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Jason “Deep Dive” Lord • • About the Author
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Daydream Deductible – Biking the Chicago Loop, One Business Expense at a Time

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Daydream Deductible – Biking the Chicago Loop, One Business Expense at a Time

Daydream Deductible – Biking the Chicago Loop, One Business Expense at a Time

Posted by Deep Dive AI

The bikes are booked, the train tickets are punched, and our Airbnb awaits in the shadow of Chicago's skyline. But the trip hasn’t happened yet—we’re still riding the excitement of a dream that’s already tax-tagged and story-ready.

🎒 Planning the Write-Off of the Century

Chicago’s Loop is about to get a visit from a couple of determined content creators with a camera, a cat, and a pocket full of 1099 logic. This isn’t just a vacation. This is a mission in monetization. The upcoming trip will be fully documented, fully deliberate, and just maybe... fully deductible.

🎥 Packing the Gear – Sponsored by Strategy

As we prep for departure, our gear list looks more like a production studio manifest. A GoPro HERO12 is packed and ready to mount for helmet footage. The RØDE Wireless ME mic system has been tested in wind tunnels (read: our driveway). Kellie’s bringing the Canon EOS R50 for street-level storytelling. And yes, our Russian Blue cat will be riding in style with aviator goggles.

💼 The Vision: Blending Business and Breeze

We’ve got affiliate tags locked, content themes queued, and storyboards scribbled across sticky notes. The goal? Ride the Chicago Loop on folding bikes, film the journey, explore the unexpected, and document it all through a lens of humor, hustle, and maybe some jazz saxophone solos.

There will be footage. There will be deductions. And there will definitely be pizza.

🧾 A Checklist from the Sky

Already looming in our minds: an angelic IRS auditor with a clipboard and a knowing smirk. We imagine them hovering as we plan:

  • [✓] “Trip planned with content deliverables”
  • [✓] “Affiliate gear selected and prepped”
  • [✓] “Deductible business purpose outlined”

We’re not sure if the IRS believes in influencer write-offs, but we’re bringing our best arguments—and a backup lapel mic.

🛒 Deep Dive AI’s Gear Picks – Adventure Essentials

Your purchases help fund this upcoming ride and keep our content rolling. We appreciate your support!

🚉 One-Way Ticket to Monetized Mischief

We’ll be boarding the Amtrak soon with our folding bikes folded and our hopes high. Our Airbnb hosts probably don’t realize they’re part of a content plan. But they are. Every moment—from the skyline to the sidewalks—is a set piece in a lightly exaggerated but entirely earnest quest to turn exploration into enterprise.

We haven’t pedaled a single Chicago block yet, but we’re already spinning stories. This is just the beginning.

🎧 Stay Tuned: We'll be filming, documenting, tagging, and probably giggling all the way. Subscribe and follow to ride along once the journey begins:

  • 🎥 YouTube: @DeepDiveAI

    • #DaydreamDeductible #BikeVlog #TaxWriteOffTour #ChicagoLoop #DeepDiveAI #AffiliateMarketingOnWheels

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