The Happy Hustle Podcast

Have you ever wondered why your side hustle still feels like a job, even after months of grinding on it? You're not lazy. You're not doing it wrong. You might just be building the wrong thing.

In this solo episode of The Happy Hustle Podcast, I get into something I've watched trip up side hustlers and seven and eight figure founders alike. It's not a money problem. It's not a hustle problem. It's an ownership problem. And once you see it, you can't unsee it.

Here's the big shift. Most people think a side hustle...

Ever feel like you're doing everything right in business, but something still feels off about the people teaching you how to do it? You're not crazy. And this episode is going to explain exactly why.

In this episode of The Happy Hustle Podcast, I sit down with Jordan Harbinger, host of The Jordan Harbinger Show, which has sat in Apple's top fifty podcasts for years and pulls in over 10 million downloads a month. Jordan spent years as a finance attorney before walking away to build one of the most respected interview podcasts out there. He's talked to...

Ever feel like you're winning on paper but losing everywhere else? Like your business is growing but you're not sure you'd recognize yourself in the mirror anymore? That's the trap I'm talking you out of in this episode, and it's one I lived through myself.

In this episode of The Happy Hustle Podcast, I get real about burnout, not as some soft, feel good topic, but as an actual business risk. I share how I lost my own joy, faith, fitness, and family time grinding away at my tech company in New York City, all in the...

What if your entire financial plan is really just hope and prayer dressed up to look like a strategy? That's the question that cracked this whole episode wide open, and once you hear the answer, you won't look at your bank account the same way again.

In this episode of The Happy Hustle Podcast, I'm sharing the Guest Guru Training that JP Newman delivered exclusively to our Happy Hustle Club members. And I'm telling you, this one needed to get out to everyone, not just the guys in the room that day. JP is a serial real...

Ever laid awake wondering if the business you've poured your heart into is going to get wiped out by a robot? Yeah, me too. And if you've felt that little knot of fear when another AI headline pops up on your feed, I want you to know you're not crazy and you're not alone.

In this solo episode of The Happy Hustle Podcast, I get real about the thing everyone's whispering about but nobody wants to admit out loud. Is AI going to take our jobs, our businesses, our relevance? I break down why the biggest threat...

Have you ever felt like you had to choose between being a good person and being good at business? Like every sale meant a little piece of your integrity had to go? Bob Burg is here to tell you that is a lie you have been sold, and it is time to let it go.

In this episode of The Happy Hustle Podcast, I sit down with Bob Burg, Co-Author of the International Bestseller The Go Giver and one of the most respected voices in the world of sales, influence, and business relationships. Bob has spent decades...

Have you ever stopped to ask yourself what you're actually carrying around every single day? Not your to do list. Not your inbox. The real weight. The stuff you don't talk about because you're too busy being the one everyone else leans on.

In this solo episode of The Happy Hustle Podcast, I'm getting real about something I don't think we talk about enough as entrepreneurs. We are some of the loneliest people on the planet. Everyone comes to us for answers. Everyone sees the wins. Nobody sees the pressure.

I just got back from...

What if the biggest bottleneck in your business isn't your team, your budget, or your idea, but simply the fact that you haven't asked AI the right question yet?

In this episode of The Happy Hustle Podcast, Michael Ballard closes out our AI Masterclass Workshop with maybe the most tactical, business first talk of the whole event. Michael is the founder of SlashDev, a software development agency that builds websites, mobile apps, CRMs, and lead generation systems for clients across a wide range of industries. He studied finance and entrepreneurship at the University of Washington, and back...

What if the smartest move you make with AI isn't learning it, but getting it to learn you?

In this episode of The Happy Hustle Podcast, Moses Mederos and Jason Yeh take the stage together during our AI Masterclass Workshop, and they hand the room something rare, a real system you can build today instead of another theory to file away. Moses and Jason are the founders of Scaling Freedom, and between the two of them they have spent over twenty years inside large tech companies watching software promise to do everything and then quietly asking businesses...

Have you ever built something for yourself that you were almost embarrassed to admit you needed? David Gonzalez did. And it changed how he sees himself entirely.

In this episode of The Happy Hustle Podcast, I sit down, well, I hand the mic over, to David Gonzalez during our AI Masterclass Workshop, and he delivers one of the most real, unfiltered breakdowns of agentic AI I have heard all year. David is the founder of Internet Marketing Party, a monthly founder room he has run since 2008 without missing a single month. Almost eighteen years in, he has...

Have you ever felt like you were walking through quicksand every single day in your business?

Like you were taking three steps forward and two steps back no matter how hard you worked? That was Tim Calise's life for years, and it might be yours right now too.

In this episode of The Happy Hustle Podcast, I brought in Tim Calise for our AI Masterclass Workshop during our Happy Hustle Club meeting, and I sat down to soak up everything he's learned about scaling with artificial intelligence. Tim's path has been anything but a straight...

Have you ever hit a goal you'd been chasing for years, and instead of feeling proud, you just felt panic?

That's exactly what happened to my guest today, and it kicks off one of the most honest conversations we've ever had on this show.

In this episode of The Happy Hustle Podcast, I sit down with JP Newman, an entrepreneur, investor, and the founder and chairman of Thrive FP. JP has spent over twenty five years in commercial real estate, closing more than two billion dollars in transactions across roughly twenty thousand apartment units, with...

Have you ever sat in a room full of people who admire you and still felt completely alone? If you're an entrepreneur chasing something big, there's a good chance you already know that feeling. You can have fifty thousand followers and not one person you'd actually call at two in the morning.

In this solo episode of The Happy Hustle Podcast, I get into something most people in the hustle world don't want to talk about. Loneliness. Not the casual kind, the kind that creeps in after years of grinding, sacrificing, and building something from nothing while...

What if the thing wrecking your relationship isn't a bad quarter or a failed deal, but the fact that you've gotten so good at building your empire you accidentally turned the people you love into roommates?

In this episode of The Happy Hustle Podcast, I sit down with Cody Jefferson, a man who is genuinely hard to put in a box. He's a husband, a father, a serial entrepreneur, a CMO, an advisor to some of the biggest names in entertainment and business, and the founder of 126 Brotherhood. But what you might not expect is that Cody...

You're exhausted, and you can't figure out why. You're using every AI tool in the book. You're getting more done than ever. But somehow you feel more scattered, more wired, and more burned out than before. Sound familiar?

In this solo episode of The Happy Hustle Podcast, I'm getting real about something I've been living firsthand, which is AI burnout. Not the kind of burnout that comes from grinding too hard without rest. This is something new. This is your brain being pushed past its limits while the tools around you keep accelerating. And I want to...

There's a version of success that looks great on a highlight reel and completely hollows you out from the inside. I've seen it. I've felt it. And in this episode, I sat down with a man who lived it hard, nearly paid for it with his life, and came out the other side with a completely different playbook.

In this episode of The Happy Hustle Podcast, I get to rock the mic with Cameron Herold, one of the most legendary operators in the entrepreneurial world. Cameron is the founder of the COO Alliance and the man known...

You ever look down at your phone and feel that weird mix of guilt and restlessness? Like you just spent 20 minutes scrolling and you're not even sure what you saw? Yeah. Me too. And I think it's time we talk about it honestly.

In this solo episode, I'm getting real about something that's been quietly stealing our joy, our focus, and our most important relationships. Your phone. More specifically, the way the attention economy has been designed to keep you hooked, anxious, and endlessly distracted. This isn't a tech bashing session. It's a wake-up call, and I'm...

What if the secret to a business that actually sets you free has nothing to do with your idea, your hustle, or your vision, and everything to do with a number most entrepreneurs never pay close enough attention to?

In this episode of The Happy Hustle Podcast, I sit down with Omar Zenhom, co-founder of the legendary $100 MBA Show podcast and the man behind Webinar Ninja, a SaaS company he built from zero to over 30,000 users and eventually sold in 2024. Omar is an educator turned entrepreneur, the kind of guy who left a decade of teaching to...

What if the wealthiest person in the room isn't the one with the biggest bank account? What if it's the one who can take a Tuesday lunch with their kid, go fly fishing mid-week, and fall asleep at night without anxiety eating them alive? Because I know people making five million a year who can't do any of that. And I know people making 120 grand who are living fuller, freer, and happier than most. So who's actually richer?

In this solo episode of The Happy Hustle Podcast, I break down what I call the Seven Freedoms Framework...

Have you ever felt like your head is a browser with 47 tabs open, none of them loading, and you can't figure out why you feel so scattered and behind even when you're working harder than ever? Yeah. This episode is going to hit you right where it counts.

In this episode of The Happy Hustle Podcast, I sit down with David Allen, the bestselling author of "Getting Things Done" and the creator of the GTD methodology that has genuinely changed how millions of people think about productivity. With over three million books sold across 30 plus countries, David...

Ever feel like no matter what you achieve, it's never quite enough? You hit the goal, get the thing, close the deal, and then almost immediately your brain moves the target again. You're not lazy. You're not ungrateful. You're just infected. And in this episode, we talk about exactly that.

In this solo episode of The Happy Hustle Podcast, I break down what I call the More Disease, the hedonic treadmill that keeps high achievers stuck in a cycle of wanting more money, more followers, more stuff, more achievements, without ever actually feeling fulfilled. This episode isn't...

What if the key to building something truly great wasn't perfect balance, but the courage to be temporarily out of it? That question hit me hard in this week's conversation, and I think it's going to hit you the same way.

This episode of the Happy Hustle Podcast is one of those conversations that just fires you up from start to finish. My guest is Tayson Whitaker, founder and president of Outdoor Vitals, a performance ultralight backpacking company he started at just 23 years old with $500 in his pocket and a whole lot of grit. Ten years later...

What if you could sit across from 10 of the most successful entrepreneurs alive, ask them one money question, and actually get a straight answer? No fluff, no sales pitch, just the real stuff. That's exactly what I did, and honestly, what came out of it might change the way you think about money forever.

This episode is a mashup of some of the most powerful financial wisdom I've ever collected on The Happy Hustle Podcast. Over time, I asked 10 incredible guests two simple questions. What does happy hustling mean to you? And what's your best money hack...

What if the most important thing you ever built wasn't a business? What if it was a blueprint, one that defines who you are, what you stand for, and how you show up for the people who matter most? That's the question this episode dares you to answer.

In this episode of The Happy Hustle Podcast, I'm resharing the Guest Guru Training that Rich Christiansen delivered exclusively to our Happy Hustle Club. And let me tell you, this one is too good to keep behind closed doors. Rich is a bestselling author, humanitarian, mentor, man of deep...

You ever wake up, look at your calendar, and feel that sinking feeling in your gut? That dread knowing you've got a call with someone you just... don't vibe with? Yeah. I've been there. And it took me longer than I'd like to admit realizing that feeling meant I hired wrong.

Here's the thing nobody tells you when you're building a business. You can have the best funnel, the cleanest offer, the most dialed-in content, and still feel completely miserable if you're surrounded by the wrong people. That's what this episode is all about.

In...

What if the book sitting on your nightstand right now could change the entire trajectory of your business, your confidence, and your life? Not in some theoretical way, but in a real, tangible, somebody-booked-a-one-way-ticket-to-Buenos-Aires kind of way. That's exactly what this episode is about.

In this conversation, I got to sit down with my good friend Nick Hutchison, bestselling author of "Rise of the Reader," keynote speaker, and founder of Book Thinkers, a company that helps authors promote and market their books so they actually get read. Nick built Book Thinkers from scratch after discovering the power...

When did you last go a full day without your phone? Not just setting it down for an hour, but actually powering it off, walking away, and not thinking about it once. If you're struggling to remember, this one's for you.

Most of us are running on fumes and don't even know it. The constant pings, the never-ending to-do lists, the back-to-back Zoom calls. It all adds up. And at some point, you stop asking "how do I get more done?" and start wondering "why do I feel so off?" The answer might not be a new...

What if every dollar you're already spending in your business could turn into first class flights and bucket list family trips, without touching after-tax money?

I sat down with Eli Facenda on The Happy Hustle Podcast, and this one hit different. Eli is the founder of Freedom Travel Systems, known online as "The Travel Guy." He's helped over 1,000 entrepreneurs turn everyday business expenses into 50K+ dream trips and first-class experiences, all through credit card points. The guy once booked a $6,000 business class flight for $6. That moment changed his life, and this episode might change how you think...

I want to ask you something real quick. What if you could wake up tomorrow and half your to-do list was already done? Emails answered, content posted, calls booked, follow-ups sent, and you did not lift a finger. That is not some far-off fantasy anymore. That is what is actually possible right.

In this solo episode, I am breaking down exactly how I am doing it and how you can too.
I am not here claiming to be the AI guru of anything. I am just the reporter. These are the things that are working in...

Have you ever felt like you were doing all the right things, checking all the boxes, growing the business, building the brand, showing up every day, and still felt like something was just off? Like there was this low hum of chaos underneath everything no matter how hard you worked? Yeah, me too. And that is exactly where this conversation starts.

In this episode, I sat down with one of my favorite humans on the planet, the one and only Rich Christiansen. Rich is a globally recognized thought leader, educator, mentor, and parallel entrepreneur who has co-founded 51...

You started your business to build a better life. Somewhere along the way, though, the business became your whole life. Sound familiar? Trust me, I've been there, and that's exactly why I wanted to have this conversation.

Here's the real question I want you to sit with. What if the reason, you're stuck right now isn't because you're not working hard enough, but because you're working too much the wrong way? Most entrepreneurs are convinced that grinding 24/7 is the path to success. But the data and real life say otherwise. Founders who get seven to eight hours...

You spend a third of your life in bed. Let that sink in for a second. A full third of your entire existence is spent lying on something most of us have never once thought twice about. I know I did not. I just bought a mattress, slept on it, and moved on. But what if the thing you are sleeping on every single night is quietly working against your health? That is exactly what this episode is all about.

In this conversation, I sat down with Tim Masters, founder of My Green Mattress, a company built...

Let me be real with you for a second. I used to be the guy saying "I don't have time to learn another tool." I said the same thing about social media back in 2012, and I paid for it. Every single time I waited, I left money, time, and momentum on the table. So when AI started picking up speed, I made a decision: I was going all in, not as some tech bro, but as a business owner who needed to do more with less and still get home for dinner.

In this solo episode, I...

Have you ever walked into a room and just felt it? That electric energy of being surrounded by people who get it, who push you, who see the same vision you do? That feeling is not an accident. It is proximity working its magic. And this week's guest has built an entire movement around that exact idea.

Eric Berman is a serial entrepreneur, investor, and marketing strategist who has spent decades mastering the art of building powerful communities. He is the founder of Speakeasy Mastermind, a fast growing global community of growth minded entrepreneurs focused on marketing...

Have you ever walked into a room and just felt it? That electric energy of being surrounded by people who get it, who push you, who see the same vision you do? That feeling is not an accident. It is proximity working its magic. And this week's guest has built an entire movement around that exact idea.

Eric Berman is a serial entrepreneur, investor, and marketing strategist who has spent decades mastering the art of building powerful communities. He is the founder of Speakeasy Mastermind, a fast growing global community of growth minded entrepreneurs focused on marketing...

Ever invest in something big, thinking it’s going to change everything… only to realize later the real value wasn’t what you expected?

That’s exactly what hit me after hosting our recent Montana Mastermind Ski Adventure. We had 30 high level, heart centered entrepreneurs come together for a few days of deep conversations, outdoor adventures, and serious growth. And while the experience was incredible, what stood out most were the simple truths that kept showing up again and again.

In this solo episode, I break down my five biggest takeaways from that mastermind. No fluff. J...

Have you ever poured years of your life into something, only to realize you've completely lost yourself in it? Yeah. Most entrepreneurs know that feeling way too well. And today's guest has lived it, learned from it, and built something pretty incredible on the other side of it.

In this episode of The Happy Hustle Podcast, I sit down with Nic De Castro, founder and CEO of LandTrust, a land sharing marketplace that connects hunters, anglers, and outdoor enthusiasts with private landowners across the country. Nic spent most of his twenties working in early-stage tech startups, living...

Ever feel like you're grinding so hard that your body just... breaks? Like you're doing all the right things on paper but still feel like garbage? Yeah. Eric Hinman's been there too. And he went from out-of-shape insurance salesman to five-time Ironman World Championship competitor. So it's safe to say he figured some things out along the way.

In this episode of The Happy Hustle Podcast, I'm resharing the Guest Guru Training that Eric Hinman delivered exclusively to our Happy Hustle Club. Eric is an endurance athlete, serial entrepreneur, investor, and content creator who's built an entire...

You ever have one of those moments where you’re surrounded by people, notifications blowing up your phone, group chats buzzing, social media lighting up… and yet somehow you still feel disconnected?

Yeah, same.
That’s exactly why this conversation hits different.

In this episode of The Happy Hustle Podcast, I sit down with Barb Betts, international keynote speaker, CEO, and author of The Relationship Advantage, to unpack what it really means to build authentic, meaningful relationships in a world that’s more connected than ever, yet somehow feels more disconnected too.

Barb has...

Ever feel like no matter how hard you hustle, your energy is draining faster than you can recharge? That’s what happens when you’re out of alignment. In this episode, we’re diving into the S.O.U.L.M.A.P.P.I.N. system and how checking your alignment every day can prevent burnout, boost focus, and help you reclaim control over your energy and productivity.

The discussion is all about practical ways to unplug from digital distractions, reset your mindset, and create a daily rhythm that keeps you aligned with your goals. You’ll learn...