The Gently Mad: Life, Business & Entrepreneurship without the BS

If you're looking for that inspirational kick-in-the-pants to help take your life and career to the next level... this ain't it. To be perfectly honest, I'm tired of all the "inspirational" BS that passes for entrepreneurial podcasts these days. You won't find any neurohacking, hyper-accelerated list growth techniques, or sleazy marketing strategies. What you WILL get are honest, meaningful conversations and discussions about things that matter. The struggle to find purpose and meaning in our life and work, how to deal with self-doubt, fears, insecurities and failure. All the stuff we face every day, but don't every talk about. Sure, there will be plenty of conversations about entrepreneurship, business, marketing, blogging, podcasting, audience building, content creation, etc. But the through-line that connects it all is true authenticity and honesty. No BS. No hype. No meaningless buzzwords designed to get you to waste your money on a useless product. Just raw, honest conversations about things that actually matter. If you like The Fizzle Show, The Tim Ferriss Show, Nathan Barry's podcast, Paul Jarvis' and Jason SurfrApp's Invisible Office Hours or the #AskGaryVee show (ok I'm out of names to drop), you’ll probably enjoy this one. You’re mileage may vary.
RSS Feed
The Gently Mad: Life, Business & Entrepreneurship without the BS


All Episodes
Now displaying: Page 1
May 1, 2015

Since this is the last episode of TGM until mid-summer, I wanted to give you a prefer of what’s coming. 

Thank you so much for listening and supporting TGM during what I’m now calling “Season 1”. If you don’t know yet, I’m taking a break from the show to get my new show and course off the ground. As well as record some more conversations for Season 2 of TGM. 

You can subscribe to the new show and, if you feel like being awesome, leave me a rating and review. 

Also, check out the Ultimate Podcast Bundle. A lot of cool stuff and the price will continue to go up $1 with each purchase. 

Enjoy the show!

Check out the full episode description and show notes at

Apr 29, 2015

It’s really great that I wanted to talk about systems and processes, because there’s no one better with whom to have that conversation than Amy Porterfield.

She’s created a very successful business teaching people about online marketing and we spent a lot of time talking about the ins and outs of that. 

This is definitely an atypical episode because I really wanted to dig into some tactics, given that I’m going through my own product launch at the moment. 

Nevertheless, we did touch on some of the bigger issues, such as burnout, the pursuit of freedom and the bigger purpose behind what we do. 

Check out the full episode description and show notes at

Apr 28, 2015

Paul Jarvis is one of those guys who frustratingly always seems to have everything in balance. 

He knows how to work hard, but how to take breaks and have fun as well. He seems happy and content with his work and is able to change it up when he needs/wants to. 

Basically the opposite of everything I did when I was a full-time freelancer. 

In all seriousness, though, Paul and I talk on a fairly regular basis and it’s great when we’re able to record a conversation like this—about meaning, happiness, what we like, what we don’t, what we wish were different. 

This is my favorite kind of TGM episode.

And Paul is a great, no-nonsense guy to learn from. He lives near the beautiful Canadian west coast and has purposely surrounded himself with the peace of nature, but still has a thriving career as a designer, writer and teacher. 

Enjoy the show!

Check out the full episode description and show notes at

Apr 23, 2015

How do you interview someone you’ve known your whole life?

Nate is a Grammy-nominated musician, whom I met when I was 12. We started one band together when we were teens and then later in my mid-20s I joined his current band as the drummer. 

After one album and a couple years of touring I ended up leaving the band, but Nate has stuck with and continues to put out music that just gets better and better. 

Besides being one of my best friends, Nate’s story is a perfect example of sticking with a dream even when it practically kills you. Lots of ups and downs both financial and personal, but he’s stuck with it and I admire him for that. 

I’ve never had someone on the show that I had this much history with and had known for so long, so, honestly, I wasn’t sure how it was going to go. 

But I’m glad we did it because it turned out great. Despite all my curmudgeonly attempts to not be inspirational, this one definitely veers into that territory. He may not admit it, but I think Nate is an optimist, and like he says, you really can do whatever it is you want to do with your live—if you’re willing to put in the required effort and stick with it. 

Check out the full episode desciption and show notes at


Apr 20, 2015

Dan Haseltine is the lead vocalist and founding member of one of my favorite bands, Jars of Clay. 

Our conversation was one of the first in-person interviews I recorded and certainly the first with an artist that has had such a huge impact on my life. 

I’ve been listening to Jars of Clay since their first album was released in 1995 and can attach specific songs to specific experiences as a teenager, college student and, later, husband and father. 

It was truly amazing to get to sit down with him in Sputnik Studios in Nashville for an hour and talk about the history of the band and his personal evolution as a person and musician.

Check out the full episode desciption and show notes at

Apr 15, 2015

In Part 2 of my conversation with Omar, we dig into many of the various businesses and projects he’s launched and what it is that has kept him trying new thing without burning out. 

Omar is an incredibly hard worker, that much is clear. But, as I said in part 1, I was continually struck by his perseverance. He’s the kind of guy who keeps working, long after many of us would have quit. 

I hope you enjoy part 2 of Omar’s incredible story. 

Check out the full episode desciption and show notes at

Apr 13, 2015

I’ve listened through this conversation several times now and I keep coming away amazed at how willing Omar is to take chances.

That’s why I titled it The Power of Self-Discovery, because there’s something to the idea of continually re-inventing oneself. 

Omar currently runs The $100 MBA and WebinarNinja, but he’s spent many years trying (and often succeeding) at many other things as well. 

As someone who has often missed opportunities because of various fears and self-doubts, it was incredibly encouraging to hear the story of someone who has made those leaps and found that the other side isn’t so bad after all. 

Check out the full episode desciption and show notes at

Apr 8, 2015

Allan Branch is the Ron Swanson of the internet. And not just because they share a fondness for manly facial hair. 

In all seriousness, Allan is a really funny and interesting guy who also happens to co-own the best accounting software in the world, Less Accounting. 

He’s one of those guys who can instantly raise my spirits no matter what’s going on. And I’ve always admired him for his ability to let work be work and enjoy having fun and spending time with his family.

As someone who has let all my hobbies fall to the wayside, I love how much energy Allan puts into his own non-work pursuits. He’s not driven by nor obsessed with his work. I want to be more like that.

If you’ve never met or talked to Allan, then settle in for a fun conversation about writing, building a software business, go-carts, hypothetical beer brewing and bees. Yes, bees.

Check out the full episode desciption and show notes at 

Apr 6, 2015

Natalie Sisson is the self-described "Suitcase Entrepreneur", because she's figured out how to travel the world and live out of her suitcase while running her successful online business. 

We talked about all the stuff I hope TGM has become known for by now—happiness, meaning, purpose and how we find those things in our lives and work. 

Good thing for me, these are topics that Natalie is not just passionate about, but helps other people figure out as well. 

Enjoy the show.

Check out the full episode desciption and show notes at

Apr 4, 2015

The episode in which my 7-year-old daughter teaches me a lesson about gratefulness. 

Enjoy the show. 

Check out the full episode desciption and show notes at

Apr 1, 2015

This is a very special episode. If memory serves correctly, this was the first episode I recorded for the new TGM last year, and I felt it was fitting to release it as episode 50. 

Jordan Cooper is funny funny guy and someone I would call a friend. In addition to being a Stand-up comedian, he's a web designer & marketer for small businesses in Louisville, KY. He's also a podcaster and at least four different shows. 

In addition to talking comedy and our respective careers, we talked about sticking with the things we start and the ever prevalent problem of quitting to soon.

Jordan busted my balls about not sticking with anything and wondering if this podcast ever actually launch, which makes it a fitting "fuck you" as episode 50 fo TGM. ;)

In all seriousness, I love Jordan and really enjoyed our conversation all those months ago and am excited to share it with you. 

Enjoy the show. 

Check out the full episode desciption and show notes at

Mar 31, 2015

Daniel is a respected podcaster and someone I've wanted to talk to for quite a while. He's also a successful entrepreneur and has managed to build a business that supports his life and not the other way around.

It was my honor to get to speak with him for an hour about podcasting, building online businesses, branding and all sorts of topics that have lately been rolling around in between my ears. 

Whether or not your into podcasting, Daniel has a lot of wisdom about life and entrepreneurship and we had a great conversation. 

Check out the full episode desciption and show notes at

Mar 27, 2015

Successful people are lucky. But it has nothing to do with chance and everything to do with work.

I don’t consider myself to be someone who has a lot of skills. But if there’s one thing I've been able to do over and over again, it’s create my own opportunities.

In today's episode, I talk about five ways you can do the same. Enjoy.

“You are a product of your environment. So choose the environment that will best develop you toward your objective. Analyze your life in terms of its environment. Are the things around you helping you toward success - or are they holding you back?” ~ W. Clement Stone

Check out the full episode desciption and show notes at

Mar 26, 2015

Jon Nastor is a great example of someone who knows when to quit and when to stick. He wasn't born with this knowledge, but gained it through experience. In other words, he didn't quit.

I met Jon less than six months ago, but we hit it off pretty quickly. He's the host of the popular podcast, Hack The Entrepreneur and we went deep into the struggles of building a business when it seems like nothing is happening. Jon pushed through months and month of "not knowing" with his podcast. But because he kept showing up, eventually he opened doors that never would have been opened otherwise. 

I love the fact that Jon is ready and willing to admit he didn't know what he's doing, but he knew one really important thing: keep showing up. 

And because of that, so many opportunities are opening up for him. We talked about all of that and what it's like to be on the other side of the dip. 

Check out the full episode desciption and show notes at

Mar 23, 2015

Laura Beggary is a great and funny writer. She is the creator of, where she provides copy for small businesses and writes promos for major television networks.

I've been getting her newsletter for several months now and it’s a truly unique breath of fresh air in an industry where everyone’s trying to sell you something. It's not about writing tips or "leveling up". It's about her personal life and she has a way of telling stories that are witty and heartfelt.

We talked about everything from our shared love of NYC to our distaste for online marketing buzzwords and bullshit.

In addition to building a solid reputations as a TV writer, Laura has also managed to create an amazing freelance business as a writer for entrepreneurs. Her forthcoming course, The Copy Cure, with Marie Forleo, is all about finding your voice as a writer, minus the tired and cliched advice spouted by most "writing" courses.

I found her to be a super genuine and endearing person. I loved talking to her and wish we could have talked for more than the hour and half we did. Maybe she'd be willing to do a part 2 some day.

Check out the full episode desciption and show notes at

Mar 20, 2015

You know that guy or girl who keeps asking you (and other people) for advice even though you’ve already told them what to do?

That's me. I do that all the time. In fact, I just spent a whole week doing that, instead of doing what I already knew. 

Getting advice, researching or preparing (after a point) is a really sneaky way of procrastinating and letting our self-doubt win.

In this episode, I talk about a few things that can help if you find yourself in that situation.

Check out the full episode desciption and show notes at

Mar 18, 2015

Christa Wells is an award-winning songwriter and I was honored to talk to her about what it really means to be an artist, how to stick with it, even when you're broke, and how she's made her own luck instead of waiting to be noticed. 

So much great stuff in this episode. I first heard about Christa because of he latest album which covers songs from Nirvana, The Smiths, Depeche Mode, Smashing Pumpkins and U2. All favorite bands from over the last 20 years of my life.

I'd been listening to the album on repeat when I decided to reach out to her and see if she'd be interested in coming on the show. I'm so glad she said yes. Like my conversation with Donald Miller, we talked about the art itself, but so much more than just that.

Christa is a deep thinker and I loved talking with her about art and artifice, business, the idea of the "tortured artist", and many so much more.

Every artist in an entrepreneur and I loved getting Christa's take on these topics.

Check out the full episode desciption and show notes at

Mar 16, 2015

Thomas Frank is doing and thinking about the kind of stuff I wish I had been when I was 23. Not only does he live full-time off his blog, but he's really good with money. 

Damn him and his productivity! Just kidding. I enjoyed getting to know him and talk about what it's like to run a website full-time at that age. As well as his plans for getting published and retiring by the time he's 40.

Check out the full episode desciption and show notes at

Mar 13, 2015

I was determined not to do it again, but I did anyway. It’s 6a.m. on launch day and (having stayed up all night) I’m still working furiously to finish my online course so I don’t disappoint the 132 people who pre-purchased. 

“Why do I keep doing this?”, I thought. I would like to think I’ve matured in 15 years, but I’ve been repeating the same all-nighter-before-a-deadline pattern since college. 

It worked fine then when the stakes weren’t as high. But now I have a family to support and bills to pay and every time I pull an all-nighter to meet a deadline, it wreaks havoc on my schedule, not to mention my health (it takes a lot longer to recover at 35 than it did at 20).

Sure, it’s my first product and I vastly underestimated how much time it would take to make, but you would think I would have learned this lesson by now. 

I’ve plowed through half-a-dozen different careers since I was 20, but this whole deadline thing is the common element that connects them all together. 

Procrastination is something I’ve never been able to shake. But this time, as I look back over the last 90 days, I see a lot of things I wish I had done differently and hope I *can* do differently the next time. Here are 10 of them:

Check out the full episode desciption and show notes at

Mar 11, 2015

Jason VanLue is on the show today talking about family, priorities, work and going from Designer to CEO in 5 years. 

The first time I talked to Jason about being on the show was more than a year ago. But we finally made it happen and he has quite a story. 

Check out the full episode desciption and show notes at

Mar 9, 2015

As an interviewer myself, I count myself as one of Andrew Warner's many fans. It was great to sit down with him and ditch all the facades of business and tactics and get right down to personal struggles we both face. 

It's one of the stranger interviews on TGM, in that Andrew is so passionate, he doesn't have any problem calling people out (including me). And even though I may have been uncomfortable at times, it was great to dig a little deeper into who I am and what I'm doing, as well as get the same from Andrew.

Check out the full episode desciption and show notes at

Mar 6, 2015

In part 2 of my conversation with Myke Hurley, we talked about his show Inquisitive and how he's turned it upside down to create something new, as well as all the fears and struggles with taking something succful and turning it on it's head. 

Myke Hurley is the British guy you keep hearing on podcasts. He has been talking in to a microphone since 2010 and lives just outside of London, England with his sticker-coveredMacBook Pro.

Check out the full episode desciption and show notes at

Mar 4, 2015

I'm super excited to have Myke Hurley on the show today. We've been friends for a couple of years, but this is the first time we've shared the airwaves together.


Myke Hurley is the British guy you keep hearing on podcasts. He has been talking in to a microphone since 2010 and lives just outside of London, England with his sticker-coveredMacBook Pro.

We talked about Myke's dream of being a full-time podcaster, the multi-journey to get there and the new challenges he faces now that he is there.

Myke is an inspiration to keep at it no matter how difficult. 

This is the first TGM two-parter. Yes, I'll be back on Friday with the second half of our conversation.  

Check out the full episode desciption and show notes at

Mar 2, 2015

I don't think I've enjoyed a conversation lately as much as this one. I didn't know Josh before we spoke, and as much as I hate being "inspirational", I kind of couldn't help but be encouraged.

We talked about the illusiveness of success and the exhaustion of always trying to attain it, as well as what happens when we finally let go and just be who we are.

For Josh, it comes down to being willing to ask for help and "humiliate" oneself.

I can't even describe how great this conversation was (all due to Josh). Whether you're struggling or not, this one is worth your time.

Josh has been a public speaker since he was 17. He toured with Bill Cosby when he was still a kid, used to be on MTV’s Total Request Live, and just recently had his own TV show with Oprah’s executive producer.

He now runs a seven-figure business as a “youths” speaker and founder of Youth Speaker University.

Check out the full episode desciption and show notes at

Mar 1, 2015

Today I decided to shake things up and talk to my wife about what it's like being married to someone who is an entrepreneur and always trying one crazy idea after another. 

As usual, her perception is painfully accurate and and advice, spot on. I enjoyed having her on the show with me.

Check out the full episode desciption and show notes at

1 2 3 Next »