The Exchanges

Q have those two to three issues that you're facing at that one time, do you direct them at certain people, or do you throw them out, say, hey, we're really struggling with a CTO hire, but I know, Brooke, you're amazing at this, or Danny, you're amazing at this, I need your help on this, or do you leave it open to the board for more general advice and guidance?

A It depends on the setting. When it's a board meeting, I generally won't overly direct toward a certain person for feedback. In fact, I think that all of our board members are generally like pretty thoughtful people on a whole bunch of different topics, and just because someone doesn't have direct expertise in an area doesn't mean that they can't weigh in. So our board meetings are more free-flowing conversations, and people weigh in when they have a point of view, but there's no grandstanding. We don't have board members that will speak just to be heard. It's not the type of environment that we've built. When it's outside of the board meeting, I'll call particular people with particular questions. Danny, for example, has a lot of depth in marketplaces, has seen a whole bunch of companies scale from very young to much larger, has seen the company scale. He invested in our seed rounds and has been with us the entire time. And so Danny has a lot of history and context that allows me to have really valuable conversations with him about where we're at, where we're going. Brooke, for example, at GTVP is more of a growth stage investor. And so as I think about how the company needs to mature based on where he sits and what he's seeing in his portfolio, that creates really valuable conversations on a different dimension. And so I try to recognize the respective strengths and roles of d…

AI assessment note: “It depends on the setting. When it's a board meeting, I generally won't overly direct”

Q hire that, I'm a massive nerd on kind of interview questions. Probably one of the many reasons I'm still single, Rob, but I do have to ask when adding to the team, do you, Have a favorite question. It's really unfair. I did warn you. Do you have a favorite question that you find most revealing of an individual's character, ability, culture fit? And if so, what is that question?

A I do have a favorite question. My favorite interview question is, let's imagine the next chapter of your career is the next five years. If that chapter goes perfectly, what happens, or where do you see yourself at the end of that chapter? To me, there's no substitute for understanding how much clarity someone has and where they want to go. And what they hope actually happens to them, or they can accomplish over that period. Because my job as a founder, and I think my job as a CEO over time, is to make sure that for as close to a hundred percent of the team as possible, their career goals, their professional development objectives over the next six months, 12 months, 24 months, five years, are actually aligned with things that I believe we can deliver, are opportunities that we can create at Scoop. And so I love asking that question, because the Clearer a sense that I can get for a candidate of where they want to go, and as I think about this role and opportunity, do I actually think I can deliver that for them, and is there overlap? It's just incredibly important.

AI assessment note: “I do have a favorite question. My favorite interview question is”

Q no, I love that, and I couldn't agree more with that kind of inherent trust that just has to be there. I spoke to Danny, again, a board member of Scoop and a man who knows a lot about families and business. In terms of kind of making it work, what are some of the challenges that make the day-to-day interesting, so to And how does that change with scale?

A The thing that probably made life hardest for us early on was focusing our energy at the same topics at the same time. And what made it really challenging is that we just think differently. We have different backgrounds. John was a product manager at Google. It takes a lot of those principles and the way he thinks about building business and product. I was at Bain, as we talked about as doing strategy consulting. And so we can quite often come up with two totally different perspectives on how to solve a Neither is inherently right or wrong. Early on, that was challenging, right? How do you actually hammer that together to come up with a clear point of view? Over time, that actually gets easier because as the company scales, the number of things that we both spend time on actually decreases quite a bit. So we can kind of carve out our own spheres of ownership and focus in a way that ends up being much more complimentary. The way that we ended up solving it, or at least working through big pieces of it, was trying to wear really clear hats. When are we talking to each other as co-founders and making decisions that are important for us to agree on unanimously? When am I acting as CEO and John acting as our chief product officer? When are we actually acting as brothers? And actually, it's a conversation that's actually separate from work, and we should recognize that in the way we …

AI assessment note: “Over time, that actually gets easier because as the company scales”

Q no, I love that, and I couldn't agree more with that kind of inherent trust that just has to be there. I spoke to Danny, again, a board member of Scoop and a man who knows a lot about families and business. In terms of kind of making it work, what are some of the challenges that make the day-to-day interesting, so to And how does that change with scale?

A The thing that probably made life hardest for us early on was focusing our energy at the same topics at the same time. And what made it really challenging is that we just think differently. We have different backgrounds. John was a product manager at Google. It takes a lot of those principles and the way he thinks about building business and product. I was at Bain, as we talked about as doing strategy consulting. And so we can quite often come up with two totally different perspectives on how to solve a Neither is inherently right or wrong. Early on, that was challenging, right? How do you actually hammer that together to come up with a clear point of view? Over time, that actually gets easier because as the company scales, the number of things that we both spend time on actually decreases quite a bit. So we can kind of carve out our own spheres of ownership and focus in a way that ends up being much more complimentary. The way that we ended up solving it, or at least working through big pieces of it, was trying to wear really clear hats. When are we talking to each other as co-founders and making decisions that are important for us to agree on unanimously? When am I acting as CEO and John acting as our chief product officer? When are we actually acting as brothers? And actually, it's a conversation that's actually separate from work, and we should recognize that in the way we …

AI assessment note: “Over time, that actually gets easier because as the company scales”

Q hire that, I'm a massive nerd on kind of interview questions. Probably one of the many reasons I'm still single, Rob, but I do have to ask when adding to the team, do you, Have a favorite question. It's really unfair. I did warn you. Do you have a favorite question that you find most revealing of an individual's character, ability, culture fit? And if so, what is that question?

A I do have a favorite question. My favorite interview question is, let's imagine the next chapter of your career is the next five years. If that chapter goes perfectly, what happens, or where do you see yourself at the end of that chapter? To me, there's no substitute for understanding how much clarity someone has and where they want to go. And what they hope actually happens to them, or they can accomplish over that period. Because my job as a founder, and I think my job as a CEO over time, is to make sure that for as close to a hundred percent of the team as possible, their career goals, their professional development objectives over the next six months, 12 months, 24 months, five years, are actually aligned with things that I believe we can deliver, are opportunities that we can create at Scoop. And so I love asking that question, because the Clearer a sense that I can get for a candidate of where they want to go, and as I think about this role and opportunity, do I actually think I can deliver that for them, and is there overlap? It's just incredibly important.

AI assessment note: “My favorite interview question is, let's imagine the next chapter of your career”

Q a, on a theme that's a real passion for both of us, decision-making. As I said, I spoke to many of your investors, and the commonality in the discussion was where you excel in decision-making. So, Brooke Porter mentioned your unique ability in how you approach key decisions. Let's start out on that. How do you approach And what does he mean when he says from a first principles perspective?

A A lot of how I think about decision-making actually comes from my time at Bain. So I spent six and a half years doing strategy consulting before I joined Scoop. And I think consulting, it gives you a really good approach to how do you break down complex problems into really simple elements. And to me, when I think about Building a business at the end of the day, building a business is a set of problems that you have to think through and solve. And any problem that you're trying to solve, you can break down into what are the questions we have to answer? What's the work I have to do to actually answer that question, executing that work, and then communicating the outcome and doing something about it. And so whenever I'm trying to make big decisions, or as a company, we think through this, always go back to first principles, digest that problem down and Think it through in pieces. We work very closely with our board and others to give feedback and input, but that served me very well, and it comes from prior experiences to scoop.

AI assessment note: “always go back to first principles, digest that problem down and Think it through in pieces”

Q I'm sure it also builds a culture of kind of accountability and responsibility that people love. On the element of data though, my partner at Fred Destin is also a huge note when it comes to the decision making, and he said before that decisions are never perfect. As a founder, what you're playing for is batting average. How do you think about that, and would you agree with him?

A I would fully agree with that. It's a funny thing that I talk about with my team is, look, you shouldn't assume that every decision I make is going to be right, but for Scoop to be successful, I have to be right a whole lot more often than I'm wrong over time for us to do what we need to do, and so I think it's in And that if you don't have a hundred percent information, you're not always going to make the right decision. And even if you did have a hundred percent information, realities change on the ground. People react in different ways than you intended. That's part of why experimentation is actually deeply important. I think the goal is to make decisions quickly and try and maximize for lack of better description, the product of how fast am I making decisions times how often am I right? That's really what you're trying to solve for.

AI assessment note: “I would fully agree with that.”

Q And then final one, Rob, what's the next five years for you and for Scoop? Paint that vision for me.

A Sure. So when we talk about the next five years, it comes down to how we think about our mission. Our mission is bring commuters together and carpools they'll love by partnering with their employers across the country. And so our focus in the near term is how do we deliver better and better carpoolers Make sure that when you want to take a trip, you always can, that you love the people that you share that trip with and the experience of doing it, and that we continue to work with more and more employers, companies like LinkedIn, T-Mobile, Workday, expanding our relationships, and then new employers across the country to have more and more impact. In a longer time horizon, I think to five years, we want to solve more and more of the challenges that enterprises struggle with when it comes to the commute. How do they have better insights into how their people are getting to work? How that impacts recruitment, retention, and engagement. What are the areas where we've actually solved commute problems if I think about particular origins around an employer? And what are the areas that actually are still trouble spots for us so that we can be a trusted partner and really advisor to companies that think about how do we turn the commute from a challenge or a source of cost or pain for us into something that actually is strategic advantage and we can differentiate our employee experience

AI assessment note: “In a longer time horizon, I think to five years, we want to solve”

Q You said about that, the decisions, and once they're made, and then kind of maybe the flexibility to change them. When I chatted to Danny Reimer, he said to me about the strategic elements of the company, and he asked, how does strategy influence what you're doing, and how often do you think about strategy re-evaluation?

A I would say I do probably a major evaluation of where we're at, where we're going, probably every six months. I try not to re-evaluate strategy too often. I think if you're changing strategy every week or Two weeks or month, It actually creates whiplash for the team. People feel like there's not a consistent point of view. We're not clear on where we're going. Part of the work that we did early on to really establish how to think about strategy was thinking through what is our vision and our mission as an organization and getting that to a place where when we talk about mission and every single quarter, when we do a review in front of the company, we always start by repeating the mission to everybody. We can make sure that that's real guardrails for how we think about strategy. That if we're creating the right priorities, if we're thinking about the right decisions, they should drive us toward accomplishing our mission. If our strategy or our investments are not aligned with that, then we know we're not headed the right direction. And so some of it is creating the right guardrail so you don't have to revisit all the time. But still, realities change often, as we discussed earlier, and I think you do have to make time to revisit on a regular basis. We do it probably about every six months.

AI assessment note: “I do probably a major evaluation of where we're at... probably every six months.”

Q No, I love that kind of a segmentation and breakdown there of the core problems that one faces. My big question on decisions is always kind of the foundational. I think it's inherent within a lot of decisions. It's when does one trust their heart versus their head in decision-making as a founder? How do you approach that difficult balance?

A I think it depends a lot on the stage of the company, honestly, and the type of topic. Early on, when I think about when we were preparing to raise our seed round, when we were just doing diligence on the concept of scoop and carpooling broadly, I spent much more time in the head than in the heart, in that sense. Like, a lot of it are understanding how do people commute today? What does that look like across the United States? What are their alternatives? Why do we think we can build a better alternative? How do we think about building a business against that over time? Once that shifted, and we raised capital and really started to build, speed became very important. The ability to accelerate through decisions, to do things, even if you only have 50% or 70% conviction or data, actually becomes deeply important. And so, there are times, I think, in the life cycle of a company, especially early on, where Heart and gut and saying, look, I have a pretty strong feeling this is the right answer. Maybe I can stitch together a little bit of data. I can certainly track the performance of a decision over time, but moving fast can be more important than actually moving exactly right and being decisive can actually be more important than being a hundred percent in your decision-making. And that's been a big focus for us over time to make sure that we stay nimble as we scale.

AI assessment note: “I think it depends a lot on the stage of the company, honestly”

Q being uncomfortable. We say, kind of, about radically transparent to the extreme, which leads to some interesting conversations, as you can imagine. Speaking of the decision makers, though, kind of, the board obviously also play a role in shaping some decisions. I spoke to Victoria Prelude before the show, and she asked, how should founders best partner with their board to drive key goals, and what's really worked for you?

A I think the best way to partner with a board is to treat them as if they are on your side of the table. The biggest challenge that I hear quite often for founders and working with board members is when they start to set up board meetings and their engagement with the board as if it's a dog and pony show. You don't want to talk about what's wrong with the company. You don't want to actually clue the board into challenges. The board members, if they're good board members, have seen lots of different companies over time. They know from their own companies or funds or wherever else they've been involved in that not everything goes right a hundred percent of the time. And so the more you try and pull the wool over the eyes of your board members, not let them like into what's actually happening, that's actually what breeds distrust and pain and creates really difficult board conversations. The way that we've approached it over time is we think about board meetings as a opportunity to say, look, there are a lot of things that are going well with the company. You know, we're growing fast. The company is doing well. Headcount is scaling really aggressively. We have really great marquee customers. Here are two or three things that are broken. We need to go focus on A, on B, on C. Let's spend the vast majority of our time working through that. I'll share my point of view on what our plan …

AI assessment note: “I think the best way to partner with a board is to treat them as if”

Q Speaking about the people that do need to revisit those strategies, Taking kind of that little step back and focusing on the founders that make those decisions now. Your co-founding relationship is unique with your co-founder also being your brother. Tell me, what are the dynamics of working with your brother day to day?

A Well, 80 or 90% of the time I would tell you it's great. I would say 10 or 20% of the time we'll have an argument. I'm not sure if we're arguing about something that happened 25 years ago in our childhood that we just never actually got over or if it's actually about something that's going on at work. But in all seriousness, I think the thing that is most important as a founder finding another founder as a co-founder is you have to deeply implicitly trust that that person is on your team because building companies is hard and you have great days and you have tough days and you go through really good cycles and bad cycles. You have to believe that the person you're working with at the end of the day is going to act in your mutual best interest, that they're really on your side and For me, that's the greatest privilege in working with my brother. I know that we're aligned in where we're going. I know that we have each other's best interests in mind and at heart, and that creates a tremendous amount of strength and comfort as we think about building a company.

AI assessment note: “80 or 90% of the time I would tell you it's great”

Q Can I ask you a question on the board chemistry between the founder and it's now for me as a VC, what can VCs do to change that Pony show that happens with board meetings often to a real relationship of trust and radical transparency. What can we do to create that environment for you, the founder?

A I think there's a couple of things. One, I think trust starts with alignment around vision for the company. That is something that I think gets started, or at least that pathway begins in the actual diligence process when you're first meeting investors or investors or first meeting founders. Making sure that there's common vision on exactly where the company should Go. You know, for us, that's been super clear over time in terms of the mission of what we're trying to do and our board members buy-in that that is the right thing to accomplish. That's the foundation. If you don't see the world the same way, you don't see the future of the company the same way, there's no real way to build trust between the board and the founders, and that's a conversation that has to happen before any other, in my opinion. Beyond that, as board members, I think it's really important to show founders that they can bring sensitive topics to And something that's wrong with the company and not get hammered for it. To actually say, look, I'm glad you brought this to us. Like, this is something that a lot of our founders have struggled with over time. Let's work on how we do that together or how we think through this. That creates a repeatable behavior or comfort with the idea that, oh, I actually can be honest with the board. That they're not going to say, oh, I'm a terrible CEO. I should be thrown out…

AI assessment note: “show founders that they can bring sensitive topics to And something that's wrong”

Q Can I ask, I've got an angel investment now, and the two founders are struggling over the hat-wearing element and how segmented it should be. One does product, the other does business strategy, one does fundraising, the other does hiring. How important do you think segmentation of different functions is between founders?

A I think it's incredibly important. I think that there are founders who believe when it's really early stage that that feels overly bureaucratic, but it actually festers. Over time, if you don't fix it, role clarity is not just important for the two of you or three of you or however many people it might be as founders. It's critically important for the team because what ends up happening is people don't know who to go to. If I've got a question, who actually answers that question? Do we have to make decisions by consensus or can one of you actually weigh in on that topic? The organizational pain and slowness that comes from that over time is actually the biggest barrier. That's the real challenge that comes up. And so my advice would be, be uncomfortably direct. It's also one of our values being open, honest, and direct. Be uncomfortably direct early on with each other. Who's going to get involved in what? Who owns what decision? What things are we going to work on together, like forming the culture and values and hiring? What are the things that we're going to work on separately, like product versus business strategy? I think actually having that conversation, even if it feels forced and bureaucratic early on, actually pays huge dividends over the life cycle of the company.

AI assessment note: “I think it's incredibly important.”

Q I mean, that is super fascinating, both in Time element and then the lack of data that one also sometimes has when making decisions. If we take the time element first, time pressure always a big factor in decisions. How are you able to carve out the time and prioritize focusing on key decisions versus maybe being overwhelmed by running a company?

A I think part of it is trying to make sure that I limit the exact number of decisions that I need to make. Part of building a company and candidly a huge part of the way we think about building our culture is companies are a collection of people. Right. It's actually getting a team and then larger and larger teams to be able to run in the same direction, to believe the same things, to invest along the same path. And so part of our ability to develop people and actually strengthen our market position, our product, the things that we need to do to be successful is empowering them to make decisions. How do I make sure that our leaders feel empowered to own the areas in which they operate? A source of guidance or input or strategic advice, but ultimately not all decisions flow up to me. That allows me to really focus and say, look, there's only three or four or five things at a given time for the company that actually I should be spending time on. Everything else, people on my team should own, our leaders or other team members should own, and that creates a lot of space for the right people to make the right decisions.

AI assessment note: “limit the exact number of decisions that I need to make”

Q spoke about decisions first as kind of the central thesis, then we moved down to the kind of founders and the board that make them. Speaking about the employees and team now that kind of Execute on those decisions. When we chatted before, you said you have to maintain a culture of betting on yourself and the team as the company grows. Can I ask, how do you do this?

A So betting on ourselves and the team is one of our values, and for us, what betting on ourselves and the team means is we do not historically try and hire folks that have done something four times or five times or six times before and are interested in doing it a seventh. We've been much more interested in building team with folks that actually are really high performers, probably weren't actively looking for another opportunity and are asking themselves, what can I really accomplish if I'm given the space, if I really put my mind to it? And then I think about how do I bring those people on board and invest as aggressively in them as possible to say, what could you actually do? Like, what's your potential? How do we make it possible for you to scale as fast as you possibly can? So it's ingrained into our values and our culture that way. To do that correctly, I think you have to be very feedback, and to your point earlier, uncomfortably honest, and so two of our other values are, one, being open, honest, and direct, as I mentioned, and two, something we call give a good push, which is a thing that we say at Scoop to push each other to think differently, to stretch your point of view, to encompass other people's perspective, and that allows us to have the space to be able to have the conversation that's required to actually bet on people and have the And so that's a little bit of…

AI assessment note: “It comes through in professional development and the way that we work”

Q Taking this kind of one step logically further, attrition is one of the biggest problems for anyone on the West Coast today. You've got next to zero attrition, according to Zora Signia. What do you think is the key to this, and I'd love to hear, how do you see the employment market today?

A Well, the employment market is incredibly tight. And I expect it will continue to be that way. It's a huge driver actually of our business overall, not just in technology, but across the country that it is so difficult to recruit and retain top talent. And there's a scarcity of skilled labor and a whole bunch of different categories. And so that's something that I think is true, not just for our world and in technology, but really across the board. When I think about what it means to build a team that actually can last and that people want to stay at a company long-term, I think it starts with authenticity and And really deep caring about your people. You know, as I mentioned before, we start in the very interview process, making sure that what people want to do, what they want to accomplish over the next few years is aligned with what we can deliver. Once someone starts at scoop, we have that conversation constantly. It takes place in one-on-ones with their manager. It takes place in skip level one-on-ones with the person above them. It takes place in professional development. And we do a review cycle every six months to talk about how Where are you at? Where do you want to go? What are the skills you have to build to get there? And constantly evaluating not just how people are doing professionally, but also personally. How ingrained do they feel in the culture? What is their …

AI assessment note: “starts with authenticity and And really deep caring about your people.”

Q No, I love that kind of a segmentation and breakdown there of the core problems that one faces. My big question on decisions is always kind of the foundational. I think it's inherent within a lot of decisions. It's when does one trust their heart versus their head in decision-making as a founder? How do you approach that difficult balance?

A I think it depends a lot on the stage of the company, honestly, and the type of topic. Early on, when I think about when we were preparing to raise our seed round, when we were just doing diligence on the concept of scoop and carpooling broadly, I spent much more time in the head than in the heart, in that sense. Like, a lot of it are understanding how do people commute today? What does that look like across the United States? What are their alternatives? Why do we think we can build a better alternative? How do we think about building a business against that over time? Once that shifted, and we raised capital and really started to build, speed became very important. The ability to accelerate through decisions, to do things, even if you only have 50% or 70% conviction or data, actually becomes deeply important. And so, there are times, I think, in the life cycle of a company, especially early on, where Heart and gut and saying, look, I have a pretty strong feeling this is the right answer. Maybe I can stitch together a little bit of data. I can certainly track the performance of a decision over time, but moving fast can be more important than actually moving exactly right and being decisive can actually be more important than being a hundred percent in your decision-making. And that's been a big focus for us over time to make sure that we stay nimble as we scale.

AI assessment note: “I think it depends a lot on the stage of the company, honestly”

Q I'm sure it also builds a culture of kind of accountability and responsibility that people love. On the element of data though, my partner at Fred Destin is also a huge note when it comes to the decision making, and he said before that decisions are never perfect. As a founder, what you're playing for is batting average. How do you think about that, and would you agree with him?

A I would fully agree with that. It's a funny thing that I talk about with my team is, look, you shouldn't assume that every decision I make is going to be right, but for Scoop to be successful, I have to be right a whole lot more often than I'm wrong over time for us to do what we need to do, and so I think it's in And that if you don't have a hundred percent information, you're not always going to make the right decision. And even if you did have a hundred percent information, realities change on the ground. People react in different ways than you intended. That's part of why experimentation is actually deeply important. I think the goal is to make decisions quickly and try and maximize for lack of better description, the product of how fast am I making decisions times how often am I right? That's really what you're trying to solve for.

AI assessment note: “I would fully agree with that. It's a funny thing that I talk about”

Q Can I ask, I've got an angel investment now, and the two founders are struggling over the hat-wearing element and how segmented it should be. One does product, the other does business strategy, one does fundraising, the other does hiring. How important do you think segmentation of different functions is between founders?

A I think it's incredibly important. I think that there are founders who believe when it's really early stage that that feels overly bureaucratic, but it actually festers. Over time, if you don't fix it, role clarity is not just important for the two of you or three of you or however many people it might be as founders. It's critically important for the team because what ends up happening is people don't know who to go to. If I've got a question, who actually answers that question? Do we have to make decisions by consensus or can one of you actually weigh in on that topic? The organizational pain and slowness that comes from that over time is actually the biggest barrier. That's the real challenge that comes up. And so my advice would be, be uncomfortably direct. It's also one of our values being open, honest, and direct. Be uncomfortably direct early on with each other. Who's going to get involved in what? Who owns what decision? What things are we going to work on together, like forming the culture and values and hiring? What are the things that we're going to work on separately, like product versus business strategy? I think actually having that conversation, even if it feels forced and bureaucratic early on, actually pays huge dividends over the life cycle of the company.

AI assessment note: “I think it's incredibly important.”

Q Can I ask you a question on the board chemistry between the founder and it's now for me as a VC, what can VCs do to change that Pony show that happens with board meetings often to a real relationship of trust and radical transparency. What can we do to create that environment for you, the founder?

A I think there's a couple of things. One, I think trust starts with alignment around vision for the company. That is something that I think gets started, or at least that pathway begins in the actual diligence process when you're first meeting investors or investors or first meeting founders. Making sure that there's common vision on exactly where the company should Go. You know, for us, that's been super clear over time in terms of the mission of what we're trying to do and our board members buy-in that that is the right thing to accomplish. That's the foundation. If you don't see the world the same way, you don't see the future of the company the same way, there's no real way to build trust between the board and the founders, and that's a conversation that has to happen before any other, in my opinion. Beyond that, as board members, I think it's really important to show founders that they can bring sensitive topics to And something that's wrong with the company and not get hammered for it. To actually say, look, I'm glad you brought this to us. Like, this is something that a lot of our founders have struggled with over time. Let's work on how we do that together or how we think through this. That creates a repeatable behavior or comfort with the idea that, oh, I actually can be honest with the board. That they're not going to say, oh, I'm a terrible CEO. I should be thrown out…

AI assessment note: “show founders that they can bring sensitive topics... and not get hammered for it”

Q a, on a theme that's a real passion for both of us, decision-making. As I said, I spoke to many of your investors, and the commonality in the discussion was where you excel in decision-making. So, Brooke Porter mentioned your unique ability in how you approach key decisions. Let's start out on that. How do you approach And what does he mean when he says from a first principles perspective?

A A lot of how I think about decision-making actually comes from my time at Bain. So I spent six and a half years doing strategy consulting before I joined Scoop. And I think consulting, it gives you a really good approach to how do you break down complex problems into really simple elements. And to me, when I think about Building a business at the end of the day, building a business is a set of problems that you have to think through and solve. And any problem that you're trying to solve, you can break down into what are the questions we have to answer? What's the work I have to do to actually answer that question, executing that work, and then communicating the outcome and doing something about it. And so whenever I'm trying to make big decisions, or as a company, we think through this, always go back to first principles, digest that problem down and Think it through in pieces. We work very closely with our board and others to give feedback and input, but that served me very well, and it comes from prior experiences to scoop.

AI assessment note: “break down complex problems into really simple elements”

Q I mean, that is super fascinating, both in Time element and then the lack of data that one also sometimes has when making decisions. If we take the time element first, time pressure always a big factor in decisions. How are you able to carve out the time and prioritize focusing on key decisions versus maybe being overwhelmed by running a company?

A I think part of it is trying to make sure that I limit the exact number of decisions that I need to make. Part of building a company and candidly a huge part of the way we think about building our culture is companies are a collection of people. Right. It's actually getting a team and then larger and larger teams to be able to run in the same direction, to believe the same things, to invest along the same path. And so part of our ability to develop people and actually strengthen our market position, our product, the things that we need to do to be successful is empowering them to make decisions. How do I make sure that our leaders feel empowered to own the areas in which they operate? A source of guidance or input or strategic advice, but ultimately not all decisions flow up to me. That allows me to really focus and say, look, there's only three or four or five things at a given time for the company that actually I should be spending time on. Everything else, people on my team should own, our leaders or other team members should own, and that creates a lot of space for the right people to make the right decisions.

AI assessment note: “limit the exact number of decisions that I need to make”

Q Speaking about the people that do need to revisit those strategies, Taking kind of that little step back and focusing on the founders that make those decisions now. Your co-founding relationship is unique with your co-founder also being your brother. Tell me, what are the dynamics of working with your brother day to day?

A Well, 80 or 90% of the time I would tell you it's great. I would say 10 or 20% of the time we'll have an argument. I'm not sure if we're arguing about something that happened 25 years ago in our childhood that we just never actually got over or if it's actually about something that's going on at work. But in all seriousness, I think the thing that is most important as a founder finding another founder as a co-founder is you have to deeply implicitly trust that that person is on your team because building companies is hard and you have great days and you have tough days and you go through really good cycles and bad cycles. You have to believe that the person you're working with at the end of the day is going to act in your mutual best interest, that they're really on your side and For me, that's the greatest privilege in working with my brother. I know that we're aligned in where we're going. I know that we have each other's best interests in mind and at heart, and that creates a tremendous amount of strength and comfort as we think about building a company.

AI assessment note: “80 or 90% of the time I would tell you it's great.”

Q being uncomfortable. We say, kind of, about radically transparent to the extreme, which leads to some interesting conversations, as you can imagine. Speaking of the decision makers, though, kind of, the board obviously also play a role in shaping some decisions. I spoke to Victoria Prelude before the show, and she asked, how should founders best partner with their board to drive key goals, and what's really worked for you?

A I think the best way to partner with a board is to treat them as if they are on your side of the table. The biggest challenge that I hear quite often for founders and working with board members is when they start to set up board meetings and their engagement with the board as if it's a dog and pony show. You don't want to talk about what's wrong with the company. You don't want to actually clue the board into challenges. The board members, if they're good board members, have seen lots of different companies over time. They know from their own companies or funds or wherever else they've been involved in that not everything goes right a hundred percent of the time. And so the more you try and pull the wool over the eyes of your board members, not let them like into what's actually happening, that's actually what breeds distrust and pain and creates really difficult board conversations. The way that we've approached it over time is we think about board meetings as a opportunity to say, look, there are a lot of things that are going well with the company. You know, we're growing fast. The company is doing well. Headcount is scaling really aggressively. We have really great marquee customers. Here are two or three things that are broken. We need to go focus on A, on B, on C. Let's spend the vast majority of our time working through that. I'll share my point of view on what our plan …

AI assessment note: “best way to partner with a board is to treat them as if they are”

Q spoke about decisions first as kind of the central thesis, then we moved down to the kind of founders and the board that make them. Speaking about the employees and team now that kind of Execute on those decisions. When we chatted before, you said you have to maintain a culture of betting on yourself and the team as the company grows. Can I ask, how do you do this?

A So betting on ourselves and the team is one of our values, and for us, what betting on ourselves and the team means is we do not historically try and hire folks that have done something four times or five times or six times before and are interested in doing it a seventh. We've been much more interested in building team with folks that actually are really high performers, probably weren't actively looking for another opportunity and are asking themselves, what can I really accomplish if I'm given the space, if I really put my mind to it? And then I think about how do I bring those people on board and invest as aggressively in them as possible to say, what could you actually do? Like, what's your potential? How do we make it possible for you to scale as fast as you possibly can? So it's ingrained into our values and our culture that way. To do that correctly, I think you have to be very feedback, and to your point earlier, uncomfortably honest, and so two of our other values are, one, being open, honest, and direct, as I mentioned, and two, something we call give a good push, which is a thing that we say at Scoop to push each other to think differently, to stretch your point of view, to encompass other people's perspective, and that allows us to have the space to be able to have the conversation that's required to actually bet on people and have the And so that's a little bit of…

AI assessment note: “It comes through in professional development and the way that we work and the way that we hire.”

Q What would you most like to change about Silicon Valley and tech ecosystem today?

A I think the way that we reflect or the way that we are viewed across the rest of the country. I think in the last few years, there's been a number of issues that have popped up that have made technology leaders look like They're out of touch. They don't understand the ramifications of the work that we do, the issues that data and privacy concerns actually are real big concerns, and that the everyday person actually really does care about that, and that we do believe in making the world a better place, not just building things that are interesting to make money. That, in my mind, is the most important thing to change, and that's one of the reasons I love building Scoop is because it's so aligned with that concept.

AI assessment note: “the way that we reflect or the way that we are viewed”

Q What would you most like to change about Silicon Valley and tech ecosystem today?

A I think the way that we reflect or the way that we are viewed across the rest of the country. I think in the last few years, there's been a number of issues that have popped up that have made technology leaders look like They're out of touch. They don't understand the ramifications of the work that we do, the issues that data and privacy concerns actually are real big concerns, and that the everyday person actually really does care about that, and that we do believe in making the world a better place, not just building things that are interesting to make money. That, in my mind, is the most important thing to change, and that's one of the reasons I love building Scoop is because it's so aligned with that concept.

AI assessment note: “I think the way that we reflect or the way that we are viewed”