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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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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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TW: miscarriage, pregnancy loss, chemical pregnancy, infertility In this episode, we share our personal story of trying to conceive (TTC) earlier this year, which resulted in two very early miscarriages, also known as chemical pregnancies. Now that we’ve had some time to process, we wanted to give you more details about what's been going on behind-…
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SCHEDULE NOTE: We are on a break and our next episode will be released in mid/late November, 2024 👍. *** It’s time for a recap of our latest launch of WAIM Unlimited! We share the sales numbers, the lessons learned, and what changes we are/aren’t making for the next launch. Spoiler alert: For the second launch in a row, we did NOT hit our low goal …
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SCHEDULE NOTE: We are on a break and our next episode will be released in mid/late November, 2024 👍. *** Who wants to pull back the curtain and hear about a BIG experiment we ran with Teachery this summer? You do?? Then let’s dive into it! In this episode, we talk about a huge shift in direction for Teachery as a business. What might seem simple on…
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SCHEDULE NOTE: We are on a break and our next episode will be released in mid/late November, 2024 👍. *** If there’s ONE thing we believe makes every launch successful, it’s having a pre-launch strategy. Specifically, we like using a 4-week email lead-up series based around a few key themes. Over the past 10 years, we’ve used pre-marketing to get pe…
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SCHEDULE NOTE: We are on a break and our next episode will be released in mid/late November, 2024 👍. *** What if you didn’t have to use all the standard tactics and strategies to make millions of dollars selling digital products? We interviewed Michelle Rohr, founder of Secret OWL Society, to find out how she harnesses her intuition to sell courses…
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Is the future of digital products and selling information online moving towards Done-For-You? We believe so and we’ll share why and what we’re doing about it (and what you should do too!) In this episode, we talk about a big shift we’re seeing in customer behavior and how that impacts solopreneur creators. Having been in the online course industry …
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SCHEDULE NOTE: We are on a break and our next episode will be released in mid/late November, 2024 👍. *** We are doing something we’ve NEVER done before in 200+ episodes of our podcast… having a guest! We are excited to share this chat with our friend Wayne Fick, who, over the past two years, he transitioned from working with clients, having zero au…
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Evergreen sales are often painted as the ultimate dream: you fall asleep, wake up to sales, and money magically deposits into your account without lifting a finger. Sounds perfect, right? However, the reality of Evergreen is far from this idyllic picture… This week, we discuss selling digital products Evergreen vs Launches. While Evergreen is often…
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Since the beginning of the year, we’ve been on a mission to help more entrepreneurs build businesses that allow them to live a balanced life. We initially thought the key was giving our members one thing to focus on each month through our live coaching sessions. While this provided clarity, it also led to overwhelm as members felt they had to prior…
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Have you ever had a product launch flop? If you haven’t but want to avoid ever having a “floppy” launch 😅, this episode has four actionable tips for you. We know firsthand the excitement and hard work that goes into creating a digital product, but what happens when all that effort leads to disappointment? In this episode, we're sharing our personal…
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We’re creating our first new product in years and taking you along on the journey behind the scenes! The product is called Calm Launch Formula and it’s a done-for-you online course that helps you plan your next digital product launch using our proven system. What goes into creating a new product? How is this different than a standard online course?…
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SCHEDULE NOTE: We are on a break and our next episode will be released in mid/late November, 2024 👍. *** We officially created and posted our very first piece of social content for Teachery 😂. But… there were some mental hurdles when it came time to hit publish and we’re going to share how we worked through those. If you’ve been following along the…
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We are two months out from our next enrollment period for WAIM Unlimited and wanted to give you a behind the scenes look at everything on our to-do list pre-launch. This is our first enrollment period in over a year that includes a new program! We’re creating the “Calm Launch Formula,” a product to help you plan your own 2-week launch based on our …
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There is a ton of glamorization when it comes to having a “team” in the online business world. Having employees can be a badge of honor, but is hiring the right fit for you?? In this episode, we share our thoughts on keeping our “team” small and not going down the path of hiring more people. We’re not saying hiring people is bad, but for us, managi…
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SCHEDULE NOTE: We are on a break and our next episode will be released in mid/late November, 2024 👍. *** Is a CALM content creation plan possible? And can we do it for TWO businesses?? In this episode, we explore our content batching schedule and some of the processes we’re experimenting with this month. We’ve been on a break from consistently crea…
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After spending many years with an unfocused audience and nebulous problem we solve, we *THINK* we’ve finally landed on the right answer for our core business…. maybe? One thing we know for sure, we’ve always operated Wandering Aimfully as generalists. We can help with email marketing, copywriting, branding, etc. Sure, we were always trying to help …
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SCHEDULE NOTE: We are on a break and our next episode will be released in mid/late November, 2024 👍. *** Last week, we shared a plan of action from an SEO Expert we paid. It included writing articles, competitor pages, and a user-generated content strategy. How did we do with that plan? Tune in to find out! Writing informative articles is not our f…
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SCHEDULE NOTE: We are on a break and our next episode will be released in mid/late November, 2024 👍. *** Are SEO articles even relevant in 2024?? Well, we paid an SEO strategist to give us the answer and we’re going to share their plan of action in this episode. The report we got back from an SEO Strategist does confirm that keyword-based articles …
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SCHEDULE NOTE: We are on a break and our next episode will be released in mid/late November, 2024 👍. *** The second week of our 5-week content extravaganza has concluded! We worked on long-form videos for Teachery and learned a ton of lessons (and had to UN-LEARN some well-worn ideas and habits too). There has been ONE clear friction point for us o…
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Our 5-week content EXTRAVAGANZA is underway! We recap how our first week of creating short-form 60-second vertical videos went and give you a preview of what’s to come this week as we pivot to long-form YouTube content for Teachery. If you didn’t listen to last week’s episode, we’re embarking on a 5-week content journey to get back into the groove …
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SCHEDULE NOTE: We are on a break and our next episode will be released in mid/late November, 2024 👍. *** Here we go, folks! We’re back on the short-form video creation train and this week we’re sharing our plan of action for Teachery. We’ve been off social media for 2.5 years, so this is quite the journey! If you missed last week’s episode, we’re e…
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SCHEDULE NOTE: We are on a break and our next episode will be released in mid/late November, 2024 👍. *** Bring on the 5-week content EXTRAVAGANZAAAA! We are getting back in the content creation saddle for the first time in almost 3 years. We’ve only been creating “nurture” content for the entirety of our WAIM business and that’s about to change! Th…
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SCHEDULE NOTE: We are on a break and our next episode will be released in mid/late November, 2024 👍. *** We LOVE a launch recap episode! And as two people who value transparency and honesty in the online business world, we hope you appreciate this one because our latest launch (Spring 2024) didn’t quite hit the mark. Now, we want to be 100% clear: …
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SCHEDULE NOTE: We are on a break and our next episode will be released in mid/late November, 2024 👍. *** Join us this week as we celebrate episode #200 of this podcast by sharing a few untold (maybe just lesser known?) stories from our entrepreneurial pasts. We each picked a few stories for the other to share without telling them ahead of time — fu…
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SCHEDULE NOTE: We are on a break and our next episode will be released in mid/late November, 2024 👍. *** We’ve been working together in some capacity for almost 15 years! In that time, we’ve learned how to communicate, navigate each other’s emotions, but we still run into difficult moments like we did this week. In this episode, we want to share ou…
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