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MBW’s Key Songs In The Life Of… is a series in which we ask influential music industry figures about the tracks that have defined their life and career so far. Here, multi-Grammy-winning songwriter and producer, Jack Antonoff, unveils his musical autobiography. The Key Songs… series is supported by Sony Music Publishing.
He’s been a defining influence on the sound of 2025, co-writing and producing most of Kendrick Lamar’s GNX and Sabrina Carpenter’s Man’s Best Friend – with his fingerprints on chart-topping smashes Luther and Manchild.
But when MBW catches up with Jack Antonoff, speaking from a studio in Portugal, it’s not to discuss the hits of today. It’s to talk about the music that made him who he is.
Throughout our discussion of his Key Songs playlist, Antonoff repeatedly returns to themes of authenticity, restraint, and the mysterious alchemy of perfect production.
He’s particularly animated when discussing AI’s limitations in creative fields, likening its ability/inability to write a joke or a moving song to “asking a clown to come over and fix the electricity – two entirely different things”.
“A great joke is in some ways very similar to a great song,” he continues. “Both play with everything happening in your past, present, and future, creating a visceral reaction, something you cannot control.
“People can lie to themselves in politics, in society, about who they are and what they feel – they can put on all these different masks. But you can’t lie to yourself about music and comedy.
“Comedy doesn’t just make you laugh; comedy reveals what you think is funny, whether you like it or not. It’s the same with music. It’s the great revealer of people’s hearts and souls.”
“People can lie to themselves in politics, in society, about who they are and what they feel – they can put on all these different masks. But you can’t lie to yourself about music and comedy.”
These aren’t just abstract theories for Antonoff. His approach to production – whether working with pop superstars or indie darlings – is rooted in a deep respect for the listener.
“There’s zero part of me that thinks ill of the public’s intelligence when it comes to music,” he tells MBW of his approach in the studio, even when sculpting pop hits that stream in their billions.
“I don’t see my work in pop music as being in any sort of service industry,” he adds. “I’m not trying to please. It’s about making something that feels incredible, honest, and worth putting out.”
He’s equally thoughtful about the music industry’s snowballing obsession with artist visibility.
Discussing Fiona Apple‘s genius, he suggests that viewing her quiet public profile as an anomaly in modern music “speaks to how marketing-obsessed we’ve gotten. All that matters is your songs, the way you record them, and the way you perform them.”
Here, in his own words, are the seven tracks that have shaped Jack Antonoff’s journey — from a middle-class childhood in New Jersey through teenage angst, devastating personal loss, and ultimately becoming one of music’s most sought-after hitmakers…
1) The Beatles, Happiness Is A Warm Gun (1968)
When I was young, my parents just played tons of music in the house. My dad is this brilliant ragtime guitar player who grew up in New Jersey and somehow ended up taking guitar lessons from Reverend Gary Davis.
There was really eclectic music in the house, everything from ragtime to British music, music from every generation. Happiness Is A Warm Gun is particularly significant because it’s the first production memory I ever had: I hear everything, and I’m utterly fascinated as to why these choices were made.
I’d always remembered hearing music, loving music, loving melodies and instruments, all these things about songs. But this was the first time thinking: ‘Holy shit, why is that voice coming from this speaker? Why is the time signature changing? Why does the guitar sound like it’s melting?’
“The Beatles were just like a fact. You didn’t fuck with it. It was a fact.”
Obviously, Happiness Is A Warm Gun is one of the greatest productions ever, but all of that jumped out at me – partially because of its brilliance, partially because of its panning, partially because of its oddity in general.
I’m probably nine at this time, becoming acquainted with the popular music of the era – Nirvana, Smashing Pumpkins, things like that.
But in my house, The Beatles were just a fact. You didn’t fuck with it. It was a fact.
My mother was a nurse who’d stopped working to raise us kids, and my father had a company that did carpet cleaning. It was a very normal, middle-class American existence.
The way they raised me, there was everything, and then there was The Beatles.
2) NOFX, The Decline (1999)
I always loved NOFX growing up. But when they put out The Decline… it’s basically like a rock opera. It’s 40 or so minutes, it’s one song and never stops.
At that time, in mainstream culture, politics were [treated as] separate. So a lot of things I was learning about — global politics, race politics, veganism – came much more from underground music. I loved bands like Bad Brains and Propagandhi and things like that.
The Decline connected a lot of interests for me, because there was a theater to it. I still think it would make one of the greatest plays or musicals of all time. I studied it from beginning to end — the way they sewed it together.
“The biggest takeaway from The Decline is the intention for serious listening.”
Listening to The Decline, that’s my root of throwing rules out [in the studio], making really harsh changes this way and that way. I guess that started with Happiness Is A Warm Gun too, but The Decline is a very large-scale version of it.
I guess the biggest takeaway from The Decline is the intention for serious, serious listening. It was almost decidedly fan-only.
Its architecture makes it impossible to have a casual listen, and I think that’s a really important thing for artists.
There’s zero part of me that thinks ill of the public’s intelligence when it comes to music. I don’t know where this narrative [of pop fans not listening as intently as fans of other genres] comes from, but I’m never interested in making anything immediate.
Music and songwriting, recorded music, is a very precious thing and meant to be expressed only at the highest level – even the simplest song. I’ve never understood how anyone could [enter the studio with the intent] to dumb anything down.
Music comes from the heart and the soul; I don’t know how you would even begin to dumb that down. It would be like trying to dry out an ocean; it makes no sense to me.
3) Air, La Femme D’Argent (1998)
This was a time in my life of attempting to escape a very acute state of grief. I started taking drugs, I was on tour a lot, and I was looking for things that really took me away from myself.
My younger sister died of brain cancer when I was 18. It happened around the exact same time that I started to leave home and tour as a musician.
When I think back on it, it was miraculous that I was able to move, let alone tour. But I was living in this very compartmentalized emotional space, trying to live a life on the road while grounded in this grief.
What I know now, that I didn’t know then, is that some things are just too big. I was trying to hold it all in, rapidly moving between complete breakdown and utter escapism.
“In the eye of the storm, I couldn’t articulate it. It was too big.”
Someone put on Moon Safari, which is undeniably a great album, all of its own genre.
As soon as I heard this first song – this plucked bass, very Beatles-esque, but with this ambient thing – I got totally lost in it. This music really transported me.
But the biggest thing, which I think about every day when I’m in the studio: There’s a moment in this song, towards the end, the whole thing is building and building, climaxing, and then right at the tip of the climax, when it’s just about to completely explode, a tambourine enters, doing 16th notes. One instrument. And this tambourine, doing 16th notes, is bigger, more impactful, and more euphoric than a 5,000-piece orchestra.
Whether I’m consciously thinking about it or not, that moment, this song, is such a part of my DNA when it comes to thinking about restraint, moving mountains with something tiny.
Interestingly enough, during that time, I wasn’t able to write very well. In the depths of the grief, the eye of the storm, I couldn’t articulate it. It was too vast.
I had to distance myself from it; time needed to exist before I could express it in songs. Now it’s in all of my writing.
4) Tom Waits, I Never Talk To Strangers (1977)
I love Tom Waits. He’s in my top five favorite songwriters, and he’s lived many different lives.
He’s a great inspiration to try new things. He obviously had his more working-class songwriter phase, then almost like a pirate-sounding phase, a spooky phase.
But it’s when he goes so far into this crooner jazz place… that’s this song – a duet with Bette Midler.
“It reminds me of thinking that I can make a jazz record at the same time I’m making a hardcore record, which is something I still think.”
It’s just amazing that he can do songs like this and do songs like Hold On, do songs like Time, and do songs like Singapore. It gives me a lot of faith.
It reminds me of being young and in love and thinking I could make a jazz record at the same time as making a hardcore record, which is something I still think.
I listened to this a lot in my late teens; a girl I was dating at the time would play it a lot. It’s just one of those pieces of work that reminds you of a person and a place in time.
5) OutKast, Babylon (1996)
With OutKast, it’s impossible to pick anything, because it’s all so brilliant. But for some reason, this song is at the core of their spirit to me.
When I heard it, when I got this album [ATLiens], it was life-changing.
“OutKast and Tom Waits kind of live in the same part of my brain.”
To me, OutKast, much like Tom Waits, treat genre as a jacket to throw on. It’s in no way the centerpiece. The centerpiece is just the heart and soul of what they’re doing.
OutKast and Tom Waits kind of live in the same part of my brain.
6) Fiona Apple, Paper Bag (1999)
In my late 20s, I started to think about engineering and recording on a different level. Sometimes you just hear something that you never forget, and it changes you forever. This is one of those sonic moments.
The song is incredible. The recording is incredible. Obviously, she’s as good as anyone can possibly get.
But when the two drums come in, the panning left and right, the way they bounce off each other, they’re pulling forward, but they’re also so warm. Like that tambourine on Moon Safari, it’s just with me all the time, whether I know it or not. One of those deep sonic references.
“I don’t know anyone who doesn’t listen to Fiona Apple.”
It’s weird [that some people] see Fiona Apple as operating on the periphery of the music business. That’s only out of her choice not to be very present in public promotion, and it’s a view that speaks to how marketing-obsessed we’ve gotten.
Her music couldn’t be less peripheral. It’s front and center – I don’t know anyone who doesn’t listen to Fiona Apple.
To me, she’s an artist who makes brilliant things and needs her space, and that’s not weird. It’s only weird through the lens of everyone being constantly visible.
There’s nothing wrong with being constantly visible, by the way, but you should only do that if that’s something that you don’t mind.
Fiona Apple is just a great inspiration of somebody where all that matters is your songs, the way you record them, and the way you perform them.
7) TLC, Unpretty (1999)
Unpretty is perfect. The recording, the way it kind of moves and floats, I find it very uplifting. It almost feels like a meditation.
I don’t really know why I connect with it so much. The sprinkly, high-end nature of the guitars and the beat – it’s just doing this bizarre, magical thing, and I feel like I’m floating when I listen to it.
“It’s just doing this bizarre, magical thing, and I feel like I’m floating when I listen to it.”
It has a sonic quality that you can’t really dissect.
I don’t remember the first time I heard it, but it’s just always been there. It’s a constant in my life.
Partner message: At Sony Music Publishing (SMP), we believe every voice matters. We are the #1 global music publisher, advancing the artistry of the world’s greatest songwriters and composers for over 25 years. We keep songwriters at the forefront of everything we do, and design our suite of services to amplify opportunities, build connections, and defend their rights. Our roster benefits from an international team committed to providing support at every career stage. From classic catalogues to contemporary hitmakers, history is always being written. We are a part of the Sony family of global companies. Learn more about SMP here.Music Business Worldwide
Most passive real estate investments forecast returns in the 12%-20% range. Some come with high risk, while others come with low or moderate risk. The critical question for investors is, “How can I tell which passive investments come with high risk versus lower risk?”
Risk is only one dimension affecting investment returns. Other dimensions include minimum investment amount, time commitment, tax benefits, personal values, and access for non-accredited investors, among others.
Once you wrap your head around that fact, you can start looking for investments offering asymmetric returns with relatively low risk. Here are a few of the first things we look at in our co-investing club, as we vet deals to go in on together with $5,000 apiece.
Red Flags
In particular, I watch out for these red flags among passive real estate investments.
Short-term debt
Real estate deals fall apart for one of two reasons: The operator either runs out of money or time.
From 2022 through 2025, it’s been a bad market for either selling or refinancing. High interest rates drove up cap rates, which means lower property values.
Operators who took out short-term bridge loans that have come due during this period have run out of time and found themselves in a terrible position. If they sell, they lose huge amounts of money. If they refinance, they also need to cough uphuge amounts of money, since their properties are now worth 25-30% less on average. Read: capital calls or bailouts from supplemental loans.
Floating rates with no protection
There’s nothing inherently wrong with floating-rate commercial loans—if the operator has protection in place against higher rates.
That could mean a rate cap, or a rate swap, or some other way to limit the risk of higher rates. Just make sure the monthly payments won’t go through the roof if loan rates rise, and that the operator’s projections featured the highest possible rate.
No expertise in the asset class or market
In our co-investing club, we want to diversify across many different asset classes beyond multifamily, including industrial, retail, mobile home parks, raw land, secured debt, and so forth. But when we meet each month to vet an investment, we want the operator to be a deep expert in their one narrow niche.
In other words, we want our portfolios shallow and wide, with small investments across many asset classes. But each individual investment should be narrow and deep, with a niche expert operator.
For example, we want to invest with a specialist operator who’s done 30 industrial sale-leaseback deals—not a multifamily operator who’s making their first foray into industrial real estate.
The same logic applies to geographical markets. We want to invest with operators who know a specific market inside and out, with a proven local team on the ground.
First-time local management collaboration
When I first pre-vet a deal, one of the questions I ask is, “How many properties do you currently own in this submarket, managed by the same local team who will manage this new property?”
Operators sometimes brag about being “vertically integrated” and having their own property management and construction teams. I don’t care about that. What matters is how many properties they’ve worked with the exact same teamon managing in the past.
I don’t want to hear an operator say, “We’re expanding into a new market, and we’re really excited about the property management team who will be taking over.” Instead, I want to hear them say, “We own 10 other properties within a three-mile radius, and the same property management team manages all of them.”
Optimistic projections
Every sponsor claims “conservative underwriting.” Obviously, not all of them do. But short of picking through every cell of every spreadsheet, how can you tell?
A few quick items I look at include:
The projected exit cap rate compared to the current local cap rates for this asset type
The projected pace of rent hikes
The projected pace of insurance hikes
The projected pace of labor cost hikes
Watch out for any operator projecting rent hikes faster than 3% annually, or operators projecting only modest insurance and labor cost increases.
I also don’t want to see projected exit cap rates lower than the current market rates for this asset class. Ideally, they forecast returns based on worse market conditions, not current or better ones.
High regulatory risk
If we’re considering a multifamily or other residential investment, we only want to invest in markets with owner-friendly regulations.
I invested in tenant-friendly jurisdictions early in my career. It once took me 11 months to evict a nonpaying tenant. Eleven freakin’ months. When he left, he punched holes in every cabinet and intentionally scratched up the flooring as much as possible. And that’s just one particularly memorable example, among many others.
That said, nonresidential investments can work out just fine in tenant-friendly markets. For example, our co-investing club invested in a boutique hotel in Southern California, which has performed very well.
The only time we’ll make an exception is if the operator has such deep local property management expertise that it becomes a competitive advantage. Our co-investing club once invested in a multifamily property in the tenant-friendly Portland metro area, with an operator who actually started two decades ago as a local property management firm. That investment has done fine—because this operator knows exactly how to navigate the difficult regulations there.
Green Flags
Now that you know what not to invest in, what are some indications of a lower- or moderate-risk passive investment?
A deep track record in the market
I love to invest with sponsors who know their local market and their asset class inside and out, backward and forward.
Several times now, our co-investing club has invested with a sponsor who specializes in Class B value-add multifamily properties in Cleveland. They specifically target buildings servicing cops, teachers, firefighters, and the like. They’ve done dozens of similar deals, all in the same city, where the principal has lived his entire life.
Deep experience with the same management teams
That sponsor I was just talking about?All their deals are managed by the same in-house property management and construction teams.
Long-term protected debt
I couldn’t tell you whether it will be a good market for selling in three years from now. But at some point in the next 10 years, there will almost certainly be a good market for selling.
Look for longer-term debt, which offers the operator plenty of runway to sell when the market is right—not when their short-term debt expires. And, of course, look for some kind of rate protection if they’re using a floating rate loan.
Truly conservative projections
The market shouldn’t have to improve for a deal to deliver on its projected returns. Look for deals where the projected exit cap rate is equal or preferably higher than today’s local cap rates for that type of property. Likewise, look for slow projected rent hike rates (after the initial bump from renovated units, if applicable).
Experience through several market cycles
You can read about the 2008 housing crisis and Great Recession in as many online articles as you want, but unless you lived through it as a real estate investor, you won’t truly appreciate what a catastrophic market downturn looks and feels like.
Operators who have invested through several market cycles will protect themselves from future downturns in a way that newer investors just don’t think to do. Knowing the risks firsthand gives you a greater respect and appreciation for how things can and will go wrong in unexpected ways.
No online courses or textbooks can convey that feeling of losing hundreds of thousands of dollars. As someone who’s been there myself, I want to invest with operators who have also learned those hard lessons firsthand.
Diversifying Creates a Bell Curve of Returns
Even when you check for these and other red flags, all investments come with some risk. You can optimize your odds of success by screening out higher-risk investments, like we do. But if you want a sure thing, buy Treasury bonds for a 4% return.
When you invest in enough passive real estate investments, the returns form a bell curve. For example, I invest $5,000 at a time in 12 to 16 passive investments each year. I have about 40 passive investments outstanding currently. A few will inevitably underperform, while a few others will overperform. Most will deliver somewhere in the middle of the bell curve, typically in the mid-to-high teens.
Over the long term, these investments average out to deliver strong returns. I put the law of averages to work in my favor.
You don’t want to get stuck investing $50,000 to $100,000 in one or two deals a year, and having that one deal go sideways on you. That’s a recipe for lying awake at 3 a.m., chewing your fingernails.
With one or two real estate investments a year, your returns don’t form a bell curve. You get individual data points that could end up anywhere along the curve.
I learned long ago that I can’t predict the next hot market or asset class. So I no longer try to get clever—I just keep investing month after month, in strong economies and weak, bull markets and bears, and sleep easy knowing that the numbers on the page will average out in my favor over the long run.
The IRS has announced some key changes to its income tax thresholds for 2026. The agency is making the changes to account for inflation. The moves will mostly impact wealthy taxpayers, although some folks in the middle class also likely will benefit. Following are definitions of three key types of taxes and explanations of whether — and how — they are changing for the 2026 tax year…
A recent deal we lost raised serious concerns about how far some brokers will go to push others out of the way, even using veiled threats of regulatory complaints. This story isn’t about winning or losing. It’s about what happens when industry professionals start exploiting policy quirks and trust gaps to gain an edge.
And no, I’m not calling for new rules or regulatory intervention. This one’s on us, the broker community.
The setup
We were working with a client on a 3-year fixed conventional mortgage. We secured an approval with a major bank at 3.94%; a competitive rate considering this particular offer doesn’t allow buydowns. The client was happy. Everything was progressing as expected.
Then the curve-ball came.
A few days later, the client said another broker had offered them a 3.89% rate. At the time, that rate didn’t exist in the broker channel. We suspected, and later confirmed, that the competing broker was using a portion of their commission to manufacture a lower effective rate.
We explained the mechanics to the client and offered to escalate the file internally to improve our offer. We were also good to offer cashback. But before the lender responded, the client asked us to cancel the file. We did so promptly.
The FSRA threat
Several hours after cancelling, we received a sharply worded email from the client demanding written confirmation. The message included this line:
“Please provide me with written confirmation that the application you submitted to The Bank on our behalf has been cancelled. Please note that if we do not receive this written confirmation within the next 48 hours then we will regrettably have no choice but to file a complaint with the regulator FSRA: Financial Services Regulatory Authority of Ontario.”
That wasn’t written by a client.
Borrowers don’t usually reference “FSRA” and “The Bank” in precise, broker-specific terms. (The Bank was named and goes by a name only used in the broker community) This was clearly drafted or coached by the competing broker, and it was obvious why.
Understanding the lender loophole
Some lenders only allow one broker to have a file in their system for a given borrower. Once a deal is submitted, no other broker can act on it unless the first file is cancelled.
That’s the system; and it works, most of the time.
But in this case, the competing broker pushed the client to issue a regulatory threat, not to address wrongdoing, but simply to clear the field. Their offer wasn’t better; in fact, we later learned they were approved at 3.99%, higher than our approved offer.
The “3.89%” was smoke and mirrors, achieved by padding cashback into the deal, which we too were prepared to do.
Their strategy worked. The client aligned with the broker who floated the lower number first. Our escalation with the lender was moot.
What’s the real problem?
Losing a deal is part of the profession. No one funds every file. But when brokers start coaching clients to send threatening emails that reference regulators, just to push another broker aside, then in my view we’ve crossed a line.
This wasn’t about a client protecting their interests. This was about a broker using intimidation tactics that masquerade as compliance concerns.
It’s not illegal. It’s not even something FSRA would take action on. But it’s unprofessional. And corrosive.
A message to fellow brokers
To be clear: I’m not asking for new regulations. I’m not expecting lenders to overhaul their policies either. Lenders would rather lose one broker’s loyalty than lose the deal entirely.
This is an issue of professional standards, not policy.
So here’s what I think we, as brokers, can do better:
Stop weaponizing compliance language. If you’re coaching clients to issue FSRA threats just to get a deal released, you’re misusing trust, and abusing the regulatory process.
Be transparent about buydowns. If your offer relies on cashback to beat another rate, say so. Clients deserve to understand the full structure of their mortgage.
Treat competitors like peers, not enemies. You don’t have to like losing, but you do have to act professionally. A quick phone call instead of a demand email can go a long way.
Why this matters, even if the client never notices
To the client, this was just “brokers fighting over my mortgage.” And they got their deal. The lender got the mortgage. No harm, no foul, right?
But internally, it’s a different story. What’s lost is another shred of professionalism, another bit of goodwill among peers. If left unchecked, these tactics chip away at the credibility we’ve all spent years building in the broker channel.
In the U.K., this wouldn’t happen. Everyone, broker or branch, works off the same rate sheet. Cashback and buydowns are off the table. Business is won based on service, execution, and advice, and not with pricing gimmicks.
Final word
I’m not naming names. I’m not crying foul. But I am confident that this was one of many instances where the competing broker used this strategy to win business away from other mortgage brokers.
And I am saying this: if brokers keep using regulatory threats and opaque pricing tactics to edge each other out, we all lose in the long run. We lose the respect that should come with calling ourselves professionals.
This isn’t a policy problem. It’s a people problem.
And it’s one we can fix if we want to.
Opinion pieces and the views expressed within are those of respective contributors and do not necessarily represent the views of the publisher and its affiliates.
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Amazon Prime members are being offered $0.25 Off Per Gallon on Fridays until the end of the year at BP, Amoco or AMPM when you link your account to Earnify. If you’ve already linked your account you will also get the discount.
Our Verdict
Limit of 35 gallons, you can fill up multiple vehicles in one transaction as well. Make sure to price compare to ensure you’re getting a good deal.
Citigroup is starting to realize returns on its investments in generative AI and tech modernization. The $1.7 trillion bank reported that its gen AI tool saved employees 100,000 hours during the third quarter. The bank conducted 1 million code reviews in Q3, up from 220,000 code reviews in Q1, according to its Q3 earnings report. […]
Senior leaders often tell me: “We have a great culture. People here are kind, relational, and genuinely care about one another. But … we’re not very good at giving direct feedback.” They know kindness fuels harmony, but also that harmony can slip into avoidance. Without candor, people don’t improve as quickly as they need to. Frustration festers. Performance stagnates.
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