iiinova — where your digital self keeps evolving

Capt. Jack Sharrow @sharrows.bsky.social · 15/10/2026

Seeing my fellow millennials at the Smashing Pumpkins concert who brought their kids so they can scroll tik tok instead of appreciating these Legends. 🎃

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Capt. Jack Sharrow @sharrows.bsky.social · 14/10/2026

Also, I don’t shop at 5 below but based on this sign they have every price imaginable except under $1?? Top notch marketing.

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Capt. Jack Sharrow @sharrows.bsky.social · 14/10/2026

Hands up for who’s surprised Water Tower is AI hell 🙄🤮

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Capt. Jack Sharrow @sharrows.bsky.social · 14/10/2026

Meet me at the Checks Cashed. Meet me at Devil Dawgs. Meet me at the combination Checks Cashed Devil Dawgs.

Combination check cash spot and devil dawgs

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Capt. Jack Sharrow @sharrows.bsky.social · 18/09/2026

I ordered my impossible burger at Sox park from the Fyre Fest menu. From the urbanism, bike valet, entrance experience, and concessions, the Cubs really are better in every way. Except tix prices. Shoutout to the best part of the Sox: @chicagobikesox.com

The saddest impossible burger, one sad tomato slice, no other toppings

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Capt. Jack Sharrow @sharrows.bsky.social · 12/09/2026

What’s your favorite part of Cubs games? Baseball. Definitely the baseball that’s happening on the field.

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Capt. Jack Sharrow @sharrows.bsky.social · 12/09/2026

Lit Fest blocking the bike lane bc the whole street is pedestrianized??? APPROVED.

Bike lane blocked by beautiful book people

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Capt. Jack Sharrow @sharrows.bsky.social · 11/09/2026

Birthday dinner means I called the most expensive chauffeur I could think of 💃🕺🏽 🚍

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Capt. Jack Sharrow @sharrows.bsky.social · 10/09/2026

When I’m elected mayor, all buses will be treated as emergency vehicles where cars will be forced by law to heed the right of way. Buses will also be equipped with snow plow scoops to assist with car removal.

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Capt. Jack Sharrow @sharrows.bsky.social · 06/09/2026

Not me trying desperately to create core memories by handing stickers to kids on the back of cargo bikes at BTD. Several successful distributions.

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Capt. Jack Sharrow @sharrows.bsky.social · 01/09/2026

Every. Day. Whether it’s a lost taxi, drunk driver, or yes, even a driver with a permit from the Parks, our “car free” lakefront trail is anything but. But go off about fast e-bikes and scooters while these 2 tons living rooms roam our trails unimpeded.

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Capt. Jack Sharrow @sharrows.bsky.social · 28/08/2026

Believe me when I tell you, if the people in power gave a shit about our safety, we’d be talking about the cars I see on the lakefront trail every day and every night. Follow the money.

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Capt. Jack Sharrow @sharrows.bsky.social · 26/08/2026

While I wait for my local bike shop to work on my bike, I’m eating this, drinking a horchata while Chicago house music plays. I’m never leaving this city.

Enchiladas with sweet plantains smothered with sour cream and mole, side of rice and beans

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Capt. Jack Sharrow @sharrows.bsky.social · 23/08/2026

When the in-laws needed seating and refreshments to watch their son in the tri and all roads are closed - #BikeIsBest

Cargo bike being the chairs and blanket with cooler, watching cyclists in the Chicago chi, city in the background

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Capt. Jack Sharrow @sharrows.bsky.social · 22/08/2026

Omg first Sky game and it was top 5 Chicago sporting events. Game winning 3 with .6 seconds left holy cow. My fav part had to be the Metra race! 2nd fav part was the 3 block walk to the arena.

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Capt. Jack Sharrow @sharrows.bsky.social · 13/08/2026

Was it my most difficult haul? Not even close. Was it my heaviest? By far. 1 case of water, 2 cases of soda, 1 case of energy drinks plus more. The lower center of gravity and geometry of the bike made riding a breeze. 🦾 #OneLessCar #BikeIsBest

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Capt. Jack Sharrow @sharrows.bsky.social · 12/08/2026

We tried to hang out in the grassy area of the Obama Center and this nice cop said this is private property and we had to leave. At least they didn’t drone strike us??? 🫠

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Capt. Jack Sharrow @sharrows.bsky.social · 12/08/2026

If you asked me to design what I think the prison from The Platform would look like from the outside, this is what I would show you.

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Capt. Jack Sharrow @sharrows.bsky.social · 09/08/2026

Fly the Co-Op, I missed it last year so I was determined.

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Capt. Jack Sharrow @sharrows.bsky.social · 09/08/2026

Saw 2 bike friends on the LFT today!! Surprised I’m still alive after yesterday’s ride! 💀

Screenshot of a long ass bike ride around Chicago

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Capt. Jack Sharrow @sharrows.bsky.social · 08/08/2026

Rich bc I live where ppl vacation. 😎 Play bikes today 🤙🏽

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Capt. Jack Sharrow @sharrows.bsky.social · 08/08/2026

From the rapper that brought you Fyre Fest 🙄

Ja rule cancelling his performance at Sox park

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Capt. Jack Sharrow @sharrows.bsky.social · 02/08/2026

The JCPenney cuck chair is out of order.

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Capt. Jack Sharrow @sharrows.bsky.social · 01/08/2026

Summer train beer on the way to the airport hits hardddd 🔥🔥🔥

Kalamazoo’s finest Oberon against the Southside backdrop out the train window

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Capt. Jack Sharrow @sharrows.bsky.social · 31/07/2026

We need stronger words than AI slop

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Capt. Jack Sharrow @sharrows.bsky.social · 30/07/2026

I’m eating pizza you’ve never heard of with toppings you can’t comprehend.

Cockpit view of TNMT from the bucket of my cargo bike

Rafael sitting in the bucket of a cargo bike

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Capt. Jack Sharrow @sharrows.bsky.social · 29/07/2026

Tonight is the TMNT x bike riding crossover I didn’t know I needed in my life. 🐢 🚲 #BikeChi

Flyer for bike ride to watch ninja turtles

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Capt. Jack Sharrow @sharrows.bsky.social · 22/07/2026

Transit to both airports. Transit to both ballparks. Best city in the world. 💯

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Capt. Jack Sharrow @sharrows.bsky.social · 21/07/2026

Drivers having a normal one in Pilsen today 🙄 #bancars

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Capt. Jack Sharrow @sharrows.bsky.social · 21/07/2026

Ward 3 has entered the chat!! I’m gonna teach him how to take bike pictures without cars in them but as long as he doesn’t rip out bike lanes, we got hope!

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Capt. Jack Sharrow @sharrows.bsky.social · 21/07/2026

#BikeChi join us for a glorious bonfire to celebrate 5yrs of Riding Bikes and Spreading Joy!! cxs-anniversary.eventbrite.com

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Capt. Jack Sharrow @sharrows.bsky.social · 12/07/2026

What’s the feeling that’s the complete opposite of someone stealing stuff off your bike bc that’s how it felt coming back to my bike and finding the best stickers in the land on my bike 🥰🥰🥰 @chicagobikesox.com

Chicago bike Sox stickers strapped to my speaker on my bike

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Capt. Jack Sharrow @sharrows.bsky.social · 11/07/2026

Haircut at my cousins new spot, Broadway closed to cars means extra VIP parking, shoot all of this straight into my veins. 🤤🥰😻

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Capt. Jack Sharrow @sharrows.bsky.social · 11/07/2026

Full suspension is like riding on the clouds on a bed of pillows

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Capt. Jack Sharrow @sharrows.bsky.social · 09/07/2026

And military on every corner because freedom! 🇺🇸

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Capt. Jack Sharrow @sharrows.bsky.social · 09/07/2026

And they have patios just like Paris 🇫🇷

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Capt. Jack Sharrow @sharrows.bsky.social · 09/07/2026

Great news, DC has bike lanes just like Chicago! 🖕🏽

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Capt. Jack Sharrow @sharrows.bsky.social · 07/07/2026

Hired a private chauffeur to see me to my train to the airport. Anyone have recommendations for sightseeing in DC??? 🤡

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Capt. Jack Sharrow @sharrows.bsky.social · 03/07/2026

Imagine if any part of lakeshore drive looked like this how fast the city would fix it for drivers 🙄

Flooded tunnel from the lakeshore trail under lakeshore drive

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Capt. Jack Sharrow @sharrows.bsky.social · 28/06/2026

Illinois has the gayest transit 🏳️‍🌈

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Capt. Jack Sharrow @sharrows.bsky.social · 28/06/2026

Current vibes on Broadway 🏳️‍🌈

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Capt. Jack Sharrow @sharrows.bsky.social · 28/06/2026

Fresh off our 2nd Street Vendor Bike Tour Ride, our sticker spotted in the wild. It warms my cold dead heart that the #BikeChi community has embraced this bike meets mutual aid force for good. We are all we got. We are all we need. ✊🏽

Bikes locked to bike rack, CxS sticker on fork

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Capt. Jack Sharrow @sharrows.bsky.social · 26/06/2026

Gotham vibes from the VIP section at Northerly Island for Martin Garrix 😎

Chicago skyline looking north west, tops of skyscrapers

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