Ric Elias - The Art of Living Well

**Patrick O'Shaughnessy** (0:00)
Here's a puzzle. What do OpenAI, Cursor, Perplexity, Vercell, Plaid, and hundreds of other winning companies all have in common? The answer is that they're powered by today's sponsor, WorkOS. If you're building software for enterprises, you probably felt the pain of integrating SSO, SCIM, RBAC, audit logs, and other features required by big customers. WorkOS turns those deal blockers into drop-in APIs with a modern developer platform built specifically for B2B SaaS. Whether you're a seed stage startup trying to land your first enterprise customer or a unicorn expanding globally, WorkOS is the fastest path to becoming enterprise ready and unlock growth. It's essentially Stripe for enterprise features. Visit workos.com to get started or just hit up their Slack support. Yes, they have real engineers in there who will answer your questions fast. WorkOS allows you to build like the best with delightful APIs, comprehensive docs, and smooth developer experience. Go to workos.com to make your app enterprise ready today. Hello and welcome everyone. I'm Patrick O'Shaughnessy and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing. You can find Colossus Review along with all of our podcasts at joincolossus.com.

**SPEAKER_2** (1:23)
Patrick O'Shaughnessy is the CEO of PositiveSum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of PositiveSum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of PositiveSum may maintain positions in the securities discussed in this podcast. To learn more, visit p-s-u-m dot v-c.

**Patrick O'Shaughnessy** (1:52)
Welcome to this Classic episode. Classics are my favorite episodes from the past 10 years published once a month. These are N of One Conversations with N of One People. My guest today is Ric Elias. Ric is the CEO and co-founder of Red Ventures, which has a portfolio of fast growing digital businesses like Lonely Planet, The Points Guy, 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. Ric 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. Ric'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 Ric 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. 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. 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.

**Ric Elias** (3:33)
You cheated.

**Patrick O'Shaughnessy** (3:33)
So I'm using it and I cheated.

**Ric Elias** (3:35)
I like it.

**Patrick O'Shaughnessy** (3:36)
Carlos' question in mine is, what is the big dream?

**Ric Elias** (3:41)
My big dream is to live in a state of well-being 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.

**Patrick O'Shaughnessy** (3:59)
We're going to pick that apart in detail, but go down one level.

**Ric Elias** (4:03)
Sure.

**Patrick O'Shaughnessy** (4:04)
What is the Red Ventures big dream?

**Ric Elias** (4:07)
We've been on this journey for 24 years. Then 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.