Hey neighbors, happy Thursday.

If you've followed this newsletter long enough you know that I travel around a bit. I've been in NC for the past two weeks.

Last weekend the Tar Heel state got the most snow they’ve seen in decades. 12+ inches in some places. It was enjoyable watching all of my fellow North Carolinians freak out. Lines were out the door for generators, booze, gallons of milk, and bread.

Meanwhile, the markets are having their own meltdown lately. Bitcoin dropped below $70K today for the first time in 15 months—down 44% from its October peak. Nasdaq's on its worst 3-day slide since April last year.

Anywho, on to this week's content 👇

🏠️ NYC housing: Zillow dropped their annual Top 10 Hottest Housing Markets ranking NYC the 3rd hottest housing market in 2026 (with Hudson Yards maintaining its status as the most expensive neighborhood.

👷 Jobs data: The government shutdown is delaying tomorrow's official jobs report, so traders are paying more attention to private data this week. The Challenger report dropped this morning: 108,435 job cuts in January—the highest for the month since 2009. Publicly announced hiring plans hit their lowest January on record. UPS (30K cuts after dropping Amazon) and Amazon (16K) led the way.

🥩 V-Day: Yep, it’s around the corner. Delmonico's (NYC's oldest steakhouse) is doing a four-course V-Day dinner with hamachi crudo, extravagant cuts, and a pink version of their baked alaska (which was invented there). $195/person. RSVP. Friday night (V-day eve) still has dinner openings. You’re too late for dinner on the 14th.

🎤 Cool job: Brooklyn Comedy Collective is looking for a Director of Business & Marketing. $70-75K to run ops and growth. The NYT called them "the right mix of scrappy and chaotic." If you've ever wanted to expense improv shows, here's your shot. Apply by Feb 16 (click the banner on their homepage).

Fun fact: This is the first time I’ve switched all of these to red…

Nasdaq | $22,670 | -2.43% 🔴

S&P 500 | $6,823 | -0.51% 🔴

Bitcoin | $67,831 | -22.40% 🔴

Cash Confessionals are anonymous, weekly stories where NYC locals peel back the curtain and expose their money habits. Wanna submit yours? Go here.

Career: I work as a creative strategist, but I also have a background in data analytics and software engineering. I've had roles that combine all three. I like it because creativity is important to me. I don't really hate the work. I think it's more about the company and the people.

Net worth: Probably $50K after accounting for other assets. Theoretically more since some of my loans are Parent PLUS, but I count them as my own liabilities.

Salary: $125K base, $10K bonus, and probably $1K or so from music gigs and shows I produce during the year, which is rewarding.

Salary journey: I started at $51K right out of college. Got a raise to $57K after a year, which felt slow, but progress is progress.

The pivotal moment was in 2021 when I got an offer from another company and used it to negotiate a raise to $75K base and $20K bonus. That's the moment I left "survival mode."

I took a brief pause to do a software engineering bootcamp, which was turning point #2 since I brought data into my skill set. Went to $130K, was there for a year and a half, but took a $5K cut to leave a toxic environment.

Living situation: I rent in Bushwick with one roommate. $1,700 a month.

Financial goals: My long term goals are to build sources of revenue for myself so I can be less dependent on a job. Ideally, I want to build something that generates $2-3K a month starting off, then branch out. I feel fortunate that I can code, so I'm currently launching an app.

Rn, I feel good about where I'm at with my salary, and for the past two years I've maxed out my retirement accounts. I hit $100K in savings across all accounts for the first time last year, which was a great feeling.

On my mind: Paying off student loans and buying a home. The part that stresses me out regularly is staying within the budget I set for myself during the week, but for the most part I'm pretty frugal.

Rich in NYC: Being able to live alone and go out for drinks and dinner a few times a week without stressing, all while contributing to retirement and saving 20%+ a month. Also being able to travel internationally twice a year for two weeks, with domestic trips planned as well.

The minimum to live "comfortably" in the city is probably $65K; could be done with less depending. Assume rent will be $1,300, groceries $250 a month, utilities around $100. Combined with some level of savings, the floor is $50K, but $65K is when you can start treating yourself to small pleasures.

Career advice: Don't be afraid to move around within reason. I've had to jump a bit to increase title and salary, but mainly to do the type of work I wanted to do at the moment. Also, continuing to build new skill sets is really crucial.

Other income: I get paid monthly for a show I produce, about $50 a set, and I also produce other shows during the year which comes out to about $1K total. I also make money from music streaming on platforms like Spotify, but it’s super variable. I've had years where I freelanced as a strategist and made $20K outside of my main job.

Side hustle: I'm working on an app with plans to generate $2K monthly from a base of 10K users.

Spending: I grocery shop and make lunch for myself four days of the week. Weekends I tend to eat out more. I spend around $300 a week including groceries and discretionary spending, but I'm trying to get better at understanding where that's going. I think a lot of it is weekend activities with my girlfriend.

Biggest expense: Probably eating out.

Can't live without: Protein powder.

Best money decision: Doing the software engineering program. That will continue to pay dividends for years. I think it's a different proposition now and I'd probably suggest people teach themselves to code, but that's a different conversation.

Worst money decisions:

Debt: I pay my credit card off each month. I have $60K-ish in student loans. I feel fortunate since I know people who have a lot more. I think my amount is pretty normal, even if it feels uncomfortable at times.

Favorite credit card: Chase Sapphire Reserve. I use the rewards every summer to travel and have done that for three years. I also got an Amex and a Chase Discover card. The third was unnecessary and dropped my credit score. For some reason I thought it would boost it since it would add to my available credit. The learning there was to just increase the credit line on one card instead of taking out a new one.

Emergency fund: I keep 3-6 months of expenses at one time. I knew I needed to build this up more when I left my last job. Fortunately, it was a mutual separation and I waived my right to pursue legal action against a toxic manager, which made me liquid to the tune of 6 months. I got a job 6 weeks after that.

Saving for: Not really. Long term, a down payment on an apartment, but other than that I invest and keep cash liquid.

Investment strategy:

Financial freedom: Being able to just take my laptop and work on my businesses doing coding and strategy from anywhere in the world, maybe Paris or Lisbon, and feeling independent.

Retirement: I plan to retire earlier than most. Hopefully, by my early 40s. I'd need around $3M in cash to comfortably not work, but the calculus really boils down to cash flow. In retirement, I'd focus on community work like coaching, maybe becoming a therapist or counselor. Teaching kids to code or make music. I'm also certified as a yoga and meditation teacher, so that could play a part. Giving back feels important to me.

Long-term goals: I want to build something that gives me flexibility and fits my professional ambitions while feeding my purpose. I aim to make 9-5 optional in the coming chapters of my life. I want to be more dependent on myself, and also have the ability to leave the city but come back since I would have purchased a property at that point. I want to see money less as a master and more as a sidekick.

📧 Submit your own Cash Confessional for an upcoming newsletter. Go here.

Thanks for reading this week’s edition. If you have ideas for stories, know about new business coming soon, or want to do your own anonymous Cash Confessionals submission, let me know!

Josh Stilwell

P.S.

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