Money with Katie (Katie's Version)
Why I sold—then bought back—my business.
It’s very important to me that you know the most handsome dog on the North American continent is my son:
I’m choosing to focus on this picture today, and not the fact that he got diarrhea in his kennel three (3) times in the middle of the night.
If you didn’t receive the newsletter in your inbox last week and you’d prefer to, check your Substack notification preferences—if you have the app, it’ll likely default to delivering it there, rather than emailing it to you. I, for one, prefer to fight for your attention in the rarefied air of your inbox among the utility companies and Crate & Barrel sale emails.
As promised, today I’m telling my acquisition (and reverse-acquisition) story in more detail for the first time. (Some regularly scheduled programming is underneath, if you aren’t titillated by intellectual property story time.)
If you’re a mentally ill card-carrying inhabitant of the Swiftverse, you’ll recognize the significance of this image immediately.
In May 2025, Taylor Swift announced that she—finally, after years of dramatic twists and turns which included Swift re-recording four of her first six albums—bought back the master recordings of her entire discography. “All of the music I’ve ever made…” she wrote in a barely legible letter posted to her website, “now belongs… to me.”
Forget the fact that you couldn’t have engineered this outcome any more cinematically had you conscripted Nora Ephron to write the ending; forget the fact that we have no way of knowing whether the details I’m about to lay out are true or not. None of that matters. What matters is this: Score this letter to the chorus of her 2010 tween banger “Mine” (You are the best thing / that’s ever been mine), and what do you have? Me, squinting at a phone held two inches from my face whilst on a packed Denver International Airport tram headed to Terminal B, openly weeping on public transportation for my close personal friend Taylor Swift.
For those of you who remain firmly tethered to reality and have not, like me, projected the events of your lives onto the machinations of a particularly relatable billionaire, I’ll summarize quickly: In 2019, Scott Borchetta—the owner of Taylor’s first label, and a father figure of Taylor’s—sold her music to a man suspiciously named after a child’s toy (Scooter Braun).1 Taylor and Scooter had beef.
Taylor, whose talent for songwriting is outpaced only by her talent for Doing Capitalism, immediately turned this routine asset transfer into a larger-than-life saga about ownership and betrayal, and defiantly announced just two months later that she’d be re-recording all six albums with the appendage “(Taylor’s Version),” each including never-before-heard “vault tracks.” This is how we got the vaunted All Too Well 10-Minute Version, the lyrics of which I’m confident I’ll remember on my deathbed after I’ve forgotten the names of my own children and which inspired my own rendition dedicated to my muse2, Harrison Butker.
If you’ve used Bill Gates’s internet or briefly stepped outside your home over the last three years, you know what happened next:
Reputation was the last album Taylor produced with her old label; Lover (a flop for me) was the first one she produced alone. Folklore and Evermore followed, to much critical acclaim from fans and surprised non-fans alike, but far less commercial success than she was accustomed.
In that sense, the re-recordings (which, according to the new Disney+ docuseries about the Eras Tour, are what inspired her to do the Eras Tour in the first place) jumpstarted her career again. Red (Taylor’s Version) reversed a downward sales trend, and her next album, released right before the tour began, set a new record. The re-recording of 1989 became her most popular album to date until her next two albums buried it, and now Taylor Swift is the closest thing we have to a monoculture.
The truly breathtaking part of this reclamation tale is the fact that it almost didn’t happen. Had she been offered her music back in 2019, it’s unlikely she would’ve had the liquidity to afford it. And without the betrayal, there would be no re-recordings, and without the re-recordings, likely no Eras Tour. By re-recording her work and following it up with a record-shattering global invasion tour, she not only degraded the value of the originals (because parasocially challenged fans like me pledged to avoid the Scooter-tainted originals out of allegiance to Taylor’s Versions), but the tour created the cash necessary to buy them from the private equity firm that Braun sold them to. She reportedly paid $360 million.
Even if “Shake It Off” is a song that makes you want to van Gogh your own ears, you have to admit this sociopathic demonstration of “playing the long game” is impressive (a strain of sociopathy that I, for one, have the good sense to respect). The feud also, not for nothing, gave us “my tears ricochet,” a song that features the line And if I’m dead to you / Why are you at the wake?
(Seriously. If you’ve never seen this performance, watch it from 2:13 onward.)
Why am I telling you this story? Mostly because I’ve been looking for a way to shoehorn it in for months as part of my ritual sacrifice to the Swift gods regular business and finance programming, but also because today I’m sharing my own intellectual property ownership story in more detail than ever before. Money with Katie (Katie’s Version), if you will, in three parts:
The Decision to Sell Money with Katie
The Decision to Buy It Back
What Comes Next
The decision to sell Money with Katie to Morning Brew unequivocally changed the trajectory of my life, let alone my career. To understand why I bought it back, you have to understand why I sold it in the first place.
By late 2021, I was earning a total compensation of roughly $140,000 at my full-time job after several strategic jumps between companies (Chapter 2 of Rich Girl Nation is all about how to finagle your way through byzantine HR departments to earn more) and roughly $250,000 per year from Money with Katie on the side. Money with Katie seemed like it might have long-term potential, but it was so relatively new that abandoning my career to pursue entrepreneurship felt short-sighted and impulsive. When Morning Brew called, another path materialized in front of me: one that offered W-2 stability within the business I desperately wanted to operate full-time.3
I remember feeling like things moved quickly. I recently went back to my Google Calendar to confirm the timeline and found my first conversation with Morning Brew’s then-CEO on November 24, 2021. There were four follow-up calls over the next three weeks. Decision made on December 23. I cried and popped champagne the day we signed. The next day I had a terrible migraine, as if the white-hot excitement had fried my nerve endings.
It was what the suits call an “acquihire,” which means Morning Brew bought 100% of my business—its social media accounts, the podcast, email lists, website, branding, customers, and all its intellectual property—and hired me as an employee. (Morning Brew itself had been recently acquired by Business Insider; their four million-subscriber email list, ad business, and intellectual property was valued at a reported $75 million.)
My deal left me with no equity, meaning I owned 0% of Money with Katie until two weeks ago. We structured the original sale price in 2021 like a minimum guarantee to be paid over the course of the contract, with the opportunity for additional payment tied to my performance. (The intent was to create an incentive for me to continue growing the brand. Little did they know an electrifying fear of failure is all the incentive I ever need.)
The company had incubated creator-employees already, but I was the guinea pig for a deal of this nature, which meant two twenty-somethings (one already very experienced with acquisitions, the other decidedly less so) were attempting to value a body of work, my labor, and, critically, what the alchemy of the two might be worth in the future. The original contract covered three years, but gave surprisingly little consideration to what would happen at the end. There was no clause which specified what I’d have to do to get it back; no termination agreement. This was less of a concern for me in 2021 because 2025 seemed so far away as to be another lifetime and, besides, the guarantee was so much more than I figured I’d ever earn. Narrator: She was in over her head.
It just so happened that my oldest brother-in-law, Tyler, was a mergers and acquisitions attorney (arguably the most ‘dumb luck’ element of this entire experience), though in the tech sector. In retrospect, it probably would’ve been worth ponying up for an entertainment or IP lawyer, but I didn’t have the means yet to justify a $500/hour rate. This was classic “penny wise, pound foolish” behavior, and fortunately, it didn’t end up burning me.
Back then, I didn’t know what “intellectual property” was (should’ve been paying closer attention to Taylor Swift), but instinctually I understood that selling my business meant selling control. By the time we reached a consensus on the price and payment terms, the product I handed over felt less like a modest, niche media operation and more like the key to the full, blistering thrust of my ambition. Neither one of us knew what a working relationship of this kind would look like. It felt like tossing my baby over a wall and hoping someone was on the other side to catch it.
The truth is that it would’ve been stupid to turn it down, and with the privilege of hindsight, it was unquestionably the right decision. I got to explore my entrepreneurial proclivities with all the rough edges of risk and uncertainty sanded down. One of the biggest selling points was obvious: I wanted to run a successful media business and I didn’t know anything about how to run a successful media business. Morning Brew, with their four million subscribers and $75 million valuation and teams of salespeople and designers and podcast experts, very obviously did. An entrepreneurially inclined friend asked me the question at lunch one day that ultimately calcified my choice: Would you rather own 100% of a grape or be guaranteed slices of watermelon indefinitely?
For me, that grape was everything—here, you must remember that a shelled pistachio would have been a better analogue for my financial aspirations at the time—but it represented such an infinitesimal percentage of their overall revenue that the product they were buying, I assume now, was proof of concept for the direction they wanted to take their consumer division.
I wrote more about what I wish I’d known then in Rich Girl Nation:
If you find yourself in a situation wherein you’ve created something valuable and someone wants to buy it from you, remember: Everything is negotiable. To the extent you can retain some of your brainchild (whether that’s a social media account, a customer email list, the rights to license back the name, or partial ownership of your business), it’s probably worth conceding something else in the deal if you have reason to believe your business is truly worth something (and why wouldn’t you?!). Here are a few things you might want to negotiate for:
Termination clauses (if they end the relationship, how much do they have to pay?)
The right to access your own customer database if you go your separate ways
Partial ownership of the intellectual property
Control over costs (in other words, the “L” on the P&L statement)
Minimums (that is, you’re guaranteed to take home $X), particularly if your compensation is largely based on factors outside of your control
If selling was the most consequential career decision I’ve ever made, buying it back was a close second.
The fact that I had sold 100% of the business in perpetuity was an inconvenient scrap of information that I typically managed to ignore by filing it away for 2025 Katie, but which became urgent sometime in early 2024 when the end date of the original contract was suddenly visible on the horizon. This time, I knew I needed to negotiate the clause I was incapable of imagining back in 2021 when I was focused on the sale price: that which would allow me to leave someday with Money with Katie in tow. This felt like an inevitability; a “when,” not an “if.” The idea of leaving years of my writing and interviews behind—of “starting over”—was unbearable.
Here’s the thing I hadn’t known in 2021: Being a creator-employee meant near-total creative autonomy and very limited business autonomy. That is, after all, close to the entire point of selling to a much larger operation—you can outsource sales, accounting, revenue strategy, analytics, and customer management to an entity that actually knows how to do those things. This was the original sales pitch, if my recollection of those five conversations is accurate: All you have to do is make the content; the part you enjoy. We’ll do everything else.
The problem, as it turned out, was that I learned later how much I enjoyed doing those other things, too. It was only when I ceased being the decision maker that I realized how much of the fun was being the decision maker.
The “business” element of media solopreneurship is inscrutable and frustrating and thrilling and rewarding. It’s a puzzle: How do you make your operation financially viable? How do you calculate the “return on investment” of your own time? This is an area where, no matter how broadly aligned your financial incentives are, you will always be structurally at odds with your salespeople, who make a commission for selling something they have no responsibility to make exist. It’s natural that these two parties would place a different value on the end result.
This may have been more or less sustainable long-term if I didn’t have the disposition of a chastened Girl Scout troop leader. When someone is signing my checks and measuring my performance and presumably keeping tabs on my working hours and output—all perfectly reasonable components of an employment relationship, particularly a highly compensated one—I police my effort in ways that almost inevitably lead to self-destruction. It feels like I should come with a warning: will bite off more than she can chew, then make it everyone else’s problem.
Of course, it can be true that a deal is a win-win in certain respects while at the same time it’s true that a well-run business typically only acquires an asset when it believes it will be the entity to financially benefit most from it. On one hand, this made me determined to prove a worthwhile “investment,” and on the other left me viscerally envious of that ownership and everything that came with it.
Back to the negotiation: How did we come to terms everyone felt good about? It became clear early on that Morning Brew (and, maybe more accurately, their media conglomerate overlords) could not justifiably give Money with Katie back to me, despite the fact that the value was substantially diminished without the whole “Katie” part, and despite the fact that I asked! Very nicely! On more than one occasion! The thing I wanted most belonged to them, but without me, it was worth less, which created a bit of a prisoner’s dilemma that neutralized much of the leverage either side could’ve otherwise exercised.
We passed each other different proposals for the majority of 2024, a time during which I probably spent $10,000 on lawyer fees that functioned more like therapy than legal advice.4 I’d love to tell you that I played a brilliant game of tactical hard ball, but in reality, it was mostly vulnerability on my part matched by good faith on theirs. Devin Emery, Morning Brew’s president, did significant legwork to find a solution their board could live with, but which wouldn’t create such undue financial burden for me that it would’ve made more sense to abandon the carcass of Money with Katie and start over. Much corporate bullshit and strong-arming was avoided not because I’m a world-class negotiator, but because the president approached my desire to leave with my IP collaboratively, rather than combatively.
Ultimately, we signed another three-year contract running through 2027, structured like an earn-out. I could “pay” for the intellectual property of Money with Katie with three additional years of employment, but with a critical alternative: At the end of each year, I’d have the option to pay out the rest of the time and resume ownership. In July 2025, I gave notice that I’d be paying out the final two years.
To understand why I decided it was time, I have to tell you about a different project: the podcast Diabolical Lies, which I started (along with the business that owns it, Mouthy Media), with novelist caro claire burke last year. Right away, the work had the emotional tenor of the early days of Money with Katie—except this time, I had a partner with whom to share the decisions and uncertainty. Where would we launch? How much money and time would we invest upfront before finding a clear path to viability? There are thousands of culture and politics podcasts; what made this one worth people’s time? At every turn, we made choices that were categorically “bad practice” by the professional podcasting standards I had just spent four years internalizing:
We decided not to promote it on social media and instead rely on word of mouth and Substack’s distribution platform. This is anathema in Podcast Land, especially in the age of the “clip.”
Episodes were between 90 and 120 minutes each (sometimes stretching closer to three hours), and we decided to release only two episodes per month. Most experts will tell you that you need to release at least weekly (preferably twice weekly) to become “sticky”5 to listeners, and anything over an hour is a big ask.
In an age of “chat” podcast supremacy (casual interviews or spontaneous conversations between cohosts), we pursued a format that requires around 30 hours of research and production time per episode.
Rather than pursuing advertisers, we opted to ask our listeners to pay for the show—$8 per month, which is, and remains, a tall order for what is ultimately a single bonus episode.
Finally, we decided to redistribute 33% of our net revenue to aligned causes from day one, rather than reinvest it in the business, which almost guaranteed we’d grow more slowly (and definitely guaranteed we’d personally make less money).
This—and I say this with equal parts confidence and humility—should not have worked. Somehow, it did.
Within three months, Diabolical Lies was earning twice as much revenue as The Money with Katie Show, a podcast that had a powerful media machine behind it. Within six, it had twice as many listeners. Both of these facts made me more confident than I reasonably should’ve been that I was ready to run Money with Katie on my own; that the training wheels and platform I needed in 2021 were ready to come off. (Plus, in 2025, we redistributed $168,000 in revenue to more than 15 organizations, which—much to my own FI-pilled brain—feels even more gratifying than taking home that additional $84,000.6) We launched right here on Substack, and to my knowledge, Diabolical Lies is one of the only “publications” that began solely as (and remains) a podcast on the platform.
When I decided I was going to pause The Money with Katie Show indefinitely but continue publishing writing every week, the move to Substack felt obvious. Much like podcasts, email is a one-to-one medium that operates in the absence of any organizing algorithm, making it particularly hard to grow (or even maintain) interest. This is why enormous newsletters like Morning Brew often grow by using paid ads on—you guessed it—social media. For all the deserved shit we talk about the algorithms, it’s undeniable that writing on a platform designed for sharing is preferable to one where your work exists in a silo.
My plan is to embrace the creative flexibility and newfound business freedom this year and experiment with the newsletter; to find ways to make the coverage and insights on money, culture, and class even more valuable, insightful, and entertaining. In 2025, I spent an average of 12 hours on every issue—reading, checking sources, writing, and editing. I’m excited that I’ll have even more time to devote to that process now. Since the end of 2023, I’ve been working with an external freelance editor named Mallory, and I think the difference in quality is obvious. She’s going to continue editing moving forward.
Ownership of the brand wouldn’t have been necessary to spend more time on my writing and it’s true that reassuming control of the “business” side (selecting sponsors, writing my own endorsements, navigating contracts) has, so far, consumed some of the time I formerly spent producing The Money with Katie Show. But ownership was necessary to do those things in the way I wanted to—to crack open the laptop7 every morning knowing that, for the first time in my life, the primary beneficiary of my ideas, time, and effort is me.
“Autonomy” was the word I kept using when people asked me why it was worthwhile to stick around for the extra year and commit to two years’ worth of payments. It’s a word Taylor uses in her announcement letter, too: “All I’ve ever wanted was the opportunity to work hard enough to be able to one day purchase my music outright with no strings attached, no partnership, with full autonomy.” Billionaires—they’re just like us! Autonomy feels like walking on a tightrope without the net of payroll systems or human resources or upper management beneath you, forces that can be as comforting as they are stultifying. My bet—expensive and risky as it may be—is that you make more worthwhile work without that net.
If you listened to my “Self-Employment Tea” episode a few months ago, you know that I had to prepare for 2026 by sitting down and taking a fine-toothed comb to my strategy for the first time in several years. After filling out our Wealth Planner for 2026 and realizing how my accounts had multiplied over the years, I decided it was the perfect opportunity to streamline: to finally consolidate retirement accounts, recommit to monthly investment automations, and check in to make sure my tax strategy made sense with so many new moving parts.
Given how much progress I’ve made over the last nine years of investing, mistakes have the potential to be far more expensive than they used to be. I asked Adrianna Adams, my CFP® at Domain Money, if we could refresh my plan from 2023 given how much has changed for me—and in doing so, I realized just how much had changed for Domain in the last two years, too. There are a few new offerings I think you’re going to love.
Their planning process encompasses everything you’d expect from a financial planner, plus more comprehensive services that typically involve expensive fee models:
Guidance around stock options (RSUs, ISOs, and other equity-based compensation plans that can have tremendous upside and tax implications)
Strategic tax preparation in the “Strategic” and “Comprehensive” plan tiers—not just filing, but preparation that’s integrated into your financial plan
Prior return analysis to review missed opportunities and how to adjust moving forward
Plus, a gamechanger that I think those of you who reside firmly in the “I just want someone else to tell me what to do so I never have to think about it again” camp: Beginning next month, your Domain Money CFP® will now manage your investment portfolio for you if you’d prefer to hand it off entirely, and still with only a flat fee. No “assets under management” (AUM) fees.
🗓️ Schedule your free consultation now and see if my team of Certified Financial Planners® at Domain Money is a good fit for your goals.
🧠 ADHD can make money management require Herculean effort. To help, Charlotte Cowles got six practical tips from a financial therapist who specializes in ADHD. The two simplest switches: Set a five-minute timer every day to sit down and categorize transactions from the last 24 hours in your app of choice (the specialist recommended Monarch; I use Copilot Money), and simplify your accounts so the relationship between them is easier to visualize. Complicated combinations of credit cards and multiple bank accounts are probably making your life harder than necessary. (I would add one more: Honor your limits in this arena if it’s just not your thing. Hiring someone else is not failure.) The way various mental health afflictions impact our relationship with money feels like underexplored territory. (The Cut)
❤️🩹 Two years ago in January 2024, I began—skeptically!—working with a coach. I hired her partially because I was struggling with how to navigate the decisions described above. I just signed on for my third year and, in the interest of fiscal transparency, I pay $1,000/month for weekly, hour-long sessions. Her role is relatively simple: to help me make choices that don’t just check the boxes on the outside, but feel good on the inside. I’m sharing her with all of you solely because she’s helped me tremendously and, honestly, the last two years would’ve been way harder without her. I don’t receive kickbacks of any kind here, so know that this is a USDA Choice, raw-dog recommendation.
🍼 The central tension of Mamdani’s reign as mayor is, apparently, “what he promises he will do and what the normal laws of political physics would seem to allow,” David Freedlander writes in a recent cover story called “The Making of Mayor Mamdani.” I disagree. The real story here, I think, is the way in which the discourse around his election spotlights the central absurdity of American politics: the supposed “unreality” of things that are already, by all accounts, very real in countries all over the world with far less wealth per capita than the United States. The story came out on December 29. Ten days later from the governor’s office:
Governor Kathy Hochul today announced an unprecedented investment as the next step to deliver affordable, universal child care for children under five years of age across New York State. The Governor will partner with Mayor Zohran Mamdani to deliver free child care for two-year-olds in New York City, in addition to strengthening the existing 3K program to achieve universal care and ultimately, serve all families across the city. (Intelligencer)
👀 Turns out the oil executives are skittish about the whole “take over Venezuela” thing. One investor in the space said that the government would “basically have to guarantee it” in order for them to get involved in the country, and another said—and I quote—“No one wants to go in there when a random fucking tweet can change the entire foreign policy of the country.” At one point, Trump used the word “reimburse.” Hopefully by next week he’ll have forgotten all about this and we won’t have to use hundreds of billions in taxpayer revenue to subsidize the profits of oil companies and energy private equity. (The Financial Times)
In the meantime, this headline made me snort:
🪨 BlackRock is so tired of being mistaken for Blackstone that it dedicated part of its website to explaining that it is, in fact, not Blackstone. Why would a case of investment firm mistaken identity prove so damaging? Because Blackstone is buying single-family homes and BlackRock is not. (BlackRock)8
🙂 I can’t decide if Pluribus is an allegory about artificial intelligence (“destructive but solicitous”) or a commentary on democracy and dissent, but as I finish episode 5, I’m too afraid to read much critical analysis. Does our individuality make us free, or would the world be a better place if everyone could work together for the common good? There’s something frustrating about the pacing I can’t put my finger on, but otherwise, brilliant. (The New Yorker)
🤳 You might find yourself using social media less in 2026—not because of willpower or those dystopian little Brick devices, but because AI is making it boring. “People largely stopped sharing personal moments to feed years ago,” Adam Mosseri, the bespectacled John Mayer-lookalike head of Instagram said, because polished imagery is now “cheap” to produce. (As opposed to Instagram’s heyday circa 2016, when influencer-caliber images were a clear status marker on the platform.) If your feed is just influencers and AI slop, why bother? Lately I’ve been spending most of my social media scrolling time on Reddit. (Business Insider)
🎙️ Debated sharing this piece about podcasting as a career choice because it felt too niche to be widely interesting, but honestly, I can’t stop thinking about it, so here you go. The best lines are a toss-up between describing Brooklyn as “Israel for podcasters” and that “[y]our fans, no matter what, will despise you a little bit. You make a podcast, after all, which elicits understandable baseline disgust.” Please confirm. (The Baffler)
He sold her music to a private equity firm the following year for north of $300 million, so he made a quick buck and moved on. Taylor did not move on!
derogatory
the classic “secret third option”
clearly I got over the fear of paying an exorbitant hourly rate for attorneys
✨ gross ✨
well, most of the time lmao
still a Morning Brew laptop—@ HR, y’all want this back, or?
again, not to be confused with Blackstone!
Adored this. Also have you considered starting another substack where you Katie-splain all Taylor Swift lore? I’d go founding member on that shit.
Loved the transparency here - so interesting and one of the things I find myself often craving at work is autonomy and control, spot on!!