The Gentlemanly Things Podcast

In the second half of this two-part conversation, Brian and performance coach Juan Bendana move beyond confidence and into the deeper question of identity.

Last time we explored confidence as a muscle built through action…this episode examines what happens after momentum begins: how habits, discipline, and even appearance reinforce our identity.

Juan explains why progress (not achievement) is the true driver of happiness, why compari...

In the first of this two-part conversation, Brian welcomes speaker and performance coach Juan Bendana to examine what confidence truly is (and why so many people misunderstand it).

Rather than a fixed trait or personality advantage, Juan reframes confidence as a muscle: something built through discipline, discomfort, and consistent practice. No matter where you are—or how far off track you feel—reinvention is always possible.

With the holidays in full swing, Brian reflects on the season, what gratitude looks like in practice, and why the most memorable gifts aren’t always the most expensive. 

He also considers how a gentleman can express care with nuance, whether through something crafted, curated, or experienced.

Along the way, he shares personal reflections from the Thanksgiving table, insights from inside Henry A. Davidsen, and a perspective on giving ...

With Thanksgiving right around the corner, Brian Lipstein returns to the world of wine–this time with practical advice for anyone wondering what to pour, serve, or bring to Thanksgiving dinner.

From understanding acidity, body, and tannin to knowing the difference between bottle shapes and glassware, this episode makes wine basics approachable. You’ll discover the best wine to pair with turkey, stuffing, and all the classic Than...

Grooming. It’s not just about how you look. It’s about how you feel.

Most of the men we admire for their confidence and presence put these practices into play on a regular basis. Not for vanity, but for the quiet power that comes from showing up well-prepared for life.

In this episode, Brian Lipstein explores five essential grooming habits that elevate not only your appearance, but how others perceive and respond to you. From...

What does it really mean to dress like a gentleman?

In this episode, Brian Lipstein dives into the deeper psychology of style, exploring how clothing is not just a form of self-expression, but a catalyst for confidence, connection, and even desire. 

Inspired by a series of quotes collected over years in the menswear world, Brian unpacks the relationship between image, attraction, and performance—both professional and personal...

Watch Part One of the conversation with Bruce Phillips here:

https://www.youtube.com/watch?v=F9eq0vs5iFY

In this continuation of our conversation with Bruce Phillips of Vine Hill Ranch, we turn our focus to the artistry, science, and philosophy that define fine wine–and what elevates it to a truly gentlemanly pursuit.

Bruce shares the powerful story of Vine Hill Ranch's leap from premium grape grower to world-class produ...

Pour a glass of your favorite red and join us for a journey through Napa Valley’s past, present, and future with Bruce Phillips of Vine Hill Ranch.

In this episode, Bruce—third-generation steward of one of Napa’s most revered vineyard sites—invites us into the quiet, powerful story of how Vine Hill Ranch helped shape the renaissance of American wine. From the aftermath of Prohibition to the phylloxera crisis and the vineyard’s b...

Today Brian Lipstein unpacks one of the most misunderstood aspects of menswear: the true difference between off-the-rack, made-to-measure, and custom or “bespoke” suits. 

With the fall wardrobe season in full swing, he begins by recapping Henry A. Davidsen's recent trunk show—now reimagined as the Fall Wardrobe Event—and shares why that evolution in language matters just as much as the garments themselves.

From the historical roo...

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...

In today’s episode, Brian confronts one of the most misunderstood topics in menswear: the difference between style and fashion.

Drawing from years of experience as an image consultant and master tailor, Brian explains why chasing fashion trends can become an expensive and confusing hobby—one that often compromises authenticity and first impressions. He introduces style as a more intentional, enduring, and personality-driven approach...

Join Brian Lipstein in delving into one of the most overlooked elements of a gentleman’s lifestyle—the intentional cultivation of relationships.

Brian’s experience reveals a timeless truth: it’s not just effort that builds success, but the quality and depth of one’s network. From concerts in Philadelphia to business breakthroughs, you’ll hear how seemingly small “give, help, feed” gestures compound over time into lasting influence.

T...

In this second half of Brian’s in-depth conversation with Alex Weghorn of Davidoff Cigars, we journey further into the thoughtful world of cigar craftsmanship and the deeper meaning behind a gentleman’s rituals.

Alex demystifies the aging process of cigars, explains how environmental factors shape tobacco character, and draws compelling parallels between wine, tailoring, and cigar rolling. But this episode isn’t just about cigars—it...

In this richly layered part-one episode of The Gentlemanly Things, Brian welcomes Alex Weghorn, U.S. Ambassador for Davidoff Cigars, for a deep dive into the timeless craft of premium cigars and their place in the modern gentleman’s lifestyle.

Alex shares the century-long legacy of Davidoff—from its founding by Zino Davidoff to its transformation into a global symbol of consistency, quality, and refinement. Together, they explore ho...

In this spirited solocast, Brian Lipstein steps away from menswear to explore another hallmark of refined living: Scotch whiskey.

Join him for a live tasting of four remarkable expressions—Dalwhinnie 15, Glenlivet 12, Glenlivet 18, and Lagavulin 16—as he walks through tasting techniques, whiskey history, and the nuances of regional character.

You’ll learn how to properly awaken your palate, the difference between single malt and blen...

In this episode of The Gentlemanly Things, Brian welcomes Luke Mayes, North American representative for the legendary House of Dormeuil, to explore what truly makes a fabric—and a life—luxurious.

Luke’s journey spans the Royal New Zealand Air Force, decades in the fine cloth trade, martial arts mastery, and world travel. Together, he and Brian dive deep into the technical artistry behind Dormeuil’s fabrics—from top dyeing and two-pl...

In this foundational episode of The Gentlemanly Things, host Brian Lipstein takes us behind the scenes of Henry A. Davidsen to reveal the core values that drive both his business philosophy and personal approach to gentlemanly living.

Brian shares the deliberate process of developing values that serve as true north—a compass for making decisions when stakes are high and choices matter most. From the unexpected opportunity that COVID...

In this episode of The Gentlemanly Things, host Brian Lipstein explores the deeper psychology of personal brand and image consulting—going well beyond style tips to uncover why the way we present ourselves shapes not only how others perceive us, but how we see ourselves.

You’ll learn the surprising truth about how often we see our own reflection each day, and how each glance subtly reinforces our mindset. Brian breaks down the f...

Welcome to The Gentlemanly Things. In this premiere solocast, host Brian Lipstein invites us into the world that inspired the show–a place where image, intention, and elegant living intersect.

We journey through Brian’s personal story: from a college student indifferent to suits to a master tailor and certified image consultant. Along the way, we uncover how style, upbringing, and identity are deeply intertwined–and why understa...