Jon Muedder is the Founder, President and Executive Producer of Caravan, a creative production studio based in the Southeast U.S. In this conversation, Greg & Jon discuss:- Jon’s experience building a business “starting from the closet”- How the EOS system helped Jon organize his business for sustainable growth- How obsession and craft separate A players from B players- Books that have influenced Jon as a leader- The impact on Jon and his family from navigating his son Finn’s diagnosis with a terminal genetic disease called Hunter Syndrome- Health & wellness practices that help Jon maintain balanceFull timestamps here:01:17 – Building a high-end content studio05:47 – When outward success didn’t equal happiness06:55 – Finding and implementing EOS10:34 – Corporate values that actually matter 15:00 – Craft, obsession and differentiating A and B players22:07 – Resources and practices that have made Jon a better leader29:50 – The fallacy of work/life balance33:13 – Finn’s story 47:25 – Health & wellness practices Jon follows to find balance53:51 – One thing Jon has figured out in life Links / resources mentioned in the conversation:Organizations:Caravanhttps://www.wearecaravan.tv/https://www.instagram.com/madebycaravanhttps://www.linkedin.com/company/madebycaravan/Project Alivehttps://projectalive.org/‘Finn': Our Storyhttps://projectalive.org/stories/finnBooks:Traction by Gino WickmanEOS Life by Gino WickmanStrength to Strength by Arthur BrooksWorking Genius Assessment by the Table Group5 Types of Wealth (Not Mentioned but Jon loves this book) by Sahil BloomMake sure to subscribe to Greg's weekly Intentional Wisdom newsletter at gregcampion.substack.com

In this episode, I sit down with Andy Rafal, CEO of OLI—a 50+ year-old chemical engineering software company operating at the intersection of AI and the physical world.

Andy and I have known each other for over 20 years, going back to our early days in New York City. This conversation covers his journey from hedge fund investing at Tiger to becoming an operator and CEO—and the lessons learned along the way.

We talk about career transitions, decision-making under uncertainty, and what it really means to build something over the long term.

We also dig into how AI is reshaping industries—especially those rooted in the physical world—and why the biggest opportunities may lie in bridging the gap between software and real-world systems.

Episode Timestamps

00:00 - Intro + what we cover

02:20 - Andy’s early career path: Cornell, law school, and following curiosity

07:15 - Why he turned down law for Tiger

22:43 - Lessons from Tiger: wins, losses, and what actually matters

28:06 - Why curiosity and lifelong learning are career superpowers

30:22 - The transition from investor → operator — and the difference between analyzing a business vs. building one

37:58 - How COVID reshaped leadership, culture, and strategy

38:26 - Building teams, culture, and long-term thinking

41:01 - Taking over a 50+ year-old company founded by his father

41:31 - The challenge of modernizing a legacy business

44:23 - How AI is impacting engineering, chemistry, and real-world systems

48:29 - The risk of AI “getting things wrong with confidence”

49:46 - Writing publicly, learning in public, and finding a voice as a CEO

Key Takeaways

• Career paths are rarely linear—following curiosity often leads to better outcomes than rigid planning
• Investing teaches you how businesses work—but operating teaches you how hard it is to build oneNot every decision needs to be perfect—but you need to update your thinking as new information comes in
• The biggest opportunities often sit at the intersection of old systems + new technology
• AI will transform industries—but human judgment and real-world context still matter deeply
• Taking time to think (and not rushing into the next thing) can be one of the most valuable decisions you make

Connect with Andy on LinkedIn: https://www.linkedin.com/in/andy-rafal/

Follow Andy on Substack: https://arafal.substack.com/

If you enjoy conversations like this, I write a weekly newsletter called Intentional Wisdom where I share:

• Notes on health, performance, and longevity
• Career insights and lessons from conversations like this
• Tools and ideas I’m experimenting with

You can subscribe here: https://gregcampion.substack.com/

Author Jon Finkel returns to Intentional Wisdom to talk all things middle age—health, family, career, and why doing hard things still matters. Jon shares how he's stayed strong (literally) through his 40s by building non-negotiable habits around fitness, taking up competitive swimming, and doing the work that lights him up. We also talk about the importance of being present as a dad, planning epic vacations, and why training for something—anything—is the ultimate midlife unlock.

This is a conversation for anyone who wants to keep showing up with intention as the years stack up.

Episode Segments[00:00:00] Intro to Intentional Wisdom & Jon Finkel.

[00:00:49] Jon Finkel: "World's Most Sophisticated Meathead."

[00:01:09] Tackling middle age: health, fitness, relationships, career.

[00:06:00] Friends' fitness/career struggles.

[00:07:29] Jon's secret: consistency.

[00:08:10] Health as life's foundation.

[00:11:29] "Bench o'clock Monday" at "Flex Factory."

[00:11:55] Train for specific goals.

[00:12:28] Jon back to competitive swimming.

[00:16:23] Mobility wake-up call

[00:17:49] "Knees Over Toes" program.

[00:20:06] From stiff to dunking again.

[00:39:50] Tailoring parenting to each child.

[00:59:45] "Midlife Male"

[01:01:00] Jon's newsletter strategy.

[01:13:00] Check out Jon's "Books and Biceps."

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• You can learn more about Jon's work by visiting jonfinkel.com or by following him on Twitter @Jon_Finkel or Instagram @Jon_Finkel.

  Don't forget to follow Greg on Twitter @gregorycampion and subscribe to his bi-weekly newsletter: https://gregcampion.substack.com/

  If you enjoyed this episode, please consider rating and reviewing Intentional Wisdom wherever you get your podcasts.

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