Ep. 39 - Pappy & Jack plus 24 Hours of Daytona: Lanny Hester’s Drive for Purpose

In this second installment of our two-part conversation with renowned story-teller and entrepreneur Lanny Hester, we keep the good times rolling—pouring more Jack Daniels Bonded, savoring a fine Pappy 12-Year, and lighting up a couple of Padrón cigars—the kind of comforts that pair well with big stories.

Lanny dives deeper into his life behind the wheel. He recounts his high-stakes battles on the track: in the 1986 24 Hours of Daytona, he and his team pushed a Roush-built Ford Mustang to a class-leading finish—crossing the line ahead of none other than Bruce Jenner. UPI+1 He also reflects on his time in the 12 Hours of Sebring, where endurance racing brought celebrities, cars, and camaraderie in equal measure. Wikipedia

Lanny opens up about what truly matters to him now: his wife, community, legacy, and the flame of relationships and purpose that burns as steady as any cigar. 

Join us on the porch! 

#EntrepreneurLife #EntrepreneurMindset #Entrepreneurship #LifePurpose#Community #Leadership #Motorsport #RacingLife #EnduranceRacing #Daytona24 #Sebring12 #FordMustang #RaceCar #CarCulture #ClassicCars #AutoRacing #BruceJenner #PaulNewman #Bourbon #Whiskey #PappyVanWinkle #JackDaniels #BourbonLife #WhiskeyGram #BourbonLovers #WhiskeyLovers #KentuckyBourbon #CigarAndBourbon

This week, Jason and Bradford welcome their friend Lanny Hester to the porch — a man whose life story spans industries, eras, and adventures. A talented entrepreneur whose ventures have ranged from the medical world to co-owning Bristol Motor Speedway in the late 1970s, Lanny has lived the kind of life you just can’t script.

With Padron cigars from The Mission Cigar and Social in hand — a brand known for quiet excellence and uncompromising quality — the guys settle into a blind whiskey tasting between Jack Daniel’s Bonded and Pappy Van Winkle 12-Year. Both are fan favorites on the porch, but this afternoon, it’s about pure taste and value — no labels, no bias.

Between sips, Lanny shares stories that sound almost mythical but are entirely true — like the time he found himself in a Las Vegas poker game with Pug Pearson, Amarillo Slim, and Sailor Roberts. And how a bold idea during his time co-owning Bristol led to one of NASCAR’s greatest traditions: the Bristol Night Race.

This episode is more than cigars and bourbon — it’s about creativity, risk, and the kind of vision that turns good ideas into legacies.

Light up a Padron, pour something bold, and join us for an afternoon of unforgettable storytelling with the man who helped bring the lights to Bristol.

#BristolMotorSpeedway #BristolTN #TwoGuysOnAPorch #NASCAR #CaleYarborough #DarrellWaltrip, #AmarilloSlim #PokerLegend #StockCarRacing #Motorsports #NASCARLegends #RacingHistory #Vegas #LasVegas #WorldSeriesOfPoker #WSOP #PokerLegends #PappyVanWinkle #JackDaniels #HighStakesPoker #LegendaryDrivers #StorytellingPodcast #BourbonAndCigars#FranklinTN #FranklinTennessee

Episode 37: The Jack Daniel’s Blind Test – Coy Hill vs. Single Barrel Proof and Kid Launch

On this episode, Jason, Bradford, and Kimber are back on theTennessee porch pouring two powerhouse Tennessee whiskeys for a blind tasting showdown — Jack Daniel’s Coy Hill vs. Total Wine’s Jack Daniel’s Single Barrel Barrel Proof. Both pack a punch north of 130 proof, but can either man tell which is which? The Coy Hill, famously released from the highest floors of the rickhouse where the heat pushes proof and intensity to the edge, faces off against the consistent classic of Single Barrel Barrel Proof. Expect rich oak, dark caramel, and that unmistakable Tennessee charcoal finish — but which one steals the porch crown?

As the smoke from a Liga Privada No. 9 cigar drifts through the fall air, the guys tackle a real-life topic: launching our kids. The Liga Privada No. 9 sets the tone perfectly — a full-bodied cigar known for its dark, oily Connecticut Broadleaf wrapper and complex, earthy character. Notes of espresso, cocoa, leather, and black pepper evolve throughout the smoke, creating the perfect pairing for a high-proof Tennessee pour and a deep conversation.

This week’s discussion hits home: we love having our kids around, but isn’t the goal to raise them so they want to move out and be independent? How do we balance welcoming them home while still encouraging them to build their own lives?

It’s a free-flowing, heartfelt conversation about parenting, independence, and the bittersweet beauty of watching our kids take flight — all while sipping two of Lynchburg’s boldest creations.

#JackDaniels #CoyHill #SingleBarrelSelect #SingleBarrelProof #TennesseeWhiskey #EmptyNest #Fatherhood

Amid the buzz of the iconic Kentucky Bourbon Festival, Jason and Bradford slipped into the shadows of the secret speakeasy at The Trail Hotel in Bardstown, Kentucky. The warm glow of vintage glass and aged oak set the stage for a rare, unfiltered conversation with Jon Robinson — the fearless architect behind the Tennessee Titans’ boldest moves.

Jrob dives deep, sharing candid insights on building a winning Titans roster, making tough calls under intense scrutiny, and navigating life in the NFL spotlight. But the conversation doesn’t stop on the field. He opens up about fatherhood, the daily realities of raising kids with Type 1 diabetes, and the resilience and grit required to balance career, family, and personal growth.

No cigars, no Kimber — just two standout pours: 15 Stars Fine Aged Bourbon and Jackson Purchase Bourbon. 15 Stars opens the tasting with its rich, smooth layers of caramel, vanilla, and warm oak — a bourbon as steady and dependable as a veteran quarterback. Jackson Purchase brings a bold, higher proof edge with hints of warm butter, a whiskey that mirrors the high-stakes decisions and pressure of leading an NFL franchise.

This is bourbon country in its purest form: an evening of rich pours, bold stories, and raw honesty. From savoring 15 Stars and Jackson Purchase to exploring the highs, lows, and unseen challenges of football and fatherhood, this episode is a masterclass in grit, grace, and living intentionally — one sip at a time.

#JonRobinson #TennesseeTitans #NFL #NFLTalk #JRob #TitansFans #NFLPodcast #KentuckyBourbonFestival #15StarsBourbon #JacksonPurchase #BourbonTrail #TheTrailHotel

Ep. 35 - Strong Enough For A Man, But Made By A Woman - KY Bourbon Festival

When Jason and Bradford invite the inimitable Suzanne Phifer Pavitt (of Phifer Pavitt Spirits) their first female guest on the podcast, to join them on the podcast the conversation turns into a masterclass in bourbon, vision, and sensory expertise. Recorded while visiting the speakeasy at The Trail Hotel in Bardstown, Kentucky during the Kentucky Bourbon Festival, this episode, explores how women—perhaps more attuned to aroma and nuance—often lead with their noses in the spirits world, and how that sensitivity becomes an advantage in crafting world-class bourbon.

Suzanne recounts the daring genesis of Late Night, Phifer Pavitt’s 10-year bourbon finished in Napa Valley Cabernet Sauvignon barrels. That extra 13 months in Cabernet-kissed French oak imparts a signature profile of bold vanilla, dark caramel, smoked caramel, almond brittle, and deep raisin and fig notes. She walks Jason and Bradford through the mash bill (80% corn, 11% rye, 9% malted barley) and shares how she leaned into her own sensory intuition to refine the flavors and finish. She also opens up about a catastrophic fire during COVID that destroyed her family farm and winery, and how that experience shaped her resilience and perspective. Sign up for release dates of Late Night and Reserve at www.phiferpavittspirits.com.

Over tasting pours, Suzanne teases out the stories behind each sip: why finishing in wine barrels matters, how tactile memory and scent guide decision-making, and how she balances strength and delicacy in the whiskey she crafts. Jason and Bradford probe, tease, and drink deeply, discovering how a bourbon “made by a woman” can carry enough backbone to impress even the most hardened bourbon purist.

Tune in for laughter, insight, and a sensory journey you won’t forget.

#BourbonLife #BourbonCulture #WomenInBourbon #WhiskeyLovers #KentuckyBourbon #BourbonTasting #WhiskeyWednesday #WomenInWhiskey #bourbon #whiskey #brewzle #Itsbourbonnight #kentuckybourbonfestival #TheTrailHotel

Ep. 34 - Weller 107 Through the Decades + AI Insights | Bourbon Review

Join us on the porch as we taste Weller Antique 107 from multiple eras — a 2002 vintage, a 2000s bottling, and today’s release. Same wheated mash bill, different decades, and subtle differences that every bourbon hunter will love.

We also light up the Perdomo 20th Anniversary Sungrown, aged eight years and finished in bourbon barrel-aged wrappers. Mission Cigar & Social has a personal relationship with Nick Perdomo, making them one of the most exclusive dealers of this iconic Nicaraguan cigar.

While sipping and smoking, we dive into AI and its growing impact — from autocorrect to ChatGPT creating essays, music, and more. Can machines truly capture experience and context? Bradford insists his “Artificial Intelligence” is just his ability to find the good bourbons and cigars first.

If you love bourbon tastings, vintage comparisons, premium cigars, and curious conversations about tech, this episode is for you. Pour a glass, spark a cigar, and join us on the porch!

#Weller107 #BourbonTasting #BourbonCollectors #VintageBourbon #BourbonReview #PerdomoCigar #CigarLovers #AIChat #BourbonHunter #TwoGuysOnAPorch #WhiskeyTasting #BourbonLovers #BourbonPursuit #BourbonWithFriends #BourbonAndBS #BourbonJunkies #ItsBourbonNight #TheMashAndDrum #ADHDWhiskey #WhiskeyTribe #WhiskeyVault #BourbonPodcast #BourbonShowdownPodcast #ThisIsMyBourbonPodcast #BourbonAndBadges

Jason and Bradford take a spirited trip to the Kentucky Bourbon Festival, staying at the iconic The Trail Hotel in Bardstown. Along the way, they dive into tastings of incredible bourbons including A. H. Hirsch, Peerless, Jackson Purchase, Rabbit Hole, Luxe Row, Yellowstone, Whiskey House, Limestone Branch, Castle & Key, Jimmy Russell’s Masters Keep, Parker’s Heritage, JW Gant Bottled in 1941, Chicken Cock Whiskey, and Augusta.

They meet bourbon icons like Craig Beam of Jackson’s Purchase, Ashley Barnes, Master Blender for EJ Curley and Lucky Seven, Myra Barginear of Paul Sutton Bourbon, and Suzanne Phifer Pavitt of Phifer Pavitt Winery and Spirits, who is releasing an inaugural bourbon within the next year called Late Night, sharing stories, insights, and a few laughs along the way. Alongside tasting these incredible pours, they also make purchases for future episodes. From rare bottles to festival highlights, this episode captures the best of Bourbon Country and the adventures that only happen when two friends sit down with great bourbon in hand.

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In this episode, Jason and Bradford crack open three of the most coveted bourbons in the world—Pappy Van Winkle 15, 20, and 23 Year—and go completely blind in a head-to-head tasting showdown.

👉 Will the guys pick the right bottles?

Each iconic expression brings its own personality to the porch:

To raise the stakes, the guys light up a Partagas 160, a rare celebratory cigar wrapped in aged Cameroon leaf, letting the smoke mingle with the bourbons’ rich layers.

But it’s not just whiskey and cigars on the porch—the conversation drifts into a different kind of “aged” subject: the 24-hour news cycle. What happened to the days when news came twice a day—once in the morning and once at night—and life filled the space between? Has the endless flood of alerts reshaped how we see the world, our neighbors, and even ourselves? From the rise of CNN to smartphones, from 9/11 to today’s polarized feeds, Jason and Bradford dig into nostalgia, critique, and some tough questions about what we’ve lost in the noise.

#PappyVanWinkle #BourbonTasting #Pappy15 #Pappy20 #Pappy23 #RareBourbon #WhiskeyReview #BourbonReview #BlindBourbonTasting #WhiskeyTube #BourbonTube #BourbonCommunity #BourbonHunters #WhiskeyLife #CigarAndWhiskey #Partagas160 #TwoGuysOnAPorch #BourbonPodcast #WhiskeyTalk #PappyHunt #PorchTalk #BourbonCulture

Ep. 31: Rare Pours & Purpose: Old Fitzgerald, Pappy Van Winkle, & Weller Millennium

In this special episode of Two Guys On A Porch, Jason and Bradford go deep — into both rare pours and real purpose. They’re lighting up a Rocky Patel Vintage 1990 cigar and diving into three exceptional whiskeys that represent the pinnacle of craftsmanship, history, and collector intrigue:

Pappy Van Winkle 23 Year – The icon. A wheated bourbon with unmatched legacy and mystique. Aged 23 years and bottled at 95.6 proof, this pour is velvet on the palate and heavy with lore. It’s the kind of whiskey that deserves reverence — and good conversation.

Old Fitzgerald 19 Year Bottled in Bond – A beautiful nod to history and heritage, this wheated bourbon from Heaven Hill pays tribute to Pappy Van Winkle himself, who once distilled Old Fitz. With a mash bill of 75% corn, 20% wheat, and 5% malted barley, it’s a bold, elegant reminder that BIB bourbons still punch way above their weight. Aged nearly two decades, it delivers depth, maturity, and that signature Heaven Hill sweetness.

Weller Millennium – The rarest and most ambitious pour of the lineup. Released in 2024 to commemorate the new millennium and Buffalo Trace’s ownership of the Weller name, this whiskey is not technically a bourbon — because it’s at least 51% wheat. Made from distillations across 2000, 2003, 2005, and 2006, aged between 18 and 24 years, bottled at 99 proof, and presented in an amazing lit package, & handcrafted crystal decanter. 

As the guys explore these epic pours, they ask a bigger question: Why are we doing this podcast? A year in, what started as two friends talking cigars and bourbon has become something deeper — a space for presence, purpose, and honest connection. Is it a mission? A tradition? A lifeline for men craving real conversation?

Whether you're a bourbon collector, a cigar enthusiast, or just someone looking for meaning behind the smoke and the sip — this episode is a reminder that the porch is more than a place. It’s a mindset.

#PappyVanWinkle #OldFitzgerald #WellerMillennium #BourbonLife #WheatedBourbon #RareWhiskey #BourbonEnthusiast #BuffaloTrace #HeavenHill #WhiskeyLovers

Jason and Bradford are back on the porch chasing bourbon dreams—and this time, they’re chasing unicorns. The guys dive into a blind taste test of some of the most elusive bottles in the Buffalo Trace lineup, putting price, palate, and prestige to the test.  Can they identify the pairs correctly?

They pair Weller Antique 107 vs. Pappy 15 Year, and Weller 12 Year vs. Pappy 12 Year Lot B—all in a blind lineup to see if legendary names live up to the hype. Can a $150 bottle hang with one that fetches $3,000? And does that “Poor Man’s Pappy” recipe really stand a chance against the real thing?

But this episode isn’t just about bourbon—it’s about perspective. “If my 25-year-old self knew what I know now, what would I do with the information?” At 25, Bradford was married and five years from becoming a dad. Would having a “cheat code” for life have changed anything? It’s a twist on the old journey vs. destination question: if you’re happy with where you are now, would you really rewrite the past?

As they sip through their dream lineup, they light up the Padron 50th Anniversary, a cigar worthy of the moment—bold, refined, and a reminder that some things, like wisdom and whiskey, take time.

Pour something special, settle into your favorite seat, and reflect on life, legacy, and what really matters.

#TwoGuysOnAPorch #DreamTasting #BourbonWisdom #PappyVsWeller #BlindTasting #Padron50th #PoorMansPappy #BuffaloTrace #LifeCheatCode #JourneyVsDestination #WhiskeyTalk #CigarAndBourbon #PorchPhilosophy #WhiskeyReflections