A Conversation with Jerry Diao (Richard Toad)
From actuarial consulting to building the most influential career brand in public equity research
Jerry Diao is the founder of Richard Toad — the go-to resource for anyone trying to break into or navigate the public equity research industry. He’s built a subscription job board, a fund database covering 1,000+ U.S. hedge funds and long-onlys, and a networking course — all bootstrapped, vibe-coded with AI, and scaled through content.
Before going full-time as a creator, Jerry worked in actuarial consulting at Towers Watson, went to NYU Stern for his MBA, interned at a deep value hedge fund, and spent two years covering SaaS at Wells Fargo equity research alongside the famed bank analyst Mike Mayo.
We covered a lot of ground:
Jerry’s Background — The underdog-to-Wall-Street story (Shanghai, Cal Berkeley, wrong major, actuarial exams, Moody’s, NYU Stern, Wells Fargo)
Actuarial Role + Transferable Skills — What healthcare benefits consulting taught him about mentorship and professionalism
Leaving the Startup Hedge Fund — How he came to terms with a bad fit and cut losses
Mental Health: HF vs Entrepreneurship — Resilience, nonlinearity, and the acceptance of turbulence
Richard Toad Business Overview — Job board, fund database, networking course, and the power of reduction
What Jerry Cut From the Job Board — Why he dropped public credit coverage
Vision + Delegation + Lifestyle — AI replacing contractors, VA unlocking morale, and the recruiting opportunity
Investor-to-Creator Trend — Why hedge funds are going on podcasts (talent, succession planning, and private capital TAM expansion)
Process on Podcasts vs Deep Stock Dives — Dan Sundheim, Cliff Sosin, and the value of sharing process
Biggest Mistakes: Industry Insiders — Reactive job searching, not networking, and underestimating personal relatability
Biggest Mistakes: Breaking In From Outside — Stock pitch requirement, no recruiting season, and building an online brand
Advice for Emerging Fund Managers on Hiring — Talent degradation, posting in the wrong places, and owning your audience
Where to Find Jerry — “Inside Equity Research with Richard Toad” newsletter
Full Transcript
Or listen on Spotify:
INTRO + JERRY’S BACKGROUND
Bryan: Thanks again for taking the time today, Jerry. I really appreciate it, and really looking forward to speaking with you, and it would be great if you could just kind of give our listeners a little bit of an overview of you and your story, and how you got to the position that you’re in today to kick things off.
Jerry: Awesome, thanks, Bryan. A real, real honor. Yeah, so I have... there’s two versions of me. So maybe I’ll go with my brand first — I’m the founder of Richard Toad. I’ve been running it since April of 2020. But now, let’s take a step back and introduce who I am as a person.
My name is Jerry Diao. I went to... I’m from China originally. I am from Shanghai, which makes it easier, because I don’t need to introduce where that is. I came to the States when I was 15, and went to Cal Berkeley. So my story has always been kind of the underdog to Wall Street story.
Picked the wrong major, had really bad grades in college, and I saved my career by passing this thing called actuarial exams, because I was a statistician by training. So I had to save my career at the very beginning by having to take these very gruesome exams and landed an actuarial consulting job as first job out of college. That’s where I worked in San Francisco.
After the first job, I went to New York City, and that — still looking back — is the best career decision ever in my life so far. The last job before my MBA at Moody’s, I met my colleague, Eric, who sat in front of me. It’s really funny — there were the four of us sitting in the same row. I became a creator. The girl sitting behind me, she’s a creator too — she has like 10x the following as I do, doing dog accounts. So it’s really interesting.
Eric sat in front of me, he introduced me to stock research, and now Eric is a very close friend, and he will come back to the story shortly. At the time, I was pretty hooked into stock research, read all the very marquee books in investing that tends to be value-oriented — the Margin of Safety, Intelligent Investor, and The Most Important Thing by Howard Marks.
So I thought it was kind of the good juncture to use MBA to rebrand, given I was a purely technical training person with no business background whatsoever coming out of undergrad. So I went to NYU Stern, and I interned in Sales Equity Research, covering cable and media. Second school year during MBA, I worked at a deep value hedge fund for a founder who began his career working for Carl Icahn.
That was a very interesting experience. After MBA, I was kind of trying to get into this research space, so most MBA students will hedge by recruiting for both sell side and buy-side research. Because there are only that many jobs, and that’s particularly true for MBA.
I asked Eric to refer me to Wells Fargo, where Eric was working for the famed bank analyst, Mike Mayo. I ended up getting a job covering SaaS software. Eric became my colleague the second time.
I worked on the sell side for 2 years, and left Wells Fargo in 2020, and moved back to California to join a startup hedge fund. Over time, it realized it was a really, really bad fit. So I left in early 2022.
That transitioned me into this whole social media side of things. So the genesis is, in 2020, not when I started a hedge fund, but when I started on — as I end my sell-side career — during COVID, I was getting anxious about getting into the buy side, and I really wanted to vent about sell-side research, about how the misalignment of incentive, how ridiculous the profession is. Obviously, most buy-side investors trash the profession on a daily basis, and so I wanted to do that.
I went and did it. It’s really funny, because I don’t know why I decided to use Instagram, because Instagram is actually the worst platform for text-based memes. But I just did text-based memes — kind of the insider overheard type content in text format — and it really resonated.
I was doing a lot of things that didn’t scale. At the big players — like the Litquidity, the High Yield Harry of the world — but one account called TradesandRaids, he started reposting my stuff, and that was kind of the initial crossing the chasm and got the snowball rolling. So, one to two years in after I started creating on Instagram, most people who work in sell-side research globally have become my followers.
Fast forward to 2022, after I left the buy side. I thought about just finding a better fit, buy-side job. It had to be open to location. Had conversations with Boston, New York, Miami firms, but I thought about it — I’m into my mid-30s, I just didn’t want to relocate.
I was talking with a few of my friends, and one of my friends who still works on the buy side, Justin, he said: “You know, you got this massive following. I know you never thought about monetizing or becoming an entrepreneur, but why don’t you just give it a shot?”
He kind of ignited something within me of the whole Jeff Bezos 80-year-old deathbed comment. It’s like: you’re looking back, you got this social media following, you know you’re helping people for free, you’re clearly effective, and you’re doing this at scale thanks to internet and today AI.
So I said okay, I’m just gonna go for it. I really had no idea. But I’m not gonna dive deep into how I found product-market fit. I said okay, I didn’t have much to lose — I was making zero income. So I went founder mode. And 4 years later, I’m consistently doing 5-figure monthly revenue, and kind of here we are. Product market fit, followership still growing, have gone through multiple algorithm changes where I stopped growing and then re-accelerated. That’s my story.
ACTUARIAL ROLE + TRANSFERABLE SKILLS
Bryan: So many interesting pieces to that. There’s two that I want to follow up with. Your first role, the actuarial role — I’d love to hear more about that and just what that experience was like, and if you feel anything that you learned there is transferable into either investing or what you’re doing today.
Jerry: Oh, man, that’s a great question. The short answer is, there is still a fantasy football league of the people that I work with out of that first job. The firm is publicly traded — it’s called Towers Watson. They’re one of the biggest — if you know like Aon and Marsh McLennan, they’re the competitor.
It was 2026, so I joined in 2010 — it’s like 15 years running, so I still have these friends who I play fantasy football. That tells you a lot about the relationship.
My role there was healthcare benefits consulting. Think about when you work at a big company — you get benefits. The big company, what you didn’t know is they actually set aside a pile of money to pay expected claims of their employees. That’s called self-insurance. We as actuarial consultants help them set the rates for how much to reserve for expected claims, and what is the contribution strategy — how much the employer will set aside versus how much you will pay out of your paycheck as the cost sharing between the employee and the employer.
We do a lot of other things. One of the things we do is called plan design — in the medical insurance environment with the politics. We don’t want to increase the rates too much, so we have to think about increasing the copay, increasing co-insurance, narrowing the network. There are a lot of things that you can do to advise big employer sponsors as to how to reduce costs or reframe the cost increase.
So many of my good habits as a corporate professional today, even today as an entrepreneur, came from that role. I had so many great mentors, not just from the technical skills, but also from just understanding what your responsibility is as a junior or a senior person at any organization, whether that’s a hedge fund or a company or an entrepreneur. I’m so grateful I met some of the greatest mentors in my career from that job alone, and one of whom wrote my MBA recommendation letter.
LEAVING THE STARTUP HEDGE FUND
Bryan: And then the next stop I wanted to ask about was just your experience joining a startup hedge fund. I’d love to hear more about, you mentioned that it wasn’t a good fit, and I’m curious, maybe more specifically, just your process of coming to grips with that, and then how you decided to take action.
Jerry: So first part is — you can’t change external factors. In this case, you’re working for somebody — so I worked for two people. Combined, they have like 25 years of experience. They came from the same firm.
I’ll say the short answer is, it’s the same thing as what I do today as a creator and an entrepreneur — I just was fighting really hard to be useful to them. I couldn’t come up with the next company that will beat earnings, or come up with the next cheap, actionable idea because of some geopolitics — my boss is a basic materials energy guy.
I came to terms that: one, I couldn’t change how they think about investing — they wouldn’t suddenly be thinking about 3-5 year earning power of a business. And the other part is, there’s a gut feeling — once I understood well enough that the style they operate under at the firm and at their predecessor firm is precisely what I did not want to be involved in at all.
The short answer is they came from a firm that is what I call a single manager multi-manager style — think like a Holocene Advisor. There’s a single founder, but they have sector heads, and my big boss/PM was one of the sector heads who was also a partner. That just didn’t work for me. I very quickly understood they were a low net, high portfolio turnover long-short.
There’s a gut feeling that I just gotta go. If you know you cannot add value — and because I was set in my ways as well — I knew I was making no effort to converge to ever being super useful to them. That’s detrimental to the firm. There’s no career prospect for me, and it’s a waste of time for them.
I think the optimal way is to cut losses, like an investor, and just say let’s part our ways. I talked to a few people whose opinion I respect, and they say, yeah, in this situation you should just leave. So that’s what I did.
I have absolutely zero regret about it. My mental health was better, I was forced into this entrepreneurial situation, which I brute forced my way into making it work. When you know it wasn’t working, it wasn’t working. There was no path of it changing.
MENTAL HEALTH: HEDGE FUND VS ENTREPRENEURSHIP
Bryan: You mentioned your mental health improving after you left a hedge fund, and then entrepreneurship obviously comes with a lot of its own uncertainties and stresses. I’m curious to hear more — how would you compare the two?
Jerry: There is a lot of similarity between entrepreneur, investor, founder and creator. Creator is also a zero to one. You’re all evaluated on outcome. You can work 80 hours and generate no alpha. You can do a lot of content and get no views. You can do a lot of things and generate no revenue as a founder because you have no product market fit.
All of them have the great thing — some sort of leverage involved. Hedge funds is leverage of other people’s capital. Founder is leverage of so many things — if you raise financing, other people’s capital, you have labor that don’t get equity, so you’re getting leverage out of labor. As an internet founder, you get leverage out of internet, LLM. Creators same thing — internet, LLM, you can hire people to 10X. All the big creators — Alex Hormozi, Cody Sanchez, MrBeast — they all have a team. They’re a content machine.
The mental side — it’s similar too. You gotta be resilient, you gotta be resourceful. There are obviously a lot of people who tell you you should never give up, and that’s completely true. But if you don’t give up and do the same thing, you will just continue to fail.
There’s this part of paying attention to what your audience and customer want. For investors, you’re paying attention to: under that pattern, you made that decision, that clearly turned out to be wrong — how do you improve your investment process to be more protected from your own intellectual blind spots?
Over time, yes, there’s gonna be unforeseen errors, but at least you don’t make another unforced error because you keep making the same mistake. That actually gets you fired.
Acceptance of nonlinearity. When you work at a company — well, for a hedge fund, you do have a base salary too, but that’s not what people go to hedge funds for. There’s some downside protection. But entrepreneurship is probably the most extreme — there’s no downside protection.
You have to accept things gonna be up and down. Having worked at a hedge fund prepares me really well, because you have portfolios that were always moving in total value. As an entrepreneur, today I made $500, tomorrow $600, and sometimes it’s a weekend where people don’t want to pay for things, and then suddenly Monday it surges — I see it on my Stripe every day. The acceptance of turbulence — that’s very transferable on the mental side as well.
RICHARD TOAD BUSINESS OVERVIEW
Bryan: Can you give us an overview of what the Richard Toad business looks like right now, and how that developed over time? What are the different components, and how did they come about?
Jerry: Today, mainly three parts. The first product-market fit was the subscription-based job board access. I might be the only person in the industry that sells to job seekers. I think most job boards monetize on the employer side. But the product is just so effective in maximizing shots on goal to people that a lot of college students and people inside and outside the industry both value what I do.
Because I was a creator at start, entrepreneur second, my distribution was already there — I just didn’t have a product. Really quickly, as I reached product market fit — talk about 3 to 4 months — I knew the numbers were big enough for me to go full-time.
Bryan: You knew from the viewership numbers you were getting?
Jerry: Oh, no, just from the revenue number. Once I start launching the product, given I just promote on my Instagram and my newsletter who are all in the industry — they’re like, “oh my god, this product.” Even people in the industry, they’re like, “if you want to break into public equity research globally, this is the guy, this is the product.” People didn’t do that because I pay them — people do that because this is something that genuinely helps them.
I doubled my revenue last year because I’m paying attention to where people have problems. I launched a fund database — doing the dirty work of literally digging through all the public filings of a thousand plus U.S. hedge funds and long-onlys across regions. Categorize them by style, founder lineage, and region.
Because on that finance forum, a lot of college students are asking “hey, I want to recruit in Atlanta — who are the hedge fund players there?” I know these things, they’re already in my head, it’s just not systematized. So I launched that as the paid tier of my newsletter.
The third part is the networking course. I teach my audience how to do the diligence work I am sharing with them in the fund database — how to read a Form ADV Part 1, Part 2, what to dissect to get insight as to what’s their strategy, what’s the founder’s name. It’s all in the public filings. But the raw data extract is actually 15,000 funds, only of which 900 to 1,000 are actually public equity funds — because private equity, wealth management, all these alternatives also file Form ADV. That’s my value add — I know who is actually a public, institutional, public equity, active investor.
In that course, I teach how to diligence funds and how to present yourself and how to get liked by hedge fund founders so that you might just tip the scale against the Ivy League who have private equity experience.
How I build the product — I built it and refined it over time, because as a creator I know it’s better to launch, get feedback, and refine. AI/LLM only help me, not hurt my business. I didn’t know how to code — a lot of the underlying tech stack is just HTML, CSS, and JavaScript, and I knew none of that, but I just prompt and dynamically fix as I want to improve — add a button, add a filter, make it sortable.
You know this as an investor — success in investing, creator, and entrepreneurship actually comes from reduction, not addition. Over time, I want to do less products and do those products the best in the industry. Like cable stocks — ARPU, sub, lifetime value, CapEx — that’s pretty much the gist of the story. It’s about reduction.
Earlier this year, I’m already shrinking the scope of my job board. Turns out not many people left because of my shrinkage — it saves me a lot of time in terms of executing the product on a daily basis.
WHAT JERRY CUT FROM THE JOB BOARD
Bryan: What did you decide to cut out of the job board?
Jerry: When I launched the product — knowing the industry is very small and shrinking — I wanted to maximize the addressable market by covering public equity, and I am qualified to cover public credit, because public credit doesn’t tend to need investment banking experience. They can come from just having worked at a rating agency or coming from public equity research.
I always marketed the job board as equity research job board, so it makes no sense to say “we also cover public credit.” There is a competitor in the market that is lumping private credit and more deal-driven credit roles with public credit.
Some people signed up just for my public credit value add, and they kept on paying for it. But from the website views, I noticed most of my customers aren’t even clicking on the credit side of the job board at all. So I was like: if I lose a few hundred bucks a month, and I save 30 minutes executing that on a daily basis, then it’s a good trade-off — I can easily make it up by making the equity side better.
VISION + DELEGATION + LIFESTYLE
Bryan: As you think about where you want to take the Richard Toad business over the course of the next couple of years, what gets you most energized? From a business perspective and also from a lifestyle perspective — are you starting to get into delegation and automation?
Jerry: I actually can answer the second part first. I do have two contractors — they’re not 1099 employees, I’m using freelance platforms. Unfortunately, I’ve been stealing work from them because of AI. There’s a task where I need to repeatedly download a PDF file 200 times by inputting different names, and I just asked ChatGPT to write a Python code and it works perfectly. So I’ve been stealing some billable hours from them.
In terms of delegation — my virtual assistant has been incredible in amplifying my message across platforms. I create one piece of content, and I post on four platforms on a daily basis. Sometimes it goes viral on one platform, sometimes on another. By spreading my own shots on goal, it’s been really helpful for my brand. Operationally, it’s just really mundane to schedule those content across four platforms myself. That’s been a huge morale and time unlock. The morale part even bigger — you gotta do stuff where you add value the most.
In terms of vision — we’re finance people, we like to make more money, let’s not be hypocritical. But at the same time, I want to do things well in few areas. I do see a big opportunity in recruiting. That’s natural by the fact that I own the entire sell-side research audience, and increasingly on LinkedIn at least, all the major banks’ director of research and hedge fund founders are my LinkedIn followers. There’s something I can do by being that bridge between the two. Executing that is the hard part.
The other vision is, I do love learning myself. I want to benefit others, at the same time grow my written following both on a free and a paid basis. So there’s more angle on the paywalled newsletter side for sure.
Lots of optionalities because you’re a creator, you have a distribution. But all require execution. I was just focusing on doing the things I already have product-market fit really well.
We talk about removing the credit side — to compensate, I expanded geo coverage over the last two years since launch. Since January 2024, I’ve added coverage of Canada, UK, and APAC jobs in major financial hubs. Over time, there’s definitely opportunity to profile UK market, Hong Kong market, which is a really big market.
INVESTOR-TO-CREATOR TREND
Bryan: Another topic to touch on — this transition we’re seeing a lot of people make, or the blending of the lines between hedge fund founder/employee and creator. You’re seeing more and more hedge fund founders starting to go onto podcasts. What’s your view on what’s going on here?
Jerry: A few things. One — you have to sell. Things have changed in terms of the labor market. People know money is not relatively going into public market, and one part is deservedly — most funds don’t deliver what they promise clients.
Increasingly, the laborers are coming from the younger generations. They need to be sold that hedge funds are a place — because hedge funds and public equity in general have always operated under the assumption that secrecy is actually good. People don’t know what the hell they do and how the hell they do it.
The founders realized: “Oh, we’re losing this candidate to some VC funds, or to Anthropic, ChatGPT, OpenAI, or some hot startup.” That’s a fact. Compensation only — these AI companies are paying a lot. I’m not a big believer of pay. I believe in ownership of something that grows. But most people are still motivated by upfront pay, and even upfront, the startup world is very competitive. Not to mention, they by definition need to attract VC funding, they’re marketing like crazy. They have a lot of publicity, they’re well understood what problem they solve.
All these public equity funds understand that, noted that. Podcasts as a business concept is really taking off. There’s a lot of money in podcasting, so all these podcasters are competing to get the best guests. Who’s the winner when there’s so many competing podcasts? It’s actually the audience, because we get access to Dan Sundheim going on 3 podcasts, Todd Combs going on podcasts. These people never talk for an hour on their story, how they invest, all these lessons that take them decades.
One is they want to market their brand, creating more understanding. The other thing — all the public investors understand where the money is, and as part of the marketing into a different audience, they’re going on podcasts to pitch a vision of them getting a TAM expansion into the private side.
Why Dan Sundheim went on Cheeky Pint is because he’s raising $2 billion of private money to do pre-public. Because there’s abundance of private capital today, companies are shifting to appealing to the private player, and the public investors have less company to invest in. They need to get earlier in the fundraising cycle, by doing growth equity or pre-public financing to get ownership before they go public, by which, by then, arguably some of them the upside is completely gone.
The venture capitalists, to the extreme, have a dedicated media company inside the venture capital firm.
Another thing — the hedge funds and mutual funds need to market because they need to attract enough talent to think about succession planning. A lot of the funds still haven’t — it’s still run by the original founder. Some of them have — Lone Pine has, Viking Global has — but Coatue is still run by the Laffont brothers, Tiger Global is still run by Chase Coleman.
Over time, it’s not sustainable because this is a young person’s game. If you can’t get enough talent in the pipe, who will be the next wonderkid to take over the firm?
From my vantage point, people always know that the candidates have trouble getting to the hedge funds, but I know the hedge funds actually have trouble finding candidates, too, especially when their criteria is so rigid. So by going on podcasts and marketing how they invest, their process — it helps find aligned candidates more easily at scale. When you go on Invest Like the Best — you know the audience is very relevant — a lot of them want to work at a hedge fund.
PROCESS ON PODCASTS VS DEEP STOCK DIVES
Bryan: I’m curious if you think there’s a trend, or maybe even an opportunity for some hedge funds to start to shift the way they approach this mystique and secrecy thing. If you compare it to the tech world — Lex Friedman with people from OpenAI or Anthropic talking cutting-edge research for hours. Even though it’s great to have fund managers on podcasts, a lot of it’s kind of like marketing. You’re not gonna have a D1 analyst come on and talk about the latest stock. Do you think there is any trend toward more value-additive content?
Jerry: I think there is value-add. Just by mere fact that you can get access to Dan Sundheim. He went on Invest Like the Best, he was at Cheeky Pint, on David Rubenstein’s Bloomberg interview. The Cheeky Pine and the Invest Like the Best are more recent. They’re valuable to an inexperienced investor like me.
This is the whole thing about investing — the most value you can give going on podcasts as a professional investor is the process. He can talk about investing in GE Vernova, the turbine business tied to power generation — you know there’s a secular trend because of AI data center demand. The thesis is simple — he can’t sit at a podcast and talk about it for two hours. He has that information.
But at the end of the day, the process is gathering the information, which at a hedge fund like D1, he can be having his people do that for a month. Him distilling down to two, three things on a podcast is not gonna help you become a better investor, because this guy has done this for 30 years successfully. But just hearing that framework itself is already very helpful.
Yes, definitely there is part of it. There is some marketing, but I think he genuinely just wants to share what his process is.
Bryan: It’s interesting because it wouldn’t be an accurate representation of their process to go on and talk about one stock for an hour or two. Whereas someone like Cliff Sosin has had fantastic episodes on Invest Like the Best where he just talks about Carvana for two hours. It’s because they’re different strategies.
Jerry: Yeah. Cliff is very concentrated. We all saw that ride with Carvana with him — at one point, 50% of the book was in Carvana or something, and 30% in Credit Acceptance. Whereas Ricky Sandler goes on and explicitly talks about liking it a little bit more diversified — so some parts of the book is always working while the other part is not.
For Cliff, he’s just all in on something, then that’s all he talks about. Concentration plays a role in how they think about their process and how deep they go.
BIGGEST MISTAKES: INDUSTRY INSIDERS (LATERAL MOVES)
Bryan: One of the last topics I wanted to touch on — now that you’ve gone so deep into the recruiting market, I’m interested to hear on both sides. Let’s start with people who are trying to move laterally within the industry. What are the biggest mistakes you see?
Jerry: The biggest one — so many industry incumbents are still so reactive to the job search. They look for a job when they need a job. That is a cardinal mistake.
The moment you’re on the buy side, you don’t realize how advantageous you are, because you have a platform to be building your brand equity — yes, inside the firm, but also within the buy-side ecosystem.
I’ve done so many client calls where this buy-side person who’s done this for 8 years, they’re like: “Okay, I need to get a buy-side job. What should I do?” At least they know they won’t find any job posted online. But they’re like, “what should I do?” And I’m like: you should have a list of contacts where you should reach out and say “hey, I’m Bryan, I’m looking — do you know anyone who is looking to add headcount?” That should be how it works. They don’t have a network, they’re just sitting at their Bloomberg terminal doing work for their boss — which is totally their job — but there is a part of the job where you should preempt, like, thinking about the next seat.
They don’t know networking is a must. They don’t know who is who in hedge funds — which is what my fund database helps with.
I remember talking to a junior at a wide-moat shop out of Chicago. I told him I love wide-moat investing, I have a good friend at this other white moat shop out of Miami, and he’s like: “Oh yeah, we have a list of firms that we will cold-reach to try to poach people to join our firm. Here, take this list.” Do you know how much time that saved me in terms of whom to reach out? Then I look at the list — oh I know this shop, I know that shop, they’re all wide-moat shops, that checks out. Then I know whom to reach out.
Another point that’s more at an advanced level that I’m recently discovering — people outside and inside the industry underestimate the power of relating on a personal level.
Because I profile investors — their story — on a daily basis, and a lot of my audience will comment “how the hell did this guy get into the industry?” I’ll give examples:
Peter Lynch — famous story — he caddied on a golf course for Fidelity’s president.
Art Samberg (Pequot) — studied aerospace engineering at Princeton, got the sell-side equity research job because the director of research at Kidder Peabody was also an engineer. Relatability.
Kelly Granat (Lone Pine) — went on podcasts telling people she loves people who play sports, because she was varsity tennis at Harvard.
Dan Sundheim — told Patrick O’Shaughnessy that he likes strong communicators.
These are very big clues when you are pitching yourself to hedge fund founders. You might just tip the scale just because you have something that these people personally like. Yes, these hedge fund founders are billionaires, they’re high up in the world, but they’re also human beings. If you can relate to them on a personal level, that might just tip the scale when you have that imposter syndrome — you might lose against an Ivy League 2+2 type, but maybe you’re a varsity lacrosse player at a Division II school, and you go sit in front of Kelly Granat at Lone Pine and say “I’m a competitive sports player.” Maybe you don’t get the job, but you earn the spot to have a conversation.
BIGGEST MISTAKES: BREAKING IN FROM OUTSIDE
Bryan: And how about for people looking to break in from the outside — either early career professionals or college students?
Jerry: Let’s start with a simple one. They didn’t understand that this profession — they didn’t take a step back and think about why hedge funds and long-onlys want to hire from investment banking, private equity, and equity research. The reason is because they need to know how to do the job. Somewhat, not entirely, but they need to know how to do the job before they get the job.
The biggest punchline for aspirants — even for people currently in IB, PE, and equity research — do not ever try to scheme your way into the profession. 99% of the cases, you will need a strong stock pitch to get hired. There’s no way around that.
There are people who ask how do I limp my way into the profession? Because day one on the job will be: “Hey, Bryan, my buddy was following this idea, seems interesting, take a look. Let me know what you think.” That’s all the instruction you’re gonna get. I’m not gonna say step one, read section 1 of the 10K.
Because it’s public equity, all the skill that you need to equip yourself is on the internet today, or in a book. Just go figure it out. If you don’t want to go figure it out, don’t be in this industry.
Same issues for incumbents — not knowing networking’s a must, not knowing who’s who, not knowing the power of relating.
The other big issue: No recruiting season. People in the three feeder professions — IB, PE, equity research — didn’t know there is no such thing as recruiting season for public equity. They hire whenever the hell they want.
Investment bankers are probably the biggest offenders — they’re like “okay, what’s the recruiting season for hedge funds?” There’s no recruiting season. Someone left, they’re hiring, they’ll post a job. You’re lucky you see a job posting.
Concrete example: Lone Pine just publicly promoted Rahu as the third co-PM with Kelly and Dave Craver. As a result, 3 senior analysts are leaving, all starting funds separately. That’s probably telling me there might be headcount openings at Lone Pine. You gotta pay attention. That’s on Bloomberg. But if there wasn’t a promotion, they wouldn’t be hiring again for 2 years.
They just don’t hire until they need to. If you miss that boat, they’re not gonna hire again this time of the year next year. So there’s no recruiting season.
Last thing — everybody should build an online brand under a compliant framework.
There’s so fewer investor professionals bouncing ideas on Twitter. I heard that crowd has flocked to Substack — increasingly a social media platform where people talk about ideas. Some buy-siders I talked to said Substack is a lot better for shooting ideas than Twitter.
Provided you know what you’re doing as an investor, if you’re aspirants outside looking in and super passionate, you should build an online brand. For outsiders, that’s compliant by nature. If you’re inside at a hedge fund, that’s tricky because you have to disclose. But I think for smaller funds the PMs will let you bounce ideas.
That should be part of your job search motion. Most is push — cold-reaching out, doing coffee chats, submitting applications (least effective). The last part is pull — build a brand authority online, and people come to you. I know people who got hired through podcasts, through online presence. A gentleman at an Ivy League school has a great podcast where he gets portfolio managers on — he got hired at a very respected long-only. How does that happen? You attracted an audience who might give you a job.
Internet lets you do that at scale.
ADVICE FOR EMERGING FUND MANAGERS ON HIRING
Bryan: And on the hedge fund manager side — with how competitive things are, competing for talent against the Citadels and Millenniums of the world. If you’re an emerging manager with a decent track record, maybe running for a couple years, good pedigree, starting to raise assets — it’s time to hire. What advice?
Jerry: First thing — just be open-minded about where talent comes from. My PM hired me. I don’t have a very good background — I don’t have the traditional IB/PE background. My PM has a pretty good background — just an undergrad, which tells you how successful he is. He didn’t need to do an MBA. I did an MBA because I had to.
Be open-minded about where talent comes from — especially in terms of their pre-buy-side work experience, not from IB/PE. I’ve seen this with older founders. Be open-minded about people’s past. Even the best stock pickers are only above 50% hit rate. So why only hire people who never failed in their life and career?
I talked to a recruiter who tells me a fund in Seattle still imposes SAT score and GPA requirements. For someone hiring a senior analyst who’s out of college for 10 years — does it really matter? I had a low GPA, I got into a hedge fund. So don’t be so rigid and elitist.
I want to use your platform to message this: There is a massive talent degradation in the entire profession — sell side and buy side. Why? People flock to where the money is, and money is in tech and AI today. That’s a fact. You don’t get to make that rule.
And the very best talent are doing what I do — they have a vision. They might not have product experience, they will vibe code something and find product market fit and make nine figures. I go to these founder events sometimes and these guys don’t even know some of the television shows I’ve seen, they don’t know who Kobe Bryant is. That tells you how young they are.
On posting jobs — there are a few issues. They post at the wrong places. It’s probably better to post at a verticalized job board than on LinkedIn — LinkedIn is a mass audience, not verticalized by finance. Post where candidates have high intent for buy-side jobs.
They don’t know the social media game. They should learn by talking to LLM, or hire a Gen Z as a free intern — ask them how social media works. If you have a job post, understand what a hook is, what a call to action is. “We’re a $200 million long-short hedge fund investing in old economies” — versus having a hook that intrigues the audience. Maybe 10x difference in engagement, and engagement funnels down to clicks.
I was in Los Angeles in January, talking to a friend who founded his own fund — he’s looking for an intern and doesn’t know where to post. I offered to shout out to my 8,500 newsletter subscribers.
But I also advised him: Fund managers should have an owned audience. The most loyal audience is newsletter. Where you can attract highly engaged candidates, LPs, and all sorts of relevant people within the ecosystem of running a fund. You find aligned candidates who believe in your investment style.
VC has perfected this long ago — a16z has a media arm for sourcing deals. Brett Caughran sponsors stock pitch competitions — part of sourcing talent. John Griffin of Blue Ridge — I know people from Columbia Business School, highest performing students in his class got hired. John used to teach at Columbia, he went to UVA, used to teach at UVA. Why do these people teach there? Part of it is sourcing candidates. They know their dear alma mater attracts and filters the most qualified, highly engaged candidates.
The punchline: the worst way is to use the traditional channel to source candidates. Podcasts — if you go on a podcast, say “hey, we’re hiring,” you shout out on Patrick O’Shaughnessy or the Acquire podcast with Ted Seides — you’ll be flooded with emails. People need to be aware of how information gets disseminated today.
WHERE TO FIND JERRY
Bryan: Where can people find you, Jerry, if they want to read more of your content or sign up for your newsletter?
Jerry: It’s really simple — just type in “Richard Toad” on Google and you will find all my assets across the internet. I operate kind of like a casino where you can’t leave. You go to my Instagram, you will see my newsletter, you go to my newsletter, you’ll find all my socials. You can engage with me across the channel of your preference.
You’ll get most value out of my newsletter — it’s called “Inside Equity Research with Richard Toad.” That’s where you get all my career tips, all the investor bios, and the fund database if you want to really buckle down and target and maximize your shots on goal for your buy-side search.
Bryan: Well, awesome. Thanks again for your time today, Jerry. I really appreciate it.
Jerry: You bet, thanks for having me. Real honor to have this conversation. Thanks for having me.