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Interview – It’s Date Night with Roscoe Myrick, Entrepreneur and Podcaster

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Today’s guest is a very intelligent, generous, and thought-provoking young man. Roscoe Myrick is the host of the podcast Date Night.

Roscoe invites his guests, total strangers, into his home and interviews them about their lives, their beliefs, and their dreams. The show highlights the magic in the people around us and explores life itself. At first, the show is so different it’s true potential can be lost on the new listener, but the magic comes in finishing the second episode, where it clicks, where you realise this is not another superficial show wanting to be successful, but that this show is deep.

His guests are not celebrities, many of them at the start of their careers, nor are they highly successful entrepreneurs, but that doesn’t mean they don’t have anything to bring to the conversation. And that is the magic of the show, showing us that the people we pass everyday have just as much to offer to the conversation about love, life, and purpose.

He, like myself and my readers, is on a journey to find his place in this world, and it’s leading him away from the traditional career path most people follow. He’s going out there on his own, doing it for the art. I think his intelligence and perspective on life are going to take him far.

He’s one of us, so let’s dive into the interview.


KG – Hey, Roscoe, thanks for taking the time to speak to me. I think we’re both at very similar points in our podcasting / Internet lives, so I think this is a great time for this conversation.
We both seem to be trying something different with our podcasts – I’m producing a horror podcast – but I wondered if you could take us through what you’re trying to achieve through your podcast, Date Night .

RM – I feel like dating gets a bad rap. The negative feelings about dating are often skewed by all of the colossal failures one experiences during the process. It’s my opinion these “bad dates” are just important as the “good dates”. Bad dates tell you more about what you are looking for and who you connect with than simply average ones. People are quick to judge, quick to dismiss a person for a comment, misstep, or preference. Even though, everyone knows how difficult it is to be “on” all the time. Someone you’ve just met doesn’t have the benefit of context. Everything you do or say is the entirety of who you are to them.

Yikes!

I suspect we do have the capacity to understand and give false steps, or awkward moments, the benefit of the doubt. Unfortunately, I don’t think we always have access to that in the moment because our own insecurities about judgement. A “bad date” is often misconstrued as a comment on the date-goer, and the outcome of a date is inherently closely tied to self-esteem. Date Night is an attempt on a surface level to shift the perception of dating away from the outcome determining self-worth and toward the process being about growth by practicing self acceptance and compassion for your peers.

The reality is meeting someone you don’t click with is illuminating. It helps shape who you are. When you have enough self confidence to say, I like/dislike that person but we are not right together, you’ve reached a level of self acceptance that is healthy. Too often I have found that that initial attraction, becomes a form of inertia, working against our own personal interests.

Dating is an important part of our lives. For some, it’s a process and it’s probably a process they only enjoy one time out of a hundred. Think about it in terms of that experience though, that one time when you click, that must feel amazing.

For me the experience has been different. When I started the podcast I was in an open relationship, so I was actively exploring the trials and tribulations of that type of relationship. It actually helped me compartmentalize the love of my partner and the lust of my sexual, emotional, and intellectual attraction to new people and new stories. Now, I’m in a committed monogamous relationship but I like to think not much has really changed in this regard. My partner asks that I sacrifice a physical relationship with other people but she would never ask me to give away my emotional and intellectual spontaneity. So while I could have fallen victim to the nesting phase of monogamy, Date Night challenges me to be open to the minds of others.

KG – You have a rather unique way of finding your guests. Can you describe this?

RM – I generally create profiles on online dating sites but I’ve branched out to using services for creatives like Model Mayhem / Twitter / LinkedIn. I think the only thing that is truly unique about finding my guests, is that I’ve never turned anyone away.

There are a lot of reasons why I started Date Night, as I’m sure I will expand on, but one was because I’ve always wanted to interview people. It only took me 27 years to finally do it. At first, I had the open door policy because I didn’t have a choice, but as it grew a little I wanted to test out my abilities, so I would still invite guests on that didn’t appear to have easily identifiable traits I could turn into narratives. What happened was that if you listened to one Date Night, you might say to yourself, “that’s kind of interesting”, “I liked her”, or “I thought she was snobbish or boring or whatever.” But, if you listened to five Date Nights you would pick up some sort of grander narrative that stayed true even though no one guest is the same. I felt like picking and choosing my guests would be guiding that narrative too much, and I didn’t feel that I could steer it in a better direction than it would take naturally.

One of my favorite quotes of all times is: “Although of course, you end up becoming yourself.” It is a quote from David Foster Wallace, that comes out at the end of some half baked, or half genius monologue about purpose. I think we spend so much time trying to contextualize our existence, and in regards to Date Night, I spend quite a bit of time trying to verbalize or think about what makes Date Night unique.

Mostly, I’m trying to explain it to myself, but my perception is such an infinitesimally small part of what it is. I have my perception, but I’m also saddled with my own misperceptions, and at the end of the day the show is about the guest. Ultimately, I’m desperate to understand what it is, so I can tell people and I can say, “look at what I’ve done! Look at what I’ve created!” Alas, even now it remains ineffable.

KG – What do you find to be the main challenges at the moment?

RM – The challenge is always purpose. Why am I doing this? The practical reason is that I’m yearning, stretching, and striving to find a job that feeds my creative needs; but it is also fun. I know there is a third reason, but I don’t think I’m ever meant to know what it is.

It’s the result of some kind of instinct to follow my ideas, but the interesting part is one never knows whether your instincts are efficient, accurate, or even purposive. We want to think they are right, it’s some how powerful for us to know there is something untouched by logic inside of us, but people fail and succeed, you can’t have it both ways.

I want to feed the goal of furthering my career and the reception for Date Night is pretty strong. But, there is a kind of burden of talent behind it. Yes, you say I’ve hit on something, you say I’ve got talent at this interviewing thing, but I can’t monetize it and to continue it I have to alter my life to be someone who works 24/7 doing mostly marketing, which I don’t hate as much as others, but it’s not the work, you know?

What someone came to you and said continue doing this project you created, you love, and fits exactly what you want to be doing, but with that comes 40 hours a week of pushing paper. OR you could build up a resume of click bait articles, and yes you’d have to writing that garbage for the rest of your life to squeeze out a living but atleast you aren’t pushing paper.

Ultimately, your mind is already made up. It’s just a matter of when you accept it. Just like in relationships that have been over for a long while, we linger on these decisions and we stick in situations far after we’ve decided to get out of them. Right now, I’m in a period of transition. I’ve already decided to go broke for my creation. My job is to keep my promise to myself, keep my mind and body right, and push as far as I can get until someone tells me to stop.

KG – You’ve mentioned a number of times on Twitter the woes that come from looking at your number of downloads. How do you handle that?

RM – This is a bit of a red herring because Date Night has always had the most downloads of any of the podcasts that I do. That specific sentiment stems from what came after our most successfully downloaded podcast. The podcast is called “Same” and it’s my date with a gay man. It was picked up by a gay lifestyle magazine and the downloads went through the roof. However, as time passed by they slowly declined and I only saw a slight bump from this in our penultimate episode. It was depressing. It made the striving toward downloads, or success seem like a fool’s errand. It made the work feel lost. I had a very hard time getting over that.

KG – Date Night disappeared for a little while, where’d you go?

RM – I actually started Stand Up classes and was soon hitting up open mics as much as I could. I didn’t want to give up Date Night, but unfortunately, it was the only project I was doing at the time that didn’t involve other people. Also, I had the feeling after “Same” of… what else can I do? That’s the most successful podcast I’ve ever done and mostly it was because of the sexuality gimmick. Is this it? Is this just the finality of this project. I might have gone on thinking this, but the world has a way of telling you what it wants. The people in my life who are really paying attention – my partner, you, Shaun from the podcast No, Totally – constantly remind me, not with compliments, but lament that they aren’t getting their product. When someone misses what you’ve made, it’s much more of an incentive than downloads.

[KG here, I can totally agree with that last statement. It’s not fame, or fortune that I have come to want from anything that I do, it’s people showing they love it by asking why I’m not giving them what they have come to enjoy]

KG – Where do you see the future direction of podcasting to be?

RM – The future of podcasting is exciting. It’s difficult at the moment to monetize them, but art has always dealt with this issue.

Anytime you unspecialized a medium and let it amplify the voices of the yet unheard, we are all better for it. That also includes those you staunchly disagree with. People always give the old line of: “everybody has a podcast now”. Yeah, isn’t that completely amazing?

If you want a clearer picture of what I’m talking about read Kafka’s Before the Law. It’s a story about a man who goes to request some change in the law, but is made to sit outside the gates until his death (so many liberties with this synopsis for brevity’s sake).

This is how funded media is naturally. They control the message simply because they can. But, because they have their hand on the hose, they are much more susceptible to be controlled by the man who pays for the water. It might be easy to control some dude in his basement with a mic and Garageband, but it’s nearly impossible to wrangle a thousand of them.

KG – When you talk to friends and family about Date Night, do they get it?

RM – I love this question. No they do not. No one understands it unless they listen to it and I’d venture to guess that I’ve lost plenty of listeners, because they didn’t stick with it past one episode. It really is something that takes a while to understand. It’s a significant problem in marketing the podcast. I still haven’t figured it out.

KG – What drives you?

RM – I don’t sit still. I’m a naturally driven person. At times, it works against me. I’ve had times in my life when I simply don’t have something to chew on and it turns inward either by self destruction, or stress. Luckily, part the journey is learning these things about yourself and I understand that I need to have a project to focus that excess energy on. I think I would work best with a creative partner that is a “Narrower”; someone who is able to maintain the same drive, but while only focusing on one thing, honing, and crafting that one thing.

KG – You just announced that you have quit your job. This is a big step in the journey of an individual stepping away from the “normal career path”. How are you feeling about this and what are you doing?

RM – I’m very excited. I have money for about six months to pretend like my job is the exact thing I want to do everyday. The long shot is that one of my projects hits and I’m able to live off it’s income. In today’s climate, I’m not sure how realistic that is. My realistic goal is somewhat abstract, I want to become the best version of myself in this next 6 months. When I run out of money, I should have a portfolio of someone who has spent quite a bit of time rounding into form. My work should be better than it ever has before. At that moment, I assume I will be the most employable I have ever been. Further, I will never be able to look in the mirror and regret not having taking a shot at my vision of who I could be. I’ve never thought of myself as a great artist, or my work as untouchable, I just want an invitation to the ball, I want to sit at the table, I want to compete.

KG – Now, the best part of every episode is when you hand the show over to your guest to say whatever they want. Some of them prepare, whilst others seem shocked into silence. I thought I would hand the blog over to you. So, it’s up to you to say what ever you want.

[KG gets up and leaves the keyboard]

RM – Now I’m speechless.

I’m trying to create something. I don’t know where it will go, but I’m not afraid to be honest enough to take you along for the ride. In the end, inevitably, I’ll end up becoming myself.

I hope you enjoy the characters that enter and exit. I hope it makes you wonder how many beautiful people you meet but never talk to every day. I hope it speaks to something human.

I hope.

Roscoe Myrick hosts the podcasts Date Night and Shits Legit and can be found on Twitter. He is also a photographer.

Let us know what you think in the comments.

Seth Godin on The Moment Podcast

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I also recommend The Moment podcast as my new hot podcast pick. Delve into the archive. 

Well worth a listen

Interview on Build Your Platform

I was interviewed recently on Andy Stitt’s podcast, Build Your Platform.

I had a great chat on building your platform, shipping, and a little bit on how I have had some success with building my platform by taking some simple steps.

And it started by blogging once a day, for seven days.