Ric Elias - The Art of Living Well - [Invest Like The Best, CLASSICS]
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
This masterclass conversation with Red Ventures CEO Ric Elias explores the intersection of business success and personal fulfillment. Ric shares his journey from near-bankruptcy startup founder to building a multi-billion dollar digital platform company, while maintaining focus on culture, purpose, and well-being. (02:49) The episode centers on profound personal lessons learned from surviving the "Miracle on the Hudson" plane crash, which fundamentally shifted his perspective on life, leadership, and what truly matters. (32:55)
- Core themes include the evolution from "doing" to "being," the difference between living "good" versus living "well," and how to build sustainable business culture that outlasts individual leaders.
Speakers
Ric Elias
Ric Elias is the CEO and co-founder of Red Ventures, a digital platform company with a portfolio including Lonely Planet, The Points Guy, and Bankrate. He started the company in 2000 and has grown it from near-bankruptcy with $117,000 remaining to a multi-billion dollar global operation with thousands of employees. Ric is also a survivor of the "Miracle on the Hudson" plane crash and has given a widely-viewed TED Talk about the experience.
Patrick O'Shaughnessy
Patrick O'Shaughnessy is the CEO of Positive Sum and host of the "Invest Like the Best" podcast. He conducts in-depth conversations with successful entrepreneurs, investors, and thought leaders, focusing on strategies for better investing both time and money.
Key Takeaways
Build Culture as Your Competitive Advantage
Ric emphasizes that Red Ventures' success stems from using culture as "connective tissue" across portfolio companies. (10:25) Rather than teaching values, they share beliefs and hire people who resonate with them. This cultural alignment allows them to extract synergies that traditional private equity can't achieve because their companies aren't connected at the tech or cultural layer like Red Ventures is. The key insight is that culture isn't what you preach—it's what you tolerate, as demonstrated when they fired their best basketball player for not embodying team-first values.
Focus on Permanent Capital and Patient Thinking
One of Red Ventures' strategic advantages is operating with permanent capital, meaning no forced exit timeline. (13:40) This structure, achieved by not needing outside investment until 2010, gives them license to invest in things others wouldn't. They can focus on long-term value creation rather than meeting investor exit schedules. For professionals, this translates to building financial independence that allows for patient decision-making rather than being forced into short-term thinking due to financial pressure.
Understand the Difference Between "Good" and "Well"
Ric draws a crucial distinction between external circumstances being "good" versus internal well-being. (28:54) "Good" reflects what's happening in the world around you, while "well" is an internal state of peace and purpose that exists regardless of external circumstances. He discovered this during personal difficulties when things weren't good but he felt well because he was dealing with challenges in the best way possible. This mindset shift helps professionals maintain resilience and perspective during difficult periods.
Forgiveness as a Leadership and Life Philosophy
After surviving the Hudson River plane crash, Ric learned that forgiveness—especially forgiving without receiving an apology—becomes a source of tremendous personal freedom. (39:38) This applies both to forgiving others and forgiving yourself. When you develop self-forgiveness, you become kinder in your internal dialogue and naturally extend that grace to others. For leaders, this creates psychological safety and stronger relationships because people feel accepted for their humanity rather than judged for their mistakes.
Invest Energy Strategically, Not Just Time
Beyond time management, Ric focuses on energy management as the higher-level currency. (27:24) He only invests energy in relationships and activities that give him multiple currencies back—whether that's growth, connection, or purpose. If someone drains his energy, he actively avoids future interactions. If someone energizes him, he leans into that relationship. This approach helps professionals be more selective about commitments and focus on activities that genuinely fuel rather than deplete them.
Statistics & Facts
- Red Ventures was down to $117,000 with no revenue by November 2000, just months after raising $2 million from friends. (07:27) This near-death experience shaped their bootstrap mentality and relentless focus on survival.
- The company didn't raise outside capital until 2010—a full decade of bootstrapping—and when they finally did raise money, they didn't actually need it for operations but did it to provide employee liquidity. (13:40)
- Red Ventures' acquisition strategy typically improves performance from 10x multiples to 4x within two years through their operational capabilities and technology platform. (19:59)
