One of my scariest moments from high school was learning that one of my sisters had stumbled into my cigar stash in my underwear drawer. I'm only just now wondering WHAT the heck she was doing digging through my underwear drawer in the first place but, anyway… I had to quickly come up with some story about how it was my friend's and i was keeping it for him because his parents would kill him if they had found them or something like that…she totally bought it and I narrowly avoided my parent's wrath. I can't tell you how grateful I am to be able to laugh at that whole situation now, AND that I don't have to hide my love for a good cigar anymore! What i've found the more I've gotten into smoking cigars lately, is that this rabbit hole is DEEP: like most things, there's so much more than meets the eye.

This episode, I invited my friends JD Tiner and Brett Taylor to come over for a smoke while they entertain my curiosity about things cigars. Just a heads up- we were sitting outside on my back house porch and the rain was INTENSE, so if you're wondering who left the sleep machine on, it was God.

My guest today is one of my favorite people in the world. Equally hilarious, smart, and vulnerable, Barrett Ward is a really unique guy. If that name sounds familiar, then you might be a member of the Mocha Club, or maybe you own a FashionABLE- brand scarf. Barrett is the man behind them both. Barrett is a real visionary who's used his talents to care for and empower marginalized women all over the world, including the ones in our back yard in Nashville. I sat down with Barrett to catch up on life and see what he's working on now.

Earlier this year, I spent a month in Portland, Oregon. I've always loved my brief stops through there on tour, but never felt like I had enough time to, well, let's be honest EAT. Portland has some AMAZING food, but what I DIDN'T know is that they also have some amazing, wait for it… PINBALL. Yep. Pinball- the game with the flippers and the silver ball. I LOVED pinball growing up and so now, anytime I find a working pinball machine, I have to drop a couple of quarters in and play. What I DIDN'T know is just how deep this pinball thing goes. I began to get curious about all things pinball upon returning home to Nashville, and ended up meeting Seth Steele, cofounder of the Nashville Pinball League, and owner of some 20-odd pinball machines. I thought he'd be the perfect person to offer a window into the obsession that is PINBALL.

I had been hearing about this ex shoe designer for Nike, who coincidentally also designed the first powerbook for Apple and now living in Nashville for a couple years before we were formally introduced. Because I had gone to college essentially to learn how to design sneakers, but then fell in love with Apple (among other great design-centric brands), I was all-too-eager to meet Gavin Ivester. At our first lunch meeting, we ended up dialoging for a couple hours on all things design and style and process, the whole time, wishing I had brought my tape recorder. Fortunately, I WAS able to record our SECOND conversation, so without further adieu, here's a couple guys nerding out about design.

In the late 90's, if you were a Christian high school or college kid who was somewhat self aware and into music, you were probably a fan of a band called Caedmon's Call. They were a grassroots folk-rock band out of Houston, Texas that for around 10 years was THE BAND to be into in my little community. My guest today is Derek Webb- one of the primary writers/front men of that band. He would later go on to foster a feather-ruffling solo career, as well as found the tribe-building platform, Noisetrade. Derek's a fascinating guy, and I hope you enjoy our conversation, which you'll be joining mid-stream…

What if your back pain isn't really anything actually wrong with your BACK? And what if your anxiety is really a 'warning light' signaling that something else needs attention? That's what my childhood best friend Dr. Matt McClanahan is finding as he's worked with his patients as well as his own pain. In my opinion, Matt practices the best kind of medicine- taking into account the body, mind, and sprit of the people coming through his doors. There's more to our health than meets the eye, and hopefully this conversation will forever change the way you think about and address what ails you.

This week on The Curiosity Habit, I'm pleased to be sharing my conversation with friend and fellow-curious person, Taylor Bruce. Taylor is one of a handful of friends who shares my same enthusiasm and interest for people and travel, only he's turned his into a business. In 2012, after suffering from writers block while penning a novel, he turned his love for travel, exploration and words into the first of what would become a series of beautiful and helpful field guides with a funny name. Just a heads up- we did this interview outside his way-too-cool adobe office building in Austin, Texas- not far from the airport, so there's some extra background noise in this one! Hope you dig it!

This week's guest is one of those people insecure guys like me can't stand. Not only is Judah Akers building an incredible music career in his band, Judah & The Lion, but before that, he was a star collegiate ATHLETE, playing baseball for the Belmont Bruins. If that weren't enough to make you hate the guy, he's really handsome AND genuinely kind too.

I sat down with Judah in front of a small audience in Nashville at the sneaker and streetwear shop, ROOTED to talk about his journey and how he's coping with the growing pains of being in a burgeoning folk hop & roll band. I hope you enjoy this week's conversation with Judah & The Lion's Judah Akers.

This week I'm visiting with story-telling digital activist & defender of whats GOOD, Branden Harvey. After growing disillusioned by his (successful) freelance photography career, Branden began using photography to tell stories; bringing to light the GOOD in people and the world through Instagram. This subtle shift in the motivating 'why?' has given birth to more opportunities than Branden could have ever imagined, documenting the poorest of the poor in Rwanda to Pope Francis's first official US visit- Branden's mission is to expose the hope and dignity present in the world through his subjects and their stories. I wanted to sit down with Branden to find out what makes him tick as well as hear what he's dreaming up next.

Over the past 10 years, Ben Rector has been artfully carving out a career as a performing singer-sonwriter, amassing hundreds of thousands of fans all over the world, all while staying true to his 'guy next door' demeanor. Ben has been a friend since he moved to Nashville in 2009, and I have been impressed and, lets be honest, JEALOUS by how dang consistent Ben is-both in the quality and craft of his songs, but also how he runs his business.