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 and marketing, which – for the most part – I found supremely unfulfilling.
In 2013, my dad, 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 began working 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, LifehackThought Catalog, Elephant Journal, YourTango, The Good Men Project and other places.
I’ve traveled all over the United States 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. I usually just encourage people to read about it on Wikipedia.

Why did you start your blog?
For one thing, I enjoy writing. A lot. 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 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?
Admittedly, I used to assume that life coaching was total nonsense. And, I’m still not a huge fan of the term “life coach.”  But, one phone call with a refreshingly vulgar, no-bullshit, whip-smart, massively inspiring life coach single-handedly changed my perspective.

I battled depression and anxiety for many years. 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 pushed me to 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.

Do you still do stand-up comedy?
No. But, I think about it a lot.
Do you still work with Neil Strauss?
I don’t. But, we exchange emails every once in a while. And, I’m lucky to call him a friend. 

me in nola

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, my awkward encounter with a hooker in Chicago, or my experience at a Jewish summer camp, you can purchase the book here.  Shit, maybe it’ll become a cult classic or something.
My other book, which was spawned from a website, is called Randy Penny: Cordially F*^#ing With People. It’s 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, but you can try and buy a copy hereOr, you can check out the website.

Are you writing another book?
Yes. I’m currently working on a book more closely related to the content on this site.

Who designed your website?
Over the years, I’ve managed to teach myself web design and always did my own design work. But, the site you’re looking at now was crafted by my friend
, Brandon Pfeiffer, a talented designer and musician who lives in Chicago.

Who took your photos?
Almost all the photos of me were taken by Liz Daino, a wonderful photographer in New Orleans. 

Why did you move to New Orleans?
New Orleans is the most bizarre, beautiful, interesting, exciting, fun, 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].

What’s the best way to stay in touch, get updates, etc?
Join the tribe and sign up for my email list!