Season One of The Gentlemanly Things is officially in the books, and Brian Lipstein is taking a moment to look back on the first 20 episodes. 

In this recap, Brian revisits some favorite conversations and shares what he learned from launching the show and evolving in real time.

A few themes kept showing up along the way: progress matters more than perfection, alignment beats empty goals, and intention changes how we live and work. 

Stay tuned for the next chapter, bringing even more great guests. Thanks for being part of the journey!

0:00 Intro

0:38 Season 1 Recap

4:56 Listener Feedback & Personal Growth

5:24 Celebrating Milestones

7:17 Season Two Preview

12:06 Final Reflections

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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 comparison quietly erodes growth, and how small daily actions compound into lasting transformation.

If Part One was about getting started, this episode is about staying aligned, long after the initial motivation fades.

-Catch Part One if you haven’t yet: https://youtu.be/V4ziLH53CGY

0:00 Intro

2:03 Why habits fail when identity lags behind action

7:41 Discipline, routines, and becoming who you say you are

14:56 Progress as the real source of happiness

22:18 The danger of comparison and distorted benchmarks

30:42 Why presentation reinforces personal standards

37:10 Turning goals into identity-based commitments

Connect with Juan:

https://www.juanbendana.com/

https://www.instagram.com/juanbendana/

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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.

Juan shares his own rock-bottom moment and how that experience shaped his work with business leaders to top-tier performers, helping them establish daily rituals that align action with identity.

If you’ve ever felt caught between who you’ve been and who you know you’re capable of becoming, this episode offers both the perspective and the resolve to take the next step.

-This is Part One of a two-part conversation. Part Two continues next week.-

0:00 Intro

0:48 Meet Juan Bendana

3:37 Confidence as a muscle

8:50 The 10X mindset

13:07 Balancing leadership, vision, and service

17:27 The art of stepping away to elevate your team

23:42 From self-doubt to transformational change

27:34 Why discipline is discomfort practiced

29:00 Preview of Part Two

Connect with Juan:https://www.juanbendana.com/ 

https://www.instagram.com/juanbendana/ 

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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 that’s as much about identity as it is generosity.

This episode invites listeners into a thoughtful exploration of holiday gifting. Not the transactional kind, but the kind that conveys intention, attention, and genuine appreciation.

0:00 Intro

1:20 The mindset of the season

4:36 Family, health, and the people who shape us

6:48 Looking ahead at Henry A. Davidsen’s evolution

9:29 Quieting the noise of the holiday rush

10:18 The man who “has everything”

12:07 What your gift says about you

15:18 Gifts that create lasting impressions

20:36 Love languages

24:16 The Gift of Fit

Gift of Fit holiday packages:https://henrydavidsen.com/2025-holiday-packages/ 

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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 Thanksgiving sides.

Whether you're hosting the big meal or bringing a bottle to share, this episode will help you choose a wine that complements the menu…and impresses your fellow guests.

0:00 Intro

1:04 Wine and Thanksgiving

3:56 The basics of understanding a wine label

5:22 What glassware and bottle shapes actually tell you

9:06 The 3 key traits to look for in any wine

13:07 How to choose a wine that enhances your meal

17:55 A crowd-pleasing red for Thanksgiving dinner

19:51 A white wine option that works surprisingly well

21:42 Final thoughts and serving tips

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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 head to toe, these small refinements can have a lasting impact.

Whether you're refining your current routine or building one from scratch, this episode is a reminder that grooming is self-respect, expressed with intention.

0:00 Intro

1:04 Why grooming matters

2:02 Grooming Tip #1: Haircuts

8:52 Grooming Tip #2: Shaving

21:16 Grooming Tip #3: Manicures and pedicures

24:38 Grooming Tip #4: Shoe shines

28:58 Grooming Tip #5: Cleanliness

33:38 Grooming as intentional living

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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.

From the subtle art of aligning your wardrobe with your personality, to the often-overlooked power of a smile, this episode offers both reflection and real-world insight. You’ll also hear stories from the Henry A. Davidsen showroom that reveal just how transformative dressing well can be—not just for how others see you, but how you see yourself.

If you've ever wondered why women swoon for a man in a well-tailored suit, or how confidence can elevate every room you walk into, this one’s for you.

0:00 Intro

1:08 Jacket story: “Wild and Free”

4:21 The power of quotes and what they reveal about values

5:19 “A well-dressed man to a woman is like lingerie to a man”

9:08 Sales training, personal brand, and the “Sex and Money Show”

11:22 Style, attraction, and reigniting relationships

12:22 Confidence > Good looks

13:45 How we read authenticity in dress

14:43 Using lifestyle cues to inform personal style

16:37 A smile looks good on everyone

18:01 “What are you leaking?”

19:53 Confidence as a learned, embodied trait

20:23 “The better you dress, the worse you can behave”

23:46 Dressing well as a sign of respect

24:40 Being a true gentleman never goes out of fashion

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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 producer, unpacking the decisions, risks, and values that shaped their iconic VHR Cabernet Sauvignon. From the influence of legendary winemakers like Bob Levy and Francoise Peschon to navigating wildfire smoke and climate volatility, Bruce walks us through what it takes to make wine that transcends taste and becomes time itself in a bottle.

Brian and Bruce also explore the parallels between tailoring and winemaking–two crafts that blend technical mastery with artistic intention–and consider what makes wine a luxury worth savoring. For those who appreciate rarity, legacy, and intentional living, this episode offers an unforgettable vintage of insight.

Whether you're a seasoned collector or newly curious, pour yourself something special and enjoy a masterclass in refinement, humility, and heritage.

0:00 Intro

1:12 The vision behind Vine Hill Ranch’s first label

6:56 From vineyard designation to VHR Cabernet Sauvignon

11:04 Why winemaker consistency matters

13:52 The myth of “overnight success”

18:16 Surviving the 2022 heatwave

24:57 Understanding site expression in Napa wine

30:06 Vintage variability and the story each bottle tells

35:26 Tasting Napa’s elevation through fruit character

39:19 When wine becomes a gentlemanly thing

43:11 Parallels between fine wine and custom tailoring

47:53 A market correction–and what it means for quality

55:10 Looking ahead: future vintages and hope for the industry

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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 bold redevelopment, Bruce shares what it takes to cultivate excellence across generations.

Together with Brian Lipstein, they explore how Napa’s mindset has evolved from Bordeaux-inspired blends to a Burgundian focus on micro-site expression—one that places terroir, family legacy, and intention at the heart of winemaking.

Whether you're a connoisseur, a collector, or simply someone who values stories rooted in heritage and vision, this episode offers a rich pour of insight into what makes Napa—and the people behind it—truly extraordinary.

0:00 Intro

1:03 Meet Bruce Phillips, third-generation Napa Valley grape grower

5:00 What Napa looked like in the 1950s

9:50 Surviving Prohibition and reclaiming quality

14:30 Bruce’s father and the vineyard’s pivotal redevelopment

20:00 Rebuilding Napa through phylloxera and vision

26:45 The terroir of Vine Hill Ranch: geology, climate, and complexity

34:20 Napa’s shift from Bordeaux to Burgundian mindset

39:45 Kinsman Eades, MacDonald, Detert, and the next generation of Napa producers

41:43 Closing remarks and preview of Part Two

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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 roots of the term “trunk show” to the visual metaphor that separates made-to-measure from bespoke, Brian offers an education in elegance. This episode serves not only as a guide to terminology but as a deeper exploration into why craftsmanship, intention, and precision distinguish the gentleman’s wardrobe from ordinary dress.

Whether you're considering your first custom suit or refining an already sophisticated wardrobe, this episode provides the language—and the lens—to make more informed, cultivated decisions.

0:00 Intro

1:30 Fall Wardrobe Event recap and EO learning with Juan Bendana

4:21 What’s exciting Brian this season

7:14 The origin and evolution of trunk shows

9:08 Defining off-the-rack vs made-to-measure

13:22 What made-to-measure really means

16:15 The “computer image” analogy for fit adjustments

18:10 Entering the world of custom and bespoke

20:34 Handwork and the art of moldability

22:53 Time and technique: why bench-made matters

25:19 The origin of “bespoke” explained

27:43 Savile Row and the true art of tailoring

30:06 Elevating your wardrobe with knowledge and intention

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