B-Schooled Podcast Episode #298: Wall Street Oasis Founder Patrick Curtis on Breaking Into Finance

This transcript has been lightly edited for clarity and length. Timestamps refer to the audio.

Stacy Blackman: Welcome back to Paths Less Traveled on the B-Schooled podcast. Today we’re talking about a path that takes insider knowledge of the elite finance world and turns it into an entrepreneurial success. I’m joined by Patrick Curtis, the founder and CEO of Wall Street Oasis, a platform that has reached millions of finance professionals over nearly two decades.

Patrick started his career on a traditional path: investment banking at Rothschild, followed by private equity, before getting his MBA at Wharton and building Wall Street Oasis. Patrick, welcome to the show.

Patrick Curtis: I really appreciate you having me. Thanks so much.

Stacy: I want to start with your career pre-MBA. You were already living the dream for many of our listeners, right? IB analyst at Rothschild, moving into private equity. That’s the stated dream career path for a lot of our MBAs and pre-MBAs. Why did you step off to get your MBA at Wharton?

[01:16] Patrick: It’s important to note that, looking back, my first step was very difficult. Even just landing the role in investment banking at Rothschild was hard, because I was graduating in 2002, right into the dot-com bust and right after 9/11. I felt very fortunate to land that first role. It was one of my last interviews, and I struck out at a whole bunch of interviews leading up to it.

More importantly, my transition to private equity was even rockier. I actually got fired from my first private equity job within a few months. So not everything was rainbows right out of the gate.

That experience of losing my role pretty early on was one of the reasons I was a little more open to building something on the side, almost to protect myself. There was some insecurity around having those struggles early in my career. You go in a little naive at 22, thinking that if you work hard, everything’s going to take care of itself. When it doesn’t, you spend the rest of your career looking over your shoulder.

So to answer the question of why I went to get my MBA: it’s one of those things that raises the floor on your entire career. It may not mean you’re going to be the CEO of the next Fortune 500, but with the network and the knowledge you build, you’ll almost without fail have a decent career and a good job, where you can raise a family and have that security.

When I got back into private equity and was trying to decide on my next step, the MBA felt very natural. I still had that fear. I’d already started building Wall Street Oasis on the side, and I figured this would give me time to see whether the entrepreneurial thing was something real.

It would give me some insurance and some upside, but mostly it would give me the safety of a really strong network, so that if something like that ever happened again, I’d have something to fall back on. That was the main impetus.

Stacy: So you started building WSO pre-MBA.

Patrick: Pre-MBA, yes.

Stacy: And it was tiny.

Patrick: Very small. It wasn’t really a business. It was all just my community.

Stacy: A fun little side gig, a side hustle, as we call them now. You said so many interesting things there. A lot of times when people look at their career, they trust the big company that might hire them to give them security more than they trust themselves. Having that kind of shake-up early on maybe showed you it’s not always what it seems, and that investing in yourself is a good move.

Patrick: Part of it was also that in my first few years out of school at Rothschild, the hours were very long. It was a tough stretch for relationships with friends and family. You give your whole life to the role right out of school. Part of me looked at that and thought, is this the life I want long term? That’s one of the reasons I transitioned to the buy side. I told myself I needed to try something new after two years and figure out whether this was really what I wanted to do. Investing sounded really interesting and exciting.

And I loved private equity. I thought it was fascinating, meeting different entrepreneurs and all of that. I never thought of myself as someone who was going to be an entrepreneur. I wasn’t dreaming of it. It was more, hey, I should be doing something else just to see if I can. It wasn’t some grand vision of what Wall Street Oasis was going to become. It was just, let me try something and start something.

Stacy: It was the same for me. So often you find a need through your own experiences, you play around with it, and it turns out other people share that need. But that doesn’t mean you don’t have to hustle and work really hard to bring it to fruition.

Patrick: I always say I was working about 90 hours a week at Rothschild. When I went to private equity, I was working only about 60 hours a week, and I felt like I was on vacation. So building a business on the side after hours just got me back to where I’d been.

[06:22] Stacy: So you go to Wharton and focus specifically on entrepreneurial management. Coming from finance, which is such a structured world, what were some of the mental shifts or aha moments at business school that prepared you to build your own company?

Patrick: What investment banking and private equity give you is incredible: really strong financial modeling, a good sense of profit margins and product mix, all of that at an analytical level. But where I was particularly weak was marketing and understanding strategy and business in general. Business school rounded out my profile. Being in those marketing classes, understanding what any of it even meant and how to look at different business models, was really important.

My classmates at Wharton accelerated the business by maybe five years in my first year alone. Having really smart people around you who had worked in ad ops or on vertical advertising networks, and even understanding what those were early on, let me start bringing in enough revenue to reinvest back into the business. If I hadn’t gone to Wharton, WSO wouldn’t be where it is today. More importantly, it might not have even survived.

The entrepreneurial management classes and the marketing classes were great, but the classmates mattered most. We were using WSO as a project in some of those classes. On top of that, there was the Venture Initiation Program, which gave me access to other entrepreneurs who could guide me. There was a big support network for entrepreneurs, and amazing resources and support from the school itself and from my classmates.

Stacy: That’s what makes it different from just reading a business book. It’s the classroom discussion, the conversations over coffee afterward, the brainstorming, stopping in a professor’s office. It really is the human element that makes it such a special time.

And on entrepreneurship: people ask how you can learn entrepreneurship in business school. To me, being an entrepreneur early on means you’re doing everything. You need to know finance, accounting, strategy, marketing, HR. Going to business school and learning all of those buckets prepares you for the real deal.

Patrick: And people are willing to talk about your business over and over again. Your parents or your friends may not want to hear about it, but your classmates are usually passionate about business. They’re genuinely interested and want to help. You can find people who will talk through different problems with you again and again and help you solve the hard ones. It’s an amazing environment.

[10:15] Stacy: Agreed. So you graduate from Wharton, and you’ve built WSO over nearly 20 years into one of the largest online communities for finance and consulting in the world. What was your vision in those early years?

Patrick: Nothing close to what it is now. Initially, when I was launching WSO, I was really just trying to create a community, a place where people could learn about industries that were, at that stage, pretty opaque. If you went to the right schools or were part of the right club, it was a little easier to understand what private equity even was.

I didn’t know what private equity was coming out of Williams. And Williams isn’t some no-name school, it’s a liberal arts college, but I didn’t have accounting or finance courses. So I had more to learn. It was surprising to me that when I was in investment banking, I had no idea what my next step was. I thought, why am I so lost and floundering? There must be a lot of people like this. So I decided to start something simple, an online forum for bankers.

It was actually iBankingOasis for the first year and a half or so, before we changed the name. The angle we took was that, when you’re talking about investment banking, most people take themselves pretty seriously. So we did the opposite and had a little fun with it. We made our theme monkeys. There’s a famous book called Monkey Business, and back in the day they’d call the analysts monkeys. So we said, let’s make it fun, let’s gamify it.

We put bananas in the forums. Every time people contributed, they earned points, they collected bananas, and they could move up the rankings from monkey to chimp to, eventually, King Kong. It can be a stuffy industry, and we wanted to go against that and make it more entertaining.

We knew a lot of college students would come on, because that’s typically where they’re trying to figure out what they’ll be asked in interviews, what the pay is really like, and which groups are actually good to go into. I think that approach was one of the reasons it did well, besides the timing.

Back in 2006, the iPhone had just come out. In terms of search, if you had a lot of discussions built around long-tail search, you could rank pretty easily. It’s very different from now, when it’s flooded. Forums that were well optimized could get good traffic to a random thread the community created. It was mostly user-generated content, and it built steadily over the first few years.

Stacy: It’s amazing how much things have changed.

Patrick: Yes, a lot.

[13:18] Stacy: A lot of our listeners are actively trying to break into these roles. I’d love for you to share about the Wall Street Oasis Academy. What gaps are you seeing in traditional undergrad or grad career services that your program solves?

Patrick: WSO Academy is our most intensive program. It’s a 12-week boot camp focused on placing students into elite careers like management consulting, investment banking, and private equity.

For our MBA students, we like to see them join before they get on campus, because once you’re on campus, recruiting is so accelerated. You’re in coffee chats and cocktail hours by September. First and final rounds are done in January, and it’s typically all wrapped up by February of your first year.

So MBAs go in thinking they’ll have time to explore, and then it’s very difficult if they wake up in October or November and decide they want to do banking, especially if they don’t have pre-MBA finance experience and need to catch up on accounting, LBO math, and the technicals. They may also not have built out their network yet.

What our program does is streamline the whole process. There’s the training on the technicals, but more importantly, there’s the story: making sure whatever they did pre-MBA matches and tells something compelling and authentic about why they want to go specifically where they want to go. There’s a lot of one-on-one work with our mentors to make sure their answers have that authenticity and personalization and really resonate.

We stress-test it in mock interviews and score them across a bunch of subcategories, so they know that at a given level their odds of an offer are X, or that they’re at a certain percentile relative to other MBAs. The program closes a gap, largely for career switchers. People in corporate finance or consulting trying to get into banking, or vice versa, can accelerate their preparation for the entire recruiting process.

It’s intense, but it helps move the needle and makes sure everything is blocked and tackled before the timing that matters. The other thing about MBA recruiting for these top roles is that once you’re on campus, schools typically don’t like you networking outside the official windows. They’ll sometimes tell you not to. So there’s a window before you get on campus where you can do it, and do it with a bit of naivety: I’m just trying to explore and learn.

If you get 30 or 40 calls done before you even get on campus, at the top MBB firms and the top banks and elite boutiques, you’re at a huge advantage. Once the on-campus cocktail hours happen, you’ve already met a few people, and you’re more likely to get pulled through to the first round because you made that effort in the spring and summer prior.

That’s the program, but more importantly, it’s about the timing. It doesn’t mean that if you don’t land an on-cycle summer associate role, life is over. We’ve had second-year MBAs and even post-MBAs come in and still make the transition. But that window is when it’s widest, so you want to be ready for it.

Stacy: It’s such a rigorous, intense process that I don’t see how anyone gets through without crazy amounts of prep. It’s a lot.

Patrick: It’s not that the schools don’t have great resources. When I was there, I’d see people trying to break into McKinsey locked into rooms in Huntsman doing case after case after case. That’s what it takes. It’s more a question of the relationships you build before the process, which plant seeds that increase your odds of getting first rounds in the first place.

[17:39] When you think about getting any job, it’s really two problems: getting in the room first, and then converting. Depending on what school you go to and what your connections are like, sometimes the harder problem is that first step, just getting enough first rounds. Other times you’re getting a lot of first rounds, but for whatever reason something isn’t resonating.

Your technicals are a little above average but not exceptional. Your answers are good but not as good as the other candidates’. So you want to quickly diagnose where you’re going to struggle. Sometimes it’s a struggle at each stage and you need to improve at both. Sometimes you’re an amazing interviewer, ready to go, but you’re just not getting enough first rounds.

Stacy: That makes sense. If you go to HBS, maybe it’s easier to get your foot in the door for the first round, but then your competition within your class is so intense. That’s an interesting way to put it.

Patrick: One thing we see with MBAs in particular is that the bar for behavioral interviews is so high. With undergrads, if the behavioral answers are above average and come across well, they can sometimes still get an offer. For MBAs, you have to be incredibly polished, because you’re five or seven years out of school and the expectation is so much higher. Your competition speaks so much better. They’ve done speech, they’ve done debate. It’s just a higher bar.

[19:23] Stacy: I’ve seen with my own children that undergrad recruiting into finance has changed so much. How has banking and consulting recruiting changed over the last few years, in terms of the interview process and the barriers to entry? How has it evolved?

Patrick: There are several trends. The first and most obvious is the acceleration of the timelines. Right now, banking and consulting recruiting are both accelerated, but banking is even earlier, and this is for the US. By sophomore year, in September or October, it’s pretty expected that networking will start. RBC opened up applications sophomore year in September, and a bunch of other firms started opening in December of sophomore year.

So before you’re even done with your first semester of sophomore year, applications are open at a handful of banks. By January 1st, they all open. Offers are going out early to mid-January, and by the end of February, call it 70 to 80% of the process is done. By the end of March, it’s 95% done. It’s very early.

Stacy: And that’s for two summers ahead.

Patrick: Exactly. That’s an internship 18 months into the future. It’s not even a full-time job. This is an internship.

Stacy: So at the point when you’re supposed to be in college exploring, maybe thinking you want to be a history professor.

Patrick: It’s really unfortunate. I don’t like it at all. I wish we had more time, because then kids could come in early junior year and it wouldn’t be too late. The window wouldn’t have shut so much, and it wouldn’t be such a disadvantage. All the early acceleration does is help the kids who were told earlier. It pre-selects the kids who heard about it sooner, who had family or friends, or friends of friends, in it. It’s unfortunate, but it’s the reality.

Private equity recruiting has gotten even more insane. By senior year, if they know you have an IB job lined up, they’re interviewing you for a role more than two years away.

[21:28] Stacy: And what about for MBA students? How has that changed?

Patrick: For MBAs, it’s shifted earlier into the first year. The cocktail hours and networking events happen pretty early. You’ll see banks moving super days and first rounds into that first semester, or the end of it, rather than waiting until the new year, so they can do final rounds soon after the new year. So it’s shifted much closer to the new year. There’s also been some accelerated or diversity recruiting into the summer prior, but that’s lower volume.

Stacy: It’s like dirty rush.

Patrick: Exactly. It’s unfortunate. For the MBAs, I don’t feel quite as bad, no offense to them, because they’re typically a bit older and have had more time to research all of this. For the undergrads who are 18 or 19, it’s brutal. They’re expected to do all this networking and relationship building, which feels very unnatural at that age. They have to grow up pretty fast.

[22:48] What I always say to students who miss these windows is that in the moment it can feel devastating. If you wake up in your second year of your MBA and realize you wanted to do management consulting or banking, and that recruiting window has closed, it doesn’t mean you can’t do it. It just means the path may take a little longer. You may not get it right out of school.

Same for undergrads. Sometimes there are half-steps you can take to get closer, or to keep you in the same channel as that specific role. For example, say you’re at a semi-target, you have a 3.7 GPA, you’re a middle-of-the-road candidate, and you’re late, but suddenly you realize you really want this. You can still work your way into a deal advisory role at a Big Four firm, or a Deloitte, that keeps that window open.

If you become really good at networking, and rates finally get cut and deal volume picks up, and you’ve been talking to 70 people over the last three or four months who are in the industry, and you happen to be in the city, you’re probably going to get a lateral interview. If you’re ready, you can absolutely get it.

It feels devastating, especially to a sophomore who didn’t get it and sees all their friends posting on LinkedIn, thanking everyone for their support because they did. It can feel really devastating for someone young. But I always say careers are long, and habits are what matter long term.

If you develop the right habits at 19 or 20, networking when you don’t need anything, getting really good at building relationships and forgetting about the near-term job, then the reality is this: if you’re good at your job, if you’re a hard worker, if you’re kind to people, if you’re good at building relationships, you’ll absolutely start getting promoted and start being able to lateral or transition into other roles. That’s what matters long term for your trajectory.

So I try to calm students who are panicking. This is such a long road. We teach them the habits that matter and open their eyes to what’s possible if they put in the work day in and day out and stay consistent.

[25:19] Stacy: And that networking without wanting anything is a lot of what B-school is about. You’re meeting this incredible pool of people, and you don’t know where they’ll end up or what they’ll be doing, but you’re forming great relationships. Okay, rewind for a minute. A 3.7 in college is middle of the road?

Patrick: It depends on grade inflation at whatever school you’re at. If you’re at Princeton or Cornell, no, you’re doing amazing. But if you’re at a school where that’s the average, and you’re trying to get to these elite roles, then a 3.6 or 3.7 is still good, but it’s not going to set you apart.

My point was that recruiting itself, and networking especially, can feel super transactional. These students know they have to get a certain number of calls to get a certain number of first-round interviews to have a chance. Or they’re at the MBA level, going to cocktail hours and schmoozing, and it’s stressful. How do I dress? What do I ask them? How should I behave? All of that is fine, and you want to play the game as best you can to get the offer.

But really, the skill of building relationships and making someone like you, outside of the crazy context of a recruiting cycle, is the skill set that matters long term. Those soft skills are hard to teach. So we do our best. We have networking boot camps, foundational and advanced, and we score people on authenticity, not just delivery. It’ll hurt their score if they sound like a robot who’s memorized all their answers.

Stacy: Sounds like an amazing program. A huge percentage of our audience is a great fit for the Academy. They want to use the MBA to pivot into finance from a non-traditional background. So you’re saying that pivot is viable.

Patrick: Absolutely. People leverage the MBA for it all the time.

[27:29] Stacy: What’s a realistic timeline for these people?

Patrick: Ideally, you’re prepping before you get on campus. If you start prepping in September, it doesn’t mean you can’t catch up, but the further it goes, the harder it gets. If you’re going into coffee chats and cocktail hours in September or October and you haven’t started working on your technicals or done any networking, it’s going to be very difficult to compete, especially if you’re a pivot without any finance background.

Stacy: So we’re in the middle of July right now. What should they be doing today, right after they hear this podcast?

Patrick: Financial modeling training, right out of the gate. Make sure you know how to link the three statements. Know your accounting, know your LBO modeling, understand valuation and accounting interview questions. Start building that foundation and that technical knowledge now, because you don’t want to have to cram it when interviews start.

Second, before you get on campus, where they try to lock you down, start talking to people in the industry. What we do with our students is have them send out about 100 connection requests every single week. That turns into 20 to 30 new connections.

Stacy: And do you find those on LinkedIn?

Patrick: LinkedIn, yes. Just search for people who went to the MBA you’re going to and reach out. “Hey, I’m headed to Wharton,” or Darden, or Columbia, wherever you’re going. “I’d love to pick your brain. I’ve never done this. I saw you ended up in investment banking or private equity, and I’d love to have a 10-minute chat.”

[29:14] Stacy: So 100 outbound requests. How many calls will that turn into?

Patrick: It looks like this. About 100 new connection requests leads to about 20 to 30 new connections, which leads to about three to five phone calls.

Stacy: Which is so great to hear, because someone might send out three, have no one reply, and give up. You have to send out 100.

Patrick: And those numbers are with follow-ups. That’s not people just hopping on the phone with you. For MBAs it’s actually a little higher, closer to a 30 to 40% acceptance rate if you say you’re going to that MBA. Then about 10 to 15% of that group will get on a call. It’s a bit better because you’re more professional and not as green as an undergrad. Those other numbers skew more toward undergrads. But the point is, you’re still getting rejected about 90% of the time.

Stacy: So it’s good to know that going in and get used to it.

Patrick: That’s life, and it’s still super valuable. Even if you only get on 15 or 20 calls before you get on campus, I can almost guarantee one of them will pay off big when recruiting starts, especially if you make a good impression and ask good questions.

[30:40] Stacy: Love it. So looking back, nearly 20 years post-Wharton, how would you say the degree has impacted you over the years, and even now? Career, personal, everything.

Patrick: In terms of the way I look at problems, and at business models and how to solve things, it absolutely changed my entire framework. While I was on campus, it provided a tremendous amount of near-term value, helping the business accelerate to the point where I knew I didn’t have to go recruit and could do this full time. Right before my first year, on purpose, I did not recruit, to force myself to really hone in and see if I could do it. By the end of my first year, I said, I’m good. I’m at a stage where I don’t even have to go back.

Stacy: So you didn’t do a summer internship?

Patrick: I didn’t. I worked on the business 100%. By the end of that summer, I knew I was going to be okay. When I graduated, I was able to move to Argentina for a year and travel with my remote business. It was an unbelievable opportunity to have that freedom.

So it gave me a lot of near-term value, but the long-term value was really the frameworks: how to think through problems and look at a business through different lenses. Even though there were a lot of missed opportunities and mistakes along the way, it let me continually tweak and iterate, to the point where I launched the mentor service in early 2010, then interview courses, then financial modeling training, and eventually the Academy. None of that would have happened without the MBA and that framework for how to look at different things.

And some of my classmates did amazing things. Warby Parker, Harry’s. I was sitting next to these incredible people. I feel very lucky.

Stacy: I go back to my business school reunions and I’m amazed at how well the admissions committee really nailed it and put together an incredible class. People are doing so well. It works. They pick great people, put them into this environment of learning and connecting, and it turns out.

[33:25] Patrick: And Stacy, I think the decision of MBA or not is really interesting, because a lot of finance people, investment bankers especially, will look at it on a pure opportunity-cost basis, because they’re making so much outside. It’s a difficult decision. There’s a famous user on WSO called CompBanker, one of the top users of all time, with a lot of silver bananas and very knowledgeable. He was anti-MBA for a long time, then ended up going and getting his MBA, and he said it was the right decision because there was a lot of value that’s very hard to quantify on paper. It’s paid off huge for him.

It’s hard to quantify, not just the relationships and the experience of being there for two years, but the mental frameworks and the way you start looking at things differently, and the perspectives you get in the classroom from people from all different regions and all different careers. It’s invaluable.

Stacy: You said at the beginning that the MBA raises the floor. I think that’s true. Someone pre-MBA might think, I’m making this much now, and when I graduate I’ll make this much, so it doesn’t pay off. But what you don’t realize is that you get into that ecosystem, and what you thought you were going to do completely explodes and grows.

Patrick: And it changes. You didn’t realize it, but maybe you thought you were going to do investment banking, and you only do that for two years, and then you go work for a family office you wouldn’t have even known existed, or known how to meet those people. There are so many niche sub-careers and semi-entrepreneurial paths you don’t even know about, connections to investors you wouldn’t have had. It’s hard to know going in what it’s going to do for you even a few years out.

We see this with career changes. People have a plan in their mind, I’m going to get this X, Y, or Z return, and sometimes it changes. Sometimes the return comes massively later, seven years after the MBA, and it changes their tune. So I’m a big believer. It’s been great for me. Wharton supported me at an extraordinary level while I was there, and the alumni cohort is still close. We still have a WhatsApp chat with all of Cohort L. It’s great to still hear from everybody.

Stacy: Very cool. Well, Patrick, thank you so much for joining me. To our listeners, if you’re targeting an elite career in finance or consulting, make sure to check out Wall Street Oasis and their Academy. We’ll drop links in the show notes. And thank you for listening to B-Schooled.

Patrick: Thanks for having me, Stacy. Appreciate it.