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Two Guys, Two Questions

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

66 episodes

  • 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/
  • Two Guys, Two Questions

    Scaling Past $3M & Real Hustle Secrets | Two Guys, Two Questions

    15/08/2026 | 1h
    💡 Propofol naps, Puerto Rico travel chaos, and trolling Grant Cardone’s AI text bot. Ryan and Jared are back to talk small business reality, $3M revenue walls, and why sitting on warehouse inventory is a nightmare.
    Plus: how loaning $1,300 for Air Jordans taught a kid real financial literacy, busting tax myths, and why AI still can’t teach kids actual life skills.
    🎙 In this episode, we cover:
    ✔️ The Neato stress ball craze and managing secondary market mania
    ✔️ The 30-Day Disappearance Test: Is your business dependent on you?
    ✔️ Decoupling personal identity from round-the-clock work
    ✔️ Ditching handouts: Teaching kids financial literacy and resilience
    _____________
    🎧 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! (Before Jarrod buys another warehouse full of action figures)
    💎 Produced by Icons of Real Estate https://iconsofrealestate.com/
  • Two Guys, Two Questions

    The 30-Day Business Test, The Neato Frenzy, & The Guilt of Slowing Down

    18/07/2026 | 55 mins.
    In this episode of Two Guys, Two Questions, Ryan and Jarrod kick things off with a little banter about punctuality before diving into a wild story about a close call on the road. Jarrod then shares the chaotic tale of "Neatos" - a wildly popular stress ball that caused a literal line around the block at his store, leading to some serious Facebook drama and a surprisingly deep dive into the ethics of supply and demand.
    The conversation then shifts to the main question: What would happen to your business if you disappeared for 30 days with only an hour's notice? The guys break down the realities of delegating, the difference between a job and a business, and what it truly takes to step away from the grind. They also touch on the fear of aging without enough money, the struggle of redefining "work" in a pseudo-retirement, and the surprisingly poignant moments of past financial struggles.
    🎧 Hosted by: Ryan & Jarrod
    💡 What You’ll Learn in This Episode:
    ✔️ The Neato Phenomenon: How a simple stress ball created a secondary market frenzy.
    ✔️ The 30-Day Disappearance Test: A thought experiment on how resilient a business truly is without its owner.
    ✔️ The Cost of "Not Working": A candid discussion on the guilt that comes with stepping back from a demanding work schedule.
    ✔️ The Fear of the Future: Exploring the anxiety of aging and outliving your money.
    ✔️ From Rock Bottom to Here: Ryan and Jarrod reflect on their past financial struggles.
    🎙 Follow Two Guys, Two Questions:
    📘 Facebook → https://www.facebook.com/twoguystwoquestionspodcast
    📷 Instagram → https://www.instagram.com/twoguystwoquestionspodcast/
    🔗 Spotify → https://open.spotify.com/show/55biAbx1bhTGWjdjox9BDo
    🔖 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! (Or we're bringing back the squeaky toys)
  • Two Guys, Two Questions

    Exploding Toilets, Vintage Cars, and The Future of the Podcast with Ryan & Jarrod

    11/07/2026 | 43 mins.
    In this episode of Two Guys, Two Questions, hosts Ryan and Jarrod catch up after a wild week. Jarrod returns from Texas with a stomach bug that turns his first four days back into an absolute nightmare. After surviving his illness, he’s back to report the realities of juggling 900 snakes, planning three reptile expos in one weekend, and dealing with an ever-growing list of tasks.
    Together, the guys discuss the struggle of turning off a "manic head space," what it’s like to go to a classic car auction with zero cash, and the realities of solo beach trips to Myrtle Beach. The episode takes a surprisingly philosophical turn when they debate what they would show an alien if it landed on Earth, and whether humanity would actually do anything to stop an impending, world-ending meteor.
    🎧 Hosted by: Ryan & Jarrod
    💡 What You’ll Learn in This Episode:
    ✔️ The Texas Stomach Bug: A hilarious recounting of surviving an explosive stomach bug.
    ✔️ The "Manic Head Space": The struggle of trying to balance a massive snake collection and multiple conventions.
    ✔️ Car Auctions with No Money: Why going to a vintage car auction with zero cash is a painful but smart choice.
    ✔️ The Podcast Inflection Point: A candid discussion about the future of the podcast and finding mental health value in just shooting the shit with a friend.
    ✔️ Aliens & Meteors: What would you show an alien to confuse them?
    🎙 Follow Two Guys, Two Questions:
    📘 Facebook → https://www.facebook.com/twoguystwoquestionspodcast
    📷 Instagram → https://www.instagram.com/twoguystwoquestionspodcast/
    🔗 Spotify → https://open.spotify.com/show/55biAbx1bhTGWjdjox9BDo
    🔖 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! (Or we're bringing back the squeaky toys)
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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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