The Happy Hustle Podcast

Have you ever hit a big goal, looked around, and wondered why it didn’t feel the way you thought it would? I know that feeling well. You can have an eight figure business and a two figure quality of life. I’ve seen it in people who make millions but have zero freedom, zero joy, and no idea when they last felt truly at peace. Honestly, for a while, that person was me. In this episode of The Happy H...

Have you ever crushed it at work all day, walked through your front door, and realized you had nothing left for the people you love most? I’ve been there. More times than I’d like to admit. You win in business, you lose at home, and somehow you still call it success. That’s not happy hustlin’, my friend. And that’s exactly why this conversation hit me so hard. In this episode of The Happy Hustle P...

Do you have a dream that still feels a little too big to say out loud? Seven years ago, mine was a room full of couples in red flannels, sitting in a U shape by the river with the Montana mountains behind them. This past weekend, that dream became real. Sixty people. Thirty couples. All high performing entrepreneurs, all in Big Sky for our very first Montana Mastermind couples retreat. And honestl...

Ever walk through your own front door and realize you're not really there? Your body's home. Your phone's in your hand. Your mind's still out closing the next deal. I've been there, and I'd bet a lot of you have too. That's exactly why this conversation hit me so hard. In this episode of The Happy Hustle Podcast, I sit down with my friend Trent McMurtrey in his brand new studio right here in Bozem...

Have you ever been so deep in the day to day grind of building your business that you forgot why you started in the first place? It happens fast. You’re chasing goals, answering messages, working on the next project, and trying to grow. Before you know it, your business is getting more of you than your health, family, relationships, and the life you’re actually trying to create. In this special ep...

Be honest with me for a second. If someone asked you right now what your retirement plan is, what would you say? If your gut answer is "Well, I'll sell the business someday," you're in good company. Most of us entrepreneurs are so locked in on the vision that the money side gets pushed to "later." I get it. Some days I just want to keep serving people and not even look at my bank account. But here...

Are you optimizing everything in your business except the one asset that runs the whole show, you? Your sales funnel, your KPIs, your team, your marketing spend, all dialed in. But your sleep, your energy, your blood work? Yeah, probably not so much. In this solo episode of The Happy Hustle Podcast, Cary Jack breaks down five ways to optimize your body and your mind so you can actually show up as...

Have you ever hit a number in your bank account you used to only dream about, and it still didn't feel like enough? Like the more you make, the more you worry? I've been there, and so has my guest this week. She's built an eight figure business, and she'll tell you straight up that money without peace is just a fancier kind of stress. In this episode of The Happy Hustle Podcast, I sit down with Ti...

There's a version of success that looks amazing on paper and feels completely empty on the inside. I know because I've talked to a lot of entrepreneurs who chased the number first and the meaning second, and most of them will tell you they got it backwards. This episode is a gut check on that exact thing, recorded on one of our favorite hiking pods out here in Montana. In this episode of The Happy...

What if the thing you've been told your whole life, save for retirement, max out your 401k, play it safe, is actually the exact thing keeping you from real wealth? That question sat with me long after this conversation ended, and I think it's going to sit with you too. In this episode of The Happy Hustle Podcast, I sit down with Matt Love, a husband, father of three, investor, and cash flow coach...

Ever notice how the version of you that quits would have it so much easier than the version that keeps showing up? Yeah, we've all felt that pull. This week on the Happy Hustle Podcast, we're getting honest about what it actually takes to stick with something when most people around you are bailing. In this episode of The Happy Hustle Podcast, I hike and pod during the Montana Mastermind with my b...

Have you ever felt amazing on paper, eating clean, hitting your macros, doing everything right, and still felt like something was off? That was the question that sent me down a rabbit hole with this week's guest, and honestly, it changed the way I look at my own kitchen. In this episode of The Happy Hustle Podcast, I sit down with Dr. Cate Shanahan, a Cornell trained physician scientist whose work...

When was the last time you actually graded your own life? Not your revenue, not your follower count, your actual life. Your marriage. Your mind. Your sense of purpose. Most of us never stop long enough to check. In this episode, I'm bringing you inside one of our Happy Hustle mastermind workshops, where I sat down with a room full of high performing entrepreneurs and walked them through something...

When was the last time you actually stopped and asked yourself how you're really doing? Not the autopilot answer you give people at the gym or in a group text. The real one. That's exactly where I took a room full of guys during a recent workshop, and it cracked something open for every single person in there, myself included. In this episode of The Happy Hustle Podcast, I'm sharing the Montana Ma...

Picture this. You're standing in the middle of untouched Montana wilderness, no cell service, no notifications, just you, a group of high level entrepreneurs, and whatever idea decides to show up in the silence. That's exactly where this conversation happened, and honestly, it's one of the reasons it hits different. In this episode of The Happy Hustle Podcast, I hike and pod during the Montana Mas...

Have you ever hit every single goal you set out for yourself and still felt completely empty inside? That's the exact moment I found myself in years ago, staring at a stack of investor paperwork worth millions, and I couldn't sign it. I was recently interviewed by Eric Berman on Inside The Speakeasy. It was a great experience! We discuss my journey from extreme burnout to creating a life centered...

Have you ever built something you love, poured years into it, and never once stopped to ask what it's actually worth? Most business owners haven't. And that one blind spot could cost them everything they worked for. In this episode of The Happy Hustle Podcast, I sit down with Michael Sauer also known as Bone, an exit planning expert who has helped guide business transactions up to a hundred and tw...

Have you ever caught yourself repeating a story about your life that, if you're really honest, isn't even true anymore? Maybe it's the "I had a perfect childhood" story, or the "I love my business" story, or the "I just don't know what I want to do" story. We tell ourselves these things so often we forget to check if they're real. That's exactly where this conversation with Philip McKernan took me...

Have you ever posted something that felt too messy, too unfiltered, almost embarrassing to hit share on, and then watched it outperform every polished piece of content you've ever made? Yeah, me too. And it happens more than you'd think. In this solo episode of The Happy Hustle Podcast, I'm breaking down something I've been calling the polished paradox, and why the more perfect your content looks,...

Have you ever hit every goal on paper and still felt like something inside you was falling apart? That's the question at the heart of this episode, and honestly, it's one I think about a lot as an entrepreneur myself. In this episode of The Happy Hustle Podcast, I sit down with Justin Roethlingshofer, a human performance expert, data driven health strategist, and longevity practitioner with over t...

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...

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 dow...

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 sh...

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 member...

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 ad...