The Exchanges

Q about this moving forward? And I always have to admit, I always say do remote or don't do remote. The worst is when you do remote plus HQ because people feel left out. It creates kind of a lack of synchronicity. I'm intrigued. You've done remote plus HQ since you were just eight employees. So I guess Why am I wrong, and what are the benefits of remote plus HQ?

A Fundamentally, we want to work with the most talented people wherever they are, and geolocation tends to be the predominant limiting factor. So I feel, and we, like Vinay Shaheed and I, feel very fortunate to have been guided to this conclusion of a hybrid company by our users. When we were five people in an SF office slash apartment, We ran a survey that found that 80% of our professional power users were using it to communicate with folks that they weren't sitting right next to, aka remote communication. So we knew that we had to dog food that, and the next five hires we made were all remote, and we persisted that fifty-fifty split ever since. Now, remote communication is the most complex, so you default to those rules of engagement for everyone, regardless of HQ or remote, which is why we have remote first as one of our five cultural values. First, you have to default to asynchronous communication. Slack messages, looms, documents. Be very intentional about the time that you spend live together. And related to number one, you have to document everything by default. You record every meeting, you document your decisions, and if you do those two things right, of default to async and document everything by default, you have second order effects. You have a more resilient organization. If somebody leaves or is out On vacation, you have the information you need to keep things movi…

AI assessment note: “we want to work with the most talented people wherever they are”

Q I guess kind of taking the logical next step though, then obviously Andrew from Coya came in, and I spoke to Andrew before the show, and he said, ask about the Series B, ask how it went down, and specifically what did the Sequoia B team do to try and win and close the deal?

A So Andrew Reid was an intro from Dylan Field of Figma, one of our early angels, And Andrew and I built the relationship over the course of nine months. At one of our coffee meetings, he told me, I know this is weird logic, but bear with me. I'm getting married in October, and I'd just really like to lead your Series B before I leave for the wedding and honeymoon. And we told him that, and I told him that we didn't think we were going to be fundraising for another couple quarters, but, you know, we'll pull a deck together and see what progress we've made. And he After a couple turns of feedback on the deck, Andrew asked me to meet him for a drink, and I thought that this was just to spend a little bit more time in a casual manner, which most of our meetings up until that point had been coffee meetings during the day or in the loom office, and so I thought it was just kind of like a little bit of casual hangout. When we were about to leave, he was like, oh, I also have this for you, and it was a term sheet that he put on the table, and the even more casual leave behind Was when we were walking out, we were like, high-fiving, like, doing the hug thing. He was also like, oh, and one more thing. And he sent an email that had 20 Sequoia partners and team members, including Rulof, Doug Leone, Michael Morwitz, who all recorded a Loom talking about why they were so excited to join Loom …

AI assessment note: “he sent an email that had 20 Sequoia partners and team members”

Q one aspect of multiple data points to collect. We've spoken about the investors there, and I do want to discuss fundraising itself, because when we chatted before, you mentioned the words to me, highly inefficient, mistrust laden, and overhaul when it comes to kind of the more matter of fundraising itself. Walk me through your thinking here. What are your thoughts on this, and how do you think about that?

A So, I'll take a few steps back here, because hearing mistrust-laden out loud is a little bit more negative and harsh than I thought when I originally wrote it, but I stick with the highly inefficient part. We kept hearing over and over again when we were raising our most recent round that was co-led by Sequoia and Code Two that we're calling our Series B+, is that We're not quite sure we can make an investment with a company and team we haven't met in person. And it goes without thinking now a few months on that we're all kind of in this COVID territory is that this is antiquated thinking. The fundraise industry was very quickly and radically forced to change their operating procedures because some firms were willing to take that leap to make the investment during early COVID without meeting in person, and they won deals as a result. So The inefficient part for me doing it in person was running, literally running sometimes from VC office to VC office for a couple weeks, which is a ton of work and overhead. And for those that haven't done a fundraise process, it sounds prestigious and fun, but it's really, it's a slog. And so this most recent fundraise was my favorite for a couple reasons. One, it was all over video conferencing. So there was no time between meetings trying to squeeze in emails or messages from From a phone, I got a meaningful amount of non-fundraised work done …

AI assessment note: “I stick with the highly inefficient part.”

Q not on schedule, but, you know, we're both quite young, and a question that I'm thinking about more and more is I've joined my first boards over the last 18 months, and I fundamentally want to be the best and most impactful board member that I can What advice would you give me from the founder's perspective of what I can be to be the best board member to you?

A Yeah, it's a really good question. And I think about the early investors that we were able to bring on and also how that's kind of scaled out to our board members in Ilya and Andrew. I've found that the best board members just very simply ask the best questions. They obviously have opinions about where it is that the company should go. But they don't mandate solutions. They don't mandate their thinking because the thing is that founders and operators are the ones who are doing the day-to-day work. So if you don't fundamentally believe in a path forward, then it's going to be hard for you to kind of get that conviction and execute on it. So Ilya and Andrew and early investors have helped us see around corners in so many different ways over the years. But what I've found universally to be true is that When they ask me a series of questions, when we have a true dialogue with each other, and we come to the same conclusion from there, we're able to get significantly more momentum in the short term versus here's the solution, go execute against it. And then you kind of loop back around maybe one or two weeks later, and you're like, eh, I'm not quite sure I'm still aligned on this front. So it fundamentally boils down to just ask really high quality questions.

AI assessment note: “I've found that the best board members just very simply ask the best questions.”

Q about this moving forward? And I always have to admit, I always say do remote or don't do remote. The worst is when you do remote plus HQ because people feel left out. It creates kind of a lack of synchronicity. I'm intrigued. You've done remote plus HQ since you were just eight employees. So I guess Why am I wrong, and what are the benefits of remote plus HQ?

A Fundamentally, we want to work with the most talented people wherever they are, and geolocation tends to be the predominant limiting factor. So I feel, and we, like Vinay Shaheed and I, feel very fortunate to have been guided to this conclusion of a hybrid company by our users. When we were five people in an SF office slash apartment, We ran a survey that found that 80% of our professional power users were using it to communicate with folks that they weren't sitting right next to, aka remote communication. So we knew that we had to dog food that, and the next five hires we made were all remote, and we persisted that fifty-fifty split ever since. Now, remote communication is the most complex, so you default to those rules of engagement for everyone, regardless of HQ or remote, which is why we have remote first as one of our five cultural values. First, you have to default to asynchronous communication. Slack messages, looms, documents. Be very intentional about the time that you spend live together. And related to number one, you have to document everything by default. You record every meeting, you document your decisions, and if you do those two things right, of default to async and document everything by default, you have second order effects. You have a more resilient organization. If somebody leaves or is out On vacation, you have the information you need to keep things movi…

AI assessment note: “we want to work with the most talented people wherever they are”

Q Are we going to build a big company today? Do you think that's a very different one that needs to be in person, and it's actually at the later stages when, ironically, more money's at stake, you can go off with video only. I'm intrigued, like, does it change then, and do you not feel as a founder you want to see the whites of my eyes to trust me?

A It's a great question, and I do believe that video is, specifically, like, video conferencing is an incredibly powerful way to get to know somebody if you are structured with your time together. So, One thing that I actually really enjoyed with Code Two and their onboarding process, this happened after the fundraise, is that we did a dinner together, and it was over the course of two, two and a half hours. There were partners that came in and out of the video call, but what we did for one part of it was we actually went through that New York Times, like, 36 questions to fall in love, and we asked these really deep and meaningful questions of each other, To get to know the individual, and I felt like even though I still haven't officially met Matt Mazzeo or Lucas Swisher of Cote Two in person, um, I feel like I know them at a pretty intimate level at this point, so I do believe that you can get to know somebody when you don't meet them in person. I also, one anecdote is that it wasn't quite the pre-seed round, but our seed round that was co-led by .9 Capital, Christoph and the .9 team, Had a ton of conviction around Loom after only meeting one of the co-founders, Shahid, and after 1:45 minute conversation, they put a term sheet on the table, and we ended up working together because Kristoff and the .9 team had recorded a bunch of Looms and sent them over to us about what they fe…

AI assessment note: “I do believe that you can get to know somebody when you don't meet them in person.”

Q I guess kind of taking the logical next step though, then obviously Andrew from Coya came in, and I spoke to Andrew before the show, and he said, ask about the Series B, ask how it went down, and specifically what did the Sequoia B team do to try and win and close the deal?

A So Andrew Reid was an intro from Dylan Field of Figma, one of our early angels, And Andrew and I built the relationship over the course of nine months. At one of our coffee meetings, he told me, I know this is weird logic, but bear with me. I'm getting married in October, and I'd just really like to lead your Series B before I leave for the wedding and honeymoon. And we told him that, and I told him that we didn't think we were going to be fundraising for another couple quarters, but, you know, we'll pull a deck together and see what progress we've made. And he After a couple turns of feedback on the deck, Andrew asked me to meet him for a drink, and I thought that this was just to spend a little bit more time in a casual manner, which most of our meetings up until that point had been coffee meetings during the day or in the loom office, and so I thought it was just kind of like a little bit of casual hangout. When we were about to leave, he was like, oh, I also have this for you, and it was a term sheet that he put on the table, and the even more casual leave behind Was when we were walking out, we were like, high-fiving, like, doing the hug thing. He was also like, oh, and one more thing. And he sent an email that had 20 Sequoia partners and team members, including Rulof, Doug Leone, Michael Morwitz, who all recorded a Loom talking about why they were so excited to join Loom …

AI assessment note: “sent an email that had 20 Sequoia partners and team members”

Q I consistently get the board deck three to four days beforehand, and I haven't got a board letter ever before. So I guess my question is like, how do you structure the board letter? If you double click on the board letter itself, how do you structure that? Is it the same every time? Do you send it four or five days before? What's the process around the board letter?

A It's evolved over time as the business has evolved, but really what has stayed true from the beginning is that there's an intro vignette. So what is something that's top of mind? That's interesting that I feel like is very relevant to our vision and mission. So make sure to start the letter With what it is that we're really doing at the company and where we're striving to go. From there, you touch on the key metrics to the business. What are the two or three North Star metrics that you're driving against? What was the progress over the last three months? And how do you feel about them? And then from there, there's going to be the key things that you as a board have decided is most important for you to work on in that quarter. And so you deep dive on those topics and you share what What progress that you've made and how, again, how you're feeling about it. And then the last part of it is there's usually a special project for a CEO. So whether it's recruiting for a VP or whether it's working on a workplace communication and collaboration doc for the entire company that you feel is critically important to spearhead because that's what your company offers to the world. And what's really important as you triple headcount over the course of the year that You're able to clearly articulate to the company how to best communicate and collaborate with each other. So you give an update on …

AI assessment note: “So you give a few highlights from that content, and then you just link to the deck”

Q one aspect of multiple data points to collect. We've spoken about the investors there, and I do want to discuss fundraising itself, because when we chatted before, you mentioned the words to me, highly inefficient, mistrust laden, and overhaul when it comes to kind of the more matter of fundraising itself. Walk me through your thinking here. What are your thoughts on this, and how do you think about that?

A So, I'll take a few steps back here, because hearing mistrust-laden out loud is a little bit more negative and harsh than I thought when I originally wrote it, but I stick with the highly inefficient part. We kept hearing over and over again when we were raising our most recent round that was co-led by Sequoia and Code Two that we're calling our Series B+, is that We're not quite sure we can make an investment with a company and team we haven't met in person. And it goes without thinking now a few months on that we're all kind of in this COVID territory is that this is antiquated thinking. The fundraise industry was very quickly and radically forced to change their operating procedures because some firms were willing to take that leap to make the investment during early COVID without meeting in person, and they won deals as a result. So The inefficient part for me doing it in person was running, literally running sometimes from VC office to VC office for a couple weeks, which is a ton of work and overhead. And for those that haven't done a fundraise process, it sounds prestigious and fun, but it's really, it's a slog. And so this most recent fundraise was my favorite for a couple reasons. One, it was all over video conferencing. So there was no time between meetings trying to squeeze in emails or messages from From a phone, I got a meaningful amount of non-fundraised work done …

AI assessment note: “I stick with the highly inefficient part. We kept hearing over and over again”

Q Are we going to build a big company today? Do you think that's a very different one that needs to be in person, and it's actually at the later stages when, ironically, more money's at stake, you can go off with video only. I'm intrigued, like, does it change then, and do you not feel as a founder you want to see the whites of my eyes to trust me?

A It's a great question, and I do believe that video is, specifically, like, video conferencing is an incredibly powerful way to get to know somebody if you are structured with your time together. So, One thing that I actually really enjoyed with Code Two and their onboarding process, this happened after the fundraise, is that we did a dinner together, and it was over the course of two, two and a half hours. There were partners that came in and out of the video call, but what we did for one part of it was we actually went through that New York Times, like, 36 questions to fall in love, and we asked these really deep and meaningful questions of each other, To get to know the individual, and I felt like even though I still haven't officially met Matt Mazzeo or Lucas Swisher of Cote Two in person, um, I feel like I know them at a pretty intimate level at this point, so I do believe that you can get to know somebody when you don't meet them in person. I also, one anecdote is that it wasn't quite the pre-seed round, but our seed round that was co-led by .9 Capital, Christoph and the .9 team, Had a ton of conviction around Loom after only meeting one of the co-founders, Shahid, and after 1:45 minute conversation, they put a term sheet on the table, and we ended up working together because Kristoff and the .9 team had recorded a bunch of Looms and sent them over to us about what they fe…

AI assessment note: “I do believe that you can get to know somebody when you don't meet them”

Q That is, uh, that is very kind of you. Now, I have to admit, I'm probably one of the biggest fanboys of Loom, but I'm going to pretend like I'm not. So tell me, Joe, how did you make your way into the wonderful world of startups and tech, but also come to found the game changer that is Loom today?

A It all started in the Chicago suburbs. Fun fact is that Shahid, Vinay, and myself are all from a 20 mile radius of each other, who are the co-founders of Loom, but we didn't know each other until California. So for me personally, I come from a family of entrepreneurs, but they're not the Silicon Valley entrepreneurs. They're the Midwest entrepreneurs, like running a golf course, or having a paper print shop, or even a local cable hunting television show. So I was always encouraged to do my own thing growing up, And when I went to school for economics at Indiana University, my freshman year was actually the 2008 market crash. And when I was looking around for internships, most specifically in the finance world, nothing really spoke to me. And it was something that really caused me to look internally and say, what is it that I want to do relatively early on in my college career? So I actually started a creative agency because my childhood best friend was a design major at University of Illinois. And we just started working with Local businesses and college startups. It was really fun. It paid the rent and bar tabs, and over the course of a couple years at college, by the time I got midway through my senior year, I realized I wasn't going to do anything with my major. So I actually ended up dropping out and moving out to California, and that was much to my parents' chagrin. So we …

AI assessment note: “So we moved to Silicon Beach to get closer to the tech scene”

Q I consistently get the board deck three to four days beforehand, and I haven't got a board letter ever before. So I guess my question is like, how do you structure the board letter? If you double click on the board letter itself, how do you structure that? Is it the same every time? Do you send it four or five days before? What's the process around the board letter?

A It's evolved over time as the business has evolved, but really what has stayed true from the beginning is that there's an intro vignette. So what is something that's top of mind? That's interesting that I feel like is very relevant to our vision and mission. So make sure to start the letter With what it is that we're really doing at the company and where we're striving to go. From there, you touch on the key metrics to the business. What are the two or three North Star metrics that you're driving against? What was the progress over the last three months? And how do you feel about them? And then from there, there's going to be the key things that you as a board have decided is most important for you to work on in that quarter. And so you deep dive on those topics and you share what What progress that you've made and how, again, how you're feeling about it. And then the last part of it is there's usually a special project for a CEO. So whether it's recruiting for a VP or whether it's working on a workplace communication and collaboration doc for the entire company that you feel is critically important to spearhead because that's what your company offers to the world. And what's really important as you triple headcount over the course of the year that You're able to clearly articulate to the company how to best communicate and collaborate with each other. So you give an update on …

AI assessment note: “what has stayed true from the beginning is that there's an intro vignette.”

Q Wow, that's a good suggestion. I always say the same on interviews. I always say there's no such thing as a bad interview, only kind of bad questions. So I'm actually probably going to read that one, so uh, that's exciting. And the first, normally I just say I'll read Don't read them. But, uh, tell me, what's your biggest strength and biggest weakness as a leader, Joe?

A I believe my biggest strength is authentic empathy, to understand where a customer, a candidate, or a co-worker is coming from, to genuinely want to find a mutually beneficial path forward, because you deeply care about them. Finding win-wins is truly the key to life, and that comes from a place of authentic empathy, but it also cuts both ways. It's my weakness as a leader, too. It can be exhausting, and in an extreme form of empathy, you become a people pleaser, and so sometimes at the expense of what the company needs me to do, I want to make an individual happy. So this is something that my executive coaches highlighted that I really need to work on, but I also believe it's my biggest strength.

AI assessment note: “I believe my biggest strength is authentic empathy... It's my weakness as a leader, too.”

Q Can I ask a really tough one? How do you think about, I always think like the best CEOs know the 90% of the investor advice To disregard and the 10% to keep. How do you think about deciding which advice to keep versus which to disregard?

A I think that it relates to the most recent question as well, which is the fact that really good investors also caveat any suggestions that they provide with. This is just a data point. And that's what I actually have felt really encouraged by Ilya and Andrew and the early investors is that they don't have full context into the business as passionate as they are. We are the ones who are working on it day to day, hour over hour, and so I think that investor advice is always, always comes from a good place. We're all trying to maximize the value per share of the company, and we're trying to innovate on behalf of our customers, but it's just one data point, and so to me, a data informed decision is critically important. Your investor's perspective is an important data point, but fundamentally, you're never going to have Perfect information to make a perfect decision. And so it boils down to, of all the data that you've collected, including an investor opinion or advice, what is your intuition and gut telling you? And just go forward with that.

AI assessment note: “including an investor opinion or advice, what is your intuition and gut telling you?”

Q go back to like the earlier stages, I spoke to Ben at Elementum, who was one of your earliest seed investors, and he asked, what advice would you give to founders on how to pick your early VCs? Let's start with that, and then we can discuss ramifications for future rounds. But in terms of picking, how do you think about picking the early VCs and the advice you give?

A I think that the three things that I thought about was conviction. So having true believers in the company and That trust your vision is the most important. So the signal here again is kind of looping back to questions that they ask versus giving advice. I think is conviction. They immediately want to invest because they just see the future that you see and that they're going to ask really good questions. The other part is supporters. So when the going gets tough and it absolutely will, you want investors who support you and your decisions to While you're also asking the tough questions to test your logic. And then the third thing that has been incredibly helpful for our earliest investors is the former operators and founders. I'm not saying to exclusively fundraise from former operators or funders, but certainly have them on the cap table because you want your earliest investors to be those who have been on the other side of the table. They will have deep empathy for the early journey. And I think that between those three kind of criteria, we were able to bring together a group of folks that were incredibly valuable to us in the earliest days.

AI assessment note: “the three things that I thought about was conviction.”

Q Yeah, no, I absolutely agree. And can I ask in terms of like what Loom is doing specifically, I'm just interested here. What are you doing specifically? Because I see so many of these company posts when Which are recognizing it and talking about the education. What specifically is Loom doing to move the needle?

A Yeah, so we initially did a block of donations, um, about three weeks ago, four weeks ago, when this all really picked up. But what we collectively discussed as a leadership team, and this was spearheaded by Salesforce, which is the one percent contribution. And so we collectively as a company said that we were going to do that one percent donation. Right now it's revenue. In the future, it'll be Profit. And we'll kind of like start to transition that over time. Is it one percent revenue, one percent profit? But we are committed to every single month donating one percent of our revenue to causes. And in the near term, over the next six to 12 months, it is going to be to organizations that are helping and on the front lines of civil rights. And I believe if you have consistent donations to certain communities or certain organizations over the long term, it means that you will mentally commit and invest yourself as well. We're also implementing and working with organizations and programs in order to, from an inclusion and equity perspective, how do we make sure that we have equal pay and equal opportunity across the entire company? And how do we make sure that we do not have bias within any of our operations? And so we're working with organizations on that front and moving pretty aggressively to make sure that we unroot any of that bias as quickly as we can.

AI assessment note: “we are committed to every single month donating one percent of our revenue to causes”

Q Wow, that's a good suggestion. I always say the same on interviews. I always say there's no such thing as a bad interview, only kind of bad questions. So I'm actually probably going to read that one, so uh, that's exciting. And the first, normally I just say I'll read Don't read them. But, uh, tell me, what's your biggest strength and biggest weakness as a leader, Joe?

A I believe my biggest strength is authentic empathy, to understand where a customer, a candidate, or a co-worker is coming from, to genuinely want to find a mutually beneficial path forward, because you deeply care about them. Finding win-wins is truly the key to life, and that comes from a place of authentic empathy, but it also cuts both ways. It's my weakness as a leader, too. It can be exhausting, and in an extreme form of empathy, you become a people pleaser, and so sometimes at the expense of what the company needs me to do, I want to make an individual happy. So this is something that my executive coaches highlighted that I really need to work on, but I also believe it's my biggest strength.

AI assessment note: “I believe my biggest strength is authentic empathy... It's my weakness as a leader, too.”

Q Can I ask a really tough one? How do you think about, I always think like the best CEOs know the 90% of the investor advice To disregard and the 10% to keep. How do you think about deciding which advice to keep versus which to disregard?

A I think that it relates to the most recent question as well, which is the fact that really good investors also caveat any suggestions that they provide with. This is just a data point. And that's what I actually have felt really encouraged by Ilya and Andrew and the early investors is that they don't have full context into the business as passionate as they are. We are the ones who are working on it day to day, hour over hour, and so I think that investor advice is always, always comes from a good place. We're all trying to maximize the value per share of the company, and we're trying to innovate on behalf of our customers, but it's just one data point, and so to me, a data informed decision is critically important. Your investor's perspective is an important data point, but fundamentally, you're never going to have Perfect information to make a perfect decision. And so it boils down to, of all the data that you've collected, including an investor opinion or advice, what is your intuition and gut telling you? And just go forward with that.

AI assessment note: “of all the data that you've collected... what is your intuition and gut telling you?”

Q go back to like the earlier stages, I spoke to Ben at Elementum, who was one of your earliest seed investors, and he asked, what advice would you give to founders on how to pick your early VCs? Let's start with that, and then we can discuss ramifications for future rounds. But in terms of picking, how do you think about picking the early VCs and the advice you give?

A I think that the three things that I thought about was conviction. So having true believers in the company and That trust your vision is the most important. So the signal here again is kind of looping back to questions that they ask versus giving advice. I think is conviction. They immediately want to invest because they just see the future that you see and that they're going to ask really good questions. The other part is supporters. So when the going gets tough and it absolutely will, you want investors who support you and your decisions to While you're also asking the tough questions to test your logic. And then the third thing that has been incredibly helpful for our earliest investors is the former operators and founders. I'm not saying to exclusively fundraise from former operators or funders, but certainly have them on the cap table because you want your earliest investors to be those who have been on the other side of the table. They will have deep empathy for the early journey. And I think that between those three kind of criteria, we were able to bring together a group of folks that were incredibly valuable to us in the earliest days.

AI assessment note: “I think that the three things that I thought about was conviction.”

Q Yeah, no, I absolutely agree. And can I ask in terms of like what Loom is doing specifically, I'm just interested here. What are you doing specifically? Because I see so many of these company posts when Which are recognizing it and talking about the education. What specifically is Loom doing to move the needle?

A Yeah, so we initially did a block of donations, um, about three weeks ago, four weeks ago, when this all really picked up. But what we collectively discussed as a leadership team, and this was spearheaded by Salesforce, which is the one percent contribution. And so we collectively as a company said that we were going to do that one percent donation. Right now it's revenue. In the future, it'll be Profit. And we'll kind of like start to transition that over time. Is it one percent revenue, one percent profit? But we are committed to every single month donating one percent of our revenue to causes. And in the near term, over the next six to 12 months, it is going to be to organizations that are helping and on the front lines of civil rights. And I believe if you have consistent donations to certain communities or certain organizations over the long term, it means that you will mentally commit and invest yourself as well. We're also implementing and working with organizations and programs in order to, from an inclusion and equity perspective, how do we make sure that we have equal pay and equal opportunity across the entire company? And how do we make sure that we do not have bias within any of our operations? And so we're working with organizations on that front and moving pretty aggressively to make sure that we unroot any of that bias as quickly as we can.

AI assessment note: “we are committed to every single month donating one percent of our revenue to causes”

Q That is, uh, that is very kind of you. Now, I have to admit, I'm probably one of the biggest fanboys of Loom, but I'm going to pretend like I'm not. So tell me, Joe, how did you make your way into the wonderful world of startups and tech, but also come to found the game changer that is Loom today?

A It all started in the Chicago suburbs. Fun fact is that Shahid, Vinay, and myself are all from a 20 mile radius of each other, who are the co-founders of Loom, but we didn't know each other until California. So for me personally, I come from a family of entrepreneurs, but they're not the Silicon Valley entrepreneurs. They're the Midwest entrepreneurs, like running a golf course, or having a paper print shop, or even a local cable hunting television show. So I was always encouraged to do my own thing growing up, And when I went to school for economics at Indiana University, my freshman year was actually the 2008 market crash. And when I was looking around for internships, most specifically in the finance world, nothing really spoke to me. And it was something that really caused me to look internally and say, what is it that I want to do relatively early on in my college career? So I actually started a creative agency because my childhood best friend was a design major at University of Illinois. And we just started working with Local businesses and college startups. It was really fun. It paid the rent and bar tabs, and over the course of a couple years at college, by the time I got midway through my senior year, I realized I wasn't going to do anything with my major. So I actually ended up dropping out and moving out to California, and that was much to my parents' chagrin. So we …

AI assessment note: “moved to Silicon Beach to get closer to the tech scene”

Q documentation process that you really adopt. I've spoken to John at Stripe about this quite a few times. He's a big fan of long form writing, and I know you're a big fan of long form writing too. So why are you such a big fan of long form writing? I guess what's the structure to your writing From kind of a meta perspective, and how do you unpack that?

A Yeah, it is a great question, and credit where credit is due. Bezos is the one to popularize long-form writing in the modern workforce. He said something along the lines of clear writing and clear thinking go hand in hand. So over the years, there have been many different beads of writing strung together that I've done, from investor updates to fundraise learnings to board letters to This is actually a shout out to Peter Reinhart of segment who strongly encouraged me to get into the habit of writing board letters from the very first board meeting that we had. It's also team charters. I try and do a weekly CEO note, although that goes in waves depending on how busy I am and each having their kind of like own structure and cadence with one of our cultural values being lead with transparency. I'm pretty open book with the challenges we're facing with whatever group I'm writing for. And that's all rooted in confidence that whomever you share this long-form writing with, they'll only be able to be truly helpful if you're open with the situation and how you're feeling about it. That was Ilya's, Ilya Fishman, our board member from Kleiner, encouragement at every turn. Don't just give the facts, provide the perspective. And my advice to founders is that writing is a skill. Start sharpening it early. Write in narrative form. Tell a story. Make sure that it's relevant content and data, s…

AI assessment note: “clear writing and clear thinking go hand in hand”

Q inevitably occur. When you look at Loom's story from the outside, honestly, it kind of just looks like up and to the right. When you think back, what was the, holy shit, that was a challenge moment when the servers went down, when your VP of sales left and the world was falling apart. When you think back to the real old shit moment, Is there one that stands out?

A I think that there was an oh shit moment when we were going to raise our series A, and we had not deployed our revenue generating product yet, which we believed was a critical risk vector to de-risk for our series A investor to prove that people were willing to pay for it. And all the surveys and research in the world is not going to be the same data point as having a user actually paying you. And so, as we went to go into the Series A fundraise, and cash was starting to get low on the balance sheet, and you start to worry about, are you actually going to be able to get a meaningful investment in this next round without deluding yourselves like crazy, where all of a sudden, you own a relatively trivial amount of the company early on in the life cycle in order to just keep it alive and make sure that it survives. And so, as we started to gear up For our Series A fundraise, I was having a lot of anxiety about getting that done, and pretty much every single investor helped in their own way in terms of packaging up the stories, making connections, doing the back channels to make sure that certain investment partners were hearing the right things. Now, we ended up fundraising from Ilya, who had moved over to Kleiner at that point from Index, but we were worried, even though he individually had a ton of conviction about Loom, We weren't able to get the seed round done with Index, and…

AI assessment note: “there was an oh shit moment when we were going to raise our series A”

Q I like that. That's good, and I'm glad that I provided some dinner conversation. Tell me, what would you most like to change about the world of tech in the Valley?

A Yeah, this one is actually pretty serious in nature. I was talking to a candidate the other day for a leadership position at Loom, and one of the questions that I asked them that is to get to know them was, what have you noticed that surprised you most in the last couple weeks? And they happened to be black, and they said that they were surprised that That the next civil rights movement akin to the movement in the sixties is starting right now in the States. And they were shocked with how much open pushback there has been across the nation in some of the highest positions in the country. And so I feel like it's our duty as leaders to look at ourselves and ask, what are we doing to provide equal opportunity and representation, particularly for the black community? To make up for historical inequities. And then for myself personally, where I feel like I have control is within the tech sphere. So I think that generally we need to be doing this across the board. And today I would like to see a meaningful change in diversity and representation across all aspects of tech, particularly for the black community.

AI assessment note: “I would like to see a meaningful change in diversity and representation across all aspects”

Q that anxiety, and I love, to be fair, Ilya's conviction. No offense, like, going in pre-revenue without that existing, like, paying customer-based bait-out, so I do love that. A question that Ben had elemented Did also ask was in terms of when you look at that early investor base, what are the ramifications of the early choices of your investor selection for the follow on rounds with tier one investors?

A Yep. So all investors, you have to, as a founder, see this with eyes wide open because while your partners in the business, their business model is to maximize their ownership in your company while not harming the trajectory of it. And so having investors who Who know where that threshold is of when to fight for ownership, when to push for it, and then when to let a tier one firm in who also has their ownership requirements is really, really important. I think that we got ourselves into a couple sticky situations when you go into fundraising is how much are you talking about in terms of ownership for each investor as they get really interested in the company and making sure to have those Early conversations with the early investors to let them know what's coming to let the tier one in is critically important, and I think I've learned my lessons on that front as proper expectation setting, and I think that those investors who are willing to work with you as a founder and maybe as a first-time founder who's learning these lessons as they go is really important.

AI assessment note: “sticky situations when you go into fundraising is how much are you talking about in terms of ownership”

Q that anxiety, and I love, to be fair, Ilya's conviction. No offense, like, going in pre-revenue without that existing, like, paying customer-based bait-out, so I do love that. A question that Ben had elemented Did also ask was in terms of when you look at that early investor base, what are the ramifications of the early choices of your investor selection for the follow on rounds with tier one investors?

A Yep. So all investors, you have to, as a founder, see this with eyes wide open because while your partners in the business, their business model is to maximize their ownership in your company while not harming the trajectory of it. And so having investors who Who know where that threshold is of when to fight for ownership, when to push for it, and then when to let a tier one firm in who also has their ownership requirements is really, really important. I think that we got ourselves into a couple sticky situations when you go into fundraising is how much are you talking about in terms of ownership for each investor as they get really interested in the company and making sure to have those Early conversations with the early investors to let them know what's coming to let the tier one in is critically important, and I think I've learned my lessons on that front as proper expectation setting, and I think that those investors who are willing to work with you as a founder and maybe as a first-time founder who's learning these lessons as they go is really important.

AI assessment note: “when to let a tier one firm in who also has their ownership requirements”

Q documentation process that you really adopt. I've spoken to John at Stripe about this quite a few times. He's a big fan of long form writing, and I know you're a big fan of long form writing too. So why are you such a big fan of long form writing? I guess what's the structure to your writing From kind of a meta perspective, and how do you unpack that?

A Yeah, it is a great question, and credit where credit is due. Bezos is the one to popularize long-form writing in the modern workforce. He said something along the lines of clear writing and clear thinking go hand in hand. So over the years, there have been many different beads of writing strung together that I've done, from investor updates to fundraise learnings to board letters to This is actually a shout out to Peter Reinhart of segment who strongly encouraged me to get into the habit of writing board letters from the very first board meeting that we had. It's also team charters. I try and do a weekly CEO note, although that goes in waves depending on how busy I am and each having their kind of like own structure and cadence with one of our cultural values being lead with transparency. I'm pretty open book with the challenges we're facing with whatever group I'm writing for. And that's all rooted in confidence that whomever you share this long-form writing with, they'll only be able to be truly helpful if you're open with the situation and how you're feeling about it. That was Ilya's, Ilya Fishman, our board member from Kleiner, encouragement at every turn. Don't just give the facts, provide the perspective. And my advice to founders is that writing is a skill. Start sharpening it early. Write in narrative form. Tell a story. Make sure that it's relevant content and data, s…

AI assessment note: “clear writing and clear thinking go hand in hand.”

Q It sounds like an incredible person, so I'm sorry for the loss there, but, um, yeah, I'm glad that you had that time with him. I do want to do a final question, and probably the most important, which is the next five years for you and for Loom, and just how big could it be, and what does that roadmap look like?

A We want to accelerate information flow for the global workforce, And we want to empower people to communicate more effectively wherever they are. I think that there's great examples of organizations that have remained incredibly disciplined, provided best in class user experiences. For us specifically, it'll be video messaging. And from there, we can scale ourselves really, really far. I mean, we plan to address every single knowledge worker in the world. And what's interesting is now that we have a mobile app in this space, we're starting to see not just knowledge workers, but people at work. Using video messaging to communicate with each other. So I like to say that we're changing the face of workplace communication, fun little pun there, and that it's going to be a revolution in terms of percentage of communication that's happening over much higher bandwidth communication that's more efficient, that's more effective, and most importantly, more expressive. And so if you can make workplace communication more efficient and more effective first, but also at the same time, make it more expressive so that way you build Meaningful relationships with each other, with a globally distributed workforce , I believe that we're really just scratching the surface with where we're at with video messaging and how far Loom can take it for the world.

AI assessment note: “we plan to address every single knowledge worker in the world.”