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

Shownote

Ric Elias - The Art of Living Well - [Invest Like The Best, CLASSICS] 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. Ric Elias [https://x.com/RicElias] 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 the business in 2000 and has grown it to now a global company with thousands of employees. Ric walks us through the early struggles that have led to what is now a flourishing investing 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 very moving. Please enjoy my conversation with Ric Elias. For the full show notes, transcript, and links to mentioned content, check out the episode page here. [https://joincolossus.com/episode/ric-elias-the-art-of-living-well/] ----- This episode is brought to you by WorkOS [https://workos.com/]. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. With a single API, developers can implement essential enterprise capabilities that typically require months of engineering work. By handling the complex infrastructure of enterprise features, WorkOS allows developers to focus on their core product while meeting the security and compliance requirements of Fortune 500 companies. Visit WorkOS [https://workos.com/] to Transform your application into an enterprise-ready solution in minutes, not months. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes [http://joincolossus.com/episodes].  Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here [https://joincolossus.com/]. Follow us on Twitter: @patrick_oshag [https://x.com/patrick_oshag] | @joincolossus [https://x.com/joincolossus] ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com [https://thepodcastconsultant.com/]). Timestamps: (00:00:00) Welcome to Invest Like the Best (00:02:00) Meet Ric Elias (00:02:49) Chasing the Big Dream (00:05:38) Understanding Red Ventures: Origin and Evolution (00:10:25) Operational Success and Company Culture (00:25:30) Reflections on Money and Personal Well-being (00:28:49) The Difference between Good and Well (00:32:55) The Hudson River Plane Crash Experience (00:42:37) Reconnecting with Puerto Rico and Reviving the Basketball Team (00:45:07) Underdogs to Champions (00:48:09) How to Build Trust and Culture (00:52:29) Reflections on Leadership (00:56:12) The Role of Confidence and Courage (00:59:38) The Value of Family and Friendships (01:01:57) The Pursuit of Purpose Over Profit (01:06:52) Recruitment and Company Culture (01:10:07) Reflecting on Success (01:14:33) The Importance of Pace and Speed (01:16:23) Other Business Philosophies (01:23:17) The Kindest Thing

Highlights

This conversation dives into the profound intersection of personal transformation, leadership, and purpose-driven growth, exploring how life-altering experiences can reshape one’s values and ambitions. Far from a conventional business narrative, it traces a journey marked by resilience, introspection, and the pursuit of meaning beyond material success.
03:15
Ric Elias's personal dream is internal well-being and lifelong satisfaction.
05:38
They raised $2 million with a flawed business plan but persevered through hustle and reinvention.
24:46
We'd rather pay more and never re-trade — keeping your word is essential in business.
25:31
Energy is more important than time—invest it where it returns value
31:22
Crisis reveals true connection to self and appreciation for daily experiences
38:02
The plane crash taught me to let go of ego and live with purpose.
42:38
Committed to moving Puerto Ricans back, creating employment, and paying U.S. salaries.
47:14
The team reaches game seven of the finals after being considered an easy opponent
50:32
Firing a free-agent for bad behavior to protect team culture
52:29
Leadership starts with personal leadership and owning your imperfections.
57:30
At Harvard, I realized I could compete at any level.
59:39
Ric realized he wanted to make his parents proud and do business ethically like his grandfather
1:01:58
They've stopped compounding capital and instead use it in Puerto Rico for meaningful pursuits.
1:09:24
One should be confident in one variable and have visibility on the other to manage investment risk.
1:12:36
The North Star is to give consumers all health-related answers, connectivity, and access through a personal health agent powered by AI.
1:14:33
Growth should be sustainable; unsustainable speed leads to burnout.
1:21:49
AI will disrupt all aspects of work and life in unpredictable ways

Chapters

Welcome to Invest Like the Best
00:00
Meet Ric Elias
02:00
Chasing the Big Dream
02:49
Understanding Red Ventures: Origin and Evolution
05:38
Operational Success and Company Culture
10:25
Reflections on Money and Personal Well-being
25:30
The Difference between Good and Well
28:49
The Hudson River Plane Crash Experience
32:55
Reconnecting with Puerto Rico and Reviving the Basketball Team
42:37
Underdogs to Champions
45:07
How to Build Trust and Culture
48:09
Reflections on Leadership
52:29
The Role of Confidence and Courage
56:12
The Value of Family and Friendships
59:38
The Pursuit of Purpose Over Profit
1:01:57
Recruitment and Company Culture
1:06:52
Reflecting on Success
1:10:07
The Importance of Pace and Speed
1:14:33
Other Business Philosophies
1:16:23
The Kindest Thing
1:23:17

Transcript

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