Rick Elias is the CEO and co-founder of Red Ventures, a global investment platform with a portfolio including Lonely Planet, The Points Guy, Bankrate, and investments across multiple industries. He co-founded the company in January 2000 with Dan Feldstein after working together at CUC International.

The conversation explores Red Ventures' evolution from a near-death experience with $117,000 remaining in November 2000 to becoming a multi-billion dollar operating platform. Rick discusses the company's unique permanent capital structure with investors General Atlantic and Silver Lake, allowing them to invest in long-term culture and capabilities.

Beyond business strategy, Rick shares profound insights from surviving the Hudson River plane crash in seat 1D, his philosophy on distinguishing between living 'good' versus 'well,' and his recent venture into basketball team ownership in Puerto Rico. The discussion covers his views on money, leadership, forgiveness, and designing a life of purpose after achieving financial success.

From Near-Death to Billion-Dollar Acquisitions

Red Ventures started in January 2000 with $2 million raised from business school friends, but by November had only $117,000 left with no revenue - "I will never attend my reunions because all the capital came out of my business school friends"

The breakthrough came in 2004-2006 when Google became "the de facto aggregator of intent" and brands needed help defending themselves in the new customer acquisition landscape

Their value proposition was simple: "we can out-convert whatever you're doing by 30%. If that's not true, don't pay us. But if it is, don't pay us as an agency - pay us as a partner"

Bankrate was their first major acquisition at $1.4 billion, including creditcards.com, The Points Guy, and other financial services assets - "our first, okay, we're in the big leagues now"

The Hudson River Plane Crash: 90 Seconds of Clarity

Rick was in seat 1D when Captain Sully announced "brace for impact" - "the greatest gift one can get is to know that you're going to die" with 90 seconds to say goodbye

The experience revealed three key realizations: living with intense purpose daily, embarrassment at how much ego controlled his identity, and sadness at missing his opportunity to leave his mark

"I am going to try my very best every day to not regret not doing or saying something" became his guiding principle for living "out loud"

The crash led to profound forgiveness of himself: "I let go of all guilt. Not that I don't take responsibility, but the forgiveness happened to myself at the moment"

Living Good vs. Living Well: A Philosophy of Being

Rick distinguishes between "good" (external circumstances) and "well" (internal state): "things were not good, they were horrible, but I felt well because I was dealing with circumstances in the best way I could"

Well-being combines two concepts: "well is how you show up" and "being is a place where there's nothing to do, where you're doing things for no reason at all"

Society rewards "doing" through accomplishments and to-do lists, but "being" requires suspending "all the societal bullshit that manipulates the way we think the world wants us to show up"

His goal is to "die peacefully understanding that I became super clear on how to live life the way my soul was intended to live"

Puerto Rico Basketball: Culture Transforms Performance

After Hurricane Maria, Rick created Forward 787 movement, establishing five companies in Puerto Rico with "hundreds of employees" paying U.S. salaries to help rebuild the island

The basketball team purchase was initially reluctant - "I need one more thing like I need a root canal" - but became "the greatest toy" he'd ever owned as an adult

The team went from never making playoffs and being ranked 12th out of 12 teams to reaching game seven of the finals in one season

Three simple rules transformed the culture: "we are going to invest in you so you can make more money," focus on systems not goals, and "nobody is above the team"

"Culture is what you tolerate, not what you preach" - they fired a big free agent signing within days for being "a jerk" and suspended their best player for poor behavior

Money, Health, and the Pursuit of Enough

"After a certain amount of money, it doesn't really affect your lifestyle. At some point, it affects how people treat you and it affects your kids"

Rick lost 50 pounds over 10 years ("five pounds a year") and emphasizes health optimization, referencing his friendship with Peter Attia around aging well

He's stopped pursuing capital compounding: "I don't invest in funds anymore. I want to use my capital to compound other things that matter to me"

Energy management has replaced time management: "I only want to invest my energy in things that give me multiple currencies back"

Red Ventures Operating Philosophy and Future

The company operates as "an operating private equity platform with permanent capital" across 15 companies in Europe, Brazil, Puerto Rico, and the U.S.

Their competitive advantage: "we have never competed against anybody. We always competed against the fear of something" with focus on incremental performance compounding

Core investment criteria: understand the seller's true motivation, prefer businesses where "you can win in multiple ways," and never retrade deals once agreed

The healthcare joint venture with United Healthcare aims to build the "consumer-driven, consumer-led" healthcare company of the future with AI-powered personalized health agents