Mike Roberts didn’t set out to create a podcast interviewing elite-level horsemen and women, or grow a social following almost 144K strong.
In reality, he’s a self-professed introvert whose first love was playing baseball in his home state of Louisiana.
It wasn’t until he started indulging his curiosity with horses and horse trainers, and began riding that the trajectory of his career and his life drastically changed.
With a little help from a random cameraman, and a drunken redneck who helped coin his moniker at a house party — his brand, Converse Cowboy, was born.
If you enjoy this post, leave a comment on LinkedIn or Facebook. I’d love to hear your thoughts. And share it with a friend who would enjoy!
Humble Beginnings
If you haven’t seen his faceless quotes, or interviews with western performance industry giants including Tim Smith, Chris Dawson, and Dale Brisby, you’re missing out.
But Mike wasn’t born on the back of a horse — he actually grew up playing baseball in his native Louisiana, and ended up in real estate development. Always one to chase curiosity, Mike was fascinated by horses and horse trainers — particularly how they could communicate with a 1,000+lb. animal and get them to want to do what they wanted.
This led to him riding with some of the best in the industry, soaking up their knowledge and wondering if he could make something out of this passion.
He had the experience and information in his head and his personal journal, but how could he get it out into the world? Allow it to impact others in the western industry? The answer — audio and video. Only there was one problem — he didn’t know the first thing about either.
As luck would have it, while working on a project in Cowtown, Mike started up a conversation with one of the cameramen.
On a whim, the guy invited him to his home in Austin to learn how to film. So he went. After running through the basics, and seeing how passionate Mike was, the guy asked him why he didn’t have a podcast?
His answer? He didn’t know.
The guy told him - buy a decent microphone and start a show. Then he asked, what’s next?
His answer? He didn’t know.
The guy told him to start reaching out to those he’d worked with in the horse industry and see if they’d let him interview them. After another couple rounds of the “what’s next?” question, Mike had a rudimentary plan in place to start a podcast. But what the heck would he call it?
The name Converse Cowboy was actually coined from a drunk redneck at a Louisiana house party (if you’ve never been, you’re also missing out).
Mike says he walked into the party in his Converse sneakers, bootcut jeans and cowboy hat, and the guy said, “who do you think you are? The Converse Cowboy?” While Mike does like wearing Converse, the name is also a clever play on words since he “converses” with people.
The name stuck.
He also says he now has a much greater appreciation of what women go through when they’re ogled in public — anywhere he goes people first look at his feet (to see the Converse) then make their way up (to see the cowboy hat).
From Physical to Digital Real Estate
One of my favorite interview questions is asking people about their creative process, and how they come up with content their fans love.
When it comes to tapping into an online audience and getting them to engage, Mike is one of the best I’ve seen. Even better than his creative chops — his answer:
I do what I find curious to me.
But with a background in physical property development, what I really wanted to know is how he took that experience and used it to kickstart the creative side of his brain into highly sharable content online.
The faceless poster quotes he shares on his social media pages — he says he’s been doing that for years. The quotes are actually his own personal journal prompts. Like every other human, he says he struggles with finding purpose in life, as well as dealing with imposter syndrome. Writing helps him make more sense of things.
He says he constantly asks himself, “Why would people listen to me or care about my show?”
Yet he encourages his guests that, “you are what you are - share that.” Which instantly puts them at ease. That, and his casual way of interviewing — more like a conversation between friends, guided by a guy who holds onto that genuine, childlike curiosity with both hands.
A guest once told him, “I feel like you’re in my brain — like you can see exactly what’s going on in my head.”
That’s one of his unfair advantages — making his guests feel seen and heard.
“For whatever reason, we all think we're on our own little island dealing with our problems in a vacuum, but we’re all just trying to figure life out as we go.”
He equates it to a shroom trip — says we're all on one.
A Cowboy Work Ethic
His other secret sauce? Consistency.
According to his data, 80% of podcasts started back in 2018 when he got going are dead and gone. He says if you want to have success at something, just keep doing it — even if at first it seems no one is listening or watching. The really cool conversations he’d have with horsemen and women before he started the podcast?
He’s still having them — he just put them on a platform so millions of people can join in.
Get a sneak peek of his show:
However, as anyone who’s ever posted online will tell you, there’s an ugly side to a public journey of self-discovery. Putting your stuff out there and learning how to deal with other people’s egos, judgments and just plain crazy is hard. Really hard.
But Mike always looks for the silver linings and focuses on a growth mindset. His philosophy on the haters?
You can let it beat you down, or you can learn from it.
He attributes his “glass half full” attitude to lessons he’s learned horseback. In fact, right before our call for this interview, he was in the arena working with a horse. He says every day horses are looking to us to know what we want and vice versa.
It’s the same in business.
“My people are looking to me, and I'm teaching them in some capacity. Whether I'm there, or have systems set up for when I’m not. It’s about setting boundaries.”
Mike fully admits his creative muscles aren't as strong as his entrepreneurial ones, because he’s only been creating for about a year and a half. To work these, he’s always trying to think, “How can I be most efficient with my time?” He advises those whose brains work the same way as his, to think of their time this way:
Spend your most productive hours working on the things your brain isn’t used to (ie. needs more energy for). Save the tasks you don’t have to think about as much for later when you’re tired, rundown or just tapped out. For Mike, writing out his posts, or researching for upcoming interviews requires a lot of brainpower. While things like setting up meetings with potential buyers, actually conducting the podcast interviews, and writing in his journal are second nature.
Mike’s a morning person, so that’s when he does his deep work. But you know yourself better than anyone, so figure out when you’re most productive and create a schedule around that.
Mike’s advice: whatever you do, don’t overcomplicate it.
Horse S#$%…
The path to success sure as heck ain’t a straight line.
When I asked Mike about a lesson he learned the hard way, or something he tried that completely blew up in his face, he told this story…
I started Converse Cowboy during COVID. Soon after I hired a camera crew. We’d go out and do interviews, and I was real focused on building the brand. I was hustling!
I ended up doing a special with three big cutting horse trainers right around the time of their futurity. I even got their association to pay for it because they said they wanted to be a part of things.
When that project was over, we met and left with a handshake deal to do three more together for a set price. But when we’d wrapped on the first one, the videographer demanded more money. The guy also struggled with some mental health demons which I was trying to be respectful of, but eventually the shooting schedule overwhelmed him, which put me in a tight spot with the association.
A few weeks later, I found out the association went directly to the videographer and cut a deal with him to finish the projects without Converse Cowboy.
I thought, “I finally get a big break and I get stabbed in the back.”
After that, I needed a break. To be honest, I didn't create much the rest of that year.
What I learned is you need to constantly recalibrate your brain. I felt like it was the universe's way of realigning what’s important to me. I spent a lot of time by myself and journaling. I’m not still bitter about what happened, this is just my perception of it.
Bottom line: it's not always sunshine and rainbows.
Mike says there’s behind-the-scenes work on projects don’t pan out that the audience never knows about.
But he’s always willing to try again. That persistence and unwillingness to stay down is what’s allowed him to build his brand to over 144K followers, and one of the top-rated podcasts in the Philosophy category on Apple Podcasts and Spotify.
Growth Hacking - Western Style
Mike says growth in any business isn’t rocket science, but it does take time and patience.
The biggest indicator of success in his opinion?
If you can provide value in some way, your deal will work.
He says no matter what your brand is, when you can share what others are doing, your deal will grow too. It’s the law of reciprocity. Early on he would post something and think it was going to do really well and it would flop. On the flip side, things he thought didn’t have a snowball’s chance in hell of working, did great.
His go-to growth hack?
Pay attention to the market, and those doing it better than you.
For him that’s guys like Dale Brisby and Gary Vanyerchuk. Definitely don’t steal what they're doing, but study them — see what times they’re posting, what format they’re posting (text only, video, carousels etc). Find someone in your niche doing what you want to do on a very high-level, and treat them like a science experiment.
He also says — you know what your intentions are, be very clear about them.
So who’s Mike’s so-called ‘Category Creator’?
None other than self-professed bull-riding gypsy turned YouTuber with over 655K subscribers, Dale Brisby. Calling him “one of the coolest guys I know”, Mike says despite Dale’s celebrity in the western industry, he’s always very welcoming. Even spending time helping Mike on some of his videography. According to Mike, “that guy's the real deal.”
Anytime Mike sits down with a guest, his goal is to have the conversation show you the real version of who that person is.
Being an introvert, he thrives in the 1:1 podcast setting, and says there’s an unspoken agreement between him and his guests that things can get very real. And while he never expects someone to answer a question they don’t want to, Mike says having that uninterrupted personal time with someone is rare in today’s digital landscape.
Between the wealth of knowledge he gets via the interviews, his Converse Cowboy notebook, and his personal journal, Mike’s got plenty more growth tips — he’s always happy to share!
Mindset Matters
When it comes to habits or routines that help Mike stick to his positive/growth mindset, he says “you either have it or you don't.”
Mike grew up in a family where his dad was his biggest advocate. He says he doesn’t think his dad even realized what he was doing, and how much impact it had on his son. He gives the example of if he was having a nightmare, his dad would come into the room and tell him to think good thoughts.
“Think about your (baseball) game coming up.”
He admits it’s not easy, and again, consistency pays off, but you have to train your brain to focus on things you want to happen. In full transparency, Mike didn't read a book until he got out of college (and that included the school years). But one book that’s stuck with him all these years — Napoleon Hill’s Think and Grow Rich - Law of Attraction.
He considers books extensions of mentors.
One thing I love that he does with his books is he uses different color highlighters for different readthroughs (ex. yellow first time through, orange the second and so on). Each time you read a book you’re going to get something different out of it. Tracking those insights really helps you see what you missed the first time.
Ever humble, Mike says if he seems further ahead than others, it's because he’s stood on the shoulders of giants.
He also sticks to the habit of continual learning. He says during recent end-of-year reviews with his real estate employees, he was meeting with a young girl, who (in his words) is a “badass, she’s killing it at the job.” When the topic of setting next year's goals came up, he asked her how she sets them — she floored him by saying “video journaling”. He’d never heard of it.
And while he’s old-school and sticks with pen and paper, he’s a big proponent of “using your mind to sharpen your mind.”
In other words — thinking about things in different ways so you can continually improve.
Greener Pastures?
I always ask those I interview for these success stories, “what’s the best piece of advice you were given (personally or professionally) that helped shape you into who you are, or where you’re at today?”
And if it sounds cheesy and cliche, you’re not wrong.
But cliches are there for a reason. They’re true 9 times out of 10. And as Mike mentioned a few times during our conversation, Converse Cowboy began as a soul-searching journey.
He’s had it all. And lost it.
He had the beautiful wife, the 6-figure paycheck, a 300-acre piece of God’s country. But it wasn’t enough. His thirst for more wasn’t quenched, and he never stopped looking for a bigger box to check.
When he went through a bad divorce, his idyllic life came tumbling down. He lived in a 1-bedroom, white-walled apartment that made him feel like he was in an insane asylum.
But through it all he found his way to greener pastures.
On The Horizon
So what’s next for this humble cowboy? He’s currently writing a book that (hopefully) will be out next year. The theme of the book is (aptly) gratitude, a pillar value in both Mike’s personal and professional life.
And he has a lot to be grateful for.
When he was in the dark, he thought gratitude was complacency.
I can't be grateful for this because I'm not a complacent person.
What he’s learned is, you have to be grateful for what you have. Life has a funny way of giving grateful people more to be grateful for.
One of his favorite quotes is by Ray Wylie Hubbard and is pinned on his Instagram:
The days I keep my gratitude higher than my expectations, I have really good days.
Adding that one to my wall immediately.
~
If you want to connect with Mike, he hangs out here👇
www.conversecowboy.com
Apple iTunes or Spotify
Watch the show on YouTube
Thank you for joining me on this edition of Western Writing Weekly's Cowboy Success Stories.
Until next time, always remember to...
Enjoy the ride,
Charlie
P.S. Thanks again Mike! Make sure you connect with him to follow his journey.
If you enjoyed this, hit reply and let me know. I’d love to include more stories like this if you did. Sure, they help everyone, but I think it’s always neat to see how others grow even at a smaller scale than the ones that typically get talked about 🙂