Playing Field Brief


Good morning ! Congrats to all of the Boston Marathon runners and a special shoutout to our PF Insiders who participated. It’s always a fun day in the city but even more fun this year with the Sox clinching the ALCS that night. Anyone see that Alabama game?! From Kyrie to Gruden there’s been plenty going on off the field as well. This week in the Brief: We make a pit stop with Busch, Jay-Z has 99 things going on and Big Ramy's winning flex. Go Bucs!

“The first step to achieving your goal, is to take a moment to respect your goal. Know what it means to you to achieve it." - The Rock


This week I sat shotgun with 2x NASCAR cup series champion Kyle Busch. After following in his brothers footsteps as a driver since the age of 13, Kyle went on to have a historic career for himself. He now owns Kyle Busch Motorsports which consists of three teams and 7 Cup Championships. Off the track Kyle co-founded Rowdy Energy (“Kyle10” for 10% off) as a healthier alternative to the big name energy drink brands. Kyle and his wife Samantha publicly support infertility initiatives through the Bundle of Joy Fund.

Listen Here: Kyle Busch Interview

What are you up to? - ben@playingfield.com


  • The impact Muhammad Ali had on the world outside the ring is well documented but his experience helping a failing art studio in the 60's is less known. This week a collection of Ali's paintings sold for $1M at auction. - Ali NFTs next?!

  • The New York Giants partnered with Yieldstreet in the first ever agreement between an NFL team and an alternative investing platform. In the NBA, the Jazz and Lakers both announced new partnerships with banking firms. 

  • Driven by the success of teams in markets with high Latino populations the NHL is exploring opportunities in Mexico. The league will likely set up exhibition games to test out the idea. Auston Matthews supports the idea given his Hispanic heritage.

  • Jay-Z donated a special painting to the Rock & Roll Hall of Fame and made three significant investments this week. He backed a cannabis startup called Flowhub, a blockchain tech incubator and pledged $1M to support wrongful convictions.


  • Bryson DeChambeau invested in a $3M seed round for smart training company Proteus Motion. He decided to invest after seeing the brands Instagram ad. Bryson made his Professional Long Drive debut last week. - I’ve tried Proteus, cool machine!

  • LeBron James is the newest investor and brand ambassador for at-home fitness company Tonal. The $1.6B startup is backed by a long list of elite athletes including Steph Curry, Serena Williams and Drew Brees.

  • Milwaukee Bucks owner Jamie Dinan and soccer legend Gianluca Vialli are filing to raise $250M for a sports-focused SPAC called Iconic Sports Acquisition. Dinan also serves as chairman of York Capital with $12.7B AUM. - Bucks repeat?

  • Manchester United owners Kevin and Edward Glazer caused the team's stock price to fall nearly 13% after selling off $164M worth of shares. In other Premier League news, a Saudi Arabian wealth fund acquired Newcastle for $400M.



  • ESPN and adidas teamed up to create two editions of Top Ten Hi shoes in honor of Sportscenter. In other shoe news, Reebok is hosting their first ever UNLOCKED Week to reward loyal customers with exclusive product drops.

  • Canada Goose is officially getting into the footwear space with the upcoming release of a high-top snowboot and a hiking boot. The brand partnered with Romeo Beckham for the first marketing campaign. - Excited to check these out!


  • Despite receiving a lifetime ban from baseball 1989 for alleged gambling, Pete Rose is launching his own sports-betting podcast called Pete Rose's Daily Picks. Also, ESPN launched a new college basketball podcast called Bald Men on Campus.

  • Netflix released the first teaser for Colin Kaepernick's upcoming scripted-series Colin In Black & White. The six-part show will tell the story of Colin's obstacles as a black adopted child to a white family and the adversity he faced on his journey to the NFL. 


  • The Rock can add music to his long list of career endeavors after having his own rap verse in a new Tech N9ne song callled Face Off. The Rock doesn't see this as a long-term career move but would love to do it again. - This actually isn't his first song

  • Snoop Dogg teased a collaboration with Eminem for his new album which puts an end to a years-long beef between two all-time greats. In other Snoop news, Tom Brady told a great story from a Super Bowl after-party on Jim Gray's podcast Let's Go!


  • I’ve been doing Pilates now for 10 years and it’s been a game changer for my overall well-being. I highly recommend giving it a try. Here’s a few links to check out. Try adding weights if you want an additional challenge. - These weights

  • Eating carbohydrates is normally viewed as a cheat meal that will lead to weight gain but many people overlook the benefits of carb-cycling. Since carbs are vital for energy and brain power it's best to regulate intake based on physical activity in a given day.


Vanmoof V: $3,600

  • Join the waitlist for Vanmoof's newest high-speed electric bike

  • Features two-wheel drive, a full suspension frame, advanced acceleration and next-gen tech

Charmar Cap: $139

  • Handmade in Germany, this cap from A Kind of Guise is covered in a campfire-inspired check print

  • Crafted from wool and lined with mesh with an adjustable buckle back tab

Grovemade Brass Pen: $80

  • Uses high quality Schmidt P8126 rollerball inserts, providing smooth writing for life

  • Single piece body built to last a lifetime, hand polished to develop a distinctive patina over time


  • In honor of October baseball Pepsi and Cracker Jack made a caramel, popcorn and peanut flavored soda. Only 2,000 limited-edition cans were created and the only way to get one is to enter the #PepsiSingToScore Sweepstakes on Twitter. - Gross

  • A few years ago I ran the Ice Marathon in Antarctica to support Polar Bears International. An important part of the foundation's history is the Tundra Buggy One. Enthusiasts are actively voting for the buggy to become an official LEGO set.


Boston, MA: $3,750,000
Biega + Kilgore Team

  • One block from Union Park and steps to the 8-Streets neighborhood

  • Stunning 2018 new construction triplex with parking, rear deck, and roof deck in Boston's South End

Los Angeles, CA: $5,300,000

  • Perched in the Moreno Highlands offering the very best indoor / outdoor living experience

  • Features a library, media room, wine cellar and detached studio

Austin, TX: $5,250,000

  • Gorgeous contemporary hacienda residence on the 12th green of the Spanish Oaks Golf Course

  • Offers gate security, hike and bike trails, spa, pool and 5-car garage


  • JetBlue announced their new Mint 2.0 suites that consist of memory foam beds and closing doors. They were designed specifically for Mint customers preference. The suites are currently available on select flights from NYC to LAX and London.

  • Mandarin Oriental will open it's first residence-only property in Beverly Hills next year with all 54 units featuring outdoor space. Michelin-starred chef Daniel Boulud is handling the restaurants at the property which will be available for in-home dining. 


Chris Pronger and his wife Lauren founded Well Inspired Travels to provide access to memorable and luxurious trips for your entire family. From one athlete to another, WIT understands the travel needs and challenges of elite athletes and their families

Well Inspired Travels is THE premier boutique luxury travel company specializing in curating best of the best experiences for elite athletes, entertainers, C-level executives and business owners. They are excited to help you plan your next trip!

Listen HERE as Chris and I discuss the importance of a curated travel experience.

One&Only Portonovi | Montenegro

  • Acres of sprawling resort overlook a coastline of mountain vistas and calm waters

  • Activities include sports and yoga, spa treatments and pool club cocktails

The Ranch at Rock Creek | Montana

  • One-of-a-kind single bedroom suites to five-bedroom homes are woven into the The Ranch’s vast landscape

  • Features extensive amenities, inventive cuisine and over 40 outdoor activities


  • Mamdouh “Big Ramy” Elssbiay became the first non-American since 1997 to be crowned Mr. Olympia. The competition is the most prominent bodybuilding contest in the world. The winner takes home roughly $400K of the $1.6M prize pool.

  • The fastest 8-person chairlift in North America is coming to Sunday River resort in Maine. The Jordan 8 lift features heated seats and weather blocking bubbles. It will give the mountain a 33% increase in uphill capacity and a 25% increase in speed

  • Formula-1 announced they are developing a 100% sustainable fuel by 2025. The fuel will be 'drop-in' which means it can be used in all current engines without requiring modifications. F1 hopes to one day scale up production for widespread public use.

  • NFT Rundown: Powered by EtherStrikeBundesliga is the latest league to join Sorare's fantasy gaming platform. Dolce & Gabbana sold out their nine-piece NFT collection for a record $5.7M and a mural of Kanye West in Chicago is being auctioned off as an NFT.


  • On October 4th Facebook, Instagram and WhatsApp had their most severe outage to date. One website benefited greatly from the unexpected stoppage. On that day Pornhub's traffic increased by 10.5% which is nearly 500K people per hour.

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Have a great rest of your week! - Ben and the Playing Field team

Playing Field, LLC
105 Newbury St. 4th Fl. Boston, MA 02116 ben@playingfield.com
Playing Field
Ben Rawitz

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