The Happy Hustle Podcast

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...

Ever feel like you’re busy all day but still not getting the things done that actually move your life forward?

You’re checking boxes, replying to emails, juggling a million tabs in your brain… but at the end of the day, it feels like you just spun your wheels. If that sounds familiar, this episode is going to hit home.

In this conversation, I sit down with Bridget Hom, founder of Bridge to Freedom Coaching and co-owner of The Axiom Group. Bridget is a best-selling author, speaker, and business strategist who helps entrepreneurs and organi...

Ever wake up groggy even after what should have been a full night of sleep. Your alarm goes off, your brain feels foggy, and the day already feels harder than it should. Most entrepreneurs try to fix that feeling with more coffee, another supplement, or the next productivity hack. But what if the real issue is much simpler. What if the problem starts with where you sleep.

In this solo episode of The Happy Hustle Podcast, I talk about something most high performers overlook, sleep. I share why sleep is one of the most important investments you...

Ever feel like you are working harder than ever but still falling behind because technology keeps moving faster than you can keep up? A lot of entrepreneurs feel that way right now. Artificial intelligence is everywhere, automation is changing how businesses run, and it can either feel overwhelming or become the greatest advantage you ever leverage. In this episode we explore how to make it your advantage.

This conversation on The Happy Hustle Podcast features internet marketing pioneer Tom Antion. Tom is an internet multimillionaire, entrepreneur, speaker, and the host of the long running podcast Screw the...

Ever feel like you are working hard, checking the boxes, and doing everything you were told would lead to success… but something still feels slightly off?

Maybe your career is moving forward, your goals are progressing, and from the outside, everything looks great. Yet internally, you feel out of alignment. Perhaps your health has slipped, your relationships feel rushed, or you are simply hustlin' without happiness.

In this episode of The Happy Hustle Podcast, I share a powerful framework designed to help people reconnect ambition with well-being. Instead of chasing success that eventually leads to bu...

Ever had one of those moments where you step back from everything you have built and ask yourself a simple but uncomfortable question. What is all this actually for?

Many entrepreneurs chase success with relentless energy. Bigger revenue. Bigger teams. Bigger assets. Bigger everything. But eventually a deeper question surfaces. If you already have enough, what keeps you going?

In this episode of The Happy Hustle Podcast, I sit down with entrepreneur and outdoorsman Peter Goodwin for a raw and honest conversation about success, identity, and building a life that actually means something. Peter shares...

Ever feel like you’re doing all the “right” things like working hard, chasing goals, consuming content… but something still feels off? Like you’re busy, but not necessarily fulfilled? That gap between success and satisfaction is exactly what this episode is all about.

In this solo episode of The Happy Hustle Podcast, I break down what it really means to grow, not just grind. I dive into key areas of life that often get overlooked by high performers, including personal development, passionate hobbies, impactful work, and nature connection. This episode matters because it is not about doing more...

Ever feel like life is moving so fast you barely know yourself anymore? That was me last week, scrolling through emails, thinking about my next move, and realizing I haven’t hit pause to really check in with my own gut in ages. That’s exactly why I was so pumped to sit down with Julie Reisler on The Happy Hustle Podcast. If you’re a high performer trying to navigate success without losing yourself, this conversation is gold.

Julie is a HeartLed Intuitive Guide, two-time Tech-X speaker, host of the USU podcast, board-certified master coach, faculty member...

Have you ever hit a big milestone and still felt… off?

You closed the deal. You reached the revenue goal. You hit the number you’ve been chasing. On paper, everything looks solid. But internally? Something feels slightly empty.

In this episode of the Happy Hustle Podcast, I dive into three of the ten alignments from our S.O.U.L.M.A.P.P.I.N system — the framework I use to systematically harmonize ambition and well-being.

Those three are:

Loving Relationships
Mindful Spirituality
Abundance Financially

These...

Ever have one of those moments where everything looks great on the outside, but you suddenly realize you have not thought much about protecting the life you are working so hard to build? You are chasing big dreams, scaling the business, taking care of your family, and then it hits you. What about safety? What about awareness? What about being proactive instead of scrambling when something goes wrong?

In this episode of the Happy Hustle Podcast, I chat with Michael Julian, a third-generation private investigator and the CEO of National Business Investigations. Michael began his journey into...

Have you ever stopped to ask yourself if your hustle is truly aligned with the life you want to live? Maybe you’re grinding, hitting your goals, but still feeling off balance or a little drained. That’s exactly what we dig into on this episode of The Happy Hustle Podcast. I talk about energy, alignment, and selfless service—practical ways to optimize your life while giving back meaningfully to others.

In this episode, I break down my E.N.E.R.G.Y. framework, the pillars I use to stay at my best physically and mentally: Exerci...

Ever catch yourself thinking, “I’m doing all the right things… so why do I still feel tired, foggy, or just off?” You’re working out, trying to eat better, squeezing in sleep where you can, and yet your energy and longevity still feel like a question mark. If that sounds familiar, this episode of The Happy Hustle Podcast is going to land right where you need it.

In this episode, I sit down with Dr. Joy Kong, a UCLA-trained, triple board-certified anti-aging physician, stem cell specialist, educator, and CEO. Dr. Joy is the founder of Chara Health and...

If you’ve ever felt like you’re building something big but still wondering how to stay aligned, avoid burnout, and actually enjoy the journey… this episode is for you.

In this solo episode of The Happy Hustle Podcast, I’m pulling back the curtain and walking you through the real resources, tools, and experiences that can help you systematically harmonize ambition and wellbeing. From the Happy Hustle Book 2.0 and the Blissful Balancer to masterminds, community, and the deeper philosophy behind Happy Hustlin', this episode is all about giving you practical ways to create a life and business...

What if the reason you feel stuck, triggered, or disconnected isn’t your workload—but unhealed emotional patterns running in the background?

In this episode of The Happy Hustle Podcast, Cary Jack sits down with Tania Khazaal, transformational coach, emotional healing expert, and founder of Holistic Empowerment, for a powerful conversation on emotional healing, family dynamics, and why unresolved wounds quietly shape how we show up in life, relationships, and business.

Tania has helped thousands heal emotional estrangement, repair broken family connections, and break free from subconscious patterns rooted in childhood. Recently featured on Oprah, she...

Welcome to the audiobook edition of The Happy Hustle Book 2.0 — a practical guide for high-performing entrepreneurs who want success without sacrificing their health, relationships, or happiness.

This updated 2.0 version goes deeper into what it really means to build a life and business that feels aligned, intentional, and sustainable. Inside, you’ll learn how to:

• Redefine success beyond money and hustle
• Create systems that support both ambition and wellbeing
• Avoid burnout while still playing at a high level
• Build a life that feels good now, not “someday”

Whether you’re an entrepreneur, crea...

Ever feel like you’re doing all the “right” things in your business, posting consistently, running ads, chasing leads yet growth still feels heavier than it should? I’ve been there. For a long time, I thought the secret to scaling was always out there… more eyeballs, more followers, more people in the funnel. But what actually changed everything for me wasn’t before the sale. It was what happened after.

In this solo episode of The Happy Hustle Podcast, I break down what I call the 4R Growth Flywheel, a simple but powerful framework that’s helped us incr...

What if the real reason your relationship feels off has nothing to do with love and everything to do with how you handle conflict?

In this episode of The Happy Hustle Podcast, I sat down with my brother Jayson Gaddis for one of the realest conversations I’ve had about relationships, conflict, masculinity, and what it actually takes to build a thriving partnership while still chasing big dreams. Jayson is the founder of The Relationship School, a Wall Street Journal bestselling author of Getting to Zero, a husband, a father, and a former licensed psychotherapist who has sp...

Ever feel like you’re doing everything right on the outside… but something internally feels a little off? Like you’re winning on paper, yet fulfillment is somehow slipping through the cracks?

In this episode of The Happy Hustle Podcast, I’m bringing you a powerful solo conversation sparked by my good friend Ben Wilson, a real estate mogul from Nashville who recently dropped five simple yet game-changing questions in the Happy Hustle Club. And let me tell you… these questions aren’t just thought exercises. They are trajectory changers if you actually take the time to sit with the...

If you’ve ever felt like you’re doing all the “right” things, building the business, checking the boxes, hitting the milestones, but still feel restless, exhausted, or disconnected… this episode is going to land right in your chest.

In this episode of The Happy Hustle Podcast, I sit down with Dr. Barbara Eaton, and let me tell you, this conversation goes way beyond business strategy. Dr. Barbara is a highly sought-after transformational coach, female business strategist, keynote speaker, and the founder of a neuroscience-based coaching practice that helps purpose-driven entrepreneurs build thriving businesses without sacrificing peace, presence...

Winning on paper but feeling cooked on the inside? Yeah… I’ve been there.

In this episode of The Happy Hustle Podcast, I’m breaking down what I call the Burnout Audit — five sneaky signs you’re quietly burning out even if your business is growing, your calendar is full, and everyone thinks you’re “crushing it.”

Because here’s the truth: burnout doesn’t always look like a breakdown. Sometimes it looks like success… with a stressed-out nervous system.

And if you’ve been feeling tired, disconnected, reactive, or like you can’t fully enjoy the life you...

Ever felt like you're not living your true self?

In this episode of the Happy Hustle Podcast, I sit down with Graham Cochrane – a seven-figure entrepreneur, TEDx and keynote speaker, bestselling author, and the mastermind behind the globally acclaimed Graham Cochrane Show. With over 14 years of online coaching experience and 700,000+ YouTube subscribers, Graham’s insights are a goldmine for anyone looking to create more money, margin, and meaning in their lives.

Graham shares profound insights from his new book "Rebel," exploring how dreams are like giant clues revealing our true values. He discusses how to reso...

Deleting social media should’ve tanked my income…, but instead it helped me skyrocket it.

And I’m not saying that to be dramatic, I’m saying it because I didn’t realize how much my phone was quietly stealing from me until I took my power back.

In this episode of The Happy Hustle Podcast, I’m breaking down exactly why I deleted social media from my phone, what happened in my brain when I did it, and why it might be the single best “business move” you make all year — even if you’re a personal brand...

Most entrepreneurs are crushing it on paper… but quietly starving for connection behind the scenes.

And that’s exactly why I’m so fired up about today’s episode of The Happy Hustle Podcast, because I’m sitting down with my brother Stefanos Sifandos for a real, raw, and deeply powerful conversation about relationships, masculinity, healing, and what it actually takes to feel “turned on” by your life again.

Stefanos is the kind of guy who doesn’t just talk about connection, he lives it. He’s a husband, a father, an international speaker, and a transformational...

January doesn’t fail people, pressure does, and that’s exactly why most New Year’s resolutions crash and burn before February even hits. I’ve seen the stats, lived the cycle, and learned the lesson the hard way: January is not for domination, it’s for direction.

In this episode of The Happy Hustle Podcast, I’m breaking down how to build real momentum in the new year using a stupid-simple framework called C.A.L.M and why slow, aligned starts beat all-out sprints every single time.

Here’s the reality: nearly 80% of people quit th...

Ever wondered how some businesses skyrocket to success while others seem to spin their wheels endlessly?

In our latest episode of the Happy Hustle Podcast, we dive deep into the world of flywheels with Nathan Barry, the mastermind behind ConvertKit. With a SaaS empire generating over $40 million per year, Nathan spills the beans on how he keeps the wheels turning smoothly in his business and how you can do the same.

Nathan is not just your typical entrepreneur; he's a designer, writer, podcaster, father, husband, soon-to-be airplane pilot, and of course, a Happy Hustler.

Reflection is the cheat code most people skip, and it’s the very thing that turns a good year into a great life. Before charging into 2026 with more goals, more pressure, and more noise, I wanted to pause, look back, and extract the lessons that actually mattered. Because progress doesn’t come from moving faster, it comes from moving forward with clarity.

In this episode of The Happy Hustle Podcast, I’m breaking down 25 Terrific Takeaways from 2025, all through the lens of our S.O.U.L.M.A.P.P.I.N framework, the 10 alignments that help y...

I walked away from a seven-figure deal—and it changed everything.

In this episode of The Happy Hustle Podcast, I’m resharing my interview on The InPowered Life Podcast with my friend Rudi Riekstins and it’s one of those conversations that cuts straight to the truth about success, fulfillment, and alignment.

We dive into the pivotal moment when I chose to walk away from a seven-figure tech opportunity after realizing that external achievement without internal alignment leads to burnout and emptiness. On paper, everything looked like a win—but internally, something felt off. That decision...

Are you ready to stop whining and start winning?

In this episode of The Happy Hustle Podcast, we’re diving deep into why whining is holding you back, and how optimism is the key to creating your dream reality. If you want to learn how to reframe your mindset, boost your chances of success, and hear my personal mantra for overcoming adversity, this episode is for you!

As an entrepreneur, you know the odds are stacked against you. So how do you keep pushing forward when it feels like the deck is always against you?

There’s a moment every entrepreneur hits where working harder stops working and the answer isn’t more hustle, more ads, or more leads. It’s realizing that real growth comes from serving better, not shouting louder. That’s exactly where this conversation with Brett Fairall landed for me, and it’s why I couldn’t wait to share it with you.

In this episode of The Happy Hustle Podcast, I sit down with Brett Fairall, the creator and visionary behind Warehouse Bob, an AI-powered commerce engine that helps brands convert more, communicate better, and scale without chaos. Brett...

Most people don’t fail because they lack motivation or ambition. They fail because they’re trying to win the year with willpower instead of systems.

Setting big goals, feeling fired up in January, and then wondering by February why the momentum disappeared. What finally changed everything for me wasn’t more goals. It was one habit. Then another. And suddenly, success stopped feeling forced and started feeling inevitable.

In this solo episode of The Happy Hustle Podcast, I break down why habits beat goals every single time and how you can use two specific habits...

Have you ever looked successful on paper… yet felt like something was quietly off behind the scenes?

Like you were winning the game, but not really winning at life? That’s exactly the tension we unpack in this episode and trust me, it goes way deeper than money or business tactics.

In this episode of The Happy Hustle Podcast, I sit down with my good friend Ben Wilson for a real, grounded, no-BS conversation about wealth, legacy, faith, and what it actually means to live a life that feels aligned. Ben is the Owner and Brok...

Have you ever had that moment where you’re hustling hard, income is flowing, business is booming… yet deep down you still don’t feel financially free?

In this episode of The Happy Hustle Podcast, I’m breaking down the simple, powerful financial freedom formula that finally helped me understand what true abundance actually looks like and how to calculate it without stress, confusion, or overwhelm.

This episode isn’t about hype, Lambos, or flexing revenue screenshots. It’s about learning the exact numbers used by some of the world’s smartest investors and high-performance entrepreneurs...

Want to work less and make more?

In this episode of the Happy Hustle Podcast, I'm thrilled to introduce you to the one and only James Schramko, a remarkable Australian serial entrepreneur who's not just hustling but thriving and surfing the waves of success—both in business and life.

James was once trapped in the grind of overwork and stress but has transformed into the embodiment of a lifestyle entrepreneur who's crushing it. He's not just riding the waves of the ocean; he's riding the waves of entrepreneurship too.

With a track record of...

Have you ever noticed that one powerful weekend can shift the entire trajectory of your life?

That’s exactly what happened at the Optimized Life Mastermind I co-hosted at my brother Ben Greenfield’s biohacker compound in Idaho.

And in this episode of The Happy Hustle Podcast, I’m breaking down my biggest takeaways from that experience through the lens of what I call the 5 F’s: Family, Fitness, Faith, Finances, and Fun.

If you don’t already know Ben, he’s basically a walking encyclopedia of high-performance living. New York Times bestselling author, top...

Have you ever looked at your life, your business, your relationships, your health, and thought, “Man… I’m doing a lot, but am I actually living at my highest level?”

In this episode of The Happy Hustle Podcast, I sit down with Rudi Riekstins, a leadership visionary, energetic mastery coach, and trusted mentor to high-performing entrepreneurs and transformational leaders.

Rudi is the real deal. A husband, father, and deeply grounded human, he brings a blend of wisdom, spirituality, neuroscience, and lived experience that just hits different. This episode matters because it’s not about grinding harder… it...

Have you ever hit a birthday and thought, “Whoa… I learned a lot this year”?

In this special birthday episode of The Happy Hustle Podcast, I’m breaking down 36 life lessons from 36 trips around the sun, the real stuff, the hard-won wisdom, the wins, the mistakes, and the things that actually helped me put the Happy in my Hustle this past year.

Every year, I do this little tradition where I reflect back on the life truths that hit the hardest across all 10 Happy Hustle alignments. It’s not about being perfect. It’s about staying alig...