Two Guys, Two Questions

What happens when you mix 30 years of friendship, a serial entrepreneur, a top-tier real estate agent, and two unprepared questions? In this inaugural episode of Two Guys, Two Questions, Ryan and Jarrod explore everything from the realities of turning your hobbies into businesses to a deep philosophical debate about what comes next in life when you're pushing 50. The guys kick things off by in...

What happens when you mix an impromptu beach trip, an Ozempic overdose story, and a swooping bat in a dark shed? In this unfiltered episode of Two Guys, Two Questions, Ryan and Jarrod explore everything from the harsh realities of cross-country box truck rentals to a deep philosophical debate about free will. The guys kick things off with their chaotic weekly updates—Jarrod is stressing over an en...

What happens when you mix a tropical patio remodel, an escaped snake, and a wildly unproductive day? In this unfiltered episode, Ryan and Jarrod explore everything from the realities of taking Ozempic to a philosophical debate on the one question that would destroy society. The guys kick things off by comparing their weeks—Ryan is building a backyard oasis and closing massive real estate deals, wh...

What happens when you mix backyard wildlife defenses with massive real estate ambitions? In this unfiltered episode of Two Guys, Two Questions, Ryan and Jarrod explore everything from the realities of taking Ozempic to the dream of buying a multi-million square foot underground cave. The guys kick things off by sharing a dangerous but effective hack for keeping raccoons out of the garden. Jarrod t...

In this wildly unfiltered episode of Two Guys, Two Questions, Ryan and Jarrod explore everything from the physical realities of aging to the existential dread of leaving no digital footprint. Jarrod shares the unbelievable, tragic, and fascinating saga of Lee the Collector—an eccentric old man who left behind a 40-year hoard of treasures that ultimately became the world's largest mystery box....

Some stories are just too embarrassing to keep to yourself. In this wildly unfiltered episode of Two Guys, Two Questions, Ryan and Jarrod share some of their most mortifying personal stories. Jarrod kicks things off by explaining why a strawberry milkshake and a copperhead snake led to an emergency roadside bathroom break. Ryan counters with a story about a property appraisal gone horribly wrong,...

In this episode of Two Guys, Two Questions, Ryan and Jarrod bring another hilarious mix of wild adventures and deep debates. Jarrod kicks things off with a terrifying (and pantless) midnight wrestling match with an escaped 13-foot snake, while Ryan shares his mind-blowing experience visiting the Sphere in Las Vegas. The guys then tackle a major "Would You Rather" style question: Would yo...

In this episode of Two Guys, Two Questions, Ryan and Jarrod bring the perfect mix of chaos and deep conversation. Jarrod kicks things off with a hilariously disappointing review of a Star Wars-themed burlesque show in Vegas, his brilliant prank involving Amazon deliveries, and the terrifying story of getting struck directly in the eye by a 7-foot King Rat snake. The guys then tackle a ridiculous "...

In this episode of Two Guys, Two Questions , Ryan and Jarrod take a deeply personal detour. Jarrod returns to his late uncle's property, untouched since 2007, discovering everything from the eerie stillness of an abandoned home to a perfectly preserved, 20-year-old pot plant hanging in the rafters. The conversation takes an introspective turn as the guys unpack Ryan’s "beach house dream&q...

In this episode of Two Guys, Two Questions, Jarrod and Ryan dive into a wild week in rural Kentucky. Jarrod recounts a surreal and eerie visit to his late uncle's abandoned property—untouched since 2007—while battling a serious tick invasion after a day of hunting for snakes. The guys also discuss the merits of buying a side-by-side versus an ATV, the unexpected news of Jarrod's son planni...

In this episode of Two Guys, Two Questions , Ryan and his co-host recount an incredibly eventful week centered around the Lexington Comic-Con. They share the behind-the-scenes chaos and successes of running a massive convention, including getting yelled at (or successfully avoiding it), elevator breakdowns, and dealing with a rogue attendee in a cat suit putting "For Rectal Use Only" sti...

In this guest-free episode of Two Guys, Two Questions , Ryan and Jarrod hold nothing back. Jarrod is gearing up for the massive Lexington Comic Con, while Ryan shares his experience using a crazy new AI audio recorder that maps out entire conferences. The guys discuss the wild west of the early internet before tackling this week's big questions. Ryan shares his dream list of Comic Con guests,...

In this episode of Two Guys, Two Questions , Jarrod and Ryan hold nothing back. Jarrod shares the hilarious reality of receiving massive shipments of frozen rodents and why his FedEx guy thinks he has a severe rat problem. He also shares a story about a botched late-night "aerial burial" for a dead snake while his neighbor watched. They discuss the absolute nightmare of neighborhood grou...

In this episode of Two Guys, Two Questions , Ryan and Jarrod hold nothing back. Jarrod shares the results of his recent doctor’s visit which leads into a highly candid and hilarious recap of his first-ever trip to the urologist for a vasectomy consult. Ryan chimes in with his own vasectomy experience from 20 years ago, proving it's not as scary as it sounds. The guys also dive into a wide mix...

In this episode of Two Guys, Two Questions, Jarrod and Ryan are on a mission to survive with no DoorDash, debate prepping for the apocalypse, and discuss what they’d do with 30,000 comic books (probably not what you think). From random food survival hacks to the band lineup for an upcoming event, this episode is all over the place—just how we like it. 😂 Not to mention, we dive deep into the Andy...

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,...

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’...

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...

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...

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....

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 ongoi...

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...

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 rept...

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 consc...

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 enlig...