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Carl Joseph-Black
Carl Joseph-Black

The Dime๐Ÿ’ฐ - Bankruptcy Lessons

I'm not a bankruptcy attorney, but a friend of mine is one at Kirkland & Ellis๓ ‡Ÿ๓ ‡ ๓ ‡ก๓ ‡ข๏ธƒ๓ †๓ †‚๓ „ซ๓ …‡๓ „๏ธ‚๓ „‰๓ …ถ๓ …›๓ „ด๓ „Š๓ …ด๓ …ต๏ธ„๓ „ฆ๓ „š๓ ‡๓ „š๓ †˜๓ „๓ „‘๓ ‡›๓ ‡Ž๓ ‡‡๓ „œ๓ …น๓ „ ๓ „ช๓ †ฑ๓ …๓ …ช๓ ‡’๓ ‡ก๓ „„๏ธ€๓ „š๓ †„๓ †Š๓ „š. So every time I think about catching up with him, I read a few bankruptcy cases to carry a conversation for our catch up๓ ‡Ÿ๓ ‡ ๓ ‡ก๓ ‡ข๓ †พ๓ …ฝ๓ …Œ๓ …Ž๓ …๓ …–๓ …ธ๓ …ฑ๓ …‘๓ †ด๓ ‡จ๓ ‡…๓ …ƒ๓ ‡Ž๓ †๓ „„๓ „œ๓ †ผ๏ธ‚๓ „ป๓ †ก๓ †ฟ๓ †ฌ๓ †๓ …Ž๓ …–๓ †ฆ๓ ‡˜๓ †บ๓ …๓ …น๓ „๓ …Š๓ †ƒ๓ †Ÿ๓ „ฅ๓ „‘๏ธ๓ „‚๓ „ฌ. One bankruptcy was really interesting this year๓ ‡Ÿ๓ ‡ ๓ ‡ก๓ ‡ข๏ธˆ๓ „Š๓ †Ÿ๓ „๓ …˜๓ †ท๓ †ฌ๓ ‡ƒ๓ …’๓ …‡๓ †ฉ๓ …ฐ๓ †ฒ๓ …ฟ๓ „–๓ …๓ „ฐ๓ ‡‘๓ „œ๓ „๓ …œ๓ „“๓ ‡ช๓ …ข๓ „”๓ †ฆ๓ …ซ๓ „๓ †๓ ‡•๓ „๓ …น๓ „น๓ …™๓ „ž๓ ‡€๓ … ๓ †ต๓ †บ๓ †ช and I learned some stuff about it which I felt would be fun to share.

๓ ‡Ÿ๓ ‡ ๓ ‡ก๓ ‡ข๏ธŽ๓ ‡ฎ๓ „›๓ ‡€๓ „†๓ „ฝ๓ …™๓ †ฝ๓ …ญ๓ †’๓ …ž๓ „›๓ …•๓ …Š๓ …ฌ๓ …›๓ „Œ๓ †๓ „ƒ๓ „ฑ๓ ‡Ž๓ ‡Œ๓ ‡›๓ … ๓ †ฅ๓ „ฌ๓ … ๓ ‡๓ †˜๓ …•๓ †…๓ †–๓ „ฌ๓ †€๓ „‘๓ †ฌ๓ †‹๓ …‰๓ ‡ฅ๓ ‡ŽFood52 filed for bankruptcy๓ ‡Ÿ๓ ‡ ๓ ‡ก๓ ‡ข๓ †ฐ๓ „ฝ๓ …๓ …น๓ „ฌ๓ †›๓ „’๓ ‡ช๓ ‡€๏ธŠ๓ …ฌ๓ ‡‚๓ … ๓ †‡๓ ‡ค๏ธ๓ †€๓ „–๓ „ฏ๓ ‡ข๓ …๓ †ฆ๓ „ฅ๓ ‡ฏ๓ …ฎ๓ …๓ …บ๓ ‡๓ †ช๓ †ฆ๓ †‡๓ …ญ๓ …ฃ๓ …ต๓ …ง๓ „๓ †ญ๓ …ง๓ „œ๓ †ผ. The brand you probably know from those beautiful kitchen photos and the cookware you bookmarked but never bought๓ ‡Ÿ๓ ‡ ๓ ‡ก๓ ‡ข๓ …˜๓ †ผ๓ †‰๓ „„๓ †ท๏ธ๓ …Œ๓ „จ๓ „…๓ ‡„๓ †„๓ „‡๓ „•๓ …‚๓ „‡๓ …œ๓ …๓ ‡‹๓ „๓ †ฉ๓ „†๓ …†๓ ‡—๓ †Œ๓ …ป๓ †ผ๓ …ƒ๓ …™๓ …›๓ …๓ „‚๓ †ฃ๓ …—๓ „‡๓ „ค๓ …พ๓ …“๏ธ„๓ …‘๓ †ป. Yeah, them๓ ‡Ÿ๓ ‡ ๓ ‡ก๓ ‡ข๓ †ฐ๓ ‡•๓ †ก๓ ‡…๓ „‘๓ …ป๓ „ท๓ „ธ๓ †–๓ †ฏ๓ ‡ฎ๓ „พ๓ „ท๓ …ฃ๓ „ฃ๓ …ฏ๓ ‡‹๓ „–๓ …‡๓ …’๓ ‡ฃ๓ ‡“๓ „”๓ †๓ …Ÿ๓ ‡ก๓ …๓ …ƒ๏ธ„๏ธŒ๓ „ฌ๓ †ต๓ …ฒ๓ ‡…๓ …ด๏ธˆ๓ „Œ๏ธ‚๓ „€๓ ‡. They filed for Chapter 11 in January of this year and needed money to keep the lights on while they figured out their next move๓ ‡Ÿ๓ ‡ ๓ ‡ก๓ ‡ข๓ …•๏ธŒ๓ †…๓ †Ž๓ …ง๓ „‚๓ „’๓ †‘๓ ‡ก๓ „บ๏ธ‹๏ธ†๓ …ช๓ †–๓ †œ๓ „Œ๓ „ก๓ ‡๏ธ†๓ …ž๓ …‚๓ ‡–๓ † ๓ …‘๓ …–๓ …จ๓ „˜๓ „Ž๓ †๓ †ฝ๓ †๓ „›๓ …ฒ๓ †‚๓ …œ๓ †๓ „š๓ …ƒ๓ „…๓ †ฝ. That money is called DIP financing, and the way they structured this particular deal is what caught my eye.

๓ ‡Ÿ๓ ‡ ๓ ‡ก๓ ‡ข๓ †ฒ๓ †ฃ๓ …Œ๓ †๓ †’๓ †Ž๓ ‡Ÿ๓ ‡Ž๓ …ถ๓ „ป๓ …„๓ †š๓ †ˆ๓ „ ๓ ‡‰๓ †ฏ๓ ‡ง๓ ‡Š๓ …๓ …Ÿ๓ †ก๓ …ผ๓ „ด๓ †Š๓ „ฟ๓ †น๓ „ฎ๓ …ฅ๓ ‡ˆ๓ …Ÿ๓ „›๓ †ฏ๓ „๓ „Ÿ๓ †ท๓ …ฑ๓ „ฑ๓ ‡…๓ †จ๏ธ„Let's get into it๓ ‡Ÿ๓ ‡ ๓ ‡ก๓ ‡ข๓ „—๓ …๓ …ฉ๓ „พ๏ธ‰๏ธ†๓ …ฃ๓ „Š๓ ‡ข๓ †๓ …๏ธ‰๓ †‘๏ธ‚๓ …Œ๓ †ญ๓ „บ๓ …ช๓ †ฒ๓ „ฟ๓ „ธ๓ †ˆ๏ธŠ๓ †‡๓ ‡š๓ „“๓ †ป๓ …‚๓ …ณ๓ „˜๓ „˜๓ †ฝ๓ †š๓ †ˆ๓ ‡”๓ „ผ๓ „ค๓ „ฝ๓ …˜๓ „จ. Here's this week's edition of The Dime๐Ÿ’ฐ.

๓ ‡Ÿ๓ ‡ ๓ ‡ก๓ ‡ข๓ †ฎ๓ ‡‹๓ †ซ๓ „‰๓ ‡ก๓ …ท๓ …ž๏ธŒ๏ธ‹๓ †๓ ‡Š๓ †˜๓ „ฏ๓ ‡ž๓ †Œ๓ †ต๓ †ญ๓ „‚๏ธ€๓ …ƒ๓ …†๓ „ฌ๓ …—๓ ‡™๓ „—๓ …„๓ …„๓ „ ๓ „ต๓ †˜๓ „€๓ †‹๓ …ค๓ †ฟ๓ †œ๓ †พ๓ „ฑ๓ …ต๓ „จ๓ ‡กFirst, What the Hell is DIP Financing?

๓ ‡Ÿ๓ ‡ ๓ ‡ก๓ ‡ข๓ …Ÿ๓ …ฌ๓ „•๓ ‡ฉ๓ ‡ ๓ …ท๓ …ฃ๓ „ธ๓ ……๓ †๓ ‡€๓ …ฅ๓ „›๓ …๓ ‡€๓ ‡™๓ †ก๓ „ค๓ „ฉ๓ ‡ฉ๓ ‡ข๓ „ง๓ †จ๓ †ป๓ „™๓ „ฃ๓ „˜๓ †ง๓ †ฎ๓ „Ÿ๓ ‡Œ๓ „ท๓ „˜๓ „†๓ ‡Ž๓ …๓ …œ๓ „ผ๓ …บ๓ †บDIP

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Carl Joseph-Black
Carl Joseph-Black

The Dime๐Ÿ’ฐ- It's All Connected

You don't work in tech. You don't know what a NAV loan is and you don't care. You're a teacher in Ohio, a nurse in Atlanta, a union electrician in Pittsburgh, a firefighter in Phoenix. You've been putting money into your pension every single paycheck for fifteen years and you're counting on it being there when you retire.

Here's what nobody told you.

That pension? Your state pension, your union retirement fund, your university endowment if you work in higher education, your 401k if you work in the private sector? It is almost certainly invested in private equity funds, venture capital funds, and private credit funds. And those funds have spent the last decade betting HEAVILY on software companies.

The California Public Employees' Retirement System, CalPERS, the largest public pension in the United States with $502 billion in assets, allocates billions to private equity. The Teacher Retirement System of Texas

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Carl Joseph-Black
Carl Joseph-Black

The Dime๐Ÿ’ฐ: Software Ate The World. Now AI is Eating Software.

In August 2011, venture capitalist Marc Andreessen wrote an essay in the Wall Street Journal that became one of the most quoted pieces in the history of Silicon Valley. The title was simple: Why Software Is Eating the World. His argument was that software companies were going to take over enormous chunks of the global economy, and that every industry had better wake up or get eaten alive.

He was right. Amazon ate retail. Netflix ate video rental. Spotify ate the music store. Airbnb ate hotels. Uber ate the taxi industry. Software didn't just show up to the table, it ate everybody else's food, ordered dessert, and asked for the check.

For the next decade, the smartest money in the world bet heavily on software. Venture capital poured in. Private equity firms built entire strategies around it. Valuations went through the roof. A company that could show recurring subscription revenue,

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Jonathan Jackson
Jonathan Jackson

Why OpenAI bought a livestream (you probably haven't heard of) for $150M

๐Ÿ’ก
Two weeks ago, one of the largest media acquisitions of the loudest acquisitions of the year happened: OpenAI bought a livestream show called TBPN for over $100M. It felt worth writing up some thoughts about both the deal, and what it does and does not represent. All thoughts my own, unless they're data points.

What is TBPN ?

A creator-led media startup โ€” a daily, three-hour live tech talk show hosted by entrepreneurs Jordi Hays and John Coogan. TBPN had 11 employees, 58,000 YouTube subscribers, and generated $5 million in ad revenue in 2025. They were on track to clear $30M in 2026. Put a nice media multiple on that ( around 2-4x) and you easily get to $100M+ acquisition price.

Whoโ€™s the audience?

The technology industry: Tech founders, VCs, executives, and the Silicon Valley ecosystem. Itโ€™s a hit there, so capital flows easily, because what the Valley may lack

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Jonathan Jackson
Jonathan Jackson

The $100B PDF: How Paramount Is Fighting Netflix

The story of Hollywood isnโ€™t art. That existed long before (and will long after) this current iteration is transformed. The story of the Hollywood we know, is about studios being bought and sold, and in between, producing things we watched. A lot of those buyers, we would be shocked at. For instance:

In the 1950s, a music label called Decca, purchased Universal Studios.

NBC later merged with Universal, and then Comcast took itโ€”all to say: institutions trade studios like assets, because they are.

The battle for Warner Brothers is about much more than movies, but we donโ€™t have to act like it the first time something like this has happened.

This analysis focuses on Paramountโ€™s case to the Warner Bros. shareholdersโ€”and how a presentation, positioned wellโ€”while Netflix plays the parallel public game.

But to do that, you need a deck that tells people why

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Carl Joseph-Black
Carl Joseph-Black

The Dime๐Ÿ’ฐ- Jamaica is the Financial Innovator of the Decade

It is not every day that one of the most sophisticated financial innovations in the world comes out of a Caribbean island rather than a Manhattan skyscraper, but that is exactly what happened when Jamaica, through Dr. Nigel Clarke, built a catastrophe bond to insure itself against hurricanes. Instead of waiting for international relief, hoping for grants, or borrowing money when the roof is already blown off the economy, Jamaica pre funded its own disaster recovery. In simple terms, the country convinced global investors to take the financial hit if a major storm hits Jamaica, not Jamaican taxpayers. If the hurricane qualifies, Jamaica collects the cash immediately. If it does not, investors get their money back with interest. That is not charity, that is contract law and capital markets working as climate defense. It is finance as survival strategy. This week I get to tell you all about it. Here's this week's edition of The Dime๐Ÿ’ฐ.

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Carl Joseph-Black
Carl Joseph-Black

The Dime๐Ÿ’ฐ - The Unicorn Algorithm

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Carl Joseph-Black
Carl Joseph-Black

The Dime๐Ÿ’ฐ - Fawn Weaver, Uncle Nearest, and the Hidden Powers of Lenders

If youโ€™ve been following headlines, youโ€™ve probably heard about the court filings involving Uncle Nearest, the whiskey company celebrated for honoring the legacy of Nathan โ€œNearestโ€ Green, the formerly enslaved distiller who taught Jack Daniel. But beneath the headlines about culture, brand equity, and leadership, there is a much more technical and sobering lesson for founders: how the very credit agreements that fuel growth can also put your companyโ€™s fate in the hands of lenders. Here's this week's edition of The Dime๐Ÿ’ฐ.

This case is a real-world example of what happens when debt meets default, and why every founder should think twice before signing a loan agreement they do not fully understand. The past few days I've been reading both the complaint by the lender (Farm Credit Mid-America, PCA) and the response by Fawn Weaver. I have attached them below for download so please feel free to

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Carl Joseph-Black
Carl Joseph-Black

The Dime ๐Ÿ’ฐ - How Artists Are Using Holding Companies to Launch Empires

Iโ€™ve been thinking a lot lately about how artists are structuring their empires. Not just deals, not just IP rights, but actual legal entities. As more creatives start looking at themselves like founders, the question isnโ€™t just how to get paid, itโ€™s how to build something that scales, protects, and compounds. One way weโ€™re seeing this play out? Holding companies.

Artists are increasingly launching clothing lines, alcohol brands, production studios, and tech ventures under a central legal entity they control. Think of it as an ArtistCo. One LLC or corporation at the top, with subsidiary businesses beneath it. This isnโ€™t just savvy, itโ€™s strategic, and there are serious legal implications worth understanding.

The Jay-Z Playbook: Roc Nation as ParentCo

Although Jay-Zโ€™s Roc Nation is a subsidiary of Live Nation, it isnโ€™t just a record label, it too is a holding company. Under

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Jonathan Jackson
Jonathan Jackson

Free Agency ๐Ÿ“ˆ- $20M, Joe Budden, and becoming dangerously independent

๐Ÿ”–
Hi! Was traveling last week, but we back! . Joe Budden telling the New York Times how he is making $20M in top line revenue in 2025 is something worth writing about, but not for the reasons you might think.

Transparency in media is rare, but an individual explaining what they make and where it is coming from is unprecedented. I hope we stop talking about things like this like they're "regular" and give them the analysis they deserve. This is my humble attempt.

This is a deep dive, so TL;DR:

โ€ข Know what youโ€™re paying forโ€”Budden trades platform fees for ownership, control, and community tools. Price your independence consciously.

โ€ข Independence is still interdependenceโ€”Joe owns the IP, and is in a healthy relationship with Patreon. Map your dependencies and build exit ramps.

โ€ข Donโ€™t confuse luck with leverageโ€”Buddenโ€™s fifteen-year runway made scale possible. Start where you
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Jonathan Jackson
Jonathan Jackson

Ryanโ€™s World: Obsession, Deep Collaboration, and Deal Terms

No film director in the history of modern film, has grossed more money at the box than Ryan Coogler on fewer than 4 movies ($2.4 billion to be precise). I start here, because what I am going to say next, is something I've been thinking about since Sinners came out.*

The deal he has is not new structure or idea. It is just being presented that way. And it irks me, because instead of actually saying what's possible, people would rather pontificate.

First though, let's hear from Mr. Coogler himself.

0:00
/3:03

Democracy Now, 2025

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Jonathan Jackson
Jonathan Jackson

Free Agency Vol. 28 - On artists, corporate structure, and compounding your agency

Recently, a friend asked for some insight on the business of their art, as they are in the process of working on some new projects. I went back and forth on sharing this, but I think it might help artists and creatives understand why it feels like the ground is shifting beneath them, and how to be more resilient through that. I thought there would be no better example than Universal Music Group: one of the best examples of a business operating at scale around the world, focused on monetizing creativity via artists. Like it or not, they continue to grow, and it's because of the processes they have, and how they utilize them.

I've seen artists get exploited for three reasons: fear, mindset, and predatory frameworks. This piece addresses all three. When I talk to friends about business, I skip the pleasantries - our relationship means I owe them direct honesty. Some details have been obscured to protect privacy.

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