Show Notes:

When Jessica Leon was growing up in rural Idaho, she couldn’t imagine that one day she’d be working in New York City at Goldman Sachs. But fast forward to life post-college, and Jessica was doing just that. Everything seemed to be going great until a 5 billion dollar company-wide “mistake” led to her team becoming disbanded and getting laid off. As painful as this moment was for Jessica, she turned that moment into a catalyst for growth, and came out stronger on the other side. On today’s interview, Jessica talks about getting to MIT Sloan/Harvard Kennedy School and what it takes to break into venture capital – as a first generation, unapologetic BIPOC.

Links Mentioned in the Episode:

Seizing Every Opportunity

Venture Deals – “the Bible” of VC

Arlan Hamilton’s It’s About Damn Time

Breaking Into VC Resource Doc


Jessica Leon: But never give up. You need to be very persistent, ask to meet, be bold and reach out, like I think for like venture capital, you either know how to do diligence and know whether or not an investment is good, but the other part is just networking to either get new deal flow or also to get someone to invest in your fund. So, if you can really prove that you have those skills, you would be great in the venture capital setting.

Priscilla Esquivel-Weninger: Welcome to The Early Career Moves podcast, the show that highlights remarkable young professionals of color, killing it on their career journeys. I am your host Priscilla Esquivel-Weninger, proud Texas Latina, daughter of immigrants and lover of breakfast tacos. Meet me for a coffee chat every Friday as we dive into a special guest story and hear all about their challenges, milestones and lessons learned.

If you’re a young professional of color and you’re feeling lost in your career, or just need a dose of inspiration. You’re in the right place. Let’s get started.

Hey, everyone, welcome to episode 26 of season one of The Early Career Moves podcast. I’m so excited to introduce to you Jessica Leon. She’s today’s guest, and she is amazing. She talks about what it’s been like to be first generation Mexican American who was the first in her family to go to college and somehow was able to come across these amazing opportunities that landed her in New York City working at Goldman Sachs, and she talks about what it was like to go through a sudden layoff that had nothing to do with her, but had pretty big implications for her career, how she thought about what she really wanted, and I really think it’s a really great story that she tells about how to be resilient during times of immense challenge, especially when you’re financially responsible for not only yourself but your parents – you support them in some way and suddenly something like a layoff happens and you have to sort of figure out where to go next.

So, she talks about that amazing experience. I say amazing because it really sounded like it was a big catalyst for growth, and then lastly, she’ll talk about what it’s been like to discover venture capital as a career, what it means to work in VC, how she’s been able to break into the industry without having the experience of being an investment banker or a consultant, so she’ll go into depth about this and her interview. Currently, Jessica is an MBA and MPP candidate at MIT Sloan School of Management and also at Harvard Kennedy school at Harvard, so she’s making moves. She’s amazing, she’s such a cool, down to earth Mexicana, loved chatting with her, and I know you’re going to feel the same way too.

Okay, everyone. I’m so excited to have Jessica Leon on today’s episode. Welcome, Jessica.

Jessica: Hi, everyone. Thank you, Priscilla, for having me. I’m really excited to hear about your podcast and also to share my experience.

Priscilla: Of course. So, I would love to get started with just hearing a little bit about your own personal background before we get into your career story just so that we can get a sense of who you are and where you come from.

Jessica: Sure, as you said, my name is Jessica Leon. My parents, they are Mexican and my dad is from Durango and my mom is from Los Mochis, Sinaloa, and they immigrated early on in their lives to the United States, both legally and illegally, and I want to tell the story mostly because I feel that my story is a reflection of theirs and if it weren’t for them, I wouldn’t be here today.

So my dad started working in Arizona picking oranges and then was recruited to go to Idaho to go pick rocks from the fields. I, and as well as my siblings, were born and raised in Idaho and we always get questions as to why Idaho, how did you get there? And there’s a reason, is because of that, like my parents worked in the farms and there was a lot of opportunities for them to work there. Growing up, I went to the public high school available there. I didn’t really realize that there were applications and other fancier schools until I moved to New York City later on in my life. Otherwise, I just did as I was told and as the school progressed, I went to a high school in the area, and then from there, I decided that I wanted to. Look into other careers. So, I was actually interested in being a doctor. As a daughter of immigrants, you’re either a doctor or a lawyer. Those are the careers that they know and they they seem to value the most, and with that, I was like, yes, I’m going to go be a doctor. I was taking all of the medical classes, that included even getting my certified nursing assistant certificate to become a CNA and I was also looking, foreshadowing where you go and just look at the people’s jobs and I did that for an orthopedic surgeon and a chiropractor, and I realized that, I mean, I really enjoyed it. I wanted to be an orthopedic surgeon, so I was ready, but throughout that time, I was also very involved in the Finance Academy, Business Professionals of America, BPA, and DECA. I don’t remember what DECA stands for, but it was a business club in high school. I was very involved in that, but then came around the time that I had to apply for college. I didn’t know where to go and my parents didn’t know where to point me either, just because they knew the language, they didn’t really know how to speak it that well, but they didn’t know what was available for us. There was a community college across the street, so they were always just telling me to go there. My guidance counselor actually told me that I should go do makeup or hair because I did that well, and definitely, I respect those careers, but I felt that I was being stereotyped into fitting that mold because of being Latina in a predominantly White school. After that, I decided to push forward and another teacher said I had free lunch so I can take the ACT for free and ended up taking it and then going off to a Hispanic conference later on that year, where I was later introduced to the University of Idaho, which is about an eight hour drive from my hometown and there, thankfully I got a scholarship called CAMP, which stands for Campus Assistant Migrant Program which allowed me to go to school and also allowed my parents peace of mind for me to be sent there. So, I ended up going to the University of Idaho and again, I was doing pre-med and I decided to do business as well, and during my time there, thankfully secured a couple of internships during my sophomore year, and later on in my junior year, the first internship that I had was actually at the National Nuclear Security Administration in Los Alamos, New Mexico where I was working  in occupational medicine, again, because I wanted to be a doctor and also do business. I was looking at the operational efficiencies of the clinic available there, then my junior summer, I applied to this program called Sponsors for Education Opportunity, SEO. Now, I think they rebranded it called Seizing Every Opportunity, but it’s a program that, there’s different phases of it. I did the career one which allows underrepresented minorities to get into careers in finance and I ended up going to Goldman Sachs. I had no idea what Goldman Sachs was, I’ve never been to New York, I had no idea how to even, like, I’ve never been on a plane, so it was very interesting too to go there, and I told my friend, I was like, “Hey, I don’t know where to go, I have nowhere to stay, I don’t trust Craigslist.” That’s the only way, this is before Airbnb, it’s like, I don’t trust Craigslist. I can’t really rent an apartment in New York, and my friend said, “My cousin’s boyfriend’s sister lives there, let me talk to them and see if you can stay there in Queens.” Thankfully, they let me stay there and I ended up going to Queens, and it was a great experience overall being at Goldman. Later on, I did found an apartment closer to my work, but just being at Goldman and being in the city that was massive and just being in the city, coming from rural Idaho, literally, when I say rural Idaho, I mean like cows and farms and all these other things, and then going to the city, I was just amazed of the magnitude and also the people there. I realized that it was so dirty and gross. At first, I was like, where am I? I feel like I’m in a third world country just because it looks so dirty and dinky compared to the United States that I was accustomed to, but then as I mentioned, the people were amazing, the energy was just exhilarating, and I really enjoyed my internship there. I was working mostly in procurement and understanding vendor management and I, thankfully, was able to leverage it to a full-time position.

After that, I went back to Idaho, finished my year and came back, and moved to New York after graduating from the University of Idaho. I was at Goldman Sachs for about two years working in environment and social governance programs. This includes the supplier diversity and also buying renewable energy, but after that, unfortunately, my team was let go because they had to pay, like, a $5 billion fine due to the 2008 financial crisis. That was really hard for me because I was supporting my parents. They didn’t know that I had lost my job and I just felt I failed. It was really hard for me during that time, but I leveraged that as an opportunity to see where I wanted to go next and really make a deliberate choice of what I wanted to do. I think before that, I was just going with the flow as to what am I doing with my life, everything was just set up there, but this time, I had to choose, I had a choice. I now knew what business was. Before that, I didn’t know what business was, and now, after being in New York for two and a half years, I had a better understanding of what my career could take me. Go for it.

Priscilla: Yeah, so that seems like such a huge, almost like a crisis moment, right? Like, two years, it was after two years of working at Goldman Sachs that that happened?

Jessica: Yeah.

Priscilla: Yeah, and so what did you do in that month when you found out that they were letting your team go, did you reach out to anyone? How did that look like for you?

Jessica: I wish, it was a month where I had time to go. It was just like, I went to work one day and they were like, “Bye,” so I thankfully had a severance package, that’s another thing that I didn’t know about, and I was provided with a couple months of pay in addition to outsourcing services or services to place you at another job, and so I was able to leverage all of those benefits that they provided me, but what did I do the day of, I mean, I was just crying. I didn’t know what to do, I had no idea, but thankfully, I’ve already had a network of people that I could have reached out to, and I knew that I could find the job that I really wanted. I reached out to my friend at UBS and she was amazing. She actually helped me get a job two weeks after losing my job, and I decided to say no because that’s not what I wanted to do. It was a job, but I was looking for a job that I wasn’t going to be happier. At this point, I realized having a great manager and someone that believed in you was really important and having experience bad management, I wanted to make sure that I was placed somewhere where I knew I was going to succeed, and I really looked for that, and I waited until I found it and that was at CitiGroup.

Priscilla: Amazing. I think that takes a lot of bravery to say no to something especially when you’re unemployed and maybe yes, you had that financial security for a little bit, but still, you’re always thinking what if I run out of money or what if it takes a long time? Because job searches can take such a long time, but that’s amazing that you were able to say no. What was the new role at Citi?

Jessica: So, at CitiGroup, when I was looking for my job, I decided that I wanted to do something with impact and that was something that drove me and changing the lives of other people, but I was less interested in the environment. I was most interested in the S of ESG which is around social responsibility, and I went to community development and there, I was working around the community reinvestment act which is a law that was passed in 1977 that forced financial institutions to invest in low and moderate income communities around the United States depending on where they had branches, so this is a law that I feel now should be replicated into other sectors of forcing people to invest in these under invested communities, but I was working across different divisions to do the reporting on how they were doing this, in addition, working with regulators to make sure that the firm was upholding their end of the bargain.

Priscilla: Okay, and so when you were at Citi, what does the career ladder look like? What was the level that you entered at and then what do those promotions look like for those who are wondering?

Jessica: I entered as an Assistant Vice President and that was actually a promotion from my Goldman days and also, like, they paid me more, so that’s another thing I tell people just because you’re at a company doesn’t mean that there is another thing out there. You have to be really brave and don’t pigeonhole yourself to one company without really knowing what’s available out there, so I started as Assistant Vice President. The next step would have been Vice President and then following that is Senior Vice President, and then Director and then Managing Director, etc., so that was a career ladder. During that time, I was there for about three years, it would have been in my promotion year if I would have stayed, but my manager and I had very clear communication in terms of me knowing that I was going to go to business school and him helping me get to business school, and nd I was really happy and blessed for that but I think that having that, I really enjoyed my time there and really think that a place like Citi and all these other organizations, there is that  career ladder and there are opportunities to move up within the firm, but I wanted to see what other opportunities were out there. I felt that it was a great job, but I was interested in doing a little bit more.

Priscilla: And so at Citi, did you already know about careers in venture capital or when did that conversation start for you?

Jessica: Yeah, I had no idea what venture capital was at all, and even when I was applying to business school, I was like, I’m going to go be an investment banker. I want to work in private equity. Nowhere in my mind did I understand what venture capital was. I think, and I remember my consultant and my mentor, she would say, “Yes, I think you’re more of a venture capital person,” and I will say, “I don’t know about that,” but mostly, I would say that because I didn’t know what it was, but I think I started getting a little bit more interested in it because my brother unfortunately ended up going to prison and I realized that the prison industry is a $5 billion industry where mostly women of color are the ones that are contributing to funding these companies, and not funding, but like the customers of these companies, and I realized that and then thought about how old the technology was there and how I can improve it, and that was through venture capital and I looked at a couple of companies that were in that space, and then from that, I found Kapor Capital, and I was super excited to hear about Kapor Capital and what they were doing more so than actual, like, what venture capital was, and that really is what sparked my interest. I spoke to a couple of friends that had done the internship and they let me know about what they were doing and what they thought about it, and helped me through the application, and thankfully they accepted me, so I was really excited for it.

Priscilla: Very cool. So, you were there the summer before you started your MBA program, right? So, what kind of projects did you work on as an intern?

Jessica: I think the Kapor Capital internship is very unique. It’s 50-50, so 50% of the time you’re doing venture capital stuff, and then 50% of the time, you’re working with a startup. So, I had the opportunity to work with Aclima who actually just raised a $40 million round, series B around starting to buy a Latina, and they’re working on collecting air quality data all around. I think right now they have mostly California, but they hope to expand it to all around the world. So, that was a great experience, and on the venture capital side, I was working on diligencing, so looking at the different deals that were coming through, looking at pitches and seeing whether or not we would be investing in them in addition to other things within the venture capital realm, like going to events and meeting with founders, etc.

Priscilla: So, you decided that you were interested in VC during that summer internship?

Jessica: Yeah, I think I was able to really see what venture capital was and experience it, and from there, I realized that there are very few people of color in this industry, and I think that’s what really motivated me was knowing that we need more people like us, but there’s not a lot of us that are willing to pursue it because it is a long journey and sometimes, we have other responsibilities that we need to take care of first, but I was very interested in just the mission and how I would be the one choosing which companies get to live or die and investing in the community that I cared about and knowing that I had this unique perspective living in certain communities that I could bring to a deal team.

Priscilla: And so, I know you are now at MIT Sloan, so what has that experience been like for you just developing as a leader and also exploring more in finance and in VC?

Jessica: Yeah, I think that one, getting an MBA is great and I’m really grateful to be at MIT and being in this space where I can seek opportunities and really pursue them, but I think that people, at least people of color, need to realize that sometimes these spaces aren’t for you and you just need to make sure that you make it for you and you need to push forward, like I’m very involved in the diversity, equity and inclusion committees and trying to increase representation of Black and Brown people at MIT Sloan, but there is a lack of diversity in all of the programs and we need to continue to create that path, but sometimes, it just does create some sort of attacks on the students because then, that prevents them from focusing on recruiting on, or not recruiting, but like on other things that they might be interested in, maybe starting a business, etc. Being at MIT, I think that looking back, I think it was a perfect school for me because I ended up also applying to the Harvard Kennedy School which is right across the street and very easy to go to, but I think that I really enjoy the aspect of entrepreneurship and technology, and seeing what everyone is working on is really amazing, and as a future venture capitalist, I think that having that network and leveraging the entrepreneurship in combination with some of the financial skillsets that I gained will help me get into venture capital in the long run. I’ve been involved in Mint which is like a competition put on by Wharton Management Impact Investing and Training but it’s a competition where would you look for a company to invest in or to propose to invest in that is making an impact and you’re trying to get $50,000 of funds to invest in this company that you selected. In addition, I’ve been involved in internships, so I’ve been working with Luna Cap which is another scholarship that I received at MIT, not at MIT itself, but it’s across different schools scholarship, and it’s for Mexicans and for veterans, and it really depends on the funding, but it’s also another amazing network and I have been interning on their venture arm, which is the Luna Cap Ventures, and we’ve been doing more of a debt VC which is a little bit different than equity or what I was doing at Kapor, and then at New Market Venture Partners which is an ad tech and future work fund that I actually did my summer internship with as well but I did a spring, summer and I’m doing a fall into master internship because they’re working on fundraising in addition of just doing diligence on their deal flow, but ultimately, I’ve really enjoyed my time at MIT Sloan. I definitely feel that I’ve made great friends and long time friends that I will keep for my future and wherever I go.

Priscilla: So, one thing I’m really curious from your experiences, the people that you met at these funds who they’re calling the shots, they’re at the highest level, are these people who are all ex-bankers, or what are those career paths or even qualifications that you’ve seen for people that are in this space?

Jessica: Yeah, I think most of the time, it really depends what stage. So, Kapor Capital was more earlier stage. At New Markets and also at the debt fund, it’s more later stage, and debt, the investment is very heavily associated with the balance sheet and the health of the balance sheet of the company, so I think, of course, for the venture debt and for the later stage, I see more bankers and I see people that have been in banking being in that space, but I also see people that haven’t done banking. So, I’ve seen people that have started a company, been entrepreneurs, been working on the operational side of things, and then I also, in the earlier stage side, I do see people that have different experience, whether that be in finance or consulting, and thinking about operational marketing. It really just depends, but it is very heavily banking and consulting, and that’s something that I hope to change and something that we all need to change, and unfortunately, the reason why it’s like that, it’s because in order to be an accredited investor, you need at least $1 million of liquid capital and/or a salary of $250,000 a year and only consulting or bankers would really be able to have that salary. So, that’s something that traditionally, it’s been like that because of those entrance of the industry and because you’re a banker in venture capital, then you’re gonna look for a banker and venture capital, but you honestly don’t need any of that. I think if you were really talking about what you really needed to be in venture capital, is you need a lot of money, and unfortunately, not a lot of people of color have a lot of money and that’s what really draws people to it.

Priscilla: It’s such a good point. Yeah, and so let’s say someone’s listening to this episode and they’re like, “I’m really interested in pursuing venture capital but I don’t know any of this jargon or how this works,” when you were learning about it, was there like a book or like anything that you use to help you ramp up quickly and understand, like, the deal flow and like all those things?

Jessica: Yeah, so I think that definitely, there’s a lot of blogs out there about venture capital. You need to do your research on the funds that you’re interested in, know who the top funds are, who the big players, Venture Deals is a book and is what people call like the Bible of venture capital, and in terms of podcasts, like maybe the 20-minute VC provides interviews with these fund managers in addition with people in this space, but I think talking to people about it, but not just talking to people, but I feel that sometimes, people are saying, “Yeah, I want to do venture capital, can we set up a coffee chat and you set up a coffee chat?” and you don’t realize that these people have a lot of meetings every day, and you should probably do a little bit more research and background on what venture capital is or even send over a company that you think that they might be interested in that allows them to feel like, okay, I will spend 30 minutes with this person because they sent me this deal that I wouldn’t have otherwise gone, and I would say try to get some experience if you can working for free although I hate when people work for free because I feel people should be compensated for their time, but sometimes, you do have to do that in VC, just try to see if you can do a scout or start learning more about being inside the industry, but never give up. You need to be very persistent, ask to meet, be bold and reach out. I think for venture capital, you either know how to do diligence and know whether or not an investment is good, but the other part is just networking to either get new deal flow or also, to get someone to invest in your fund. So, if you can really prove that you have those skills, you would be great in a venture capital setting. But yeah, if you are from an underrepresented group, you should definitely look into your network and see, I know for Latinos, there was like a LatinX VC where on Twitter, on my Facebook, that you can join and they post jobs and articles, and different newsletters on how to get into the space, but I’m also happy to share with you, Priscilla, a link that allows people to see, there’s like a whole one pager on how to get into venture capital and blogs and books and a list of resources that you can leverage.

Priscilla: Very cool. Yeah, I could definitely put that in the show notes, but yeah, Arlan Hamilton, her book is called It’s About Damn Time and it came out in May of this year, yeah, she’s awesome.

Jessica: Yeah, that’s an amazing book, definitely read it when you have time.

Priscilla: Great, so I guess my last question for you, I want to talk a little bit about imposter syndrome. I think a lot of us who were the only ones or were the first in our families to go to these elite schools or enter these elite spaces that like you said were not designed for us, how ow have you grappled with those moments?

Jessica: Yeah, I mean, I think that being laid off, I hated it, but I always go to that moment and realizing that everything will be okay and that now, it will be even better because you have an amazing school behind you that you could leverage for whatever it is, but I think that I’ve become more confident as to who I am and what my background is, and I own it. It’s taken me a while, I don’t really remember what it did take for me to get here, but I realized that if you’re not speaking up, if you’re not the one saying something, nobody is. So, you need to be that person, regardless if it is painful, or if you really have to get out of your own bubble to do that, because otherwise, your community will not be heard.

So, for me, I do it not for me, but for other people and to bring other people together, and I think with that, it’s allowed me to find this confidence within myself to be like, whatever, like, it happened, like I did what I had to do and I am not going to change for anyone regardless of what the thing is, and I think that only comes with age, and there are times where I do make mistakes and maybe I can say things better or being nicer, or whatever that is, but I think at the end of the day, I pride myself on trying to give everyone the true Jessica and provide people with my honest thoughts without having to sugarcoat anything, and sometimes, that’s hard to do because then, you can come off as, like, people say aggressive or maybe not as refined as you would have liked, but I told you what I thought, you asked me for it, so it’s not my fault that maybe you don’t like what you hear, but I think that at the end of the day, I just prefer not to happen to regrets for me not doing anything.

Priscilla: Yeah, so I think what you’re talking about a little bit is being authentic to yourself and being unwilling to blend in or change who you are, or mute parts of yourself just to fit into another culture.

Jessica: Exactly, and I think also, it’s learning about our history and the history that Black and Brown people have faced in the United States and knowing that we have nothing to apologize. All of this has been really brought to us because people think that White people are superior or because we’ve been taught to believe those things through propaganda, through the media, whatever that is, and we’re over here trying to act a certain way for other people. No, why are we doing this? Who told us that we needed to do this? And the reality is that we need to change that.

Priscilla: That is a great place to end, very powerful words. Thank you so much, Jessica, for being here for giving it to us straight. I can’t wait to have people listen to your story and be inspired to break into VC or to go any path other than finance.

Jessica: Yeah, no, I mean, thank you for having me and yeah, feel free to reach out to me on LinkedIn or however you want, happy to chat with people, and thank you again for the opportunity.

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