Invest Like the Best with Patrick O'Shaughnessy
Ric Elias - The Art of Living Well - [Invest Like The Best, CLASSICS]
23 Dec 2025
Chapter 1: What is the main topic discussed in this episode?
Here's a puzzle.
Chapter 2: Who is Ric Elias and what does he do?
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Chapter 3: What challenges did Ric face in the early days of Red Ventures?
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Chapter 4: How does company culture influence operational success?
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Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people. My guest today is Rick Elias.
Rick is the CEO and co-founder of Red Ventures, which has a portfolio of fast-growing digital businesses like Lonely Planet, The Points Guide, Bankrate, and large investments in a variety of other businesses across industries. He began Red Ventures in the year 2000 and has grown it to a global company with thousands of employees.
Rick walks us through the early struggles that have led to a now flourishing investment platform. But mostly, this episode is a masterclass on cultural values and philosophies that transcend mere financial gain. We discuss the difference between living good and well, the power of forgiveness, and compounding more than just your capital.
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Chapter 5: What is the difference between living good and living well?
Rick's story is one of resilience, humility, and grace. His story about being in the front row of the plane that Captain Sully landed in the Hudson is singular and moving. Please enjoy this great conversation with Rick Elias.
So just before we came in here, you and I did something together on stage, and then I was talking to Carlos on your team, and he asked me whether or not and how I prepare for these things. And I told him the truth, which is that in some literal sense, I don't prepare. I don't sit down and think about them right ahead of them.
Chapter 6: What lessons can be learned from the Hudson River plane crash?
But in some other sense, I prepare all the time because I end up talking to people that I'm most interested by and curious about and have met before, usually like you and I have met before. And that the only thing I prepare is the first question. And I usually do that about five minutes ahead of time. But I hadn't done that.
And so I actually asked Carlos to give me the first question that I'll ask. This first one comes from Carlos, but I love it. You cheated. So I'm using it and I cheated. I like it. Carlos's question in mind is, what is the big dream?
Chapter 7: How does Ric reconnect with his Puerto Rican roots?
My big dream is to live in a state of wellbeing most of the time and to have a sense of lifelong satisfaction when the end comes. So it's really very internal versus something that gets accomplished or left behind. We're going to pick that apart in detail, but go down one level. Sure. What is the Red Ventures big dream? We've been on this journey for 24 years.
Chapter 8: What strategies does Ric use to build trust and culture in his teams?
And in one sense, it feels like we're about to go on another 10-year journey of reinventing ourselves. Red Ventures, over time, hopefully becomes a place where a lot of this... Whatever success we've had gets put back into the system. So more of a full circle versus a full line to the right or to the left or down. But I still think that we're years or decades away from that.
Can you tell us what it is? I ask that in the stupidest, simplest way I can for a reason, because it's pretty hard to figure out what it is from the outside. On purpose. I know on purpose, but I have to ask. Maybe the best way to ask is, how did it begin?
The easiest way to understand it at a high level, you can think of ourselves as a operating private equity platform with permanent capital, hyper-focused on the digital world with different business models.
under the belief that culture really matters and that if you use that as the connective tissue inside of the portfolio companies, you can get some level of alpha vis-a-vis these companies being separate.
And today we, depends on how you want to count, have about 15 different companies inside of the portfolio all over the place between Europe, Brazil, Puerto Rico, and then our core businesses here, inclusive of a big joint venture with UnitedHealthcare and so forth. So if we go back to the very beginning, something worked.
You and your team were awesome investors or trend spotters or operators or some combination of those things, probably maybe some luck sprinkled in, which is true for all of us. How did it start? What was the origin story? Look, I think we're more lucky than sprinkle luck. I've always believed that. And if I look back in our journey, Dan and I started this company in January 2000.
Dan and I worked together before this at a company called Sendin CUC. And we really started with two principles in mind. One was, let's build a company we will wanna work for. And Dan and I are not typical.
We're very different in hopefully good ways, but we both are of the same opinion that life is to be lived with enjoyment and that we will wanna work at a place or build a place that we will wanna go work every day so we never have to work. True definition of being an entrepreneur.
And then the second one, and I think we said it at the time without really understanding it, which was a company that would outlast us. And even though we would want to do this for a long time, Dan retired about a year ago, a company that would outlive us. What I have come to realize is it will outlive us through the people that get trained in our platform, not as a company itself.
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