The Exchanges

Q Yeah, no, I'm totally with you. I do want to finish it on probably the most important, the most recent publicly announced investment, and why did you say yes and get so excited?

A Yeah, I invested in a company called Workstream, which is building a The HR platform for the frontline workforce of America, and I really love this space because even though I'm a big fan of Workday, older platforms really struggle to build products for the deskless workforce, which is now almost kind of 2.8 billion people worldwide, so a massive market, and there's just enormous potential to build for mobile workflow and to really cater a product towards people that frankly don't sit on their desks and need a very different product to operate. And the founder there, it was one of those, like, quintessential valley moments where within 10 minutes of meeting him, I knew I wanted to invest in him. His name is Desmond Lim, and he has just this incredible mix of empathy and grit.

AI assessment note: “I invested in a company called Workstream, which is building a The HR platform”

Q like, you know, I have a portfolio company that I'm on the board of, and the founder's just like, I get like 10 analysts a day. Which ones do I say yes to? Which ones do I say no to? How do I manage this? What would you advise your founders in terms of speaking to non-partners and the analysts of the world, and just being a little bit disciplined?

A Yeah, so you're absolutely right. It's changed a lot. When I was an analyst, there were very few young people, as, as I mentioned before, and now there's, there are a lot. What I always tell my founders is, you should reply, and then you should get them to do work for you. It's very easy to send an email to an entrepreneur, but when they reply, you And they ask you to do something. I think that's when you can really shine both as an individual analyst, but also show your firm's worth. And so tactically, what does that work mean? It means great. Tell me what you think about my space. Like, why are you excited about my product in particular when there is ABC competitor out there, or I'm really struggling to find a head of engineering and I would love your support, or I noticed that you have XYZ customer in your portfolio. We've been dying to get an introduction, and so you're not wasting your time because you're getting them to do work for you, work that you would have to do, and then you're actually seeing, well, now they've gotten in the door. Can they actually help me, and is this a sign of what is to come with a partnership with this firm?

AI assessment note: “What I always tell my founders is, you should reply, and then you should get them to do work”

Q much. I seem to have a huge amount of energy suddenly, so this is perfect timing, but I want to start with a little bit on you. So tell me, it's such a weird world, but it's also wonderful in so many ways. How did you make your way into the world of venture, and what did that entry point look like for you, and now being GP at CRV?

A Sure. So when I graduated from Stanford, I honestly had no idea what venture was. Today, every senior at Stanford knows what a VC is, but back then it wasn't really an industry that was accessible to young people. So I began my career like any type A student, and spent some time in finance at Goldman Sachs and Morgan Stanley, and then as a chief of staff to the CEO at a mobile advertising startup, right when the mobile ad ecosystem was And I loved a lot about both those experiences, but neither felt a hundred percent right. And then one night I got an email from one of those college email lists that you forget to unsubscribe from after you graduate about a role at Bessemer. And the more I learned about the role and about venture, it was like the finance and the startup ecosystem having a baby. So it was a lot of good elements from both those industries that I had had experience in and Coming together in one role, which I then quickly fell in love with, and I spent six great years at Bessemer, where I sourced companies like Intercom and New Voice Media for the firm, and worked with some incredible founders at SendGrid, Zylo, Adaptive Insights, and Intact. Then I joined CRV as a general partner a little less than a year ago, still focused on all things software.

AI assessment note: “one night I got an email... about a role at Bessemer”

Q role of analysts in venture, and PG said before, only speak to partners in VC firms. I have to say, and I'm probably going to get shot down on Twitter for this, so I probably shouldn't say it, but I do agree with him. So how do you feel, am I totally wrong, and are analysts important in venture for founders to speak to and meet and spend time with?

A Yeah, so this is something I'm very passionate about, and I have to give the caveat that I'm very biased as a former analyst myself, but I think they are so incredibly critical to the venture ecosystem. What I like to say is that people don't realize that most partners are busy with ten-plus board companies. They're busy with LP fundraising and internal fund management and all the politics that come with that, and they say they're still meeting new companies, but the reality is it's a very small portion of their time. And they depend on their analysts or junior investors to be the feet on the ground. So people think the analyst is the gatekeeper, but I say take it one step forward. They are the gatekeeper, yes, but they're also going to be your fiercest advocate. And in my kind of seven to eight years in venture, some of our best deals would have never gotten done had an analyst not pounded the table and made the argument on behalf of the entrepreneur. And great examples of that, like real companies, Intercom, which I sourced, Twitch, Procore, and I can go on and on, and these are multi-billion dollar exits or valuations.

AI assessment note: “I think they are so incredibly critical to the venture ecosystem.”

Q much. I seem to have a huge amount of energy suddenly, so this is perfect timing, but I want to start with a little bit on you. So tell me, it's such a weird world, but it's also wonderful in so many ways. How did you make your way into the world of venture, and what did that entry point look like for you, and now being GP at CRV?

A Sure. So when I graduated from Stanford, I honestly had no idea what venture was. Today, every senior at Stanford knows what a VC is, but back then it wasn't really an industry that was accessible to young people. So I began my career like any type A student, and spent some time in finance at Goldman Sachs and Morgan Stanley, and then as a chief of staff to the CEO at a mobile advertising startup, right when the mobile ad ecosystem was And I loved a lot about both those experiences, but neither felt a hundred percent right. And then one night I got an email from one of those college email lists that you forget to unsubscribe from after you graduate about a role at Bessemer. And the more I learned about the role and about venture, it was like the finance and the startup ecosystem having a baby. So it was a lot of good elements from both those industries that I had had experience in and Coming together in one role, which I then quickly fell in love with, and I spent six great years at Bessemer, where I sourced companies like Intercom and New Voice Media for the firm, and worked with some incredible founders at SendGrid, Zylo, Adaptive Insights, and Intact. Then I joined CRV as a general partner a little less than a year ago, still focused on all things software.

AI assessment note: “one night I got an email from one of those college email lists”

Q like, you know, I have a portfolio company that I'm on the board of, and the founder's just like, I get like 10 analysts a day. Which ones do I say yes to? Which ones do I say no to? How do I manage this? What would you advise your founders in terms of speaking to non-partners and the analysts of the world, and just being a little bit disciplined?

A Yeah, so you're absolutely right. It's changed a lot. When I was an analyst, there were very few young people, as, as I mentioned before, and now there's, there are a lot. What I always tell my founders is, you should reply, and then you should get them to do work for you. It's very easy to send an email to an entrepreneur, but when they reply, you And they ask you to do something. I think that's when you can really shine both as an individual analyst, but also show your firm's worth. And so tactically, what does that work mean? It means great. Tell me what you think about my space. Like, why are you excited about my product in particular when there is ABC competitor out there, or I'm really struggling to find a head of engineering and I would love your support, or I noticed that you have XYZ customer in your portfolio. We've been dying to get an introduction, and so you're not wasting your time because you're getting them to do work for you, work that you would have to do, and then you're actually seeing, well, now they've gotten in the door. Can they actually help me, and is this a sign of what is to come with a partnership with this firm?

AI assessment note: “you should reply, and then you should get them to do work for you.”

Q a, uh, it was actually Ansaf. I put a little birdie in the schedule before, but it was Ansaf, so you can blame him for this one. And he said your role models are much more aligned to media than tech and business, which I thought was super interesting. So why is that, and how do you think about this and them being relevant to your work now, I guess?

A The role models that I think he was referring to in media, like an Oprah or a Christiane Amanpour, what I like about them is more about how they ask questions and how they get to the truth earlier than anyone else, and also how when you have a conversation with them, even for an hour, you think you've known them for years, and that's a true quality, and unfortunately, I see that less and less in venture, because I think it's become So commoditized, where within five minutes, we're asking about the ARR, and the net dollar retention, and the growth rate, and few people really take time to ask the questions like, why are you building this? You could do anything in the world. Why this? Or where did you come from? Or who are you? And I think at the end of the day, we're really just investing in people, and we have to know them before we invest in them, and I think These particular women that I look up to do that better than anyone else, and I like to emulate that in how I build relationships with entrepreneurs.

AI assessment note: “I like to emulate that in how I build relationships with entrepreneurs.”

Q role of analysts in venture, and PG said before, only speak to partners in VC firms. I have to say, and I'm probably going to get shot down on Twitter for this, so I probably shouldn't say it, but I do agree with him. So how do you feel, am I totally wrong, and are analysts important in venture for founders to speak to and meet and spend time with?

A Yeah, so this is something I'm very passionate about, and I have to give the caveat that I'm very biased as a former analyst myself, but I think they are so incredibly critical to the venture ecosystem. What I like to say is that people don't realize that most partners are busy with ten-plus board companies. They're busy with LP fundraising and internal fund management and all the politics that come with that, and they say they're still meeting new companies, but the reality is it's a very small portion of their time. And they depend on their analysts or junior investors to be the feet on the ground. So people think the analyst is the gatekeeper, but I say take it one step forward. They are the gatekeeper, yes, but they're also going to be your fiercest advocate. And in my kind of seven to eight years in venture, some of our best deals would have never gotten done had an analyst not pounded the table and made the argument on behalf of the entrepreneur. And great examples of that, like real companies, Intercom, which I sourced, Twitch, Procore, and I can go on and on, and these are multi-billion dollar exits or valuations.

AI assessment note: “they are so incredibly critical to the venture ecosystem”

Q Okay, so when we think then back to your time at best, And kind of the many lessons that you learned there. Such an incredible team. But, you know, when you think back to that time, what were the biggest lessons that you learned? And I guess, what did you learn about people as well?

A I learned more about venture as an analyst than I did in any other role that I've had, and I've had a lot of roles. You know, I've been analyst, associate, senior associate, vice president, and now GP, and I think it boils down to three things. The first is never forget that sourcing is still the heart of venture investing. Getting to a founder and Earlier than anyone else is how you succeed, and a lot of partners forget that because once you reach that level, you sort of think sourcing is below you, and I would just say it's the heart of the job, so never stop doing it and always make time to do it. The second thing I'd say is first impressions matter. Don't have a throwaway conversation. Don't send a one-line email. I still remember the first email that I sent Owen. At intercom. And I talked about why I liked his product, why I wanted to meet him, why Bessemer would be the right fit. And so much has happened since that email. It's such an incredible company, but every time we talk, he still remembers that email. And so it matters what I said and how I said it and that I believed in him way back when. So first impressions matter. That's the second point. And then the last thing I'd say about people, and I love that question because no one's ever asked me that. I think it says a lot about you as a founder in how you treat an analyst when they first email you. If I look back at …

AI assessment note: “I think it boils down to three things. The first is never forget”

Q title, so thanks for that, Anna. That's wonderful. Tell me, I spoke to, obviously, your husband, Ansnaf, before the show, and he mentioned, in particular, you're growing up in a 21 person household in Pakistan and moving to the U.S. at 17. Talk to me about that. How do you think that time in Pakistan and moving to the U.S., such a big move, how did it impact your mindset?

A Growing up outside of the U.S. gives you a lot of perspective. When I look back, I'm actually really proud to be an immigrant and proud of the values and the grit that it instilled in me at a young age. And to give you context, I lived through a military coup. I lived through a former prime minister getting assassinated. And so when you live in Pakistan, you kind of don't have time to worry about the incredibly privileged things we can worry about here in Silicon Valley. So when I moved here, I just learned don't take Anything for granted. And all that being said, you know, it was a very volatile country, but my childhood was incredible. I had a lot of support and encouragement from my parents and some amazing high school teachers that I still very vividly remember. But outside of that bubble, I honestly couldn't dream of having the career that I have in the US today. So I feel very lucky and grateful to be in this position. On the size of my household, It's true. I grew up in a very large family, which was very close and tight-knit, and yes, it was 21 people, and it wasn't even 21 people that lived close together. It was 21 people under one roof. It was my grandmother, who's the head of the household, four uncles and aunts, 11 cousins, 12 including me, and we did everything together from schoolwork to dinner to birthday parties. You know, we didn't even have to invite, like, o…

AI assessment note: “proud of the values and the grit that it instilled in me at a young age”

Q which I love too. But it was something that you said before the show that honestly, I have the opposite perception. So I'd love to have this debate with you. And you said very few firms are doing real early stage investing. I guess maybe it's nomenclature, but like what is real early stage investing to you then? And like, why are very few firms doing it in your mind?

A Yeah, so obviously there are some fantastic multi-stage firms, but by default, if you are a multi-stage firm, you have to spend time doing early, mid, and late-stage investing, and the more capital you raise, the more incentive you have to not exclude yourselves from future rounds and competitive companies by doing deals too early, but when you're a fund, and I'll give you, I'll give you some examples, obviously CRV is one, but there are others like USV, And benchmark when you intentionally limit your fund size and you're focused hundred percent on doing just that. So we have to, because of the parameters we've put around our fund size and around our strategy, we have to make the right calls at the A because we're likely not going to do the series D or the E. And through that, what I've seen is that we seem to form much closer bonds and connections with our founders. Because going back to the point I made about Owen and Intercom, it's really hard to forget the person that bet on you when no one knew your name or used your product, and I think that is sort of that secret weapon that early stage funds can use because they come out of it with a much deeper and much more emotional connection with the founder that I think multi-stage firms kind of struggle to form.

AI assessment note: “when you intentionally limit your fund size and you're focused hundred percent on doing just that”

Q mine that I need to work on. But anyway, in such an environment, like, how do you, with the round compression in terms of timelines, how do you try and judge The right timing of whether to lean in on a deal and like aggressively preempt, which is what most people are doing these days, or wait and just be diligent, do your work. How do you judge that timing?

A Yeah, it's very hard, especially now after COVID, the supply of good companies has decreased, and the best companies frankly aren't going through a formal fundraising process, so you have to spend time building real relationships. I think when to know whether to lean in or stretch in valuation has everything to do with your belief in a founder and a market. If you spend time on a market and see strong precedent there for meaningful exits, I wouldn't wait. I would stretch on valuation, make it a deal that is hard for the entrepreneur to say no to, especially at the early stage, because the more late stage you go, the more difficult I think it gets to underwrite to a larger number, because then that public market ceiling comes out of the blue.

AI assessment note: “when to know whether to lean in or stretch in valuation has everything to do with”

Q with. It's about price optimization. If you take in a multi-stage fund at seed, they are not incented to price you up at the A because they're already in and they've got their ownership. If you come in at the A, you're incented and aligned to get the best B possible rather than just grow ownership and push down the pre. That's what I say. How do you advise founders?

A I really like that framework because I've seen it play out. For me, the answer is really simple. I just tell my founders it's like a basic economic principle, which is opportunity cost. You always have the chance of working with the multi-stage fund down the line, and they really excel at the C's and the D's, but you don't with the early stage fund, and they are almost much more aligned with your incentives as an early stage founder. They think like the founder seat versus the The late stage investors who you can work with down the line if you outperform and they'd be happy to price your growth round, but it's just a very different kind of relationship and skill set that an early stage fund brings.

AI assessment note: “I just tell my founders it's like a basic economic principle, which is opportunity cost.”

Q want to go for it, and so do you want to make the investment? It's just more competitive than ever, and I especially feel this as a younger partner, like, how do you think about going against the heavyweights of industry, your Marc Andreessen's, your Peter Thiel's, when they come out to play? How do you think about going against them in such competitive environments, and what's worked for you?

A Yeah, you know, I can't sit here and tell you that winning is easy. It's still really tough going against the heavyweights In the industry. But I think there are a lot of ways you can put up a good fight and sometimes when spending more time with the entrepreneur is one of the main ways, because as I mentioned in sort of our analyst conversation, partners are really busy and they have made a commitment to 10, 12, sometimes 15 other entrepreneurs that they have long-term relationships with. They can't just drop all of that and focus on kind of the new entrepreneur they want to win over. Whereas A partner that is earlier in their career, they have maybe 20% of that load, and so spending more time, whether it's meals or phone conversations or customer intros, I think that goes a really long way, and then I think just being up front with the entrepreneur, because the entrepreneur, they are also an underdog just like you, and so saying my success is so aligned with yours in a way that It might not be for the twenty-year VC veteran. If you build a phenomenal company and you're part of my portfolio, we will both be successful. And that clicks with entrepreneurs in a way that would surprise you. And then I think the last thing that has really worked for me is just always showing up with more information and saying, I may have only eight years of venture experience, but I know your spac…

AI assessment note: “spending more time with the entrepreneur is one of the main ways”

Q title, so thanks for that, Anna. That's wonderful. Tell me, I spoke to, obviously, your husband, Ansnaf, before the show, and he mentioned, in particular, you're growing up in a 21 person household in Pakistan and moving to the U.S. at 17. Talk to me about that. How do you think that time in Pakistan and moving to the U.S., such a big move, how did it impact your mindset?

A Growing up outside of the U.S. gives you a lot of perspective. When I look back, I'm actually really proud to be an immigrant and proud of the values and the grit that it instilled in me at a young age. And to give you context, I lived through a military coup. I lived through a former prime minister getting assassinated. And so when you live in Pakistan, you kind of don't have time to worry about the incredibly privileged things we can worry about here in Silicon Valley. So when I moved here, I just learned don't take Anything for granted. And all that being said, you know, it was a very volatile country, but my childhood was incredible. I had a lot of support and encouragement from my parents and some amazing high school teachers that I still very vividly remember. But outside of that bubble, I honestly couldn't dream of having the career that I have in the US today. So I feel very lucky and grateful to be in this position. On the size of my household, It's true. I grew up in a very large family, which was very close and tight-knit, and yes, it was 21 people, and it wasn't even 21 people that lived close together. It was 21 people under one roof. It was my grandmother, who's the head of the household, four uncles and aunts, 11 cousins, 12 including me, and we did everything together from schoolwork to dinner to birthday parties. You know, we didn't even have to invite, like, o…

AI assessment note: “proud of the values and the grit that it instilled in me at a young age.”

Q mine that I need to work on. But anyway, in such an environment, like, how do you, with the round compression in terms of timelines, how do you try and judge The right timing of whether to lean in on a deal and like aggressively preempt, which is what most people are doing these days, or wait and just be diligent, do your work. How do you judge that timing?

A Yeah, it's very hard, especially now after COVID, the supply of good companies has decreased, and the best companies frankly aren't going through a formal fundraising process, so you have to spend time building real relationships. I think when to know whether to lean in or stretch in valuation has everything to do with your belief in a founder and a market. If you spend time on a market and see strong precedent there for meaningful exits, I wouldn't wait. I would stretch on valuation, make it a deal that is hard for the entrepreneur to say no to, especially at the early stage, because the more late stage you go, the more difficult I think it gets to underwrite to a larger number, because then that public market ceiling comes out of the blue.

AI assessment note: “has everything to do with your belief in a founder and a market.”

Q off Is when you see, like, the story adventure firms, and the newsletter comes out, and it's like, hey, we've added five female associates. Check out how awesome we are in our diversity. Partnership stays the same. Is that fair of me? Are they actually trying to nurture the next generation? I'm just being too glib, and they're doing their best, and how do you feel when you see this?

A It's very fair. It annoys me, too, but when I started in venture, we didn't even have that. I was the only woman at the firm for For half a year until we started hiring more, and now it looks very different, which makes me really happy, but you're absolutely right. They're not getting pulled up to the partner ranks. They're not making the key investment decisions or fund decisions, and what I like to say is women still get promoted for results while men get promoted for potential, and that's what We need to change. The women in venture that have been successful, there's a deal that they sourced that made a lot of money for the firm, or a deal that they led, or a deal that they pushed for that got them where they are, while men, if there's potential there, they're worthy of a shot, and I just like us to give more shots to women in the same way.

AI assessment note: “It's very fair. It annoys me, too”

Q But tell me, how does the decision making differ when comparing CRV to Bessemer? Both incredible firms, but differently.

A When I joined CRV, I had a feeling it would be very different, but it was even more different than I imagined. You know, at CRV, because we focus so much more on the early stage, and because our team is so much smaller, our conversations are almost more salon-like. We really dig into more of the philosophical and future-oriented dynamics of a company, and we talk a lot about the team. And at Bessemer, we did a little bit of that, but At Bessemer, we were the ones that came up with metrics on how to measure great cloud companies when no one knew how to measure cloud growth, and so as a result, we gravitated a lot more to that than really focusing on kind of team or the early signs in the market.

AI assessment note: “at CRV... our conversations are almost more salon-like... at Bessemer, we gravitated a lot more to that”

Q with nothing to do. Tell me, I want to move down the funnel a little bit though. So now we've kind of focused on like finding and sourcing. If we think about picking, some would say the most important, some would not. I'm interested to hear your thoughts. Like how have you seen your investment decision-making process change over the nine years you've been in venture and how's it evolved?

A One of the reasons I was really excited to join CRV is that they have this Laser focus on early stage investing, which is not just driven by data because there is no data, but it's much more a belief in teams. We like to call it founder market fit, but also in products. Do we think this product is right for this evolution of technology in 2020? Or what do we think is the right product that workers will need in 2025? And earlier in my career, I was much more data-driven, but I think what's really evolved over this time is my ability to take a leap of faith based on early signs, whether that's chatter about a product, whether it's a founder that spent time in the industry that he's trying to change, and not just ARR and net dollar retention.

AI assessment note: “what's really evolved over this time is my ability to take a leap of faith”

Q with. It's about price optimization. If you take in a multi-stage fund at seed, they are not incented to price you up at the A because they're already in and they've got their ownership. If you come in at the A, you're incented and aligned to get the best B possible rather than just grow ownership and push down the pre. That's what I say. How do you advise founders?

A I really like that framework because I've seen it play out. For me, the answer is really simple. I just tell my founders it's like a basic economic principle, which is opportunity cost. You always have the chance of working with the multi-stage fund down the line, and they really excel at the C's and the D's, but you don't with the early stage fund, and they are almost much more aligned with your incentives as an early stage founder. They think like the founder seat versus the The late stage investors who you can work with down the line if you outperform and they'd be happy to price your growth round, but it's just a very different kind of relationship and skill set that an early stage fund brings.

AI assessment note: “I just tell my founders it's like a basic economic principle, which is opportunity cost.”

Q think that's such a good way of framing it, actually. I do want to ask, okay, so if we're thinking about kind of giving more shots to female partners, I totally agree with you, But if you're advising this firm that's like five white male GPs, and they really wanted to actually change the way that they operate, how would you advise them other than just like hire female partners?

A Yeah, so I'd change it in all ways. You have to focus on the bottom, the top, and your portfolio, and I think that's what we're trying to do at LaunchX is just give women access and also demystify what this crazy VC black box is all about, and so If I became a consultant to a venture firm, I would tell them the following. The first I'd say is start a program or work with LaunchX to teach very high potential female entrepreneurs who are raising their first round of institutional financing about what it takes to raise a great round. Tell them the difference between a seed stage firm and a multi-stage firm. Tell them how they should pitch you because no one's told them. They don't have droves and droves of Male CEO friends or male VCs that will pass on that information to them. So do that education and access work. Secondly, hire great female analysts and associates. You, after hiring them, will realize that you will see more female CEOs pitch you, because through hiring these analysts, you are getting access to networks that you just have no access to. I'd say you probably know one or two female GPs, Call them and ask them who they really admire, whose work that they've been impressed by, that are either VPs or principals, and have a chat with them. Ask them the areas that they're focused on, ask them the companies that they've sourced, and talk about bringing them on at the part…

AI assessment note: “You have to focus on the bottom, the top, and your portfolio”

Q of the funnel, being so crucial, always there. When you think there's different ways, obviously you can do thesis driven, you can do network driven. When you think about how you go about it, how do you think about the aim at it? And what advice would you give with regards to really, I guess, developing your network if you choose that as the kind of front of funnel distribution?

A Yeah. So I have a little bit of a contrarian viewpoint and all my kind of venture friends make fun of me because I believe this, but I think that hanging out with other VCs as fun as it is, is It's antithetical to good sourcing. If we're very honest, the only deals you pass on to other VCs are deals that you don't want to do, especially if you're collaborating with firms that invest at the same stage. And I think, and what's worked for me is a much better use of time than happy hours is spending time getting to know a small group. And I really struggled with this because you have to find a group that is a really good fit. And so I have one of Female VCs that I'm really grateful for, and the best part is we got to know each other when we were analysts and associates, and we've kind of grown in our careers together, which has been really helpful to talk through everything, whether that's the sourcing funnel, whether it's internal fund dynamics. So I'd say, you know, if you're starting out, you don't have to go to every networking event. It's just people talking about the same thing that everyone else is talking about. It's not going to differentiate you. Get to know a really small group that you connect with and that you have kind of openness with. And then where else I find deals? For me, kind of hanging out with product or engineering leaders is time much better spent because t…

AI assessment note: “hanging out with other VCs as fun as it is, is It's antithetical to good sourcing”

Q educating female CEOs about the fundraising process and all the Turbulent twists and turns that it involved. I guess the thing that I wanted to touch on first is like so many people I've interviewed go, oh, Harry, you know, lack of female partners in venture is a pipeline problem. How do you think about this? And why do you think that there are so much fewer women in venture?

A Yeah, this is a very hot topic for me. And anytime someone says a pipeline problem, it actually makes me angry. I think pipeline is a lazy crutch. I think the reality is it's only a pipeline problem if you believe the best VCs have to be technical, which if you look at the Midas list is not the case at all. And yes, there is data that women are getting fewer technical degrees than men, but it does not translate to VC. People come from, as you heard from my background, like people come from very different backgrounds and experiences, and it's not directly correlated with success at all. You haven't tried hard to find Incredible women, and the fact that your network is limited to men is also the reason that they haven't worked with incredible women founders or female partners in the past. Pipeline is just a very lazy crutch of people that don't think it's valuable enough to work hard to bring women into the fold.

AI assessment note: “I think pipeline is a lazy crutch.”

Q with nothing to do. Tell me, I want to move down the funnel a little bit though. So now we've kind of focused on like finding and sourcing. If we think about picking, some would say the most important, some would not. I'm interested to hear your thoughts. Like how have you seen your investment decision-making process change over the nine years you've been in venture and how's it evolved?

A One of the reasons I was really excited to join CRV is that they have this Laser focus on early stage investing, which is not just driven by data because there is no data, but it's much more a belief in teams. We like to call it founder market fit, but also in products. Do we think this product is right for this evolution of technology in 2020? Or what do we think is the right product that workers will need in 2025? And earlier in my career, I was much more data-driven, but I think what's really evolved over this time is my ability to take a leap of faith based on early signs, whether that's chatter about a product, whether it's a founder that spent time in the industry that he's trying to change, and not just ARR and net dollar retention.

AI assessment note: “earlier in my career, I was much more data-driven, but I think what's really evolved”

Q Listen, I have such a man crush on Byron. I even told him, actually, after our first episode, I think he was a little bit surprised by that. Tell me, what do you believe the most around you disbelieve?

A That operators don't make good VCs. That's what I believe. I think it's really tough to have two CEOs in the boardroom. I think CEOs, when things work well for them, they're so used to repeating that, and sometimes it can work for another founder, but it's often a different company at a End up repeating some of the same mistakes you did as a CEO, and I have this fundamental belief that if you want to be a good investor, nothing can make you a good investor other than just doing that more. It's sort of that 10,000 hours concept, and I always think VCs should be sounding boards and, and not the leader of the company, and if they are the leader of the company, that's a problem.

AI assessment note: “That operators don't make good VCs. That's what I believe.”

Q which I love too. But it was something that you said before the show that honestly, I have the opposite perception. So I'd love to have this debate with you. And you said very few firms are doing real early stage investing. I guess maybe it's nomenclature, but like what is real early stage investing to you then? And like, why are very few firms doing it in your mind?

A Yeah, so obviously there are some fantastic multi-stage firms, but by default, if you are a multi-stage firm, you have to spend time doing early, mid, and late-stage investing, and the more capital you raise, the more incentive you have to not exclude yourselves from future rounds and competitive companies by doing deals too early, but when you're a fund, and I'll give you, I'll give you some examples, obviously CRV is one, but there are others like USV, And benchmark when you intentionally limit your fund size and you're focused hundred percent on doing just that. So we have to, because of the parameters we've put around our fund size and around our strategy, we have to make the right calls at the A because we're likely not going to do the series D or the E. And through that, what I've seen is that we seem to form much closer bonds and connections with our founders. Because going back to the point I made about Owen and Intercom, it's really hard to forget the person that bet on you when no one knew your name or used your product, and I think that is sort of that secret weapon that early stage funds can use because they come out of it with a much deeper and much more emotional connection with the founder that I think multi-stage firms kind of struggle to form.

AI assessment note: “when you intentionally limit your fund size and you're focused hundred percent on doing just that.”