Guiding with Cliff Gray

Doug Duren joins the show and discusses the Sharing the Land initiative, explaining how it connects landowners and conservationists through habitat restoration, wildlife management, and community engagement. He outlines practical approaches to managing chronic wasting disease (CWD) in Wisconsin, navigating policy controversies, and offering solutions like replacement deer tags to encourage responsible hunting. Throughout the episode, Doug emphasizes hunters' and landowners' shared responsibility in preserving natural resources, stressing the importance of collaboration and informed participation to ensure the health of wildlife and habitats for future generations. Learn more about your ad choices. Visit megaphone.fm/adchoices

Michael Perry is a Wisconsin-born author, volunteer firefighter, and former nurse who's spent his life mastering the art of storytelling, often about his own hilarious misadventures. Which is a prerequisite for being a guest on our podcast! We dive into deer hunting as a New Year’s ritual, being an outsider in hunting culture, and what it's like hauling a buck out in a rebuilt 1951 International pickup. Michael might've been the only Wyoming cowboy putting himself through nursing school. It's a reminder that the best hunting stories aren't always about deer but the perfectly okay people behind them. Presented by: https://www.nosler.com/ Learn more about your ad choices. Visit megaphone.fm/adchoices

Cliff Gray lives the kind of life that makes most outdoorsmen envious, splitting his time between guiding hunters in the mountains and spearfishing in the waters of Puerto Rico. From the reality of selling his outfitting business and navigating the unpredictability of guiding to the obsession of spearfishing and the logistics of making a life in the Caribbean, this episode dives into the balance of adventure and practicality. Along the way, the guys cover the wild nature of spring bear hunts, the unique challenges of mountain lion hunting with hounds, and the realities of outfitting, both as a business and a lifestyle. Cliff shares stories of lost hunters, backcountry mishaps, and the surprising things you learn about people when the wilderness gets tough. Plus, a deep dive into what makes a great guide (hint: it’s not just being a good hunter). If you’ve ever thought about dropping it all for a life in the mountains or chasing adventure on your own terms, this conversation is one you don’t want to miss. Presented by: https://www.nosler.com/ https://pursuitwithcliff.com/ Learn more about your ad choices. Visit megaphone.fm/adchoices

Skyler Bradley joins the Okayest Hunter podcast for a conversation that’s equal parts hilarious and wildly relatable. From viral TikTok deer skits to the unpredictability of internet fame, Skyler breaks down how a simple idea, born from a tradesman’s workday gripes and turned into a massive social media following. It’s not just about dressing up in a deer costume and dodging imaginary arrows; Skyler has a knack for capturing the absurdity of deer hunting, tradesmen banter, and just about anything that makes hunters laugh at themselves. The conversation jumps from his process of making content in between work and hunting, to the wildest hate messages he’s received (some people take fake deer content way too seriously), to why he’s convinced his videos belong in every deer camp. There’s also plenty of scheming. From live TikToks in costume, dream collaborations, and ways to rope big-name hunters into his skits. If you’ve ever found yourself cursing a squirrel from a treestand or wondering how the hell a deer just vanished, Skyler’s content and this episode is for you. Check out the other shows on the Okayest Podcast Network: https://www.okayesthunter.com/pages/okayest-podcast-network Learn more about your ad choices. Visit megaphone.fm/adchoices

Mark Kenyon joins the show for a deep dive into conservation, public lands, and the growing threats to access and wildlife management. He eloquently explains how conservation should be a nonpartisan issue, yet political and economic pressures put some of the country’s most treasured outdoor spaces at risk. Mark shares insights from That Wild Country and his recent work, highlighting the resurgence of land transfer efforts, resource extraction priorities, and the role hunters and anglers must play in protecting these places. This episode isn’t just about identifying the problems. We also talk about actionable solutions. Mark explains how grassroots efforts, public pressure, and strategic advocacy have successfully defended public lands in the past and why it’s time for the hunting community to engage again. Whether you’re an avid public land hunter or just someone who values having wild spaces to roam, this conversation will get you thinking about how to take action before it's too late. Learn more about your ad choices. Visit megaphone.fm/adchoices

The fellas dive into the ever-elusive mastery of deer hunting this week. Things like how experience builds in layers and how you don’t even hear the right lessons until you’ve suffered through enough mistakes to be ready for them. Buck beds, trail cam traps, wind shifts—every misstep is a lesson, whether you learn it the hard way or just listen to someone else’s. They get into the nuances of public vs. private land hunting, how assumptions are the fast track to failure, and why seasoned bucks move at the speed of continental drift when they know they’re being hunted. If you think you’ve got it all figured out, the deer woods will humble you fast. Between scouting talk, plans for Okayest Hunter's annual Foam Fest, and the never-ending pursuit of doing better without drowning in ego, there’s plenty to chew on. The biggest takeaway? No matter how much you learn, there's always another painful lesson waiting for you next hunting season. Learn more about your ad choices. Visit megaphone.fm/adchoices

Exploring Iowa’s Public Land: Big Rubs, Shed Hunting, and Scouting for Future Hunts In this episode of Dropping Pins, Derek embarks on his first-ever public land scouting trip in Iowa. With a possible tag draw in two years, he’s putting boots on the ground, marking stand locations, and soaking in everything the terrain has to offer. From massive rubs and historical scrapes to ideal bedding areas and overlooked hotspots, Derek covers miles of ground, uncovering prime whitetail sign along the way. The trek isn’t just about finding sheds (though he does walk away with two fresh ones). It’s about understanding how mature bucks use the land—where they bed, travel, and stage before heading to food sources. As he marks key locations on Spartan Forge, Derek shares his thought process on how to approach hunting these spots in the future. Whether you're gearing up for your own out-of-state hunt or just love the thrill of scouting new ground, this episode is packed with takeaways that will help you dial in your whitetail strategy. 🎧 Tune in to hear about Derek’s Iowa adventure, the biggest scrapes he’s ever seen, and why hill country scouting is both brutal and rewarding! Learn more about your ad choices. Visit megaphone.fm/adchoices

Ryan Lonergan steps into the Okayest Hunter studio and right away, it’s clear, this one’s gonna be a good time. He’s the host of the Fragout Podcast, a veteran advocate with 18 years of service work under his belt, and a guy who’s seen more than a few hard truths. The conversation swerves from the absurdity of podcasting tech failures to the real-deal struggles veterans face when transitioning out of the military. Everything from bureaucratic nightmares to the unspoken reality of ego getting in the way. But it’s not all doom and paperwork. Ryan’s deep in the veteran hunting community, talking up organizations like Ultimate Veteran Adventures, House in the Woods, and the Horicon Veteran Duck Hunt—places where the outdoors isn’t just about the pursuit of game but about reclaiming a sense of purpose. The woods, after all, don’t care what rank you held or what battles you fought; they just demand your presence. The discussion takes a few detours into the camaraderie of deer camp, the mystique of early morning duck blinds, and the absurdity of barbecuing competitions where the wrong rib texture can get you judged harder than a missed shot at 20 yards. Plus, there’s the saga of "Crisco"—a nickname Ryan never asked for but can’t seem to shake. Between the sarcasm, war stories, and serious talk about how the veteran community mirrors the hunting community (for better and worse), this one’s a deep cut—funny, raw, and unfiltered. If you want a masterclass in resilience, a crash course in why the VA home loan is an underused goldmine, or just to hear a guy who’s been through hell and come back laughing, this one’s for you. Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode of Dropping Pins Derek talks to central Wisconsin native Brian Dombrowski. Brian has been a serious big buck killer for a long time and spends a considerable amount of time scouting and learning the public lands of WI, as well as a few other states. Brian has killed and hunted some truly remarkable animals in different states.  We dive right into some great scouting conversations and how Brian has been logging time in this post season period to locate some familiar bucks he has been after. We discuss an area where Brian has been consistently getting on some of the biggest antlered bucks his area has to offer. We talk about what types of habitat the mature bucks like to use and what time of year they are using it.  Brian dives into an epic story that has been unfolding for the past 4 years, with multiple encounters with a true giant marsh buck. We dive into details of his setups, and how bucks used the terrain and wind to their advantage.  Brian may have found his ghost buck yet again this post season after locating some tal rubs that had this bucks signature all over them.  Overall, Brian sheds light on his scouting practices and what has helped him located and hunt some of the most mature bucks on the public lands he hunts.  Surely, Brian will be a guest that we speak to again. Learn more about your ad choices. Visit megaphone.fm/adchoices

This episode was chaos—just like every hunting season. Bourbon-fueled ramblings, shed hunting plans, and the occasional existential crisis about the meaning of a three-finger pour. But beneath the laughter and whiskey-soaked musings, there's gold: Iowa scouting, antler obsession, and the never-ending pursuit of finding the right place at the right time. Derek recounts his solo mission into Iowa’s bluff country, covering 15 miles of rugged terrain in search of sheds, encountering fresh rubs, a dead buck, and one wise old owl keeping watch. The lesson? When you find one shed, there are likely more. And if your hips hurt afterward, you probably did it right. Meanwhile, predator activity is ramping up, coyotes are stealing sheds, and somewhere, a turkey hunter is arguing about whether turkeys belong in the upland bird category. There’s also a sidebar on Kwik Trip snacks, the endless Big Buddy drink, and why a Kwik Trip cheeseburger might be the only thing keeping Midwesterners going through the late-season slump. To top it all off, Taylor Swift makes an appearance—metaphorically, at least—because whether it’s antlers or bourbon, sometimes you just gotta shake it off. Learn more about your ad choices. Visit megaphone.fm/adchoices