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.

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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!

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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.

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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.

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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.

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Ep. 21- Zack Robb aka Stache Squatch

In this episode Derek talks with Lone Wolf Custom Gear team member, Zack Robb. Zach is from central Virginia and has transitioned from somewhat agricultural hunting land to more rigorous mountain terrain. This challenging terrain has really inspired Zack to push himself and learn to hunt mountain bucks. 

Zack starts with a story about the first buck he was able to observe bump from a bed, then make a game plan to gain intel on the buck, and eventually set up to kill the buck. Zack used a few different tactics including knowledge of buck bedding tendencies, mock scrape intel with a trail cam, and a bump and dump after heading in to hunt the buck bed but jumping a doe group on his way in. 

We transition the conversation into hunting the rugged mountain terrain and how he went about scouting a somewhat monotonous terrain to locate and hunt a giant old 8 point. Zack talks about the importance of locating historical and signpost rubs, pushing into the cover when you know pressure is mounting on the edges, and the power of the first time sit. 

We cover many different small learning moments in this episode and finish out with one that got away that intertwines Zack’s rub stories with a giant old 10 point that ended up getting shot by a fellow mountain hunter over 4 miles away. 

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AI is creeping into every corner of the hunting world, but is it helping hunters, or just making us lazier? Greg, Eric and a handful of callers debate the rise of AI-powered trail cams, smart optics, and hunting apps that predict deer movement with machine learning.

Is technology making us better hunters, or just over-reliant on gadgets? Meanwhile, good ol’ woodsmanship—reading sign, knowing terrain, and putting boots on the ground—is becoming a lost art.

Our listeners chime in with their takes on e-bikes, electric bow sights, and the ethics of using drones for game recovery. This episode dives deep into where hunting is headed, whether we like it or not.

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In this episode, Derek sits down to talk with Alvin. Sitkiewicz of Michigan Gone Wild.  Michigan Gone Wild is celebrating their 10th year of production of awesome YouTube deer Camp videos.  Alvin and his group of friends have been filming from lower Michigan Archery and gun hunting along with out-of-state Whitetail hunts all across the country.

In this episode, Alvin and Derek talk about versatility and learning from every situation in the woods. They discussed hunting different terrains and styles and how getting competent in each helps you as a well-rounded Whitetail hunter.

Alvin talks about how hunters see the woods differently and how small details can make the biggest difference. Stories are told and tactics are discussed as we dive into chasing mature deer with both archery tackle and firearms.  Alvin is a true student of deer and has done an amazing job at amassing a wealth of knowledge that he can call upon while dissecting the Deer Woods. He does a great job bringing that information to our listeners today. Enjoy!

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This episode dives into the unique personalities and perspectives from across the Okayest Podcast Network, showcasing how there’s truly a podcast for anyone and everyone in the outdoors. From public land etiquette and gear tips to the challenges of late-season hunting and even trapping insights, the hosts share their expertise, humor, and stories. Whether you’re here for practical advice, entertaining banter, or just a deeper connection to the outdoor lifestyle, this episode—and the broader Okayest Podcast Network—has you covered.

https://www.okayesthunter.com/pages/okayest-podcast-network

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Derek sits down to talk to Justin Synan from lone Wolf Whitetail Addictions and host of Run & Gun podcast. Derek and Justin talk about his upbringing of hunting public land and suburban areas of Maryland in his youth. Later in life, Justin and his family decided to move to Kentucky to pursue trophy whitetails having lived in Kentucky the last five years they discuss how he’s been able to gain permission and hunt some trophy class deer in different properties around the area he lives. 

Even though you live in areas with large mature bucks, it doesn’t always mean things are going to go your way. This season has been riddled with pitfalls and dead ends as Justin tried to track down one of the many bucks he had scouted before season began. This episode is an entire story about Justin season, the ups and downs, the hardships, and the successes that come with a long grinding season.

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