Wells Fargo expects its 2025 gross expense savings to reach $2.4 billion by the end of the year, bringing its total savings from 2021 to 2025 to $15 billion. These savings allowed the $2 trillion bank to largely increase its spend, effectively creating a better and stronger bank over time, Chief Executive Charlie Scharf said […]
Key Points
Tax-loss harvesting is the practice of selling investments that have dropped in value to realize a capital loss, then using that loss to offset capital gains from other investments or up to $3,000 of ordinary income per year.
The idea is simple: You’ve already lost money on paper. Selling that investment allows you to record the loss now and reduce your current tax bill. You can then reinvest the proceeds in a similar (but not identical) asset to stay invested.
It’s a legal, IRS-approved strategy – when used carefully.
Imagine you bought 100 shares of Stock A for $5,000. Today those shares are worth $3,000, meaning you have a $2,000 unrealized loss.
You also sold Stock B earlier this year for a $2,000 gain.
If you sell Stock A, you can offset the $2,000 gain with your $2,000 loss—making your net capital gain $0.
If you have no other gains, you can deduct up to $3,000 in losses against ordinary income this year. Any leftover losses can roll forward to future years until they’re used up.
You can use The College Investor’s capital gains calculator to estimate your taxes if you don’t do this!
Many robo-advisors include automatic tax-loss harvesting as part of their advisory services. But if you’re interested in implementing tax-loss harvesting on your own, the good news is that it’s a relatively simple process.
Take the time to monitor your portfolio for investments that are losing value. When you notice a substantial drop in your investment’s value, it may be time to consider implementing a tax-loss harvesting strategy.
When you find an investment that has lost value, you can sell it. At that point, you will realize a capital loss. Without the action of selling the investment, the capital loss remains unrealized and you miss out on the chance to harvest the tax losses.
For example, let’s say you invest $10,000 into a mutual fund. Six months later, the investment’s value has dropped to $8,000. If you miss the chance to sell your investment and it rebounds to $11,000, you won’t be able to use the temporary loss in value to reduce your tax liability.
Once you sell your original investment, it’s time to reinvest your funds. When you select a new investment, you’ll need to make sure that you are purchasing something similar but not identical.
The IRS will not allow you to pursue tax-loss harvesting if you purchase identical investments, otherwise known as a wash sale. A similar investment cannot be “substantially identical” to the original investment.
However, it’s possible to purchase different ETFs that target similar industries. Buying a similar investment will allow you to stick with your overall investment goals while taking advantage of short-term losses to minimize your tax drag.
Once you’ve completed the mechanics of a tax-loss harvesting transaction, the next step is to claim the loss on your tax return. This final step will allow you to realize the tax loss in a meaningful way.
Depending on your capital gains tax bracket, you could save thousands with the help of this tax minimization strategy.
Although tax-loss harvesting can be an exciting way to potentially save thousands, there are some limitations to be aware of. These limitations have been set by the IRS as a way to prevent abuse.
The wash sale rule prevents investors from attempting to harvest tax losses with identical investments. Under this rule, you cannot claim a capital loss on the sale of a security against a capital gain of the exact same security.
With that, you cannot buy and sell identical securities within 30 days before or after the sale to claim a capital loss. If you move forward with the buying and selling of identical securities within 30 days, the IRS will not allow you to claim a tax write-off.
Importantly, you can replace investments with similar mutual funds or ETFs. With similar mutual funds, your investment portfolio can be relatively similar without violating the wash sale rule.
Important Reminder: The wash sale rule doesn’t currently impact cryptocurrency. If you’re holding your crypto, you can “wash” your crypto to realize tax losses while still holding the same amount of tokens.
Tax-loss harvesting is only possible in taxable investment accounts. Other investment accounts that are tax-deferred, like an IRA or 401(k), won’t benefit from tax-loss harvesting as are they aren’t subject to capital gains taxes.
There is no limit to the amount of investment gains that can be offset with tax-loss harvesting. However, there are limits to the amount of taxes on ordinary income that can be offset.
As a married couple filing jointly or a single filer, you can realize up to $3,000 of capital losses to reduce your ordinary taxable income in a given year. If you’re a married couple filing separately, then you’ll only be allowed to claim up to $1,500 of capital losses in a given year.
Due to these limitations, there may be certain years that you have more capital gain losses than you can claim on your tax return. The good news is that you can carry these losses over to future tax years.
If you’re aiming completing a tax-loss transaction each time one of your investments lose value, the strategy could become burdensome in multiple ways.
First, you may incur transaction costs if you don’t have a commission-free stock broker. And, second, frequent tax-loss harvesting could lead to higher tax prep costs when it comes time to file your return.
Before implementing tax-loss harvesting in your own portfolio, weigh the costs of completing the transaction and filing your taxes. You don’t want to go through the effort of harvesting a tax loss if the costs would outweigh the savings.
As you consider tax-loss harvesting, don’t prioritize this strategy over the value of a well-balanced portfolio. Although you can save on your tax bill through this strategy, it shouldn’t take precedence over building a portfolio that aligns with your investment goals.
If you’re starting out on your investment journey, take advantage of our free resources to help you build a portfolio that works for you. And if you’re looking for a “set it and forget it” tax-loss harvesting option, you may want to open an account with one of the top robo-advisors that can execute all the transactions automatically on your behalf.
Can I use tax-loss harvesting for cryptocurrency?
Yes, crypto losses can be harvested—cryptocurrencies are considered property by the IRS, not securities. However, note that wash-sale rules don’t currently apply to crypto (though Congress has considered changing that).
Does this work for mutual funds and ETFs?
Yes, as long as they’re held in taxable accounts and the replacement fund isn’t substantially identical.
Can I harvest losses in my 401(k) or IRA?
No. Gains and losses inside tax-deferred or Roth accounts aren’t realized for tax purposes.
What if I have no gains this year?
You can still realize losses. They can offset up to $3,000 of ordinary income this year, and unused losses carry forward indefinitely.
How much can I save?
Savings depend on your tax bracket. For example, harvesting $5,000 in losses could save about $750 if you’re in the 15% capital gains bracket.
Do I need a financial advisor for this?
Not necessarily but a tax professional can help ensure trades are executed correctly and losses are reported properly.
Editor: Clint Proctor
The post Tax Loss Harvesting: A Step-By-Step Guide appeared first on The College Investor.
Genting shares surge on improved New York casino license prospects
Being in the C-suite is a high-pressure job with long hours, board responsibilities, and intense scrutiny. But what is it like to be a top executive when you’re off the clock?
Fortune’s series, The Good Life, shows how up-and-coming leaders spend their time and money outside of work.
Today, we meet Malik Ducard, the 52-year-old chief content officer of Pinterest: the go-to social media platform for 578 million creatives.
Long before Ducard became executive at the website curating aesthetic feeds, platforming DIY how-to’s, and cultivating niche communities, he was already all-in on his passion for blending technology with content. As an elementary school kid raised in the Bronx, Ducard discovered his love for creating documentaries, dramas, and comedies with his VHS video camera. The leader was determined to merge his creativity with the medium of the time, whether that be storytelling through paper flipbooks or learning to program on his Commodore 64 computer.
And Ducard would later pour his imaginative zeal into his many stints across MGM, Lionsgate, Paramount, Google, and YouTube, where he held senior roles. He tells Fortune he’s proud to be one of the leaders who launched and grew YouTube Kids: an app in which his own child was able to trial.
Pinterest’s revenue hit 17% growth year-over-year with its net income reaching $38.76 million
Over his three decades in the business world, the Pinterest executive made his mark on marketing, big-screen entertainment, and educational content. Now, his focus is set on making Pinterest the very best social media platform for its 578 million users.
Last quarter, Pinterest’s revenue hit 17% growth year-over-year with its net income reaching $38.76 million. Ducard says more than half of the website’s users are Gen Z—and surprisingly, around 80% of its members live outside the United States. There’s a secret ingredient that makes the business so special, Ducard reveals; it’s battling an “authenticity deficit” in a social media landscape full of clout-chasers and covert ads, as Pinterest has differentiated itself as a “place for fulfillment and ideas, not followers.”
“The bottom line: our model of positivity is working—and setting us apart in an online world that too often incentivises toxicity and rage-baiting,” Ducard says. “We’re proud that we’re a place young people, especially, come to as an oasis of calm and inspiration.”
By platforming industry experts and passionate entrepreneurs, Ducard is helping Pinterest expand into new arenas. The business just launched its first co-branded product as a platform: it created a Pinterest trend-inspired coffee blend with entrepreneur and creator Emma Chamberlain. It also worked with Colman Domingo’s stylist duo Wayman and Micah for curated content boards that inspired his Met Gala red carpet looks. When he’s off the clock, Ducard still pursues his love for creativity and tech—whether that be 3D printing in his downtime, or pushing the boundaries of his dresswear.
Fortune: If you have children, what do your childcare arrangements look like?
I have three Gen Z kids—23, 20, and 17. We aren’t empty nesters just yet, but getting closer to it, and childcare arrangements are less of a thing now. And as they get older, I really am appreciating that I feel like we’re moving from a phase where Dad and Mom know close to nothing in their eyes to—they are proactively seeking advice and counsel.
What are your living arrangements like: Swanky apartment in the city or suburban sprawling?
I live in Los Angeles, pretty much in the middle of the city. We’re in a little pocket that sometimes feels like it’s hidden in plain sight. It’s not swanky, not sprawling, it’s just right. We’ve been here in the same place for over 17 years.
I carry a wallet. In it, I’ve been carrying the business card of a boutique toy store owner. One of my hobbies is 3D printing and I design little games and toys…The business card is a reminder to close the loop with her when it’s ready.
How do you commute to work?
I work remotely and travel to our office in San Francisco, as well as visit our temporary office in Los Angeles. I drive my electric car to work.
Do you carry a wallet?
I carry a wallet. In it, I’ve been carrying the business card of a boutique toy store owner. One of my hobbies is 3D printing and I design little games and toys. A toy store owner said she wanted to sell one of my designs—I had shown her a prototype of a mechanical tic-tac-toe game I invented. The business card is a reminder to close the loop with her when it’s ready.
What’s the one subscription you can’t live without?
Guitar Tab app; I get notation for songs I play on my guitar. Also, ChatGPT, Shapr3D CAD design, and the Sunday New York Times paper.
Where’s your go-to wristwatch from?
Garmin Health GPS watch.
How do you get your daily coffee fix? If you have it at home, what coffee machine do you own?
Jura.
What’s your go-to coffee capsule?
I use different coffee beans—I have no one favorite, I like to try different ones.
If you grab it out, where? And what’s your typical order? Do you grab breakfast with it?
Blue Bottle, cappuccino with oat milk. I’ve recently found a cafe when I was traveling in San Francisco: Nirvana Soul. My new travel favorite where the barista hipped me to cappuccino with macadamia milk—spot on good. I typically make my breakfast; Fried egg and toast; periodically with avocado. A little pepper, dash of salt, sometimes mixed with chopped red and green peppers. Very satisfying and a good protein punch for the day.
How many coffees do you have a week?
15 to 20.
How often do you eat lunch out during the week?
1 to 2 times a week, I do more coffees throughout town.
Where are your go-to places to grab food on the go?
Hilltop Cafe in Los Angeles. It’s the cafe of producer and actress Issa Rae.
Where would you go, and what do you order if it’s a sit-down meal with a client or peer?
Akasha in Culver City in Los Angeles: burger or branzino.
Where do you buy groceries?
Whole Foods.
How often in a week do you dine out versus cook at home?
About half and half; half-cook, half-order or eat out.
Where do you shop for your work wardrobe?
Coming to work at Pinterest, I had to raise my game—because, Pinterest. More colorful, more surprises, but not trying to be something I’m not. It’s actually brought out the ‘me’ more: more self-expression, less of ‘That will never work on me,’ and more of ‘Let me see how that will work on me.’ And I’m wearing brands based on how they look and feel, not just on the label.
What would be a typical work outfit for you?
Jeans, soft collared shirt like a polo, maybe a light sweater. Sometimes button down shirts, sometimes t-shirts.
Are you the proud owner of any futuristic gadgets?
3D Printer Bambu X1-Carbon, and VR Quest 3. I’m mainly my son’s game tester and advisor. There’s also the Muse, a headband that I use for meditation. It tracks brainwaves and gives audio feedback that reflects and helps to deepen your state of calm during meditation. Another is the reMarkable digital ink tablet.
How do you unwind from the top job?
Run on my Peloton treadmill, meditate and write, and use 3D printing. I also play guitar—something I picked up during the pandemic, and I love it. In college, I was a jazz radio DJ (in addition to my public access TV show) and have always loved jazz. Now I’m playing some.
Take us on holiday with you, what’s next on your vacation list?
I enjoy going back to visit family and friends in New York and New Jersey. Also, one side of my family is from St. Croix, US Virgin Islands. I go back to visit family every few years. When I was little, I was sent there for stretches of time during the summer and I’d complain. Now I wish someone would send me there for stretches.
What’s next: Possibly Greece!
How many days of annual leave do you take a year?
One of the many incredible benefits we offer at Pinterest is our unlimited PTO.
Fortune wants to hear from leaders on what their “Good Life” looks like. Get in touch: emma.burleigh@fortune.com for the U.S., or orianna.royle@fortune.com for the U.K. and Europe.
During a National Association for Business Economics (NABE) conference in Philadelphia, Fed Chair Jerome Powell admitted they maybe went too far buying up mortgage-backed securities a few years ago.
The Fed’s controversial purchases of MBS led to the lowest mortgage rates on record, with the 30-year fixed falling to 2.65% in early 2021.
While the move was apparently intended to “ease broader financial conditions” we all know it led to a massive home buying frenzy.
And it came at a time when housing affordability was already at a tipping point.
But instead of easing conditions, it led to home prices roughly 50% higher in many markets nationwide, creating an even bigger housing crisis.
Powell told attendees at the NABE conference yesterday that they maybe shouldn’t have carried out that final round of Quantitative Easing (QE) during the pandemic years.
“With the clarity of hindsight, we could have and perhaps should have stopped asset purchases sooner,” he said.
Adding that “Our real-time decisions were intended to serve as insurance against downside risks.”
Now it would be unfair to go after Powell here because the pandemic was an unprecedented time and extreme measures were taken.
But it does seem painfully obvious that we didn’t need record low mortgage rates during that time.
The 30-year fixed was already quite low in early 2020, averaging around 3.75%. Speaking of hindsight, I’m sure anyone would jump at a rate that low today.
In March 2020, the Fed announced its final round of QE, pledging to increase “its holdings of agency mortgage-backed securities by at least $200 billion.”
The argument at the time was that agency MBS were “central to the flow of credit to households and businesses.”
Sure, we should always have a functioning mortgage market, but did we need the 30-year fixed to go from 3.75% down to nearly 2.50%?
Probably not, and with the benefit of hindsight, we know it created even bigger problems for the housing market.
Aside from it arguably leading to significantly higher home prices (some markets went up another 50% or so), there’s also the matter of mortgage rate lock-in.
The problem with artificially suppressing mortgage rates is that it’s not just temporary.
The most common mortgage type in the United States is far and away the 30-year fixed-rate mortgage.
As the name implies, you get a fixed interest rate for a full 30 years (the entire loan term).
So the Fed’s purchases of MBS during 2020 that pushed rates to all-time lows by 2021 will remain until the year 2050, assuming the borrower keeps the mortgage.
While it perhaps should have been temporary relief for homeowners (and home buyers), the Fed provided relief for the next 30 years.
It’s great for the haves, but awful for the have nots.
We now have a weird dynamic known as the mortgage rate lock-in effect, where the gap between outstanding rates and today’s market rates is huge.
For example, a homeowner with a 2.75% 30-year fixed now faces a rate of say 6.25% or higher if they were to move.
This locks them into their property, thereby exacerbating the housing market’s problems even more.
There’s even fewer available homes for sale because there’s a lot less willingness to sell and face massive payment shock.
Powell also said, “We would certainly not engage in mortgage-backed security purchases as a way of addressing, uh, mortgage rates or housing directly, that’s not what we do.”
While also saying, “We do have, as I mentioned, a very large amount of mortgage-backed securities…”
So he’s basically acknowledging that it’s not in their toolbox moving forward, even though it was in the past.
They will NO LONGER buy MBS as it seems to have exacerbated problems already present in the housing market.
In other words, don’t expect the Fed to help lower mortgage rates again. Look at typical market dynamics instead, like economic data for future rate movement.
If you want lower mortgage rates, root for a slowing economy, not another Fed “bailout.”
Just one caveat though. While Powell admitted it was a tool used in the past, though apparently not to lower mortgage rates, it probably won’t be in the future, at least with him at the helm
Though that’s kind of the rub…would a new look Fed run back QE and let the housing market “cook” again?
(photo: Kevin Dooley)
Fandango is offering a free (or very cheap) movie ticket for Last Days (2025). Must use promo code LASTDAYS at checkout, which gives you up to a $15 discount. Valid at qualifying showings between 10/23/25 – 10/26/25.
You can access your free ticket exclusively at Fandango. It has a 28% score on Rotten Tomatoes.
Based on a true story, Justin Lin’s Last Days follows 26-year-old John Allen Chau’s journey to fulfill his life’s mission. He embarks on a dangerous adventure across the globe to share his faith with the isolated tribe of North Sentinel Island, while a detective from the Andaman Islands races to stop him before he does harm to himself or the tribe.
JPMorgan Chase continues to invest in AI while prioritizing tangible outcomes of efficiency gains. Chief Executive Jamie Dimon said the bank invests $2 billion annually in AI development and is roughly breaking even on savings in a recent interview with Bloomberg. Read more: JPMorgan ranks first for AI among banks with its systematic innovation approach […]
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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.
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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.
In particular, I watch out for these red flags among passive real estate investments.
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 up huge amounts of money, since their properties are now worth 25-30% less on average. Read: capital calls or bailouts from supplemental loans.
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.
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.
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 team on 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.”
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:
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.
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.
Now that you know what not to invest in, what are some indications of a lower- or moderate-risk passive investment?
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.
That sponsor I was just talking about? All their deals are managed by the same in-house property management and construction teams.
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.
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).
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.
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.
