The Exchanges

Q Not at all. I'm excited for this one, but I do want to start today with a little bit on you. So tell me, how did you make your way into the world of startups and tech? But most importantly in that, what I'm most interested by is how did you come to be the prominent angel that you are today in the Valley?

A I moved out to the Bay area in. I knew I'd wanted to get involved in tech in some way. I'd seen a lot of the most ambitious people I knew moving to San Francisco to start or join startups, and it just felt like this was where the action was. And I continue to think that that's true. I first heard about Opendoor through a TechCrunch piece in the summer of 2014 and was really compelled by the idea. And I joined the team there as the 10th employee in an ops role, which at the time just meant everything non-technical. And while I was at Opendoor, I built and led our customer operations team. I was the GM of our first market, Phoenix. As well as the broader CityOps team, as we expanded, and then was chief of staff to our CEO for a year. And that was really my first experience at a startup, was there for around four and a half years. But while I was at Opendoor, I started to get some exposure to angel investing. And Eric Wu, Opendoor CEO, was actually a big part of that. So he shared a bunch of decks on deals he was looking at. He introduced me to other angels. And then my good friend, Afton Vetri, started Modern Fertility. And that became my first investment. Soon after that, I joined Sequoia's Scout program and started writing some more checks, and I absolutely love it, and I don't think I'll ever stop angel investing.

AI assessment note: “joined Sequoia's Scout program and started writing some more checks”

Q Yeah, no, absolutely. I mean, I guess when you have these metrics met a little bit more baked out with the priorities and You have to communicate them across the company and the teams. What have you learned and seen about the best way to truly communicate the priorities throughout the org, and what works?

A Yeah, I would say keep it simple, make it memorable, and explain the why. There was a point where we were working on hitting unit profitability in our core cities, where Eric decided he would show up to work every day wearing this blue t-shirt with the single most important company metric on it, and so everyone at the company knew the goal. I'm definitely not saying t-shirts are the only answer here, but Keeping it simple was really key. I will say the danger to using just a single metric, though, is what might be sacrificed to get there. So at Open Door, for example, if we raised our offers on people's homes, we'd see a bump in conversion. So yes, we would therefore hit our growth goals, but profitability would have suffered. Paired metrics are a great way to try to mitigate some of this. So saying, okay, this is our top line goal, but this other metric can't go below X.

AI assessment note: “keep it simple, make it memorable, and explain the why.”

Q further, then we kind of move more to the company's scaling perspective, because if you get it right, hopefully magical product market fit ensues. And I guess when you look back at the scaling journey for you with Open Door, you said before about the importance of building systems for growth and moving metrics. Can I ask, what did you mean by this building systems for growth and moving metrics?

A Absolutely. Building systems is really important to allow other people to come into the company and start operating to Figure out how to enable technology to actually make you more efficient at what you're doing. It really just means putting those rules and process in place around the things that are happening repeatedly in the business. In practice, what that means kind of to get started doing that is writing everything down or drawing out the flow charts of kind of everything that's going on in the operation. So first this happens, then this, who's involved, what are the dependencies, what data is required or what data is generated. At Opendoor, we started building our first systems out in spreadsheets. We used Asana templates at one point, email workflows, Slack bot, Zapier, you name it. I think it's super important to iterate for a while in the most lightweight tools that you can get away with, because inevitably you're going to be changing the way you do things. A mistake we made a few times early on was to commit to code some processes that just weren't fully baked yet and were continuing to evolve. And then because engineering resources are limited, which they often are, we had to Keep using these outdated systems that we had prematurely built for longer than we would have liked.

AI assessment note: “It really just means putting those rules and process in place around the things”

Q Yeah, no, absolutely. I mean, I guess when you have these metrics met a little bit more baked out with the priorities and You have to communicate them across the company and the teams. What have you learned and seen about the best way to truly communicate the priorities throughout the org, and what works?

A Yeah, I would say keep it simple, make it memorable, and explain the why. There was a point where we were working on hitting unit profitability in our core cities, where Eric decided he would show up to work every day wearing this blue t-shirt with the single most important company metric on it, and so everyone at the company knew the goal. I'm definitely not saying t-shirts are the only answer here, but Keeping it simple was really key. I will say the danger to using just a single metric, though, is what might be sacrificed to get there. So at Open Door, for example, if we raised our offers on people's homes, we'd see a bump in conversion. So yes, we would therefore hit our growth goals, but profitability would have suffered. Paired metrics are a great way to try to mitigate some of this. So saying, okay, this is our top line goal, but this other metric can't go below X.

AI assessment note: “keep it simple, make it memorable, and explain the why.”

Q I have a big question for you here. And it's, can you assign two people to a single task on a checklist? And what are your thoughts on kind of how that accountability drops or does it not if two people or more are accountable?

A Absolutely not. You need to have one person accountable. This is really important for something like selling and buying a house with Opendoor where there really were a lot of steps and there were different people involved. We built an admin system within Opendoor where each of the things on the checklist was assigned to a role at the company. So it might be the customer experience person or the field ops manager. And then next to that, within that role, there would always be a specific name. And that was really critical for For making sure people knew exactly what they were responsible for, and then if there was something that went wrong, we could figure out, hey, who was supposed to be doing that?

AI assessment note: “Absolutely not. You need to have one person accountable.”

Q Not at all. I'm excited for this one, but I do want to start today with a little bit on you. So tell me, how did you make your way into the world of startups and tech? But most importantly in that, what I'm most interested by is how did you come to be the prominent angel that you are today in the Valley?

A I moved out to the Bay area in. I knew I'd wanted to get involved in tech in some way. I'd seen a lot of the most ambitious people I knew moving to San Francisco to start or join startups, and it just felt like this was where the action was. And I continue to think that that's true. I first heard about Opendoor through a TechCrunch piece in the summer of 2014 and was really compelled by the idea. And I joined the team there as the 10th employee in an ops role, which at the time just meant everything non-technical. And while I was at Opendoor, I built and led our customer operations team. I was the GM of our first market, Phoenix. As well as the broader CityOps team, as we expanded, and then was chief of staff to our CEO for a year. And that was really my first experience at a startup, was there for around four and a half years. But while I was at Opendoor, I started to get some exposure to angel investing. And Eric Wu, Opendoor CEO, was actually a big part of that. So he shared a bunch of decks on deals he was looking at. He introduced me to other angels. And then my good friend, Afton Vetri, started Modern Fertility. And that became my first investment. Soon after that, I joined Sequoia's Scout program and started writing some more checks, and I absolutely love it, and I don't think I'll ever stop angel investing.

AI assessment note: “Soon after that, I joined Sequoia's Scout program and started writing some more checks”

Q kind of learning from those people. I'm very keen to kind of share the spotlight with those people who have been amazing to me. I mean, two for me are like Mike Maples and Brad Feld, always been unwavering in terms of that support and kind of knowledge guidance for me. Who's been kind of instrumental in your adaptation of the new role and really just building the knowledge base?

A Well, there are some people who I've actually never met who have been influential on me. I think about Paul Graham and his essays. I think about the P Marker archive that I've read. I haven't met either of those, although maybe at some point I will. And then there are people like Mike Maples, who has been generous. We've had a couple of Zoom calls, love listening to him on podcasts. I think he has some amazing thinking. Mike Fernald has been amazing over at Sequoia. He always takes the time to respond to my emails where I'm kind of outlining, hey, you know, I met with this company here, so I'm thinking about it. He'll ask some great probing questions back. We always have a lot of good discussion. So he's been wonderful as well.

AI assessment note: “Mike Fernald has been amazing over at Sequoia. He always takes the time”

Q about that. I'm really interested, because it's such an incredible experience seeing the hyper growth at a company like Opendoor, and so if you were to think back to the time, and now especially, If you were to choose one to two takeaways from your time with Open Door that impacted, I guess, both your operating and investment mindset, what would those one to two takeaways be, do you think?

A Absolutely. There were so many things I learned at Open Door, but one that stands out and that I find myself thinking about frequently as an investor is people solve problems with the tools that they have. That means that a founding team and their first hires there need to be matched to the core competencies required for that business. So take Open Door, for example. Those core competencies that we needed to be really good at were pricing, it was operations, it was capital market. With pricing, Opendoor's co-founder, Ian, is a data scientist, and so he was responsible for pricing accuracy, and he had that depth of experience in the field. He had a network there, and it was really critical to get right. We had to make sure Opendoor was delivering on fair offers so that we weren't coming in too low and hurting our reputation. People would call us lowballers, or coming in too high, which meant that we would buy a house that then We take a loss on when reselling it. So really critical that he was a part of that founding team and that he brought that focus to that part of the business that he worked on. He continues to work on to this day. And that really impacted my lens on investing, which is the founder market fit question is really important to me. So when I meet a founder, I always ask myself, is this the right person to start this business? What are the core competencies requi…

AI assessment note: “one that stands out and that I find myself thinking about frequently as an investor”

Q Totally get you in terms of kind of discovering those power users. I guess when you reflect on your process, what does it look like? How do you structure it? And are there core questions that you found most revealing in terms of discovering what customers fundamentally want?

A Absolutely. I think I always advise that people start with broad open-ended questions. You really can't go wrong there. This allows the customer to actually more proactively Bring up areas of concern or frustration that they have just to share what matters to them. And if you start with a set of more specific questions, you actually risk kind of steering that customer down a certain path, and they might not have actually brought something up that is really valuable and you would have wanted to know about. For example, when we were focused on building the seller product in the beginning at Opendoor, we were again, so focused on building a product that was all about selling. But when we went and started asking people to tell us about their experience selling their home, They were often talking to us about their next dream home, what they were so excited about buying and how they needed to sell their current home to be able to afford the down payment for the next one. And they just wanted to remove the stress and hassle of the sale and just be done with the whole selling part. And that really transformed the way we saw ourselves. And we saw the open door product selling was often in combination with buying. And so that came through in our product marketing and I think ultimately helped us develop a more compelling pitch to our customers.

AI assessment note: “I think I always advise that people start with broad open-ended questions.”

Q about that. I'm really interested, because it's such an incredible experience seeing the hyper growth at a company like Opendoor, and so if you were to think back to the time, and now especially, If you were to choose one to two takeaways from your time with Open Door that impacted, I guess, both your operating and investment mindset, what would those one to two takeaways be, do you think?

A Absolutely. There were so many things I learned at Open Door, but one that stands out and that I find myself thinking about frequently as an investor is people solve problems with the tools that they have. That means that a founding team and their first hires there need to be matched to the core competencies required for that business. So take Open Door, for example. Those core competencies that we needed to be really good at were pricing, it was operations, it was capital market. With pricing, Opendoor's co-founder, Ian, is a data scientist, and so he was responsible for pricing accuracy, and he had that depth of experience in the field. He had a network there, and it was really critical to get right. We had to make sure Opendoor was delivering on fair offers so that we weren't coming in too low and hurting our reputation. People would call us lowballers, or coming in too high, which meant that we would buy a house that then We take a loss on when reselling it. So really critical that he was a part of that founding team and that he brought that focus to that part of the business that he worked on. He continues to work on to this day. And that really impacted my lens on investing, which is the founder market fit question is really important to me. So when I meet a founder, I always ask myself, is this the right person to start this business? What are the core competencies requi…

AI assessment note: “one that stands out and that I find myself thinking about frequently as an investor”

Q kind of learning from those people. I'm very keen to kind of share the spotlight with those people who have been amazing to me. I mean, two for me are like Mike Maples and Brad Feld, always been unwavering in terms of that support and kind of knowledge guidance for me. Who's been kind of instrumental in your adaptation of the new role and really just building the knowledge base?

A Well, there are some people who I've actually never met who have been influential on me. I think about Paul Graham and his essays. I think about the P Marker archive that I've read. I haven't met either of those, although maybe at some point I will. And then there are people like Mike Maples, who has been generous. We've had a couple of Zoom calls, love listening to him on podcasts. I think he has some amazing thinking. Mike Fernald has been amazing over at Sequoia. He always takes the time to respond to my emails where I'm kind of outlining, hey, you know, I met with this company here, so I'm thinking about it. He'll ask some great probing questions back. We always have a lot of good discussion. So he's been wonderful as well.

AI assessment note: “there are some people who I've actually never met who have been influential on me”

Q this episode was brought to you by t-shirts.com, who are our kind sponsor. I do want to ask, I heard from, I think it was Mike Bernal actually, that you also have themed for checklists as part of the scaling process. So talk to me, how do you use checklists so efficiently? And I'm honestly, I'm terrible with checklists. How do you advise me and others to do the same?

A I am not a perfectionist or overly detail-oriented person. So this is absolutely a hack. Atul Gawande wrote this book called The Checklist Manifesto with the subtitle How to Get Things Right, and that's exactly what they're for. So, so checklists are really about delivering consistent quality, and if you think about what the mandate of the operations team was at Opendoor, it was exactly that. Another thing I'll say about checklists is that the person doing the checking should be responsible for the creation and the ownership of the checklist. Nobody wants a checklist if it's not actually useful. This is not one of those things where the manager writes it and hands it down to the team. In fact, I think it would probably have a bad outcome because the team actually knows the details of what's going on in the field or on the phone with customers. And instead having the team create and edit and manage their own checklists over time worked really well.

AI assessment note: “the person doing the checking should be responsible for the creation and the ownership”

Q Can I ask, what's the right way to layer? Because I have a lot of founders who say, I'm bringing in someone external and Julia or Suzanne is going to be upset about this. What's the right way to do it to not make her unhappy, disincentivize her? Do you have any thoughts and advice on the right way to layer?

A Yeah, I think it's important to actually bring the person in on the fact that you are going to be hiring someone in above them. Not necessarily to be interviewing them, but to kind of give them a bit of a heads up and to say, hey, this is what we're looking for. So here's our criteria. We want someone who has these skills or this many years of experience doing this thing. And they kind of understand the rationale and they're not blindsided by it because it kind of feels like they went behind your back or you weren't aware and you're surprised by it and not in a good way. So that would be the one thing I would say. And then the other would be to also just communicate to the team more broadly that the company is doing well. You're excited that These really experienced people want to join the team, right? And that they have done X, Y, Z things at other places, and they're going to actually add a ton of value to the team. And that the bar for staying hungry, staying scrappy, being hardworking does not change. And that applies to everyone, including new, more senior executives joining the team.

AI assessment note: “bring the person in on the fact that you are going to be hiring someone”

Q How long is long enough data to know that a process is right versus need to be iterated on? Is it like a couple of weeks? Is it a couple of months? How do you think about knowing when a process is right to be coded?

A It depends on how complex your operations are. I think it depends on the pace of the growth of the business. Somewhere between a few weeks and a few months is probably around right. When you do something for a week and think it's working, like you probably just haven't hit the edge cases yet. So give it a little bit of time. And then again, inevitably engineering resources are going to be limited. So you will find yourself naturally wanting to prioritize the areas that you do think are kind of the most locked. And so start there, let yourself kind of scrape by with spreadsheets for a while on the other stuff, but it can be almost worse to put something into code that, you know, kind of won't get prioritized or revisited for a while and then have to be working on something that's a little bit stale and outdated.

AI assessment note: “Somewhere between a few weeks and a few months is probably around right.”

Q about what to advise them with the kind of weight of responsibility. So I'm going to delegate this to you on this one. So they always say, should I join a startup? Should I start a startup or should I join an incumbent? How would you advise them given your firsthand experience with open door? And then also bluntly investing in the next gen of the newest startups rising today.

A Yeah, it's a great question. I would encourage everyone to begin with considering the start of startup path. I think it's like, why not? Most people I think today don't think or dream big enough and just going through the process would allow them to think about, okay, what might I work on? What might it take to start something? And I think that's really valuable thinking just in and of itself. That said, each of the paths has something different to offer. I think joining a larger company, you hopefully get exposed to best practices of a large organization. You probably work for someone who More experienced than you, more specialized, potentially. Going to a startup, you're probably going to end up taking on a role that you kind of wouldn't have gotten elsewhere otherwise, and so each of those paths has its pros and cons. I'd say that just whatever path you choose, the most important thing is to make sure you feel like you're working on the edge of your abilities, and you're achieving the kind of growth that you want for yourself every day.

AI assessment note: “I would encourage everyone to begin with considering the start of startup path.”

Q us invest pre-seed and seed. And bluntly, I always actually slightly diminish the importance of kind of analyzing CAC at seed because it's so transient. It changes so much. It's so platform dependent. And really, it's just such an unreliable metric in my eyes, especially at this early stage. How do you think about kind of the centrality of CAC and how much weight and prominence do you assign it?

A I think it's hard at the very early stage. You can try to look for benchmarks, right? But you won't really know what that CAC cost is going to look like. I do look for people who have given it some thought. So they say, hey, we acknowledge we're going to use paid marketing here, but we also have a unique and creative strategy over here about how we want to generate word of mouth, how we want to generate referrals, how we want to use content, maybe try to lean into SEO. I don't think SEO is dead. So if someone is being sort of holistic about how they're thinking about that blended CAC, I think that's really important. But at the very early stages, I think it's hard to know.

AI assessment note: “I do look for people who have given it some thought.”

Q you spoke about kind of scaling people there. And as I said, you scaled exceptionally within open And it was a question for me, which is like, generalists often have perspectives on scaling, and when we spoke beforehand, you mentioned thriving as a generalist. How do you think about thriving as a generalist, and how does one navigate that career path as a generalist, do you think, especially with scale?

A Generalists tend to thrive in environments where there are a lot of nebulous problems to solve, and kind of no overly specific skill set is needed, kind of need a lot of a few things, and this happens time and time again within fast-growing startups, so Generalists can be hugely valuable in those first few years, and they tend to thrive at the intersection of multiple disciplines, whether it's across quantitative and qualitative. And navigating a career here is, I almost think, easier in those first few years than it is later, because as organizations grow, you do need to have more specialists. You do need to have people with kind of more years of experience. So my advice here would be to first raise your hand to just say, I'm here to work on whatever's critical. Like put me to work and just bring that growth mindset, right? I can go ask a question if I'm not trying to do something, or I'm going to go Google it and look it up and figure it out. And then the second thing I'll say is don't be afraid to take on a specialist role. There were myself included people who went from general kind of biz ops and generalist operations to I'm going to go lead a sales team. And that means I'm going to go learn a lot about sales. I'm going to do sales myself. I'm going to get mentorship from other sales leaders. And I think generalists do have that ability to learn quickly on the job, and so …

AI assessment note: “my advice here would be to first raise your hand to just say, I'm here”

Q about what to advise them with the kind of weight of responsibility. So I'm going to delegate this to you on this one. So they always say, should I join a startup? Should I start a startup or should I join an incumbent? How would you advise them given your firsthand experience with open door? And then also bluntly investing in the next gen of the newest startups rising today.

A Yeah, it's a great question. I would encourage everyone to begin with considering the start of startup path. I think it's like, why not? Most people I think today don't think or dream big enough and just going through the process would allow them to think about, okay, what might I work on? What might it take to start something? And I think that's really valuable thinking just in and of itself. That said, each of the paths has something different to offer. I think joining a larger company, you hopefully get exposed to best practices of a large organization. You probably work for someone who More experienced than you, more specialized, potentially. Going to a startup, you're probably going to end up taking on a role that you kind of wouldn't have gotten elsewhere otherwise, and so each of those paths has its pros and cons. I'd say that just whatever path you choose, the most important thing is to make sure you feel like you're working on the edge of your abilities, and you're achieving the kind of growth that you want for yourself every day.

AI assessment note: “I would encourage everyone to begin with considering the start of startup path.”

Q How long is long enough data to know that a process is right versus need to be iterated on? Is it like a couple of weeks? Is it a couple of months? How do you think about knowing when a process is right to be coded?

A It depends on how complex your operations are. I think it depends on the pace of the growth of the business. Somewhere between a few weeks and a few months is probably around right. When you do something for a week and think it's working, like you probably just haven't hit the edge cases yet. So give it a little bit of time. And then again, inevitably engineering resources are going to be limited. So you will find yourself naturally wanting to prioritize the areas that you do think are kind of the most locked. And so start there, let yourself kind of scrape by with spreadsheets for a while on the other stuff, but it can be almost worse to put something into code that, you know, kind of won't get prioritized or revisited for a while and then have to be working on something that's a little bit stale and outdated.

AI assessment note: “Somewhere between a few weeks and a few months is probably around right.”

Q this episode was brought to you by t-shirts.com, who are our kind sponsor. I do want to ask, I heard from, I think it was Mike Bernal actually, that you also have themed for checklists as part of the scaling process. So talk to me, how do you use checklists so efficiently? And I'm honestly, I'm terrible with checklists. How do you advise me and others to do the same?

A I am not a perfectionist or overly detail-oriented person. So this is absolutely a hack. Atul Gawande wrote this book called The Checklist Manifesto with the subtitle How to Get Things Right, and that's exactly what they're for. So, so checklists are really about delivering consistent quality, and if you think about what the mandate of the operations team was at Opendoor, it was exactly that. Another thing I'll say about checklists is that the person doing the checking should be responsible for the creation and the ownership of the checklist. Nobody wants a checklist if it's not actually useful. This is not one of those things where the manager writes it and hands it down to the team. In fact, I think it would probably have a bad outcome because the team actually knows the details of what's going on in the field or on the phone with customers. And instead having the team create and edit and manage their own checklists over time worked really well.

AI assessment note: “having the team create and edit and manage their own checklists over time worked really well”

Q Can I ask, how is that uncovered when you think about those systems thinkers? What kind of, do you know what I mean? They, cause you obviously can't ask, are you a systems thinker? Like what kind of questions reveal someone's mindset towards being more systems thinking than others?

A It's a great question. I think it's actually hard to do in sort of like a one hour coffee meeting. What I will look for Are someone's ability to talk through the business structure. So how do they make money? What is their margin structure looking like? What are the costs associated with the business? How do those change over time? How do they think about deploying technology against any operational component they have in the business? And I do look for them to also acknowledge that, Hey, we're going to use people here and we're going to build a playbook and hire people to do this job. It kind of reminds me of Flexport or something. It's the people who are telling you they're going to automate everything they do. I also am quite Skeptical. So those are the types of questions I'll ask.

AI assessment note: “What I will look for Are someone's ability to talk through the business structure.”

Q us invest pre-seed and seed. And bluntly, I always actually slightly diminish the importance of kind of analyzing CAC at seed because it's so transient. It changes so much. It's so platform dependent. And really, it's just such an unreliable metric in my eyes, especially at this early stage. How do you think about kind of the centrality of CAC and how much weight and prominence do you assign it?

A I think it's hard at the very early stage. You can try to look for benchmarks, right? But you won't really know what that CAC cost is going to look like. I do look for people who have given it some thought. So they say, hey, we acknowledge we're going to use paid marketing here, but we also have a unique and creative strategy over here about how we want to generate word of mouth, how we want to generate referrals, how we want to use content, maybe try to lean into SEO. I don't think SEO is dead. So if someone is being sort of holistic about how they're thinking about that blended CAC, I think that's really important. But at the very early stages, I think it's hard to know.

AI assessment note: “if someone is being sort of holistic about how they're thinking about that blended CAC”

Q Can I ask, how is that uncovered when you think about those systems thinkers? What kind of, do you know what I mean? They, cause you obviously can't ask, are you a systems thinker? Like what kind of questions reveal someone's mindset towards being more systems thinking than others?

A It's a great question. I think it's actually hard to do in sort of like a one hour coffee meeting. What I will look for Are someone's ability to talk through the business structure. So how do they make money? What is their margin structure looking like? What are the costs associated with the business? How do those change over time? How do they think about deploying technology against any operational component they have in the business? And I do look for them to also acknowledge that, Hey, we're going to use people here and we're going to build a playbook and hire people to do this job. It kind of reminds me of Flexport or something. It's the people who are telling you they're going to automate everything they do. I also am quite Skeptical. So those are the types of questions I'll ask.

AI assessment note: “What I will look for Are someone's ability to talk through the business structure.”

Q I mean, these processes kind of obviously generate actions and metrics, and I'm interested on the moving metrics. Because we often hear about kind of the hailed north star that's unwavering. What are your thoughts on moving metrics and how do you approach that?

A Yeah, it's a great one. Moving metrics usually means they're stuck, right? If you're saying, hey, this metric isn't going anywhere, what's going on? How do we move it? The cost, for example, was a great one at Opendoor. We always wanted to remove costs. We wanted to work on our margin. One of the things that we focused on at Opendoor was what are the root causes of why maybe this metric Isn't moving. And so some of the engineers at open door actually introduced me to the framework of asking the five whys. So you just ask why over and over again. And a lot of this digging deep into what might the root cause be, I think was helpful in then coming up with new ideas, generating new thoughts around how you can kind of break through and come up with new ways to fix things.

AI assessment note: “Moving metrics usually means they're stuck, right?”

Q entire kind of customer lifecycle, There with kind of the vertical discussion. And I'm interested because I want to start on really the beginning of the life cycle of a customer and customer development is always core in that element. So when is the right time to really engage deeply in this customer development process, do you think? And then secondly, how do you select the customers you engage with?

A Yeah, absolutely. I think the best time to start is at the beginning, right? I'm a huge advocate for talking to customers as much as you can. And I found that over time, you know, Really can discover that next level of nuance and insight that you actually probably don't need to get to that first kernel of an idea, right? But later on, you sort of hone it, you learn more, you discover who your power users might be. I really like the term that Mike Maples uses value hacking. He talks about just like really digging in there and understanding, like, is this something really valuable? Who loves this thing? And then I do think it is important to kind of pull up, look around at the landscape. Are there other customers like this? Who are going to become power users, or am I risking building something that's a bit too niche?

AI assessment note: “I think the best time to start is at the beginning, right?”

Q If you can see my face now, it would be great because it's one of my favorites by far. And so I'm so pleased to hear that one. Tell me, operating a business and investing at the same time, how does it make you a better investor?

A Yeah. Operating and investing are incredibly complimentary. Investing encourages you to be up there at that 30,000 foot view, seeing patterns across industries, comparing business models, looking at macro trends to see where those next pockets of opportunity might be. But operating is much lower altitude. I would call it more bird's eye because you don't also want to be sort of like in the weeds for the whole time. But it allows you sort of observe what's going on within your business to see, hey, over there, product isn't working out. And then I think those two things can be very complimentary. Investors understand what it takes to operate something, and then on the flip side, operators are able to invest, thinking a bit more strategically, having looked at other businesses before, and then also understanding when to raise money.

AI assessment note: “operators are able to invest, thinking a bit more strategically”

Q I mean, these processes kind of obviously generate actions and metrics, and I'm interested on the moving metrics. Because we often hear about kind of the hailed north star that's unwavering. What are your thoughts on moving metrics and how do you approach that?

A Yeah, it's a great one. Moving metrics usually means they're stuck, right? If you're saying, hey, this metric isn't going anywhere, what's going on? How do we move it? The cost, for example, was a great one at Opendoor. We always wanted to remove costs. We wanted to work on our margin. One of the things that we focused on at Opendoor was what are the root causes of why maybe this metric Isn't moving. And so some of the engineers at open door actually introduced me to the framework of asking the five whys. So you just ask why over and over again. And a lot of this digging deep into what might the root cause be, I think was helpful in then coming up with new ideas, generating new thoughts around how you can kind of break through and come up with new ways to fix things.

AI assessment note: “Moving metrics usually means they're stuck, right?”

Q entire kind of customer lifecycle, There with kind of the vertical discussion. And I'm interested because I want to start on really the beginning of the life cycle of a customer and customer development is always core in that element. So when is the right time to really engage deeply in this customer development process, do you think? And then secondly, how do you select the customers you engage with?

A Yeah, absolutely. I think the best time to start is at the beginning, right? I'm a huge advocate for talking to customers as much as you can. And I found that over time, you know, Really can discover that next level of nuance and insight that you actually probably don't need to get to that first kernel of an idea, right? But later on, you sort of hone it, you learn more, you discover who your power users might be. I really like the term that Mike Maples uses value hacking. He talks about just like really digging in there and understanding, like, is this something really valuable? Who loves this thing? And then I do think it is important to kind of pull up, look around at the landscape. Are there other customers like this? Who are going to become power users, or am I risking building something that's a bit too niche?

AI assessment note: “I think the best time to start is at the beginning, right?”