Two Guys, Two Questions

In this episode of Two Guys, Two Questions, Ryan & Jarrod bounce from business chaos into something much deeper. What starts as a catch-up about moving buildings and slow winter months turns into a real conversation about collectibles, contracts, regret, mortality, and what your “stuff” is actually worth.
From warehouse-sized buying decisions to AI confidently getting snake medication wrong, this one goes everywhere — and somehow still lands on a question that’ll stick with you:
If you could know the exact date and cause of your death — but couldn’t change it — would you want to know?
🎧 Hosted by: Ryan & Jarrod
💡 What You’ll Hear:
✔️ Why collectibles can lose value fast when you’re forced to sell
✔️ The warehouse decision that changed everything
✔️ Contracts, fear, and analysis paralysis
✔️ The reality of non-competes and enforcement
✔️ AI getting things confidently wrong
✔️ A collector story that turns into a lesson on legacy
✔️ Why most “valuable” stuff becomes someone else’s problem
✔️ The death-date question that flips the whole episode
📇 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 sell your “six-figure collection” for pennies while you’re not looking. 😈
⭐ Produced by Icons of Real Estate – iconsofrealestate.com

Ryan & Jarrod are back to unpack cruise ship chaos, pet emergencies, real estate risks, and generational money mindsets. From Franklin’s medical scare to buying another commercial building, the conversation blends humor with unexpected depth.
This episode explores what truly matters, the reality of entrepreneurship, and why sometimes the biggest problems are just high-class inconveniences.
It’s unfiltered, reflective, and classic Two Guys energy.
🎧 Hosted by: Ryan & Jarrod
💡 Key Themes:
✔️ Perspective vs. frustration
✔️ Risk, debt, and financial independence
✔️ Pet ownership and emotional priorities
✔️ Generational retirement differences
✔️ Business ambition vs. peace of mind
📇 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. 🐍

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

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

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