Ray Shan
27 min read

Sales and Trading at Merrill to Software Engineer
Moving Up by Wall Street Oasis Podcast Transcript

Alex Grodnik, the host of the podcast “Moving Up” by Wall Street Oasis, and I chat about my colorful career path, and going after your life passion regardless of where you started.

The following is a transcript of the interview from the episode.


Alex Grodnik

Hi, I’m Alex Grodnik. And this is the Wall Street Oasis podcast. Today we’re speaking with Ray who started his career off in Sales and Trading before realizing that it wasn’t quite for him. So he left to build a career in tech. But don’t worry, he comes back to finance at the end of the story. Before we get into it, let me tell you about the courses that Wall Street Oasis has to help you prepare and crush your interviews from investment banking, to hedge funds, private equity, consulting. Their courses, have all the information you could ever need. Check them out. And make sure you say podcast is where you heard about them.

Ray, welcome to the podcast. Thanks so much for being here.

Ray Shan

Thank you for having me. Alex.

Alex

Yeah. So you’ve got a background where you grew up coding, but something inside of you told you that you wanted to do finance and you did that. And then you went to tech and back to finance. You’ve had this career that’s kind of cut through finance and tech, but let’s start the beginning. Let’s hear your background. Who Ray is.

Ray

Sure. So when I was growing up, I was really interested to make things both from a technical perspective, and from an artistic perspective. I’ve always studied art. I’ve always coded, I think, since I was about eight, I started, we’re just now trying to hack into games I used to play, trying to cheat on the games. I think that was a common theme for a lot of kids back in the days growing up in China. You get these bootleg games and then you use you try to hack into them. Through that I gained a lot of just casual technical skills. And then when I went to college, I was thinking about studying either computer graphics or some sort of engineering related discipline. The funny thing was my mother, at the time, she she told me, you know, you’re pretty smart kid, you probably be a pretty smart business person. But I doubt if you’ll ever be the smartest scientists ever. So I was like, okay, that kind of makes sense. I decided to study business. I studied finance and management. And if you study finance, I think one of the best exit opportunities is to go work in investment banking. So I was looking at investment banking and management consulting and I decided that I was better at Excel than PowerPoint. And I went into investment banking.

Alex

Got it. So you grew up in China, but you came to America for school or or before that?

Ray

That’s right. I grew up near Hong Kong and Shenzhen, China. I came to the US when I was 13 with my family. It wasn’t exactly my choice. But I think it turned out to be pretty good.

Alex

That’s interesting. So why’d your family move here?

Ray

It’s more because of my father’s work. He worked for CSX, the train company.

Alex

Right, China Southern.

Ray

No, CSX, the American train company. He used to go around the world to buy shipping containers. CSX had a big facility in Florida. So we moved to Florida.

Alex

Got it. Okay. So you go to school, your mom, you like coding, you kind of have this innate tech background, but your mom says, maybe you’d be a good businessman. So you decide, okay, I’ll study finance and trying to get a job in investment banking, and you graduated. How’d you do that?

Ray

That’s right. Frankly, it was really, really tough. I didn’t go to a target school. I went to University of Florida. I studied finance only at the undergraduate level. And after I got out, I was trying really hard to get into bulge bracket. I remember studying up on what investment banking is all about - the different roles you can have in investment banking, the different kinds of bulge bracket banks, or boutique banks that you can go to. I really wanted to go to a bulge bracket, I felt like I can learn the most by being in a really large company, and learning the best practices. That’s still the advice I give to new graduates nowadays. I think a lot of new graduates, they come out of school and they try to go to a really small company, maybe like a tech startup with 10 people. But I always recommend people to go to a larger company first, because you can learn a ton, and you can also meet a lot of people.

Alex

Yeah, it’s also more marketable to start at a big company with a name recognition. And then you can always go small, it’s not always easy to go from small to big.

Ray

That’s right. . . At the time, I think I was mainly interviewing at banks in the Southeast region. Maybe tier two banks like SunTrust Robinson Humphrey. I remember I went to a few banks in the area. But I really wanted to go to New York. So I got pretty lucky when I was interviewing at SunTrust I met someone. Actually ended up dating her for a while. Her sister worked at Merrill. That’s how I was able to get a referral into Merrill. At the time, the only available opportunity for me was to be in Sales and Trading, to working on the fixed income desk. And I decided, hey, you know, that sounds interesting. I read Liar’s Poker. I really liked it. Let’s give you a shot. So that’s how I ended up Merrill.

Alex

So then you’re working Sales and Trading. How’d you find that?

Ray

It’s very interesting. So I worked on a fixed income desk. And we dealt mainly with money market funds. At the time, Merrill had 56 money market funds we traded mainly for institutional investors. A lot of it is about really understanding the macro economic environment and being able to advise the clients on what to do. A lot of what you hear about the differences between the equity side of the house and the fixed income side of the house is fairly true. I think the equity side is more exciting. You get more actions. Whereas on the fixed income side, the volume is a lot bigger, the transactions are a lot bigger. It’s a very different field versus the equity side of things. You end up doing a different kind of event driven research. You end up talking to a different kind of people. Also, our desk was 24 / 7. I dealt a lot with the folks in Singapore, in London. We had to man our desk 24 / 7, unlike if you’re on the equity desk. You work there basically doing the opening hours. It’s very different. I was at Merrill for almost 2 years. Another interesting thing about my experience there is I was right there around the time Merrill Lynch sold Merrill Lynch Investment Managers to BlackRock. A lot of what I worked on was actually the transition of the funds to BlackRock. I worked a lot with the BlackRock team in New Jersey. Because of that, my group was dissolved, and I was looking for something else.

Alex

This is an impressive move you made. You went to a non-target school. You got a job in Sales and Trading at a great investment bank. You must have been feeling pretty good about yourself.

Ray

I definitely enjoyed the experience. I learned a ton. I think the most I got out of the experience was dealing with people. At the time I was thinking about how should I prepare. How can I be the best trader I can ever be. I need the best Excel skills. Can I use Excel without a mouse? What ended up being was… it’s really about relationships. It’s really about talking to people, making sure that people have faith in you, people trust what you say, and what you can do, and make sure you follow through on your promises. The relationship part was probably my biggest takeaway. But at the same time, I think I enjoy the job. But I didn’t necessarily enjoy being in Sales and Trading, because of my hobby. I wrote code, I really enjoyed it. I didn’t feel like I was really building anything meaningful. And I wanted to leverage more my hobby. So I decided to leave the group after the transition to BlackRock and look for something a little different.

Alex

Okay, and what you find.

Ray

So I was looking for something in New York. But I got a call from a headhunter who worked for HSBC, and I found a consumer finance job working for HSBC’s credit card business in Minneapolis, Minnesota. That was quite an interesting time for HSBC, because HSBC as we know, it doesn’t have a huge presence in the US. But on the consumer lending side, or specifically the credit card business, around the 2007 to 2009 time frame, it was actually the largest non-prime credit card lender in the US through a number of acquisitions. So it purchased a company called Metris based in Minneapolis, which is why it had a huge presence in the Minneapolis area. I thought it was interesting because it was a strategy and analytics role. I knew that analytics was going to be more and more technical. I knew that Excel is not exactly going to scale if you have to analyze consumer level data for 300 million people. I thought that I could get into analytics, and that’s my path towards the technical side of things. And when you work on B2C data, you really have to understand the full analytics stack. From data ingestion from vendors to the ETF pipelines, how do you pipe data into a data warehouse, to how to warehouse data correctly and efficiently to what kind of business intelligence tools or query tools to pull data out of your data warehouse and analyze it effectively. All the way to how to visualize data to tell the story with your insights. This whole stack is quite technical, especially for B2C data. Throughout number of analytics roles, my instinct at that time turned out to be correct. It got me really, really technical. It got me a lot of skills working with databases, working with various scripting languages, like SQL, Python, so I think it was a pretty good move.

Alex

Have you ever even been to Minnesota before you got the job?

Ray

No, I have not. At the time I was really young. I was around 20 ~ 21 at a time when I left Merrill. I think at the time I was just thinking I was single, I don’t have any baggage. I love New York, but I wanted to try something different. A different environment, and a different industry. Not a different industry in this case, but a very different part of the same industry. I was told by a number of friends, “Oh god you do not want to move to Minnesota. Why would you ever do that? Especially given you grew up in Shenzhen and Florida.” I went anyway because I thought I was young and I go where the job is. It was a really nice job, and I loved the team there. I was in Minnesota for almost 6 years. It turned out to be really really great. The Minneapolis - St. Paul Twin Cities area is a really nice place to live, especially in the summer.

Alex

My dad is from Minneapolis. I’ve spent a lot of time there. The summer it’s great the lakes and it’s beautiful. You know, in the winter. It’s a different story. It’s pretty cool. Yeah,

Ray

It definitely is. The main problem I have with it is the length of the winter. It’s like five, six months. You can have a blizzard in May, which is a fairly rare. I had the pretty nice at the time, I had underground heated parking where I lived, I also had underground heated parking where I worked. If I wanted to I could actually stay in my car and inside all day without ever going outside, so I thought that was okay.

Alex

Nice. Okay so you’re there six years, building a career, building a life. Then what happened?

Ray

I met my wife there. She was going to University of Minnesota at the time. She decided to go to Berkeley for her grad school. I had a number of different jobs there. I also did my own start-up in the Minneapolis area. I was thinking about what I want do next. I thought, okay now that I’m more technical with my analytics background, I want to get closer to software, to do professional software engineering. And the best place to be is the San Francisco Bay Area. I think it’s similar to when I first came out of the school, where is the best place to be for finance? That is New York City. Because of my wife, and because I wanted to be closer to software, I moved out to the San Francisco Bay Area.

Alex

Great, so you move from Minnesota. Now you’re in San Francisco. Are were you married at this time or were you still dating?

Ray

It’s around the time I moved here when we got married, so it’s been almost five years since we got married.

Alex

I think a trend is starting to develop here. You’re willing to go where the opportunities are. You’re willing to move around and just make the best of something, and I think that’s a good lesson. A lot of people think, “oh, I need to be in New York. I was from New York area, my family’s here, my friends are there, that’s the center of the finance world, and I’m not willing to go anyway else”. Whereas you work in New York, you went to Minnesota, you went to San Francisco, you followed where the opportunities are. Is that how you look at it?

Ray

Yes, I do agree. Another key takeaways is perhaps think about what you really enjoy doing, because I think a lot of folks want to go into investment banking and finance because it’s a very lucrative job. It’s a very high profile role. But after a while, I think money will only take you so far. At least for me personally, I always think about what I really enjoy doing. I love building things, and love seeing the joy of people using my creations and being delighted. I can do that more effectively by either writing software or being a product manager than being an analyst. I just enjoy that more. And the creative process was more meaningful for me than other aspects of my career, so I pursued that. Like you said, I also went where opportunities are. I can tell folks a bit about why the San Francisco Bay area is really, really good for startups and software. One specific example is, after I came here, I went to a ton of meet-ups. I lived in San Francisco, in the city. Every single night there will be some sort of meet-up, most technology-oriented. Perhaps about some open-source library, or about how Uber does data science, or how Square does fraud detection using artificial intelligence. You can go to these tech talks, or meet-ups. They’re usually hosted at some mid-to–large company, for example, Airbnb. You go there and they feed you. Their kitchen cooks for you, so you get free food. You can eat at meet-ups every single night of The Week. You meet a ton of mine people, and you don’t really have that anywhere else. I went to a few tech meet-ups in New York. There are certainly a lot there, but you cannot really compare to the breath and depth of what we have in the San Francisco Bay Area. I think a lot of that has to do with the fact that a lot of startups are based here and a lot of technologies, they grew up in the San Francisco Bay Area. If you think about some of the top open-source software packages on GitHub, a lot of them are created by folks who live in the San Francisco Bay Area. That really helps a lot if you want to get closer to software.

Alex

Absolutely. You get to San Fransisco, you’re about to get married, you have no job. You’ve identified, which is a huge step, that you would like to build things. So you’re starting to check things off your list of what you wanna do, things you don’t wanna do. What happens, how do you find your next gig?

Ray

I really wanted a job as a professional software engineer. I’ve written code for a long time, and I’ve contributed to some of the largest open-source software packages in the world. But I knew if I worked on a quote-on-quote “professional” software engineering team, it will be a very different learning experience than me hacking away on a open-source project online, with folks from all around the world. In order to do that, my strategy was to go to meet-ups and meet as many people as possible. One of the other themes I have about building my career path over the past 12 years or so is: as you get more senior, more experienced, the kind of roles that really are promising for you will eventually turn out to be the ones through your connections. Nowadays, when I’m looking for jobs, I no longer apply online. I no longer look for jobs on LinkedIn and what not. I always check with my network to see, okay, I want to work at, say Airbnb, who do I know or who I know who knows someone who can introduce me to someone at Airbnb. I think that both gets you into the door more easily, and they can also tell you about their experience there, because sometimes from the outside, a company may look really promising, but from the inside there are a number of problems that you may want to avoid. So I wanted to build this network with the software engineering crowd here. I went to a hackathon put on by Google and I met a guy there. His name is Charles. Charles turn out to be one of the original engineers who built the entire iTunes stack for Apple back in the ’90s after Apple bought SoundJam. He is a very senior engineer and he is a very, very good technical architect. I work with him in the Hackathon. I knew I wanted to work with him at some point, so I stayed in touch with him over two years. I kept asking him, “what are you working on? I’d love to work with you on something. Let me know what I can do.” Eventually, he went to a startup called Montage Studio, which is a startup founded by a team of folks coming out of Apple and NeXT. He went there and he’s like, “hey, I’m here, I’m working on some cool stuff, you should come.” I went there, and that was my very first software engineer gig.

Alex

That’s really cool. Can you tell people exactly how you cultivated that relationship with him. You met him at this event. Where did it go over the next, however long it took you to get this job? You have coffee once a month, you send an email of interesting articles. How do you keep that relationship going?

Ray

I try to do both. Charles actually lived in Texas. He was doing consulting gigs at the time, so he would travel back and forth. I would just ping him, I would say, okay, where are you in town next? And I knew he loved to go to meet-ups too, so I would say, okay, let’s go to this meet-up together. We would go, and we would listen to some tech talk, we would chat a bit, and then I would show him the open-source software projects I was working on. At the time I was building this Bitcoin arbitrage dashboard kind of thing. I showed him and he was like, “Wow that’s really cool. I cannot believe you were able to build this and you don’t have any software engineering experience.” And then he said, “Look, I’m pretty sure that if you really wanted to find a job as a software engineer, you can very easily find one.” He gave me a lot of advice. I also got the sense it’s not just that I wanted to work with him, I got the sense that he also wanted to work with me on some level as maybe a more junior dev. I think that was very helpful, because you don’t really want to push someone who may not have the time or energy or the interest to network with you or help. You definitely wanna test the waters. Once you have some indication that you can have a very fulfilling relationship that’s win-win on both ends, you should definitely go for it.

Alex

You were able to show him that you could provide value, and that was a big step forward.

Ray

That’s right.

Alex

Okay so you start working at this startup company, software engineer, how does that go?

Ray

It’s very, very hard. When you hack away on things on your own, you don’t really think about some of the things that are required in a professional software engineering environment, where you have to ship code to production. Things like, you have tests for your code, or you should have some sort of continuous deployment environment, or you have some sort of feedback loop with your customers to integrate new features. There are a lot of things that I didn’t know, working on open source software projects, and I found out and learned. I think the most challenging thing for me was working as a framework engineer. That means it’s quite low-level. We worked on a web application framework. Imagine if you build Gmail. You might be able to say, “Okay I want a button here. If I click on the button, I can compose a new email.” But what you don’t think about is, how does that button show up? What kind of framework does the email application use in order to build buttons and forms and windows and what-not. It’s more low level. We are basically building tools for other software engineers to build applications on top of. I think the requirement and the technical know-how there is a lot more challenging than building application code, like if you’re building just an app. The learning curve was extremely steep for me. And frankly, I had a very tough time in the beginning. Eventually it got easier, and I think working with a really senior team of folks was really helpful. They were able to teach me a lot, and I’m forever grateful for them giving me a chance to be a professional software engineer and for everything they’ve taught me.

Alex

As you’re going through this hardship so you have to be thinking in 15 years ago, maybe my mom was right.

Ray

I think it’s interesting to also think about what software engineering means. It’s similar to investment banking. It’s not actually clear if someone says I want to work in investment banking. There are at least like five major areas in investment banking you can work in. It’s the same with software engineering. You can be a front-end engineer. You can be a back-end engineer. You can be a data scientist who mainly focuses on writing algorithms. You can work on high performance computing, where you had to deal a lot with the bare metal hardware. My specialty is UI design and implementation. I think that has to do with my interest for the design and art side of things and my experience there. Also having to work with a team of folks designers, engineers, who came out of Apple and NeXT was really helpful. Even though we were mainly all engineers, we sort of all played dual roles as both designers and engineers. When we worked on client projects, we basically do the whole scope. We don’t just take the designing specs from a designer and then implement it. We’ll try to help the client on basically the full scope of the project. I tried to focus on a specific area I knew I would be good at, and I knew I had a lot of interest in learning more about. That’s actually the advice I give a lot of younger engineers nowadays. A lot of people who go to these coding boot camps, and they try to teach you to become what’s called a full-stack engineer, sort of like a jack of all trades if you will. But I think it’s very difficult to be a full-stack engineer. Just a very small part of software engineering is difficult enough. Also the context switch between working on the UI, versus working on the back-end, versus working on some networking issues, it’s very challenging. So I always recommend people to focus on one area. That’s what I did, and I feel like I was able to get deep enough on just the UI design and engineering part. Eventually I was able to lead a team with my skills develop in the area.

Alex

Very cool. So you start your career off in Sales and Trading. You realize “I like building things”, but there’s still something inside you that likes finance. You start to work in these engineering jobs. Bring it full-circle. How do you get to where you are today, how do you bring finance back into your life?

Ray

Sure. So the company I was at Montage Studio, it got acquired by a back-and Company. And I knew that I didn’t really want to work on back-end technology. So I was looking for my next opportunity and I was thinking okay since I worked on the business side of things, I worked somewhat in design and also in software engineering. So I’ve done these three pieces that the natural intersection of these three pieces is product management. So I was trying to decide whether I should be a product manager then, or be a problem manager in five years. Maybe take another software engineering job, which will be like a natural thing to do since I was already one. But then five years later transition into a product manager role. And I wanted to transition eventually because even though I’m able to get a job as a software engineer. I’m not - after looking at my background, I don’t think I’m that competitive versus someone maybe with a master’s degrees coming out of CMU or Stanford in computer science. So I was like, okay why would I compete with those folks? Right? Like what do I have that special that businesses can utilize that those folks don’t have. And it’s my business background. So I decided to go into product management and I decided to do it after my company got acquired instead of doing it maybe in five years. So I went to a startup called Yewno, which builds a search engine, an academic search engine, to compete with Google Scholar. I was their first as a product manager and then as the Director of Product Management, helping them to build both the UI engineering team, the product design team, and the product management team. I was there for awhile. And then I was able to connect with my contact at Andreessen Horowitz. I was telling her, okay, I liked working on a search engine, but it is an academic search engine mainly in the education field, and I don’t feel like it’s really utilizing my background. I wanted to get closer towards what I knew. There are two areas to industries that I know fairly well. One is finance, and the other one is eCommerce. So I told her about my story, I told her about what I might be looking for my next role. And she said hey, we have this portfolio company called The Long-Term Stock Exchange. It’s in finance. They’re trying to innovate from a software perspective and they might be looking for product managers. So she introduced me. And that’s how I ended up meeting the team at The Long-Term Stock Exchange. And that’s how I ended up here.

Alex

That’s great how your network came through again. So tell us what’s Long-Term Stock Exchange. What do they do? What do you do?

Ray

Sure. So The Long-Term Stock Exchange - what we’re trying to do is we’re trying to build a new stock exchange with a focus on long-term value creation. And our exchange will be listing-focused instead of trading-focused. So when we get approved by the SEC, we will be mainly going head-to-head against the New York Stock Exchange and NASDAQ to compete for listings.

Alex

What does that mean? What does that mean? Like the new listings or what?

Ray

We can do a number of things. We can do new listings or can do dual listings. Existing public companies can also dual-list both on New York Stock Exchange and on our exchange.

Alex

I see.

Ray

Yeah. But at the same time we will also do everything else that the other exchanges do. We also do trading. We are building also the first purely cloud-based exchange. A lot of the exchanges nowadays, they make a lot of money on having a server farm and renting out colo space. We don’t want to focus on the trading side of things. We would do it, but our main differentiation is what we offer to companies who list with us and our listing standards.

Alex

Got it. So you’re product manager there.

Ray

That’s right.

Alex

And who’s the CEO of this company?

Ray

We are headed by Eric Ries. Eric Ries, he wrote a book called The Lean Startup. Some of you may have heard of the book. The book discusses a number of ways to really - build a Lean Startup. If you’ve heard of the term minimal viable product, MVP, or pivot, or innovation accounting, he helped to popularize some of these concepts in the book. He actually just had a new book come out, a follow-up to The Lean Startup, called The Startup Way. The books are not just about how to be a start-up and be lean, but it’s also about how to build a lean startup practice within a much larger company. He also talks about how he helps companies like GE to build a lean innovation department that can quickly iterate on new products and get feedback from customers.

Alex

That’s great. That must be a cool guy to work for. How big is the team?

Ray

So we are right now about 30 people including our employees and our advisors. Just another note about Eric Ries: he actually had this idea to build a long-term stock exchange for long time. For those of you who read the book, if you flip to the very last page of The Lean Startup, he actually talks about The Long-Term Stock Exchange. He had this idea, and he’s like, hey, if anyone would build it, I would love to help. But nobody did, so he decided to build it himself.

Alex

That’s that’s great. That’s like the entrepreneurial mindset. So Ray where do you go from here?

Ray

I think - I really wanted to find a happy home for myself if you will. Something which blends my background and also help me to build things that’s meaningful and also fun. I left finance because I didn’t feel like I was really building anything too meaningful. But now I’m sort of back if you will. I’m actually building something meaningful in a field that I really know well. Hopefully we can do a great job. Right now. We’re going through the SEC approval process. Once we are done with that we can help list companies. We can help bring startups to IPO to offer liquidity to startup employees. We can also offer long-term value creation and align the management team and investors. We have a number of things lined up which we really believe will help the whole Equity Capital Market environment. And if we are successful I can see myself being here for a long time. Even though I’ve done quite a number of roles in the past, I’ve always wanted to sort of be somewhere and really help to drive the business, to build it from the ground up, and to help it grow. So if we’re successful I can see myself being here for quite a while.

Alex

Right. I hope you are. I wish you luck on that journey. You’ve done, you know, what you’ve done is inspiring. You started off, hustled your way into a finance job. You realized, I think one of like the big pieces of what you did is you realized what you want to do and you march your way along that path to make that happen for yourself. And now you’ve kind of combined your two worlds of tech and finance, but it’s not - the journey is not a straight line. Zigs and zags and it’s up and down. You moved across the country and different places and you know, you basically just put opportunity in front of uncertainty. And I think that’s a great lesson. So I’ll let you leave it with you know, any last piece of advice you have for people trying to break in do the same, find what they’re you know, you call it a hobby. I call it a passion. But anything that you can leave listeners with would be awesome

Ray

Sure. So I’ve heard this advice over and over again in the Bay Area, which is, if you see a rocket ship you should strap yourself on the rocket without asking any questions. And I think that makes a lot of sense to a certain extent. I think first you have to identify what this rocket ship is, and hopefully it’s something with a huge growth potential, and it’s something that you’re passionate about that you would really enjoy doing. Because if you don’t, I think you’ll be burned out in a couple years. And really if you are able to identify something like this, you should try to get yourself in there whether it’s taking a step back in your career or taking a pay cut. If you can learn something new and that will help you going forward, don’t be afraid to take the opportunity.

Alex

That’s great. Ray, this was awesome. Your story was great. Thanks so much for talking.

Ray

Thanks for having me Alex.

Alex

Okay. Thanks for listening today. We’ll be back in two weeks with another episode. Until then, leave us a review on iTunes and send me an email: alex@wallstreetoasis.com. Thanks for listening.

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