iiinova — where your digital self keeps evolving

Capt. Jack Sharrow @sharrows.bsky.social · 19/09/2026

Deeeeetroit style dish deep on bikes is a match made on 8 mile, really doe 💯

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

2201

Capt. Jack Sharrow @sharrows.bsky.social · 16/09/2026

Breaking generational curses but it’s just me not leaving events early to beat traffic to drive back to the suburbs bc we park our bike out front and ride home peacefully.

1424

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.

2514

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

2260

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

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

1180

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

Seeing my bike shop owner in the wild is like running into your drug dealer like oh I’ve given you thousands of dollars for my vice 😈

1151

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.

4392

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.

2300

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.

511313

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.

0403

Capt. Jack Sharrow @sharrows.bsky.social · 27/08/2026

Are cars allowed on trails and bike paths? Exactly. 🙄

0121

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

5340

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

1111

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.

1171

Capt. Jack Sharrow @sharrows.bsky.social · 20/08/2026

Parks can’t keep cars off the lakefront trail but they have surveillance money for people who need housing. Cool cool cool

14114

Capt. Jack Sharrow @sharrows.bsky.social · 15/08/2026

Doing a rain dance to wash out the air and water show but not our party 💃🌧️ who am I kidding, we ride in any weather

0143

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

2301

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??? 🫠

44511

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.

060

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

1230

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

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

1354

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

2120

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

It feels wrong being here without the homies @chicagobikesox.com like being in a store without the staff, we took the Bike Sox route in solidarity ✊🏽🚲⚾️

1140

Capt. Jack Sharrow @sharrows.bsky.social · 07/08/2026

Imagine with me for a moment. Sox + Ja Rule.

050

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

The JCPenney cuck chair is out of order.

1111

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

2140

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

We need stronger words than AI slop

7200

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

1150

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

0100

Capt. Jack Sharrow @sharrows.bsky.social · 25/07/2026

& Juliet is a masterpiece and my Chicago peeps need to run, not walk to catch it while it’s in town. Spoiler alert: multiple bikes featured!! 😍🥰

030

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

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

3554

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

Drivers having a normal one in Pilsen today 🙄 #bancars

4200

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

0248

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

Is 2 home runs and 4 runs in the first inning bad? I don’t watch ball match a lot. For context, I’m wearing my Tigers gear. Wife is in Cubs gear.

160

Capt. Jack Sharrow @sharrows.bsky.social · 20/07/2026

Whenever I find myself waiting for someone outside, I try to find a bike rack bc if I’m chilling anyways, lemme put some eyes on bikes for my homies. That’s solidarity. ✊🏽🫶🏽

1111

Capt. Jack Sharrow @sharrows.bsky.social · 19/07/2026

The amount of guys at the grocery store watching the soccer game on their phone at full volume was criminal. I hope they wrecked their cybertruck on the way home. @shredded-teat.bsky.social you won’t be surprised it was the Roosevelt jewel

1130

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

1282

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. 🤤🥰😻

28010

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

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

4281

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??? 🤡

1130

Capt. Jack Sharrow @sharrows.bsky.social · 05/07/2026

The amount of ppl I’ve seen with umbrellas getting absolutely demolished these past two days. Like bruh.

170

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

0316

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

Happy Traffic Calming Fire Hydrant season to all who celebrate!!! I passed one in Pilsen yesterday and it looked like a block party with tons of kids playing in the street. Love to see them.

0101

Capt. Jack Sharrow @sharrows.bsky.social · 02/07/2026

Thinking maybe me and the Mrs should renew our vows this year for our 10 year anniversary. I won’t tell yall the date, just keep an eye on the Sears tower.

090

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

@chicagocta.bsky.social Protected bus lanes for these on every major street you cowards

0120

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

Illinois has the gayest transit 🏳️‍🌈

39110