Reflections on Five Years

This week the Jon of All Trades Podcast celebrates five years of being on the air and more than 200 guests. I realize as I write this, that’s longer than I’ve done any one thing professionally. My longest actual job tops out at four years and five months. I wrote Cru Jones Society for just over three years, which, admittedly, felt like it was much longer considering the volume I words I spewed in that time. And I’ve been plugging away at Deft Communications for nearly four.

I’ve been trying to answer the question of whether I thought this thing would last five years, and I suppose I always did. I’ve seriously considered ending it a few times, but have always come back to it. And the thing that keeps me coming back is that I’m endlessly curious about people and every time I do a new interview, I leave it feeling energized.

So, to give you a little peek behind the curtain, here are five interviews from the last five years (one from each year) that mean something to me. These are by no means my favorites (I love them all in different ways), but they each stick out in my mind for something I learned as a result of them.


Year 1: Jason Heller (Ep 16: June 17, 2014)

Jon of All Trades by the numbers

A mere 16 episodes in, and I thought the podcast would blow up as a result of an interview. I loved the work of Jason Heller, who was in the process of wrapping up a long series for the AV Club called “Fear of a Punk Decade” about punk rock in the 1990s. I idolized the AV Club as it was my first stop on the internet at the time, and figured the juice simply from being associated with The Onion would instantaneously translate into massive success and listenership for me.

I learned that things don’t work that way. While that show did well, it was going to be a much longer walk uphill than I had anticipated. More important than that realization was that I learned I had the chops to conduct a long form interview with someone I’d never met. Jason was the first person I’d ever cold pitched for the show, and his agreeing to be on it put me into a state of mild euphoria. I couldn’t believe anyone who’d won a Hugo Award and written for some of my favorite publications would deign to talk to me in my kitchen for an hour.

This was the first time I honestly felt like, for a variety of reasons, I had something here. And although no one asks me much about it now, it’s the first time the show turned a real corner.

Year 2: Nathan Silver and Mike Ott (Ep. 82: November 16, 2015)

Nathan Silver and Mike Ott, independent filmmakers, are the guests on Ep. 82 of the Jon of All Trades Podcast from the Denver Film Festival.
Nathan Silver and Mike Ott, independent filmmakers, are the guests on Ep. 82 of the Jon of All Trades Podcast from the Denver Film Festival.

Out of the blue, I got invited to produce shows at the Denver Film Festival. The Festival’s press guy, Neil Truglio, emailed me, told me he loved my podcast, and wanted to feature attendees on it. I was enormously flattered by this, and tremendously excited. He pitched me a slate of guests, all of which I said yes to including Tarantino favorite Zoe Bell, professional prankster Joey Skaggs, and others whose work I had a good handle on.

Smack in the middle of the five interviews I did sat Nathan Silver and Mike Ott. I received screeners of their films and panicked because I didn’t fucking understand them. I read as much background material on each as I could, and the films somehow made even less sense. I was petrified going into this interview because I was certain I was going to embarrass the shit out of myself and piss off my guests. Their films were challenging, and I figured these guys to be artistes. But they both couldn’t have been nicer or funnier or more engaging, and we had a delightful chat that became one of the interviews I remember most fondly.

Their films are still really fucked up, and I don’t think I get them, but I also kind of like that, too.

Year 3 (tie): Holland Darcy and Suzi Q. Smith (Ep. 101: July 12, 2016 and Ep. 109: October 4, 2016, respectively)

Suzi Q. Smith, slam poet and Executive Director of Slam Poetry, Inc. is the guest on Ep. 109 of the Jon of All Trades Podcast, debuting October 5, 2016.
Suzi Q. Smith, slam poet and Executive Director of Slam Poetry, Inc. is the guest on Ep. 109 of the Jon of All Trades Podcast, debuting October 5, 2016.

This was by far the biggest year of the podcast featuring not only Holland Darcy of Road Rules and MTV’s The Challenge fame, but also Kyle Clark, Jim O’Heir from Parks and Recreation, Lynn Bartels, and nearly all of my most downloaded episodes. For whatever reason, I was on a roll this year content-wise. The show was absolutely crushing, and nothing exemplifies it more than Holland’s episode which is still my most downloaded, by a country mile (which is why I chose my photo with her as the lead photo of this piece). I think I disarmed her by how much I remembered about her seasons, which was just me scratching every itch I’ve ever had about these shows since they meant so much to me during high school and college. I discovered many felt the same way, which is why this is one still so popular.

Suzi Q. Smith I met as a result of an email I sent Bree Davies, another former guest. I asked her to help me broaden my network, which was heavy on white dudes, and she obliged by giving me contact info for a ton of cool people. Suzi Q. Smith was Executive Director of Poetry Slam, Inc. at the time and was so kind in providing a glimpse into a world I knew nothing about, and speaking firsthand about the challenges of growing up in a predominantly white culture. If I can open the world for others by opening my own, I’m doing good work. It also bears mention that I found Suzi to be unassailably cool and an incredible craftswoman at everything she did.

Year 4: Drew Magary (Ep. 139: July 4, 2017)

Drew Magary, columnist for GQ and Deadspin, as well as author of The Hike, is the guest on Ep. 139 of the Jon of All Trades Podcast, debuting July 5, 2017.
Drew Magary, columnist for GQ and Deadspin, as well as author of The Hike, is the guest on Ep. 139 of the Jon of All Trades Podcast, debuting July 5, 2017.

A bucket list interview for me. You mean the guy who writes about poop for that sports blog? The very same!

Another cold pitch that I built around his book tour coming through Denver. I had to coordinate with a publicist from his publishing house on this, but I got it nailed down. Drew has always been an inspiration to me because beneath that juvenile façade is a beautiful beating heart that’s not afraid to express vulnerability or disrobe intellectual imposters. His novels are insanely entertaining, and I always wondered if I’d have the chance to meet him personally.

I went one better and interviewed him for an hour. I had planned to attend his book signing and the drinking that ensues afterward, but in an unbelievable set of coincidences, it was not only my youngest daughter’s first birthday, but also the public hearing for one of my biggest clients’ project that I’d been working on for nearly a year at that point.

Since I was billing by the hour, I went to the public hearing that lasted from 6:00 pm until just after 12:30 am. They were successful in their public hearing, which was good, but served as a cruel reminder that you can have nothing on the calendar for weeks, and then every single thing in your life will occur on the same fucking day. Unbelievable.

Year 5 (tie): Vinnie Fiorello and Joan Rogliano (Ep. 175: May 15, 2018 and Ep. 205: January 29, 2019, respectively)

Joan Rogliano, founder of Wildflower Group and Rogliano Real Estate Group, is the guest on Ep. 205 of the Jon of All Trades Podcast, debuting January 30, 2019.
Joan Rogliano, founder of Wildflower Group and Rogliano Real Estate Group, is the guest on Ep. 205 of the Jon of All Trades Podcast, debuting January 30, 2019.

When I drove out to Grand Junction last year with some friends, I had a “Hey, dumbass!” moment in that I realized I should be pitching Less Than Jake and/or Face to Face for an interview. I mean, why not? I’ve got a legit show, I love both of these bands, and how much media could they possibly be doing in a market the size of Grand Junction anyway? I was nervous as all hell for this interview considering Vinnie’s been answering questions for 25 years and I’m a huge fan. But I’ve also got hours upon hours of interviewing practice under my belt at this point, and I’m a huge fan. And this interview was great. Vinnie ended up telling me about his divorce, his grandfather dying, and all sorts of other personal stuff I don’t think he shares that much. It was affirmation that I’m actually good at what I do.

Joan Rogliano came as a result of her pitching me, which is how many of my guests come about now. It’s always interesting interviewing someone with whom you seem to share little in common. Joan and I come from different generations and have vastly different life experiences, yet we had an illuminating and stimulating chat, as well. I adored my time with her and have been told the subjects we covered have helped some people. It’s only by trying to make new connections that we realize what’s possible.


I’d be lying if I said I’m not disappointed the show isn’t bigger than it is, but I also own the fact that I don’t hustle it the way I probably should. I’ve never enjoyed the art of self-promotion, and its rhythms don’t come naturally to me. I once had a manager tell me that no one is in charge of my career but me, and while that’s true, I’ve always been more of the mindset that if you do good work at a consistent clip, success will find you.

That’s also true (to whatever extent), but places a disproportionate onus on others to find you. Everyone has a lot of choices about how they spend their time, and if you can’t cut through the clutter, it’s no one’s fault but yours if you’re not at the level you wish. It also doesn’t change the fact that talking up my show and selling it to those who wouldn’t already be here makes me feel like I’m wearing burlap underpants.

I’ve counseled many who have sought to start their own podcast, and I’m not shy about sharing the many high hurdles in front of them. One thing I’m fond of saying is that producing regular content is like having a pet monster that eats and never gets full. Feed me, Seymour!

There was a show in 2006 called Studio 60 on the Sunset Strip, starring Matthew Perry and Bradley Whitford as the writers of a late night comedy show a la Saturday Night Live. Looming over nearly every episode is this giant clock that counts down to the next episode’s airtime.

An image I cannot shake from this long-forgotten show’s second episode is its conclusion. Perry and Whitford’s characters have miraculously pulled off their first show together at the helm and crafted a delightfully weird and highly amusing cold open set the tune of “I Am the Very Model of a Major Modern General” from The Pirates of Penzance. A look of warm satisfaction washes over Matthew Perry’s face that quickly melts into dread – a dread that only occurs at a sudden realization. He looks to his right at the clock on the wall that has now rolled over and begun counting down to next week’s show.

He literally gave himself five seconds of happiness recognizing the beauty and basking in the joy of what he’s created before pivoting to the unforgiving reality of the ceaseless march of time and the next mountain he has to climb. Wanna know what it’s like creating new content that occurs on a recurring schedule? That scene is flawless in its appraisal.

So, in the spirit of hopping off this perpetual motion machine for a brief moment, I offer this humble blog post. I don’t get much time to reflect these days, and while I toyed with a number of ideas for how to celebrate five years on the air, I opted for the low-key.

Because, in all honesty, despite how much effort goes into making this show happen week after week after week for five years, and no matter how many times I’ve seriously considered quitting it altogether, Jon of All Trades represents pure joy to me. The fact that I get to do it at all overwhelms me. I get to sit down with people I find interesting and ask them virtually anything I want for an hour, and then share it with you. I’ve turned an abstract dream into a reality. Can you say that about whatever it is that you do? I sincerely hope that you can. And if you can’t, what’s stopping you?

I don’t know what comes next. No one does. Tomorrow is promised to no one. I know that I’ll have a show for you next week. And the week after that, and the week after that, and so on, but for how long? I honestly have no idea, but I do know that at some point this ride will end, and when I look back honestly, I’ll be satisfied because I created something that matters, something that I love, and something that’s pretty much exactly what I wanted it to be.

And I couldn’t have done it without you. So, whoever you are – whether you’ve listened to every show I’ve ever done or are just now finding me via this blog post for the very first time – thank you for letting me be a part of your life. I’m overwhelmed by the privilege, and for how ever long this ride continues, I owe you an immense debt of gratitude.

Say goodnight, Gracie.

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