Please tell us a little bit about your business — what is your company all about?
Uare.ai is an Individual AI platform built on a simple but radical idea: AI should belong to you. Not to a company. Not to a data center training on your life without your consent. To you. We built something called the Human Life Model. It captures your voice, expertise, decision-making style, stories, and values across seven dimensions. Then it works for you the way only you would. We call it Authentic, not Artificial. Everyone is building AI for enterprises and teams. We’re building it for the person.
Tell us briefly about your background and how you started your company.
I got laid off from my first job out of Loyola University Maryland and decided that day to never work for anyone but myself again. In 1991, I started my first company, Sybarite Media, building interactive kiosks. It failed in 1995. With $5,000 left to my name, I started LivePerson out of a sublease office in lower Manhattan. I slept on a couch there for two years because I couldn’t afford both an office and an apartment. I chose the office because psychologically, I refused to feel like a failure twice.
In 1997, I invented web chat for customer support. The patent is US6519628B1. We took LivePerson public in April 2000, right before the dot-com crash. Stock fell to $0.07 in 2001, then it rose to $70 in 2021. Fast Company named us the world’s number one AI company in 2022, ahead of OpenAI. I ran it for 28 years. Then I started over, moved to Los Altos, California, and built Uare.ai out of my startup office here.
What are the top 3 skills needed to be a successful entrepreneur, and why?
Resilience is key. The real kind, where you’re left with $5,000 in your bank account after your first company just went under and you still get out of bed and start again. The couch years at LivePerson taught me that the people who win are those who refuse to quit on their darkest day.
Belief before proof matters. The stock fell to $0.07. Analysts were writing us off. Competitors were better funded. None of that mattered if I stopped believing before the market caught up. You have to hold the vision alone sometimes, for a long time, before the world sees what you see.
Curiosity that never turns off. Every pivot at LivePerson, from chat to messaging to AI, came from staying genuinely curious about what people needed next. The moment you think you know everything is the moment someone builds the thing that makes you irrelevant.
What are your plans for the future, and how do you plan to grow this company?
The vision is hundreds of millions of Individual AIs. Every expert, creator, entrepreneur, teacher, doctor, and founder owns their own AI that reflects who they actually are. We’re building the infrastructure for that. Right now, we’re in beta, growing with professionals and creators who want to scale without losing what makes them unique. The July launch of the Individual AI of His Holiness the Dalai Lama is one of our anchor moments. And we’re building toward enterprise use cases for executives who want their expertise accessible across their organizations. You can learn more at Uare.ai.
How did the pandemic impact your business, and do you feel like you have completely exited
the other side?
LivePerson actually accelerated during COVID. Brands had to go digital overnight, and conversational AI was suddenly mission-critical. What the pandemic did personally was force a kind of stillness I hadn’t made space for. It changed how I thought about what I was actually building and why. The real exit I’m still working through is the one that came after: leaving a company I ran for 28 years. That transition is its own journey. But building Uare.ai from scratch is the healthiest thing I’ve done professionally. Starting over, for real, has a clarity to it that running an established company never does.
How do you separate yourself from your competitors?
Everyone else is aggregating human knowledge into giant models trained on everything without consent. We inverted the model completely. At Uare.ai, one person’s data flows inward, and the value flows back to that same person. You own your AI. You control what it knows and who can access it. The data isn’t pooled, averaged, or diluted. That’s not just a product difference; it’s a philosophical one. Authentic, not Artificial, isn’t marketing. It’s the architecture.
What were the top three mistakes you made starting your business, and what did you learn from
them?
Trusting the wrong people with equity. I gave early ownership to people who didn’t share the long-term vision. When times got tough, their self-interest drove their decisions. Lesson: equity is trust made permanent. Only extend it to people you’d want in the foxhole with you for ten years minimum.
Letting the stock price drive my mood. We went from $8 to $0.07. I let that shake me more than it should have. The stock has no memory. The business does. I spent too much early energy managing perception instead of product.
Not hiring for will, only for skill. Skills you can train. Will you can’t.
Tell us a little bit about your marketing process; what has been the most successful form of
marketing for you?
Honest storytelling. Always. The post about sleeping on my office couch for two years at LivePerson reached more people than any ad campaign we ever ran. When I share something real — a real failure, a real number, a real moment — it lands. People are saturated with polish. What they actually respond to is a person talking directly to them like a human being. My LinkedIn is where I do most of that. The Over the Wall podcast series is another channel. Authentic beats manufactured every time.
What have been your biggest challenges, and how did you overcome them?
The dot-com crash was the first real test. We went public in April 2000, one of the last companies to go public by IPO before the market collapsed. We had to cut staff, cut expenses, and convince a company worth almost nothing that it had a future. I overcame it by refusing to let it be the end of the story. Stubbornness has real strategic value sometimes.
The bigger one was being removed from the company I founded after 28 years, through an activist-shareholder takeover. That one goes deep. Your identity gets tangled up in something you built for that long. The way through was starting something new. Building again. Moving to Los Altos with nothing but a vision for what Uare.ai could be.
What are you learning now? Why is that important?
I am learning how to build a company in the AI era where the rules are unlike anything I’ve done before. The speed is different, the tools are different, the distribution is different. I’m also learning what it means to build something that is genuinely for the individual rather than for enterprise revenue. And personally, I’m in the middle of a year of the Spiritual Exercises of Saint Ignatius. That’s teaching me more about discernment than anything else I’ve ever done. Knowing the difference between my own fear and actual truth. That matters everywhere, not just in spirituality.
If you started your business again, what things would you do differently?
I would have set clearer boundaries between investors and operators earlier. The people who put in money and the people who build the thing have fundamentally different time horizons and risk tolerances. When you let those two groups blur, eventually the mismatch becomes a problem. I’d also have taken more creative risks earlier. The moments at LivePerson I’m most proud of were when we went against conventional wisdom. I should have done that more and sooner.
What are the top 3 online tools and resources you use to grow your company?
Uare.ai obviously. My own Individual AI is how I communicate, scale my thinking, and show the product working in real life. I use it every day.
Claude for AI operations. Running marketing campaigns, drafting content, working through complex problems at speed. It’s the engine behind a lot of how we actually operate day to day.
Notion for everything shared. All our docs, conversations, and team knowledge live there. It’s the connective tissue of the company.
What’s a productivity tip you swear by?
Make one decision before 9 AM that you’ve been avoiding. The avoidance costs more energy than the decision ever would. Every day I delay something hard, it gets heavier. The moment I address it, it shrinks. Do the hard thing first.
Can you recommend one book, one podcast, and one online course for entrepreneurs?
Book: Man’s Search for Meaning by Viktor Frankl. It’s not a business book. That’s why it’s the most important one. If you can find meaning in the worst circumstances imaginable, you can run a company through anything.
Podcast: Over the Wall with Rob LoCascio. I built it because I wasn’t finding the honest conversations about entrepreneurship I wanted to have. Every guest goes somewhere real.
Course: Skip the courses. Find a mentor who has built something and failed. Failure is the only curriculum that actually prepares you.
What is your favorite quote?
“I would rather be ashes than dust. I would rather that my spark should burn out in a brilliant blaze than it should be stifled by dry-rot. I would rather be a superb meteor, every atom of me in magnificent glow, than a sleepy and permanent planet. The function of man is to live, not to exist. I shall not waste my days trying to prolong them. I shall use my time.” – Jack London
What valuable advice would you give new entrepreneurs starting out?
Don’t quit on your darkest day. Everyone has a couch moment. That period where you stare into the abyss with no clarity about what comes next. I literally slept on mine for two years in a Lower Manhattan office with $5,000 in the bank. The couch is not the end. It’s where you find out who you actually are. Keep going.
What is your definition of success?
Building something that mattered. Not a number. Not a stock price. I took a company from $0.07 to $70 per share. Neither of those things defined the company. What defined it was the work we did in between. Success for me is waking up every day, building something I believe in, with people I respect, toward something that actually improves someone’s life. Right now, with Uare.ai, that’s the clearest I’ve ever been about that.
How do you personally overcome fear?
I learned this from thirty years of building and from the Spiritual Exercises. Fear is almost always False Evidence Appearing Real. It tells you a story about what will happen if you move forward. That story is almost never accurate. The practice is to catch yourself in the fear, name it, and ask: is this God’s voice or is this just noise? God would never speak in a defeatist way. So when I hear that voice saying I can’t do something, I’ve learned it’s not a signal to stop. It’s just a test.
How can readers get in touch with you?
Connect with me on LinkedIn or come find my Individual AI and everything we’re building at Uare.ai. I’m also on the Over the Wall podcast if you want to go deeper.
**Readers and listeners interested in exploring an Individual AI can chat with my Individual AI. Here’s Rob’s Individual AI.**