Exclusive Interview: How the 21-year-old Wall Street Confessions founder created a must-read for the finance elite

Business of Business: To the uninitiated, how would you describe Wall Street Confessions? 

Ri: Wall Street Confessions is a community of over 112,000 finance professionals who share their stories and experiences of working in finance.

Where did this idea come from for you?

I was in college, I was recruiting for investment banking. And since I was young, it was kind of my dream job. Like, when I was 16, I picked up Investment Banking for Dummies, and I was like, "Oh my God, M&A deals are so cool! This is what I want to do with my life."

And then when I got into college, I have this scrappy mindset because I was going to a non-target [school that is not targeted by investment banking recruiters]. And I was emailing everywhere.  I went to Trinity in DC for about a year. And then I went to Marymount Manhattan College, where I double majored in finance and international studies. And but when I was at Trinity, which is such a non target. In financial services, they pick people from certain schools to recruit from. So like Harvard, Columbia, top tier schools are oftentimes where I've noticed investment bankers come from.

My school had a very high acceptance rate, it was a small woman's college. So I was in my dorm room, emailing anyone who's anyone at Goldman Sachs. I remember emailing someone's executive assistant, and being like, "Hey, investment banking is my dream job. I would love to talk to you about Goldman Sachs." That didn't work out.

"I thought there were deeply rooted problems in the industry no one was talking about."

And I was following a lot of financial-focused pages on Instagram, such as Not Your Father's Broker, Litquidity, many more. And as I was following them, I noticed a trend, that there was a lot of humor, which I appreciated. I felt like I was getting a look into some of what the industry was. But there was no one who was really starting the conversation early on...a lot of people were making story posts, and they're posting here and there about their experiences in finance. But when I was recruiting as a young woman of color, I thought that there were deeply rooted problems in the industry that no one was talking about. And I decided to start an anonymous confessions page for people on Wall Street. And I was 19.

And that was how long ago?

Two and a half years. 

Wow. And where do these confessions come from? 

So my first three or four confessions — I had a lot of friends who were working in finance or had interned in finance, and I remember messaging them and being like, "Hey, I just started this thing meme page," like a financial meme page, which I wouldn't call it now. But back then, and I was like, "Can you just tell me like one or two things that happened to you while you were working on the Street?"

And they told me and very quickly, it picked up traction. And what I noticed was that women were sharing their stories, whether there were sharing #MeToo incidents, or just general things about gender and equity. And women really, were and continue to be the backbone of the page by being so vulnerable so consistently. 

So this is kind of giving an outlet you think?

Absolutely.

Interesting. So it started like two years ago. How big is it now? 

I have about 113,000 followers.

Wow. Can you give me an idea of the kind of how much the volume of the confessions is and what kinds of like email traffic you get, and so on? 

I would say I got a confession every other day now. When the page was really taking off, I would get five or six a day, and I couldn't keep up with them. And I remember when I started the page, one of my biggest things was to post twice a day, every day. But my schedule would burn anyone out, naturally. And I quickly learned that there were certain times I should post or certain things I should wait to comment on or to bring stories in about. So now I would say every other day someone says something.

And you have some some pretty big name followers, right?

Yes. Rich Handler from Jefferies is my biggest Instagram follower I think. And also on Twitter, I just love this story, Paris Hilton follows me because we were on the same Clubhouse talking about NFTs.

Wow, cool. So how, how does this kind of kind of float into what you're doing now? Like how did it drive opportunities for you? 

I'm very lucky. Most if not all of my work experience has been from Wall Street Confessions, and people DMing me asking what they should do with regards to content strategy. My current job, I work in business development out of financial media company called Bullish. The CEO was selling ads for a company and the Instagram page probably had, like 6,000 followers...One of my friends told me, "Oh, like I'm doing ads for this company, Direct message this person." And I remember, it was like, a gap. It was a month in the summer where it wasn't working. I was just kind of finding myself. 

"I look at Wall Street Confessions as something I've built and something I'm very proud of."

And I messaged the Bullish Instagram and I said, "Hi, are you selling ads by any chance? I have a lot of followers," or something along the lines of that. But then really, he was like, "Yes, we are selling and that's me." My second message, I said, "By the way, it looks like you need someone to, like, help with your Instagram," or "I would love to help out your Instagram." Brian Hanly, the CEO, and I got on the phone. We talked about it. I think within the week I was hired and I started working at Bullish.

Wow. So this really became your job, essentially. It sort of opened the door for you. 

Yes, in many ways. I'm very lucky to be able to message people and have my work really be on display when I do message them. Because I look at Wall Street Confessions as something I've built and something I'm very proud of. When I message people from that, from that account, they can see exactly what I've done so far.

Really interesting. So do you sometimes meet people in person that you have received confessions from? And what's that like? 

It's always quite surreal. I was at a party, I think in Williamsburg or Bushwick a few weeks ago, and I met someone, and he worked in private equity. And he just kind of really had a moment with me. And I had a moment with him where he was like, "This page means so much to me. And it means so much to my friends. And I'm so grateful that you do it. And you're really doing the right thing." And I got a little emotional. Because with everything going on lately with burnout, a lot of people are very upset naturally. And it just felt nice to meet someone who appreciated what I was doing.

"People are always surprised...They're always very surprised that I'm a woman. And I'm so young."

But aside from that, the first time I got recognized, I think I was like 20 and I was at P.J. Clarke's in Midtown with a friend. And someone kept looking at me. So naturally, I started looking at them. And finally after squinting his eyes, he was like, "Are you, are you Wall Street Confessions?" And I was like, "Yeah, yeah, that's me. Hey. And he was like, "I sent a confession to you about like, the computers not working at my bank." And I was like, "Oh my god. Hello." 

Are there things people find surprising about you? When they do meet you in person?

People are always surprised — well, not just when they meet me in person, but when they find out who I am. Whether it's through an interview, or through just looking at my Instagram and finding my personal [account]. They're always very surprised that I'm a woman. And I'm so young.

Yeah, it just doesn't fit the stereotype that they have, I guess. Yeah. Interesting. Where do you see Wall Street confessions going? Or where do you hope it's going?

There's so much more to come. And I'm very excited to continue to foster productive conversations and productive discourse and keep sharing people's stories for them.

Right right. So this is like this is your brand you have established this brand for yourself. We talk about Gen Z in branding and so on. Did that ever enter your mind? Like, "I need to make a brand for myself?"

Yes. And I had a few moments where I was like, "Is Wall Street Confessions my brand, or do I have a personal brand?" And I'm at this amazing point now, where I have my personal page, and I write a dating column weekly. I'm starting a book club. I built such a sense of community with women in New York. And I've created a degree of separation between Wall Street Confessions and my personal brand. But I do see it as my baby. I really love being the founder and I love what I do on Wall Street Confessions.

Do you think you have had an impact or change some of the conversation and investment banking around culture for women and minorities, and so on? 

I would definitely hope that I've had an impact. From the conversations I've had with people in real life, it does seem that a lot of my posts, do get people thinking at least on a granular level. If someone's been working for 90 hours a week, or 80 hours a week, and they see something on my page, and they don't feel so alone, I view that as impact in and of itself. Because that is what the page is meant for. 

And you've said before, you don't do any, any sort of research into these confessions, right? You just be post them as is like, how would you describe it? And how do you choose what to post? 

I do post them as is, with the exception of like one or two grammatical edits, which anyone does when they're posting something of that nature. But I think a lot of it is intuition. And if I do think that something is a little off, I'll throw it to one of my friends at a bank and be like, "Hey, what's your point of view on this?"  Because people have sent things that are like the plot lines to like The Big Short or Billions and other things. Sometimes I'm like, "Can this actually happen?" 

That makes sense. You want to be authentic.

Of course, as authentic as humanly possible without bothering the person who I know nothing about.

And this anonymity provides a sense of safety, I'm sure.

Everyone's protected, and the most due diligence I do into something, or rather the most fact checking, I would say is to make sure something's possible.

Yeah, that makes sense. Yes. So for other people who might be having ideas to become content creators or do anything like this, do you have any advice? 

Something I learned the hard way, and something to be cognizant of is if you're building a brand like this, be sure to maintain degrees of separation between your personal brand, and the brand that you're building. Keep your mission in mind.

"If you're doing something sensitive and delicate like this, continue to fight the good fight, no matter what people tell you to do."

And if you're doing something sensitive and delicate like this, continue to fight the good fight, no matter what people tell you to do. Because at the end of the day, sometimes I look at my comments section, and people are commenting, you know things about women, and how women are so sensitive. And I could delete those comments, or I could leave that and I could allow discourse to happen. And I never get discouraged anymore. Because I know I'm doing the right thing.

In terms of leaving the comments or deleting the comments? 

I leave the comments. And I leave them because I want all point of views to be heard Unless, of course, they're a danger to society, right. But I leave comments so people can educate other people and get different point of views. But sometimes in the past, I've seen comments like those and I felt discouraged because when they started, I was 19. And I really did not have that big of an understanding of the world. But now those comments make me want to post what I'm doing even more or like post even more confessions. Because comments that invalidate women's stories or stories of survivors can be extremely hurtful, and they can set people back. But I view them as something to push me to continue to do this. I know that even if I get flack, it's important to be the voice for people who don't necessarily think that they can come out and talk about what they're going through.