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

Invest Like the Best with Patrick O'Shaughnessy

Colossus

Technology, Business, Investing

4.7 • 2.5K Ratings

🗓️ 23 December 2025

⏱️ 85 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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 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. ----- This episode is brought to you by WorkOS. 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 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. 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. Follow us on Twitter: @patrick_oshag | @joincolossus ----- Editing and post-production work for this episode was provided by The Podcast Consultant (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

Transcript

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0:00.0	Here's a puzzle. What do OpenAI, Cursor, Perplexity, Versal, Plaid, and hundreds of other winning companies all have in common?
0:07.1	The answer is that they're powered by today's sponsor, Work OS. If you're building software for enterprises, you probably felt the pain of integrating SSO,
0:15.3	skim, Rback, audit logs, and other features required by big customers. WorkOS turns those deal blockers into drop-in
0:22.0	APIs with a modern developer platform built specifically for B2B SaaS. Whether you're a seed
0:27.1	stage startup trying to land your first enterprise customer or a unicorn expanding globally,
0:31.9	WorkOS is the fastest path to becoming enterprise ready and unlock growth. It's essentially
0:36.6	stripe for enterprise features.
0:38.5	Visit workOS.com to get started or just hit up their Slack support.
0:42.6	Yes, they have real engineers in there who will answer your questions fast.
0:46.3	WorkOS allows you to build like the best with delightful APIs, comprehensive docs, and smooth developer experience.
0:51.9	Go to workOS.com to make your app enterprise ready today.
0:58.5	Hello and welcome everyone. I'm Patrick O'Shaughnessy and this is Invest Like the Best. This show is
1:03.1	an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest
1:07.9	both your time and your money. If you enjoy these conversations and want to go deeper,
1:11.7	check out Colossus Review, our quarterly publication with in-depth profiles of the people
1:16.1	shaping business and investing.
1:17.6	You can find Colossus Review along with all of our podcasts at join colossus.com.
1:23.7	Patrick O'Shaughnessy is the CEO of Positive Sum.
1:27.0	All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of Positive Some.
1:34.2	This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.
1:40.9	Clients of Positive Some may maintain positions in the securities discussed in this podcast.
1:46.0	To learn more, visit psum.vc.
	...

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