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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Caroline Zook Podcasts
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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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♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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 ac…
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♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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 se…
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246 - The Future-Proof Creator (what still works in 2025?)
47:12
47:12
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♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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 t…
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♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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…
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244 - Back on Instagram after 3 years: Month 1 recap + Month 2 plan
57:42
57:42
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57:42
♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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 Inst…
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243 - How we’re (currently) prepping/planning our parental leave
50:11
50:11
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50:11
♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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 …
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242 - Why we're ending WAIM Unlimited (part 2)
40:47
40:47
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40:47
♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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 y…
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Minisode (Jason Only) - Does everything feel messy right now?
12:31
12:31
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12:31
♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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
44:44
44:44
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44:44
♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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 decisio…
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240 - Why we’re ending WAIM Unlimited (part 1)
53:19
53:19
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53:19
♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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 w…
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239 - Spring 2025 Launch Recap (lower sales, big lessons, and future shifts)
59:24
59:24
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59:24
♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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’r…
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238 - We’re having a baby! 😱 (Fertility journey update)
1:00:32
1:00:32
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1:00:32
♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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…
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237 - 4 steps to make your next launch feel CALM
45:30
45:30
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45:30
♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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 f…
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236 - Business is overcoming these 6 roadblocks
58:27
58:27
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58:27
♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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 thei…
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235 - 7 changes in online biz you shouldn’t ignore
48:15
48:15
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48:15
♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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/sh…
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234 - We built an accountability app with NO CODE!
51:28
51:28
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51:28
♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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…
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233 - Is NOW the right time to diversify?
37:45
37:45
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37:45
♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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 marketin…
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♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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 y…
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231 - Invent a new social media app? (and other Qs!)
43:37
43:37
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43:37
♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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? T…
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230 - The BEST tool we've used in years!
1:08:11
1:08:11
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1:08:11
♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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 t…
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♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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 prob…
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228 - Our 2024 review and 2025 preview
1:21:04
1:21:04
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1:21:04
♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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 hea…
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227 - How'd our first Black Friday deal in 7 years go?
47:05
47:05
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47:05
♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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…
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226 - A (real) messy convo about social media
1:20:44
1:20:44
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♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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…
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225 - Top 5 marketing tactics to use in 2025 (draft style + Thanksgiving!)
53:47
53:47
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♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses 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 market…
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