Yes We Can

Hi, everyone. Welcome back to this week's episode of Yes We Can. I'm so excited to have Ann Bordetsky on the show today. Hi, Ann. Hi, Michelle. It's great to be back. I know. Well, this is why, I mean, I'm excited for all my guests, but Ann, this is extra sweet for me because Ann was the very first person who agreed to come on Yes We Can a year ago when we started this during the pandemic. And so I loved our initial conversation a year ago and the fact that you're back, so much has changed. We have so many things to cover. So thank you again for spending 30 minutes with me and the audience today, Ann. Oh, my gosh. I'm so excited to be back. And anytime that I get an excuse to hang out with Michelle, of course, I'm going to take it. So yeah, I'm thrilled to be back and I think you started a wonderful tradition here. That's great. It's good. Well, actually, I have a fun montage video of all the conversations from last year that are going to come out this week, as of which you're part of and 25 other amazing women. So for the listeners of the audience, that's coming out this week. So that's really fun to kind of see it all together. But so, Ann, what's interesting last year, obviously, the pandemic has happened and a lot has happened in the world. But for you personally, a lot has happened. When you were last on the show, we spent the half an hour talking about being an operator and building all these amazing companies and how you think about impact. And now you've gone to the other side of the table and operating reins. And now you're on the venture side. You've joined NEA as a venture partner. NEA is an amazing venture partner, a venture capitalist firm. They're actually, we're an investor in Cloudflare way back in the day. Scott Sandell sits on our board and you're an adventure partner there. So how how are things going? It's been amazing. So I'm a partner in NEA. Quick, quick, quick fix there. But yeah, I was in an interesting last year, mid pandemic, mid all the chaos that the world had to offer for us as professionals and parents and all of those things. I actually came to this very natural kind of transition point in my own career where I was deciding between kind of going into venture versus continuing in an operating role. And I always just I love so much to work with founders. I think venture is one of the most interesting kind of, honestly, jobs that you can have in the world. And after seeing so many different tech companies in different sectors kind of go through their life cycle, some successes, some failures, for sure, you kind of develop this real appreciation for just how hard it is, but how interesting it is to try to build a new category defining company, what it takes to do that. So for me, going into venture was in some ways just a different way to kind of serve founders and work with founders. As an operator, I always thought of it as, you know, I'm still working in service of founders, I'm helping them to realize their vision to build their company, etc. As an investor, obviously, you also have to pick the right companies. But I think you do have that kind of long term relationship with entrepreneurs helping them to really construct their companies and make them successful. And so they're two very different kind of professions. But but there's a lot of things about operating that really translate into venture as well. So, so far, so good. It's a wild time in venture, as we all know, there's a lot of activity, it's moving a million miles an hour. There's a lot of venture firms, a lot of startups right now. So it's as dynamic as it could possibly be. But since I've always wanted to be like at the scene of the action, I'm having the best time right now. That's good. That's great. I mean, I mean, when we when we spoke a year ago, you I mean, you were an operator at the better place, you Twitter Uber, I mean, amazing companies, people have heard of you've been part of the teams making it happen. And I know you said in service of the founder, but really, and you were building you were those companies were successful because people like you were on the team. And so it really takes takes a village to make these companies. It's now it's true. Like if I'm being totally honest, I joined each of those companies to realize the vision. And that's the amazing thing for startups. Like if you have a really interesting vision for how you want to change the world, and the kind of impact that you want to create, like, you will get amazing people to come join you. You really will, because people have a shared interest in being like, Oh, my God, I have to see this through. I want to make be part of it making it happen, which is how I fell in love with technology, actually, because there's so much building and being involved. And it really is, you see the what you put in you, you see the ownership of what comes up. So one of the things I want to ask you, because you're an operator for a long time, now you're in venture fairly, you know, one year in, and I've always thought, and I've never been a venture capitalist. So one of the things I always thought was, well, you get to see the future, because you see things so early. I mean, like in your role, are you're seeing things very early in their life cycle, of which you almost get to your daydream about, oh, my God, if this becomes successful, you kind of get a snow globe of what the what the future can look like. Does that does that resonate with you? Or am I totally off basis? No, no, it does. It does. And it's truly like one of the best parts of being in venture. It's the thing that gives you gives me anyway, so much, like jet energy and like, I don't know, in enthusiasm day to day is, you know, your days are kind of filled with most days are filled with just, you know, back to back meetings with founders, and each founder, and I'm looking at companies that are really early stage, right? So things that are kind of embryonic, just forming, maybe just an idea, right, precede seed stage companies all the way to kind of series B, series C, where, you know, you've got some momentum, and you're really trying to figure out how to build a company from there, but it's still very early across the board. And it is truly inspiring to go through entire days where what you're taking in is sort of somebody's passion for a particular problem, right? They're kind of unique insights into the world around us how technology can solve that problem. And you know, you get a real appreciation for like, the incredible breadth and diversity of thought that is represented in founders and entrepreneurs, so many different walks of life, so many different passion points, so many different ways that people want to apply their talents. And yeah, they're like, they are by definition of what they're doing, especially when they're pitching a VC, right? They are so optimistic for the impact that they can have with a change that they can create, like it makes you more optimistic about the future. And I think the hardest part for me, actually, you know, so far, you know, in my career I'm generally an optimist, too. So I naturally root for every single founder that I meet with, unless something's really off. And then I have to kind of coach myself back into a more kind of analytical, you know, VC mindset of like, you know, what's wrong with this idea? Like, how can this fail? How can this? And I'm not saying VCs are only about that, but you do have to go through that exercise. You know, you're kind of, your job is to have that kind of investor judgment about what can really scale and become massive versus what's just a nice idea. And, but the human factor of it is really, really rewarding in the short term, while you're kind of building up your investor track record and figuring out how to do it. I love this. Well, this point is one that I don't, I think that if you've worked in venture, or maybe if you've been a founder pitching venture capitalists, it's a little bit more obvious, but this is a point that I don't think is said enough where, I mean, you, you find more reasons not to invest in a company, right, than to find reasons. So like, just give the audience a sense of when you say you're meeting with these early stage entrepreneurs, these visionaries, this early forming stage companies, like how many meetings a week or different sort of unique companies are you meeting in the course of a week or day or week or month? And then how many investments are you making kind of as a ratio, just to give the audience a sense of, it's really hard to get a yes. Yeah. Oh my gosh, that's such a good question. So I don't know if I'm representative of other VCs, haven't figured that out yet. And I'm still early. And so I think there's a drinking from a fire hose nature to kind of getting started, but, you know, I will probably meet, you know, four to five companies, you know, three days out of the week, like Tuesday through Thursday. So, you know, some weeks I'm meeting, you know, definitely with 10 or more companies that week could be more, could be less just depending on kind of the cadence. And it's kind of the worst, I think when like a few great companies kind of hit at the same time and they just, they don't know it, right. But they're kind of competing for the same, you know, attention time that week. And in general, you know, an individual investor or partner like myself only makes a few investments per year, right. And so you're seeing hundreds of companies probably, right. If you, if you keep your aperture pretty wide and you want to know the landscape and you're, you know, maybe investing in two or three companies per year. And so you are looking for those literal and figurative unicorns that, you know, it's the right idea, the right time, the right team, kind of the right approach to that opportunity and also the right chemistry with that founding team so that you actually choose to work together. I mean, that's just, and again, back to you being an optimist and wanting and falling in love with all these ideas and entrepreneurs are visionary. They're usually very passionate about what they're trying to solve. You're like, oh my God, I love this, but probably not right for me at this time. I wasn't, has that been hard over the last year? It's, it's, it's a new learning curve to figure out like when, when I'm not in a position to invest for whatever reason, like, you know, what can I do to still help that founder? Because I'm rooting for them. There's probably some way that I can truly add value with a connection or something else. You can't really do that for everyone because you'll never do your day job if you're spending your time on that. But I do try to really like for the people that I'm rooting for, where I think that the company really has a lot of potential to do something in service of that founder or team, whether it's feedback or connection or an introduction, that's going to help them on their journey because, you know, I'm not just about getting deals done. That's a very short-term mindset. Like I want to cultivate great founders in this ecosystem because maybe it's not this round, maybe it's the next one, maybe it's not this company, maybe it's another company they'll do. And I think part of what we have to do in venture having, frankly, the access and the resources and the networks that we have is for those new founders who are coming in who may not be as connected, who may not be insiders, like help them, help them kind of, you know, realize what their potential. And so anyway, I try to do that, but still kind of manage my own time and energy on that. That's amazing. You know, as somebody who was not an insider, when we showed up in Silicon Valley, Matthew Lee and I, that goes a long way. So thank you for bringing it forward because that's, I think, the beauty of technology or the Valley, or now maybe Miami, is you can show up and not be an insider, have a meeting, an introduction to somebody like Ann, and all of a sudden your life changes in some way. You all of a sudden are shipping what you thought what you set out to do, which is pretty cool. Yeah. That's good. So let's say there's some entrepreneurs listening and they're like, oh my God, Ann sounds so great. So can you talk a little bit about some of the areas you're really excited about and that you're focused on? And then if an entrepreneur is listening and they have an idea that they think is just like such a great fit for you, Ann, how do they become one of those 10 people you're meeting potentially any given week? How do you decide who to spend time with at the top of the funnel? Great, great question. Let me see if I can break this down. So in terms of things that I'm interested in, investable areas, right now I'm very focused on, I would say probably three areas. One is future of work, which we're all living and co-creating together right now. But I do think, especially as a former COO and operator, I think companies need new products, new solutions to help them design for distributed work, whether that's hiring remote, distributed workforce, managing that. There's employee experience, employee communication. There's just a lot that we need to evolve to create kind of a virtual first workplace environment across different industries, not just tech. And so I'm very interested in folks who are solving that problem. Also looking at consumer tech and really the future of how we connect and communicate, because I think culturally we're in this pendulum swing really away from social media, like away from that really kind of like personal celebrity. People are seeking out more intimacy, authentic connection, ways to build professional networks online. So I think if you're building an Instagram killer or a LinkedIn killer, I'd love to talk to you. Let me know. And I think the third area, which is really, it's more like a theme versus, because it's such a big part of our world going forward. But I personally have a real passion for sustainability and climate solutions. I've worked in that space in the past. So I'm definitely paying attention to what's happening in climate tech, in software, in marketplaces, in kind of data-driven solutions for the space. And I'm interested in that too. So if you're seed to kind of series B founder, that's my sweet spot. And then I really love founders who are prepared. What do you mean by that? I think we're in this environment where there is a lot of capital and there is a lot of interest for founders, but I still think you're going to match make to your best fit investor, the best partner for you, if you really come in prepared, right? You know, your space really well, you have a really tight kind of pitch and deck that you can share. You're generous with that information versus trying to be all coy about it. So that investors actually have enough data to kind of grapple with what problem you're solving, how you're solving it. You're not, you're not gonna, you know, I think get any advantage by like withholding data, which I feel like is becoming more popular. And then, you know, when you have that 30 minute window, like really make the most of it, sell where you're going versus where you've been. If you have that opportunity, don't focus on like everything you've done up to that point. That should be like 5% of your pitch focus on where you're going, how you're going to get there and how you're going to bring the right people along to help you execute. And so when I see that manifested in a cold email or a warm introduction through a shared connection, or, you know, even a Twitter DM, I've definitely responded to Twitter DMs, not every single one, but, you know, quite a few, like, then I want to talk to you. If you show me that you're prepared and you're ready to engage, like most of the time I'll make the time to have an initial meeting, try to understand and whether or not I'm the right investor, like point you in the right direction. I love that. I love that. You know, it's so interesting that you talked about, there's so many things you talked about, you just said that I just want to double click on. And so one is this idea of, I don't know if you saw this when you were an operator where people want to talk about kind of the history lesson of where they got to. I'm like, let's, let's, let's put the history lesson aside and talk about where we're going, what we need to do to get there. And so it's interesting. You see that with founders, they want to talk about kind of what they've done so far and the progress they made versus here's what we're working on and why is it important and how, how we're doing so far. You see that also. It's like, you want to kind of get credit for the work that you've done. I think where it's, where it comes from and you're so close to it. Like you want to be understood and seen for the work that you've done. But the reality is like an investor is investing in you for what you can create going forward, really investing in your future state versus, you know, how far you've come. And so it's kind of a mental shift to focus on that, but it's very much like pitching execs, right. Or pitching in a board meeting, an exec meeting where like, please don't tell me the history of this project. Like what is the decision to be made? What is the critical information I need to make this decision? And then we shall move on. Right. Like there's that discipline, right. That's required. Yeah. No, but that resonates with me and my operating role. So thanks for sharing that. Okay. So these three areas, the future of work, which we could spend a whole episode just talking about that. We could spend many episodes just talking about future of work, the consumer tech angle, and then the climate and sustainability, which is something that definitely came up a year ago, but how you're so passionate. It's such an important topic. Have you made investments in any of these areas? And can you talk about any of the companies you've invested in with me and the audience? I have. So I made two investments. I would say in Q1 of this year, I'm working on another one right now. I can't share two of them, but one of them I can share one that I am very excited about. Hopefully I can talk about the rest in a future episode, but on this theme of kind of future of work, I think there's a lot of different pain points in there for companies, but one is, and we were just chatting about this before we got started, but it's really like, how do we, in this distributed virtual first kind of Zoom first world, how do we actually make meaningful connections at work? How do we create a sense of shared context among employees? How do we communicate more effectively? How do we create more information liquidity, I would say, in the workplace? And how do we give, I think, employees intuitive communication formats that they already know from their consumer world that can help us in the workplace as we kind of start to build, frankly, and craft and cultivate more of our relationships virtually. So the company is called Spoken, and you should check them out. If you're running a company or if you're an operator, check them out. But they're making it really easy for companies to bring podcasting and essentially audio into the workplace, right? So you could do a CEO update, right, that rather than, you know, sitting and watching on a Zoom, your employees could be taking a walk, right, or taking their kids to school and still kind of tuning in to kind of critical company information. So, and companies are coming up with all kinds of creative ways to use it to do, you know, fun things, peer-to -peer kind of fireside chats, or delivering learning and development content. So Spoken is one that I'm excited to work with. And then I would say the others are kind of more thematically focused on robotics and automation for kind of very difficult jobs that, frankly, in this, you know, probably should be automated. And, you know, other companies that I'm looking at that are really focused on kind of creator economy and kind of this idea of independent work where you're crafting your own career, multiple revenue streams, and really thinking about your job as a portfolio of services that you provide. That's so Spoken. Is it asynchronous kind of audio where you don't have to be tuning in at the exact same time? Or it could be both synchronous or asynchronous. So it could be something that's recorded and then you replay back when you're on your walk or dropping your kids off to school or when you want. Yeah, that's great. There feels like audio is kind of this next frontier of having more of a relationship, feeling like, you know, the person that has not been cracked yet. And so Spoken, all right, well, we've heard it here firsthand. Thank you for sharing that with the audience. Again, you see the future. So one day, 10 years from now, Spoken can be this huge company. All I can say is like, we're all walking around with AirPods in our ears. Like, what else can we do with that? So that, you know, I'm loving this, but I think we all get a bit of Zoom fatigue and want to be able to step away from our screens. And, you know, I think audio is asynchronous audio can really kind of liberate employees to stay connected without sitting on a screen all day. Yes, yeah, definitely. That's great. That's good. And so how did you meet that? So just going back to how you met the founders of Spoken, how are you just curious back to, was it, were they one of the Twitter DMs or was it a warm introduction? Or did you know them from a prior role? Actually, none of the above. So they were an incredible team that went through Y Combinator in the winter batch. Okay. And so I did not know them previously, but I think that Fozzie and Marielle, the two co-founders, they really kind of represent, you know, what I think a lot of successful founding teams are kind of made of. They have real like passion and commitment to the space. They hustle, they work super fast. They have this incredible kind of like learning curve mindset of, you know, you learn what you don't know and you just keep going, keep going, keep up leveling yourself as founders. And so I really believe in their ability to kind of execute in this space. And I love seeing that from founders, like just because you came from a fancy company, which some of us do, doesn't, it actually doesn't guarantee anything. Like it's the work that you do in building the company that matters. So I love to back sort of teams that are really strong hustle and execution and just leaning into the problem. It's amazing. You know, this, this, this, this point you made about like learning quick learning cycles, that's something that's come up so much with the last year with every person I've had on the show, it comes up. It's like, you might not know anything on day one, but just start learning. And all of a sudden you become the expert and the rate at which you learning is such an asset. It has come up so many times the last year. And I think that's a really good metaphor for finding, learning more about technology. Cause it is a fairly new industry. It's becoming more and more like important and bigger and part of every, but every industry. And so if you don't know very much today, you don't have to lean out. You can lean in and just start to learn. And pretty soon three months in, you're like, wow, I know a lot more than when I started. I'm going to be the expert on something. If you just focus on it. Exactly. But I you know, I, it's something that I really look for in, in hiring when I was an operator, like looking for people who have that steep learning curve and can put themselves on a steep learning curve, because if you're in a fast growing company, things change so quickly, right? Like you have to be able to evolve with the company and the job changing and the team growing and all the, you know, and so I look for that thread line of personal growth and, and I look for the same thing in founders because your company, you know, if you're kind of on the right track, like your company is changing every couple months. Right. And so you have to change with the company and kind of stay ahead of the curve. And frankly, the founders that do right, they get to run their companies for a long time. I love that. I love that. Okay. So we have, we have about seven more minutes and we have a couple more topics I wanted to cover. So the first is what's been the biggest surprise going from an operating role. You've done a great job talking about what it's on the investment side. I know it's new, but I'm just curious, has there been something that's surprised you a lot over the last year that maybe you could share with the audience? Well, I think, you know, there's obviously some differences in sort of what your energy goes to, you know, day to day. I think one of the enlightening things has been to see, I mean, I would say the nature of the beast is that you do have to say no to a lot of companies to say yes to a few. But there are all these things that are outside, I would say, of the founder's control that do impact, you know, the level of interest that a company could get or whether or not they get funded or who the right matches. And I'm not sure I ever really understood how much like these very subtle little things can come into play to decide who, you know, who gets funded and who doesn't. And, you know, it's things like, but I think you see this more when you're on the venture side. It's, for example, like, you know, if you're a founder and you're kind of you see yourself as the top dog in a category, which is great, like you have to compete in your category, you know, you have competition to worry about. But from the venture side of the table, like, you're not just competing with kind of companies in your space, you know, investors are seeing companies across many different categories, right? So you have to be the company that sort of stands apart from other top companies in their categories, if that makes sense, right? And then, you know, I think there's just timing. Timing is always a big factor, like who's available that week, how many other deals are coming through, right? And so there's lots of like nuanced little things that come into play, like who gets traction at that moment in time or not. And I think that can either make you pessimistic or optimistic, depending on how, you know, your outlook on life. I think what I would say to founders is, you know, you're not getting traction at what point in time doesn't mean you couldn't get traction later, because you're not seeing kind of what's happening for that firm, or that team or that individual, right? You don't really have visibility into that. You're just kind of raising when you're raising. And, you know, I still think that there's, you know, kind of biases, right, that are historical to a particular category. They, you know, everyone is coming at it with some sort of like preconceived notions of what makes that, you know, a unicorn company or not. And so I, it's, it's, there are many, many different variables in the equation of how the venture industry works, and what it sort of prioritizes. And I do think it takes real, like, internal conviction, and vision, and some sort of mental independence, I think, from the rest of the ecosystem to truly, like, make the right judgment calls, because there is a bit of a herd mentality. And some of that is for good reason. And some of that is just, it is what it is just a herd mentality. And so observing all of that from the inside is really, really fascinating. But I would say, you know, the thing that probably the other big surprise has been, because we all kind of, you know, we sort of judge what venture is based on VC Twitter. So VC Twitter, just so everyone knows, is like a tiny slice of the venture community. And I think everyone would be shocked if they saw how many like, humble, hardworking, kind, high integrity, amazing humans are part of this industry today that you do not see if all you see is what's happening on Twitter. And that has been like the most amazing, wonderful, not total surprise, but it just makes the job better to know, like, you know, there's a lot of like, humble, behind the scenes, awesome people that, you know, are just doing really, really good work. They're just not self promoting on it. And that's definitely there. And you want to find those people. You do. That's amazing. I, you know, as somebody who has only been on the operating side, but I've raised a lot of venture capital in my career. Those are all actually really good, unique insights for me, too. So thanks for sharing that. So we have about two minutes left. So the first is, you know, one of the things and since you're so interested in the future of work and distributed teams, what do you think about this idea of talent no longer having to move to power centers like San Francisco? And again, being able to I mean, I joked about Miami earlier, but I'm only joking. I mean, the mayor has done an amazing job since December, really recruiting people. I'm just curious, what's your point of view on that for the audience? I think it's a long time coming, right? Like, I think this is such a necessary change. And what I mean by that is, you know, what we have historically thought of as Silicon Valley, right? And greater San Francisco Bay Area, this is not an affordable place to live. Like, this is not a place where all talent tech talent in the world can possibly co -locate. And so I think that, you know, overall, like SF and Silicon Valley as a tech ecosystem, it's not going anywhere. There's just a super high concentration of talent and energy and shared culture here that will maintain this as an epicenter. But I think the fact that remote work, whether you're just working remotely as an individual, and you're working for one of the bigger tech companies, or if you're looking to start a company, like, it is incredibly healthy and good for tech in the long run that there's other cities where people can now effectively start a company, recruit talent, you know, frankly, have an affordable lifestyle. Because, you know, it is it takes, you know, I think the the high cost of living and the high cost of office space and starting a company is one of the things that creates barriers to entrepreneurship. So I'm actually very interested to see what happens when there are more affordable places in which people can start companies, right, and recruit talent. But I think there's something magical, there's a shared culture and intensity that exists here, maybe also exists in some form in New York that doesn't quite exist in other cities. That, you know, I think it's great that we have those other options. But I feel like this is still, you know, there's going to be a lot of activity that stays here. Amazing. We're gonna leave it on that this magical, the magical being anyway, and it was wonderful. Congratulations. We'll definitely have you back to hear about your future investments. And Verdesky, yes, we can. Thanks so much for being on today, Anne.