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Two Guys, Two Questions

Ryan Keeton & Jarrod Greer
Two Guys, Two Questions
Latest episode

69 episodes

  • Two Guys, Two Questions

    Spend It Before You Die? Inheritance, Heirlooms & Your Kids

    14/10/2026 | 49 mins.
    🔬 Should you spend every dollar before you die, or leave it to your kids? Two friends argue inheritance, heirlooms and what 25-year-old you got wrong.
    When does saving for your kids start costing you your own life, and does an inheritance actually help the people who get it?
    Ryan Keeton, a real estate agent, and his co-host Jarrod, a reptile breeder and convention promoter who also buys estates and resells their collectibles, trade real stories: a friend's $450,000 inheritance, a will that skips the grandkids and a dad selling gold coins to his own son.
    You'll hear whether to spend it or leave it, why your stuff may burden your kids, what we believed at 25 about money and work, and how to help grown kids with money.
    🎙️ WHAT WE'RE TALKING ABOUT:
    ✔️ Saving for your heirs can mean never fully living your own life 
    ✔️ Teaching kids to earn money early is a habit of many wealthy parents 
    ✔️ Heirloom clutter often means little to the next generation 
    ✔️ Underinsured storage is a risk: no inventory means guessing after a loss 
    ✔️ The money goalpost keeps moving: $100K a year never feels like rich 
    ✔️ Backup plans make failure affordable: keep a day job while you build 
    ✔️ Skipping a big wedding can still end in a costly Hawaii honeymoon 
    Follow for next week's questions. 
    _____________
    ⏳ Key Questions Answered in This Episode :
    Q: What's the risk of a retiree keeping all their money in the stock market?
    → A: The risk, as Jarrod, a reptile breeder and convention promoter, describes it, is outliving the money: his 77-year-old father is fully and aggressively invested in the market, and Jarrod worries his dad could live another 25 years while the money evaporates in five. His father's answer is that it's Jarrod's money anyway, so it should stay in the market making money. 
    Q: How can I chip in for a wedding honeymoon fund without spending cash?→ A: Ryan Keeton covered his son's entire $1,000 honeymoon fund on an Amazon wedding registry with credit card points, because his points spend dollar for dollar on Amazon.
    Q: Why can a sudden inheritance turn out badly for the person who gets it?→ A: Jarrod believes a longtime friend's $450,000 cash inheritance will be a bad thing for him because the friend worked hard most of his life for what little he had and is now likely to go "plum off the deep end." The friend has already said he is heading to Thailand.
    _____________
    ⏳ TIMESTAMPS:
    00:00 - Cold Open: A $450K Inheritance 

    00:40 - Road Burnout & ChatGPT Ad Campaigns 

    06:00 - AI Ads vs. Human Art

    11:41 - Selling Houses & a VA Program 

    13:44 - Should Money Be Inherited? The $450K Story 

    17:36 - One-Generation Wills & Spending It Before You Die

    19:33 - A 77-Year-Old in the Market & Grandpa's Gold Coins

    24:16 - Hoarded Stuff & the Lost Storage Unit 

    29:07 - What You Believed at 25: $100K vs. $10K 

    31:03 - Safe Job vs. Side Hustle 

    36:21 - Parents Are Human & Aging Is a Cruel Joke 

    42:06 - Vegas Wedding to Hawaii Honeymoon 

    45:40 - A $300 Snake-Catching Honeymoon 

    _____________
    🎧 HOSTED BY:
    • Ryan Keeton – Real Estate Investor & Top Producing Broker
    • Jarrod Greer – Comic Con Organizer & Serial Entrepreneur
    Join Ryan and Jarrod on Two Guys, Two Questions as they ask each other one surprise question per episode – with zero prep, no rules, and pure unfiltered fun. From alligators to superheroes, business to life, it's pure chaos. Buckle up! 😂
    👉🏻 FOLLOW TWO GUYS, TWO QUESTIONS:
    • Facebook: https://www.facebook.com/twoguystwoquestionspodcast
    • Instagram: https://www.instagram.com/twoguystwoquestionspodcast
    Don’t forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 below! 
    💎 Produced by Icons of Real Estate https://iconsofrealestate.com/
    #TwoGuysTwoQuestions #LexingtonComicCon #ComicConLife #ConventionBusiness #ToyCollecting #PopCulturePodcast #SpotifyPodcast #BehindTheScenes
  • Two Guys, Two Questions

    Torn-Up Cash, Ignored Texts: Ryan Keeton & Jarrod's Wild Week

    30/09/2026 | 57 mins.
    🔬 A reptile show fight ends with torn-up cash, then a debate over whether you even have to reply to a text. 
    On this episode, Ryan Keeton and Jarrod dig into a real confrontation at a reptile show: a self-described "rescue" group accused Jarrod of starving newly hatched ball pythons, demanded a refund, and pushed until he tore up the cash and walked away. 
    Listen for how two guys who disagree on plenty still land on where the line actually is between standing your ground and being the problem. 
    🎙️ WHAT WE'RE TALKING ABOUT:
    ✔️ Public accusations don't require an immediate defensive reaction 
    ✔️ Walking away often ends conflict faster than continuing to argue 
    ✔️ "No refunds" policies work best with zero exceptions 
    ✔️ Redlining a contract can protect you, even at a cost 
    ✔️ Cutting off a pushy salesperson early avoids bigger problems 
    ✔️ Texting etiquette differs sharply between generations 
    ✔️ Refund disputes over factors outside your control need firm boundaries 
    ✔️ Clear reasoning still builds trust with people who disagree 
    Follow for next week's questions. 
    _____________
    ⏳ Key Questions Answered in This Episode :
    Q: How should a business respond when a customer publicly accuses it of wrongdoing?
    → A: The most effective response is to offer a clear, reasonable resolution, such as a refund or reversing the transaction, and then disengage once the accuser keeps escalating past that point, rather than continuing to argue in public. Publicly explaining your reasoning once is usually enough; repeating it only feeds further escalation. 
    Q: What is a "no refunds" policy at a live convention?→ A: It's a fixed rule, confirmed by the buyer at checkout, that ticket, meet-and-greet, or photo fees are non-refundable regardless of guest cancellation.
    Q: Why does redlining a contract sometimes cost an agent a deal?→ A: Striking clauses the agent believes don't protect the client can conflict with a rigid boilerplate contract the other party refuses to change.
    ⏳ TIMESTAMPS:
    00:00 - Cold Open: Torn-Up Cash 

    00:21 - Travel Plans & Fraternity Reunion 

    04:34 - Breeding Ball Pythons Explained 

    07:17 - "Are These Yours?" 

    09:00 - Twist: "We're A Reptile Rescue" 

    11:07 - The Confrontation Escalates 

    12:46 - Tearing Up $125 In Cash

    14:13 - The Deleted Facebook Post 

    21:34 - Firing An Insurance Salesman 

    25:40 - Do You Owe A Reply? 

    32:24 - Unread Texts & Emails 

    38:55 - The Celebrity Photo Refund Fight 

    44:26 - Are You Open To Being Told You're Wrong?

    48:25 - Why I Redline Every Contract 

    54:42 - Is Owning A Home Worth It? 

    🎧 HOSTED BY:
    • Ryan Keeton – Real Estate Investor & Top Producing Broker
    • Jarrod Greer – Comic Con Organizer & Serial Entrepreneur
    Join Ryan and Jarrod on Two Guys, Two Questions as they ask each other one surprise question per episode – with zero prep, no rules, and pure unfiltered fun. From alligators to superheroes, business to life, it's pure chaos. Buckle up! 😂
    👉🏻 FOLLOW TWO GUYS, TWO QUESTIONS:
    • Facebook: https://www.facebook.com/twoguystwoquestionspodcast
    • Instagram: https://www.instagram.com/twoguystwoquestionspodcast
    Don’t forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 below! 
    💎 Produced by Icons of Real Estate https://iconsofrealestate.com/
    #TwoGuysTwoQuestions #LexingtonComicCon #ComicConLife #ConventionBusiness #ToyCollecting #PopCulturePodcast #SpotifyPodcast #BehindTheScenes
  • Two Guys, Two Questions

    S2E1: Governor Crashes Comic Con, 50 Fan Letters Uncovered

    16/09/2026 | 1h 2 mins.
    🔬 A governor crashed Comic Con, a fan left 50 letters, and someone got accused of theft, welcome to Season 2 of Two Guys, Two Questions.
    What happens when a governor shows up unannounced at your comic convention and a superfan leaves a box of love letters for a celebrity guest?
    Hosted by Ryan Keeton, a Kentucky-based comic convention and reptile show promoter who runs Lexington Comic-Con, alongside co-host Jarrod Greer, the show opens Season 2 with a recap of Ryan's fall weekend: an art theft accusation, an attendee injury, and a viral governor Facebook post that started earning ad revenue on its own.
    Listeners get a behind-the-curtain look at running a convention, plus the show's signature questions on dating, celebrity obsession, and what modern life is quietly costing us. 
    🎙️ WHAT WE'RE TALKING ABOUT:
    ✔️ Refund first, no guilt assumed: handling a Comic-Con theft claim.
    ✔️ One-room layout, better turnout: Lexington Comic-Con's smaller show wins.
    ✔️ Inside a fan's 50-letter "parasocial leech" confession.
    ✔️ Costume contests lose money, comic cons run them anyway. Here's why.
    ✔️ A governor's surprise visit becomes a monetized viral post.
    ✔️ Looks vs. personality: the real answer, no sugarcoating.
    ✔️ Six years, then it's gone: the lost-and-found rule at events.
    ✔️ AI and same-day delivery are quietly erasing this skill.
    Run events, collect toys, or love a debate? Follow for next week's questions. 
    _____________
    ⏳ Key Questions Answered in This Episode :
    Q: How does a comic convention organizer handle a theft accusation? → A: Security removes the accused party as standard policy, and since the organizer wasn't present to verify what happened, his follow-up move is to offer a refund rather than assume guilt.
    Q: What is a "parasocial leech" in fan-celebrity culture? → A: A phrase pulled from one of 50 sealed letters a fan left for a celebrity guest, describing an intense one-sided attachment toward someone they've barely met.
    Q: Why did local news cover the Facebook post instead of the governor's visit itself? → A: The station skipped the convention, but ran a story on the organizer's post once it went viral and sparked arguments, driving more traffic to it.
    _____________
    ⏳ TIMESTAMPS:
    [00:00] - Cold Open: Cold Open: 50 Fan Letters 
    [01:00] - Camel Commercial Nostalgia 
    [02:51] - 8 Weekends of Cons in a Row 
    [03:39] - Sorting a Mystery Toy Haul 
    [06:24] - Season 2 Premiere Begins 
    [07:24] - Recapping the Fall Comic Con 
    [09:51] - Wild Convention Guest Moments 
    [12:36] - Investigating an Art Theft 
    [14:05] - Convention Injury Risks 
    [15:31] - Full Story: 50 Fan Letters 
    [21:08] - The 6-Year Lost & Found Rule 
    [22:30] - Costume Contests & Cosplay Drama 
    [25:36] - Governor Crashes Comic Con 
    [30:59] - Looks vs. Personality Debate 
    [34:35] - Would They Try Love Is Blind? 
    [43:40] - Honesty, Farting & Relationships 
    [50:54] - Employees Who Stick Around 
    [53:08] - What Has Civilization Lost? 
    _____________
    🎧 HOSTED BY:
    • Ryan Keeton – Real Estate Investor & Top Producing Broker
    • Jarrod Greer – Comic Con Organizer & Serial Entrepreneur
    Join Ryan and Jarrod on Two Guys, Two Questions as they ask each other one surprise question per episode – with zero prep, no rules, and pure unfiltered fun. From alligators to superheroes, business to life, it's pure chaos. Buckle up! 😂
    👉🏻 FOLLOW TWO GUYS, TWO QUESTIONS:
    • Facebook: https://www.facebook.com/twoguystwoquestionspodcast
    • Instagram: https://www.instagram.com/twoguystwoquestionspodcast
    Don’t forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 below! 
    💎 Produced by Icons of Real Estate https://iconsofrealestate.com/
    #TwoGuysTwoQuestions #LexingtonComicCon #ComicConLife #ConventionBusiness #ToyCollecting #PopCulturePodcast #SpotifyPodcast #BehindTheScenes
  • Two Guys, Two Questions

    Dolly, Tim Curry, and Trading Away Your Vanity

    05/09/2026 | 48 mins.
    🔬 A newborn, a VA rebuilt from scratch, and the week Dolly, Tim Curry & Optimus Prime's voice all died. Two friends unpack it all.
    This week, one host is knee-deep in retraining a six-year VA whose old workflow no longer fits the business, while closing two new real estate listings on almost no sleep. The other is loading trucks sick as a dog ahead of his annual convention, wrangling a governor's schedule, and negotiating an art collection out of a documentary filmmaker's widow. Between the two, the conversation swings from a vanity thought-experiment to one of the most genuinely moving stories either of them has told on the show. 
    🎙️ WHAT WE'RE TALKING ABOUT:
    ✔️ How to rebuild a six-year working relationship with an employee whose workflow no longer fits the business 
    ✔️ Why creative collaborators need ownership and how to work with that instead of against it  
    ✔️ What a simple thought experiment reveals about the real cost of vanity 
    ✔️ How to spot value other people walk right past (the dumpster-photos-into-a-book story) 
    ✔️ How to negotiate patiently with a meticulous, well-researched seller 
    ✔️ What it means to give someone "their life back" before the end 
    ✔️ How to hold onto your identity even when no one expects anything of you 
    _____________
    🎧 HOSTED BY:
    • Ryan Keeton – Real Estate Investor & Top Producing Broker
    • Jarrod Greer – Comic Con Organizer & Serial Entrepreneur
    Join Ryan and Jarrod on Two Guys, Two Questions as they ask each other one surprise question per episode – with zero prep, no rules, and pure unfiltered fun. From alligators to superheroes, business to life, it's pure chaos. Buckle up! 😂
    👉🏻 FOLLOW TWO GUYS, TWO QUESTIONS:
    • Facebook: https://www.facebook.com/twoguystwoquestionspodcast
    • Instagram: https://www.instagram.com/twoguystwoquestionspodcast
    Don’t forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 below! 
    💎 Produced by Icons of Real Estate https://iconsofrealestate.com/
  • Two Guys, Two Questions

    Ordering Cobras at 17, HBO Drama & The Species Myth

    29/08/2026 | 1h 1 mins.
    🔬 From seven nights of grandkid duty and yard pin metal detectors to high-stakes exotic trade history, Ryan and Jarrod cover it all on Two Guys, Two Questions. Dive into old-school stories like mail-ordering live cobras at 17, the fallout from HBO's Monsters of God docuseries, and why Mother Nature ignores human scientific definitions.
    🎙️ WHAT WE'RE TALKING ABOUT:
    ✔️ Real-life updates, $20k expo wins, and local eco-store debates
    ✔️ The backroom tension behind HBO's Monsters of God director Q&A
    ✔️ How commercial breeding is protecting rare animals like the Borneo earless lizard
    ✔️ Why wildlife laws planning around static science are set up to fail
    _____________
    🎧 HOSTED BY:
    • Ryan Keeton – Real Estate Investor & Top Producing Broker
    • Jarrod Greer – Comic Con Organizer & Serial Entrepreneur
    Join Ryan and Jarrod on Two Guys, Two Questions as they ask each other one surprise question per episode – with zero prep, no rules, and pure unfiltered fun. From alligators to superheroes, business to life, it's pure chaos. Buckle up! 😂
    👉🏻 FOLLOW TWO GUYS, TWO QUESTIONS:
    • Facebook: https://www.facebook.com/twoguystwoquestionspodcast
    • Instagram: https://www.instagram.com/twoguystwoquestionspodcast
    Don’t forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 below! 
    💎 Produced by Icons of Real Estate https://iconsofrealestate.com/
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About Two Guys, Two Questions
Two guys. Two questions. Endless tangents. Join Ryan Keeton, a real estate guy & VR golfer with beach bum dreams, and Jarrod Greer, a Comicon & retro toy store owner who insists his action figures aren’t dolls, as they ask each other one surprise question per episode—no prep, no rules, just chaos. From alligators to vibrators, superheroes to world problems, nothing’s off-limits. Add a monthly mystery guest, some pesky French bulldogs, and at least one existential crisis per episode—this podcast makes no sense… but in the best way. Buckle up. It’s gonna get weird. 🎙️😂
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