Top 5 Things I’ve Learned from Doing This Show for 7 Years

Welcome to Top 5 Fun Friday, a regularly-occurring blog feature where I give you a list of extremely specific pointless shit from my life no one asked for. Why? Because the internet is STILL incredibly un-fun in 2021 and I enjoy blogging. It’s Friday and these will be fun! This week’s list…

Top 5 Things I’ve Learned from Doing This Show for 7 Years


A year and a week ago I landed in Arizona to visit my mother-in-law, and have some fun with my daughters in the sun. For the previous two or so months I had heard about the burgeoning health crisis in China due to some as-yet-unnamed virus. I brushed it off the same way I brushed off SARS, West Nile, Mad Cow, Foot & Mouth, Swine Flu (which was the big thing right around my wedding), and every other scary, novel disease out there that never seemed to molest the United States in the same way it did other countries.

We ate dinner in a great brewpub near my mother-in-law’s house in Northwest Phoenix, and watched in astonishment as Rudy Gobert of the Utah Jazz tested positive for coronavirus (just days after being a smug dickhead and mocking the virus by touching all the mics) and the NBA shut down. That was the first domino to fall. Others followed, and swiftly. The rec centers in my mother-in-law’s community shut down. Major League Baseball cancelled Spring Training. And it rained. The rain poured down endlessly, which meant we were stuck in a small house with two antsy young kids and nowhere to now take them with the added bonus of feeling absolute dread at the prospect of getting back on a plane in a few days.

Once we got home, I sent out a notice announcing the suspension of my show that lasted all of 11 days because I realized very quickly that a) my little slice of the internet could give people hope, amusement or diversion when it was so desperately needed, and b) we were all stuck at home, so everyone was suddenly available and willing to talk to me! In terms of the show, this virus has been tremendous! One other thing became clear immediately, and that segues perfectly into this week’s post.

I have learned a lot about myself, my show, podcasting in general, and promotions in the last 7 years. Here are my five biggest takeaways:

I cannot quit this show.

How many times have I tried? A dozen? Maybe more? Something always pulls me back to it, and as soon as I do another interview, I’m full of energy, vitality and joy. I love talking to people in this format, and I probably always will. So here we are: Seven fucking years of doing this. Unreal. I literally haven’t done anything creatively or professionally for this long, and this show has infected every corner of my brain.

Jason, Kristin and I were in a Lyft once on our way to a beer festival (oh, how I miss those) and our driver was a flight attendant who drove Lyft on her off-times. I started asking her all these questions about being a flight attendant, and before you ask, yes, I am the type of Lyft passenger I didn’t want to have when I was a Lyft driver briefly two years ago. But I learned a bunch of cool shit about being a flight attendant (My favorite line: “I’m not your fucking waitress, I’m there to get your ass out of the plane if it crashes. We just serve food and drinks because otherwise we’re bored.”). When we got out, Jason said mockingly to me, “Oh look, Jon of All Trades always on the job! [a pause] No, but seriously, that was an awesome conversation.”

I can’t not ask people about themselves. I am endlessly curious about people and I like gaining insight into what makes them tick. I’ve built a platform that allows me to do that and for everyone else to enjoy it to whatever extent they want to, too. I have no idea how long this show will go on, but I know that I suspect it will always exist in some form or fashion. It may not look like this forever, but throwing away a reputation built on curiosity, a desire to deepen our empathy, and a strengthening of our human bonds would be foolish. I’m likely here for the long haul.

I really and truly do not give a fuck about being famous

You’re likely calling bullshit already, but here’s the thing: If fame were my primary personal motivator, it seems reasonable that I would have used this show as a launching point for something else, doesn’t it? I’ve been in the Denver Business Journal, I’ve been in the Denver Post, I was featured in a series of posts from 9News because of my interview with Kyle Clark. I’ve gotten a small amount of notoriety from this show, and while it is cool, it’s ultimately fleeting.

Chasing fame for its own sake is gross. People who want to be recognized and well-known for those reasons unto themselves are not only fucked in the head, they’re setting themselves up for massive disappointment, particularly in the high speed blender of disposable pop culture in 2021. Here today, gone later today is the modus operandi for a culture so inundated with choices, fame is as ethereal as the buzz of a hastily smoked cigarette between work meetings.  

To me, fame is a byproduct. Do good work, success and notoriety will find you. Over these last seven years, I have put out a high quality product consistently that says many things about me. I’m dedicated. I’m off-kilter. I persevere. I have a broad range of interests. And I love people. People have awesome fucking stories that they very rarely get to tell because we’re all just waiting to talk instead of listening. On this show, I listen. And it’s in listening that I’ve found beauty in humanity that I otherwise might not have.

Also noteworthy: Autonomy is far preferable to fame. By virtue of doing this show successfully, I now get the opportunity to produce shows for people and organizations I like and admire. I introduce myself to people doing estimable work and earn their trust because I genuinely care about them and want to hear their stories. I set my own schedule, do work that I enjoy, and chase business I care about. No one tells me how to run my own railroad, it’s all up to me. That’s freedom, and I’ll take it over fame 100 times out of 100.

The difference between technical skills of a podcast producer and a professional sound designer is LARGE

For as technically competent as I am at the production of my own and others’ shows, I am an embarrassing and rank amateur in terms of overall sound design. Recording, editing, and optimizing a conversation with a handful of music cues is something virtually anyone could do with a modicum of training. It’s really not that hard.

And what’s funny is that when I consult officially or unofficially on the development of a new show (I’ve done this about 15 times, at least), everyone comes in thinking they’re going to want to talk about the technical side of producing. I give them the tips they need and recommend some equipment and software, but what I ask them are the harder questions: What do you want people to think, do or feel after having listened to this show? Once you’ve answered that, then you’ve got a whole slew of creative decisions to make that should ultimately be in service of whatever that goal (or goals) is (are). And that’s where I excel, as I believe the role of a good producer is to help the best version of whatever product someone wants to create emerge. I’m a guide.

If you need someone who can mix, layer, and create complex soundscapes, that likely ain’t me. You should call Mike Henderson, who reminds me of Bruce Springsteen in the way he presents as a humble, understated craftsman that disguises his genius level of talent and uncanny instincts that make everything he touches better.

I’m a great interviewer and a shitty promoter

The recently departed Larry King is probably one of the most notable interviewers of all-time. And he famously barely prepped for any of his interviews. The twofold reason is that he a) didn’t want to make his guests uncomfortable so they’d both come back AND tell their friends about the experience, and b) he wanted to serve as the direct audience surrogate and learn about the guest along with his audience. It worked, because the man’s track record is unparalleled.

The critique of this approach is that it makes almost every interview sound exactly the same and precludes discussions of any real depth. My approach depends on the guest. If it’s someone who isn’t used to being interviewed, I take a softer approach and spend a great deal of time making them feel at ease before you ask them about whatever pertinent issues of controversy I want to cover. I’ve done more interviews of this type than any other.

If it’s someone who has been interviewed a lot, then I do a shitload of prep. I do my damnedest to ensure my guests aren’t bored or resentful of me when I finish. I try to make my interview at least a little bit different from the bounty of other interviews they’ve done, and I usually succeed. My reputation is built on this, and it’s a good one. I’d put my interviews up against just about anyone this side of Howard Stern.

On the other hand, my promotional skills are dog ass terrible. You want the real reason this show isn’t bigger than it is? It’s because I’m fucking terrible at hustling it. The rhythms of self-promotion do not come naturally to me, and I loathe just about every second I have to do it. The only thing – literally THE ONLY THING – that makes me do it at all is because I feel like I owe it to my guests.

I remember in corporate I got the advice that no one is responsible for the advancement of your own career except for you. That’s 100% true, and can be applied to the growth of a show. Part of me believes that the cream always rises and if you put in hard work, success will find you (as I said above). The realistic part of me knows that’s horseshit simply because the volume of noise you compete against is in many ways insurmountable without a sustained and intentional effort.

But I just don’t want to. At some point I’m going to have to bite the bullet and pay someone to do this for me. This realization makes me unhappy.

More people are willing to say yes than you think

When I was like 14, my dad used to tell me that girls were waiting for me to ask them out. He obviously didn’t mean that girls everywhere were just sitting at home staring longingly at their yearbooks at my photo waiting for me specifically to ask them out, but that everyone likes to be invited to go on a date. I didn’t believe him at the time, and social anxiety precluded me from doing as much asking as I might have liked.

I had a handful of girlfriends until I was 17 when I moved to Houston, so obviously my social anxiety wasn’t totally crippling. But Houston was where I turned a real corner. I found myself at a New Year’s Eve party with my friend Ryan, his girlfriend, and a bunch of band geeks. Ryan and his girlfriend were literally the only people I knew at this party, and there was one girl there named Lucy who I was extremely attracted to. I wanted to ask her out, but thought twice about it. Then I thought three times, and here’s what popped in my brain, “Dude, you’ll never see any of these dorks again. Just ask her. Remember what your dad said, and if she says no, then fuck it. It’s a huge high school, and you’ll never have to worry about it again.”

So I found myself a moment when I was alone with her, and I said, “Hey, Lucy!” She said, “Hey, what?” And like a blunt force instrument, I went with this, “Can I have your phone number so I can ask you out sometime?” She didn’t even pause and said, “Sure. Let me grab a pen.” Dude! A) My dad was right! and B) Holy shit, that actually worked! I called her a few days later and we went to Chili’s and then saw Varsity Blues in the theater. That changed the trajectory of my life from that point forward.

Cold pitching is a big part of my actual moneymaking job. I have to email and – this is pure nightmare fuel for Gen Z, I’m sure – call people I’ve never met before for a variety of reasons. I’m good at it in the same way anyone is good at any aspect of their job after doing it a zillion times. The way that translates to the podcast is that I’m fearless when I pitch potential guests. My very first successful cold pitch was to Jason Heller, which was Episode 16 of the show, almost seven years ago. Damn near all of my most notable guests from Kyle Clark to Ryan Spilborghs to Chris DeMakes have been cold pitches.

Since it’s the 7-year anniversary, here are a handful of cold pitches that didn’t work out for one reason or another. I was damn close to interviewing Governor (now Senator) Hickenlooper in 2018, but seeing as he was gearing up for a laughably terrible presidential run (that I suspected, but was unconfirmed at the time), his staff shot me down. Right around the same time, through Denver Film Fest I had filmmaker Jason Reitman lined up, but his people pulled the plug at the very, very last minute. That one stung. Early on in the show’s run, I reached out to Colt Cabana who was appearing with Lucha Libre & Laughs, but his schedule was too tight for him to appear, and he sent me a very nice note thanking me for reaching out. I reached out to all the guys on All Fantasy Everything when they were here for High Plains Comedy Fest, but none of them bothered to acknowledge my existence.

Sometimes they don’t work out, but more often than not, they do! Be fearless in your requests, and for the love of god, whatever you want to do, give someone the opportunity to say yes. You’ll never know until you ask the question, and if you don’t, the not knowing will nag at you forever. I’m grateful I’ve taken the chance on this show and that you’ve been there with me. Thank you for taking the journey with me.

Say goodnight for now, Gracie.

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