EPISODE 10

The Keystone of Gentlemanly Living: How Awareness and Intention Lead to Success

Today Brian Lipstein steps back from the outward trappings of refined living to explore the inner journey that makes them possible. It's not just about wine, whiskey, or bespoke suits—it's about the intentional choices that allow us to access and truly appreciate them.

Drawing inspiration from a recent Entrepreneurs’ Organization conference, Brian shares personal stories—ranging from health challenges to spiritual philosophy—that illuminate a deeper principle: being a gentleman is a matter of choice. He discusses the critical importance of physical, mental, and spiritual health as the keystone of a fulfilling, gentlemanly life.

We hear about the origin of a green jacket (with a name you might recognize) and how its symbolism ties into a lifestyle of aspiration and intention.

Whether it’s through health, mindset, or energy, this episode challenges listeners to consider not just what they pursue—but how and why they pursue it.

0:00 Intro

2:17 The theme of Intentionality

4:12 “Being a gentleman is a matter of choice”

5:10 The story behind the green jacket

7:48 Reflections from the EO conference

10:30 Reflections from acupuncture

12:11 The triangle of heath

17:28 The mental load of entrepreneurship

20:49 Spirituality, karma, and energy

23:31 Awareness and choice

26:01 Preview of what’s to come

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