2025 Year-End Letter

There’s no Sponsor for today’s newsletter - other than plugging my company Buyside Hub. Buyside Hub is a compensation analytics and job board platform I founded earlier this year. With your help, we’ve been able to rapidly grow the community, shedding light on compensation levels and culture across hundreds of Buyside & Sellside firms. If there’s one thing you should take away from today’s newsletter it’s that I’d love to have you on Buyside Hub ASAP! It takes a few minutes and I’ve poured my blood and sweat into the business - lend me a hand and join today.

Harry’s 2025 Year-End Letter:

2025 flew by, but holy fuck, we are executing. A lot of you know I’m very competitive, I still play soccer competitively. I have a very in your face approach, playing a high-press so I can get tap-in goals, standing in the goalie’s way on corners, shoving people off me when I’m on the ball, running around box-to-box, regularly nutmegging people (this is the most humiliating thing you can do to an opponent), passing the ball to where i want people to be, rather than where they are, and doing a lot of grunt work to give teammates as many silver platter opportunities as possible. That’s my approach to business, in a way.

The HYH “business” has transformed into something quite nice. Blood, sweat, taking punches and getting right back up, endurance, and showing up every day.

What I always rave about on the HYH side is 1) With social media and distribution, you can reverse engineer your way into businesses (Newsletters and Buyside Hub so far) 2) the margin profile is very high and all strategic investment I make can be flexed back immediately 3) I’m locked in and avoid noise and distractions.

We laugh at the memes and jokes all the time, but the below is no joke. I hope you allow me some time to step away from the funny memes, blow off some steam, be a little vulnerable, and prove to you how intense I am about getting things right for the community. Let’s get into it.

High-level thoughts: We’ve gone from nothing to something in 30 months.

That’s pretty much been the revenue trajectory. Since I turned on the engine in mid 2023, the growth rate has been robust.

A lot of my luck has come from hard work, aggressively scaling up newsletter properties while one still can, great teamwork, and robust tailwinds in the AI and prediction markets industries. There’s a constant theme in my businesses where I continually focus on each vertical having two different revenue streams. Generally, advertising and subscription revenue.

Don’t be afraid to spend money to make money: 2H24 and 2025 were periods of large capex, but the capital allocation process has been relatively measured in nature and has come with clear moments on when and how to turn on the FCF spigot.

Advertising is going gangbusters, but I want way more subscription revenue: The advertising business has been incredible, but I want to get defensive while times are good. I keep working towards wanting to diversify further and further away from advertising revenue and more into predictable and re-occurring subscription revenue.

Vanity Metrics aren’t everything - push towards taking action: While I’ll lay out some readership and follower counts that are quite high, the back half of this year has zoned in on “Okay, what % of ppl are actually taking action, and what accounts are quite docile in nature?” I am zoned in on propensity to spend and propensity to take action and making sure I’m making things that provide value and drive those actions. The reality is no one can create content on a sustainable level unless the people digesting the content are taking action. That can mean engaging in an occasional ad, maybe booking a demo with an advertiser, buying something in a one-off manner, contributing to Buyside Hub, etc. That’s what keeps the lights on and a lot of my approach in 2H25 has turned towards not worrying about if people unsubscribe or unfollow and making sure the people with the propensity to do things do them, receive value, and know that I appreciate them greatly (I appreciate you greatly).

I’ve gotten increasingly more intense because I don’t feel like HYH has hit a safe number or safe level of scale yet. You’ll see in this piece how I’ve been tying playing soccer and my general commitment to showing up every day into how I’ve approached business. In many ways, it’s like that Timothee Chalamet speech where he says he unabashedly admits he is in the pursuit of greatness, understanding “people don’t usually talk like that”. A lot of what I’ve included in here is quite bold and might raise your eyebrows, but I spare niceties; I want to provide value.

2025 was defined for me as a “Standing things up” year; 2026 will be the “Value” year. 2026 is going to be about taking a look at everything core in my portfolio and making sure we’re providing valuable info to everyone. Let’s get into more details around the business units below.

Business Units:

High Yield Harry’s Newsletter:

The newsletter you’re reading today!

This newsletter is packed full of credit and investing oriented content, what I’m up to business-wise, interviews with finance professionals, and increasingly more distressed credit oriented research.

This is the first year where we made a credit research hire and hired a remarkable research analyst named Jake. Jake’s understanding of in-depth restructuring analysis has been remarkable. If you are in distressed credit, private credit, restructuring, or leveraged finance, then please reach out to Jake here. Jake would be an Analyst hire that would materially outperform your expectations.

For me, having a dedicated research team is crucial to the future of this newsletter, so Jake is only the beginning. We are going to regularly be adding to the team in 2026, so I recommend any self-starter who is passionate about restructuring or PE investing reach out.

We are lucky to have Octus and Cognitive Credit as incredible partners as well.

HYH Premium remains a solid credit resource platform: Given a lot of the credit recruiting and job search content may be a one-time purchase in nature, we’re moving into providing more recurring restructuring, PE, and business study content on the paid side of the newsletter. If you want to access our 1) Credit recruiting resources 2) City Guides and 3) Restructuring & Business Deep Dives, then upgrade below.

The Wall Street Rollup:

The Wall Street Rollup is 20 months old, starting from a small acquisition to a consolidation of a handful of other finance newsletters that have over 82k readers and a 55% open rate. This is built by myself and a very smart and mission-driven team.

We’re dialed in over the weekend, helping you get ready for the week every Sunday at 8pm. We want to tell you what you need to know around earnings, headlines, and M&A news without any clickbait shit.

We’re increasingly focused on serving primarily M&A oriented professionals, as well as public equity markets professionals. This allows us to zone in on the niche and focus more on quality over quantity. In an increasingly competitive market for newsletter ad spend, I believe chasing vanity metrics are not worth it. Newsletters have cable company level churn, but without the corresponding cable revenue.

We also launched a paid platform called WSR Investing Club where we focus on topical stocks, with a value-oriented focus. This ties into the theme I called out where the goal is to diversify into two different streams. I also think this is going to become a great community and I’m committed to providing value to our community members.

I expect WSR IC to continue growing rapidly in 2026 (we’re looking for both more writers and more paid subscribers) and we’ve already sold out a ton of 2026 ad inventory, making a shift to a 3x/week newsletter potentially possible for later in the year.

If you want to advertise with us, please reach out to [email protected] 

Buyside Hub:

For at least my 30s, Buyside Hub is my life mission. It stems from my experience in Finance. My troubles finding a job. My inability to assess company culture. My disdain for non-technical recruiters who don’t care about me and want a frothy check. I’ve long held the belief that the bulk of recruiters are not a value-add and are middlemen who will eventually be hit by tech-enabled features and automation. I’d like to be a part of that story.

I wish I could do right by every candidate and every person looking for a job. I want as much transparency and democratization as possible. Every hard worker deserves a fighting chance.

When someone gets a job from Buyside Hub, it makes my day and is the least I can do to help as you continue your journeys in finance. That’s why the Job Board is free to everyone.

This year, I’ve also done a ton of things that don’t scale and have been very manual in my efforts of getting people on the platform.

While length of access varies, Buyside Hub is largely free for contributing users. It’s a community – follow our contribution process and you join the community and the more people in the community, the more we all win. The bulk of the revenue is and will always be passed onto the enterprise side and the solutions we provide there.  

And my pain tolerance is quite high - in 2025 I didn’t necessarily need Buyside Hub to have crazy revenue, our cost structure is materially more flexible in nature. I have a philosophy of the consumer coming first and the platform is set up for consumers who contribute to benefit materially.

I feel confident that we have the strongest and best database of recent wall street compensation levels. I also feel confident that our technology-enabled capabilities are going to slowly eat away a lot of search processes.

If you would like to cut your recruiting expenses materially, please email [email protected] 

My only ask today is this: if you’re still not on the platform, I’d love to have you join Buyside Hub today.

Instagram and X

• High Yield Harry: 149k followers on IG, 155k on X

• Wall Street Rollup: 154k followers, 20k on X

• Guy in Finance: 76k followers

On the Instagram side, growth has plateaued there and I’m unfortunately a little disillusioned on that platform as posts that regularly pop off on X are now duds on Instagram. The community is a lot smaller and has disengaged more, as I think the average user gets tired of Instagram, especially as Zuck has continued to increase ad load and move content away from seeing your friends’ posts.

What’s been increasingly unimpressive about Instagram from a FinMeme lens is how much reel slop and LARP content has taken hold on the platform. IMO, Instagram is increasingly becoming a place just to repost my X content on and to have ppl move to newsletters and Buyside Hub.

Aside from HYH, The Guy In Finance page has grown impressively this year by leveraging some of what I raised above - this account is meant to be run by an Analyst/Associate and is a great medium for anyone in that cohort who is looking to join the finmeme space (hiring details later on in the piece).

On the X side, things have been flying on all cylinders. This was the year when I became more known on X than on IG. I’m actually quite impressed by the changes Nikita Bier has brought to the platform. There’s a lot of momentum and fun on that platform. Increasingly, I’ve been more than just a FinMeme page on X and have been getting a lot of eyeballs from the Tech community. There’s been a lot to meme about in Silicon Valley and with AI, so the community is a lot more fluid and isn’t just NYC based finance guys anymore.

Core revenue streams/Simplifying the business:

Early on in 2025, it was my goal to diversify a bit out of advertising into more predictable, subscription and fee-based business units. That’s still the goal, but it’s good to stay simplified and not too stretched. So the focus is on the following:

1. My Socials

2. My Newsletters

3. Buyside Hub

4. Advertising Partners where I’m excited about the product and they’re excited to work with me

There’s been a few units I’ve cut, but there are two smaller offerings I want to keep live though: 1) Merch and 2) Banking Playbook.

Merch:

Tbh, Merch may get nixed at some point though. The margins are low for me, some customers expect Amazon level service when it’s a print on demand product, and the costs are higher now cause of tariffs. But 4Q demand for the merch store is generally very strong, so happy to keep this alive given the value people get from it.

Banking Playbook:

This is one of the highest-quality pieces we’ve developed all year that I don’t think gets the love it deserves. When a group of Investment Bankers came to me and explained how they wanted to build a product that could save prospective bankers from spending thousands of dollars on coaching, I was intrigued. When I saw their product, I was immediately in.

Ultimately, we created a product that saves you a significant amount of time and zones in on what actually matters for IB recruiting - all in one consolidated 248-page deck of materials. A way better time vs. money value prop compared to spending a countless number of hours searching for stuff, plus potentially wasting several hours focused on the wrong stuff. Consolidating everything that actually matters in one big deck is an amazing value prop to me.

Notable Partnership Announcement: I wanted to share that I am exclusively incorporating Polymarket predictions markets across all of my properties. I am extremely excited to help work with Polymarket as they started returning to the U.S. this month. I wanted to make an announcement that is comparable to announcements that other media organizations, such as CNBC, have made. I expect more similar consulting arrangements over the coming years.

Where I’m hiring:

Given the above, there’s a few areas I’m hiring out for, see below:

1. HYH Newsletter Research Team: Adding 1 Analyst, maybe 2 here. Looking for a self-starter to help with restructuring and opportunistic credit research. You will conduct deep research on restructurings and special situations, doing heavy research on a story, why it fell apart, and the consequences for investing professionals (particularly the Buyside/CLO Analysts). Restructuring experience (probably through internships) is probably required. Additionally, we will probably up the cadence of private equity acquisition content as well, so we need someone with relevant experience on that front as well.

2. WSR Investing Club: Looking for fractional help with the WSR Investing Club community, ideally someone who already writes about investing on the side

3. Meme Lord: Looking for a cracked Gen Z Analyst who understands NYC finance culture and wants to help on the Guy In Finance side. Ideally has already been making some memes on the side.

4. Other: Anyone else who thinks they can drive value to my portfolio of assets and wants side hustle $.

TV Shows I watched this year

As you know, a lot of my meme content revolves around popular TV shows (The Wire, Sopranos, Breaking Bad universe, Succession, etc.). I think elite TV shows and movies are a great place to get lost for a bit.

I’m extremely glad I watched Boardwalk Empire and The Shield this year. I’ve seen those “top 5 TV shows” already, so I went down the list to the dramas people regard as “a top 10 show, but not a top 5 show” and both shows hit that bill.

Boardwalk Empire probably peaked with the last few episodes of Season 3 but had an incredible cast and I was absorbed with the tragedy of Richard Harrow.

The Shield ran from 2002-2008 and tbh it feels like “Vic and Shane” shaped “Walter and Jesse” in a way. The Shield has a great character cast, including Walton Goggins in his first big role. While some of the storylines hit a dead end, the show has some unreal moments and Forest Whitaker gives an incredible performance.

I also spent a lot of time watching The Sopranos (yet again)…

In terms of new content, White Lotus and Severance were nice hobbies but a little underwhelming, while Task and The Chair Company were refreshing. I’ve been dabbling around with Apple TV a bit too.

Next up, Mad Men (haven’t seen since 2018) and then I’ll rewatch Succession for the first time since the Show ended in ‘23.

Lastly, I wanted to say, Conner O’Malley’s Pipe Rock Theory is unappreciated genius.

It goes on and on and on:

I’ve laid out a lot of info, but ultimately I am building a 30-year-business. The business is predicated on helping people in, or interested in, finance/investing. Who is relevant a year from now, five years from now, and ten years from now is going to dramatically change. You are entitled to nothing and have no god-given right to win. I intend to stake my claim and build great resources & content to help everyone reading my stuff. My business model, with the High Yield Harry brands, are focused on myself working like a dog, and then empowering several smart people to help grow the business and make some bucks.

What is socially acceptable is going to radically change over time. I started this account as an analyst making memes and we’re still very meme-centric and will continue to be, but you shouldn’t be shocked to see things materially evolve over the next 2,5, and 10 years.

I don’t know how exactly AI is going to change things, but what I lean towards is the fact high quality, personality-driven content with large distribution is going to beat out undifferentiated, AI-generated content. I also think that AI cannot create distribution for a business or person overnight, so building up distribution aggressively was a key goal I accomplished in 2025.

So it’s official:

I’ve generally tried to be vague about what shop I could be working at and what type of role in Credit I have/had. I’ve somewhat used disinformation in a way to say “oh I’m in private credit here” and “oh I’m in public credit here” to mix and match my broad experience in credit investing. I’ve seen a lot – from being at big name shops, to being at lesser known shops. I really don’t think prestige matters that much – all that matters imo is bringing home the bacon. Yeah so here’s the big reveal – I left my role recently to go all in on HYH.

Ultimately, I was getting very drained trying to manage two different roles. Arguably, wearing the HYH hat is like running 8 different businesses given how interconnected a lot of things are.

But ultimately, but once I started pulling in more from my memes, month after month after month, than I was in my credit seat, I knew if I took the leap and gave it 100%, then I would be able to skyrocket this.

I had a good run, and tbh a lucky run. But my passion for credit investing started drying up the second I made my first High Yield Harry $. Even when I was only making $1,000 in a given month, that money felt better than anything else. Towards the end, I was ultimately having too much imposter syndrome in credit too, so it felt like it would be good to step aside.

I devoted my 20s to grinding on wall street and enjoying my time in NYC, but at 30, presuming you have enough money saved, you just have to go out and do what you actually want to do. If you don’t take advantage of the window to go do what you want to do, then the moment is going to slip away.

At some point, you have to “make your own kind of music, sing your own special song.”

People naturally have doubts over this type of decision – you see this with creators all the time. Where you question whether they made a stupid decision and the appeal they once had is gone. In finance, I don’t think it does - you just have to stay sharp on the news, keep following the market, keep putting what you learned in the industry to work in an entrepreneurial setting, and to age up your content as you get older. And I also built a large newsletter and a software company in advance of leaving, instead of just relying on social media ads.

Survivorship bias is very real. For every “High Yield Harry” or “Litquidity” there are dozens, if not 100+ of others who fell off the ladder along the way. Many of which relied solely on advertising revenue that wasn’t sustainable and didn’t have the hustle to build tangible things before the window closed. I genuinely think a lot of content creators are screwed because they rely on shaky advertising revenue that is more episodic in nature than they realize. And because they’re not bringing anything new to the table. Additionally, a lot of “course” oriented content that educational content creators provide are going to be decimated by AI.

Despite the move FT, I’m still glued to the market all day, writing on the market and investments, and doing deals/transactions. This is just from an entrepreneurial perspective now vs. from a credit investing standpoint. So in many ways, it’s really the same work I’ve always been doing, but without a Bloomberg Terminal sadly.

I would rather die than be in an office 5-days-a-week – this might sound extreme to some, but I just can’t do it. In 2020, I was introduced to a world where I could work remotely. Once I tasted that, I knew I had to fight like hell to have it forever. And after 5 years I got it.

But this year, there’s been so much early innings bootstrapping and brick-by-brick grinding that I would not recommend this path to 99% of people. Entrepreneurship is not for the faint of heart; every day is a fight, but the business-building aspect is something I’m truly in love with.

And honestly, I’ve burned the boats and I’m willing to go down with the ship.

Ultimately, as an anonymous internet figure who is going to have my name out there shortly, I think what matters most is the reality that everything I say online is something I would tell someone to their face or in person. I am a perennial shit talker. I am extremely competitive. I want to win. And I want to tell a lot of people to pound sand. I lack some social cues, am a bit of a straight to the point person, and say Ralph Cifaretto styled stuff fairly often.

But it’s unrealistic for me to remain a 100% shadowy and anonymous figure. That’s not a fair or realistic ask to partners and to the companies paying me large sums of money. So that’s why the whole 99% anonymity thing is late innings. But the goal is to still run everything as Harry and as the faceless brand.

One of the things that is incredibly uninspiring to me is how many startup founders are obsessed with being celebrities, want to be on covers of magazines, like fancy restaurants and like the social status instead of the brutal behind the scenes grunt work. When you read my stuff, via newsletter or socials, just know I’m doing this for the love of the game and not to sit on the beach all day. The only game I really want to play is a self-improvement game where I can fix and improve upon the areas I can do better at.

I need to be even more vulnerable here too:

A lot of this drive comes from me not being smart. I fundamentally know that I am not smart and have to brute force everything. I have to spend more hours learning something than the average person. I flunked test after test in high school, barely passing the tests needed to get through. I have SAT scores that a lot of you would laugh at. Very poor high school class rankings. Some Cs and C+s in college, because there were some topics I genuinely just wasn’t smart enough to comprehend. On paper, I’m really someone most people would gloss over or not give a look at. It’s never been a good feeling, but I’ve come to terms with it.

Still, despite my acknowledgement that I’m generally quite a stupid and unimpressive person, I ultimately execute and win. There’s a lot of innate intensity and drive that comes with everything I’ve stated above. The one thing I didn’t say is that I show up every single day – K-12 I only missed one day of school, in 1^st grade when I was sick but begging to still go to school.

So that goes back to the Survivorship bias thing - I’m there competing every single day, slowly chipping away and advancing towards what I’ve mapped out for 3 years ahead of time.

Consistency and being able to chip away every day is how you win in a professional setting.

I state all of that though very openly because I know there’s other people reading this who have been labeled the same way and need the reminder to keep pushing forward. You got this. Embrace who you are and don’t lose your intensity.

It’s actually kinda a strength to be overlooked or not really thought much of tbh. That’s how I can walk out of an office one day without anyone realizing they worked with “High Yield Harry”. In many ways, I beg not to be taken seriously. Proving people wrong is an incredible feeling that ultra competitive types like me love eating up. I love throwing that shit back in people’s faces.

One of the great things about this year has been my ability to play the most soccer I’ve played in years. And by far the best soccer I’ve ever played. As many of you as possible should continue playing your childhood sports. The intensity and competitive juice I have is incredibly corollary to what you create when business building. And like athletes, I’m a chirpy guy. I’ve always been a shit-talker, whether it’s on the soccer field or on the internet. I think that’s played well towards a lot of what I do on X, and I’m not backing off on that front.

The other important thing about sports is to have ownership over mistakes and understand where you need to improve for next time. An errant pass, a poor decision, an extra touch I shouldn’t have taken. All things that require accountability and demanding better of myself. The same thing goes for everything re: HYH - I get so mad at myself when I have a stupid mistake or a less constructive thought because not only did I let myself down, but I let everyone who reads my stuff down.

Any Man Can Be Beat on Any day:

I’m often reminded and inspired by LaDainian Tomlinson’s (“LT”) speech he gave to fellow New York Jets right before the Jets had to play the 14-2 New England Patriots in the playoffs.

Being a Jets fan is one of the more painful things in my life. I love this team with all my heart and there’s always new ways for things to fall apart in an excoriatingly painful fashion. The Jets have the longest active playoff drought among major U.S. sports teams, having not made the playoffs since 2010.

The Jets would go on to win the game 28-21, in a game where Mark Sanchez, LT, Shonn Greene, Braylon Edwards, and Santonio Holmes fought aggressively to knock down this arrogant, “we’re better than you”, New England Patriots team.

This is the type of intensity that I love to soak up. While things are set to change, I’m not going to get pushed around and I’m pushing forward into aggressively scaling this platform and doing my absolute best to execute on my 2026 “Value” mission.

I think Entrepreneurs should adopt a “Go Down with the Ship” mentality - where they have to treat something like everything.

For me, the High Yield Harry portfolio is everything. Beyond my own personal whims, I serve at the pleasure of everyone who sticks with me. It’s a voice, platform, and a tool for finance professionals and I’ll go to war for you all.

I plan to approach 2026 and the coming years with the same intensity to deliver that I’ve had for the past few years. We are just getting started.

Onto 2026.