A Second Wind In Life: Lessons From A Billionaire Mentor With Darren Eads The Purpose Matrix podcast

A Second Wind in Life: Lessons from a Billionaire Mentor with Darren Eads

5d ago 41:50

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What if a single relationship could change the trajectory of your life?

In this deeply inspiring episode of The Purpose Matrix, Phil sits down with Darren Eads—a former private chef turned mission-driven entrepreneur. Darren’s transformation didn’t begin with a business plan. It started with a relationship: working for billionaire Clay Mathile, former owner of IAMS and founder of Aileron.

Clay didn’t just offer Darren a job—he offered a new way of seeing the world. And it changed everything.

Today, Darren runs Second Sail Holding Company, a people-first business acquisition firm that helps legacy owners transition their companies into the hands of leaders who care.

Darren shares how proximity to greatness shifted his mindset, why 53 was the perfect time to start, and how his kids now get to watch him live life with intentionality.

Here’s what you’ll learn:

How proximity to great people can change your life
Why it’s never too late to start living with purpose
The power of foundational habits and aligned circles
Why Darren buys businesses differently
How to lead a team by getting out of the weeds
The myth of needing it all figured out before you begin

Whether you're just starting your journey or pivoting later in life, this conversation is a masterclass in late-stage reinvention, value-driven business, and why mentorship still matters.

0:00 Intro

0:56 Darren’s Background and Early Career

4:42 Meeting a Billionaire Who Shifted His Mindset

10:28 What Clay Mathile Taught Him About Leadership

14:45 Foundational Habits and Getting in the Right Circles

18:02 Family, Regret, and Rewriting the Narrative

24:28 What “Second Sail” Really Means

29:08 Buying a Business the Right Way

33:51 The 30-Year-Old vs. 50-Year-Old Path to Ownership

36:15 Darren’s Leadership Shift

40:12 Living With Gratitude and Alignment

Resources Mentioned:

📚 Rich Dad Poor Dad by Robert Kiyosaki

📚 Buy Then Build by Walker Deibel

🎧 Acquiring Minds Podcast

🌐 Aileron: https://www.aileron.org/

Connect with Darren:

🌐 Second Sail Holding Co: https://secondsailcapital.com/

🌐 Jarvis Mechanical: https://www.jarvismechanicalco.com/

🔗 Darren Eads on LinkedIn: https://www.linkedin.com/in/darren-eads-0a501868

Follow Phil on Social @PhilOnPurpose

https://www.instagram.com/philonpurpose

https://www.facebook.com/philonpupose

100 episodes