Mark Bertolini - Performance During Pain - [Invest Like the Best, EP.438]

Invest Like the Best with Patrick O'Shaughnessy

Colossus

Technology, Business, Investing

4.7 • 2.5K Ratings

🗓️ 19 August 2025

⏱️ 100 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

My guest today is Mark Bertolini. Mark is the former CEO of Aetna and the current CEO of Oscar Health. He shares one of the most extraordinary leadership stories I've encountered—surviving a catastrophic skiing accident that left him in chronic pain for 18 years while simultaneously leading one of healthcare's most successful corporate turnarounds. His personal experience navigating his son's life-threatening cancer battle and his own medical challenges fundamentally changed his approach to healthcare, leading to innovations in employee welfare that Wall Street initially questioned but ultimately celebrated. During his tenure at Aetna, Mark generated 652% total shareholder return by implementing revolutionary employee policies and is now applying these lessons at Oscar Health to disrupt the $4 trillion healthcare industry with a technology-first approach. We discuss the power of servant leadership, employer-sponsored insurance vs individual choice-based plans, and the horizons of healthcare. Please enjoy this incredible conversation with Mark Bertolini. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp.com/invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ridgelineapps.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about the platform. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠⁠⁠⁠⁠⁠. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠⁠⁠⁠⁠⁠⁠⁠⁠ Alpha-Sense.com/Invest⁠⁠⁠⁠⁠⁠⁠⁠⁠ and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:04:52) Mark's Ski Accident and Recovery (00:07:54) Early Life and Career Beginnings (00:12:51) Leadership Philosophy and Career Highlights (00:19:03) Healthcare System Insights and Innovations (00:25:31) Oscar Health: Current State and Future Vision (00:42:06) Personal Stories and Eastern Belief System (00:51:57) Discovering the Healing Power of Yoga (00:57:21) Transforming Employee Benefits and Wages (01:02:41) Personal Journey Through Chronic Pain (01:08:10) Reflections on Business Success and Leadership (01:15:54) Joining Bridgewater and Transitioning Leadership (01:22:47) Leading Oscar Health and Future Goals (01:34:12) Enduring Hardships and Finding Purpose (01:32:34) The Kindest Thing Anyone Has Ever Done For Mark

Transcript

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0:00.0	The best operators have a relentless focus on leverage, finding ways to multiply their impact
0:04.7	rather than just working harder. But here's what I see happening in finance teams everywhere,
0:09.0	brilliant people getting buried in expense management busy work. If you think about it,
0:12.8	you become a finance leader because you love strategic work, modeling scenarios, optimizing capital
0:17.2	allocation, finding the insights that actually move the business forward. But instead,
0:20.8	you're chasing receipts and categorizing transactions.
0:23.1	It's the opposite of leverage.
0:24.8	This is exactly why I'm so bullish on what the team at Ramp has built.
0:28.5	Kareem and Eric understood that every minute spent on manual expense management is a minute
0:32.4	stolen from high leverage work.
0:34.0	So they automated all of it.
0:35.6	Automatic categorization, receipt matching, spending controls that
0:38.6	actually work. I love the network effect that this creates. When finance teams at companies like Shopify
0:43.7	and Stripe automate the mundane stuff, they free up cycles to think bigger, to ask for your questions,
0:48.5	spot patterns others miss, and make the kind of strategic bets that separate great companies from good
0:53.0	ones. The math is simple. Get your time back, focus on what matters.
0:57.2	Check out ramp.com slash invest and see what happens when you eliminate the busy work.
1:01.4	Cards issued by Sutton Bank, member FDIC, terms and conditions apply.
1:05.7	In asset management, growth often depends on customization.
1:08.6	It's the nature of the beast in our industry, and I know having
1:11.1	experienced the problem firsthand as an active manager, it's a competitive differentiator to tailor
1:15.8	products and services to clients' preferences. Those of us growing our businesses always want to say yes
	...

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