The Exchanges

Q We are going to discuss Jira, but I do want to flip to the other side of the table, because that's the kind of challenging elements and the commonalities that those that struggle. In terms of those that succeed, why do those that succeed succeed? And what separates the good from the really great?

A Yeah. So I think in order to succeed in productivity and collaboration, because it's about the end user and it has a lot of commonalities with how consumer companies grow, you need a strong, well-liked brand. The quantitative version of that is you need an NPS of over 60. The other people who do really well are founders that have a great sense of PR and ability to generate earned media. We were huge beneficiaries at Slack of Stewart's, uh, the CEO and founder. Innate ability to just charm every reporter he ever met, as well as a lot of people on Wall Street. I think the other thing that really great companies have is strong expansion within their customers. Um, strong revenue growth in this sector really comes from expanding within customers you've captured, more so than just the top of funnel. And then great companies in this space will also have great engagement and continued paid use. What this looks like is that over 60% of your monthly active users should be daily active users. You should have a power user curve showing customers using the product every workday and net revenue retention of over 140%.

AI assessment note: “The quantitative version of that is you need an NPS of over 60.”

Q async, for sure, especially given my London roots. But I do want to ask, because, you know, you've seen the likes of Slack skyrocket like, you know, no company has done before in the collaboration tool space in many respects, and then there's always companies that fail. If we start on the actual challenging side, Why do collaboration startups fail, and are there commonalities and patterns in those that do?

A In my experience, the number one reason that collaboration companies fail is they have a poor go-to-market despite having a high-quality product. As a product person, this really emotionally pains me to see this happen, but people will spend years building something with very little input from customers and then be surprised when it doesn't take off in the market, even though it's something that they're really proud of. And the work is good. I think the next thing that I see is selling into managers instead of individual contributors. At the end of the day, it can be counterintuitive to approach it this way, but the end user is your customer, even if they're not the person who's taking out their credit card or filling out the invoice. There's a tendency to want to say, well, the manager is really my customer because it's the manager who has the credit card and I'm going to sell into them. But they have a lot of disincentives for rolling out new tooling and new processes, but they're highly incented to keep their team happy and staffed with the tools that the team already knows that they love.

AI assessment note: “the number one reason that collaboration companies fail is they have a poor go-to-market”

Q Can I ask, what does the internal technical stack look like for you in terms of, like, and I know it's really nitty gritty, but I'm too intrigued. Do you take notes on Evernote? Is it Rome Research? How do you bring in other How do you think about funnel progression and note taking in that evaluation phase?

A Oh, absolutely. So I'm a huge nerd and what my Canadian friends call a try hard, which is someone who's usually very overprepared and incredibly persnickety. And so I am a huge note taker from the very first time that I meet a founder and often before, especially if they've sent me the deck ahead of time. I read it. I have notes. I have questions. I'm there to dig in. Those notes become the basis for the deal doc in Google Docs. Then I create a channel in Slack that is, you know, company XYZ series A. I drop the post in there. I pin it. I get the deal team together. We go through those docs. Depending on the stage, obviously we'll use Excel. Less likely to use something like Google Sheets just because Excel is so powerful. And then we process that through really quickly, oftentimes on Slack in the deal channel, which has really sped up the process.

AI assessment note: “Those notes become the basis for the deal doc in Google Docs.”

Q We are going to discuss Jira, but I do want to flip to the other side of the table, because that's the kind of challenging elements and the commonalities that those that struggle. In terms of those that succeed, why do those that succeed succeed? And what separates the good from the really great?

A Yeah. So I think in order to succeed in productivity and collaboration, because it's about the end user and it has a lot of commonalities with how consumer companies grow, you need a strong, well-liked brand. The quantitative version of that is you need an NPS of over 60. The other people who do really well are founders that have a great sense of PR and ability to generate earned media. We were huge beneficiaries at Slack of Stewart's, uh, the CEO and founder. Innate ability to just charm every reporter he ever met, as well as a lot of people on Wall Street. I think the other thing that really great companies have is strong expansion within their customers. Um, strong revenue growth in this sector really comes from expanding within customers you've captured, more so than just the top of funnel. And then great companies in this space will also have great engagement and continued paid use. What this looks like is that over 60% of your monthly active users should be daily active users. You should have a power user curve showing customers using the product every workday and net revenue retention of over 140%.

AI assessment note: “in order to succeed in productivity and collaboration... you need a strong, well-liked brand.”

Q of mechanized onboarding in that way. Do you feel it is a category creation play in terms of how they really present their onboarding? And I guess, how do you think about that moving forward with companies that you meet? Because I tell so many companies every week, have you thought about doing superhuman for onboarding to really garner that kind of champion user? How do you think about it?

A Yeah. I think high touch onboarding experience, especially at seed and series a is a really great way to learn from and connect and actually develop a community of super fans, right? TBD, whether the unit economics of that work past that stage, but I believe in human touch and companies like Slack and superhuman are not only really active on Twitter and things like that, but have highly engaged high quality customer service too. And that is a really unsung competitive advantage. When you write into Slack or Superhuman, you get a response from a real human being who's really read your email, and oftentimes, and this was definitely the case internally at Slack, they've, you know, gone into the internal tool and looked at how you're using the product, and they understand what your role is on the team, and if you can even take this action that you're looking to change. And people move from being a zero or one NPS to being a nine or a 10 off of one human interaction, and that's It's unchangeable, because that's about human nature.

AI assessment note: “high touch onboarding experience, especially at seed and series a is a really great way”

Q We are going to discuss Jira, but I do want to flip to the other side of the table, because that's the kind of challenging elements and the commonalities that those that struggle. In terms of those that succeed, why do those that succeed succeed? And what separates the good from the really great?

A Yeah. So I think in order to succeed in productivity and collaboration, because it's about the end user and it has a lot of commonalities with how consumer companies grow, you need a strong, well-liked brand. The quantitative version of that is you need an NPS of over 60. The other people who do really well are founders that have a great sense of PR and ability to generate earned media. We were huge beneficiaries at Slack of Stewart's, uh, the CEO and founder. Innate ability to just charm every reporter he ever met, as well as a lot of people on Wall Street. I think the other thing that really great companies have is strong expansion within their customers. Um, strong revenue growth in this sector really comes from expanding within customers you've captured, more so than just the top of funnel. And then great companies in this space will also have great engagement and continued paid use. What this looks like is that over 60% of your monthly active users should be daily active users. You should have a power user curve showing customers using the product every workday and net revenue retention of over 140%.

AI assessment note: “in order to succeed in productivity and collaboration... you need a strong, well-liked brand”

Q Can I ask, what does the internal technical stack look like for you in terms of, like, and I know it's really nitty gritty, but I'm too intrigued. Do you take notes on Evernote? Is it Rome Research? How do you bring in other How do you think about funnel progression and note taking in that evaluation phase?

A Oh, absolutely. So I'm a huge nerd and what my Canadian friends call a try hard, which is someone who's usually very overprepared and incredibly persnickety. And so I am a huge note taker from the very first time that I meet a founder and often before, especially if they've sent me the deck ahead of time. I read it. I have notes. I have questions. I'm there to dig in. Those notes become the basis for the deal doc in Google Docs. Then I create a channel in Slack that is, you know, company XYZ series A. I drop the post in there. I pin it. I get the deal team together. We go through those docs. Depending on the stage, obviously we'll use Excel. Less likely to use something like Google Sheets just because Excel is so powerful. And then we process that through really quickly, oftentimes on Slack in the deal channel, which has really sped up the process.

AI assessment note: “Those notes become the basis for the deal doc in Google Docs.”

Q async, for sure, especially given my London roots. But I do want to ask, because, you know, you've seen the likes of Slack skyrocket like, you know, no company has done before in the collaboration tool space in many respects, and then there's always companies that fail. If we start on the actual challenging side, Why do collaboration startups fail, and are there commonalities and patterns in those that do?

A In my experience, the number one reason that collaboration companies fail is they have a poor go-to-market despite having a high-quality product. As a product person, this really emotionally pains me to see this happen, but people will spend years building something with very little input from customers and then be surprised when it doesn't take off in the market, even though it's something that they're really proud of. And the work is good. I think the next thing that I see is selling into managers instead of individual contributors. At the end of the day, it can be counterintuitive to approach it this way, but the end user is your customer, even if they're not the person who's taking out their credit card or filling out the invoice. There's a tendency to want to say, well, the manager is really my customer because it's the manager who has the credit card and I'm going to sell into them. But they have a lot of disincentives for rolling out new tooling and new processes, but they're highly incented to keep their team happy and staffed with the tools that the team already knows that they love.

AI assessment note: “the number one reason that collaboration companies fail is they have a poor go-to-market”

Q I totally agree. I mean, also Austin at Lambda lies in that. Speaking of that then, bluntly, would you advise founders to get good at Twitter? And for those that are considering, what would you advise them?

A Yeah, being good at Twitter is a competitive advantage, uh, even though it sounds kind of silly. So, you know, a lot of organic growth flows through the conversations taking place on Twitter, and that's largely because that early core customer of a collaboration startup is very likely to be someone who works in technology, is an early adopter, and is therefore Pretty online, right? They're reading about the latest software. They're keeping up with new companies. They're eager to try new technology. And so a lot of these ideas and conversations that end up becoming blog posts and podcasts and companies begin on Twitter first. So I don't know how many times I've seen this on Twitter, but someone, usually someone fairly prominent will get on Twitter annoyed with some problem that they have, right? Twitter is ultimately for complaining and say, what's the best tool for taking notes? And then this sort of, like, cycle kicks off, and super fans of all these products, you know, the cult members of these cults, will show up and overwhelmingly recommend their tool, and I know Superhuman, for instance, benefited a lot from that, and it looks lately like Rome Research is really benefiting from that as well.

AI assessment note: “Yeah, being good at Twitter is a competitive advantage, uh, even though it sounds”

Q Not at all, but I do want to kick off today with a little bit on you. So tell me, we've got some incredible years operating, but what was the moment that you realized venture was for you, and how did you come to be a partner at Lightspeed today?

A You know, I first learned about venture capital actually throughout the process of raising venture capital for the first time. I had a side project in college that I worked on for a year while finishing up, and I was working nights and weekends at my first job when a VC basically preempted our seed round by giving us a term sheet. So that opportunity really catalyzed my career. It's such a huge vote of confidence to have someone invest in you, and it majorly opened the aperture of the world to me to show me what was possible. So I ran that startup. It was a gaming company for a few years, and I raised a Series A even before going out of business after the recession. But Silicon Valley really rewards some types of failure. And I went on to have a great career as a game designer and then a product manager at a bunch of early stage companies before joining Slack early on in the first days of work of 2015. There I became the head of product and I started and ran the growth team in the effort to drive our daily active users from 500,000 to over six million in about three years. And then I decided to leave Slack after feeling like I'd really accomplished a lot of what I set out to do and I got approached by investors who remembered me from having pitched them over a decade before. People asked if I was interested in trying out venture capital, and it turns out if someone asks you som…

AI assessment note: “I decided to leave Slack... and I got approached by investors who remembered me”

Q Can I ask, what does the internal technical stack look like for you in terms of, like, and I know it's really nitty gritty, but I'm too intrigued. Do you take notes on Evernote? Is it Rome Research? How do you bring in other How do you think about funnel progression and note taking in that evaluation phase?

A Oh, absolutely. So I'm a huge nerd and what my Canadian friends call a try hard, which is someone who's usually very overprepared and incredibly persnickety. And so I am a huge note taker from the very first time that I meet a founder and often before, especially if they've sent me the deck ahead of time. I read it. I have notes. I have questions. I'm there to dig in. Those notes become the basis for the deal doc in Google Docs. Then I create a channel in Slack that is, you know, company XYZ series A. I drop the post in there. I pin it. I get the deal team together. We go through those docs. Depending on the stage, obviously we'll use Excel. Less likely to use something like Google Sheets just because Excel is so powerful. And then we process that through really quickly, oftentimes on Slack in the deal channel, which has really sped up the process.

AI assessment note: “Those notes become the basis for the deal doc in Google Docs.”

Q in terms of those fundamentals. I think one of the things I loved was in this conversation spawns from a tweet that you mentioned productizing this shit out of venture, but you said it was post having lost a deal. It happens to everyone. What does that post mortem look like for you? Post loss deal. And I think interesting, do you do it for every one deal as well?

A I probably should, but perversely, you really do learn more from failure than you do from success. But the best insights from creating the retrospective have come from the founders themselves. So even though they passed, oftentimes you really do get to know people throughout this process. And so far, every founder has been very gracious with me and given me feedback. That's been hugely helpful. The other thing I do in the retrospective is I list out the timeline of the deal process itself. What happened? When was the meeting? How much of the time of the founder's process did we end up being able to get alongside the sort of classic list of start doing this, stop doing this and keep doing this. And then I circulate it widely internally. I get the deal team who is closest to the deal to give me feedback. I call people for a back channel. I call the references. I, you know, do the often uncomfortable work, and it is uncomfortable because by the time you have everything together, the outcome seems obvious and totally unavoidable, right? But that's because you have new data and better feedback, and that's how you learn.

AI assessment note: “I list out the timeline of the deal process itself.”

Q but I'm going to just let you roll with it, and apologies for it being broad, but how do you see the future of collaboration? I think this is tacking on one for me, which is like, are we in a A bundling or an unbundling phase. I see the verticalization of SaaS collaboration tools, but then I see Notion. So what's the future, and are we bundling or unbundling?

A Just before COVID took hold, it seems like we might be heading back towards the bundled approach, as more tools were emerging that were all-in-one toolkits, right, similar to Notion. But now I think we might be shifting against that. We're living through this historic moment and the shift of how we work, and it felt like years ago, but it was actually weeks ago, that we were debating this A somewhat distant future of remote work, and suddenly here we are, everyone having arguably the worst new user experience possible for working remotely together, but we've sped up the world a few years in the space of weeks. So I think the companies that get started in the next years will be companies that wouldn't have been possible if not for this seismic shift. They're going to be responding to very new needs of an increasingly traumatized workforce. A bundle is a perfect product for customers with a stable, predictable set of needs. A business could reasonably expect to understand what those needs would be in the future and provide that functionality within a cohesive tool powered by one identity. But bundles are also brittle, and now every aspect of how we work and how businesses provide services to their customers is different, and it may be changed forever.

AI assessment note: “now I think we might be shifting against that.”

Q by doing it. So, totally agree, and makes me very happy to hear that. It is different, though. You mentioned that angel investing, and it's very different. So, I'd love to hear your thoughts, and actually, I spoke to Nicole before the episode, and she asked, given your operating background, and given the angel investing, what have been the biggest surprises for you since making the switch to venture full-time?

A Yeah, absolutely. The sheer volume of ideas... And concepts that people are building that you see as an institutional investor is just vast, right? And then as an angel investor, your deal flow will just come normally from people who you already know. So you might see the one company that's doing X, Y, Z, and then send it to someone and say, Hey, what do you think about this? And my experience was the institutional VCs that I knew would send me back an email saying, Oh yeah, I met with them last week. Here are their eight competitors that are also building other things that you should know about. And that really opened my eyes to just this absolute global scale of venture.

AI assessment note: “The sheer volume of ideas... And concepts that people are building”

Q We spoke about bundling versus unbundling there. The other, the big question kind of in the space is asynchronous or synchronous. It may not be as binary as choosing one can, but how do you think about the relationship between the two and where more potential lies in your mind?

A Yeah. You know, I think there's still a huge amount of potential in asynchronous workflows because they enable distributed decision-making and more autonomous teams. And here we are, everyone is on a distributed team and they need a lot of autonomy to be able to unblock and move on to the next part of their workday. But we also need synchronous time with other people to enrich our lives and also to develop and maintain empathy for each other. We're really social animals and we crave connecting with one another. But on the whole, I think the arc of the future of work bends toward asynchronicity. It enables people to work together across time zones and countries, and we're really a global workforce now.

AI assessment note: “on the whole, I think the arc of the future of work bends toward asynchronicity.”

Q by doing it. So, totally agree, and makes me very happy to hear that. It is different, though. You mentioned that angel investing, and it's very different. So, I'd love to hear your thoughts, and actually, I spoke to Nicole before the episode, and she asked, given your operating background, and given the angel investing, what have been the biggest surprises for you since making the switch to venture full-time?

A Yeah, absolutely. The sheer volume of ideas... And concepts that people are building that you see as an institutional investor is just vast, right? And then as an angel investor, your deal flow will just come normally from people who you already know. So you might see the one company that's doing X, Y, Z, and then send it to someone and say, Hey, what do you think about this? And my experience was the institutional VCs that I knew would send me back an email saying, Oh yeah, I met with them last week. Here are their eight competitors that are also building other things that you should know about. And that really opened my eyes to just this absolute global scale of venture.

AI assessment note: “The sheer volume of ideas... And concepts that people are building that you see”

Q We spoke about bundling versus unbundling there. The other, the big question kind of in the space is asynchronous or synchronous. It may not be as binary as choosing one can, but how do you think about the relationship between the two and where more potential lies in your mind?

A Yeah. You know, I think there's still a huge amount of potential in asynchronous workflows because they enable distributed decision-making and more autonomous teams. And here we are, everyone is on a distributed team and they need a lot of autonomy to be able to unblock and move on to the next part of their workday. But we also need synchronous time with other people to enrich our lives and also to develop and maintain empathy for each other. We're really social animals and we crave connecting with one another. But on the whole, I think the arc of the future of work bends toward asynchronicity. It enables people to work together across time zones and countries, and we're really a global workforce now.

AI assessment note: “I think there's still a huge amount of potential in asynchronous workflows”

Q and it's a perfect transition, so thank you for that one, but you spoke with my thoughts, Specifically about productizing venture and how it helps you serve the core customer being a founder. I spoke to Jeremy before the show and he said, Mercy is productizing the shit out of venture in delightful terms. So, uh, sounds great, but in reality, what elements of venture do you think need productizing?

A Yeah, so the core loop, right, that powers a startup is build, ship, and adapt. Companies live and die with their ability to execute just on that cycle. And what you're building, shipping, and adapting is your product, what you deliver to the customer. In venture, founders are customers, and the core loop is really similar. Evaluate, compete, and adapt. But when you're a VC, the product you're improving is really yourself and how you work with your firm. So your viewpoint on technology, your understanding of the market and society, your ability to win, the value you can bring to founders. When you deeply know a space, you can connect with founders and have early conviction because it's more like recognizing something. So that cycle of evaluate, compete, and adapt, making yourself smarter, faster, and better, Enables you to really be in that winning position from the get-go.

AI assessment note: “In venture, founders are customers, and the core loop is really similar. Evaluate, compete,”

Q in terms of those fundamentals. I think one of the things I loved was in this conversation spawns from a tweet that you mentioned productizing this shit out of venture, but you said it was post having lost a deal. It happens to everyone. What does that post mortem look like for you? Post loss deal. And I think interesting, do you do it for every one deal as well?

A I probably should, but perversely, you really do learn more from failure than you do from success. But the best insights from creating the retrospective have come from the founders themselves. So even though they passed, oftentimes you really do get to know people throughout this process. And so far, every founder has been very gracious with me and given me feedback. That's been hugely helpful. The other thing I do in the retrospective is I list out the timeline of the deal process itself. What happened? When was the meeting? How much of the time of the founder's process did we end up being able to get alongside the sort of classic list of start doing this, stop doing this and keep doing this. And then I circulate it widely internally. I get the deal team who is closest to the deal to give me feedback. I call people for a back channel. I call the references. I, you know, do the often uncomfortable work, and it is uncomfortable because by the time you have everything together, the outcome seems obvious and totally unavoidable, right? But that's because you have new data and better feedback, and that's how you learn.

AI assessment note: “The other thing I do in the retrospective is I list out the timeline”

Q but I'm going to just let you roll with it, and apologies for it being broad, but how do you see the future of collaboration? I think this is tacking on one for me, which is like, are we in a A bundling or an unbundling phase. I see the verticalization of SaaS collaboration tools, but then I see Notion. So what's the future, and are we bundling or unbundling?

A Just before COVID took hold, it seems like we might be heading back towards the bundled approach, as more tools were emerging that were all-in-one toolkits, right, similar to Notion. But now I think we might be shifting against that. We're living through this historic moment and the shift of how we work, and it felt like years ago, but it was actually weeks ago, that we were debating this A somewhat distant future of remote work, and suddenly here we are, everyone having arguably the worst new user experience possible for working remotely together, but we've sped up the world a few years in the space of weeks. So I think the companies that get started in the next years will be companies that wouldn't have been possible if not for this seismic shift. They're going to be responding to very new needs of an increasingly traumatized workforce. A bundle is a perfect product for customers with a stable, predictable set of needs. A business could reasonably expect to understand what those needs would be in the future and provide that functionality within a cohesive tool powered by one identity. But bundles are also brittle, and now every aspect of how we work and how businesses provide services to their customers is different, and it may be changed forever.

AI assessment note: “now I think we might be shifting against that”

Q in terms of those fundamentals. I think one of the things I loved was in this conversation spawns from a tweet that you mentioned productizing this shit out of venture, but you said it was post having lost a deal. It happens to everyone. What does that post mortem look like for you? Post loss deal. And I think interesting, do you do it for every one deal as well?

A I probably should, but perversely, you really do learn more from failure than you do from success. But the best insights from creating the retrospective have come from the founders themselves. So even though they passed, oftentimes you really do get to know people throughout this process. And so far, every founder has been very gracious with me and given me feedback. That's been hugely helpful. The other thing I do in the retrospective is I list out the timeline of the deal process itself. What happened? When was the meeting? How much of the time of the founder's process did we end up being able to get alongside the sort of classic list of start doing this, stop doing this and keep doing this. And then I circulate it widely internally. I get the deal team who is closest to the deal to give me feedback. I call people for a back channel. I call the references. I, you know, do the often uncomfortable work, and it is uncomfortable because by the time you have everything together, the outcome seems obvious and totally unavoidable, right? But that's because you have new data and better feedback, and that's how you learn.

AI assessment note: “I probably should, but perversely, you really do learn more from failure”

Q but I'm going to just let you roll with it, and apologies for it being broad, but how do you see the future of collaboration? I think this is tacking on one for me, which is like, are we in a A bundling or an unbundling phase. I see the verticalization of SaaS collaboration tools, but then I see Notion. So what's the future, and are we bundling or unbundling?

A Just before COVID took hold, it seems like we might be heading back towards the bundled approach, as more tools were emerging that were all-in-one toolkits, right, similar to Notion. But now I think we might be shifting against that. We're living through this historic moment and the shift of how we work, and it felt like years ago, but it was actually weeks ago, that we were debating this A somewhat distant future of remote work, and suddenly here we are, everyone having arguably the worst new user experience possible for working remotely together, but we've sped up the world a few years in the space of weeks. So I think the companies that get started in the next years will be companies that wouldn't have been possible if not for this seismic shift. They're going to be responding to very new needs of an increasingly traumatized workforce. A bundle is a perfect product for customers with a stable, predictable set of needs. A business could reasonably expect to understand what those needs would be in the future and provide that functionality within a cohesive tool powered by one identity. But bundles are also brittle, and now every aspect of how we work and how businesses provide services to their customers is different, and it may be changed forever.

AI assessment note: “heading back towards the bundled approach... But now I think we might be shifting against that.”

Q of mechanized onboarding in that way. Do you feel it is a category creation play in terms of how they really present their onboarding? And I guess, how do you think about that moving forward with companies that you meet? Because I tell so many companies every week, have you thought about doing superhuman for onboarding to really garner that kind of champion user? How do you think about it?

A Yeah. I think high touch onboarding experience, especially at seed and series a is a really great way to learn from and connect and actually develop a community of super fans, right? TBD, whether the unit economics of that work past that stage, but I believe in human touch and companies like Slack and superhuman are not only really active on Twitter and things like that, but have highly engaged high quality customer service too. And that is a really unsung competitive advantage. When you write into Slack or Superhuman, you get a response from a real human being who's really read your email, and oftentimes, and this was definitely the case internally at Slack, they've, you know, gone into the internal tool and looked at how you're using the product, and they understand what your role is on the team, and if you can even take this action that you're looking to change. And people move from being a zero or one NPS to being a nine or a 10 off of one human interaction, and that's It's unchangeable, because that's about human nature.

AI assessment note: “I think high touch onboarding experience, especially at seed and series a is a really”

Q We spoke about bundling versus unbundling there. The other, the big question kind of in the space is asynchronous or synchronous. It may not be as binary as choosing one can, but how do you think about the relationship between the two and where more potential lies in your mind?

A Yeah. You know, I think there's still a huge amount of potential in asynchronous workflows because they enable distributed decision-making and more autonomous teams. And here we are, everyone is on a distributed team and they need a lot of autonomy to be able to unblock and move on to the next part of their workday. But we also need synchronous time with other people to enrich our lives and also to develop and maintain empathy for each other. We're really social animals and we crave connecting with one another. But on the whole, I think the arc of the future of work bends toward asynchronicity. It enables people to work together across time zones and countries, and we're really a global workforce now.

AI assessment note: “I think there's still a huge amount of potential in asynchronous workflows”

Q async, for sure, especially given my London roots. But I do want to ask, because, you know, you've seen the likes of Slack skyrocket like, you know, no company has done before in the collaboration tool space in many respects, and then there's always companies that fail. If we start on the actual challenging side, Why do collaboration startups fail, and are there commonalities and patterns in those that do?

A In my experience, the number one reason that collaboration companies fail is they have a poor go-to-market despite having a high-quality product. As a product person, this really emotionally pains me to see this happen, but people will spend years building something with very little input from customers and then be surprised when it doesn't take off in the market, even though it's something that they're really proud of. And the work is good. I think the next thing that I see is selling into managers instead of individual contributors. At the end of the day, it can be counterintuitive to approach it this way, but the end user is your customer, even if they're not the person who's taking out their credit card or filling out the invoice. There's a tendency to want to say, well, the manager is really my customer because it's the manager who has the credit card and I'm going to sell into them. But they have a lot of disincentives for rolling out new tooling and new processes, but they're highly incented to keep their team happy and staffed with the tools that the team already knows that they love.

AI assessment note: “the number one reason that collaboration companies fail is they have a poor go-to-market”

Q by doing it. So, totally agree, and makes me very happy to hear that. It is different, though. You mentioned that angel investing, and it's very different. So, I'd love to hear your thoughts, and actually, I spoke to Nicole before the episode, and she asked, given your operating background, and given the angel investing, what have been the biggest surprises for you since making the switch to venture full-time?

A Yeah, absolutely. The sheer volume of ideas... And concepts that people are building that you see as an institutional investor is just vast, right? And then as an angel investor, your deal flow will just come normally from people who you already know. So you might see the one company that's doing X, Y, Z, and then send it to someone and say, Hey, what do you think about this? And my experience was the institutional VCs that I knew would send me back an email saying, Oh yeah, I met with them last week. Here are their eight competitors that are also building other things that you should know about. And that really opened my eyes to just this absolute global scale of venture.

AI assessment note: “The sheer volume of ideas... that you see as an institutional investor is just vast”

Q Not at all, but I do want to kick off today with a little bit on you. So tell me, we've got some incredible years operating, but what was the moment that you realized venture was for you, and how did you come to be a partner at Lightspeed today?

A You know, I first learned about venture capital actually throughout the process of raising venture capital for the first time. I had a side project in college that I worked on for a year while finishing up, and I was working nights and weekends at my first job when a VC basically preempted our seed round by giving us a term sheet. So that opportunity really catalyzed my career. It's such a huge vote of confidence to have someone invest in you, and it majorly opened the aperture of the world to me to show me what was possible. So I ran that startup. It was a gaming company for a few years, and I raised a Series A even before going out of business after the recession. But Silicon Valley really rewards some types of failure. And I went on to have a great career as a game designer and then a product manager at a bunch of early stage companies before joining Slack early on in the first days of work of 2015. There I became the head of product and I started and ran the growth team in the effort to drive our daily active users from 500,000 to over six million in about three years. And then I decided to leave Slack after feeling like I'd really accomplished a lot of what I set out to do and I got approached by investors who remembered me from having pitched them over a decade before. People asked if I was interested in trying out venture capital, and it turns out if someone asks you som…

AI assessment note: “I got approached by investors who remembered me from having pitched them over a decade”

Q of mechanized onboarding in that way. Do you feel it is a category creation play in terms of how they really present their onboarding? And I guess, how do you think about that moving forward with companies that you meet? Because I tell so many companies every week, have you thought about doing superhuman for onboarding to really garner that kind of champion user? How do you think about it?

A Yeah. I think high touch onboarding experience, especially at seed and series a is a really great way to learn from and connect and actually develop a community of super fans, right? TBD, whether the unit economics of that work past that stage, but I believe in human touch and companies like Slack and superhuman are not only really active on Twitter and things like that, but have highly engaged high quality customer service too. And that is a really unsung competitive advantage. When you write into Slack or Superhuman, you get a response from a real human being who's really read your email, and oftentimes, and this was definitely the case internally at Slack, they've, you know, gone into the internal tool and looked at how you're using the product, and they understand what your role is on the team, and if you can even take this action that you're looking to change. And people move from being a zero or one NPS to being a nine or a 10 off of one human interaction, and that's It's unchangeable, because that's about human nature.

AI assessment note: “I think high touch onboarding experience, especially at seed and series a is a really great way”

Q I totally agree. I mean, also Austin at Lambda lies in that. Speaking of that then, bluntly, would you advise founders to get good at Twitter? And for those that are considering, what would you advise them?

A Yeah, being good at Twitter is a competitive advantage, uh, even though it sounds kind of silly. So, you know, a lot of organic growth flows through the conversations taking place on Twitter, and that's largely because that early core customer of a collaboration startup is very likely to be someone who works in technology, is an early adopter, and is therefore Pretty online, right? They're reading about the latest software. They're keeping up with new companies. They're eager to try new technology. And so a lot of these ideas and conversations that end up becoming blog posts and podcasts and companies begin on Twitter first. So I don't know how many times I've seen this on Twitter, but someone, usually someone fairly prominent will get on Twitter annoyed with some problem that they have, right? Twitter is ultimately for complaining and say, what's the best tool for taking notes? And then this sort of, like, cycle kicks off, and super fans of all these products, you know, the cult members of these cults, will show up and overwhelmingly recommend their tool, and I know Superhuman, for instance, benefited a lot from that, and it looks lately like Rome Research is really benefiting from that as well.

AI assessment note: “Yeah, being good at Twitter is a competitive advantage”

Q I totally agree. I mean, also Austin at Lambda lies in that. Speaking of that then, bluntly, would you advise founders to get good at Twitter? And for those that are considering, what would you advise them?

A Yeah, being good at Twitter is a competitive advantage, uh, even though it sounds kind of silly. So, you know, a lot of organic growth flows through the conversations taking place on Twitter, and that's largely because that early core customer of a collaboration startup is very likely to be someone who works in technology, is an early adopter, and is therefore Pretty online, right? They're reading about the latest software. They're keeping up with new companies. They're eager to try new technology. And so a lot of these ideas and conversations that end up becoming blog posts and podcasts and companies begin on Twitter first. So I don't know how many times I've seen this on Twitter, but someone, usually someone fairly prominent will get on Twitter annoyed with some problem that they have, right? Twitter is ultimately for complaining and say, what's the best tool for taking notes? And then this sort of, like, cycle kicks off, and super fans of all these products, you know, the cult members of these cults, will show up and overwhelmingly recommend their tool, and I know Superhuman, for instance, benefited a lot from that, and it looks lately like Rome Research is really benefiting from that as well.

AI assessment note: “Yeah, being good at Twitter is a competitive advantage, uh, even though it sounds kind of silly.”