Two Guys, Two Questions

Ryan Keeton & Jarrod Greer
  • 5.0 (3)
  • COMEDY
  • UPDATED WEEKLY

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. 🎙️😂

  1. Business or Friendship? - EP 42

    JAN 17

    Business or Friendship? - EP 42

    Join Ryan & Jarrod in this candid and engaging episode of Two Guys, Two Questions. They take you behind the scenes of life’s messiness, from purchasing a massive comic book collection to navigating the complexities of working with friends in business. With humor and raw honesty, they reflect on the challenges of maintaining friendships in a professional setting and the impact of expectations on personal relationships. The episode also touches on funny and insightful stories from their personal lives, including New Year’s adventures, internet flings from the '90s, and learning how to balance the pursuit of money with the value of experiences. Get ready for a mix of hilarious anecdotes and thoughtful reflections on life, growth, and friendship. 🎧 Hosted by: Ryan & Jarrod 💡 What You’ll Hear: ✔️ A fascinating comic book collection story and why memories matter more than money ✔️ The tricky balance of friendship and business, and why the buddy system isn’t always easy ✔️ Personal stories about New Year's and a trip to the beach that turned into a hilarious adventure ✔️ Lessons learned from the pressures of mixing work and personal life ✔️ Thoughts on monetizing hobbies and why it can kill the joy of doing what you love ✔️ Reflections on loyalty, boundaries, and expectations in friendships 📇 Connect with the Guys: 📘 Facebook → https://www.facebook.com/twoguystwoquestionspodcast 📷 Instagram → https://www.instagram.com/twoguystwoquestionspodcast/ 🔗 Spotify → https://open.spotify.com/show/55biAbx1bhTGWjdjox9BDo 🔖 Like, Follow & Leave a Review — or we’ll replace you with a giant python. 🐍 ⭐ Produced by Icons of Real Estate – iconsofrealestate.com

    48 min
  2. Two guys, no Camera - EP 41

    JAN 3

    Two guys, no Camera - EP 41

    In this episode of Two Guys, Two Questions, Ryan and Jarrod reflect on work-life balance, personal growth, and the pressure to turn everything into a job. Through stories about Amish real estate transactions, craftsmanship, holiday traditions, friendships, and Comic-Con memories, the conversation explores slowing down, appreciating the present, and finding joy without constantly chasing the next goal. 🎧 Hosted by: Ryan & Jarrod 💡 What You’ll Hear: ✔️ Amish culture, work ethic, and real-world real estate challenges ✔️ Navigating nontraditional transactions without modern technology ✔️ Holiday traditions and redefining what celebration really means ✔️ Family dynamics and the importance of chosen friendships ✔️ Why monetizing everything can steal joy ✔️ Reflections on balance, perspective, and being present ✔️ Comic-Con stories and lessons from unexpected experiences 📇 Connect with the Guys: 📘 Facebook → https://www.facebook.com/twoguystwoquestionspodcast 📷 Instagram → https://www.instagram.com/twoguystwoquestionspodcast/ 🔗 Spotify → https://open.spotify.com/show/55biAbx1bhTGWjdjox9BDo 🔖 Like, Follow & Leave a Review — or we’ll replace you with a giant python. 🐍 ⭐ Produced by Icons of Real Estate – iconsofrealestate.com

    42 min
  3. The zoo - EP 40

    12/20/2025

    The zoo - EP 40

    In this episode of Two Guys, Two Questions, Ryan dives into the mental side of entrepreneurship—processing big decisions, self-doubt, and the emotional weight that can follow major changes. He reflects on selling a building that is now owned by Jarrod, who operates a reptile business out of the space, and what it feels like to watch someone else step fully into an opportunity you once considered. This candid conversation explores mindset, comparison, confidence, and learning to trust your decisions even when doubt creeps in later. 🎧 Hosted by: Ryan & Jarrod 💡 What You’ll Learn: ✔️ Why doubt often shows up after decisions are made ✔️ How comparison can distort confidence ✔️ The importance of trusting your past choices ✔️ Reframing regret into reflection ✔️ Why growth often feels uncomfortable 📇 Connect with the Guys: 📘 Facebook → https://www.facebook.com/twoguystwoquestionspodcast 📷 Instagram → https://www.instagram.com/twoguystwoquestionspodcast/ 🔗 Spotify → https://open.spotify.com/show/55biAbx1bhTGWjdjox9BDo 🔖 Like, Follow & Leave a Review — or we’ll replace you with a giant python. 🐍 ⭐ Produced by Icons of Real Estate – iconsofrealestate.com

    52 min
  4. TikTok Terrors -EP 39

    12/13/2025

    TikTok Terrors -EP 39

    Join Ryan and Jarrod in this fun and engaging episode of Two Guys, Two Questions, where they discuss everything from failed fishing trips to the strange workings of social media algorithms. They break down the "Happy Holidays vs. Merry Christmas" debate, talk about the impact of social media on society, and dive into personal stories, including Jarrod’s reptile show and Ryan's ongoing home generator dilemma. Plus, they reflect on the future of their podcast and the possibilities for monetization. 🎧 Hosted by: Ryan & Jarrod 💡 What You’ll Learn: ✔️ The unexpected effects of TikTok’s algorithm ✔️ Funny fishing stories and personal experiences ✔️ The pros and cons of installing a home generator ✔️ A heated discussion on Christmas greetings ✔️ Tyler Childers and controversial opinions on music ✔️ Social media’s role in shaping today’s culture ✔️ The podcast’s goals and potential monetization ideas ✔️ How algorithms influence personal preferences and content consumption 📇 Connect with the Guys: 📘 Facebook → https://www.facebook.com/twoguystwoquestionspodcast 📷 Instagram → https://www.instagram.com/twoguystwoquestionspodcast/ 🔗 Spotify → https://open.spotify.com/show/55biAbx1bhTGWjdjox9BDo 🔖 Like, Follow & Leave a Review — or we’ll replace you with a giant python. 🐍 ⭐ Produced by Icons of Real Estate – iconsofrealestate.com

    52 min
  5. Black Friday Strategies - EP 38

    12/06/2025

    Black Friday Strategies - EP 38

    Join Ryan and Jarrod as they talk through retail sales strategies during Black Friday, the realities of real estate negotiations, and personal stories that bring humor and wisdom. From Ryan's perspective on retail promotions to Jarrod’s tips on crafting thoughtful offers, this episode has it all. They also share a bit of personal life, discussing everything from their families to their biggest learning moments in business. Plus, Ryan’s violin saga brings a unique twist to the conversation! 🎙 Key Topics Discussed ✔️ Black Friday Sales Strategies – What works and what doesn't ✔️ The impact of big sales events on retail business ✔️ How to handle real estate negotiations without getting stuck in arbitrary offers ✔️ The evolving commercial property market and downtown revitalization ✔️ The personal side of business – Family dynamics, mental health, and balancing life ✔️ Real-world stories: Violin sales, holiday experiences, and unexpected wins 📇 Connect with the Guys: 📘 Facebook → https://www.facebook.com/twoguystwoquestionspodcast 📷 Instagram → https://www.instagram.com/twoguystwoquestionspodcast/ 🔗 Spotify → https://open.spotify.com/show/55biAbx1bhTGWjdjox9BDo 🔖 Like, Follow & Leave a Review — or we’ll replace you with a giant python. 🐍 ⭐ Produced by Icons of Real Estate – iconsofrealestate.com

    48 min
  6. Costa Rica Adventures - EP 37

    11/22/2025

    Costa Rica Adventures - EP 37

    In this unfiltered episode of Two Guys, Two Questions, Ryan returns from Costa Rica with stories of jet skis, jungle tours, wild monkeys, and a resort full of persistent hustlers who somehow remembered his name… even when he didn’t tell them. Meanwhile, Jarrod  confesses to accidentally acquiring 35 new snakes—including multiple 10-foot monsters—and realizing he may have officially become a reptile hoarder. The guys also break down a shocking real estate clean-out story involving a $6,000 “trash removal fee,” a dumpster full of valuable vintage toys, and a missed business opportunity they’re now seriously considering. From holiday traditions and Christmas chaos to debates about future tech, typing skills, and why beards may age terribly—this episode is everything the show promises: two guys, two questions, and absolutely zero direction. 💡 Highlights: ✔️ Ryan’s Costa Rica adventures: monkeys, ATVs & overpriced Ray-Bans ✔️ Jarrod s snake collection spiraling way out of control ✔️ The $6,000 clean-out job that turned treasure into trash ✔️ Dumpster diving for vintage toys worth real money ✔️ Christmas chaos: Griswold vs. Scrooge energy ✔️ Why future generations may never learn to drive ✔️ The tech that will make this decade look ancient 📇 Connect with the Guys: 📘 Facebook → https://www.facebook.com/twoguystwoquestionspodcast 📷 Instagram → https://www.instagram.com/twoguystwoquestionspodcast/ 🔗 Spotify → https://open.spotify.com/show/55biAbx1bhTGWjdjox9BDo 🔖 Like, Follow & Leave a Review — or we’ll replace you with a giant python. 🐍 ⭐ Produced by Icons of Real Estate – iconsofrealestate.com

    53 min
  7. Miami Madness - EP 36

    11/08/2025

    Miami Madness - EP 36

    Ryan reports in from Miami and Jarrod returns from ScareFest in a chaotic, hilarious, and oddly reflective episode of Two Guys, Two Questions. They cover everything from wild Key West people-watching to a moral debt that’s been eating at Ryan for decades, plus the costs (financial and emotional) of being deeply invested in reptiles. This one’s for people who like their comedy with a side of conscience. 💡 Key Highlights: ✔️ Fantasy Fest & Key West antics ✔️ Calendar automation with ChatGPT (life organized, sanity questionable) ✔️ Ethics: do you fix a 30-year-old wrong? ✔️ Reptile hobby confessions & why snakes are terrible investments ✔️ Family check-ins, car accidents, and nostalgic recipes 🎙 Follow Ryan & Jarrod: 📘 Facebook → https://www.facebook.com/twoguystwoquestionspodcast 📷 Instagram → https://www.instagram.com/twoguystwoquestionspodcast/ 🔗 Spotify → https://open.spotify.com/show/55biAbx1bhTGWjdjox9BDo 🔖 Like, Follow & Leave a Review — or we’ll replace you with a giant python. 🐍 ⭐ Produced by Icons of Real Estate – iconsofrealestate.com

    52 min
  8. You Got Small again - EP 35

    11/01/2025

    You Got Small again - EP 35

    Ryan checks in from Miami Beach while Jarrod shares post-con chaos from ScareFest. Between talk of cocaine jokes, AI breakthroughs, cult beards, and financial awakenings, this episode is the perfect mix of absurdity and insight. 🎧 Hosted by: Ryan & Jarrod 💡 Key Highlights: ✔️ How AI is reshaping business and saving thousands ✔️ Real estate lessons and the art of recovery ✔️ Spreadsheet enlightenment and life lessons ✔️ Beach therapy, bad ideas, and brilliant moments ✔️ Why chaos might be the best business strategy 🎙 Follow Ryan & Jarrod: 📘 Facebook → https://www.facebook.com/twoguystwoquestionspodcast 📷 Instagram → https://www.instagram.com/twoguystwoquestionspodcast/ 🔗 Spotify → https://open.spotify.com/show/55biAbx1bhTGWjdjox9BDo 🔖 Like, Follow & Leave a Review — or we’re replacing you with AI! 🤖 ⭐ Produced by Icons of Real Estate – iconsofrealestate.com

    43 min
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Trailer

Ratings & Reviews

5
out of 5
3 Ratings

About

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. 🎙️😂

Information

  • Creator
    Ryan Keeton & Jarrod Greer
  • Years Active
    2025 - 2026
  • Episodes
    43
  • Rating
    Explicit
  • Copyright
    © Ryan Keeton & Jarrod Greer
  • Show Website
    Two Guys, Two Questions