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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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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** 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…
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** 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 …
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246 - The Future-Proof Creator (what still works in 2025?)
47:41
47:41
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** 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 cha…
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** 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 wi…
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244 - Back on Instagram after 3 years: Month 1 recap + Month 2 plan
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58:12
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** 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 …
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243 - How we’re (currently) prepping/planning our parental leave
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50:40
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** 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 intent…
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242 - Why we're ending WAIM Unlimited (part 2)
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41:16
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** 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 qu…
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Minisode (Jason Only) - Does everything feel messy right now?
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13:01
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** 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
45:14
45:14
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** 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 w…
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240 - Why we’re ending WAIM Unlimited (part 1)
53:49
53:49
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** 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 m…
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239 - Spring 2025 Launch Recap (lower sales, big lessons, and future shifts)
59:54
59:54
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** 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 brea…
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238 - We’re having a baby! 😱 (Fertility journey update)
1:01:02
1:01:02
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** 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!…
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237 - 4 steps to make your next launch feel CALM
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46:00
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** 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 ef…
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236 - Business is overcoming these 6 roadblocks
58:56
58:56
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** 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 grip…
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235 - 7 changes in online biz you shouldn’t ignore
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48:45
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** 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 w…
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234 - We built an accountability app with NO CODE!
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51:58
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** 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 commu…
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233 - Is NOW the right time to diversify?
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38:14
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** 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 bask…
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** 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 “c…
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231 - Invent a new social media app? (and other Qs!)
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44:07
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** If we could create an entirely new social media app, what would we do? Do creators have a responsibility to share their failures? What are our biggest business risks we’ve taken? These q…
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230 - The BEST tool we've used in years!
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1:08:41
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** Today we’re excited to share what we feel is the biggest game-changing AI tool since OpenAI released GPT a few years ago. We’ll talk about why this tool has consumed all our free time an…
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** We don’t normally do prediction episodes, but this year we thought it would be fun! At the end of 2025 we can look back and see how right/wrong we were (spoiler alert: we will probably b…
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228 - Our 2024 review and 2025 preview
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1:21:34
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** 2024 is in the rear view mirror and we have an episode reviewing what went well, what didn’t go well, and our look ahead at 2025! We love doing these reviews and hope you enjoy hearing a…
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227 - How'd our first Black Friday deal in 7 years go?
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47:35
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** It’s hard to believe we haven’t sold anything on Black Friday/Cyber Monday in 7 years! But, this year it made sense for us and we break down why and how things went. We cover: What we so…
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226 - A (real) messy convo about social media
1:21:13
1:21:13
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** We went back and forth on sharing this episode, as it’s one of our more “real” and honest conversations. While we love sharing polished thoughts with you all, our relationship with using…
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225 - Top 5 marketing tactics to use in 2025 (draft style + Thanksgiving!)
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54:17
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⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist ** When this episode goes live it’s Thanksgiving in the U.S. and we’re drafting our Top 5 dishes we’d want on our plates. We keep the draft fun going by also drafting our Top 5 marketing ta…
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