📔 Jeff’s Diary (yes, I’ll let you read it)

I heard two things that inspired me this week that I really want you to hear.

A very successful investor shared a question he asks during interviews. He’d pour a glass of water to the middle and ask “is this half full or half empty” obviously priming for a half full response. Then he’d pour it to the brim and ask “is the glass full?” Which to no surprise, everyone would say yes.

Then he’d pour the water until it was overflowing all over his desk and he’d say “no, now it’s full”. You might think, well that guy's a fucking nut case, and you’d be right…. but in the evening, alone in my hotel room pondering that wild story... he was right.

But it wasn’t about the ceiling people artificially set for themselves (which was what he explained), or as I initially took it, the mentality that enough is never enough…. It was that there WAS more room in the glass.

I realized that if it was a competition, the person who grabbed a dropper and spent the time to examine just how far they can push it to the rim; would’ve gotten the job. And I thought, am I the dropper guy? Will I do what it takes to win?

That instinct feels very nurture over nature. A chip on the shoulder from a rough dad or a dirty spoon from a cruddy apartment you never want to go back to. But no matter where that hunger comes from, if you never cheat, and have a moral compass, no matter what you touch or build or do in life, you will succeed….I promise.

The other thing I heard was from Alan Chang on Harry Stebbing's podcast. It was 530am and I was pushing a sled on the outdoor balcony of the LA equinox (yes this my workout mix) and he said something that made me stop.

In his employee reviews, he would ask if they had a gun to their head, could they have done more. He said most people would say “of course”. And I thought, obviously you could do more if there was a freaking gun to your head.

But in reality, that's solely a founders mentality, and as I was explaining to my uber drive what OWM did and he thought how cool it was and asked how it was going.... my response was, “I burned all the boats.”

I had put the gun to my head and said… I will not fail. I cannot fail. Failure is simply not an option for me.

So if nature didn’t give you that instinct, and you know you are destined for more, you could always force nurture to step in…..

And watch the boats burn. Because that fire will drive you to what you deserve.

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→ The Revenue Shift: Why YouTube’s "middle class" is diversifying away from platform reliance and what that means for your partnership strategy.

→ The Infrastructure Land Grab: Red Seat Ventures acquires Supercast. We are seeing a massive consolidation of the "direct-to-fan" pipe.

→ The Evolution of the Signature Deal: JuJu Watkins and the LeBron franchise. Why "skin in the game" is replacing the flat-fee endorsement.

A new report from TechCrunch highlights a seismic shift in how the internet’s most influential voices view their bank accounts: YouTubers are officially moving past the "AdSense Trap."

As of early 2026, data shows that top-tier mid-market creators are deriving less than 20% of their total income from platform payouts.

For years, the dream was to get "paid by the algorithm," but the reality has become a race to the bottom where creators are at the mercy of fickle platform policies and shifting ad rates.

The most sophisticated creators are now aggressively moving into high-margin physical products, SaaS tools, and direct-to-consumer memberships.

They are evolving from content machines into lean holding companies, which fundamentally changes the game for any founder looking to partner with them.

The traditional "shoutout" model is rapidly becoming a legacy product. As creators build their own moats, the cost of their attention is rising, and they aren't just looking for a check to pay the bills; they are looking for ways to scale their enterprise value.

Instead of approaching these creators with a standard "influencer brief," founders should consider how their own operational infrastructure can serve a creator’s diversification goals. You should be pitching them a joint venture.

Pitch them a co-produced new show, pay for the production, co-own the IP. Think Vybes Villa with Zach Justice.

If a creator is already building a business, there is a path to trade your operational scale for their distribution speed. It’s less about "buying an ad" and more about building a bridge between their audience and a product where they have real skin in the game.

The challenge for most founders is identifying which creators are actually "Operators" versus who is just chasing the next payout. At OWM, we track the talent that is actively seeking deeper business integrations rather than just transactional noise.

The News:
Red Seat Ventures (a division of Fox’s Tubi Media Group) has officially acquired Supercast, the platform powering millions in recurring revenue for the world’s most well-monetized podcasts.

Supercast’s top 10 podcasters alone gross more than $26 million per year in pure subscription revenue.

The Operator Take:
This isn't just a tech acquisition; it’s a vertical integration play. Red Seat already owns the advertising and investment arm; now they own the "direct-to-fan" subscription billing engine.

For a founder, this is a massive signal: The smart money is moving away from "buying ads" and toward "owning the billing relationship."

If a major media entity like Fox is betting on the subscription-first model, why are you still relying on a third-party algorithm to reach your customers? The "one-stop shop" for monetization is the new standard. If you don't own the data and the dollar, you don't own the business.

The News:
USC star JuJu Watkins is fronting the Nike NXXT Gen line alongside LeBron James.

While she remains a paid ambassador, the structure is unique: she is deeply involved in the design DNA of the product, creating a signature feel within an established franchise.

The Operator Take:
This isn't just about a logo swap—it’s a pivot toward Skin in the Game.

JuJu is an ambassador, but by being an "author" of the product, she creates more upside for herself based on the performance of the line.

There is a lesson here for the startup world: The most effective partnerships happen when the talent is more than just a face. When you provide a partner with the ability to influence the product and share in the performance upside, you move from a transactional relationship to a structural one.

It’s not about giving away the farm; it’s about ensuring that when the partner wins, the company wins bigger.

➡️ Follow me on LinkedIn for the unfiltered takes I can't fit in this newsletter.

➡️ Forward this to another founder who's struggling with creator partnerships. Ownership spreads one conversation at a time.

➡️ Need 1:1 guidance? Block time with me any Friday here. No pitches, just real talk.