry about it, but they don’t have to be hijacking your phone and then you kind of rip it back. So there’s something of sense of ownership to it, but then it’s part of this overall connection experience with the family. That’s my goal.

Kevin Rice (55:00)
Yeah.

I mean, you’ve been in the AI space for a while now. And I’m curious, like, do you have specific boundaries or guardrails around e-safety? Do you have advice that you could share with other parents when they’re thinking about how to expose their kids to AI and tech, but not exposing them to some of those potentially harmful platforms and channels?

Robert LoCascio (55:27)
It’s the reason I created the KID because I found that.

Yeah, you can try different things, but it’s almost like you’re crossing your fingers because they’re adult models and they can hallucinate. they can say weird things. they could make weird imagery. I just think, you know, I didn’t see it. So I felt like there, there isn’t someone who really took the care and time to just create an AI only, experience for just kids. They most time using these big models and trying to, trying to kind of get them down to be semi good. But, you you.

You have to construct them in a certain way. For instance, if a kid says I’m having an issue, it’ll off-ramp them. And even if they say it’s, I’m afraid of mom and dad, then it puts them back into, why don’t you go to a teacher? Go to school. it tries to find a path versus those models are kind of always trying to just tell you how great you are and to go, you know, like take you down. That’s where we see kids that have problems with them, eventually because they could hurt themselves and these AIs could help them do that. So.

Kevin Rice (56:13)
you

Yeah.

Robert LoCascio (56:27)
I think it’s challenging, so that’s why I want to create something.

Kevin Rice (56:33)
Yeah, amazing. Well, I love the product and looking forward to getting some for my children. And I wish you like the most success with it. ⁓ Cause I think, you know, you are starting over in some respects, but you’re also starting from a lot of experience and a lot of, you know, networking connections and probably a lot more passion this time around. So I’m just excited to see where you take it.

Robert LoCascio (56:55)
Yeah, it’s it’s been a great experience. I think it’s also I started another company called UareAI. So have two companies simultaneously, one for adults and AI and this one. And and it’s exciting. You know, the the moral to the story is. You know, no matter where you are in your career, your life, you just got to as Winston Churchill, Winston Churchill said, never, never quit and

just keep moving forward and there are no, you know, deck of cards That’s perfect. I remember someone told me once that there’s 52, you know, cards in a deck and each one represents different life that you could have. One is your, your, your, you’ve got cancer. One is you’re living in some place in the world that, that you potentially could get killed. There’s another one. You’ve got your life. One is you’re a billionaire and you’re living a life of a multi-billionaire.

would you want to put your card back in there and pick one out and take that risk? And I think the majority of people would say, no, like I won’t, my life’s good enough. I have the things I need. And there’s a lot more people that are suffering in the world that, you know, that we know are out there. so with that knowledge,

you kind of just have to, you you make him, you keep moving forward.

Kevin Rice (58:20)
Yeah. Last question and I’ll let you go here. A lot of our audience are kind of up and coming executives. You know, they’re aspiring to be in the position you were in leading a large organization and an executive role. If you look back on your career, is there any advice that you would give to them or like even your younger self as you were starting out?

Robert LoCascio (58:43)
Yeah, I would say,

people talk about this like imposter syndrome, you know, this saying, right? It’s like, and I would kind of ref, I would reframe that a little bit. And what that means that you don’t think you’re the right person for the job. You don’t think you’re good enough. You’re not smart enough. Not ready. You know, right. That’s, that’s that thing. And, and I, I would, kind of would reframe it a little bit. And to say that when you have that feeling, it’s really like,

Kevin Rice (58:56)
You don’t think you’re ready.

Robert LoCascio (59:09)
It’s like your inner child. Like you have the ability to like tap into that thing that’s a child. And that’s what it is. When we start something new, we’re like a child. We’re like back into our child self. And at one point that’s so exciting and it’s creative and it’s that excitement, you know, like my kids, run everywhere.

My kids don’t walk anywhere. They just sprint everywhere. I don’t know how they do it. They sprint two feet, 10 feet. They just have to sprint all the time. they, I saw my daughter, she’s like, you know, they skip, they skip and they make sounds when they walk. Like it’s the funniest thing because you realize I don’t skip anymore.

I don’t bolt someplace to go, but they’re always in that energy of like a kid. and so that feeling, you can look at it a very negative way, or you can look at it as that’s your inner child. That’s that piece. That’s that part that can be so fun and so scary. And that thing where kids at night, they think the darkness can hurt them, you know, like, but we don’t anymore as adults. And think of it like that. It’s it’s a beautiful thing. Not it’s the imposter. It’s it’s the you it’s it’s your child. It’s your inner

child and that’s the part that gives us our like fuel like that’s what can keep you around to volunteer hundreds that’s what can keep you in the game being older that’s what keeps you you know like alive and and look at it like that then I’m not I’m the child I’m a child because I don’t know things you’re the child that has a new way to look at everything that’s the cool

Kevin Rice (1:00:19)
Yeah.

Yeah.

I think

if you if you don’t have at least some level of imposter syndrome, you’re not challenging yourself enough You’re getting complacent because that just means that you are pushing yourself and you’re a little uncomfortable and So I think it’s probably good to have a little bit of imposter syndrome Otherwise, maybe you’re not growing as fast as you should and you’re not putting your self in a position to grow

Robert LoCascio (1:01:03)
That’s correct. That’s it. As we say, you know, if you, everything was just like, you know, I often say like, nobody has a, like a, ⁓ a mission statement that says, I want to be comfortable. My mission statement is to be comfortable. You know, like think of that. Like, I mean, I know some of you like probably like that. I just, I just want to be comfortable. No, no. Do you really want to be like comfortable is like being in a pool that feels like you’re in that weird.

Kevin Rice (1:01:18)
Right.

Robert LoCascio (1:01:32)
water that feels like urine maybe, you know what saying? Like that’s comfortable, you know what I’m saying? Like it’s that lukey warm feeling that doesn’t quite do it. It’s not too hot, not too cold. Nobody wants the lukey warm life. Lukewarm life, comfort, like aspiring for comfort is asking for trouble because the power to be out there, whoever that is, is gonna like kick you out of that zone pretty quick and put you in a place of feeling like, ⁓ back to your inner child.

Back to the uncertainty.

Kevin Rice (1:02:02)
Absolutely.

Rob, thank you so much for being here today. I really appreciated how you candidly shared your experience of building a company, losing it, and then building something new. And you are on this incredible hero’s journey. And I’m going to be looking forward to seeing where you take these next two companies.

Robert LoCascio (1:02:25)
Thank you. Thanks a lot, Kevin. I appreciate it.

Kevin Rice (1:02:27)
All right, I’m gonna

Learn About the Guest

Rob LoCascio, CEO & Founder KidAI

Rob LoCascio is the founder of LivePerson and a pioneer of internet-era customer communication, credited with inventing web chat. He took LivePerson public in 2000 and led the company for nearly 30 years, growing it to a peak market capitalization of over $6 billion. Today, Rob is the founder of KID, a kid-first AI product designed to empower creativity, ensure safety, and strengthen family connection. He is also a father of three and a lifelong builder focused on integrity, imagination, and impact.