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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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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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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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255 - Our Final WAIM Launch: The FULL Recap...
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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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254 - Real-time FINAL launch update (3 of 3, Jason only)
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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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253 - 10 most common questions we get asked
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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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252 - Real-time FINAL launch update (2 of 3, Jason only)
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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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251 - The 3 human skills you need to be building in an AI content world
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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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250 - Real-time FINAL launch update (1 of 3)
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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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249 - How we're learning AI tools without overwhelm
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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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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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246 - The Future-Proof Creator (what still works in 2025?)
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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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244 - Back on Instagram after 3 years: Month 1 recap + Month 2 plan
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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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243 - How we’re (currently) prepping/planning our parental leave
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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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242 - Why we're ending WAIM Unlimited (part 2)
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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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Minisode (Jason Only) - Does everything feel messy right now?
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See what we're up to: https://wanderingaimfully.com/now Try Teachery for free: https://teachery.coBy Wandering Aimfully
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241 - 5 signs it's time to pivot your business
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43:53
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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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240 - Why we’re ending WAIM Unlimited (part 1)
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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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239 - Spring 2025 Launch Recap (lower sales, big lessons, and future shifts)
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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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238 - We’re having a baby! 😱 (Fertility journey update)
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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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237 - 4 steps to make your next launch feel CALM
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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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236 - Business is overcoming these 6 roadblocks
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57:35
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Whether you’re JUST starting a business or you’re making a pivot, there are 6 roadblocks that likely get in your way. Are you stuck at just one of them or do all 6 have you in their grips right now? In this ep, we explore the thoughts that keep business owners from moving forward (especially early on). The 4 Qs we mentioned in the episode that ever…
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235 - 7 changes in online biz you shouldn’t ignore
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47:23
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When we started Wandering AImfully in 2018 the online business landscape was in a lot of ways the same, but in some ways VERY DIFFERENT. In this episode, we share 7 huge changes/shifts we’ve seen in the online business space. Some are obvious (🤖👀) and some have snuck up all of us. The most important takeaway: You can either fight the current of cha…
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234 - We built an accountability app with NO CODE!
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50:36
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If you can’t tell, we are pretty bullish on no-code tools right now and we’re excited to share this episode talking about how we built an accountability app/game for our membership community! We walk through why we think creating tools is an alternate marketing path instead of creating content for social media. While everyone is focusing on Reels, …
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233 - Is NOW the right time to diversify?
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36:53
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With all the hullabaloo around the TikTok ban, it’s got us thinking about the topic of diversifying your marketing versus focusing. Is it smart to put all your eggs in ONE marketing basket? How can you create safeguards for your business? We’ve been huge advocates of email list building for 10+ years and while social networks come and go, our email…
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Ahhhh, self-sabotage, otherwise known as overthinking or just unintentionally getting in our own way. We’re all guilty of it, but how can do it a bit less? Whether it’s hiding in your “creation cave” or avoiding sending sales emails so you don’t feel sleazy, there are a handful of ways we limit our business potential that are of our own doing (we k…
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