Bill Winterberg

@billwinterberg.bsky.social

971 Followers 773 Following

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

A screenshot of The Scoop program on NBC’s National broadcast (that happened to be on the TV in the room where I am, I don’t watch this program and I quickly am learning why it’s probably best that I not watch it ever again)
A 5.25 inch floppy disk with MS-DOS version 2.01 BIN RX50 (c) 1981, 1982 Microsoft Corp Digital Service Approved Lic to Digital Equip Corp in front of a Digital Equipment monitor displaying the Rainbow 100 boot screen.
The Atlanta downtown skyline with partly cloudy skies viewed from the east with several terra cotta roofed buildings of the Emory University campus in the foreground
A 2004 Subaru WRX wagon parked in a snow-covered parking lot with snow-covered trees and a building visible in the background. Definitely built before spyware computers were installed in cars.
Sunrise over the gazebo at Milton town center with a flag pole, with the flag draped at a standstill, indicating no wind
Actor Sean Bean as Boromir from The Lord of the Rings in the “One does not simply walk into Mordor” meme
A Jurassic Park pinball score display showing the Secure Control Room Champion score of 225,060,340 and the name BILLW
Sunrise over the town gazebo at Milton town hall with a flag on a pole showing no breeze
The end of ball bonus screen on Deadpool pinball that shows a total bonus of 3.37 billion points after a bonus multiplier of 25
A Strava activity map for a bike ride labeled BHCC Sherborne with 54.75 miles, two hours and 59 minutes of time and 2986 feet of elevation gain
A sunrise with partly cloudy skies over the gazebo at Milton town center
Bill taking a selfie in front of a row of pinball machines at Hometown Arcade in Norwood, Massachusetts
A fortune cookie reading that says “YOUR TALENTS WILL BE RECOGNIZED AND SUITABLY REWARDED.” By PANDA EXPRESS
A Stern Metallica pinball machine loaded in the back of a red Hyundai Santa Fe SUV with the rear liftgate open.
An iPhone lock screen with the current date of Friday June 19 at 11:49am, then with a notification that reads: BON VOY Worcester is Waiting! Still interested in booking a room at Fairfield by Marriott Inn & Suites Worcester Auburn starting on 5/1/2026? Complete your booking to Worcester to...
A rainbow visible in the sky over a tree line.
Bill taking a selfie in front of a row of pinball machines at Hometown Arcade in Norwood, Massachusetts
A bottle of OBAN SINGLE MALT SCOTCH WHISKY THE MACLEANS A LIMITED EDITION TO CELEBRATE THE EXPERTISE & DEDICATION OF 3 GENERATIONS LIMITED EDITION This West Highland Single Malt Scotch Whisky Finished in 2nd fill ex-Pinot Noir and ex-Sangiovese wine casks, shares notes of sweet vanilla, fresh apple and cake spice. Personally selected by Derek MacLean One of only 4,662 bottles OBAN DISTILLERY OBAN ARGYLL SCOTLAND
A view of the Old Man of Storr rock formations from the Isle of Skye in Scotland with a partly cloudy blue sky in the background and rich green grass hills in the foreground
Sgùrr nan Gillean and Bruach na Frìthe summits in the distance with the Sligachan Waterfalls in the foreground on the Isle of Skye in Scotland.
Bill taking a selfie in front of the Oban Distillery in Oban, Scotland
Bill taking a selfie in front of a row of four pinball machines at lane seven entertainment in Edinburgh, Scotland. From left to right the games are Deadpool, Shrek, Mandalorian, and Stranger Things.
A museum exhibit of historic bicycles hanging on a wall at the National Museum of Scotland
Bill taking a selfie in front of Edinburgh Castle with blue sky in the background.
The Simpsons “worst day of your life, so far” meme where Homer Simpson leans over and points to Bart Simpson.
A Pokémon premium pinball machine with a grand champion score of 333,983,450 with the initials BIL
Bill, taking a selfie in front of the stop button bar and arcade in Fayetteville, North Carolina
A Google Maps street view of Canton Ave in Milton, MA, a two-lane road with a double yellow center line, looking northbound, with cars visible in the northbound lane. A “sharrow” bicycle graphic is painted on the road surface. Sidewalks are visible on both sides of the road. A white fog stripe is painted on the road’s shoulder with approximately 8-10 inches of pavement to the curb, an insufficient distance for a bicycle’s handlebars to safely pass by the side of a stopped vehicle in the road.
Several dozen people lying on inflatable mattresses, covered in blankets and some wearing eye masks, floating on the surface of an indoor swimming pool. The absence of large personal pizzas on their chests is disappointing 🍕
A 2014 Hyundai Sante Fe Limited SUV with the rear hatch open and the rear seats down so a pinball machine can fit in the back.
The northern extension of the Neponset River Trail in Dorchester. The trail is closed by a wire fence and large wooden boards cover the trail surface. A bright orange sign on the right says END DETOUR
Ed’s Take from the same newsletter: Brian Armstrong articulated his vision pretty clearly in his email to employees. The goal isn’t just cutting head count, it’s rebuilding the entire company around AI with humans managing agents rather than managing each other. Sam Altman, Dario Amodei, and others have been pushing the same idea: the one-person billion-dollar company, where a single person manages fleets of AI agents that do everything for them. They’re just glorifying how much value and power you can put into one person’s hands. I don’t think it’s going to work, and not because it can’t technically, but because people don’t actually want it. You don’t spend years building something meaningful and then celebrate alone with your AI agents. Sam Altman said AI consumes less energy than human beings and children. That framing tells you everything about where this thinking has gone wrong.
From the Scott Galloway newsletter: institutional memory was not inefficiency, it was the f*cking company. This was the subject of my No Mercy / No Malice post last week. We work to create economic prosperity and shareholder value, sure. But the whole shooting match of work is you have the opportunity to build something with someone else. The most rewarding thing in life is relationships, and the things that fuse relationships are building things together. If you take away coworkers, it’s like you’ve literally sucked the soul and humanity around what it means to work. Does that mean there aren’t cases where management layers become fat and add negative value? No. But I actually think this is one place where AI is absolutely not going to live up to the hype. AI is not going to replace management and mentoring. What’s really happening here is that a group of CEOs who overhired want to juice their valuations.
A SNAP ACTION SPDT 5A 125V switch connected to a white and green wire with a diode soldered between two switch terminals
A Strava cycling activity map titled Dedham Dinosaur, distance of 26.36 miles in 1 hour 26 minutes with an elevation gain of 1,358 feet
An Apple weather screenshot for My Location in MILTON, MA 49° Drizzle H:61° L:40°. Rain Forecasted Rain for the next hour. Stay Informed Get notifications for severe weather, rain, and snow near you. Enable Notifications • HOURLY FORECAST
A lineup of seven pinball machines at My Parents’ Basement in Avondale Estates, Georgia
A copper Harmon mute for trumpet signed by Wayne Bergeron in black ink. “Look alikes don’t sound alike”
The Rhode Island College performance auditorium with a jazz band setup on the stage on the background, and a program in the foreground with a photo of trumpet player Wayne Bergeron. The program says: RHODE ISLAND COLLEGE DEPARTMENT OF MUSIC presents RHODE ISLAND COLLEGE CONCERT JAZZ BAND Joseph Foley, Music Director featuring Wayne Bergeron, trumpet Guest Artist
Google street view of MA Route 138 in Milton, MA facing southbound. It’s a two lane road with a bike lane on either side surrounded by residences and driveways with neighborhood intersections.
Bill humble bragging about Star Wars: Fall of the Empire pinball scores where the top scores are at least 3.9 billion points
Bill taking a selfie in front of a Pinball Circus replica machine at the Electromagnetic Pinball Museum in Pawtucket, RI
Bill taking a selfie in front of a row of electro mechanical pinball machines at the Electromagnetic Pinball Museum in Pawtucket, Rhode Island
The Tina, Timothee, Kylie watching a basketball game meme
The glowing circular red light of the fictional HAL 9000 computer from the science fiction film 2001: A Space Odyssey
The Simpsons “worst day of your life so far” meme
A rack of baby back ribs on the grill of a pellet smoker
Bill taking a selfie in front of a Star Wars: Fall of the Empire pinball machine with a high score #1 of 5,937,807,950 and the initials BIL
Bill taking a selfie in front of two rows of pinball machines at Tilted 10 in Rockford, IL. His son is photo bombing in the background
The IBM Quantum System One computer sitting in the transept of the Voorhees Computing Center (VCC), a former cathedral. The computer is protected by large glass walls approximately 15 feet high.
A portion of the Scott Galloway newsletter that reads: ED’S TAKE This isn’t really about AI — it’s about inequality, and AI has become the most visible symbol of it.
Deadpool pinball score of 15,067,175,720 with the name BILLW
A white Volvo XC60 on jackstands with both the passenger side wheels removed from the car, with one wheel resting on the floor next to the front wheel well.
The left hand out lane of a Deadpool pinball machine, showing the outline post in the top most hole
Bill taking a selfie in front of Deadpool pinball machine with a high score #2 of 21,916,110,470 and the initials BIL
A Deadpool pinball video screen with the TILT CHAMPION of initials BIL with a BONUS LOST score of 1,538,000,000
A Deadpool pinball machine with a Grand Champion score of 29,240,440,770 and the initials BIL
The Peter Parker Reads A Book meme. Panel 1: Peter Parker reads a book with the title HOW TO RETIRE RICH Panel 2: The inside of the book says WEALTH Panel 3: Peter Parker cries