Legacy Elephants

This past spring, two announcements landed in my feed a few hours apart.

The first was Josh Kushner launching Thrive Eternal, a permanent capital holding company that will be concentrated in a small number of assets that Thrive can own and steward over many decades, with the San Francisco Giants as its first deal. The second was HOF Capital, a firm whose portfolio includes OpenAI, SpaceX, Anthropic, and more, leading a consortium to buy Porsche's minority holdings in Bugatti Rimac. HOF said it wanted to help cement Bugatti as an "n-of-1 company for generations to come." 

Then, this past summer: 

• August 11. Ari Emanuel's company Mari agreed to buy ATG, a deal estimated at $6 billion. It gives him control of seven of Broadway's 41 theaters, in a market that rarely sees theaters change hands.

• August 12. Kushner and former Disney CEO Bob Iger announced they were buying the Los Angeles Lakers for a record-breaking $12.5 billion.

• August 21. Marc Stad, founder of Dragoneer Investment Group (shop that runs VC, PE, and publics strategies) took control of the Timberwolves and Lynx in a deal that values the team at $4.5 billion.

• September 3. Vinod Khosla, founder of Khosla Ventures (VC firm with $15B+ AUM), bought the Seattle Seahawks for $9.6B which is by a mile the most expensive NFL team sale.

When I see three of something in a week, I always stop to figure it out. This was six in a few months!

Call it a barbell

Tech money buying sports teams isn't new. Joe Lacob was a VC at Kleiner for over two decades before he and his partners bought the Warriors in 2010.

What's new is the structure, and the way these investors are talking about it. Kushner runs two different vehicles: Thrive Capital, which holds OpenAI and Stripe, and Thrive Eternal, which holds a stake in the Giants and now the Lakers. Different fund, different LPs, same founder, same thesis. HOF holds Anthropic on one side and Bugatti on the other.

One side holds companies that can 10x in a year. The other holds sturdy assets that are part of the cultural bedrock, and which have existed for many decades.

Two paths after slop

Kushner answered "why now" in his own announcement. Thrive Eternal will back "assets with qualities that cannot be replicated by technology."

Culture has split onto two paths. In the first, anything new comes with a question attached. Is this video real or AI? Is this song a person? Did this reviewer exist? Am I getting punked? On the second are the things that are so real we wouldn’t dare ask like Tom Brady winning 7 Super Bowl rings over 23 years. We know what we saw in front of our eyes. The Patriots winning streak (and then the Chiefs winning streak) are not AI-generated and cannot be manufactured by a prompt. 

Hyper-growth gets a crazy multiple for what a company might become. Legacy gets one for what it already was. (The middle gets neither!)

The same retreat is happening on the culture side. Hollywood is making its umpteenth Marvel movie and four separate Beatles films. For better or worse, we keep returning to the back catalog because it's one of the very few parts we still trust.

Legacy elephants

In 2023 I wrote Elephants, Not Unicorns. The traits I listed included members instead of customers, exceptional memories, and longevity. Another was that elephants are real: you can see and touch them, which you often can't say about a unicorn. I was writing about startups, but many of these traits also describe the cultural institutions and brands described above. 

The Lakers, Broadway, and Bugatti are legacy elephants:

• Members. The season-ticket holder who has spent more than they'd admit to their accountant. It’s part of their identity to be a Broadway lover. (Speaking from experience, this is me!)

• A brand world you recognize from across the street. Purple and gold. The horseshoe grille.

• A place you physically go. Madison Square Garden. A Broadway theater. 

• Often, a face. Kobe, Tom Brady, or sometimes the public face of a brand (Tom Ford).

• Memory. The output of these brands and experiences lives in us for a lifetime.

Where we fit

I'm not buying the Lakers. Park Rangers invests at pre-seed and seed. But the investors on the right side of this barbell are paying for something that took generations to build, and somebody had to build it first. 

When we invest at pre-seed and seed, we look for the younger version of this: a founder building something truly generational that will still be around twenty years from now. That often means putting community before scale, obsessing over engagement and longevity, sometimes building a physical presence for the brand, and being willing to be the public face of it. At the earliest stages, you can get that asset at a price that doesn't include the memory yet because the memory hasn't happened.

Healthy stewardship

Kushner and Iger called themselves “stewards” of the Lakers. Mari said it plans to be a "long-term custodian" of the ATG venues. Time will tell if they choose to make these long-term investments or quick turnaround plays… I’m hoping for and voting for the former.

I have to mention that some of the behavior doesn't match the vocabulary. Mark Walter owned the Lakers for less than a year, and his return was roughly 21%. Lore sold control of the Wolves barely a year after his purchase was finalized. Thrive Eternal was part of a controversial, quickly scrapped plan with FIFA to sell private stakes in upcoming World Cup tournaments. 

That matters because these assets are worth what they're worth because of the generations of fans that came before them. A fast way to destroy that value is by running these businesses purely on a P&L, which may result in pricing fans out of the building or turning the U.S. Open into a corporate lounge. The new owners who will win on this end of the barbell will be those who always remember why the legacy cultural artifact was worth buying in the first place.

Elephants never forget.

This newsletter is brought to you by…

Sydecar: Sydecar is the simplest way to run venture deals, from SPVs to funds. They handle all the back-office work so you can focus on finding and winning the best deals. Thousands of emerging managers and investors trust Sydecar to manage their capital operations seamlessly. Get started at sydecar.io/partners/trailblazers.

Beehiiv: Beehiiv is the newsletter platform built for growth. Whether you're just starting out or scaling to millions of subscribers, Beehiiv gives you everything you need to publish, monetize, and grow your audience in one place. Use code TRAILBLAZERS30 for 30% off your first 3 months at beehiiv.com.

Granola: Granola is the AI notepad that turns your meetings into structured, actionable notes without a bot joining your call. It runs quietly in the background, captures everything, and lets you guide the output so you always get notes that actually reflect what mattered. Get 3 months completely free at granola.ai/trailblazers.

Hex: Hex is the modern data workspace where teams go to explore, analyze, and share data, all in one collaborative platform. From SQL to Python to AI-powered insights, Hex makes working with data fast and intuitive for everyone on your team. Start your 30-day free trial at hex.ai/trailblazers.

Wispr Flow: Wispr Flow is the AI dictation tool that lets you speak your thoughts and instantly get clean, formatted text anywhere you type. Whether you're drafting emails, writing docs, or messaging your team, Wispr Flow is 3x faster than typing and learns your voice over time. Get 1 month completely free at ref.wisprflow.ai/trailblazers.

Kalshi: Kalshi is the first federally regulated prediction market where you can trade on real-world events, from economics and politics to tech and culture. It's a smarter way to put your convictions to work. Sign up at kalshi.com/r/TRAILBLAZERS and get $10 when you trade $10.