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Bill Winterberg

@billwinterberg.bsky.social
1K followers 791 following 3.9K posts

Make financial planning more accessible with fintech. 🎥 Content producer 🏆 Award-winning pinball player 📍Boston.

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Bill Winterberg @billwinterberg.bsky.social · 03/10/2026
Nice night for some high school football
A nighttime scene of high school football on a football field with lights
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Reposted by Bill Winterberg
taxgirl @taxgirl.bsky.social · 02/10/2026
The IRS is looking for VITA/TCE volunteers for filing season. Last year, I said yes—and ended up preparing tax returns in rural Alaska, traveling by single-engine plane and snowmobile. ❄️ You don’t need tax experience to volunteer. Here’s more: www.taxgirl.com/2026/10/01/i...
taxgirl.com
IRS Is Looking For Tax Volunteers. Here’s Why I Flew 4,300 Miles To Be One. | Taxgirl
The IRS is seeking VITA volunteers for the upcoming filing season. Here’s what I learned preparing tax returns for free in rural Alaska.
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Bill Winterberg @billwinterberg.bsky.social · 01/10/2026
I found some pinball!!
Bill taking a selfie in front of pinball machines at Aero Club Bar in San Diego, California
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Bill Winterberg @billwinterberg.bsky.social · 30/09/2026
24 hours in San Diego. First time I’ve seen sunshine since last Thursday (because Nor’easter) ☀️
The San Diego downtown skyline in the background with Harbour Island and boat slips in the foreground 
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Bill Winterberg @billwinterberg.bsky.social · 30/09/2026
IMO we should probably call AI agents AI minions, because the agents evidently do activities on par with the level of Minions
static.klipy.com
M
ALT: M
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Bill Winterberg @billwinterberg.bsky.social · 28/09/2026
Reached Escape Nublar on Jurassic Park pinball again, but yet again was a few shots short of completing the final mode. You have to make ALL the Rescue targets. 😅 409M Visitor Center champ, 8 DNA combos, 8 fossils found.
Bill taking a selfie in front of a Jurassic Park pinball machine with a high score #1 of 4,474,456,170 and the name BILLW
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Bill Winterberg @billwinterberg.bsky.social · 27/09/2026
Yard is saturated and the retention pond is overflowing. But my basement sump wells are still bone dry. I wonder how long that will last before the water table rises 🫣
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Bill Winterberg @billwinterberg.bsky.social · 25/09/2026
Goodbye Subaru, you were a fun car to own. 🥲
A 2004 Subaru Impreza WRX wagon in Platinum Silver Metallic loaded on a vehicle transport ready for shipping. A VW is also parked on the transport trailer, towed by a red diesel truck. Trees are visible behind the trailer and a two lane road is in the foreground
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Bill Winterberg @billwinterberg.bsky.social · 25/09/2026
Now I am not a conspiracist, buuuuutttt if AI were to go rogue and try to go after humans, disabling their food storage seems like a pretty clever way to starve them… 🙃
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Bill Winterberg @billwinterberg.bsky.social · 25/09/2026
Seems bad to go outside this weekend 🌧️
A weather forecast for Friday 9/25 through Tuesday 9/29 that shows significant rain and high sustained winds for the Boston metro region
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Bill Winterberg @billwinterberg.bsky.social · 24/09/2026
I didn’t forget to do the dishes last night, it’s just that I went rogue and hacked in* to my pinball machine in the basement *turned on the power button and pressed Start
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Bill Winterberg @billwinterberg.bsky.social · 24/09/2026
Belief in AI extinction is pretty much adapting Pascal’s Wager to the 21st century 🤷‍♂️
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Bill Winterberg @billwinterberg.bsky.social · 22/09/2026
It’s pinball night in New England! I forgot to post from the first week of league play last week, but here’s a photo from week two. 
Bill taking a selfie standing in front of a row of pinball machines at Hometown Arcade in Norwood, Massachusetts 
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Bill Winterberg @billwinterberg.bsky.social · 22/09/2026
Tokenmaxxing: When you get three pinball games for eight tokens instead of just one game for four tokens. 🧠
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Bill Winterberg @billwinterberg.bsky.social · 21/09/2026
Love to see speed enforcement 🚔
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Bill Winterberg @billwinterberg.bsky.social · 19/09/2026
New GC on Jurassic Park. Failed stage 4 of Escape Nublar 😫 581M visitor center bonus, 321M visitor center victory, 318M secure control room victory, 48 rescues, 4 trifectas achieved. Big game!! 😮‍💨
Bill taking a selfie in front of a Jurassic Park Pro pinball machine with a Grand Champion score of 4,698,754,650 and the initials BILLW
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Bill Winterberg @billwinterberg.bsky.social · 18/09/2026
Teaching my son to drive, and I routinely comment how to keep to the right on two-lane roads, as some oncoming cars can drift over the center yellow line. This morning: frontal offset collision on the two-lane road by our house. One car drifted over the painted center line & collided with the other
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Bill Winterberg @billwinterberg.bsky.social · 14/09/2026
Nest thermostats are still dumb, because they never tell me when it’s nice enough outside to open the windows and turn off the A/C. Instead it just mindlessly follows its daily programming 🤷‍♂️
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Bill Winterberg @billwinterberg.bsky.social · 13/09/2026
Finally reached Escape Nublar for the first time, one shot away from completing 😫. 841M Escape Nublar. Maybe 250M Museum Mayhem completed. No King of the Island or Invalid? in this game. 480M Visitor Center bonus. 2 EBs. Home game
A Jurassic Park pro pinball machine backglass with a score display that says GRAND CHAMPION
BILLW
3,477,154,280
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Bill Winterberg @billwinterberg.bsky.social · 12/09/2026
NGL, I kindof respect the graphic 💵🧐
static.klipy.com
Sorry
ALT: Sorry
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Bill Winterberg @billwinterberg.bsky.social · 11/09/2026
High school football is back! 🏈
Two football teams on Brooks Field in Milton, MA with a sunset in the background
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Bill Winterberg @billwinterberg.bsky.social · 10/09/2026
Bud Fox: Hey chat, where is Sir Lawrence Wildman going? Chat: Sure Bud! He’s headed to Erie, PA, the headquarters of Anacott Steel. I looked into Wildman’s phone location pings that shows he’s at a private airport. I crossed referenced real-time FAA flight plans, revealing the obvious destination!
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Bill Winterberg @billwinterberg.bsky.social · 09/09/2026
2010: What new cool, useful app did you download to your phone today? 2026: What soul sucking, attention hijacking app did you delete from your phone today?
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Bill Winterberg @billwinterberg.bsky.social · 09/09/2026
I’m starting to get concerned at the number of times my web browser accuses me of not being a human. 😬
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Bill Winterberg @billwinterberg.bsky.social · 08/09/2026
Heyyyyyyyyyy 👋
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Bill Winterberg @billwinterberg.bsky.social · 07/09/2026
I’m selling my original-owner 2004 Subaru Impreza WRX sport wagon on @bringatrailer.bsky.social. Here’s a blobeye wagon in really good shape that I’ve carefully maintained for 22 years that’s ready for another owner. bringatrailer.com/listing/2004...
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Bill Winterberg @billwinterberg.bsky.social · 04/09/2026
Finally got to the Visitor Center mode in Jurassic Park pinball and successfully completed it, and then stacked on some additional victory points with several targets hit. JP is just a complete game: code, shots, risk/reward. 👌
A Jurassic Park pinball machine display with a score of 2,104,609,180 and the name BILLWA Jurassic park pinball machine display with Visitor Center Champion of BILLW with a score of 289,668,100
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Bill Winterberg @billwinterberg.bsky.social · 02/09/2026
I’ve gotten so accustomed to tap-to-pay now, that two trips in a row to the pet store, where I have a gift card in my wallet with funds to pay, I used my phone to pay and totally forgot to spend down my gift card! 🤦‍♂️
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Bill Winterberg @billwinterberg.bsky.social · 30/08/2026
“Satisfaction is churn. Misery is recurring revenue.” Fairly gut-check type of read. I do loathe today’s “internet” more than I love it.
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Bill Winterberg @billwinterberg.bsky.social · 29/08/2026
@joe.radjunk.com yoooo I recognize those photos!
Jersey Jack Pinball's Post on Facebook
Jersey Jack Pinball
• • •
Where are you playing this #SonicSummer?
Every visit to your favorite local arcade is another chance to put your initials on the screen. Show us where Sonic the Hedgehog Pinball is taking you this summer!
Tag Jersey Jack Pinball and use #SonicSummer for a chance to be featured.
Visit our pinball map via the link in bio to find a machine near you!
Several photos are included that are most definitely from RadJunk video game store in Fort Walton Beach, Florida but for some reason are not tagged or attributed to RadJunk 🤷‍♂️
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Bill Winterberg @billwinterberg.bsky.social · 29/08/2026
That sunrise keeps getting later and later. Let’s go ride bikes with friends! 🚲 
A sunrise with mostly clear skies over the gazebo at Milton Townhall in Milton, Massachusetts 
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Bill Winterberg @billwinterberg.bsky.social · 29/08/2026
I love this. And I also hate this. @gravelinfluencer.bsky.social youtu.be/dWHCef7F8gY?...
youtu.be
America Hates Bikes
YouTube video by Climate Town
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Bill Winterberg @billwinterberg.bsky.social · 26/08/2026
I’m selling my Deadpool Pro pinball machine (yes, the one I scored 29 billion points on!). Located near Boston, easy loading with help available 💪 pinside.com/pinball/mark...
pinside.com
For sale: Deadpool (Pro)
Used but in like-new condition Deadpool Pro with only 254 plays. Watch my gameplay video demonstrating all the shots: https://youtu.be/KoP8t2pAwsQ I’m the second owner of this machine, I bought it wi...
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Bill Winterberg @billwinterberg.bsky.social · 26/08/2026
Vanguard to Acquire Altruist, Expanding the Reach and Impact of Financial Advice altruist.com/news/vanguar...
altruist.com
Vanguard to Acquire Altruist, Expanding the Reach and Impact of Financial Advice - Altruist
Altruist to operate as a standalone business, extending the “Vanguard effect” to more advisors and theirclients through AI-forward wealth technology and custody platform VALLEY FORGE, PA (August 26, 2...
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Bill Winterberg @billwinterberg.bsky.social · 22/08/2026
Pretty, pretty good 👌
A dinner table setting with a platter of lemon butter garlic chicken with lemon slices on top, roasted rosemary potatoes, steamed broccoli, and strawberries and blueberries. 
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Bill Winterberg @billwinterberg.bsky.social · 22/08/2026
1.3 billion is pretty good, except I completely bricked in the Visitor’s Center mode 🤦‍♂️
A Jurassic Park Pro pinball machine Gamr Over screen with a score of 1,378,471,300 by player BILLW
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Bill Winterberg @billwinterberg.bsky.social · 22/08/2026
Thanks to the Boston helicopter alarm clock, I am up early and ready to go ride bikes with friends! 
An overcast sky behind the gazebo at Milton town hall in Massachusetts 
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Bill Winterberg @billwinterberg.bsky.social · 22/08/2026
Ok Boston what’s with the low-flying helicopters at 5:30 and 5:45 am?? 😫
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Bill Winterberg @billwinterberg.bsky.social · 22/08/2026
“Dead pool” was trending this week 😈
A Deadpool Pro pinball machine with a score of 14,508,767,440 and the name BILLW
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Bill Winterberg @billwinterberg.bsky.social · 20/08/2026
On today’s (backup) bike ride, my bottom bracket started to make some pretty loud clicking noises. Not my backup bike, too! 😫 Turns out it was dirt and grime accumulated between the left crank arm and outer bracket face. Cleaned that all up and now the drivetrain is smooth and quiet again. Whew! 😅
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Bill Winterberg @billwinterberg.bsky.social · 15/08/2026
Wake up early and go ride bikes!!
A sunrise at the gazebo across the street from Milton Town hall in Milton, Massachusetts 
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Bill Winterberg @billwinterberg.bsky.social · 10/08/2026
It’s absolutely pouring down rain south of Cleveland, so we won’t be headed to New York all that early today. Looks like it’ll be a late night check in outside Syracuse.
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Bill Winterberg @billwinterberg.bsky.social · 09/08/2026
Just passing through…
A stone floor map of Indiana with interstate highways illustrated along with the locations of the following cities:

GARY
SOUTHBEND 
ELKHART
AUBURN
FORT WAYNE
MARION
LAFAYETTE
MUNGE
ANDERSON
CRAWFORDSVILLE
TERRE HAUTE
INDIANAPOLIS
RICHMOND
BLOOMINGTON
COLUMBUS
BATESVILLE
SCOTTSBURG
NEW ALBANY
ANSVILLE
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Bill Winterberg @billwinterberg.bsky.social · 09/08/2026
Camping outside Indianapolis is better with a barbecue grill 😋
A MAGMA barbecue grill with seasoned chicken thighs and sliced zucchini cooking on the grates.
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Reposted by Bill Winterberg
StreetsblogMASS @mass.streetsblog.org · 07/08/2026
Beginning today, @massdcr.bsky.social will test weekend restrictions on motor vehicle traffic on parts of Chickatawbut Road and Wampatuck Road in the heart of the Blue Hills Reservation. mass.streetsblog.org/2026/08/07/d...
mass.streetsblog.org
DCR Pilots Car-Free Roads In Blue Hills Reservation This Weekend - Streetsblog Massachusetts
Beginning today, the Massachusetts Department of Conservation and Recreation (DCR) will test weekend restrictions on motor vehicle traffic on parts of Chickatawbut Road and Wampatuck Road in the heart...
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Bill Winterberg @billwinterberg.bsky.social · 06/08/2026
Hey @medi-nerd.com, I made it to Indianapolis for the DCI prelims today and here to see my son perform In Gold. 😁
Bill taking a selfie in a park in front of the Gold drum corps brass warmup semicircle in Indianapolis, Indiana
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Bill Winterberg @billwinterberg.bsky.social · 06/08/2026
Old railroad tracks converted to walking and cycling paths rule! 🚲 strava.app.link/PmvY4HF4n5b
A Strava cycling activity map titled the Pennsy Rail Trail, Indianapolis
Distance, 21.03 mi
Elev Gain, 404 ft
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Bill Winterberg @billwinterberg.bsky.social · 03/08/2026
Yes, there are three pinball machines in the Rock ‘n Roll Hall of Fame, but they’re all turned off today since there’s live music next door
Build taking a selfie in front of a Foo Fighters pinball machine at the rock ‘n’ roll Hall of Fame in Cleveland, Ohio 
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Bill Winterberg @billwinterberg.bsky.social · 03/08/2026
For those about to rock, we salute you! 🤘
Bill taking a selfie in front of the rock ‘n’ roll Hall of Fame in Cleveland, Ohio 
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Bill Winterberg @billwinterberg.bsky.social · 01/08/2026
Happy (still unofficial) #NationalPinballDay to all who celebrate! 🎉 youtu.be/ankIBUvfkS0?...
youtu.be
Tour Chattanooga's Classic Arcade Pinball Museum for #NationalPinballDay
YouTube video by Bill Winterberg
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