Due Time presents: The Watchers

What does a $10 million Popeyes empire, a bottle of 2009 Burgess, and a two-tone Datejust from your father have in common? They all tell the story of Ron Jordan.In this episode of The Watchers, Rod Dye and Rio The Watcher sit down with entrepreneur, medical device sales rep, wine sommelier, and watch collector Ron Jordan for a deeply personal conversation about legacy, failure, and what watches really represent when the flex isn't the point.Ron traces his path from growing up in his family's Popeyes franchise to scaling six locations, pivoting into experiential dining, and ultimately returning to his first love in sales. Along the way, he shares how his father's gifted Datejust ignited a lifelong Rolex obsession, why AP is the most overrated brand in his book, and how a yacht show in Fort Lauderdale taught him that real money doesn't dress up.Things You’ll LearnWhy Ron believes failure is the single most important ingredient in any success story, and how to use it intentionally.How a family-owned Popeyes franchise scaled from one unit to six and $10.7 million in revenue through strategic acquisitions.Why the Rolex Day-Date remains the cultural and historical cornerstone of the brand, from Wall Street to Tony Soprano to hip-hop.Tools / Frameworks Matt SharesSpeed of Execution Advantage: Moving ten times faster than competitors means reaching the idea stage, executing, solving problems, and iterating before others finish discovery.The Wine Parallel: Finding 90–95 point bottles at $25–50 is the same skill as identifying watch value.Practical Over Frugal: Every purchase should pass the exit test. If you can't get out of a watch at a reasonable value, the buy doesn't make sense, regardless of how beautiful it is.Fail Forward Framework: Expect failure, study it, let it define your character, and use the pattern recognition it builds to navigate the next obstacle faster. Key Timestamps(0:00) – Intro and wrist check(4:05) – Ron gifts the hosts a 2009 Burgess wine and explains its connection to watch collecting(7:50) – First-gen experiences, wine journey, and experiential dining(10:55) – Ron's career journey: sales, Popeyes franchise, scaling to $10.7M(17:39) – Ron's father, the gifted Datejust, and falling in love with Rolex(23:08) – The Christmas cabinet story: how Ron received his first Rolex(25:23) – The Batman purchase on Ocean Drive in Miami(27:09) – Tag Heuer as the gateway watch and the 2015 era of luxury entry(30:25) – Full collection breakdown: Chopard, Panerai, AP, and beyond(32:57) – The Fort Lauderdale yacht show story and what real money looks like(36:20) – Ron's next watch: the Tiffany blue Land-Dweller(38:17) – Rapid fire: favorite brand, most overrated brand (AP), dream pieces(44:30) – Rod's watch journey: from Breitling to Rolex, the SKO moment, and building a collection(52:00) – Why the Day-Date is the quintessential Rolex and its cultural significance(57:00) – Final message: why you need to expect failure and embrace it#rolex #watchcollecting #luxurywatches #daydate #datejust #watchculture #watchcommunity #entrepreneurship #failure #mindset #failforward #firstgenerationwealth #familylegacy #legacy #presidentialrolex #batmangmt #APoverrated #sommelier #finedining #thewatchers

What happens when a first-generation tech executive from Detroit brings the same hustle that built his career into the watch world?In this episode, Karlos Williams of 10and2media joins Rod Dye and Rio the Watcher to break down everything from Rolex purchase history strategy to why authenticity beats access every time. Karlos shares his journey as a Detroit-raised, first-generation everything and unpacks how his Pikachu Daytona, Pepsi GMT, and Detroit-inflected style all tie back to one core idea: take up space as your real self.Along the way, the trio dig into AD relationships, the looming Pepsi GMT discontinuation, why precious metal is making a comeback, and how AI fluency is becoming non-negotiable for the next generation of collectors and professionals.Things You’ll LearnWhy building a real, personal AD relationship beats spreading purchase history across multiple dealers.How Detroit culture shapes a distinct collecting style, from Cartier buffs to two-tone Daytonas.Why AI fluency is becoming as important as your degree, and how to position yourself early.Tools / Frameworks Matt SharesSpend Consolidation Strategy: Why funneling purchase history to one or two ADs unlocks allocation faster than spreading it thin.The Lighthouse Principle: Show up authentically in every room because someone younger is always watching the blueprint you set.Buy What You Love (Not Just Like): When you genuinely love the piece, the price stops being the conversation.Liquidity Lens for Steel Sports Rolex: Why a Panda Daytona functions almost like a Royal Oak in terms of value retention and exit options. Key Timestamps(0:00) Intro and wrist check(6:30) Is the Pepsi GMT being discontinued? Insider intel from three ADs(8:15) Who is Karlos Williams: tech exec, entrepreneur, lighthouse(14:45) Wearing luxury watches in corporate tech environments(21:20) Detroit's influence on style, Cartier culture, and remembering D Hasey(26:00) 10and2media and the upcoming Intelligence platform(41:00) First class travel, networking, and why the watch on your wrist opens doors(53:30) Karlos's AD journey and the watches that started it all(1:00:15) Deep dive on the Pikachu Daytona on Oysterflex(1:11:30) Most underrated Rolex picks(1:24:30) Most overrated Rolex and the people who ruin good watches(1:35:00) AD relationship strategy and why one trusted dealer beats many(1:55:30) Rolex vs Porsche: design language and slow refinement(2:01:00) Final advice: be authentic, buy what you love, learn AI#rolex #pepsigmt #gmtmaster2 #watchcollecting #rolexdiscontinued #corporatelife #luxurywatches #careeradvice #authorizeddealer #watchcommunity #watchculture #pikachudaytona

Why does Rolex still dominate the watch world, even when collectors constantly debate the brand online?In this episode, Rod Dye and Rio the Watcher break down why Rolex remains the standard in modern watch culture. From resale value and brand control to the psychology of scarcity and the reality of the authorized dealer process, this conversation goes beyond surface-level Rolex hype and gets into why the crown continues to outperform nearly everyone else.They also unpack what the latest retail and secondary market numbers say about the industry, why brands like Cartier and Richard Mille are thriving in different ways, and why Omega may need to rethink its product and messaging strategy. Along the way, they tackle whether there’s such a thing as a bad Rolex, debate the most underrated and overrated models in the catalog, and build their personal Rolex Mount Rushmores.Things You’ll Learn:Why Rolex’s dominance comes from certainty, restraint, and brand control, not just hypeHow the AD process creates desire, exclusivity, and a sense of achievement for buyersWhich Rolex models Rod and Rio see as the most underrated, overrated, and essential to the brand’s legacyTools / Frameworks Matt Shares: Certainty Principle: Why Rolex wins by giving buyers confidence in value, status, and product consistencyAD Allocation Math: A practical way to understand why demand far exceeds supply at the dealer levelMount Rushmore Test: A simple framework for separating personal favorites from historically essential Rolex models Key Timestamps0:00 – Intro and wrist check05:45 – Rolex leads both retail and secondary market sales10:16 – Is there actually a bad Rolex watch?13:37 – Cartier, Omega, Richard Mille, and the rest of the top 1021:14 – Why Omega may be losing ground26:33 – Why Rolex Wins30:49 – The AD process and whether it’s broken39:49 – Most underrated and overrated Rolex models47:39 – Rolex Mount Rushmore55:32 – Final thoughts on Rolex as a luxury icon#rolex #watchculture #luxurywatches #watchcollecting #explorer1 #airking #watchdebate #watchmarket

What happens when watch collecting starts looking more like derivatives trading? In this episode of The Watchers, Rod Dye and Rio the Watcher unpack the new Bezel x Kalshi partnership and what watch futures could mean for collectors, dealers, and the broader industry. They explore whether this creates useful pricing transparency or simply opens the door to more speculation, manipulation, and ‘DraftKings for watcher.’ They also discuss why the Rolex Datejust remains one of the most important watches in the world, how market data can help buyers, and whether bringing more financial players into the space strengthens watch culture or pulls it further away from what made the hobby meaningful in the first place.Things You’ll LearnWhy watch futures could reshape how collectors think about pricing, liquidity, and market signals.How speculation, dealer behavior, and platform incentives can influence perceived watch value.Why more market data can help buyers, while still creating new risks for manipulation and hype.Tools / Frameworks Matt SharesTransparency vs. Manipulation Lens: A simple way to evaluate whether new market tools help collectors or mainly benefit platforms, dealers, and speculators.Collector vs. Speculator Test: Asking whether participation in watches comes from appreciation of the hobby or purely from financial positioning.Regional Pricing Reality Check: Why a watch’s value can vary by city, dealer, and convenience, even when market price data exists online. Key Timestamps0:00 – Intro and wrist check1:54 – Why the Rolex Datejust is the quintessential Rolex6:33 – Bezel x Kalshi watch futures announcement8:03 – Watch trading or watch gambling?11:40 – Risks of price manipulation and bad actors17:11 – Could Bezel become the central watch market index?19:47 – Why this feels closer to derivatives than traditional collecting21:27 – The case for transparency, analytics, and accessibility23:41 – Conflict-of-interest concerns around Bezel as marketplace and valuation source30:00 – Will watch futures influence real-world prices?35:00 – Is the hobby becoming more about financial instruments than culture?38:48 – Does more speculation actually help the watch community?46:01 – GameStop-style coordination and community-driven market pressure48:36 – Could brands or insiders bet against their own interests?52:01 – Final thoughts on where this could go next#watchculture #watchmarket #collecting #watchvalue #watchinvesting #luxurywatches #watchcommunity #modernicons #marketplace #horology #valuation

What really sits behind the loud opinions on Rolex, Grand Seiko, and modern watch hype? In this episode, Andy Berg, better known as Andy’s Watches, joins to break down watch culture, collecting, and value without gatekeeping. Andy shares his path from blue-collar work and addiction recovery to becoming one of the fastest-rising voices in watchmaking and collecting, unpacks why some collectors “hate” Rolex, and gets candid about Grand Seiko, the Omega Planet Ocean, and which brands actually listen to their community. Along the way, you’ll hear real bench stories, practical buying guidance, and 2 under-$1,000 picks that prove great collecting isn’t about hype or budget, it’s about fit, value, and culture.Things You’ll Learn1. Why loud “Rolex hate” often says more about watch culture than the watches themselves.2. How Andy’s background as a machinist, roofer, welder, and comedian shaped his approach to collecting and content.3. How to think clearly about value when buying watches under $1,000 without chasing hype.Tools / Frameworks Matt Shares- Try-Before-You-Buy (Without Handling It): Using YouTube wrist shots and reference searches to judge size, proportions, and presence.- Brand Listening Meter: How brands like Citizen, Omega, Rolex, Seiko, Grand Seiko, and Baume & Mercier respond (or don’t) to community feedback.- Age & Budget Lens: Why sub-$1,000 recommendations look different for 20-somethings versus 40-somethings.Key Timestamps0:00 - Andys Watches + wrist check 8:30 - Andy's journey and inspiration for doing content13:51 - How “rating watch collections without permission” was born21:03 - Personal style, Rolex vs Grand Seiko34:43 - Advice to new watch collectors41:22 - Why brand ambassadors feel outdated49:25 - 2 watches under $1,000: Hamilton Khaki Expedition vs Cincinnati Watch Company Cincinnatus#watchmaking #collecting #watchculture #brandspotlight #watchvalue #valuation #community #vintagewatches #modernicons #marketplace #buyingguides #repairtips #toolssofthetrade

What actually separates a meaningful watch micro-brand from one built on hype? In this episode, Rod Dye and Rio sit down with Matt Castilla, founder of Rook & Castle, to unpack the real decisions behind designing tank-style watches like La Promencia / Adagio Marino and Carmine Nocturne—from gradient dials and crown details to ultra-limited production runs. Matt shares his journey as a collector-turned-founder, including restoring a vintage Lorus Mickey Mouse watch, lessons learned navigating authorized dealers, and why collecting for value is different from chasing resale. The conversation spans watch culture, restoration stories, brand legacy, and community access, with references to pieces like the Cartier Tank, Oris Hank Aaron, Rolex Datejust “Wimbledon,” Day-Date, Sky-Dweller, Oysterquartz, Patek Philippe Calatrava ref. 1463, Furlan Marri, Movado, Invicta, and a vintage Audemars Piguet gold quartz. This episode offers a clear, grounded look at watchmaking, collecting, valuation, and how new voices are shaping the future of the watch community.Things You’ll Learn1. How dial design, gradients, and light impact perceived value in modern watchmaking2. Why ultra-limited production matters for micro-brands and collectors alike3. How to navigate collecting, restoration, and authorized dealers without gatekeepingTools / Frameworks Matt Shares- Designing watches around dial impact, gradients, and light to create emotional response.- Using ultra-limited production runs to balance exclusivity with accessibility.- Treating watchmaking as legacy-building, not resale speculation.Key Timestamps0:00 – Wrist check + Rook & Castle7:48 - Designing the La Promencia / Adagio Marino & Carmine Nocturne13:45 - What’s next for Rook & Castle and the hardest part18:08 - Pushback, bias, and building as a black founder22:03 – AD experiences, the Oris Hank Aaron, and buying from people who respect you32:54 - Legacy and being first-generation watch enthusiasts46:52 - Where to find Matthew and Rook & Castle#watchculture #community #watchcollecting #watchmaking #brandspotlight #modelhistory #restoration #microbrand #communityfirst #collecting #watchvalue #buyingguides #localshops #watchnews #collectors #modernicons

What starts as a guilt-free year-end watch purchase turns into a full micro-brand when Shakeem Tomlin refuses to pay resale prices and decides to build his own watch instead. In this episode, Rod and Rio sit down with the founder of Tomlin & Co to trace the real journey behind the Celestial Calendar, from early design sketches and movement selection to launching a full calendar moonphase watch built for everyday wear. Shakeem shares how growing up in Philly shaped his approach to collecting and design, why quartz made sense for an entry-level complication piece, how his wife influenced key colorways, and what it’s like navigating watch culture as a Black-owned brand. Along the way, the conversation touches on Rolex Sky-Dweller (mint green), Breitling, Audemars Piguet, integrated bracelets, trade shows, community support, and building value without gatekeeping.Things You’ll Learn1. How Tomlin & Co evolved from a personal watch idea into a launched micro-brand.2. Why the Celestial Calendar uses a full calendar + moonphase quartz movement for everyday collecting.3. How community, culture, and representation shape modern watch culture and brand building.Tools/Frameworks in This Episode- A year-end “guilt-free purchase” ritual as a practical collecting framework.- Using email lists, existing networks, and in-person events to launch a micro-brand.- A “Reasonable Doubt” design philosophy: building one watch that doesn’t feel like it’s missing anything.Key Timestamps0:00 – Tomlin & Co introduction + wrist check7:10 – Shakeem’s Philly background and path into watches11:00 – Designing a do-it-all watch from scratch14:21 – Launching Tomlin & Co and early reception16:37 – Celestial Calendar colorways explained22:23 – Watch inspirations, collecting, and culture25:50 – Trade show rejection and focusing on community29:03 – Why Black culture matters in watch culture31:31 – Future plans: movement house, accessories, collabs33:20 – Where to support Tomlin & Co34:59 – What needs to change in watch culture#watchculture #collecting #brandspotlight #watchnews #watchvalue #community #modernicons

What happens when someone looks at your Rolex and calls it a “modest watch”? In this episode, Rod and Rio sit down with collector and mentor CJ Webster to trace how that moment reshaped his entire approach to collecting, value, and watch culture. From buying a Rolex Datejust 16233 on layaway to earning an Omega Speedmaster allocation and ultimately acquiring a De Bethune DB25 Starry Varius, CJ explains how humility, curiosity, and community accelerate real learning. Along the way, the conversation explores watch culture in Miami and Columbus, why the story behind the watch matters more than hype, and how clubs, books, and local meetups help collectors make better decisions. Watches discussed include the Tissot PRX, Tissot Sideral Powermatic 80, Swatch x Omega Speedmaster, AP Royal Oak, Cartier Santos (including titanium), Omega Seamaster (Planet Ocean and No Time To Die), Hamilton day-date field automatic, Studio Underd0g, Casio, Grand Seiko, Patek Philippe, Vacheron Constantin, IWC, F.P. Journe, Christopher Ward Bell Canto, the Miami Watch Club world-timer, and Rolex references like Pepsi, Batman, Batgirl, Bruce Wayne, and Hulk; all grounded in real collecting experience and community-driven value.Things You’ll LearnHow CJ moved from a layaway Rolex Datejust 16233 to an Omega Speedmaster allocation and a De Bethune grail.How watch community, including Miami Watch Club and 614 Watch Club, accelerates knowledge, access, and buying decisions.Why humility and curiosity matter more than price, specs, or hype in long-term collecting.Buy-What-You-Want Rule: Why settling leads to regret and unworn watches.Community-First Collecting: Using clubs, meetups, and local shops to learn faster and buy smarter.Story-Driven Value: Understanding condition, provenance, and personal history to shape meaningful collections.Tools/FrameworksTimestamps0:00 – Welcome + wrist check7:32 – CJ’s early career and his first Rolex on layaway25:15 – Pride, ego, and emotional connection to watches33:50 – Inside Miami Watch Club and community culture37:17 – The story behind CJ’s Omega Speedmaster46:56 – Going back to Rolex49:36 – Fast cars, watches, cigars, and manhood55:09 – Advice for new collectors: humility and curiosity#watchcollecting #watchculture #watchcommunity #watchvalue #rolexdatejust #omegaspeedmaster #debethune

How does a 26-year-old day trader go from a bust-down Datejust to a single Richard Mille he’s ready to trade for a house? In this conversation, Rod and Rio sit with collector Sire Abram to trace his path from early trading wins in Iowa to building a focused collection rooted in watch value, risk management, and real-world marketplace dynamics. Sire breaks down the jump from bust-downs to Royal Oaks and Daytonas, how he navigates AD vs grey market plays, why some references hold emotional weight, and how he treats watches as both cultural artifacts and strategic assets. Listeners get a grounded look at buying right, collecting with intention, and understanding the psychology behind grails like the John Mayer Daytona and RM 10.What You’ll Learn1. How a day-trader mindset translates into watch collecting, value retention, and smart exits.2. How AD vs grey strategies shape long-term watch value, especially for Rolex, AP, and Patek.3. Why community, culture, provenance, and shared enthusiasm matter when building a modern collection.Tools/Frameworks Mentioned- Buy Right or Don’t Buy Framework- Experience + Exit Mindset- Leverage the Watch StrategyTimestamps:0:00 Intro & Wrist Check2:26 From Iowa to Day-Trading “Proof of Concept”3:24 Who Actually Succeeds at Trading?4:30 First Big Watch: The Bust-Down Datejust Era6:42 Turning Down Goldman Sachs for Trading9:38 From Bust-Down to “Classy”: Datejust to Royal Oak11:12 Hitting Grails: 5711, Day-Date, John Mayer Daytona17:32 Do High-End Watches Really Change Your Life?19:35 Why AP Didn’t Hit & How RM Entered the Chat23:51 Using an RM as Equity28:56 Omega Discoveries & Value Traps30:16 Where to Find Sire + Dream Watch & Price Rules32:52 Final Advice: Enjoy the Process, Not Just the Grails#WatchCollecting #RichardMille #RolexCollector #GreyMarketWatches #PatekPhilippe #AudemarsPiguet

Most new collectors rush in, chase hype, and fill a watch box without understanding what truly fits their style or long-term goals.In this episode of The Watchers, Rod Dye and Rio break down their 10 keys to watch collecting after a full year of hands-on learning, buying, selling, and refining. They walk you through the 10 keys to becoming a successful watch collector, including how to buy what you like, and why research brand heritage and movements matters. Along the way, they debunk investment myths, highlight the power of community, and show how collecting becomes more meaningful when you understand the craft and enjoy the journey.What You’ll Learn- Why buying what you like beats chasing hype and how personal style drives a meaningful collection.- What “investment vs enjoyment” really means in watch collecting and why most pieces aren’t investment grade.- How brand history, design DNA, and movements shape your preferences and long-term satisfaction.- Why curation over accumulation leads to a stronger 5–10 watch lineup you actually love wearing.- How provenance, condition, and “buying the seller” protect you in the marketplace.Tools/Frameworks Mentioned- The 10 Keys of Watch Collecting- Buy the Seller, Not Just the Watch Filter- Curation Over Accumulation LensChapters00:00 – Watches are not investments01:31 – Wrist Check05:02 – 10 Key to watch collecting05:24 - Key #1: Buy What You Like08:57 – Key #2: Know Your Why 13:31 – Key #3: Do Your Research (Brand & Heritage)13:54 – Key #4: Master the Movements15:03 – Key #5: Curation Over Accumulation18:52 – Key #6: Buy the Seller, Not Just the Watch20:57 – Key #7: Providence Matters25:25 - Key #8: Value Over Price27:51 – Key #9: Wear What You Own30:00 – Key #10: Enjoy the Journey⁠#10KeystoCollecting⁠ ⁠#BuyTheSeller⁠ ⁠#CurationOverAccumulation⁠ ⁠#WatchBoxStrategy⁠ ⁠#CollectorMindset⁠ ⁠#KnowYourWhy⁠