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Full Transcript:

Note: This is an original transcript–edited for sense, length, and clarity.  If you have any questions or concerns, please email our host, Doria Lavagnino, at doria@sheventurespodcast.com.

Intro: 

Doria Lavagnino: This Ivy League grad started learning about capital markets at Morgan Stanley. She pivoted to the startup world and joined accelerator Y Combinator, where she did business development for the e-commerce startup Shoptiques, still in business. She held roles at Saks and Estée Lauder, focusing primarily on the intersection of consumers and technology before returning to school to earn her MBA from MIT Sloan School of Business. From there she entered the world of venture capital, most recently, as the principal for VamosVentures, where she is focused on funding more Latinx entrepreneurs. Ashley Aydin, welcome to SheVentures.

Ashley: Thank you so much for having me.

Doria: It is great to have you. I would love to talk about your experience as a first-generation American and how that has impacted you.

Ashley’s Early Years

Ashley: My father emigrated from Turkey in his early 20s, and my mother’s a traditional Brooklyn girl. Both of them never went to college. They didn’t really focus on school. My experience has been around, just sort of survival mode and having to figure out things on my own. As an example, when I was looking at colleges, I really didn’t have anyone to lean on to tell me what the top universities were, what the Ivy League was, and what I’d be getting myself into studying economics and political science. What I had to do a lot of times was rely on folks who have been there before who were willing to lend a hand, who were willing to have a 15-, 20-minute conversation with me about their experiences. I think that’s sort of inherent in how I work and it shaped me as a human being, which is always being inquisitive and asking questions and learning about people’s stories.If I didn’t hear about people’s stories, then I wouldn’t even know what path to take to get to where I was in this venture capital space.

Doria: Where did you go to high school? I’m curious. Was it in New York? 

Ashley: It was in New York. It was in Staten Island. It was a small school. At the time, about 90 students. I was part of the first graduating class. It was called the CSI High School For International Studies. And again, very experimental, part of the Bill and Melinda Gates Foundation, that gave funding to the school initially, and was a new curriculum. I guess it was an experiment as I mentioned, but 90 kids are learning more of this international focus. You had Chinese, Japanese as languages. You had the economic side, and the implications for the global economy, and so it was a really interesting innovative curriculum.

Doria: Do you think that it helped you in terms of career development or thinking ahead?

Ashley: It’s very interesting that you mentioned that, because I do, in that I was part of the first graduating class.We almost had to make things up as we went. It was almost entrepreneurial in that sense. I mean, obviously they had a framework of how to take classes, and what classes they were gonna offer, but everyone was new to this type of experience and so, it was very much the entire class going “this isn’t working.” 

You know, we had labs. We had more interactive experiences. We had music classes. It was a really interesting experience, but absolutely, I think it really taught me to sort of pave my own path.

Doria: So important in life, rather than waiting for someone to pave that path for you. You’ll be waiting a long time, right? By the way, you mentioned Turkey. Is everyone in your family, extended family, okay?

Ashley: Yes, knock on wood. Everyone’s okay. Everyone is mostly in Istanbul, but it’s so unfortunate what’s happened. I’ve had friends affected and I’m hoping that there’s aid sent there and that things get sorted out, but everyone is in my thoughts and it’s absolutely terrible.

Doria: Absolutely, mine as well, so hard to transition from that, but I will nonetheless. Your first job out of college was at Morgan Stanley. So, I think of Morgan Stanley, how I remember it when I used to go in — my dad was a client — and it’s very kind of white collar. In hindsight, what value edge or insight did working at an investment bank give you?

Ashley: I thought it was a wonderful start to my career in the network that it brought me and the training that it provided me. So, you know I got to Morgan Stanley and I had an idea of how the markets worked and how public companies worked. But until you’re actually in the weeds, following these companies, learning how to do these financial models, and talking to people who move a lot of money. You’re like, wait. I’m 22, 23 years old, and I’m responsible for a lot of things, right? It gives you a sense of responsibility very early on in that training of being a people person. 

I actually went to Morgan Stanley yesterday. I visited my old boss and my old team. A lot of things have changed, but what stayed current is sort of some of the principles of Morgan Stanley, which are to put clients first, diversity and inclusion matters, think in innovative ways, and I think just that ethos and those principles I’ve carried on throughout my career throughout my life. I mean, I’m doing more impact, orient, and investing, and I think back to more, and I’m like well, I learned one of those principles there.

Doria: How was it being a woman there? I know it is a very male-dominated sector.

Ashley: I felt really comfortable on my particular desk, but you always hear these stories and these very interesting experiences of it is a boys club still, right? You sort of have to play the game to fit in. There were some elements of that while I was at Morgan Stanley but not so much where I felt pressured or uncomfortable. I think it all really matters how you approach the situation and how you have these conversations to say, “Hey, listen, this isn’t making me comfortable.” Or like, why don’t you approach a conversation in this way or this was an instance that, maybe things could have been changed in these ways. It’s wonderful that I see a lot of moving in the financial services industry and making it a more inclusive environment and having these conversations out in the open.

Doria: Did you feel comfortable having those conversations? Are you the type of person who could just do that?

Ashley: I think I can. I don’t know.

Doria: Some women can. Yeah.

Ashley: I think it’s like I’m pretty bold in my asks and the way I bring up things, And so , my attitude is what is there to lose and I don’t know if that’s the right approach, but I’ve always had, knock on wood, a very good relationship with my manager, my higher-up, of saying, listen let’s level-set here and here’s my perspective, and what are your thoughts and let’s work through this. I’ve brought up instances. I’ve brought up feedback to managers that have been uncomfortable, but these are conversations that need to be had. 

Doria: I love that you have done that because ultimately, the alternative is to hold it inside and then you just resent it and it festers right. Either way you get it out and it’s either the right fit for you or it’s not.

From Million Dollar Company to Startup

Doria: From Morgan Stanley, you then pivoted and you were a part of Y Combinator, which is an accelerator, in my understanding, and you were involved in a company called Shoptiques which, when I looked at it, looks like kind of like an Etsy for boutique stores that’s still around, which is super cool.Tell me about that.

Ashley: Shoptiques was part of the Y Combinator program. I worked at Shoptiques. I was doing a lot of sales and business development and pretty much all hands on deck at this early-stage startup. I made that jump from Morgan Stanley to Shoptiques because I said to myself, I really want a true experience as to how things go on at an early-stage startup. And it was night and day. Right to your point, very structured at Morgan Stanley. I got to the startup. I was working weekends and all these crazy hours for half the amount of pay — probably less. The vision and very much liking my team and being on the grind all the time. That’s what I realized was real life and all the glitz and glamour that you see these founders and all these companies in the press. I mean, yes, that’s nice, but that’s not really what goes on behind closed doors, right? It’s very hard to scale, sort of, and so I got the real take as to what that means at Shoptiques and the company is still around today. I think they actually recently rebranded, but I think it’s still going strong. And I love the mission of that was empowering small, medium-size boutiques and stores to digitize their offering and to sell online because they don’t have resources. 

Doria: Absolutely.

Ashley: Right, like the big conglomerates.

Doria: It is nice to have the one platform to go to. And I didn’t realize it rebranded because I looked them up as Shoptiques and they were still there.

Ashley: I think it’s I think it was maybe a week or two ago that they did this. I just found out.

Doria: Oh, okay, interesting. So, you took a major cut in pay for that experience of being in a startup, which is a one-of-a-kind experience. I love what you say about the glamour and glitz. I’ve watched so many shows on Netflix and Hulu, like the WeWork one, and they’re so over the top. Maybe that’s some people’s experience, but for the most part, it is a real grind to your point.

Ashley: Absolutely. I love that WeWork series because it showed the rise and fall of something that everyone thought was going to be the next best thing. There are multiple stories like that. Even if you know stories that haven’t been told in the media and the public, it’s nice to see that there’s so much more behind the founder. It’s the team, it’s the investor, it’s the business model. It’s the culture of these companies that really make things work and click, right? I think some of the best companies of our time just have amazing leaders who know how to sell folks on the vision, but even more so know how to hire the right people, and bring people together around this vision that can build in scale and that they could execute and make it into a hopefully huge impact-oriented company.

Learned Skills That Made Ashley a Great Venture Capitalist 

Doria: Can you share a few of the key takeaways that you learned when you were working at an early-stage company? And how did it help you as a venture capitalist today?

Ashley: Number one is culture, and you know that may sound fluffy, but I think it’s true. If you have a founder that is building culture, that’s inclusive, that respects employees, that listens to their needs for development and growth as you build in scale. Because it’s hard as a founder. You’re thinking about so many other things right outside of culture right, but that it does prioritize culture. That’s important. 

The second thing is a viable business model and big market. Do you have a business model that can scale in a quick way because venture capitalists want to see growth, a lot of growth in a short amount of time. 

And then to the market point: Are you building around a huge market that is sticky, that is growing, and that has a lot of tailwind? So those are the three things that I would say, I came out of the startup saying. This is really important, now that I’m on the investor side that I look for in a lot of the companies. And then one thing I forgot is knowing the consumer, understanding them, being obsessed with them, whether it’s a business or an individual consumer like you, and I just knowing what the priorities are, what the needs are and how much they’re willing to pay for all that fun stuff. 

Doria: That is so true, and I think in some ways it’s more important even — not to say that what the venture capitalists that you’re pitching, what they think isn’t important — the consumer almost is more important, and you understanding that piece of it because I have heard stories of people who pitch a 100 VCs and they come back with all these different takes on what their business could be at scale. It can be really, not demoralizing, but confusing, I guess would be the word, right? If you know your consumer and you know what you’re doing, then you can go back and incorporate what is valuable and leave the rest.

Ashley: Absolutely. When I work with our portfolio companies, I do see them and reassure that everyone’s more consumer first and understanding the consumer.Then building and iterating on the products while having that constant feedback loop with what’s working in what’s not, and that’s such a beautiful way to build.

Doria: Yes, iteration, totally agree. As if it weren’t enough to go to an Ivy League college, you then got your MBA at MIT. I’m curious: How did you make yourself stand out from other applicants? I’m sure you had great test scores, great grades, you had work experience. Was there anything else that you feel made a difference?

Ashley: What worked with me? I think in my application is doing a lot of research and soul searching, if you will, on what I wanted out of business school and where I wanted to go. So, when I was listing my five MBA programs that I wanted to apply to, I had spent the time talking to students in those programs and learning well, what makes this program unique and in doing like, almost like a personality fit a match. So, for me, going to MIT was more of…I want to become more, you know, technical, and have that orientation to things like AI, machine learning, crypto, all these things that were coming out of MIT and are still coming out of MIT, that the school’s at the forefront of. 

When I was doing my application, I realized I’ve done a lot of really cool things, quirky things, but what’s really important to me at this stage of my career in my life is giving back in a very impactful way, meaning putting dollars and allocating dollars behind diverse founders because I said to myself, there are probably founders like me out there who just don’t know how to reach out to venture capitalists who don’t know how to start companies but have really amazing ideas, and that just started weighing on my mind. And when I was doing my applications to all the business schools that was front and center, like this is what I’m going to do with this education. And this is how I’m going to make a big impact. And I think a lot of the schools appreciated that.

Doria: And to your point, you’re known for your expertise in technology and health and in making impact investments. Before joining Vamos, you worked at a couple of venture capital funds. Was it initially difficult to find the right fit in terms of the VC community?

Ashley: I would say so. I always sort of had a theme with my VC career in that I’m very consumer oriented. That’s just my background whether I was at Morgan Stanley or the startup. I was always [interested] in consumer investing, marketplaces, e-commerce. But even outside of that, fintech solutions, health and wellness solutions that orient around the consumer. The patient, if you will, the buyer. I was trying to find what funds appreciated that perspective, and that’s how I joined Brand Foundry Ventures and Founders Factory, doing consumer healthcare investing. Fintech platforms focus on wealth generation and educating consumers around financial wellness. But I think when I met Marcos Gonzalez at VamosVentures as he was building, and eventually closing this fund one, it became more apparent to me. These crazy numbers that we still have in the VC ecosystem of Latino and diverse entrepreneurs getting less than 2 percent of venture dollars.

Doria: It’s crazy.

Ashley: Exactly. And so I was like, you know what? I’m going to join Marcos and help hopefully move some of these statistics.

Doria: Bringing us to VamosVentures, so I didn’t realize this, but in 2021 they wanted to raise $25 million. It was a seed fund to help Latinx and diverse founders, and they raised double that amount: $50 million. Incredible market appetite for what you were pitching at the time. And so what do you think it was that really was interesting?

VamosVentures

Ashley: I think it was the specialization around Latino and diverse entrepreneurs in this focus. I mean if you look at some of the demographic trends, the Latino population in particular, accounted for 60 percent of the U S. population growth between 2005 and 2020 and even more so in the coming years. 30 percent more entrepreneurial than most demographics, right? We’re gonna hold a lot of spending power in the next couple of years as well. And so, I think a lot of our partners were tracking these trends, and realizing that investing in this community is going to be is really important and we want to get ahead of the game in supporting a fund, like VamosVentures and their focus in these more differentiated, more, culturally aware competent entrepreneurs. 

Doria: What is the average investment that you make?

Ashley: We are mostly seeded Series A funds. What that means is we’re still investing at the earliest ages, but in terms of a check size, it could be anywhere between $500K to $2 million. We could lead rounds, co-lead rounds. We do a lot of healthcare, fintech, future of work, sustainability. Those are our four main areas. What we look for in founders is obviously, Latino or diverse founding teams, but even a step more than that is: Is there some sort of impact orientation to the product and solution? For example, in healthcare, are you focused on affordability and access? In sustainability, are you focused on a clean supply chain and just a better world? 

Doria: Can you give us an example of a few companies that are currently working on those things that really kind of exemplify the action or the impact investing angle?

Ashley: Handspring Health is a mental health company that we invested in last year. What they’re building is a hybrid model for children and basically pediatric mental health. That is more skills-based versus you see, a lot of these mental health companies popping pills all the time, and that’s sort of the end solution, which you know, humbly, we don’t think it’s the right way. It’s family-oriented, it’s skills, building development over time. We absolutely love their model and they’re, you know, getting a lot of traction and respect. 

Another company [is] Suma Wealth. Suma Wealth is focused on financial education and building wealth for Latinos. They have a big bet on sort of Latinas and being culturally competent in the content that they produce to this demographic, and hopefully making future millionaires, billionaires, and whatnot. These are the types of companies that we’re excited about and you know I could name a bunch more, but hopefully, that gets the community involved.

Doria: Those are great examples and for our audience, so that they know: As a venture capitalist, where do you raise money from? Who are your investors? And who do you have to report to?

Ashley: We raise money from LPs, limited partners, they’re basically, I often say they’re our own cap table. They are supporters, they funnel us money to then execute and find the best startups. A lot of our partners, thankfully, are mission-oriented, impact-oriented, in that they want to see our portfolio. I mean, I think the latest stat was 90 percent identify as Latinx, 100 percent diverse. We have 40 percent women. I want to personally, my mission is to increase that to 50, if not 60 percent. But these partners want to see that impact and their dollars going to these types of things. And so that’s why we came [to be] over-subscribed. We had a lot of early believers in this first round and knock on wood, hopefully in this second round as we go out to raise in this new year.

Doria: You’re gonna raise in 2023.

Ashley: Yes.

Doria: Exciting. So, you’re very passionate about the disparity as you mentioned of brown and Black people that face what they face as consumers and as founders. And I kind of wanted to dissect that with you. In what ways do you see brown and Black consumers getting marginalized in healthcare? You mentioned an example of how Vamos is helping. Are there other ways in which anyone can help?

Marginalization 

Ashley: I think just having sort of a different lens and being patient and coming with an understanding that not everyone goes through an experience in the same way. So, as we talk about healthcare, for example, if someone is dealing with an aging parent or maybe a parent that’s sick. You go to the doctor’s visit as a unit, right? It’s like a family orientation focusing on the problem, and maybe your parent or grandparent doesn’t speak fluent English, right? And so, there’s even a language barrier in some instances, and , there’s a lot of frustration from a provider side in that experience, but I think as this country is becoming more and more diverse, there’s more of that cultural understanding that cultural competency that will make these experiences more seamless for a multi-racial family or Latino family, who again is second-generation or first-generation or what have you. But there’s still these nuances and the experience is the same thing with [college]. I was talking to a friend the other day about being a first-generation college student and being the first in your family to have a high-paying job. Well, how do you focus on building wealth not only for your family in future generations but even caring for aging parents and knowing what to do and just dealing with all this stuff? There are these differences and experiences that we should all be aware of.

Doria: How do you balance it? How do you have your work-life balance with what you do?

Ashley: It’s hard.

Doria: I bet. How many hours a week do you work? What’s a typical day for you?

Ashley: Oh gosh, it’s all up in the air.There could be a day where I’m waking up. I’m having breakfast and going to the gym and feeling great, and then I’m on Zoom calls or doing coffee chats until 9 pm. There’s days where I start very early, and then I have a dinner at night with investors and founders. We’re very much outside of the day-to-day of Vamos, which is meeting founders, working on strategy and portfolio allocation. There’s also a big ecosystem-building component that we want to bring, Latino and diverse entrepreneurs and funders together to hopefully support each other so that these numbers can move to the right direction. I do a lot of that outside the day-to-day as well.

Doria: You’re really committed to that and that is such a huge issue, like the 2.5 percent of women of color tech founders, I believe it is, that raised venture capital. It’s so paltry, and even when you think about executive women venture capital firms, I think it’s something like 10 percent right now. 

It reminds me of the work of Dana Kanze. She’s the one who did the study that showed that women are asked certain kinds of questions as founders that put them more on the defensive in how they answer, whereas men are asked typically more promotional type questions and then are able to answer in that way. So, there are these biases that exist, and those are really hard to deal with because sometimes people aren’t even aware that they have them. 

Ashley: It’s interesting. Just quickly on that point, too, because I talk about it with my female investor friends all the time. And you know we all are like, hmm, we notice nuances in talking to female founders. I mean, there’s that mutual understanding. So, for us it’s fine, but a lot of funds do more diligence on female founders versus a male founder, and we’re all like, “Well why is that, when this female founder is freaking awesome?”

Doria: Exactly. Have you seen, since you’ve been in venture capital, do you feel like there is any sort of change?

Ashley: I am seeing change that’s promising. I mean, you see these organizations like Blck VC, VCFamilia, LatinxVC. They’re all popping up in the last two, three years to bring communities together around the Latin and Black experience in the startup and venture world. Then you have wonderful organizations like All Raise that are bringing women together in this space. And I think just having those conversations and those groups to go to when you’re dealing with an uncomfortable conversation. These are people you can trust, so absolutely, and there are champions and game changers in this space that are building and running funds that are funneling dollars to where they should go.

Doria: Okay, a female founder is pitching you. Tell me three things that impress you and three things that are a turnoff to you.

Getting Funding 

Ashley: Passion, for sure. I love big personalities and big visions. The second is going back to knowing the customer, knowing the customer down pat and some stats, and keeping your eyes on that. And the last is again, painting sort of a picture on scalability of the market and the business model. So those are the three things I think on the constructive side. Not asking at the end of all the conversations, like what’s the next step, and keeping investors accountable is something that I see a lot of fall through on that I wish more founders did. On the same note, I guess as a number two asking the investor, what’s your value like? Tell me how you work with a portfolio.

Doria: Right, turning the table. 

Ashley: Exactly. I want to make sure that you are the right fit for me too, and I think lastly is, not letting that passion shine through where that personal story and being vulnerable shine. I think the best pitches have some sort of vulnerability to them and a personal story or how they got here, and the storytelling component is extremely up there for me.

Doria: Does it matter how much they’re able to talk about the numbers forward and backward?

Ashley: I think knowing your numbers is a sort of one of the givens, and that this is your baby. You should know everything about your business, but it doesn’t have to be spewing numbers at an investor. I think it’s more of, at least in the first conversation: How did you get here? Why is this an actual problem? Why is this a problem that is important to solve, now? And how are you going to go about it in a differentiated way? And then, of course, the numbers back that up. That’s really important there.

Doria: You’ve told us three things that you see, and three things you wish you saw more of. I’m assuming that in some cases women pitch, and then they thank you, and then they don’t follow up or negotiate or any of that. That’s typical.

Ashley: That’s typical, and I think that all requires just the right investors on your side or support system on your side. To say you know that investor hasn’t gotten back to you in two weeks, go shoot them a note and give them an update on what’s happened in the past two weeks, and ask them for a true deliverable right after that email. Or you get these terms: negotiate on X,Y, Z points because you have a lot of leverage here. It’s all about who you have around you as well as your support system in having those conversations openly.

Doria: That makes a lot of sense. As you know, female venture capitalists in decision-making roles, we said it’s about 10 percent. What are your colleagues doing to ensure that we get closer to gender parity?

Ashley: Hopefully they’re sticking to the space for long enough to get promoted and be partners or go start their own funds. I’m seeing a lot of stickiness there. Thankfully, in the last few years. I think that the other thing is, raising your hand and having a lot of ownership as it comes to deal flow and developing relationships, and just being present out there so that you create a brand yourself and have wonderful founders. You know, develop relationships with you and different stakeholders in the tech ecosystem.  

I would say finally, it’s being true to yourself and what matters to you. For me, this really matters to me, and I think naturally a lot of people have started to notice that and so if caregiving matters to you or the family economy matters to you, or woman’s health matters to you, doubling down on that and making that known.

Doria: Love it. In 2023, where do you see the key growth areas? Since I know healthcare and the consumer is really your focus area. What do you see happening there? 

More Advice

Ashley: Oh, I’m very much trying to find something in elder care and aging in place. I think that we’ve done a terrible job as a country in caring for our elderly population. It’s an extremely fragmented experience. No one wants to think about it. And I think new technologies that think about getting families together to think about these issues as well as how do we make the elderly population comfortable in aging in their own homes, if that’s the choice, or even going to a skilled nursing facility or whatnot? And empowering individuals is going to be, I think, the next big wave and something that Vamos Ventures is extremely excited about.

Doria: That is so much needed. My mother is 88 years old. She does choose to live at home and it is a very fragmented situation for her because she’s extremely independent. She orders her groceries through Instacart. It’s an okay experience and she seems happy, but I think it could be so much better, and I love that because there are so many people that are aging and I feel like as people age in America, they become invisible, which really is a neurosis of our society. It’s really sad. 

Your VC time is very limited because you see so many pitches in a day, a week, a month. What can founders better do to meet your criteria to get a first meeting with you?

Ashley: I think generally as you approach investors, doing research on the investor goes a long way. And so, as you’re building your, let’s call it CRM, or let’s say sell list, what have you of investors, knowing what they’re focused on, what their thesis areas are, what check sizes they write. You don’t want to go to an investor that, maybe they do early stage investing, but really what that means is Series A investing and you’re a pre-seed company, right? I think coming to the conversation with information on the investor that you’ve done some homework goes a long way. 

For example, I think something that would stand out to me as if a company is like, oh, you’ve invested in these four companies. That is related to what I’m trying to do in healthcare as well, right. And that’s like, okay, well, you know what we’re all about here at VamosVentures. I think doing that: one, speeds up your fundraising process and two, it helps you with the alignment aspect.

Doria: Is there any preference in terms of video email pitch deck?

Ashley: No, I wouldn’t say so . Usually, the way that we correspond with founders is through email and then subsequent call or video, but I think just sending information over in an email, a deck, and some bullet points on momentum in your company is completely fine. 

Doria: A lot of investors do ghost people. How do you know, should you just assume that if you don’t hear from an investor they’re not interested?

Ashley: I wouldn’t just assume. There’s a lot of things in the background happening at funds. For example, the fund could be, I don’t know, dealing with an LP situation or could be on three live deals at the same time, and the process is slower. I would be resilient, persistent in getting answers from the investor. Of course, if you’ve done all that and haven’t heard back in two months, then I’m like okay, let’s carry on. Unfortunately, that might be the experience for a lot of founders. I could tell you at VamosVentures, we always get back to everyone whether it’s a yes or no and we provide, hopefully, helpful resources. But be persistent and try to get that answer. I’d say you know after a month if you don’t hear back, then just move on.

Doria: Move on. Persistence is something that I really see in you. I really admire what you’re doing in the space. How can people find out more about you and VamosVentures?

Ashley: I’m happy to connect on email. My email is just ashley@vamosventures.com or LinkedIn. I’m very active on LinkedIn. On Twitter, just @ashaydin. Please feel free to contact me. I’m always down for a chat.

Doria: Awesome. Thank you so much for coming on today.

Ashley: Thank you for having me.