The Exchanges

Q It totally does, and it kind of leaves you going and feeling kind of one step behind. I guess my question subsequently is, what else would you advise maybe others entering the fundraise process as a woman or as a minority, really in order to be as successful as you have been in getting the best people on your cap table?

A Okay, so I have a few suggestions there. So the first is, try to build up your network, because it's going to be warm introductions that are required. To get those meetings in the first place. I mean, in my case, my in into the VC community actually came from a Wharton professor of mine, so I did my MBA at Wharton. Adam Grant connected me to Hunter Walk, who ended up connecting me to James Currier, and then, you know, that kind of just blew open the whole thing for me, right? So your network and getting these warm introductions is critical, and so if you don't have that already established, just hustle your way into establishing that. The second is just your story and your pitch. It matters so much, the content of what you're saying. I learned very quickly that traction isn't what gets deals done. What gets deals done is an amazing story with a huge vision, with a huge market that you're pursuing, and a very unique insight about how you're going to achieve it. And then the third piece is the process. I see many, many CEOs not run a very tight or clean process here. So what I often recommend is, this is going to sound a little bit disparaging maybe, but I'm just going to say it. You need to meet the Tier three investors first, then the tier two, and end with the tier one. It's very much like job interviews where, like, you practice on companies that you don't care about as much,…

AI assessment note: “So the first is, try to build up your network, because it's going to be warm introductions”

Q Absolutely love it. Can I ask, and I suppose James is Before the show, and so this is unfair, because it's slightly off schedule, but how did you come up with the idea for Incredible Health, and what was that ideation process like for you?

A Yeah, so in terms of the idea itself, a lot of my family members and friends are doctors and surgeons, and they're often complaining about understaffing. You know, their ORs were understaffed, or didn't have enough nurses, or they didn't want to leave their patients with travel nurses, and then at the same time, Rome Portlock, who's my co-founder, software engineer from MIT, his sisters are nurses. And they were saying, hey, I'm experienced, I'm qualified, and it still takes me two to three months to get my next job. I submit my application to so many places, and I usually never hear back. So like many things in healthcare, we're like, oh, clearly there's a big disconnect here, and a massive amount of inefficiency, and so that's kind of where this started. We were like, there has to be a better way, and we came up with this concept for Incredible Health.

AI assessment note: “so in terms of the idea itself, a lot of my family members”

Q love resourcefulness being a core tenant there. I wish more founders that I invest in had that too. Tell me that I do want to ask, because fundraising plays a big role on the mindset and the psychology of being a leader and CEO. And it's a personal question, so I hope it's okay for me to ask, but how do you manage the psychology of being a CEO today?

A You know, Ben Horowitz in his book, Hard Things About Hard Things, one of the first things he says is the number one job of the CEO is to manage your own psychology. And I've, now that I've been like in the trenches here, like it's so true. The CEO job or my job is changing every six weeks. And we're making a lot of decisions every single day. And then we're not always certain if we're making the right decisions, right? Because you're making decisions in the absence of data sometimes. So managing psychology has been critical to me in terms of the key ways I do it is, honestly, I have a therapist, and I generally encourage all CEOs to just get one. There's a lot of anxiety and stress in this job, so whatever external professional support you can get is probably going to be quite helpful. Executive coaching I've had mixed experience with. I mean, I know there are some CEOs that found it helpful. I guess I haven't found the right one yet. And then the third thing is just to make sure you are surrounded by a bunch of other CEOs. Effectively, you have a support group. So when my social life has really now skews two founders, which is kind of sad, but it's great as well because this is a group that can really empathize together and really support each other, and many of us are going through very similar experiences.

AI assessment note: “managing psychology has been critical to me in terms of the key ways I do it”

Q Absolutely love it. Can I ask, and I suppose James is Before the show, and so this is unfair, because it's slightly off schedule, but how did you come up with the idea for Incredible Health, and what was that ideation process like for you?

A Yeah, so in terms of the idea itself, a lot of my family members and friends are doctors and surgeons, and they're often complaining about understaffing. You know, their ORs were understaffed, or didn't have enough nurses, or they didn't want to leave their patients with travel nurses, and then at the same time, Rome Portlock, who's my co-founder, software engineer from MIT, his sisters are nurses. And they were saying, hey, I'm experienced, I'm qualified, and it still takes me two to three months to get my next job. I submit my application to so many places, and I usually never hear back. So like many things in healthcare, we're like, oh, clearly there's a big disconnect here, and a massive amount of inefficiency, and so that's kind of where this started. We were like, there has to be a better way, and we came up with this concept for Incredible Health.

AI assessment note: “clearly there's a big disconnect here, and a massive amount of inefficiency”

Q you, it's incredibly kind of a high achiever status and tone. My question is, Do you struggle in that case, then, in terms of delegation and kind of really, I'm a control freak, and I kind of desperately retain control because I think I trust myself probably more than I trust other people to do things. How do you think about delegation, and was that a challenge with the scale?

A Yeah, I haven't been particularly challenged with it because there's two, three things that I keep in mind. Number one, I cannot let myself become a bottleneck because I end up being the number one thing that slows down the company. Number two is I know I'm not an expert in everything, and so just to have the humility to Know that I'm not an expert in whatever operations. I mean, I can get it to a certain point, you know, I can get it to like a C grade, but there's no way that I have the expertise or experience to get it to an A grade. But someone who's done operations for 1015 years probably can. So yeah, there's a combination of humility and just like the fact that, hey, like we need to move really fast here. Speed is the only competitive advantage a startup has. And so if you are a bottleneck and you're slowing things down, then that just has to change.

AI assessment note: “I haven't been particularly challenged with it because there's two, three things”

Q And so what did the process then look like?

A So the process to even get those insights, Was not straightforward at all. Went through a pivot. Pivots are extremely tough to go through psychologically. What it means is that, you know, we have to basically change the entire company and change what we're doing altogether, but they're very common, right, in Silicon Valley, and I guess they should be celebrated, not ridiculed, right? So we were working on a completely different company for a year, and it was a SaaS platform for small and medium healthcare businesses, and even though it was live and we were making some money from it, we could just could not get it to grow, despite a bunch of efforts. And so once we met the team at NFX, we made the decision to pivot and went through a very robust ideation process. That included coming up with a hundred different ideas, applying multiple filters to them, like market size, competition. What is your unique insight? What have you come up with that's at least 10 times better? And just by simply applying those filters, we had narrowed the hundred ideas down to 10, and then went in-depth on customer research and market research and really Figuring out what all our different insights are. Now, once we did that, you know, and narrowed down from 10 to one, and the one idea is incredible health.

AI assessment note: “narrowed the hundred ideas down to 10, and then went in-depth on customer research”

Q Totally. I do agree with you in terms of surrounding yourself with those people. Again, a really personal question, but one that always really affects me, I'm riddled with, you know, imposter syndrome, especially being kind of Younger than most in the industry. Is imposter syndrome something that you've faced, and how do you think about that, and self-doubt, I guess? Is there any advice you'd give me?

A Yeah, sure. I mean, I think anyone who's, like, uh, high-achieving probably has some form of imposter syndrome, regardless of your demographic and your age and so on. Yeah, that's something that I had to deal with as well. There's a few, I guess, hacks that I use in the early days, particularly in positions when I was selling, right? So you're selling when you're in Fundraising. You're selling when you're filling the customers, and you're also selling to employees. Join the team. I pretty much adopted an alter ego, and this alter ego actually happens to be a white male who, you know, who, who is highly privileged as well, because I had observed how members of that demographic operate. Like, I see them walking into a room, and the amount of confidence and assertiveness that they have, so I'm like, okay, I need that, and so I called my alter ego Chad. And so before walking into a room, you know, I'd be like, okay, I'm not going to be Eman for the next 60 minutes. I'm going to be Chad. And Chad walks into a room with an insane amount of assertiveness and confidence, and that is what's needed when you're selling. You know, I don't need it anymore. Chad and Eman have now become one. But I did need it in the early days. Even if your content and your substance is fantastic, adding that confidence and assertiveness is extremely helpful as well. And that really is what ultimately Ends u…

AI assessment note: “Yeah, that's something that I had to deal with as well.”

Q And so what did the process then look like?

A So the process to even get those insights, Was not straightforward at all. Went through a pivot. Pivots are extremely tough to go through psychologically. What it means is that, you know, we have to basically change the entire company and change what we're doing altogether, but they're very common, right, in Silicon Valley, and I guess they should be celebrated, not ridiculed, right? So we were working on a completely different company for a year, and it was a SaaS platform for small and medium healthcare businesses, and even though it was live and we were making some money from it, we could just could not get it to grow, despite a bunch of efforts. And so once we met the team at NFX, we made the decision to pivot and went through a very robust ideation process. That included coming up with a hundred different ideas, applying multiple filters to them, like market size, competition. What is your unique insight? What have you come up with that's at least 10 times better? And just by simply applying those filters, we had narrowed the hundred ideas down to 10, and then went in-depth on customer research and market research and really Figuring out what all our different insights are. Now, once we did that, you know, and narrowed down from 10 to one, and the one idea is incredible health.

AI assessment note: “went through a very robust ideation process. That included coming up with a hundred different ideas”

Q tweet and you look back and you're not so proud of them. How do you feel when you look at this massive rise of VC Twitter personally? When you do look at it and then look at a lot of the parody accounts ripping the shit out of VCs, how do you feel about it as a founder and someone truly in the mix with some of the best investors?

A Yeah, I think, look, overall, I think it's positive, actually, whether it's VC Twitter or the blogs and so on, because given the amount of content that's out there to help you figure out how to build a company, some of that content is actually quite helpful. I'll point out a couple of very specific examples, not necessarily from VC Twitter, but from blogs that have been extremely helpful. Bill Gurley wrote a blog post in 2011 on his above the crowd blog. I forget the title, something around like not all revenues created equal. And this blog post, which is extremely in-depth with a ton of examples, effectively gives us the end state of what our companies should be, whether it's unit economics or the need for organic growth and so on, right? And when you look at that, you can treat it like a roadmap and be like, okay, this is what my company has to be at the end. So let me work backwards as I'm here at the early stages and make sure we're properly set up to achieve that. And to start making progress towards those goals. I mean, that's very helpful. The NFX content around their guide around the 13 or 12 different types of network effects, and they literally codify each one with examples. I mean, my product team still use that when we're trying to figure out what to do and trying to understand the importance of the network effects and exactly which type of network effect are we add…

AI assessment note: “overall, I think it's positive, actually, whether it's VC Twitter or the blogs”

Q because when we chatted before, we also chatted about kind of MBAs being super helpful as a startup CEO. And I was really interested by this because, you know, speaking of VC Twitter, there's a lot of kind of Twitter around the negatives of MBAs. So why do you feel about the benefits of MBAs? First, why do you feel this? And what are the big pros in your mind?

A Okay, the big pros of having an MBA, whether it's a top tier school or not, honestly. Listen, outside of the VC community does give you some credibility. Like when you're selling to enterprise customers, for example. Two is that it's specifically the finance and accounting classes you take are incredibly helpful when you're building a business. If you are capable of building a financial model where the P&L and the balance sheet tie together, and you can manage the cash in your business, and you can model it out and have projections and so on, it is extremely helpful. Managing your cash is like just such an important part of running a An early stage, rapidly growing startup when you have external capital coming in, you got revenue coming in, and you know, you need to manage things like dilution and so on. Like, being on top of the finances is extremely, extremely helpful. It definitely comes across when you're pitching as well. Luckily, in our Series A, we have the top three VCs in the world and give us term sheets, and a couple of them commented, the fact that you are on top of this stuff is actually quite rare. We meet many CEOs that are just not You know, they may have other backgrounds, right, and they just, their financial models are kind of a joke, and the way they're managing their finances is not great, so I think it's an advantage.

AI assessment note: “the big pros of having an MBA... finance and accounting classes you take are incredibly helpful”

Q It totally does, and it kind of leaves you going and feeling kind of one step behind. I guess my question subsequently is, what else would you advise maybe others entering the fundraise process as a woman or as a minority, really in order to be as successful as you have been in getting the best people on your cap table?

A Okay, so I have a few suggestions there. So the first is, try to build up your network, because it's going to be warm introductions that are required. To get those meetings in the first place. I mean, in my case, my in into the VC community actually came from a Wharton professor of mine, so I did my MBA at Wharton. Adam Grant connected me to Hunter Walk, who ended up connecting me to James Currier, and then, you know, that kind of just blew open the whole thing for me, right? So your network and getting these warm introductions is critical, and so if you don't have that already established, just hustle your way into establishing that. The second is just your story and your pitch. It matters so much, the content of what you're saying. I learned very quickly that traction isn't what gets deals done. What gets deals done is an amazing story with a huge vision, with a huge market that you're pursuing, and a very unique insight about how you're going to achieve it. And then the third piece is the process. I see many, many CEOs not run a very tight or clean process here. So what I often recommend is, this is going to sound a little bit disparaging maybe, but I'm just going to say it. You need to meet the Tier three investors first, then the tier two, and end with the tier one. It's very much like job interviews where, like, you practice on companies that you don't care about as much,…

AI assessment note: “The first is, try to build up your network, because it's going to be warm introductions”

Q love resourcefulness being a core tenant there. I wish more founders that I invest in had that too. Tell me that I do want to ask, because fundraising plays a big role on the mindset and the psychology of being a leader and CEO. And it's a personal question, so I hope it's okay for me to ask, but how do you manage the psychology of being a CEO today?

A You know, Ben Horowitz in his book, Hard Things About Hard Things, one of the first things he says is the number one job of the CEO is to manage your own psychology. And I've, now that I've been like in the trenches here, like it's so true. The CEO job or my job is changing every six weeks. And we're making a lot of decisions every single day. And then we're not always certain if we're making the right decisions, right? Because you're making decisions in the absence of data sometimes. So managing psychology has been critical to me in terms of the key ways I do it is, honestly, I have a therapist, and I generally encourage all CEOs to just get one. There's a lot of anxiety and stress in this job, so whatever external professional support you can get is probably going to be quite helpful. Executive coaching I've had mixed experience with. I mean, I know there are some CEOs that found it helpful. I guess I haven't found the right one yet. And then the third thing is just to make sure you are surrounded by a bunch of other CEOs. Effectively, you have a support group. So when my social life has really now skews two founders, which is kind of sad, but it's great as well because this is a group that can really empathize together and really support each other, and many of us are going through very similar experiences.

AI assessment note: “in terms of the key ways I do it is, honestly, I have a therapist”

Q agree also with the pipeline being a slight BS get out. A lot also say, oh, well, you know, in the Valley, Harry, it's such a homogenous culture and demographic base that it's incredibly hard to hire diverse teams. But when we chatted before, you interestingly said the Bay Area remains the best place in the world to build a tech company. Why do you believe this so prominently still?

A All right. So I genuinely believe the Bay Area is the best place to build a software company in the world. Best place in the world. A lot of people have written about the capital and the talent and the whole ecosystem, right? Yes. Talent, capital, all of that's great. But what really sets the Bay Area apart is the information network effects is what I call them. The fact that I can have a conversation with Over breakfast, lunch, brunch, dinner, drinks, whatever, with other founders, investors, operators, multiple times a day, and this is happening, by the way, thousands of times, tens of thousands of times a day, all over the Bay Area, where a ton of information is being exchanged. Like, that does not happen in other cities. And some of the information being exchanged are things like which investors to pursue and which ones to avoid, who to hire, and how to find them. Honestly, sometimes even competitor information that you shouldn't even have, right? Gets shared in these conversations. You know, ideas on growth tactics and strategy. Like, there's so much information here, and it's such a dense network that if you're not here, you're really missing out.

AI assessment note: “what really sets the Bay Area apart is the information network effects”

Q NFX there, and obviously investors and ideation geniuses that they are, but I want to touch on the fundraise, because when we chatted before, there are a couple of big elements that Came up and it's not always easy to raise, especially not if you don't fit the, maybe the white male stereotype. And so I'd love to hear how was the experience for you first? Let's start with that.

A Okay. So I had raised a seed round in 2017 and then our series a most recently in 2019. And so, yeah, I've had multiple experiences fundraising. I thought overall, look, the experience for me went smoothly. I will say though, that we all know the data, the statistics that women get a tiny fraction of venture capital dollars. I think black Female woman get zero, one percent of VC dollars, which is effectively zero. So we know that the odds are stacked against us statistically and there's a ton of bias in the system. But the interesting thing is that when you are raising as a minority or as a woman, one of the key things I did, and I often recommend to other CEOs is like, you just have to ignore that. You have to ignore the statistics and the data and the bias and all of that, because that's not what's going to get the round done. What's going to get the round done is your assertiveness, your ability to clearly communicate a vision, a market, a product, Your traction, and so on, and you really just have to ignore that, because that can just really mess you up psychologically to even think about it.

AI assessment note: “I thought overall, look, the experience for me went smoothly.”

Q because when we chatted before, we also chatted about kind of MBAs being super helpful as a startup CEO. And I was really interested by this because, you know, speaking of VC Twitter, there's a lot of kind of Twitter around the negatives of MBAs. So why do you feel about the benefits of MBAs? First, why do you feel this? And what are the big pros in your mind?

A Okay, the big pros of having an MBA, whether it's a top tier school or not, honestly. Listen, outside of the VC community does give you some credibility. Like when you're selling to enterprise customers, for example. Two is that it's specifically the finance and accounting classes you take are incredibly helpful when you're building a business. If you are capable of building a financial model where the P&L and the balance sheet tie together, and you can manage the cash in your business, and you can model it out and have projections and so on, it is extremely helpful. Managing your cash is like just such an important part of running a An early stage, rapidly growing startup when you have external capital coming in, you got revenue coming in, and you know, you need to manage things like dilution and so on. Like, being on top of the finances is extremely, extremely helpful. It definitely comes across when you're pitching as well. Luckily, in our Series A, we have the top three VCs in the world and give us term sheets, and a couple of them commented, the fact that you are on top of this stuff is actually quite rare. We meet many CEOs that are just not You know, they may have other backgrounds, right, and they just, their financial models are kind of a joke, and the way they're managing their finances is not great, so I think it's an advantage.

AI assessment note: “specifically the finance and accounting classes you take are incredibly helpful”

Q you mentioned kind of the role change every six weeks. It's actually a lot more frequent than people said on the show before being six months, which was interesting, but in terms of kind of the leadership change, if you're being self-reflective, now it's been an incredible journey, an incredible few years, but how have you seen yourself change and evolve as a leader over the last few years specifically?

A So in terms of the leadership changes that happen, first, the actual role and the content, the actual things I'm doing day to day have changed a lot, right? And they do change rapidly. So in the early days, when it's just two founders, you know, Rome's writing code, and I'm the one talking to customers and selling and so on, right? And fundraising. So I have transitioned from being an individual contributor who's literally doing everything to like just rapidly firing myself from different functions and different tasks, right? So as a founder and CEO, you are very much a generalist. There is no CEO, you know, my expertise is in product, but there is no CEO out there that is an expert in product and marketing and operations and finance and like everything, right? So over time, as you're hiring people for your team, you are bringing in deep domain experts in specific functions, and you are firing yourself from them, right? So when I hire a controller, he is literally 10 times better at me on finance, right?

AI assessment note: “transitioned from being an individual contributor who's literally doing everything to like just rapidly firing myself”

Q importance of managing cash, and it is off schedule, but when you raise a larger round like you did with the Andrees, is it a difficult mental transition to make, moving from the super lean, small seed rounds that are raised, to Wow, I've actually now got thirteen million dollars in my account, and you know, we need to move fast. Is that a difficult mental transition as a leader?

A Not so much, because you still have to stay, I mean, one of our values is resourcefulness, so we still have to be careful with the cash. We're doing a lot more things, of course, but we're still making decisions in the same way. Like, is hiring this person, or launching this market, or whatever it is, going to grow the business or not? Are there other places we should spend instead? So those conversations are still happening very much in the same way they were During the seed. I mean, I think the big difference between seed and A was prior to the series A, we're doing whatever we could to reach product market fit. So the team was actually very lean and we're doing whatever we can to get that initial product market fit. And then the series A is very much about, okay, we have some form of product market fit. What can we do to scale and continue making that fit even stronger? So I guess the objective has changed, but the way we use the cash has really not.

AI assessment note: “Not so much, because you still have to stay, I mean, one of our values”

Q NFX there, and obviously investors and ideation geniuses that they are, but I want to touch on the fundraise, because when we chatted before, there are a couple of big elements that Came up and it's not always easy to raise, especially not if you don't fit the, maybe the white male stereotype. And so I'd love to hear how was the experience for you first? Let's start with that.

A Okay. So I had raised a seed round in 2017 and then our series a most recently in 2019. And so, yeah, I've had multiple experiences fundraising. I thought overall, look, the experience for me went smoothly. I will say though, that we all know the data, the statistics that women get a tiny fraction of venture capital dollars. I think black Female woman get zero, one percent of VC dollars, which is effectively zero. So we know that the odds are stacked against us statistically and there's a ton of bias in the system. But the interesting thing is that when you are raising as a minority or as a woman, one of the key things I did, and I often recommend to other CEOs is like, you just have to ignore that. You have to ignore the statistics and the data and the bias and all of that, because that's not what's going to get the round done. What's going to get the round done is your assertiveness, your ability to clearly communicate a vision, a market, a product, Your traction, and so on, and you really just have to ignore that, because that can just really mess you up psychologically to even think about it.

AI assessment note: “I thought overall, look, the experience for me went smoothly.”

Q importance of managing cash, and it is off schedule, but when you raise a larger round like you did with the Andrees, is it a difficult mental transition to make, moving from the super lean, small seed rounds that are raised, to Wow, I've actually now got thirteen million dollars in my account, and you know, we need to move fast. Is that a difficult mental transition as a leader?

A Not so much, because you still have to stay, I mean, one of our values is resourcefulness, so we still have to be careful with the cash. We're doing a lot more things, of course, but we're still making decisions in the same way. Like, is hiring this person, or launching this market, or whatever it is, going to grow the business or not? Are there other places we should spend instead? So those conversations are still happening very much in the same way they were During the seed. I mean, I think the big difference between seed and A was prior to the series A, we're doing whatever we could to reach product market fit. So the team was actually very lean and we're doing whatever we can to get that initial product market fit. And then the series A is very much about, okay, we have some form of product market fit. What can we do to scale and continue making that fit even stronger? So I guess the objective has changed, but the way we use the cash has really not.

AI assessment note: “Not so much, because you still have to stay... one of our values is resourcefulness”

Q Totally. I do agree with you in terms of surrounding yourself with those people. Again, a really personal question, but one that always really affects me, I'm riddled with, you know, imposter syndrome, especially being kind of Younger than most in the industry. Is imposter syndrome something that you've faced, and how do you think about that, and self-doubt, I guess? Is there any advice you'd give me?

A Yeah, sure. I mean, I think anyone who's, like, uh, high-achieving probably has some form of imposter syndrome, regardless of your demographic and your age and so on. Yeah, that's something that I had to deal with as well. There's a few, I guess, hacks that I use in the early days, particularly in positions when I was selling, right? So you're selling when you're in Fundraising. You're selling when you're filling the customers, and you're also selling to employees. Join the team. I pretty much adopted an alter ego, and this alter ego actually happens to be a white male who, you know, who, who is highly privileged as well, because I had observed how members of that demographic operate. Like, I see them walking into a room, and the amount of confidence and assertiveness that they have, so I'm like, okay, I need that, and so I called my alter ego Chad. And so before walking into a room, you know, I'd be like, okay, I'm not going to be Eman for the next 60 minutes. I'm going to be Chad. And Chad walks into a room with an insane amount of assertiveness and confidence, and that is what's needed when you're selling. You know, I don't need it anymore. Chad and Eman have now become one. But I did need it in the early days. Even if your content and your substance is fantastic, adding that confidence and assertiveness is extremely helpful as well. And that really is what ultimately Ends u…

AI assessment note: “that's something that I had to deal with as well. There's a few, I guess, hacks”

Q you mentioned kind of the role change every six weeks. It's actually a lot more frequent than people said on the show before being six months, which was interesting, but in terms of kind of the leadership change, if you're being self-reflective, now it's been an incredible journey, an incredible few years, but how have you seen yourself change and evolve as a leader over the last few years specifically?

A So in terms of the leadership changes that happen, first, the actual role and the content, the actual things I'm doing day to day have changed a lot, right? And they do change rapidly. So in the early days, when it's just two founders, you know, Rome's writing code, and I'm the one talking to customers and selling and so on, right? And fundraising. So I have transitioned from being an individual contributor who's literally doing everything to like just rapidly firing myself from different functions and different tasks, right? So as a founder and CEO, you are very much a generalist. There is no CEO, you know, my expertise is in product, but there is no CEO out there that is an expert in product and marketing and operations and finance and like everything, right? So over time, as you're hiring people for your team, you are bringing in deep domain experts in specific functions, and you are firing yourself from them, right? So when I hire a controller, he is literally 10 times better at me on finance, right?

AI assessment note: “transitioned from being an individual contributor who's literally doing everything to like just rapidly firing myself”

Q you, it's incredibly kind of a high achiever status and tone. My question is, Do you struggle in that case, then, in terms of delegation and kind of really, I'm a control freak, and I kind of desperately retain control because I think I trust myself probably more than I trust other people to do things. How do you think about delegation, and was that a challenge with the scale?

A Yeah, I haven't been particularly challenged with it because there's two, three things that I keep in mind. Number one, I cannot let myself become a bottleneck because I end up being the number one thing that slows down the company. Number two is I know I'm not an expert in everything, and so just to have the humility to Know that I'm not an expert in whatever operations. I mean, I can get it to a certain point, you know, I can get it to like a C grade, but there's no way that I have the expertise or experience to get it to an A grade. But someone who's done operations for 1015 years probably can. So yeah, there's a combination of humility and just like the fact that, hey, like we need to move really fast here. Speed is the only competitive advantage a startup has. And so if you are a bottleneck and you're slowing things down, then that just has to change.

AI assessment note: “I haven't been particularly challenged with it because there's two, three things”

Q agree also with the pipeline being a slight BS get out. A lot also say, oh, well, you know, in the Valley, Harry, it's such a homogenous culture and demographic base that it's incredibly hard to hire diverse teams. But when we chatted before, you interestingly said the Bay Area remains the best place in the world to build a tech company. Why do you believe this so prominently still?

A All right. So I genuinely believe the Bay Area is the best place to build a software company in the world. Best place in the world. A lot of people have written about the capital and the talent and the whole ecosystem, right? Yes. Talent, capital, all of that's great. But what really sets the Bay Area apart is the information network effects is what I call them. The fact that I can have a conversation with Over breakfast, lunch, brunch, dinner, drinks, whatever, with other founders, investors, operators, multiple times a day, and this is happening, by the way, thousands of times, tens of thousands of times a day, all over the Bay Area, where a ton of information is being exchanged. Like, that does not happen in other cities. And some of the information being exchanged are things like which investors to pursue and which ones to avoid, who to hire, and how to find them. Honestly, sometimes even competitor information that you shouldn't even have, right? Gets shared in these conversations. You know, ideas on growth tactics and strategy. Like, there's so much information here, and it's such a dense network that if you're not here, you're really missing out.

AI assessment note: “what really sets the Bay Area apart is the information network effects”

Q or reducing the importance of being that. I do want to ask another interesting element that I spoke to a little birdie before the show, and they told me in terms of your style, you take a ton of notes in meetings. First, they asked, how do you keep everything organized? And then they asked, how do you decide what to act on versus what to file away for later?

A So yes, I do take notes in meetings, especially, I mean, I'm guessing the little birdies were either advisors or investors, because if I have one hour of time with them, I'm going to try again, I'm going to try to extract as much value as I can. And, you know, these are busy people too, so I just want to make sure I get all the content. The other thing is, I use an app called Todoist, and it, you know, syncs with mobile and laptop and everything, so I use that to, like, manage my tasks, and when I wake up in the morning, I'm like, what are the four things I need to get done today? Everything else is just not going to get done, and that's kind of how I keep myself organized, and then my notes, I keep a lot of it in Evernote, so it's always searchable and easy to find.

AI assessment note: “I use an app called Todoist... that's kind of how I keep myself organized”

Q tweet and you look back and you're not so proud of them. How do you feel when you look at this massive rise of VC Twitter personally? When you do look at it and then look at a lot of the parody accounts ripping the shit out of VCs, how do you feel about it as a founder and someone truly in the mix with some of the best investors?

A Yeah, I think, look, overall, I think it's positive, actually, whether it's VC Twitter or the blogs and so on, because given the amount of content that's out there to help you figure out how to build a company, some of that content is actually quite helpful. I'll point out a couple of very specific examples, not necessarily from VC Twitter, but from blogs that have been extremely helpful. Bill Gurley wrote a blog post in 2011 on his above the crowd blog. I forget the title, something around like not all revenues created equal. And this blog post, which is extremely in-depth with a ton of examples, effectively gives us the end state of what our companies should be, whether it's unit economics or the need for organic growth and so on, right? And when you look at that, you can treat it like a roadmap and be like, okay, this is what my company has to be at the end. So let me work backwards as I'm here at the early stages and make sure we're properly set up to achieve that. And to start making progress towards those goals. I mean, that's very helpful. The NFX content around their guide around the 13 or 12 different types of network effects, and they literally codify each one with examples. I mean, my product team still use that when we're trying to figure out what to do and trying to understand the importance of the network effects and exactly which type of network effect are we add…

AI assessment note: “overall, honestly, it's quite positive, but they could tone down the sarcasm”

Q I do want to ask you, if we kind of progress that along, and you get the investors that you do, the likes of James Currier, the likes of Andreessen, and this one was from James Currier, so maybe slightly self-serving, but there's always the promise of venture value add. What do you find most helpful about your investor? And where do you think VCs could improve or do better?

A All right. So my lead investor for the seed round is actually James Joaquin at Obvious Ventures, and James Currier and NFX participated, so Charles Hudson at Precursor, and then the Series A was led by Jeff Jordan and Andreessen Horowitz. Now, in terms of value add, I know that, you know, a lot of VCs say they add value, but the reality of it is some do and some don't. So one of the key things that my investors have done for me are closing candidates, whether it's software engineers or executives or whoever. It's just helpful for candidates to hear that outsider's perspective on your company, and so they've helped me do that. The second is introductions to hospital executives all over the country. Whether it's Obvious Ventures or Andreessen Horowitz, both have introduced me to hospital execs. Some of them are even their LPs, and that's been extremely helpful with helping us grow our business. The third is just as an advisor to me, the CEO. Whether it's James Joaquin or Jeff Jordan or the team at NFX, these are all very experienced operators. Many of them have built several, several companies, They've been around since the late nineties. They have taken companies public. They're just an experienced group of operators. And so that's really helpful for me because they can help me look around corners, right? And point out what to look out for, what to avoid, prevent mistakes from h…

AI assessment note: “one of the key things that my investors have done for me are closing candidates”

Q I do want to ask you, if we kind of progress that along, and you get the investors that you do, the likes of James Currier, the likes of Andreessen, and this one was from James Currier, so maybe slightly self-serving, but there's always the promise of venture value add. What do you find most helpful about your investor? And where do you think VCs could improve or do better?

A All right. So my lead investor for the seed round is actually James Joaquin at Obvious Ventures, and James Currier and NFX participated, so Charles Hudson at Precursor, and then the Series A was led by Jeff Jordan and Andreessen Horowitz. Now, in terms of value add, I know that, you know, a lot of VCs say they add value, but the reality of it is some do and some don't. So one of the key things that my investors have done for me are closing candidates, whether it's software engineers or executives or whoever. It's just helpful for candidates to hear that outsider's perspective on your company, and so they've helped me do that. The second is introductions to hospital executives all over the country. Whether it's Obvious Ventures or Andreessen Horowitz, both have introduced me to hospital execs. Some of them are even their LPs, and that's been extremely helpful with helping us grow our business. The third is just as an advisor to me, the CEO. Whether it's James Joaquin or Jeff Jordan or the team at NFX, these are all very experienced operators. Many of them have built several, several companies, They've been around since the late nineties. They have taken companies public. They're just an experienced group of operators. And so that's really helpful for me because they can help me look around corners, right? And point out what to look out for, what to avoid, prevent mistakes from h…

AI assessment note: “one of the key things that my investors have done for me are closing candidates”

Q this a little bit, though, to the team itself before we move into the quickfire, because there are a couple of really interesting elements that I do want to hit on. First is kind of team diversity, something that you've absolutely excelled at, but maybe the ecosystem lags a little bit behind. What have been some of your biggest lessons on the right way to hire a really diverse team?

A Yeah, so the way I think about diversity is not just demographic diversity, but also diversity in backgrounds and experiences. Experiences too, right? So there's a lot of business research out there that shows that more diverse teams are more successful. They did a lot of this research on public companies, and more diverse teams just drive more shareholder value. And so, like, I just academically, fundamentally believe it's really important in a business to have a diverse team, because it's going to enable us to win. So, in terms of how to do it, the way I think about it is that you have to do it from the very beginning, from the very first employees. And the reason it's so important to do it from the very beginning is because if you wait, You wait until, let's say, you're 20 people, you're all one thing. You're all one demographic, for example. You're all, I don't know.

AI assessment note: “you have to do it from the very beginning, from the very first employees.”

Q or reducing the importance of being that. I do want to ask another interesting element that I spoke to a little birdie before the show, and they told me in terms of your style, you take a ton of notes in meetings. First, they asked, how do you keep everything organized? And then they asked, how do you decide what to act on versus what to file away for later?

A So yes, I do take notes in meetings, especially, I mean, I'm guessing the little birdies were either advisors or investors, because if I have one hour of time with them, I'm going to try again, I'm going to try to extract as much value as I can. And, you know, these are busy people too, so I just want to make sure I get all the content. The other thing is, I use an app called Todoist, and it, you know, syncs with mobile and laptop and everything, so I use that to, like, manage my tasks, and when I wake up in the morning, I'm like, what are the four things I need to get done today? Everything else is just not going to get done, and that's kind of how I keep myself organized, and then my notes, I keep a lot of it in Evernote, so it's always searchable and easy to find.

AI assessment note: “I use an app called Todoist... my notes, I keep a lot of it in Evernote”

Q it seems to retweet me and like my tweets more than any other. So I think something to be worried about there. But I do want to remain on this because obviously you meet many investors during the raise and James actually asked this question and he asked what VCs did not invest, but did you really like and admire and why did you gain so much from those interactions?

A Yeah. So every CEO has a ton of rejection while they're fundraising, right? And there were definitely some fantastic VCs that did pass on us, both in the seed round and the series day. And the way I treat those conversations is I just try to extract as much value as I can. You know, usually, you know, 10 minutes into the pitch that they're probably going to say no. You can just tell from their demeanor and how they're asking questions and stuff. But I'm like, you know, I just need to sit here for another 40 minutes, right? So I'm just going to try to get as much value as I can. So I often ask questions like, hey, you met our competitors. What do you think of them? And what do you think of the market overall? And what did you think when I said this? Like, I just start asking them questions and honestly treating them like free consultants because they are, regardless of the tier that they're in, they are looking at companies and markets like all day, every day. And so there is some value in what they're saying. And the content of what they're telling me actually does help me improve my pitch and the next meeting.

AI assessment note: “treating them like free consultants because they are”