Brick Stacking

Before today’s piece: This week’s episode of Under The Number is with Benevolent Capital CEO Brett Johnson.

Brett’s portfolio includes Rhode Island FC, Ipswich Town FC, Phoenix Rising FC, Oura, Athletic Brewing, and FlyHouse. Tune in for 40 minutes on how he built a $500 million deal machine.

You know the moment a game swings? That’s where Skybox is right now.

2026 has been a year of brick stacking: laying foundation, building relationships, and earning trust. I’ve learned there are no shortcuts and no substitute for reps.

The biggest hack is that the work is flat out fun.

Matthew Jester has joined Skybox as a Partner.

This is a huge get for us.

Anyone who has talked with Matthew, heard him on Clubhouse, or read his work knows he's one of the best in the business. He's a bloodhound for opportunity, a relentless grinder, and above all, a great guy.

He brings a ton of horsepower to Skybox.

We hit 1,000 followers on October 2 and crossed 10,000 last night. The takeaway has been the importance of appropriately matching content type and surface — LinkedIn, Substack, Instagram, and TikTok are four very different places.

Our viral How NFL Owners Made Their Money series is a short-form video offshoot of The Roaring 20s, repackaged for Instagram and TikTok. The series currently has over 6.5 million views across platforms in 19 days.

Two things can be true at once: there is no reason to get caught up in vanity metrics, and it’s also nice to see more people picking up what we’re putting down.

UP NEXT…

We have more incredible guests, new formats, and live events on the way.

One year ago I was still hosting Under The Number on the side, nearing the end of year three as Chief of Staff at a VC firm and figuring out what would come next.

In November, I wrote my first essay on the Sports Economy. In December, I left the firm. In January, I dove in head first and focused all my time on breaking into the Sports Economy. In March, I announced Skybox. In May, I hired an intern (shoutout Mikey). In July, I launched Clubhouse with Matthew and Dominyck. Last week, I hosted the first in-person Skybox event.

Along the way we’ve published 42 pieces of writing and 54 podcasts, with episodes recorded on location with guests in Phoenix, Dallas, Chicago, Los Angeles, and New York.

Where we’ll be a year from now is anyone’s guess, but I can assure you that our ambitions are aggressive.

Thank you for being here for the top of the first inning. The operators, investors, and builders reading this are shaping the world of sports, media, and entertainment.

Going forward, essays & Field Notes will come from me on Tuesdays and Matthew on Fridays.

See you next week.