500,000 Followers Under Management

This past week, the Overheard on Wall Street Instagram crossed 500,000 followers.

That’s enough people to fill 25 Madison Square Gardens. And across all platforms, we’re now at 1 million. 50 MSGs. Wild.

What started as a joke during my banking days turned into a side hustle, and somehow became a platform that informs, entertains, and occasionally roasts the markets (and everyone in them).

The goal today is the same as it's always been:

1. To entertain you

2. Keep you in the loop

Whether it’s memes, starter packs, or the 18th reel this week about Trump’s tariffs moving the markets, the goal is to keep you informed, and maybe, just maybe, put a little smirk on your face while you’re stuck in the bullpen.

Since we’ve hit this milestone, I wanted to take a second to share a few quick lessons I’ve learned along the way, and things I hope will be helpful as you navigate your own path.

Do the Best Job at the Job You Have

Let’s be real, most people hate their jobs. It’s rare to meet someone who truly enjoys what they do every single day, especially on Wall Street.

Still, no matter how good or bad the role is, there’s value in doing the best possible job with what you have. Being known as someone who gets the job done (with a good attitude), is one of the most powerful forms of career leverage.

Even on the worst days, when you’re buried in a death staffing with no end in sight, try to stay positive. Show up, do the work, and bring a little more to the table than what was asked. That extra effort compounds, professionally and reputationally.

In finance, it’s not always easy to stay in a good mood. But making the lives of those above you easier usually means they’ll make your life easier in return (at least in due time).

I had an analyst once who responded to every single deliverable with “sounds good, will do.” No questions asked, just straight up execution. I loved working with him, and it’s no surprise that he’s absolutely killing it in his career now.

Having a good attitude doesn’t mean pretending everything’s great. It just means being the kind of person others want to work with. And that alone can take you further than any technical skill ever will.

Invest in Your Health (Mental + Physical)

A healthy man wants a thousand things. A sick man wants only one.

In this industry, it’s easy to sacrifice your health without even noticing. For me, it usually starts with physical health, when I move my body (go to the gym), my mental health and everything else tend to fall into place. The post-gym clarity is real and there is no better feeling in life.

So go workout. Get decent sleep. Eat better than you did last week. Don’t black out every weekend. But even if you do, take the time to recover, and get back on track.

One of the biggest mental health hacks I found was running in NYC. A 30-minute run on the West Side Highway would completely change my mood. If you live in a walkable city, take advantage of it. Nobody ever came back from a walk and said, “I wish I hadn’t done that.”

Don’t Take Your Job (or Yourself) Too Seriously

It’s just a job. If you lose it, there will be another one. If you have none, you’ll figure it out. The earlier you learn this, the less power work will have over your mental health.

Plenty of people in finance lose sleep over formatting errors and missed footnotes. Have pride in your work but don’t build your identity around a job title. Especially one that can disappear in a round of layoffs or a market correction.

If you stick around long enough, your life usually gets exponentially better. So breathe. Zoom out. Don’t ruin your sleep or sanity over something that won’t matter in a month.

Be Patient

When I was a first-year analyst, all I wanted was to work on live deals. I hated being staffed on pitches and always thought, “This is so f**king pointless.”

It wasn’t. I ended up learning more on some of those pitches than I did on actual live deals.

Eventually, I got what I wished for… too much of it. I was staffed on so many live deals that I was rekt. My mental and physical health hit all time lows, and it became one of the darkest periods of my life.

Learning takes time. You’re not going to learn everything in one month. But if you stick around long enough, you will learn and get better at your job. Have goals, yes, but take it one step at a time. 

If you’re staffed on something you hate, get what you can out of it and start steering the ship. You don’t need to blow up your life to make a change. Remember: a one-degree shift in a plane’s course can land it in a totally different city. Same goes for your career.

And if you’re stuck in a miserable job or working for a sociopath: Be patient. Do what you have to do. Keep your head down, and trust that the right next step will show up. It usually does.

Prioritize Skills and Experiences Over Salary Early On

In your 20s, the goal should be skill acquisition. Not salary maximization.

You have the rest of your life to make money. And if you do your 20s right, you can make more in one year in your 30s than in your entire 20s combined.

This applies both on the job and outside of it. Seek out environments where you’ll grow quickly. Take on projects that force you to figure things out.

And invest in yourself - both hard and soft skills. Learn how to build a website. Experiment with AI tools. Take a public speaking, comedy or acting class. Study marketing funnels or Facebook ads. Improve your writing and communication. 

In a world where AI is getting better every day, human skills are becoming more valuable, not less. The more you stack them, the more leverage you’ll have over time. So, start early, and don’t stop stacking.

Start a Side Hustle

I got out of the 9-to-9 grind by starting an Instagram account on the side. What began as a joke became a creative outlet, and eventually, it became the reason I was able to leave my job.

None of it would’ve happened if I hadn’t just started. That’s the real takeaway. Whatever you’ve been thinking about doing: just start. You probably know more about one thing than most people do. So build around it.

Start a blog. Launch a YouTube channel. Create a course. Build a brand. Doesn’t matter what it is, what matters is getting it off the ground.

A good starting point? Find something you 1) know more about than the average person (this can be your job like it was for me), and 2) genuinely enjoy talking or reading about. Then stay consistent. Over time, the compounding will do the rest.

Find Things You’re Passionate About

Your job can be important. But it shouldn’t be your whole personality.

I’ve met too many finance bros whose only hobby is drinking on weekends. And besides being rough on your liver, it makes you pretty f*cking boring.

Find something outside of work that lights you up. Photography, stand-up, running, padel, skating, biking, filming, poker, writing, whatever it is, not just going out with your boys on the weekend.

There’s deep satisfaction in getting better at something just because you love it.

Improve Your Content Diet

There’s more brain rot online than ever before, and the algorithms know exactly how to serve it to you.

These days, I’ll pick up my phone to check something quickly, and boom, I’m 15 reels deep into random clips that add zero value to my life.

You have to be intentional about what you consume. Because it’s programming you, whether you realize it or not.

Follow people and accounts that inspire you. Read things that challenge you or build your skills. Listen to podcasts that teach you something. Your mind is your most valuable asset, don’t feed it garbage.

Be Curious. Talk to Everyone.

“You’re one conversation away from changing your life.”

That conversation could lead to a job. A relationship. A new perspective. But only if you start it.

Cold email someone you admire. Compliment a stranger. Talk to the girl you made eye contact with on the subway. Worst case, nothing happens. Best case, everything changes.

I’ve made friendships, built partnerships, and even started relationships by talking to complete strangers. I’ve never once regretted it.

So get off your phone. Look up. Say something.

Nobody Knows What They’re Doing

One of the biggest realizations I’ve had is that no one actually knows what they’re doing.

Everyone’s figuring it out in real time. The billionaire founder, the Managing Partner with $5billion AUM, or even the finfluencer who “has it all” they’re all winging it, just like you are.

So if you feel lost or unsure of your next step, welcome to the club. Don’t let the illusion of certainty stop you from starting.

Most Things Fail. That’s Fine. Keep Going.

I’ve failed more times than I can count, in interviews, in relationships, in business. But I kept going. Eventually, something clicked.

Failure is just feedback. It teaches you what to change, what to double down on, and where to pivot. If you’re not failing, you’re not trying.

The life you want is on the other side of risk. So try more. Ship more. Talk to more people. Build more stuff.

Most things fail. But the few that don’t can change everything.

*******

The Company Today

Overheard on Wall Street has grown from an Instagram meme account into a full-scale finance media company, with over 500,000 followers on Instagram and a total audience of 1 million+ across platforms (only took about 7.5 years). Below is a quick breakdown of what we’ve built and how you can be part of it.

If you’ve enjoyed the content so far, it would mean a lot if you subscribed to Short Squeez and our other publications.

Short Squeez

Short Squeez is one of the leading daily newsletters for Wall Street professionals. It’s been completely free for nearly five years, and the best way you can support us is simple: open the email each morning and engage with our sponsors (yes, clicking those links actually helps us keep it free).

If our emails suddenly stopped showing up (email deliverability is a much bigger science than you’d expect), check your spam folder and move us to your primary inbox. Still can’t find it? Add [email protected] as a contact, or just shoot me an email and I’ll get it sorted.

My goal is to make Short Squeez the best email in your inbox, every single day. If you ever have feedback or ideas on how to improve, just respond to this email.

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Short Squeez Premium (Insiders)

Short Squeez Insiders is our premium membership, designed for our super fans who want more.

As a member, you get:

• A weekly “Knowledge Drop” with the best articles, podcasts, and research from the past week

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Buysiders

Buysiders is our deep-dive newsletter on all things deals - M&A, buyouts, IPOs, fundraises, and everything in between, written the way a VP would explain it to you at a bar (a sober one, but with a sense of humor). It's designed to give you deal insights you won’t get anywhere else.

Eventually, I want Buysiders to become a source of proprietary deal flow. For now, make sure you’re subscribed, you might even come across deal comps and multiples you won’t find anywhere else (just don’t ask us for our source 😉).

We’ve also revamped the Buysiders Instagram to feature interviews with private equity legends from around the world. Definitely worth the follow.

City Squeez

City Squeez started as a side experiment but it quickly turned into something more.

After spending time in Bali and experiencing villa life firsthand, my perspective on real estate shifted. I used to be in the Buffett camp, only investing in stocks, and ignoring real estate entirely. But Bali changed that. I started asking more questions. Most of my finance friends didn’t have many answers either, unless they were much older.

So I built City Squeez to help us all learn. It covers market updates, investing opportunities, and interesting properties around the world. Think of it as a global perspective on real estate for people who’ve spent too long staring at Bloomberg terminals.

P.S. I’m also working on some real estate projects in Bali. If living in paradise is on your radar, fill out this form and I’ll be in touch.

Content Desk

If you read my last annual letter, you’ll remember I mentioned our agency work (now called “Content Desk”) where we help finance brands grow their social presence and accelerate user acquisition.

Overheard on Wall Street crossed 1 million followers through organic content alone, and we now help other brands do the same.

In just the past few months, we’ve partnered with several industry-leading finance companies, scaling their followings and converting audiences into real customers. I genuinely don’t think there are many people out there who know more about growing a finance brand organically than I do.

If you’re a finance founder or brand looking for help with content and social strategy, fill out this form. We’re close to capacity but may take on 1–2 more partners this year if it’s the right fit.

A Few Last Words

We’ve got a number of other exciting projects in the works that I can’t talk about just yet but you’ll hear about them soon.

For now, I just want to say a big THANK YOU to every single one of you for helping us hit 500,000 on Instagram and 1 million across all platforms.

If you’ve got thoughts, questions, or just want to say congrats 😉, reply to this email or shoot me a note at [email protected].

P.S. We’re also hiring, check out the open roles below:

We’re Hiring

We’re currently looking to fill three roles. Apply below or pass it along to someone you think would be a good fit.

Video Editor
We’re looking for a creative video editor to help us make high-quality reels and the occasional long-form video. Adobe Premiere Pro skills are a big plus, but not required. If you’ve got an eye for storytelling and a top-bucket video-editing skills, apply below with your portfolio and 2–3 examples of your most relevant work.

Markets Analyst
If you’re obsessed with the markets and always in the loop on what’s happening across business and finance, this role is for you. We’re looking for someone who’s creative, independent, and ideally has a background in finance (IB, PE, or any markets role). It’s a part-time position, designed to complement your full-time job.

Head of Drip
We’re looking to level up our merch store and need someone who understands both great design and great product. Bonus points if you have experience with e-commerce, SEO, and building brands through merchandise.

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Cheers,
Overheard on Wall Street