Ric Elias - The Art of Living Well - [Invest Like The Best, CLASSICS] - Invest Like the Best with Patrick O'Shaughnessy

Invest Like the Best with Patrick O'Shaughnessy
Episode: Ric Elias – The Art of Living Well [CLASSICS]
Release Date: December 23, 2025

Episode Overview

This classic episode features Ric Elias, CEO and co-founder of Red Ventures, whose portfolio includes digital businesses like Lonely Planet, The Points Guy, and Bankrate. The conversation transcends typical investing and business success to explore deeper questions about purpose, well-being, forgiveness, cultural philosophy, and the art of living a meaningful life. Ric reflects on building an enduring company, surviving a near-death experience (the "Miracle on the Hudson" plane), lessons in leadership, community building, and his evolving views on success, energy, and happiness.

Key Discussion Points & Insights

1. Ric Elias’ "Big Dream" and Red Ventures’ Purpose

The Personal Dream: Ric’s main aspiration 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" (03:41).
Company Purpose: The vision for Red Ventures is less a linear outcome and more "a place where...success gets put back into the system, more of a full circle," focusing on people, culture, and reinvention, not just profits or legacy (04:07).

2. Red Ventures’ Origin & Unique DNA

Founding Principles: Ric and his partner Dan started with two principles: build a company they'd want to work for, and make one that would outlast them—not just as an entity, but through people (05:56).
Early Struggles: They survived the dot-com bust and almost ran out of money, paying investors back as soon as they could, emphasizing humility, adaptation, and relentless incremental improvement (05:56–09:33).
Cultural Success: The company grew not just through acquisitions but through a focused culture: "Our DNA is incredible operators, really good optimizers...maybe not as great at high-end product or experimentation" (10:58).

3. Culture as a Competitive Edge

Permanent Capital: The decision to remain private and work with patient capital (General Atlantic, Silver Lake) allowed a focus on culture and criteria beyond exit timelines (13:15).
Beliefs System: Red Ventures’ beliefs—literally written on the walls—are the connective tissue. "We can't teach you values...but we can tell you what we believe" (13:15).
Recent Challenges: Ric stresses the need to maintain hunger and growth mindsets as the company matures and operates from a position of relative success (15:23).

4. On Compounding, Incentives, and Success

Compounding Beyond Capital: "Compounding more than just your capital" is core to Ric’s philosophy—the operator mindset applies across domains (21:50, 22:52).
Incentive Structures: The reason Red Ventures remains unique is their incentives aren’t built around flipping companies, but creating lasting improvements: "Tell me how someone gets paid and I’ll tell you how they behave" (21:00).

5. Acquisitions and Operational Philosophy

Transformational Value: The Red Ventures method is to acquire under-optimized businesses and apply rigorous operational improvements—"If we bought at 10 times, within two years it was four times" (18:44, 19:28).
Acquisition Taste: Ric is highly tuned to the "motivation of the seller" and only partners if the chemistry and moral alignment are right (23:00).

Philosophy of Life, Money, and Growth

1. Money, Time, Energy, and the Pursuit of "Well"

Money’s Limits: "Money is a tricky thing because money corrupts society…" Ric believes chasing more for its own sake leads to missing out on life’s real journey (25:55).
Well vs. Good:
- "Even though things were not good, I felt well. I was dealing with all the circumstances in the best way I could..." (28:51–31:50).
Energy Management: Ric now optimizes for energy, not just time or money: "I just want good energy in my life" (27:46).

2. Impact of Near-Death Experience (Flight 1549)

The "Gift" of Knowing: Surviving the Hudson River landing catalyzed Ric’s life philosophy: "It's the greatest gift to know that you're going to die" (33:06).
Lessons From Crisis:
- Letting go of regret: “All changed in an instant… I am going to live with intense purpose every day. I am going to ask for forgiveness…” (36:31).
- Dismantling ego and guilt; learning deep forgiveness for himself and others: “True forgiveness...is when you forgive when the other person doesn’t apologize” (36:31–41:20).

Leadership, Community, and Culture

1. Leadership Evolution

Leadership isn’t a title; it's "something you earn." It starts with self-leadership—knowing and caring for oneself—then extends to others, embracing imperfection and humanity (53:02).

2. Community Projects and Civic Engagement

Ric describes redeveloping his relationship with Puerto Rico post-Hurricane Maria through Forward787, building companies and community impact: "I'm falling in love with the island because it's too small and you actually can do something" (42:44).
Basketball Team Project: He bought a moribund basketball team with friends—cultivating culture, not just winning—a microcosm for belonging and high-achieving teams: "Culture is what you tolerate, not what you preach" (49:41).

Practical Management and Investing Insights

1. Recruiting and Apprenticeship

Recruiting: Seeks team-focused, highly coachable talent over lone stars (67:10).
Apprenticeship: Stresses risk to traditional learning and growth with new hybrid work models; laments the loss of the “apprenticeship decade” (79:05).

2. Investment Philosophy

Ric loves betting where the odds are clear, not gambling—"Life is about understanding odds and edges" (68:56).
Risk evaluation: "If the business has three variables for it to work, I will never invest in it... If it has one variable and you have an inkling, lean right in" (68:56).

Notable Quotes & Memorable Moments

On Company Purpose: “Let’s build a company we would want to work for...so we never have to work” – Ric Elias (05:56)
On Well-Being: "Well-being is a place where you feel really settled inside...you suspend all this societal bullshit that we give so much power to..." (31:50)
On Near-Death Clarity: “It’s the greatest gift to know that you’re going to die” (33:06)
On Ego & Forgiveness: "True forgiveness...is when you forgive when the other person doesn’t apologize. Because the forgiveness comes from love" (41:18)
On Culture: “Culture is what you tolerate, not what you preach” (49:41)
On Pursuit of More: “Every time you get to a peak, you'll see higher peaks. There's nothing about a peak that matters” (62:18)
On Friendship: “You don’t ever let anybody else love you back. And you suck all the love out of every interaction because that’s how you feel good about yourself” (64:33)
On Kindness: "The grace that you give somebody when you forgive them is the most beautiful thing we do as humans" (83:23)

Timestamps for Key Segments

Start & "Big Dream": 03:41
Red Ventures’ Formation & Principles: 05:56–09:33
First Major Acquisition & Transformation Playbook: 09:38–19:28
Culture, Beliefs, and Permanent Capital: 13:15–15:18
Well vs. Good, Well-Being Philosophy: 28:51–31:50
Plane Crash Experience, Forgiveness, Ego: 33:06–41:18
Puerto Rico, Forward787, Basketball Team: 42:44–52:15
Leadership Lessons: 53:02–54:41
Money, Time, Energy: 25:55–27:46
Business & Investing Philosophy: 54:47–70:08
Society’s Mirage of More: 62:18
Recruiting, Apprenticeship, and Teaching Culture: 67:10–79:05
Looking Ahead, AI & Change: 82:02
The Kindest Thing: 83:23

Tone & Closing

Ric Elias’ tone throughout is deeply reflective, candid, and gentle, merging wisdom, humor, and humility. The episode offers both practical strategies for success and profound, personal philosophies for living — an inspiring listen for anyone seeking meaning in their work and life.

For more episodes, resources, and deep dives, visit JoinColossus.com.

Invest Like the Best with Patrick O'Shaughnessy
Episode: Ric Elias – The Art of Living Well [CLASSICS]
Release Date: December 23, 2025

Episode Overview

Key Discussion Points & Insights

1. Ric Elias’ "Big Dream" and Red Ventures’ Purpose

The Personal Dream: Ric’s main aspiration 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" (03:41).
Company Purpose: The vision for Red Ventures is less a linear outcome and more "a place where...success gets put back into the system, more of a full circle," focusing on people, culture, and reinvention, not just profits or legacy (04:07).

2. Red Ventures’ Origin & Unique DNA

Founding Principles: Ric and his partner Dan started with two principles: build a company they'd want to work for, and make one that would outlast them—not just as an entity, but through people (05:56).
Early Struggles: They survived the dot-com bust and almost ran out of money, paying investors back as soon as they could, emphasizing humility, adaptation, and relentless incremental improvement (05:56–09:33).
Cultural Success: The company grew not just through acquisitions but through a focused culture: "Our DNA is incredible operators, really good optimizers...maybe not as great at high-end product or experimentation" (10:58).

3. Culture as a Competitive Edge

Permanent Capital: The decision to remain private and work with patient capital (General Atlantic, Silver Lake) allowed a focus on culture and criteria beyond exit timelines (13:15).
Beliefs System: Red Ventures’ beliefs—literally written on the walls—are the connective tissue. "We can't teach you values...but we can tell you what we believe" (13:15).
Recent Challenges: Ric stresses the need to maintain hunger and growth mindsets as the company matures and operates from a position of relative success (15:23).

4. On Compounding, Incentives, and Success

Compounding Beyond Capital: "Compounding more than just your capital" is core to Ric’s philosophy—the operator mindset applies across domains (21:50, 22:52).
Incentive Structures: The reason Red Ventures remains unique is their incentives aren’t built around flipping companies, but creating lasting improvements: "Tell me how someone gets paid and I’ll tell you how they behave" (21:00).

5. Acquisitions and Operational Philosophy

Transformational Value: The Red Ventures method is to acquire under-optimized businesses and apply rigorous operational improvements—"If we bought at 10 times, within two years it was four times" (18:44, 19:28).
Acquisition Taste: Ric is highly tuned to the "motivation of the seller" and only partners if the chemistry and moral alignment are right (23:00).

Philosophy of Life, Money, and Growth

1. Money, Time, Energy, and the Pursuit of "Well"

Money’s Limits: "Money is a tricky thing because money corrupts society…" Ric believes chasing more for its own sake leads to missing out on life’s real journey (25:55).
Well vs. Good:
- "Even though things were not good, I felt well. I was dealing with all the circumstances in the best way I could..." (28:51–31:50).
Energy Management: Ric now optimizes for energy, not just time or money: "I just want good energy in my life" (27:46).

2. Impact of Near-Death Experience (Flight 1549)

The "Gift" of Knowing: Surviving the Hudson River landing catalyzed Ric’s life philosophy: "It's the greatest gift to know that you're going to die" (33:06).
Lessons From Crisis:
- Letting go of regret: “All changed in an instant… I am going to live with intense purpose every day. I am going to ask for forgiveness…” (36:31).
- Dismantling ego and guilt; learning deep forgiveness for himself and others: “True forgiveness...is when you forgive when the other person doesn’t apologize” (36:31–41:20).

Leadership, Community, and Culture

1. Leadership Evolution

Leadership isn’t a title; it's "something you earn." It starts with self-leadership—knowing and caring for oneself—then extends to others, embracing imperfection and humanity (53:02).

2. Community Projects and Civic Engagement

Ric describes redeveloping his relationship with Puerto Rico post-Hurricane Maria through Forward787, building companies and community impact: "I'm falling in love with the island because it's too small and you actually can do something" (42:44).
Basketball Team Project: He bought a moribund basketball team with friends—cultivating culture, not just winning—a microcosm for belonging and high-achieving teams: "Culture is what you tolerate, not what you preach" (49:41).

Practical Management and Investing Insights

1. Recruiting and Apprenticeship

Recruiting: Seeks team-focused, highly coachable talent over lone stars (67:10).
Apprenticeship: Stresses risk to traditional learning and growth with new hybrid work models; laments the loss of the “apprenticeship decade” (79:05).

2. Investment Philosophy

Ric loves betting where the odds are clear, not gambling—"Life is about understanding odds and edges" (68:56).
Risk evaluation: "If the business has three variables for it to work, I will never invest in it... If it has one variable and you have an inkling, lean right in" (68:56).

Notable Quotes & Memorable Moments

On Company Purpose: “Let’s build a company we would want to work for...so we never have to work” – Ric Elias (05:56)
On Well-Being: "Well-being is a place where you feel really settled inside...you suspend all this societal bullshit that we give so much power to..." (31:50)
On Near-Death Clarity: “It’s the greatest gift to know that you’re going to die” (33:06)
On Ego & Forgiveness: "True forgiveness...is when you forgive when the other person doesn’t apologize. Because the forgiveness comes from love" (41:18)
On Culture: “Culture is what you tolerate, not what you preach” (49:41)
On Pursuit of More: “Every time you get to a peak, you'll see higher peaks. There's nothing about a peak that matters” (62:18)
On Friendship: “You don’t ever let anybody else love you back. And you suck all the love out of every interaction because that’s how you feel good about yourself” (64:33)
On Kindness: "The grace that you give somebody when you forgive them is the most beautiful thing we do as humans" (83:23)

Timestamps for Key Segments

Start & "Big Dream": 03:41
Red Ventures’ Formation & Principles: 05:56–09:33
First Major Acquisition & Transformation Playbook: 09:38–19:28
Culture, Beliefs, and Permanent Capital: 13:15–15:18
Well vs. Good, Well-Being Philosophy: 28:51–31:50
Plane Crash Experience, Forgiveness, Ego: 33:06–41:18
Puerto Rico, Forward787, Basketball Team: 42:44–52:15
Leadership Lessons: 53:02–54:41
Money, Time, Energy: 25:55–27:46
Business & Investing Philosophy: 54:47–70:08
Society’s Mirage of More: 62:18
Recruiting, Apprenticeship, and Teaching Culture: 67:10–79:05
Looking Ahead, AI & Change: 82:02
The Kindest Thing: 83:23

Tone & Closing

For more episodes, resources, and deep dives, visit JoinColossus.com.

Ric Elias - The Art of Living Well - [Invest Like The Best, CLASSICS]

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Summary

Episode Overview

Key Discussion Points & Insights

1. Ric Elias’ "Big Dream" and Red Ventures’ Purpose

2. Red Ventures’ Origin & Unique DNA

3. Culture as a Competitive Edge

4. On Compounding, Incentives, and Success

5. Acquisitions and Operational Philosophy

Philosophy of Life, Money, and Growth

1. Money, Time, Energy, and the Pursuit of "Well"

2. Impact of Near-Death Experience (Flight 1549)

Leadership, Community, and Culture

1. Leadership Evolution

2. Community Projects and Civic Engagement

Practical Management and Investing Insights

1. Recruiting and Apprenticeship

2. Investment Philosophy

Notable Quotes & Memorable Moments

Timestamps for Key Segments

Tone & Closing

Summary

Episode Overview

Key Discussion Points & Insights

1. Ric Elias’ "Big Dream" and Red Ventures’ Purpose

2. Red Ventures’ Origin & Unique DNA

3. Culture as a Competitive Edge

4. On Compounding, Incentives, and Success

5. Acquisitions and Operational Philosophy

Philosophy of Life, Money, and Growth

1. Money, Time, Energy, and the Pursuit of "Well"

2. Impact of Near-Death Experience (Flight 1549)

Leadership, Community, and Culture

1. Leadership Evolution

2. Community Projects and Civic Engagement

Practical Management and Investing Insights

1. Recruiting and Apprenticeship

2. Investment Philosophy

Notable Quotes & Memorable Moments

Timestamps for Key Segments

Tone & Closing