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  • The man, the myth, and the mustache - Gregory Benedikt’s clients live a story worth telling

The man, the myth, and the mustache - Gregory Benedikt’s clients live a story worth telling

Plus, why freezing your bippy off makes your brain younger


“It was not, in fact, bad sushi.”

Tell that to your group of buddies who are oh-so-kindly pounding on your hotel room door at the buttcrack of noon the day after a night of karaoke, sake, and the retrospectively suspect aforementioned sushi.

It was not the sushi that had Gregory Benedikt curled up on the bathroom floor.

It was a podcast.

The one he’d recently listened to, about the top regrets of the dying. 

The one that made his young - and some would say, charmed - life flash before his eyes.

The one that launched him into a full-on existential crisis.

Gregory was staring the top regret of the dying right in the face. It’s called Not Living a Life True to Oneself. 

It hit him hard. Hard enough to knock him off his axis entirely. Little did he know - although part of him must have suspected - he was about to take his epic mustache and walk away from everything he’d spent his whole life building.

But first, there was an uncomfortable conversation that needed having.

Wildlings, if you’ve ever had an existential crisis… or made the leap from comfy job to entrepreneurism… or wanted to live a more daring, adventure-filled life… or just need some motivation to keep doing hard things, this week’s edition of Entrepreneurs Gone Wild is for you.

Also, if you want the latest on the entrepreneur retreat center’s progress, and why we’re not freaking out about having to do our best Evel Knievel imitation driving out of the barn… well, we’ve got that for you, too, this week.

Oooh you’re going to want to jump on this.

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Where were we? Oh yes, fetal position on the floor of Gregory’s hotel bathroom in Japan. About as good a place from which to launch a whole new life and business and path as any.

Gregory had done everything right. And yet, there he was, feeling the void’s icy fingers on his throat, its whisper in his ear, telling him he’d already made his bed and it was time to lie in it. Forever.

He was running on tracks. Go to a great school and do well there. Get a job in finance and work in San Francisco. Make all the right moves. Work. Retire. Die.

But as happens, the dark thoughts swirling in his head nudged him into making some changes. And, as sometimes happens, the universe giggles about our plans. In this case, the giggle was the pandemic. 

Gregory counts it as a blessing because it was a catalyst for him. “We have this pandemic and nobody knows what’s going to happen. If I’m not going to quit my job now, when the world is potentially ending, then I’m never going to quit. I’m going to wake up at 55, be working in finance, be depressed, and wonder why I settled.” 

It’s these moments when entrepreneurs are born. And then, there’s the undoing phase.


That’s always a fun conversation to have. “Mom, Dad, I know you worked hard and sacrificed to put me through college. And I know how proud you are of me and my fancy-pants job. But… I’m going to quit and open my own business.”

“I’m sorry, you’re what?” is the customary response. 

It’s not that your parents don’t want to be supportive. It’s just that they’ve spent the past couple of decades prioritizing your safety and security… often above their own happiness and fulfillment. 

So, Gregory repeated himself and threw in the kicker, “Also, I don’t know what’s next. Fifty-percent of my plan is to have no plan.” We’ll leave the rest of that conversation to your imagination.

[Insert the Sponge Bob narrator’s voice here: “Four hours later.”]

In the end, Gregory said, “I’m doing this. I don’t need your approval. But I would eventually like your love and support.” That’s when they got on board. Thankfully, Gregory had their love and support when things got hard. And they got really hard. 

But Gregory had this… this soul calling, this inner voice calling him into adventure. And for the first time in his whole life, he listened.


Two weeks after Gregory quit his job, a stranger on the internet told him he had to meet this other stranger on the internet. As one does when a stranger on the internet tells us we have to meet this other stranger on the internet, he met said stranger on the internet. His name is Tim. 

Tim did not, in fact, kidnap Gregory, steal his kidney, and leave him unconscious and chained to a bathtub in a dusty motel room in Laughlin. Instead, he and Gregory started a nonprofit together.

That nonprofit led Gregory to a beautiful world he’d never imagined. He often says, “Just take the first step and see what happens.” 

What happened is that Gregory became a leadership coach. Along with co-founding a nonprofit. Then he added The Dare to Dream Podcast, which is outstanding, by the way.

“Live a story worth telling.” It’s Gregory’s life philosophy. It’s also tattooed on his arm. Yeah, he’s all in. It’s a constant reminder that serves him as well as his clients. Typically, they’re over 50 and they’re just starting to rediscover their passions, to consider pivoting into following their long-buried dreams. They don’t just chat. There’s transformational experiences to be had along the way through smashed comfort zones.


Gregory eats his own dog food, as he should. You don’t want a leadership coach coaching you to leave your comfort zone in the rearview… who’s so cozily ensconced in his own comfort zone that it’s like he’s got perma-couchlock. Nope. You want one who’s kind of a nut, one who can barely even remember what his comfort zone looked like. The kind of nut who’ll knock on a stranger’s front door to ask if he can do a cannonball into the guy’s pool.

You’re going to want to subscribe to Gregory’s Instagram account. You probably won’t even believe what you’re seeing, though.

So, Gregory lives and coaches by these six pillars: Boldness, Clarity, Health, Love, Fear, and Purpose. Sometimes that means taking on eyebrow-raising challenges. Sometimes with friends or clients. And sometimes, all by himself because the other guy backed out at the last minute.

Like that time Gregory ended up at the starting line of a half-marathon solo. His running mate was a no-show. Gregory was… a bear. He doesn’t love running. He kind of hates it, actually. Yet here he was, 13.1 miles ahead of him. By himself. Unexpectedly. You can feel that feel, right?

Running is a mental game. For the first half of the marathon, Gregory grumbled. Then it hit him… “If you’re going to be a bear, be a grizzly! You’re out here doing this thing. Might as well give it all you’ve got.” He ran really, really fast, won his age group, and got 13th out of 3,000… without training.

After our interview, this story came to mind one day when anxiety was getting the best of me. I was curious what would happen if I were to pretend I was a grizzly bear and just gave a righteous roar aimed at that feeling. Surprisingly effective! 


Gregory’s living a story worth telling, and he’s got the video to prove it. There was the, “Can I cannonball into your pool, Mr. Complete Stranger?” moment, but there were many others, too. 

Like when he:

  • Asked strangers if he could cook dinner for them in their home (no)

  • Asking if he could drive the Amazon delivery truck (no)

  • Asking if he could drive the mailman’s truck (also, no)

  • Asking if he could drive some construction workers’ steamroller (came close!)

  • Asking if he could get a discount for having an incredibly good mustache (yes!)

  • Teaming up with Stacey Lauren to ask strangers on the street to do the Macarena with them (yes!)

  • Asking a stranger if he’d do 45 seconds of uninterrupted eye contact with him (nope)

It’s the practice of being bold, of daring to do slightly crazy things, to see what happens. But even someone with a history of saying yes to slightly crazy ideas can hit the wall. It had gotten old for Gregory, and he convinced himself that he’d gotten everything he needed out of his “100 random bold asks” challenge. Now, he’d just do the remaining 34 by making bold proposals in his coaching business.

But he didn’t. And that made him realize he wasn’t quite done. The resistance is real. So, Gregory got the opportunity to coach himself back into to living a story worth telling. 

The new rule: All the moments where I could say “no” and live an ordinary life, instead I say YES.

Of course, when you make a rule like that, you’re going to get tested. Soon.

One night, Gregory was headed home after pickleball with his buddy. His buddy says, “Ha. What if we just jump into the ocean right now?”

It’s sunset. They don’t have towels. They don’t have bathing suits. Wet, sandy cars take forever to clean. All the reasons to say “no” made perfect sense. But Gregory remembered his new rule and said, “Screw it. Let’s jump in the ocean.”

They did. It was fun! And there happened to be a shower. They washed their feet, used their shirts to dry off, and used reusable grocery bags to protect their car seats. All those reasons to miss out… denied.


Gregory does transformational coaching. He has transformational conversations with his clients, sure. But he also custom-designs transformational experiences for them - experiences that change their lives. 

You do something that you or other people say is “impossible” and there’s an incredible thing that happens when you actually do it. You’re full of gratitude. You feel like a 10-foot giant with a hammer, unstoppable. And you wonder… what else could I do?

Also, your brain digs it. Dr. Andrew Huberman describes how this thing called the anterior mid cingulate cortex (aMCC) works. This is fascinating.

In a nutshell, it’s got to do with grit and resilience and your willingness and tenacity to do hard things. Studies show that when you do hard things that you don’t want to do, your aMCC grows. The size of your aMCC is linked to longevity. You want to be as sharp in your 50s, 70s, and 90s as you are in your 20s? You want to overcome challenges? 

Do hard things. 

Want to have way more fun while doing hard things? Do them with Gregory Benedikt. You’ll probably find him surfing, where he does his best thinking.


My family lives forever. Well, close. 3 out of 4 of my grandparents made it to 89, and one made it to 98. That grandfather had great advice about staying mentally and physically sharp: have somewhere to serve daily (where people will notice if you don’t show up), keep learning (dude took French, History, and Astronomy in his 90s, after finishing his medical degree right before WW2), and exercise every day. (Also, 1 oz. of Scotland’s finest daily at 5 p.m., no more, no less, no earlier, no later.)

Lots of us know about voluntary discomfort and how when you tackle something hard early in the day, you go into the rest of your day with a win under your belt already.

There’s a connection here… 

Do hard things.

Dr. Andrew Huberman, a renowned neuroscientist, brings to light a brain-changing revelation: engaging in activities you'd rather avoid not only beefs up your mental grit but also enlarges a key brain area, the anterior midcingulate cortex (aMCC).

The aMCC is your brain's command center for resilience and tenacity. 

When you push through tasks you don’t wanna do, this part of the brain actually grows. 

This growth is linked to longevity and mental clarity in later life, as seen in 'superagers' – spry 70 to 80-year-olds with mental faculties matching or outperforming their 50-year-old selves.

So, how can you start expanding your AMCC today? Here's your action plan:

  • Embrace Discomfort: Seek out tasks that make you groan internally. If you despise running, lace up those shoes. Not a fan of cold showers? Turn that knob to chilly and dive in. Your brain will thank you later.

  • Mix It Up: Variety is key. Constantly rotate the activities you're less fond of. Variety ensures you're continuously challenging different facets of your resilience.

  • Make It Routine: Incorporate these 'unpleasant' tasks into your daily or weekly routines. Consistency is crucial for sustained AMCC growth.

  • Mind Over Matter: Remember, it's not about the task itself; it's about your reaction to it. Cultivate a mindset that sees these challenges as opportunities for growth.

  • Celebrate the Small Wins: Each time you conquer a dreaded task, give yourself a mental (or literal) pat on the back. It's not just about enduring discomfort; it's about recognizing your growth.

By willingly stepping into discomfort, you're not just enduring a temporary annoyance. You're sculpting a brain that's primed for a longer, sharper, and more vibrant life. 

So next time you're facing a task you'd rather skip, remember: it's not just a chore, it's a brain booster!

Here’s the kooky story of why the barn at Idyllwild Woods Retreat Center is positioned… oddly.

Update: We’re still waiting for our house to sell in AL so we can move into our oddly-positioned barn in the Smokies. 

When we finally move, it’s full-steam ahead. Thinking we might host some workshops on stuff like permaculture, homesteading, and eco-friendly building. Hands-on stuff. If you’d enjoy that kind of thing, hit REPLY and let me know what you’d like to learn.


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