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Jason Zook Podcasts

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We’re Jason and Caroline Zook, a husband and wife team running two businesses together and trying to live out our version of a good life in the process. In this business podcast, we share with you our lessons learned about how to run a calm, sustainable business—one that is predictable, profitable AND peaceful. Join us every Thursday if you’re an online creator who wants to reach your goals without sacrificing your well-being in the process.
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Move The Needle

Greg Hartle and Jason Zook

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Follow along as Greg Hartle and Jason Zook, two serial entrepreneurs, transparently discuss which real-time actions move the needle in their respective small businesses and which fall short.
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Follow the journey as Jason Zook, founder of IWearYourShirt, BuyMyLastName, and BuyMyFuture, writes his next nonfiction book publicly on watchmewrite.co. Can Jason finish writing the first draft of his second book in just two weeks? Tune in to find out!
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BuyMyFuture

Jason Zook

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A short daily podcast that tracks the progress of Jason Zook's latest project BuyMyFuture. BuyMyFuture is the opportunity to buy an entrepreneur's life work for $1,500. If you want to create more, sell more, and teach more, then buying Jason's future is right for you.
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Invisible Office Hours

Paul Jarvis and Jason Zook host a seasonal podcast for entrepreneurs and creative professionals who aren't confined to literal office hours. They also talk about vampires and zombies sometimes.

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Invisible Office Hours is a seasonal podcast for people that aren't confined to a literal office or that aren't confined by conventional thinking. Hosted by Jason Zook and Paul Jarvis the show covers a wide range of topics that all touch on aligning your thinking with your journey, and dealing with the bumps along the way. Topics include criticism, selling out, positivity and we release new episodes Netflix-style throughout the year.
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Ready to chase that dream? Want to quit your 9-5 job? Just need a little nudge to get you into creation mode? The Action Army podcast helps entrepreneurs, small business owners, creative people, and anyone else who wants to take more action in their lives and businesses. Jason Zook is the host of the show and is best known for his entrepreneurial antics with IWearYourShirt, BuyMyLastName, SponsorMyBook, and BuyMyFuture. Jason shares a weekly topic and highlights the success of someone in the ...
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Sleeping With The Boss

Jason Zook and Caroline Winegeart host Sleeping With The Boss, a relationship show about living together, working together, and loving together.

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Sleeping With The Boss is a weekly show about relationships, work life balance, and entrepreneurship. Hosted by a couple that live, work, and sleep together - Jason Zook and Caroline Winegeart.
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Mistakes That Made Me is the podcast that asks extraordinary business owners to share their biggest business mistake – so you know what NOT to do on your road to success. Join Eman Ismail as she chats to some of the smartest minds in business about how to push through failure and accept it as an important and necessary part of building a business. Because it turns out: your biggest business mistake often leads to your biggest lesson and then your biggest blessing.
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In this episode, we’re answering a handful of questions about our pregnancy journey so far (36 weeks as of recording!) We talk about everything from favorite (and least favorite) parts, to how Jason’s been helping, to what’s surprised us most along the way. We also chatted about: How we’ve prepared financially for baby What it’s been like stepping …
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This is one of the most honest, detailed conversations I’ve had about what it really looked like to evolve from a solo email strategist to building a micro-agency. (Originally published on the Confessions with Jess and Cindy podcast). Jess, Cindy, and I talk about: Why I don’t want employees (at least for now), and how I intentionally built a team …
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We just wrapped our last-ever launch of WAIM Unlimited. All while 7 months pregnant, grieving the loss of two family members, troubleshooting a broken-down car, a 5-hour medical snafu, and somehow still exceeding our high goal for our launch. Let’s break it all down. In this episode, we’re going to cover: What actually worked (and didn’t) across em…
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Today’s episode is a little different because the mic’s turned on me. This conversation was originally recorded for Sonia Thompson’s Inclusion and Marketing podcast, and it was such an important one, I wanted to share it with you here too. Sonia and I talk about what it really means to plan inclusive business events – especially for people who iden…
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This is part three of our 3-part series sharing the real-time updates of our LAST-EVER launch of our un-boring coaching program WAIM Unlimited. As of recording this FINAL installment, we have just 12 hours left in the launch 😱. You’ll get an update on our total sales numbers, what went on the last week (another death in our family 💔), and the final…
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Since we've been running WAIM, certain questions come up over and over. In this episode, we’re answering the top 10 things we hear most from creative business owners who feel stuck and don't know what to do next. We cover: How to increase sales without feeling pushy How to get clarity on what you're building and who it's for How to overcome fear an…
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This is part two of our 3-part series sharing the real-time updates of our LAST-EVER launch of our un-boring coaching program WAIM Unlimited. As of recording this second installment, we are 1 WEEK post-launch and have 1 week to go! (This is the "Sahara Desert" part of the launch.) You’ll get an update on our total sales numbers, how our boosted IG …
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Getting fired hurts. But getting fired for the thing you’re actually an expert at is another level of pain. My guest is Claire Pelletreau, conversion expert and host of the Get Paid Podcast. (This is an Oldie But Goodie epsiode!) In this episode, Claire shares the painful moment when she was fired for making a huge mistake in her job. She explains …
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With AI rapidly multiplying the amount of content flooding every platform (40m vertical videos PER DAY 😬), we’re facing an era where information is no longer scarce... it’s commoditized. So what actually becomes more valuable in a world drowning in content? In this episode, we share the three human skills we’re doubling down on in the year ahead. T…
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If you love hearing the behind the scenes of a product launch, then you are going to thoroughly enjoy this 3-part series for our LAST-EVER launch of our un-boring coaching program WAIM Unlimited. As of recording this first installment, we are 24 hours post-launch and have 2 weeks to go! You’ll get to hear how our pre-launch waitlist went, where 44%…
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If you’ve ever felt like you’re already behind in the world of AI (or like you need to try every new tool just to keep up) you’re not alone! In this episode, we introduce the idea of slow-learning AI: a calm, intentional approach to staying curious without getting overwhelmed. We share specific strategies we’re using to create boundaries, focus our…
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Today, Steve's answering questions about – When a podcaster can take the leap and build a paid product/service The calling yourself a 'freelancer' vs 'business owner' debate Steve's process around subcontracting and hiring other freelancers to work on projects with him Links: Get the transcript here Listen to Steve's Mistakes That Made Me interview…
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Are digital product launches dead? Not at all! But in 8 years, we’ve noticed a few changes and we wanted to share what we’ve seen firsthand. How many sales emails matter? Do you actually need launch bonuses? Is there value in using AI to write sales page copy or does it sound too… AI? Here’s what we cover in this ep: Why pre-marketing matters more …
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We are many months away from 2026 and the big shift in our Wandering Aimfully business, but we wanted to pull back the curtain and share how we ideate business ideas BEFORE they see the light of day. This episode, we hope you get to hear how we brainstorm, how we go back and forth, and when we get excited (or not) about a potential new idea. In 202…
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When Steve Folland’s *only* client let him go, he’d just quit his full-time job to go all in on his audio and video editing business. Being jobless and clientless couldn’t have come at a worse time. Steve’s wife had just gone on maternity leave and they had a brand new (4-month-old) baby – plus an older child too! In this Oldie But Goodie convo, St…
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With AI taking off like wildfire, algorithms shifting like crazy, and tactics expiring faster than ever… what actually still works in 2025? In this episode, we’re cutting through the chaos to ground you in what remains true in online business today. If you feel like you're fighting a current right now, you're not alone! We cover... The three founda…
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If you’re like us and using GPT (or Claude, etc) on a daily basis, then you have an AI that is gaining context about you constantly. With that in mind, we decided to ask AI to come up with questions they thought would be compelling for us to answer! In this episode, we have two AI Speakers joining us to ask us questions about our businesses, conten…
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This might be my favourite episode of Mistakes That Made Me 😍 (An oldie but goodie!) Caroline and Jason Zook are two creatives who are full of ideas. They’re the founders of Wandering Aimfully – the UN-boring coaching program for intentional online business owners – and Teachery: a software platform for creating and hosting online courses. After mo…
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We’re one month into our return to Instagram after a 3-year break, and in this episode, we’re pulling back the curtain on what’s working, what’s not, and how we’re approaching Instagram in a way that actually feels good (and sustainable). Spoiler: we’re not here to growth-hack, we’re here to experiment, stay aligned with our business, and TRY to en…
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With just a few months to go before our Tiny Zook 🐣 arrives (!), we’re sharing how we’re approaching parental leave—not as a step-by-step guide, but as a real-time snapshot of our intentions, plans, and mindset. Whether you’re expecting, planning a business sabbatical, or just curious about building more space into your business, this one’s for you…
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It's my (33rd) birthday week! So, I'm re-sharing the super popular birthday episode I published last year for my 32nd birthday. (An oldie but goodie!) Tune in to hear me share 32 of my favourite (business and personal) things... from business hires, podcasts, software/tools to mentors to TV shows and more as I celebrate another trip around the sun …
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This is the second part of our discussion about retiring our WAIM Unlimited coaching program. We are going to do ONE final enrollment period in a few months and we answer some of your questions about this decision. The questions we answered in this ep: How are we feeling confident when it comes to the money side of this decision? Do we have savings…
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If you loved my first interview with Belinda Weaver back in 2022 (Going and Growing Too Slow), join us for this unedited extended interview (recorded in 2024) where we continue our conversation about growing your business slowly and intentionally. Links from this episode: Belinda Weaver Hot Copy podcast Get The Email Rules: Eman's FREE 35-minute em…
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How do you really know when it’s time to move on from an offer you’ve built your business around? In this episode, we’re sharing the four indicators that helped us make the decision to wind down WAIM Unlimited—insights we hope will help you reflect on your own path. We dive into: What it feels like to fall out of love with your offer (and why that’…
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After six incredible years, we’ve decided to retire our flagship program, WAIM Unlimited (after one FINAL upcoming launch). In this episode, we’re walking you through exactly why we’re making this sizable change. Retiring WAIM Unlimited didn’t come from burnout or panic… but from clarity, alignment, and a desire to move into our next chapter with i…
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This week, I'm on the Building Your Brand Podcast (hosted by Liz Mosley) discussing the ins and outs of email marketing. We explore how to create effective email strategies, why consistency is key, and how to infuse your newsletters with your unique voice. I share my journey from generalist to email expert and offer valuable advice on finding your …
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Our latest WAIM Unlimited launch was smaller than expected, but instead of panicking, we’re using it as a chance to adapt, experiment, and pivot. In this launch recap episode, we’re breaking down: The details of our Spring 2025 launch (amidst first trimester, new 6-month option, and our very minimal marketing effort) Why we think sales were lower t…
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This episode is a special one—because we’re pregnant! 🎉 We want to share our journey so far, from navigating fertility struggles to getting our positive test (on New Year’s Eve, no less!), and what the first trimester has been like for both of us. We’re covering: The fertility challenges we faced (Ep #223), including two pregnancy losses and the di…
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This episode goes out to anyone who has felt stressed during a launch! We want to help change that for you and we have 4 steps that ensure your launches are calm, profitable, and feel effortless. THE biggest mistake we see folks making when doing live launches is not enough planning and prep time (our own customer survey data showed 75% of people p…
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