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Before We Dive In Today…Happy Holidays!

Thought of the Week

In this Week’s Newsletter:

Up Front: Ownership Lessons the Hard Way: Don’t make these mistakes

This Week’s Biz Quiz: Will We Stump You This Time?

Strategic Thinking: How to Automate Your Customer Journeys

Need Help?: Help is On The Way!

UP FRONT: 

Ownership Lessons the Hard Way: Remote Year’s Shutdown

Remote Year, the OG darling of digital nomad programs, just bit the dust, leaving over 1,000 would-be travelers scrambling for refunds and answers. It’s a mess—vendors unpaid, customers out of pocket, and two CEOs pointing fingers like it’s a corporate soap opera.

But behind the drama is a cautionary tale every entrepreneur and business leader needs to hear: if you don’t control the game, you’re always at risk of losing it.

So, What Went Wrong?

Remote Year started strong in 2014, bundling travel, accommodations, coworking, and curated experiences. The dream was real, and people signed up in droves. But fast-forward a few years, and they made a crucial move: they sold the company.

First to Selina in 2022, and then (supposedly) to Collective Hospitality earlier this year. That’s when the wheels came off.

The “new owners” claimed Remote Year was “toxic” and basically said, “Thanks, but no thanks,” refusing to provide funding, payroll, or any real support. Meanwhile, Remote Year’s leadership couldn’t untangle the mess, leaving vendors unpaid and customers furious.

Lesson #1: Choose your buyers like you’d choose a partner—because bad ones can leave you bankrupt, literally and emotionally.

Four Takeaways for Anyone Who Runs a Business

1. Control is King

If you don’t control the decisions, you don’t control your destiny. Remote Year’s founders handed over the keys, and new owners slammed the brakes. Always think twice before trading autonomy for a payout.

2. Growth is Great… Until It’s Not

Venture capital is like caffeine: a quick boost, but too much can leave you shaky. Remote Year scaled fast, but when the pandemic hit and the market shifted, they weren’t nimble enough to adapt.

3. Align or Die

Acquisitions work when both sides want the same thing. When they don’t, chaos ensues. If your goals don’t align with a buyer—or an investor—it’s a recipe for disaster.

4. Always Have a Plan B

Whether you’re a founder, vendor, or employee, don’t rely on anyone else’s survival for your own. When the money dries up, you don’t want to be the one left holding the (empty) bag.

The Bigger Picture

This isn’t just a story about Remote Year; it’s a story about every founder, team member, and investor who ever bet it all on someone else’s promises. Ownership matters. Alignment matters. And most of all, having a backup plan matters—because the best dreams don’t have to end in bankruptcy court.

SUPPORT TODAY’S SPONSOR:

AI could turn $10,000 into $1M in the next few years? – here’s how

Artificial Intelligence is being called the next $100 trillion industry—and early investors could have a rare chance to profit.

Renowned investor, James Altucher, believes AI will be the biggest financial opportunity of the decade. He has a history of making accurate predictions about emerging technologies, and his latest focus is on AI.

Altucher claims that a $10,000 investment in the right AI stocks could turn into $1 million or more in the coming years.

But this opportunity won’t last forever. He predicts that the window to get in on these AI investments will end very soon— and in this video explains how everyday investors can take advantage of this “wealth window” before it’s too late.

Plus, he’s also revealing one of his top AI stock picks for free. Don’t miss this chance to get in early on what could be the biggest tech revolution yet.

Watch the video now and see the full AI investment research plan

THIS WEEK’S BIZ QUIZ:

STRATEGIC THINKING:

Automating Customer Journeys: Blow Their Minds (And Your Bottom Line)

Let’s be honest—most customer experiences are snooze-fests. Boring emails, generic follow-ups, and offers that scream “meh.” But not yours.

Oh no, you’re about to deliver an experience so personalized, so seamless, your customers will think you’ve got a sixth sense. (Spoiler: It’s AI, but they don’t need to know that.)

Here’s the deal: You’re already working hard to attract attention. So why let that hard-earned lead slip through the cracks? Instead, build a journey so good they’ll never want to leave.

5 Strategic Moves to Make Them Say “WOW”

1. Stop Guessing. Start Mapping.

Imagine planning a road trip without a map. Chaos, right? Same with your customer journey. Plot out every touchpoint—where they discover you, how they engage, and when they’re ready to buy. Tools like ZenWareAI (shameless plug for us!) make it ridiculously easy to map this out. (Trust me, you’ll feel like a marketing wizard.)

2. Segment or Suffer.

Sending the same message to everyone? Rookie move. Your audience isn’t a one-size-fits-all crowd, so segment them like a pro—newbies, VIPs, and everyone in between. AI makes this easy, and the payoff? Jaw-dropping engagement.

3. Make It Personal (Without Creeping Them Out).

AI-powered dynamic content is your secret weapon. Whether it’s “Hey, Alex, saw you loved [product]!” or tailored recommendations, make your customers feel like you’re speaking just to them. No copy-paste vibes here.

4. Automate Without Losing the Love.

“Set it and forget it” sounds nice, but your audience deserves better. Sure, automation handles the heavy lifting, but sprinkle in some human magic—like a heartfelt thank-you email or a cheeky nudge to check out your latest offer.

5. Surprise, Delight, and Dominate.

Everyone loves a good plot twist. Throw in unexpected bonuses, exclusive offers, or even just a funny GIF in your follow-ups. These little moments are what turn casual customers into raving fans.

Action Steps to Get You Rolling

1. Map out your customer journey (seriously, grab a coffee/tea and do it now).

2. Set up one automated sequence this week—just one! Keep it simple but impactful.

3. Test and tweak like your business depends on it (because it does).

4. Add a surprise element to your journey—something to make them grin.

So, ready to transform your customer journey from “meh” to “mind-blowing”? This is the perfect week to reflect on how you’ll upgrade your game to outpace your competition!

Want some help with it? Hit reply, and let’s cook up something amazing together. You’re just a few tweaks away from turning leads into loyal superfans.

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Quiz Answer