Ep. 462 - The Lifestyle Investor COO, Ryan Casey

Second in Command: The Chief Behind the Chief

Second in Command with Cameron Herold

Entrepreneurship, Business, Management, Careers

4.5 • 1.6K Ratings

🗓️ 1 April 2025

⏱️ 44 minutes

🔗️ Recording | iTunes | RSS

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Summary

In today's episode of The Second in Command podcast, Cameron is joined by Ryan Casey, Chief Operating Officer for The Lifestyle Investor.

Ryan shares insights from an unexpected career journey that began in a surprising industry and led to expertise in sales, systems, and personal development. The conversation explores the power of structured approaches to relationship-building, professional growth, and leadership, highlighting how early experiences shaped a mindset focused on efficiency and strategic thinking.

You'll learn about Ryan's pivotal career transitions, from managing multiple businesses to stepping into a leadership role within a rapidly growing organization. The conversation explores the challenges of scaling a founder-driven company, striking a balance between maintaining core values and building systems that allow for sustainable expansion.

Whether you're an entrepreneur, a sales professional, or someone looking to optimize your approach to success, this episode is packed with thought-provoking lessons and actionable strategies.

If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!

Enjoy!

In This Episode You'll Learn:

Ryan's experience with Orangetheory, including the challenges of marketing and generating leads during the COVID-19 pandemic.
The benefits of having a founder-led company and the challenges of transitioning from a passion project to a business.
The various asset classes the Lifestyle Investor covers, including private equity, credit funds, real estate, etc.
Ryan's approach to marketing and learning, including joining coaching programs and masterminds to stay ahead of industry trends.
And much more...

Resources:

Connect with Ryan: Website | LinkedIn

Conversation with Griff Long, COO, Orangetheory Fitness

Connect with Cameron: Website | LinkedIn

Get Cameron’s latest book – "Second in Command: Unleash the Power of Your COO"

Get Cameron’s online course – Invest In Your Leaders

Transcript

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0:00.0	Hey, it's Cameron Harold, the host of the Second Command podcast. Before we dive in, there's something you need to know.
0:05.5	If you're a C-O-O-V-P operations or you're in any role where you're the second-in-command to the CEO,
0:12.1	the C-O Alliance is the place for you. If you're the integrator to the visionary, you're going to want to join us.
0:18.4	The C-O Alliance is the world's leading community for the second command.
0:22.4	We've had over 500 members like you join from 17 countries to grow their skills,
0:27.6	connections, and confidence.
0:29.1	You'll get the tools, friendships, and a 10x guarantee to ensure that you get your
0:33.6	money's worth.
0:34.6	Go to COOalliance.com to learn more and see if you qualify. You can even
0:39.4	book a free call with our team to ask questions. Now let's jump into this week's episode.
0:44.0	I think two things that really I learned with Cutco is I was a shy kid. So much to the point that
0:49.8	when I came home and told my dad that, hey, I'm going to go sell knives. Still to this day, now I was
0:56.2	17 when that happened. To this day, I've never seen him laugh so hard. Like on the floor
1:01.2	laughing that this shy kid was going to go in people's houses and sell knives. But so playing
1:06.8	off that, the two things I really learned was one was the personal growth. That was the first time
1:10.4	where they really encouraged it. And I saw how there was a direct correlation with the more I grew,
1:16.0	the more I made, the more I advanced. And that was motivating to me. And so that really got me
1:21.0	down that personal growth track.
1:35.5	Welcome to the Second and Command podcast, produced by the C.O. Alliance and brought to you by its founder, Cameron Harold. In the Second in Command podcast, we talk to top COOs who share the insights, strategies, and tactics that made them the chief behind the chief. And now, here's your
1:46.5	host, Cameron Harold. All right. We get a great episode right now. This is actually the CEO of a
1:55.7	friend of mine, Justin Donald, from Lifestyle Investor. Our guest today is his C-O-O Ryan Casey. Ryan's a really solid
2:02.9	entrepreneur and a sales expert with a background in leadership and business growth. After earning
	...

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