Recent Posts
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Why Flight Prices Fluctuate (and How to Outsmart the Madness)
If you’ve ever opened ten browser tabs just to watch the same flight bounce around like a ping pong ball, you’re not alone. One minute it’s $243, the next it’s $387, then $293. It feels random. Maybe even a little personal. But here’s the thing: flight pricing isn’t magic. It’s math. Data. Algorithms.…
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Plan Together, Not in Circles: Why Retreats Fail Without Early Team Input
I once spent three weeks planning a team retreat that never happened. Not because we didn’t try, not because the team didn’t care. But because we planned it wrong, we planned it alone. It started with the best of intentions. I had taken the lead on organizing our next offsite, something meant to…
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The Future of Business Travel Isn’t Solo- It’s Social
Aha Moment A few years ago, I found myself sitting in a hotel lobby in Austin, staring at a spreadsheet, a Slack thread, and a Google Form, trying to coordinate flights for a 8-person leadership team across three time zones. We were planning our first in-person retreat since going fully remote, and what…
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Why Remote Teams Still Need In-Person Time: The Science Behind Human Connection
Introduction: In the wake of the pandemic, remote and hybrid work have become the norm for many organizations. As a former HR professional and now the CEO of a travel tech company, I’ve witnessed both the benefits of remote work and its hidden costs. Productivity may remain high in a distributed team, and…
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What Top Startups Get Right About Offsites (That Everyone Else Misses)
In the realm of remote work, many startups recognize that while digital tools facilitate communication, they can’t fully replace the depth of connection forged through in-person interactions. Leading companies like GitLab, Zapier, and Notion have embraced this understanding, leveraging offsites not just as retreats but as strategic investments in their teams’ cohesion and…
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The Hidden ROI of Team Offsites: What Most Leaders Miss
Most leaders know intuitively that team offsites are fun. But fewer recognize how these gatherings drive serious business results. One tech founder learned this firsthand: he spent $20,000 to take his 14-person startup on an offsite and was told it was frivolous – yet he called it “the best investment I could have…
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Offsite Horror Stories (and How to Avoid Them)
Everyone loves a team retreat. But let’s be honest, when things go wrong on a company trip, they go really wrong. The group dinner that turns into a stomach bug epidemic, the “easy hike” that somehow becomes a six-hour survival test, or the Wi-Fi that “totally works” (spoiler: it doesn’t). Every team has…
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Why Great Team Offsites Start Before You Even Land
Company offsites get hyped as the fix for everything. Culture booster? Of course. Strategy breakthrough? You bet. Burnout cure? Where do I sign? And hey, sometimes they are. But here’s the truth: a truly game changing offsite doesn’t start when you roll into your Airbnb or crack open that first Pellegrino in the…
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✈️ “Seriously, Where Should I Take My Team?”
My Top 5 Unique Cities for a Company Retreat That Everyone Will Actually Enjoy You’re not looking for another list of “Top 10 Conference Cities.” You want something fun, accessible, and actually worth flying the team in for. Somewhere that feels like a break from the usual—and still makes space for real connection.…
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The Most Overlooked Costs When Planning a Company Trip
Spoiler: It’s never just flights and hotels. Planning a team offsite? Company retreat? Founder getaway with a few Airbnb and Hotel spreadsheets already open? Great! But before you hit “book,” let’s talk about the sneaky, under the radar costs that tend to surprise even the most seasoned trip planners. Because the truth is:…