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

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....