Overheard on Wall Street Annual Letter

Good Morning, Overheard on Wall Street and Short Squeez Fam!

As 2024 comes to a close and we step into 2025, I wanted to take a moment to reflect on the journey of Overheard on Wall Street—both the business and the person behind it. This year, I decided to write an annual letter to share our milestones, progress, and goals with you.

While I’m not usually one for the spotlight, I’ve come to appreciate the value of “building in public,” inspired by successful start-ups like Beehiiv. Plus, let’s be real, can you even call yourself a finance company if you don’t write an annual shareholder letter? I hope to make this a tradition going forward.

How It All Started

I started Overheard on Wall Street (OWS) in January 2018, which, believe it or not, was seven years ago. At the time, I was an investment banker and my life was fully consumed by work. To bring some levity to my days, I created an Instagram account to share the absurd and hilarious things I overheard in the bullpen, like a VP saying to an MD: “You’re so 1% bro.”

The account grew organically and fast. Part of the reason was that it was the only account of its nature on Instagram (the closest was Goldman Sachs Elevator on Twitter, but it had moved away from its original quotes after its founder, John LeFevre, became more of a public figure). For me, OWS became a great way to destress. I’d post from the bullpen, and later fellow analysts would send me my own memes. It was the highest of highs!

When I transitioned to private equity during the zero-interest-rate era, I got (to put it lightly) rekt. The silver lining was that I worked on a lot of deals, but I got burned out. Despite that, I still managed to post regularly on Overheard on Wall Street and grew it to 200,000 followers by 2021.

Stuck in my cubicle and NYC apartment during the pandemic, I became desperate to travel and escape the grind of Wall Street. I spent Christmas in Tulum, where I met an entrepreneur who encouraged me to take a leap of faith and go all-in on OWS.

Upon returning to New York, I took a leap of faith: quit my finance job, moved to Tulum, and launched a daily newsletter. Along the way, I brought on a talented partner, someone I’m proud to call a close friend, who was working at Meta at the time.

The Vision

The goal was simple but ambitious: to transform @overheardonwallstreet into a high-finance media company that catered to professionals in investment banking, private equity, hedge funds, and related industries—an audience that lacked targeted and relatable coverage.

I also noticed a major shift in the way people consumed finance news. Legacy outlets like the Wall Street Journal, Bloomberg, and Financial Times dominated the space, but the content wasn’t designed for a social media-savvy audience. People were increasingly turning to accounts like mine for finance news that was:

1. Short (no one had time to read long articles every day).

2. Funny (it made a high stress industry a little more bearable).

At one point, my Instagram stories were getting over 100,000 views and it was clear there was demand for this kind of content.

Where We Are Today

Fast forward to today: OWS has grown into one of the world’s leading finance media companies. What started as a single Instagram account has grown into a multi-platform business with nearly one million followers across all channels. This wouldn’t have been possible without a team of ten incredibly talented individuals who work tirelessly to bring this vision to life.

We’ve stayed true to our mission of delivering high-quality news and entertainment while making Wall Street more accessible, engaging, and relatable.

My goals remain simple:

1. To entertain YOU.

2. To educate YOU and keep YOU informed.

Highlights of 2024

It’s been an incredible year for OWS. Here’s what we achieved:

Socials

• Over 250 million impressions on the Overheard on Wall Street Instagram.

• Added 250,000+ followers across accounts (including 150,000 on OWS).

• Grew Finance Golden Era to over 100,000 followers.

• Added 10,000 followers on X (formerly Twitter).

Newsletter

• Reached ~50 million impressions on the Short Squeez newsletter.

• Added 75,000+ new subscribers, bringing our total to 220,000.

• Wrote 450,000+ words.

• Increased open rates to 54% (up from 45% last year).

Team

• Expanded the team to 10 people.

• Hired Justin Best, an investment banker and Olympic gold medalist.

• Published a Working Conditions Report and an open letter to Wall Street firms that led to major changes at banks like JPMorgan.

• Launched a marketing agency for finance brands.

• Visited five new countries and found a new home in Bali.

Overheard on Wall Street

2024 was the best year yet for Overheard on Wall Street on Instagram. We added 150,000 followers, by far the highest growth of any account in the finance niche.

This success boiled down to one key factor: producing high-quality, consistent content (posting 4-8 times daily). Over the past couple of years, I’ve brought on talented individuals from various areas of finance (investment banking, private equity, private credit, etc.) to create original content for Overheard on Wall Street. Most of these folks work part-time, so the content you see often comes directly from the fire (aka bullpen).

At the start of the year, I implemented new processes for creating content across all our accounts:

• @overheardonwallstreet (finance commentary, quotes, memes, starter packs)

• @short.squeez (finance news and insights)

• @freakindsheets (Excel memes and tips)

• @financegoldenera (historical Wall Street content)

I firmly believe in creating systems rather than micromanaging. Once you’ve laid out a blueprint, you let smart people do their thing. Giving my team creative freedom has been one of the best decisions I’ve made, and it’s helped us level up our content significantly this year.

We also experimented with new formats on OWS Instagram, such as:

• Starter packs.

• Meme drops.

• Reels.

• Our original “On The Street” series.

Initially, I thought reels were the only way to grow on Instagram, but some of our feed posts blew up as well. Here are a few of our top-performing feed posts from 2024:

• Wall Street to Goose Farmer

• Dating a Finance Bro Expectations & Reality

• Why Does My Head Always Hurt

• Monday Plans

• Two Types of VPs

Ultimately, the only real growth “hack” on Instagram is consistent posting.

Our most-viewed reel came from the On the Street series with 4.1 million views. The concept behind the series was to bridge the knowledge gap between Wall Street and Main Street. While Wall Street can seem out of touch with everyday life, Main Street often doesn’t understand the intricacies of finance. The series aimed to bring these worlds closer together.

The show performed exceptionally well, but it was a logistical challenge. I have huge respect for people that have made a living out of interviewing people on the street. For every successful interview, at least ten people turned us down. I also wanted to maintain high production quality, which meant lugging around all my filming gear for each episode. Ultimately, I decided to put the series on hold as we had a lot of other projects in motion. But we still managed to produce a handful of reels and even dropped a couple of YouTube episodes.

That said, if you’re a good interviewer, based in NYC, and interested in doing street interviews for us, please reach out! I’d also love to hear from anyone who wants to help create content for Overheard on Wall Street.

Wall Street Work-Life Balance: A Call for Change

2024 brought attention to one of Wall Street’s most pressing issues: work-life balance. After the unfortunate deaths of two Bank of America employees, possibly due to being overworked, I decided to take action. I conducted my own research, wrote a Working Conditions Report, and published a 10-page Open Letter to Wall Street, outlining a 14-step framework for change.

The report gained significant media coverage and was picked up by Bloomberg and the New York Post. I also collaborated with the Wall Street Journal to publish an article titled: “How Bank of America Ignores Its Own Rules Meant to Prevent Dangerous Workloads.”

A handful of months later, two major Wall Street banks made these changes:

• Bank of America rolled out a new timekeeping tool that requires bankers to log hours daily instead of weekly, along with capacity outlooks for more work.

• JPMorgan capped junior bankers’ workweeks at 80 hours and created a new executive role to oversee analyst well-being.

This work was a proud moment for me and the team. Being able to push for meaningful change in an industry as rigid as finance is no small feat. While we’ve made progress, there’s still a long way to go. Improving Wall Street’s culture remains one of my top priorities, and you can count on us to keep speaking up.

Short Squeez Newsletter

Short Squeez summarizes news from around the world of Wall Street in a quick and witty 5-minute read. 

• A Story of the Day - the most important finance news of the day.

• Curated market news from the best sources out there.

• A Book of the Day and Daily Acumen section to provide timeless, knowledge-enhancing content.

• Dank memes.

I want Short Squeez to feel like your smart friend sharing the latest news with you over a cold one and not like a big, impersonal media organization. While we maintain a professional tone, we sprinkle in tongue-in-cheek humor and dank memes to keep the newsletter engaging and entertaining.

In the early years of Short Squeez, we aimed to be more of an all-encompassing business newsletter, similar to Morning Brew. But over time, we’ve honed our focus and doubled down on our niche: Wall Street professionals. That’s the industry I know best, and it’s the audience I’m passionate about creating content for.

If you are not subscribed to the best newsletter on Wall Street, now would be a great time to do so!

Engagement & Growth

Short Squeez reached a 54% open rate this year, among the highest in the industry (most newsletters average around 20%). This was up from 45% last year. 

The key? We spent 2024 focusing on subscriber quality, removing inactive readers, and acquiring engaged ones. This not only increased open rates but also doubled click-through rates.

By the end of the year, we hit 220,000 high-quality, highly engaged subscribers. Unlike social platforms where algorithms help you grow, newsletters require you to drive growth yourself. Paid acquisition, mainly through social ads, was also a major driver of subscribers in 2024.

For 2025, I’d love to hit 500,000 subscribers, though even landing at 300,000 would be a huge win. 

Monetization

One of the biggest advantages of the Overheard on Wall Street brand is its seamless monetization potential. We haven’t missed a single newsletter ad slot in 3.5 years, which is saying something because in 2022-2023 the ad market was pretty dead, and only the largest newsletters were able to maintain consistent sponsors.

A major focus this year was building long-term partnerships with a handful of brands that align with our niche. From the advertisers’ perspective, they get consistent results from one of the largest finance media brands. From our perspective, we get consistent revenue and can focus our efforts on creating the highest quality content for them.

A big thank you and shoutout so some our most prominent partners in 2024:

• Hebbia

• Percent

• Kalshi

• Corporate Finance Institute

• Macabacus

• Leland

• Mosaic

• JKBX

We also partnered with Nest Seekers, an international real estate firm, to feature opportunities for renting, buying, and investing in our newsletter every Friday. Real estate is an area many of our readers are deeply interested in. The response has been fantastic, and I’d love to expand on this in 2025. Shoutout to Paul Cibrano for the partnership. He also writes a great newsletter that you should definitely subscribe to.

And also a special thanks to Zac Atkins, our Brand Partnerships Lead, who has been instrumental in securing these deals. If you’re interested in advertising in the Short Squeez newsletter, or any of other platforms, fill out this form, and we’ll be in touch. 

Additionally, if you have suggestions for the types of partners you’d like to see us collaborate with in the future, fill out this quick 30-second survey here.

Agency: Helping Finance Brands Grow

After working with nearly every major company in the finance and investing niche, one thing became clear: many of these brands have great products but struggle to market them effectively.

This realization led me to launch an agency this year, focused on consulting brands in the finance space on growth, strategy, and marketing. With a deep understanding of both finance and audience building, having grown an audience of nearly 1 million followers and subscribers with virtually no ad spend, I knew I could add a lot value.

One standout project this year was working with Kalshi during the election cycle. Shoutout to Brandon Beckhardt for the partnership. Kalshi is a prediction market platform that assigns probabilities to real-world events and news. The partnership felt natural because Short Squeez was already covering finance news. For example, if we reported on a potential Fed rate cut, Kalshi’s platform could offer market-driven probabilities for various rate cut scenarios.

In just a few months, we helped grow Kalshi’s Instagram from 15,000 to over 90,000 followers, significantly increased engagement across their socials, and added thousands of users to their platform. On election day, Kalshi became the number one global app, even overtaking ChatGPT! The success of this partnership showcased the power of aligning strong content with a strong product.

In 2025, my goal is to partner with three companies in the finance and investing space, helping them dominate their niche and establish themselves as industry leaders. My services will include social media management, strategic consulting on growth and paid growth strategies, though my offerings will go far beyond these core areas to ensure tailored, impactful results.

If you’re interested in working together, fill out this form, and we’ll connect.

Insiders Membership: Revamped and Better Than Ever

Insiders is our paid newsletter membership. We spent a lot of time revamping this membership in 2024. I thought about why someone would pay for a content membership. I realized I should make something that I was interested in myself. Not just finance or investing content, but something that helps finance professionals level up in career, health, investing, and knowledge.

Here’s what we implemented this year:

1. Elite Sheet (Investing Newsletter): A monthly summary of key happenings in public and private markets.

2. Knowledge Drop Newsletter: A roundup of the best:

   • Research.

   • Long-form articles.

   • Podcasts.

   • Most-clicked links from the prior month.

3. Wellness Newsletter: Covering trends like:

   • Cold plunges.

   • The science behind standing desks.

   • Meditation techniques.

4. Resource Suite: An exclusive collection of tools, including:

   • Investor portfolios (e.g., Buffett, Ackman).

   • Our full book list.

   • Recruiting resources and institutional research.

Our Insiders members are some of our most engaged readers, what I call our superfans. While we published some top-tier content this year, I realized we didn’t promote the premium membership enough. 

Many people told me they didn’t even know we had a premium membership. For 2025, my goal is to improve awareness and grow Insiders to 1,000 subscribers. 

Here is some of our top-rated content in 2024:

• Top 5 Wall Street Interview Tips

• How Much Sleep Do You Really Need?

• Do Standing Desks Work?

• Top 10 Things I Learned in Investment Banking

• How Much Do You Need to Exercise?

Buysiders: Deals and Deal Flow

Buysiders, our deals-focused newsletter, covers the most interesting M&A, private equity, and VC transactions. Each edition includes deep dives into the three most prominent deals from the past month, focusing on strategic rationale, valuation and our takeaway.

The thesis for Buysiders was simple: I wanted to build a list of accredited investors to share unique investment opportunities with. While I didn’t necessarily need a separate newsletter, I saw a gap in the market. Sure, you can find deal coverage in publications like Axios Pro Rata or StrictlyVC, but few newsletters truly break down deals in detail.

2024 was a great year for Buysiders:

• Grew from 4,000 to 12,000+ subscribers.

• Maintained an open rate of nearly 70% (this is unheard of!)

• Built an audience largely composed of accredited investors.

For 2025, I aim to grow this list to 25,000 subscribers and share more exclusive investment opportunities. If you’re raising capital for a fund or startup, shoot us a note, we’d love to help.

Recruiting and Freak in the Sheets

As a finance media company with hundreds of thousands of followers, launching a recruiting arm felt like a natural next step. In 2023, I worked with our CFO (“Chief Freak Officer”) Henry Copses to create excel, modeling and recruiting courses, which did really well for us. Building on that momentum, we spent 2024 working on a dedicated recruiting website: OWS Recruiting.

But scaling the recruiting arm proved challenging. As a business owner, you have to prioritize, and while I’m passionate about helping people break into high finance, I decided to focus on areas like Short Squeez, which were growing rapidly and demanded more attention.

That said, I’d love to revisit this venture in the future. The vision is to build something similar to Mergers & Inquisitions, a one-stop shop for breaking into high-finance roles.

If you’d like to help build this out with us, reach out!

Freak in the Sheets: As part of our recruiting efforts, we also launched an Excel-focused Instagram account, @freakindsheets. Initially, it featured educational content like Excel shortcuts, but we eventually pivoted to memes. Henry has done an incredible job with this, adding over 10,000 followers in 2024.

Team Growth

As a content-driven business, I’m always looking for ways to level up the quality of what we produce. This year, I came across an account called Finance Golden Era, which had grown to 50,000 followers in just a few months. I reached out to the creator, and within weeks, Valter had joined our team.

Valter didn’t just need exit liquidity—he wanted to join one of the most influential teams on Wall Street. Finance Golden Era posts have been some of our top-performing content this year, and we ended 2024 with 105,000 followers on the account. 

The goal with Finance Golden Era is to diversify OWS’s content. While OWS and Short Squeez focus on finance commentary, humor and news, Finance Golden Era highlights important historical moments and figures in Wall Street’s history. FGE’s content has resonated deeply with our audience.

Here is some of our best content on Finance Golden Era in 2024:

• Pinstripe Suits

• Warren Buffett and Bill Gates

• Wolf of Wall Street Premiere

• 1980s Swiss Finance

• Trump in the 80s

If you have a social account or newsletter in the finance niche and are looking for a partner or liquidity, reach out. I'd love to discuss how we can work together.

Hiring an Olympic Gold Medalist

Today the OWS team has grown to ten people. Last year I made one of my favorite hires in Justin Best - Gold medalist at the Paris Olympics. 

Justin made the news because he is no ordinary gold medalist. One of his side hustles? He is also an investment banking analyst!

I had posted about Justin winning the gold medal at the Olympics. The post went viral and Justin got thousands of LinkedIn requests from all over the world. 

Justin and I started DM-ing and I found out one of his many talents was also creating memes. His Instagram bio literally said “I make memes about my hyper niche sport.” 

A combination of investment banking, sports and finance made Justin the perfect fit to be the Chief Meme Officer at OWS. So it took a couple of calls and Justin joined our team. Justin has been instrumental in leveling up our video content this year and we have a great surprise in store for you in 2025 (stay tuned!). While we’ve joked about starting a podcast together, for now, I’ll let Justin focus on his banking career.

Travel: Finding Balance While Exploring the World

Since leaving my private equity job, I’ve made it a priority to explore the world and work from different cities. Over the past few years, I’ve lived in Barcelona, Paris, Rome, Istanbul, Lisbon, Dubai, Tulum, and Bali. I have not gone local in America because, to be honest, there is no city that even comes close to New York. I’ve tried living in places like Miami and Chicago, but they are not for me. 

These days, I spend most of the year in NYC and a few months in cities I’ve grown to love. Of all the places I’ve lived, Bali stands out as my favorite. It offers an incredible mix of scenic views, warm hospitality, amazing food, and a thriving community of founders and entrepreneurs. Bali is also the wellness capital of the world, where saunas and cold plunges are as common as Starbucks in Manhattan.

In the coming years, I plan to spend even more time in Bali. I’ve started working on some villa development projects there, and if you’re interested in owning or investing in a villa in paradise, fill out this form (who knows maybe you’ll end up being my neighbor ;) )

Entrepreneurship and the Temptation to Return to Finance

This summer, while in New York, I received one of my first carry checks from my private equity days. It was unexpected, but it was a solid chunk of money that made me seriously consider returning to finance.

The equation for getting rich in finance is straightforward:

• Dedicate 15-20 years of your life to the industry.

• Climb the ranks and make a few million dollars by your late thirties or forties.

It’s a proven formula, and for many, it’s a great fit. I’m incredibly grateful for the time I spent in finance, it gave me a strong work ethic, sharpened both my hard and soft skills, and connected me with incredible mentors who continue to inspire me. But as much as I value that chapter of my life, I realized it wasn’t the right long-term fit for me. That’s what led me to pursue entrepreneurship, and honestly, I’ve loved (almost) every second of it.

Entrepreneurship isn’t easy, you have to earn every dollar yourself, but it’s incredibly fulfilling. This summer, I consulted some of my mentors (partners and managing directors in finance) about the possibility of returning. Their advice? Double down on what you’re building. They admired the business I’d created and said they’d do the same if they were in my position.

Ultimately, I decided to stay the course. I truly believe this is what I’m meant to do. I’ve realized how much I love being glued to my phone or laptop, knowing that I’m making a difference in millions of people’s lives daily, or at the very least, giving them a reason to laugh. For now, I want to spend these years traveling, growing my business, and enjoying the freedom I’ve worked so hard to create.

Goals for the Future

My goals for the future may sound simple, but they’re what keep me focused:

1. Stay the course. One of the biggest challenges in business is avoiding distractions. I remain committed to being the top source of entertainment and information for Wall Street professionals.

2. Grow the audience. I aim to reach 5 million followers and subscribers across all platforms in the next few years.

3. Build/invest in related businesses. Whether it’s starting a new business or launching an investment fund, I want to use my network and expertise to help companies grow in the finance niche.

I can’t share too many details just yet, but you’ll soon hear an exciting announcement about my partnership with a VC firm to acquire a company in the finance niche and take it to the next level. I’ll also be keeping an eye out for more strategic opportunities and acquisitions like this in the future.

Ultimately, I want Overheard on Wall Street to be a flywheel, a platform where smart people create content and promote businesses we own or invest in.

Conclusion

If you’ve made it this far, congratulations, you’re a real one. I hope this letter gave you a behind-the-scenes glimpse into our journey and maybe even sparked some inspiration, whether it’s to travel more, consider a fresh start or launch that side hustle you’ve been dreaming about.

I’m always eager to connect with ambitious and creative individuals, so if something here resonated with you, don’t hesitate to reach out (just reply to this email!). I’m constantly on the lookout for talented people to join the team or collaborate with, so if you have ideas on how we can grow or take things to the next level, I’d love to hear from you.

Cheers,
Overheard on Wall Street