You’re Probably Wondering Who I Am


I’m an author, blogger, certified coach, heartbreak recovery expert, internet entrepreneur, music nut, comedy nerd, gastronome, thinker, dreamer, wanderer, and a bit of a hopeless fucking romantic. I was born and raised in Omaha. I graduated from the University of Wisconsin with a degree in communications and a minor in Spotted Cow. Then, I moved to Chicago, where I tried my hand at stand-up comedy and studied writing at The Second City. Eventually, I moved back to Omaha to be closer to my family and continue writing. While in Omaha, I spent over a decade working in advertising, which – for the most part – I found supremely unfulfilling.

In 2013, my father, who was the picture of health, died suddenly and unexpectedly while exercising at the gym. For better or worse, this sent me down a path of deep self-exploration, on which I realized that life is simply too short and too unpredictable to settle for anything less than what you truly want.

In 2015, I worked for transformational journalist and nine-time New York Times bestselling author, Neil Strauss (The GameThe Truth, Everybody Loves You When You’re Dead).  More than anything, Neil taught me the importance of stepping outside your comfort zone, facing your fears and taking action.

My writing has been featured in The Huffington Post, Lifehack, Thought CatalogThrive Global, Elephant Journal, YourTango, The Good Men Project and other places.

I’ve traveled all over the country and, in 2016, I decided to move to New Orleans.


Omaha? That’s in Nebraska, right?

Yes.  And, no matter where I go, somebody inevitably asks me this question.  Omaha is actually a great city with a lot to offer, especially if you’re raising children.  I usually just encourage people to read about it on Wikipedia.

Why did you start your blog?

Well, for one thing, I love writing. And, I’m endlessly fascinated by psychology and human behavior. I’ve spent years studying the research on things like happiness, confidence and relationships – mostly to overcome my own struggles. I’ve also read hundreds of self-help books, many of which explain what to do but not how to do it. Love myself? Ok. How? Practice mindfulness? Sure. But, how? Be a non-judgmental observer of self? That sounds awesome. How the fuck do I do that? Writing helps me sort a lot of this shit out. And, with any luck, I’ll help some others along the way.

Why did you decide to get certified as a coach?

I used to assume that life coaching was complete nonsense. In fact, I hate the term “life coach.”  But, one phone call with a refreshingly vulgar, no-bullshit, massively inspiring life coach single-handedly changed my perspective.

I battled depression and anxiety for many years. I lacked purpose and passion. I saw several doctors and therapists, tried a variety of medications, even experimented with hypnosis. Nothing seemed to work for me. I genuinely thought I was a lost cause. A life coach helped me change my thinking, set goals, stop making excuses, grow some balls and take control of my future. After working with a coach, I knew I wanted to become one.

me in nola

Do you still do stand-up comedy?  

No. But, I think about it a lot.

You say you’re an author. Have you had any books published?

Yes, I’ve had two books published.  One is a collection of personal essays called I Hope There’s Pie. I wrote much of it when I was 22 years old, and I don’t suggest adding it to your collection. The writing is sloppy and many of the stories are disjointed. Whenever I go back and skim through it, I cringe a little. Quite frankly, I’m surprised it ever saw the light of day. However, if you’re interested in reading about my childhood cat or my experience at a Jewish summer camp, you can probably purchase the book here.  Shit, maybe it’ll become a cult classic or something.

I also have a humor book called Randy Penny: Cordially F*^#ing With People. It’s pretty funny, and I highly recommend keeping a copy on your coffee table or in that wicker basket next to your toilet. Here’s what my friend and one of my favorite comedians, Nick Griffin, said about it:

In the grand tradition of the Lazlo Letters and Letters from a Nut comes the next generation of mess-with-their-heads correspondence, Randy Penny. This stuff is Laugh Out Loud Funny from beginning to end. No cursing, no yelling – all of it hilarious. If you don’t think this book is funny – kill yourself.” 

Unfortunately, the book is out of print (I’m actually working on giving it a second life). But,  you can try and buy a copy here.

Are you writing another book?

Yes! I’m currently working on a book more closely related to the content on this site.

Why did you move to New Orleans?  

New Orleans is the most bizarre, beautiful, interesting, exciting, fun, frustrating, and culturally rich place I’ve ever experienced. There’s really nowhere like it. If you live in New Orleans and you’d like to work with me, or just get together for a glass of whiskey, shoot me an email at [email protected].