Yes We Can

Great. Hi, everyone. Welcome back to this week's episode of Yes We Can. I'm just so thrilled to be here with Cristina Cordova. Hi, Cristina. Hi. How's it going? I'm so good. It's back to school in my household. I always feel like back to school is a new start to the year. It's kind of like my new year. So I like the start of new school years. Nice. Nice. Yeah. I have a toddler starting preschool as well. So yeah, whole new world. Whole new world. Well, congratulations. Good. And I'm super excited for this conversation because you've been an operator and an investor, and I want to hear all about all these topics. We have so much to cover. But before, just two housekeeping items. If there's anyone, for the people tuning in, if you have any questions, there's a way to submit questions online. You can let me know. Or if you have ideas for other guests you'd love to see on the show, please message yeswecan at Cloudflare.tv. We always get so many great emails and always respond to all of them. So back to Cristina. So Cristina, let's go back to I guess 10 years ago when you joined Stripe as employee number 28. And for those who don't know, Stripe is a hugely successful company, and you spent seven years there. This is a dream for most people. I mean, I know when I came out to the Valley, this was my dream to go be part of a company, to be part of it, to make it a huge success. So how did you find that job? And when you founded, did you know that there was going to be a monster of a company? Yeah. So I guess I credit a little bit to kind of right time, right place. There's always a little bit of luck involved with these kinds of things. But it originally happened because I was living in Palo Alto at the time. I went to Stanford, so I was just kind of hanging out in the area for the few years after graduating and working at startups. And I went to a barbecue that this YC founder that I knew was hosting in his backyard. And it happened to be that Patrick Collison from Stripe was at this same barbecue. We got to talking and it turns out that he lived in the house right next to the startup that I was working for full time at that point. And so it just kind of felt funny and interesting. And we ended up grabbing coffee and I learned a little bit more about what Stripe was doing. And I thought it was really interesting. I thought Patrick and the rest of the team, as I started just meeting people who worked at Stripe, were super talented and very much like a step above people who I had met in startups previously and just extremely thoughtful and intense in a way. And maybe six, seven months later, they tried to recruit me to Stripe. And I was pretty committed to the other startup I was at at the time and eventually made the decision to join primarily actually because of the people I had met and gotten to know over a long period of time. And then also meeting Billy Alvarado, who is our chief business officer and still is with Stripe to this day, like over a decade, pretty wild. And I was just super impressed with him and felt that I would actually get a lot of free reign and independence, which is something that I've always sought in roles. And that was exactly what I got. So I was pretty excited about joining. And of course, I thought Stripe would be successful, but I don't think anyone imagined that it would be what is now a $90 billion company, ultimately, which is wild. So I think that was definitely a surprise for a lot of people and really makes you realize that market and timing and so many things have to go right to be able to get to that point. Oh my God, that's such a great story. I kind of have goosebumps. There's some of these stories of where you went to a barbecue and it led to this. But you showed up to the barbecue, you engaged and you didn't brush them off. You said, oh, wow, this is interesting. Tell me more. There's just something really beautiful and simplistic about it, but incredibly powerful too, because you just feel like, well, that could be anybody going to that barbecue. Yeah, exactly. And I think so much of what I love about Silicon Valley startups and these communities are also outside of this area as well now too. But just this willingness to meet with people, to be helpful to people, to provide an introduction, to help someone out with a career chat, that just doesn't exist in a lot of places and in a lot of industries. And I think it's something that's really special about this place. And I've lived here for now for, I've lived in San Francisco Valley for about 10 years, almost 12 years actually, now that I think about it. And you start to take it for granted, I think, because you think everywhere is like that, but sometimes it's going to get out of your bubble and be like, oh wait, actually it is much easier to get a connection here or reach out to somebody or just say, hey, can you introduce me? And people do it all the time. And again, well, that one conversation can really become the catalyst for something much bigger down the road. And I love that too. Exactly, agreed. Okay. So you're at Stripe for over seven years, again, this huge rocket ship, not to overuse that term, but it's a huge rocket ship, number 28 to now $90 billion company. Like that is a huge rocket ship. That's a very up and to the right, but you had many jobs at Stripe. So can you give us maybe an overview of all the, some of the different things you did and maybe which ones were your favorite and why? Yeah. So I started as the first partnerships hire, which at the time meant building distribution partnerships. We had no sales team at the time. So we also didn't want to hire a sales team. So the focus was how can you acquire customers without selling to them directly? So we partnered with a bunch of companies that had platforms that would enable mostly non -technical business owners to set up a business. So think like I'm Christina selling a t-shirt shop and I want to put these products online. So maybe I create a Shopify store or I'm a consultant and I want to send an invoice to someone. I do that through FreshBooks or Xero or some of these other platforms. And so we partnered with all of these different companies to get Stripe embedded as the default payment method on these platforms. And that really significantly grew the business. And I think was a bet that Stripe took early on, which really kind of changed the trajectory and really rapidly grew the business without necessarily having to rapidly grow a team of salespeople, which was great. And so for me, I think being part of that organization and ultimately growing that into several different teams, working on product partnerships and distribution partnerships and financial partnerships with banks and card networks was really great because you get to meet a lot of people. You get to understand a bunch of different business models and ultimately create and forge these partnerships that help your company and another company be successful at the end of the day. And I think I like to think about it as, you know, how could I make this other person who we're partnering with, like get promoted, look good to their leadership, do something that's really powerful. So working on partnerships with like Google and Apple and Twitter, and, you know, those are not experiences that most people have in this kind of role. And that was something I was really excited about. So I did that. And then, you know, with a lot of things, I think at a company that's growing really fast, you have these like pockets where, you know, sometimes someone leaves the company and there's a gap somewhere, or you're just growing so fast that you haven't hired the right leadership. So at one point I managed a partner engineering team. And that was solely because they were like, hey, it's partnerships, you know how to do that. These are just a bunch of engineers who are supposed to help you build these partnerships. So that was my first experience managing engineers. And I realized actually managing engineers is much easier than managing business people. I found that they had more straightforward expectations of what they wanted in their careers compared to business people. So that was easier to manage ultimately. And that was exciting. I got to work with a great set of people there. For about a year and a half, I also led Stripe's diversity and inclusion efforts. So that was a really great role, actually, mostly because I got to work so cross -functionally. So I got to work with engineering leaders who I normally wouldn't work with. I normally worked with like, let's say product engineering leaders who were building end-to-end products like Stripe Connect or other things. And that enabled me to work with like an infrastructure leader, and head of security, and other kinds of teams, which historically I wouldn't spend much time and helped me think about and partner with them on diversifying their teams. So at one point, I ended up running the intern program for recruiting. And we increased the headcount of underrepresented groups in engineering pretty significantly in my time there. So seeing those impacts and being able to work on something where you don't really know if you're going to be very good at it, and you don't have any experience doing it, but you can see the output of that, I think was really powerful for me. And then my last experience there was actually being the head of a new business unit that was working on new financial services products for businesses like corporate card and treasury. And so building those products from like zero to one, when Stripe was actually a lot further along, was also really interesting to me. And I got to manage managers, and engineering, and product management, and so many different functions. And really feeling like I was a cross-functional like business leader, I think was a really great experience. Amazing. I mean, that's just such a collection of experiences. And I love that you kind of learned so many different sorts of things. Have you always been so curious and kind of diving into situations even you're like, I'm not sure if I'm qualified to do this? Or do you feel you kind of gained the confidence to do that as you're at this growth company? Yeah, I think what I always liked about it was that I would take almost like, you know, I kept one foot on the things that I was really good at. So, you know, I still felt like I was working on something that I knew like the back of my hand, like partnerships or platform stuff. And then I would start dabbling in something else, maybe on the side, you know, because I still had to manage that team. But then, you know, I think Stripe was really great at when someone was good at something, just throwing more work on their plate. So that meant I didn't have to give up what I was good at to be able to try the new thing. And that way, I kind of had this safety of knowing, well, if I tried the new thing, and I fail, it's okay, because I still have this, you know, other thing in heart. So even though I think a lot of people would look at my career and say, like, Oh, you took a lot of risks. I feel like in some ways, you know, they were pretty calculated. And, and one of the things I realized over time was that, you know, I really like to feel that lack of comfort in at least some part of what I'm doing. And if I don't, then I get bored pretty easily. Yeah, well, the lack of comfort is a sign of growth, right? It's like you're stretching yourself, you're expanding, and then never quite go back to the same shape afterwards. So there is something that's good, good for you. That's great. And so you know, when you were helping with the engineering program, and you said you were able to increase underrepresented minorities and gender and more women on the engineering team at Stripe, which I think is, which is very topical today. And just curious, what were some of the things you did in the program that were successful, that maybe would be good lessons for all the hiring managers listening? I mean, I think I talked to people all the time saying, I want more women, more underrepresented minorities on our team, but you were able to just do it. So what were some things that worked for you? Yeah, so I really think about it as like putting the onus on the people who are doing the hiring, right? I don't think anyone who's doing DNI can change the world completely on their own. But I think you have to agree with leadership on what outcomes are that you want, and then work with hiring managers to achieve them. So and put a little social pressure on it too. So I think one of the good things that we did was, for hiring, we specifically said that in engineering specifically, every single engineering manager had to source a candidate or two in a given quarter, who would make it all the way to the onsite stage, who was from an underrepresented background. And, you know, I think saying that is one thing. The next step is really, you know, coming up with like our internal Google spreadsheet, the list of every engineering manager, and whether they hit the goal that quarter or not, and then publicizing that across the company. So if you're the engineering manager who just repeatedly does not meet this goal every quarter, you know, one, like, you look like you don't care about this, which is not a good look. And then two, you know, that was something that we would share with leadership and ask them to factor in when it came to performance review season as well. So, you know, I really think you have to have teeth to these kinds of things and social pressure to make people really put time into this, because that's what it takes. Like, if you just look at your pipeline, normally, you're just going to get what you kind of always gotten, and you're not going to go out of band to really think about it more holistically. So that was, I would say, probably the thing that made the biggest impact in terms of, like, full -time engineering hiring. And there were a lot of, like, little things on intern and new grad recruiting that we did that really added up. I love it. I love it. That's such a great, like, practical, practical, everyone can do that sort of takeaway. So thank you so much for sharing that. Okay. So you had this amazing experience at Stripe. It was a rocket ship and with lots of Galaxy left to go, but you left. How did you decide to leave and why? Yeah, I think I got to a point where I realized that I was working on this kind of new business unit within Stripe. But I was spending, you know, more of my time on, I think, a lot of the managing up at a certain point, rather than actually building the product, talking to the customers, and really making sure that we were doing the right thing, especially on, like, zero to one products. Like, you know, finding that product market fit is really critical. And a lot of companies at a later stage just launch stuff and don't really think a whole lot about it because they have customers they can just sell it to. And then those don't, you know, work as they expected in the same way. And so when I realized that I was spending more of my time on that versus time with my team, time with the product, I think I realized that it wasn't stuff that I enjoyed, really, ultimately, and that it was time to really get back to what I enjoyed most, which was that kind of early stage company building experience, which is why I went to Notion. And I actually invested in Notion maybe a year and a half or so before I joined full time. So it was kind of similar to Stripe in that it gave me some sense of having gotten to know the company without, you know, being part of an interview process, ultimately, for a good period before I decided to join. Good, good, great. Okay. Okay. So let's just shift gears. You said invest in Notion before you joined. And you are, today you are an investor, you're investing your own money into startups, which I think is incredible. And so how did you, how did you decide to start investing while you were an operator? And then how did you decide to go do that full time? So when I was at Stripe, I think one of the things I realized was that so much of where I spent my time and my energy was in, you know, financial technology, specifically the products that I was working on at Stripe. And so many of the products that I was working on were products that were helping entrepreneurs, like help your set up a bank account, get a credit card, move money within their company, those kinds of things. And I think having to build products, entrepreneurs, it makes you think about, well, what are all the other things that could be made easier for an entrepreneur? And having met those founders in a lot of situations, I was like, huh, I feel like I want to bet on this founder in a different way, not just to build good products for them at Stripe, but you know, how can I help support them in other aspects? And so, you know, a lot of the companies that I invested, like probably my first five, you know, I made the connection to them via Stripe. So Notion was a corporate card beta user, Whimsical, a company I invested in this year was a corporate card beta user, like investing in my users, I think was one strategy. And these were just teams that I thought were, you know, thoughtful and building really good products. And so it also gave me some insight into businesses that were, you know, completely outside of Stripe's sphere. So B2B SaaS, or developer tools, or those kinds of things. And so I focused on those kinds of companies and connections that I made over the years and really enjoyed helping founders and seeing how they built their businesses and getting some insight into that. Amazing. That's amazing. I love this. So how many investments have you done now to date? A little over 20, I think. Okay. Okay. So that's a lot of investments from a broad cross, because you do early investing. So it's lots of different sectors. And, you know, now that you're an investor, and you're on a lot of companies, over 20 companies, cap tables, and the cap table is the capital table, the companies where they're getting capital from. And one of the sources of capital for these 20 companies is you, Christina Cordova, which is really, really cool. But, you know, I haven't had a lot of people on the segment that have done that. So I'd love to hear in your words, like has anything, what have you learned about cap tables of these companies you invested in and anything you can share with us? Yeah, I think, you know, I primarily invest at the seed and series A stages. So pretty early on. And, you know, obviously, the majority of the capital is provided by venture capital firms, typically. And then there's like a set of room that they leave open for angel investors like me. And one of the things I've been surprised by is, you know, how often when I see the cap table, after I've invested in around, often, like I am the only woman on it, or two women on it, and you have, you know, 20 other angels there. And even in companies where, you know, you feel like, you know, we've come so far from when you felt like it was male dominated, like it's still very male dominated, ultimately. And perhaps some of that is due to like where I choose to invest, which is primarily in like B2B SaaS developer tools and financial technology. Like maybe I was, if I was in some other industries, it would be a little bit more diverse in terms of investments. But, you know, I'm still surprised at, you know, how few other women there are. And, you know, obviously, even more so people of color, who are on these cap tables. And, you know, I would, I'd love to see that change. But I think we have a long way to go there. Yeah, any, any, so I would love to see that change too. And so if there's a woman listening, saying, Oh, wow, I'd like to get involved more. Or if there's an entrepreneur listening, listening, thinking, okay, actually, I want to be purposeful about my cap table, kind of what maybe what advice do you have for those two lenses, the entrepreneur rate, the raising money, how should, what should they be doing? And then for the women, what should they be doing? Who maybe or underrepresented minority people of color saying, actually, I do want to do more of this, like, what, like, where do they start? Yeah, I think for for underrepresented groups, I think, you know, I put yourself into like one of two buckets. So I'm very fortunate to have reaped the rewards of other startups I've been part of and have money to invest in other companies. Not everyone has that opportunity. But but if you do, I would say, you know, spend time with, you know, founders of companies that you respect, and understand, you know, what areas you'd like to invest in and, and just, you know, plainly ask, you'd be surprised how many people would let you into a round, even if they're not actually raising at that moment. Like I know someone who reached out literally to to notion actually via the like intercom chat bot on the side and was just like, Hey, I love your product, I'd love to invest and notion took that person's money. Like, you know, like, like, you'd be surprised. So look at products that you love, and like, try to reach out to the founder in whatever way you can. And, you know, you'd be surprised about what happens. Second, if you don't have that money available to you, I would recommend thinking about scout programs, a lot of VC firms. So, you know, try to like, network or meet with VC is and ask them if they have a program like this, where ultimately give you money to invest. And then you get a portion of any anything that goes well, ultimately, at the end of the day, just as an investor in their in their fund would. And so that can be a really great way to start to kind of build a portfolio of sorts of investments without necessarily needing to have all that money yourself. And then from the founder entrepreneurs perspective, you know, it's it's kind of like, hiring, just as what I mentioned, like, really think through, you know, the composition of your cap table. And especially on the angel investor front, like have a goal for like the percentage of people from underrepresented backgrounds that you want to have as part of your round, and there are a lot of really great resources and programs to find angel investors. So the first program I actually participated in was first rounds angel track program. And so if you just Google first round angel track, they have a full list of anyone who's participated in their program. And I think they've actually made a really great effort to diversify who's participating in that program. So that's really great to find angel investors from diverse backgrounds. And then, of course, like, you know, reach out to people who may who you may not think of as angel investors as like their full time job, or even as part of what they do, and see if they're willing to take a bet on you and their company if what you're seeking is like their advice, or other skills that can be useful to you as you grow your company. Amazing. Okay, those are very practical and tangible. And you know, the first part of, hey, just start to reach out like your story about intercom intercom chat ticket to notion saying I'd love to invest in that working out. It's it's a little bit reminds me of your barbecue story of where you showed up to a barbecue, you start to chat with someone and now that led to something else. I mean, a little bit more deliberate than that. But it's the same sort of idea. It's like just asking good things could really happen or maybe they'll introduce you to somebody else or but it's the thread that can lead up to something really big. So many people make the ask and and you know, I'm shocked when when I even get asked sometimes of people and then and I respond and I was just like, wow, that person really had, you know, the guts to like reach out and like ask for something that they wanted. And, you know, I, I fully support that and, and want to encourage more people to do that. So, yeah, so I think more people should consider doing that when they're when they're trying to, you know, make an effort to get to know people to grow their network, to get advice, those kinds of things. Amazing, amazing. Okay, so we have five minutes left. And I have two questions I want to go through. And one, the one is, you know, you see the future, I think actually one of the best part about being an early stage investor is you see the future, you see things that will become big and mainstream, maybe eight, 10 years from now, because that's how long how long these companies take to become kind of household names, usually, sometimes shorter, but that's kind of the average length faster these days, but many years. And so you're seeing the seeds of what could become big and the next big stripe now. And so what are some sectors that you're really excited about or trends that you're seeing that you can share with with us in the audience? Sure. Yeah, I would say in terms of trends that I'm seeing, that I really enjoy and, and want to be part of as an investor, one would be, you know, ultimately, like tools for developers, specifically thinking about the developer as the customer, it was the thing that stripe focused on that really gave it that wedge in the early days. But I think there are a lot of things, a lot of industries out there where the developer is expected to be the, you know, integrator, the person who, who gets it done, but, you know, they're not actually the person who's making the decision on what software they use. So if you see a lot of products out there, which I think are taking off from the developers perspective, I think that's, that's really interesting. So a company I've invested in vantage, for example, is working on making costs for AWS more understandable. So, you know, it's kind of funny that like, often the finance person is like, hey, you really need to like, get your AWS costs down. But they're actually like no great tools for developer or the finance person to have to really understand how they can optimize those things. Or they come from Amazon, which is, you know, coming from the service providers themselves. And so I think that's a really interesting space when you start thinking about tools for developers to optimize costs, to grow the business, to not have to think about doing certain things. So another example of that would be something like WorkOS. So how can you build authentication and other facets of enterprise application, you know, without having to reinvent the wheel. So using their platform so that you as the developer can focus on your product rather than like building enterprise features, like those kinds of things are interesting. I think like data accessibility. So how do you actually understand your metrics within an organization? How can people understand data without having to know SQL within an organization? Like, I think there are a lot of companies in that space, which are really interesting. And then just like financial technology for consumers, I think, has still a long way to go, especially in other regions and outside of North America. You know, there aren't the Venmos and the Square Caches and some of the Robin Hoods of the world that we have here elsewhere. Those are all so great. And yeah, resonates. And I think those are really great insights. Thank you so much. Okay. So we have about a minute and a half left. And so one question that I like to ask everyone who comes on the show is, you know, as a woman in technology, where is the industry lived up to your expectations and where has it fallen short? Yeah, I would say first and foremost, you know, I've been really lucky to be part of organizations where I feel like if I show up and did good work, I was rewarded, either in the Stripe case with more work, so more equity, more compensation, and other things that came along with that. And that was something that, you know, I think, like, I respected that, ultimately, and was something that a lot of other companies, you have a more like, wait your turn, type of philosophy around giving people those opportunities and ways to grow. And then I would just say that I also recognize that I was in like a privileged position of being an early employee and one of like, relatively few women at a generational company, and that that's not the case for a lot of people. So I think I would love to see the experience that I had be the experience for a lot of other people out there. I agree. I agree. Because it's, it is when you have it, it's amazing. But then you read these stories, or hear stories of where it's not, and you're just like, that's just not okay. And so if you can make take some of the good experiences and make it more accessible to more people, I think then that would be we do way better off as an industry and a society and a city or wherever you're a community, it'd be very, that'd be a great step forward. I 100% agree. Christina, this was amazing. You're amazing. I loved everything. Thank you so much for joining. Thanks, everyone for tuning in to Yes, We Can. We'll be back next week. And Christina, you're an inspiration to all of us. Thank you. Thank you, Michelle.