The Exchanges

Q I'm so pleased you mentioned Mike, because Max and the investor base all said just what an incredible caliber of acquisition he was for you and the company. Question for me was, why did you decide to hire the COO, and why was then the right time?

A Yeah, so as our business grew, we wanted to bring on someone who'd seen complex operational orgs get built. We think a lot about the risks we're taking as a business, and we want to innovate on client experience and broker experience. We didn't want to innovate on creating a best-in-class ops org. We felt like this was not an area where we needed to reinvent the wheel. Our board member, Kevin Hartz, introduced us to Mike Brown and said, before you start interviewing for this role, you should meet one of the best, and the way we got to know Mike is we invited him to one of our ops meetings, and I think it was this meeting where literally every metric looked bad, but what Mike saw was a business that was growing rapidly with a set of business problems that he uniquely could solve. He's been an amazing partner for me. I've learned a huge amount from him, and he's also freed me up to focus on other parts of the business, so the timing for us was really around when operations became a Crucial bottleneck in the business, and it felt like bringing in someone who had done it before would allow us to accelerate the business.

AI assessment note: “timing for us was really around when operations became a Crucial bottleneck in the business”

Q Can I ask, and you have brought in some truly incredible execs. A big question for me that I always think when bringing in incredible execs is how do you manage the team internally when you have an internal team member who really is wanting that promotion? And how do you balance that internal promotion versus the external hire? How do you think about that?

A I think we've tried to find people who many of us would be thrilled to work for. So one of those positions that we filled is the chief operating officer position. And we hired Mike Brown, who came to us from running a large part of Uber in Asia. And I think we were all so thrilled at the prospect of Mike Brown joining new front that the folks who were currently in the ops or were just excited to learn from him. I mean, it was so clear that we could all uplevel our game, improve our business and all become better leaders by having him join. And so at that point, it was sort of a no brainer.

AI assessment note: “we've tried to find people who many of us would be thrilled to work for”

Q I'm so pleased you mentioned Mike, because Max and the investor base all said just what an incredible caliber of acquisition he was for you and the company. Question for me was, why did you decide to hire the COO, and why was then the right time?

A Yeah, so as our business grew, we wanted to bring on someone who'd seen complex operational orgs get built. We think a lot about the risks we're taking as a business, and we want to innovate on client experience and broker experience. We didn't want to innovate on creating a best-in-class ops org. We felt like this was not an area where we needed to reinvent the wheel. Our board member, Kevin Hartz, introduced us to Mike Brown and said, before you start interviewing for this role, you should meet one of the best, and the way we got to know Mike is we invited him to one of our ops meetings, and I think it was this meeting where literally every metric looked bad, but what Mike saw was a business that was growing rapidly with a set of business problems that he uniquely could solve. He's been an amazing partner for me. I've learned a huge amount from him, and he's also freed me up to focus on other parts of the business, so the timing for us was really around when operations became a Crucial bottleneck in the business, and it felt like bringing in someone who had done it before would allow us to accelerate the business.

AI assessment note: “the timing for us was really around when operations became a Crucial bottleneck”

Q I would love to kick off this day with a little bit on you. So Max mentioned to me that you have an authentic founding journey. So tell me about that. How did you make your way into the world of startups first, but then what was that authentic founding journey founding Newfront?

A Yeah. So prior to starting Newfront, I had a fair amount of firsthand experience buying property and casualty insurance. So early in my career, I worked at Blackstone and inherited a lot of the responsibilities no one else wanted. And high on that list was buying insurance for a company that we were working with. And I remember dealing with this mountain of paperwork, filling out all these forms, waiting seven weeks, getting back these really confusing options, and just being shocked at how confusing this process is that's so core to American business. Left Blackstone, was lucky to join Opendoor, and worked on some of the initial insurance at Opendoor, and it was the same thing. Mountains of paperwork, really confusing options. And so at some point, I just became obsessed with this idea that insurance was crazy. Crucial to our society, crucial to our economy, crucial to entrepreneurship, and really understood by no one. So got obsessed and decided that I wanted to start a company in the space to help modernize the industry, make it easier for businesses to buy and manage insurance. And so it felt like a circuitous route, but insurance was this kind of persisting pain point and kind of burning need in the back of my head for the time leading up to starting Newfront.

AI assessment note: “got obsessed and decided that I wanted to start a company in the space”

Q Can I ask, it's off schedule, so I apologize for this, but it's something that I struggle with. I like to say yes and do most things. How do you determine what to delegate and what to really allocate your time towards? What's that determination process?

A Yeah, my co-founder Gordon and I have talked a lot about this at Newfront, and we think of our jobs at Newfront as solving unsolved problems and then finding people more capable than us to run parts of the business. And so in every part of the business, we like to be the first one to do something. So we like to be the first one to figure out how we should answer customer success tickets. And then after we've done it a couple of times, we find someone much more capable than us to grow up the systems and build the process going forward. And so we try not to delegate zero to one problems. We try to solve those ourselves and then very quickly find capable people to delegate those things to.

AI assessment note: “we try not to delegate zero to one problems. We try to solve those ourselves”

Q Can I ask, in terms of that, like, what gives them energy versus what doesn't, roles change over time. I'm interested, how have you seen your role change and develop over the years with Newfront?

A Early on, my role was very focused on getting things done. I cold called a lot of our initial brokers, set up a lot of our initial systems, and the challenge for me has been making sure that I scale at the rate of Newfront. Pretty quickly thereafter, my role changed from being scrappy and doing a lot of things myself to recruiting incredible people. What's been amazing is a lot of the early team members we recruited were We're very entrepreneurial. Some of them have even gone on to start their own companies. The next thing I had to learn was how to recruit leaders, how to recruit incredible execs and give them autonomy. I think I've benefited a lot from coaches and advisors. I've worked with two different coaches, Matt Moshari and Joe Greenstein. We have an advisor named Linghua Wu, who's been incredibly helpful. Kevin Hartz, Annabelle Lippincott, Roy Bahat. These are all people that I've turned to for advice and learned a great deal from.

AI assessment note: “my role changed from being scrappy and doing a lot of things myself to recruiting”

Q Can I ask, you mentioned the decision making there. In terms of, like, decision making, risk is always an inherent part of it. How do you think about your own, kind of, relationship to risk, really?

A Yeah, when we think about risk, we're of course in the business of risk management, we think a lot about the types of risks we're taking. So, at Newfront, we want to take innovation risk on the client experience and the broker experience, But we don't necessarily want to take risk on some of the other core functions in the business. So for instance, we hired an incredible people leader, Heather Dunn, because we didn't want to reinvent the wheel on HR. We wanted to learn from the best. I mentioned we brought on Mike Brown because we didn't want to reinvent the wheel on operations. We wanted to learn from the best. So for us, it's about taking calculated risks that will be rewarded by customers and brokers, and then making sure we learn from the best in other areas.

AI assessment note: “it's about taking calculated risks that will be rewarded by customers and brokers”

Q Can I ask, you mentioned the decision making there. In terms of, like, decision making, risk is always an inherent part of it. How do you think about your own, kind of, relationship to risk, really?

A Yeah, when we think about risk, we're of course in the business of risk management, we think a lot about the types of risks we're taking. So, at Newfront, we want to take innovation risk on the client experience and the broker experience, But we don't necessarily want to take risk on some of the other core functions in the business. So for instance, we hired an incredible people leader, Heather Dunn, because we didn't want to reinvent the wheel on HR. We wanted to learn from the best. I mentioned we brought on Mike Brown because we didn't want to reinvent the wheel on operations. We wanted to learn from the best. So for us, it's about taking calculated risks that will be rewarded by customers and brokers, and then making sure we learn from the best in other areas.

AI assessment note: “we want to take innovation risk on the client experience and the broker experience”

Q I would love to kick off this day with a little bit on you. So Max mentioned to me that you have an authentic founding journey. So tell me about that. How did you make your way into the world of startups first, but then what was that authentic founding journey founding Newfront?

A Yeah. So prior to starting Newfront, I had a fair amount of firsthand experience buying property and casualty insurance. So early in my career, I worked at Blackstone and inherited a lot of the responsibilities no one else wanted. And high on that list was buying insurance for a company that we were working with. And I remember dealing with this mountain of paperwork, filling out all these forms, waiting seven weeks, getting back these really confusing options, and just being shocked at how confusing this process is that's so core to American business. Left Blackstone, was lucky to join Opendoor, and worked on some of the initial insurance at Opendoor, and it was the same thing. Mountains of paperwork, really confusing options. And so at some point, I just became obsessed with this idea that insurance was crazy. Crucial to our society, crucial to our economy, crucial to entrepreneurship, and really understood by no one. So got obsessed and decided that I wanted to start a company in the space to help modernize the industry, make it easier for businesses to buy and manage insurance. And so it felt like a circuitous route, but insurance was this kind of persisting pain point and kind of burning need in the back of my head for the time leading up to starting Newfront.

AI assessment note: “decided that I wanted to start a company in the space to help modernize the industry”

Q Can I ask, it's off schedule, so I apologize for this, but it's something that I struggle with. I like to say yes and do most things. How do you determine what to delegate and what to really allocate your time towards? What's that determination process?

A Yeah, my co-founder Gordon and I have talked a lot about this at Newfront, and we think of our jobs at Newfront as solving unsolved problems and then finding people more capable than us to run parts of the business. And so in every part of the business, we like to be the first one to do something. So we like to be the first one to figure out how we should answer customer success tickets. And then after we've done it a couple of times, we find someone much more capable than us to grow up the systems and build the process going forward. And so we try not to delegate zero to one problems. We try to solve those ourselves and then very quickly find capable people to delegate those things to.

AI assessment note: “we try not to delegate zero to one problems. We try to solve those ourselves”

Q Can I ask, in terms of that, like, what gives them energy versus what doesn't, roles change over time. I'm interested, how have you seen your role change and develop over the years with Newfront?

A Early on, my role was very focused on getting things done. I cold called a lot of our initial brokers, set up a lot of our initial systems, and the challenge for me has been making sure that I scale at the rate of Newfront. Pretty quickly thereafter, my role changed from being scrappy and doing a lot of things myself to recruiting incredible people. What's been amazing is a lot of the early team members we recruited were We're very entrepreneurial. Some of them have even gone on to start their own companies. The next thing I had to learn was how to recruit leaders, how to recruit incredible execs and give them autonomy. I think I've benefited a lot from coaches and advisors. I've worked with two different coaches, Matt Moshari and Joe Greenstein. We have an advisor named Linghua Wu, who's been incredibly helpful. Kevin Hartz, Annabelle Lippincott, Roy Bahat. These are all people that I've turned to for advice and learned a great deal from.

AI assessment note: “Pretty quickly thereafter, my role changed from being scrappy and doing a lot of things”

Q Yeah, no, I definitely agree in terms of leveraging them for talent extraction. Do you have to ask, you mentioned Kevin there, and I know Kevin's on the board. Help me out here. It's really important for me that I can be the best board member that I can If you were advising me, what can I do to be the best board member to you, the founder?

A I think it's helping the founder think through the small set of things each quarter that will move the needle and de-risk the business and help the business move forward. And Kevin is laser focused on continuous progress. When we would meet with him weekly pre-COVID, we'd go to his house every Sunday, and he wouldn't have seen us for a week, but it would be very clear whether we'd made progress towards the initiative that we told him was most important in the prior week. So I think as founders and as employees, you're so deep in the weeds of solving business problems. And one of the advantages investors have is this bird's eye view where they can help founders identify, you know, the two or three most crucial elements of the business that need to be addressed. Kevin's been amazing at that. Max has been amazing at that. And so I think that's how great board members can help founders.

AI assessment note: “helping the founder think through the small set of things each quarter that will move the needle”

Q Yeah, no, I definitely agree in terms of leveraging them for talent extraction. Do you have to ask, you mentioned Kevin there, and I know Kevin's on the board. Help me out here. It's really important for me that I can be the best board member that I can If you were advising me, what can I do to be the best board member to you, the founder?

A I think it's helping the founder think through the small set of things each quarter that will move the needle and de-risk the business and help the business move forward. And Kevin is laser focused on continuous progress. When we would meet with him weekly pre-COVID, we'd go to his house every Sunday, and he wouldn't have seen us for a week, but it would be very clear whether we'd made progress towards the initiative that we told him was most important in the prior week. So I think as founders and as employees, you're so deep in the weeds of solving business problems. And one of the advantages investors have is this bird's eye view where they can help founders identify, you know, the two or three most crucial elements of the business that need to be addressed. Kevin's been amazing at that. Max has been amazing at that. And so I think that's how great board members can help founders.

AI assessment note: “helping the founder think through the small set of things each quarter that will move the needle”

Q of, like, going back to your leadership, you have these incredible strengths, and we're going to touch on one being the motivational element I heard about your offsite, by the way. We have the strengths. In terms of weaknesses, when you self-analyze, where are you like, you know what, this is a struggle, and I could do better here, and I guess, what are you doing to work on this?

A Yeah, I think we could spend the whole podcast talking about my weaknesses. I think one of the challenging things as CEO has been going from knowing every detail in our business and knowing everything that's going on to hiring people who are Far better than I am at understanding and leading their teams, and then being okay with not understanding every detail, and being okay with not going deep in the weeds. I think one of the things I'm working on is not going quite as deep on every part of the business, and freeing myself up to focus on new initiatives in the business, and allowing our execs to operate very, very autonomously. I think that's a hard transition for any founder, and it's certainly one that's been difficult for me.

AI assessment note: “one of the things I'm working on is not going quite as deep”

Q Can I ask, if you think about like what you've learned specifically when it comes to talent acquisition, are there elements that you really have taken with you and you take with you into every meeting with a potential candidate?

A Yeah, I think hiring incredible people is first about identifying them, and so whenever we've had an open role, we've asked folks for recommendations. Who is the best at X? And then we've gone and met with that person, and almost always that person tells us that they are unavailable or uninterested. And really for us, it's been articulating the mission of our company, finding that a lot of people, once we explain the mission, resonate with it, and then being quite open about the challenges facing the business. What we've found is that if we go talk to an incredible operator and Expose all the things that are broken in our business, but also show the things that are working. What gets them excited is the fact that they probably can solve the things that are broken and help improve the business. And so for us, it's been about mission and transparency, and that's what's led to, I think, recruiting the incredible team we have in place.

AI assessment note: “for us, it's been about mission and transparency”

Q thereafter. I mean, speaking of kind of zero to one, I spoke to Gordon before the show, and he said very specifically, the incredible thing about Spike is he's been the CEO that we've needed at each stage of the business. I was writing this question. I was like, gosh, this is a terrible question, but I want to ask it anyway. How would you describe your style of leadership?

A Well, that's very kind of Gordon. It sounds like you maybe also talked to my mom. But I very much view myself as a work in progress who's had the chance to learn from incredible coaches and leaders. When I think about the style of leadership that I aspire to, I think about something my parents used to tell me. One of the things they'd say is that the most important quality someone can have is bringing out the best in others. And so I think of my job and the job of any leader, really, as creating the environment for others to do great work. Across the board, we've hired people who know infinitely more about what they do than I do. And I think of my job as giving them autonomy and putting them in their zone of genius.

AI assessment note: “creating the environment for others to do great work”

Q Can I ask, if you think about like what you've learned specifically when it comes to talent acquisition, are there elements that you really have taken with you and you take with you into every meeting with a potential candidate?

A Yeah, I think hiring incredible people is first about identifying them, and so whenever we've had an open role, we've asked folks for recommendations. Who is the best at X? And then we've gone and met with that person, and almost always that person tells us that they are unavailable or uninterested. And really for us, it's been articulating the mission of our company, finding that a lot of people, once we explain the mission, resonate with it, and then being quite open about the challenges facing the business. What we've found is that if we go talk to an incredible operator and Expose all the things that are broken in our business, but also show the things that are working. What gets them excited is the fact that they probably can solve the things that are broken and help improve the business. And so for us, it's been about mission and transparency, and that's what's led to, I think, recruiting the incredible team we have in place.

AI assessment note: “for us, it's been about mission and transparency”

Q of, like, going back to your leadership, you have these incredible strengths, and we're going to touch on one being the motivational element I heard about your offsite, by the way. We have the strengths. In terms of weaknesses, when you self-analyze, where are you like, you know what, this is a struggle, and I could do better here, and I guess, what are you doing to work on this?

A Yeah, I think we could spend the whole podcast talking about my weaknesses. I think one of the challenging things as CEO has been going from knowing every detail in our business and knowing everything that's going on to hiring people who are Far better than I am at understanding and leading their teams, and then being okay with not understanding every detail, and being okay with not going deep in the weeds. I think one of the things I'm working on is not going quite as deep on every part of the business, and freeing myself up to focus on new initiatives in the business, and allowing our execs to operate very, very autonomously. I think that's a hard transition for any founder, and it's certainly one that's been difficult for me.

AI assessment note: “one of the things I'm working on is not going quite as deep”

Q is actually quite dangerous because I always think you'll always underestimate what you can do in that five to 10 year period. And so if I said to you within X amount of time, you would have achieved this. You've actually So much overshot that, that the vision almost undersells yourself. Would you agree with me, and how do you think about, like, the benefits versus the cons of mission?

A I think you're absolutely right. I mean, I will always overestimate what we get done in a quarter and seem to underestimate the cumulative effect of all the work we're doing over a year. I think there's some human psychology wrapped up in this. I think a vision and mission is really important as a north star for the team. So many decisions at a startup involve ambiguity and gray area. And having a very clearly articulated mission and having a very clearly articulated vision helps make some of those decisions that are difficult and somewhat gray. So it's been really important for our team. The other thing that's been important is having a lofty vision and then having a set of milestones and roadmap to achieve the lofty vision. And so one of the things I've been working on lately is we have a mission, we have a vision. What are the 20 building blocks to get there? And are those 20 building blocks achievable? It turns out when you write out here are the milestones that lead to our vision, The milestones seem pretty reasonable, and they seem like things our team can do, and when you check all the boxes in those milestones, you realize you're achieving the vision and mission you set out.

AI assessment note: “I think you're absolutely right. I mean, I will always overestimate”

Q Can I ask, and you have brought in some truly incredible execs. A big question for me that I always think when bringing in incredible execs is how do you manage the team internally when you have an internal team member who really is wanting that promotion? And how do you balance that internal promotion versus the external hire? How do you think about that?

A I think we've tried to find people who many of us would be thrilled to work for. So one of those positions that we filled is the chief operating officer position. And we hired Mike Brown, who came to us from running a large part of Uber in Asia. And I think we were all so thrilled at the prospect of Mike Brown joining new front that the folks who were currently in the ops or were just excited to learn from him. I mean, it was so clear that we could all uplevel our game, improve our business and all become better leaders by having him join. And so at that point, it was sort of a no brainer.

AI assessment note: “tried to find people who many of us would be thrilled to work for”

Q is actually quite dangerous because I always think you'll always underestimate what you can do in that five to 10 year period. And so if I said to you within X amount of time, you would have achieved this. You've actually So much overshot that, that the vision almost undersells yourself. Would you agree with me, and how do you think about, like, the benefits versus the cons of mission?

A I think you're absolutely right. I mean, I will always overestimate what we get done in a quarter and seem to underestimate the cumulative effect of all the work we're doing over a year. I think there's some human psychology wrapped up in this. I think a vision and mission is really important as a north star for the team. So many decisions at a startup involve ambiguity and gray area. And having a very clearly articulated mission and having a very clearly articulated vision helps make some of those decisions that are difficult and somewhat gray. So it's been really important for our team. The other thing that's been important is having a lofty vision and then having a set of milestones and roadmap to achieve the lofty vision. And so one of the things I've been working on lately is we have a mission, we have a vision. What are the 20 building blocks to get there? And are those 20 building blocks achievable? It turns out when you write out here are the milestones that lead to our vision, The milestones seem pretty reasonable, and they seem like things our team can do, and when you check all the boxes in those milestones, you realize you're achieving the vision and mission you set out.

AI assessment note: “I think you're absolutely right. I mean, I will always overestimate”

Q Can I ask, I'm always fascinated by takeaways. We had Julia DeWall on, who obviously was at Open Door with you. I'm really, in terms of like the lessons that you learned from the time when Open How did that experience impact your operating mindset and how you run Newfront today?

A Being early at Opendoor was an incredibly lucky experience for me. It was amazing to see just this extremely strong team rapidly iterating. One of the big takeaways was this keen focus on talent. When I looked at how Eric, Ryan, JD, Keith spent time, it was very much focused on recruiting incredible people. And so that was probably the biggest takeaway I had from my time at Opendoor was building a great company is so much about finding great People and having them align with your mission and join you. The other thing I saw there, which was interesting, was this focus on the most important problems, even if it meant leaving other fires burning. The nature of startups is that if they start working, you unlock resources and talent, and so, so many problems that seem hard today get easier over time, and I think Opendoor was kind of ruthlessly focused on solving the most important problems at the time, knowing that if they unblocked one problem, they'd have more resources and talent to solve the next problem.

AI assessment note: “One of the big takeaways was this keen focus on talent.”

Q Can I ask, I'm always fascinated by takeaways. We had Julia DeWall on, who obviously was at Open Door with you. I'm really, in terms of like the lessons that you learned from the time when Open How did that experience impact your operating mindset and how you run Newfront today?

A Being early at Opendoor was an incredibly lucky experience for me. It was amazing to see just this extremely strong team rapidly iterating. One of the big takeaways was this keen focus on talent. When I looked at how Eric, Ryan, JD, Keith spent time, it was very much focused on recruiting incredible people. And so that was probably the biggest takeaway I had from my time at Opendoor was building a great company is so much about finding great People and having them align with your mission and join you. The other thing I saw there, which was interesting, was this focus on the most important problems, even if it meant leaving other fires burning. The nature of startups is that if they start working, you unlock resources and talent, and so, so many problems that seem hard today get easier over time, and I think Opendoor was kind of ruthlessly focused on solving the most important problems at the time, knowing that if they unblocked one problem, they'd have more resources and talent to solve the next problem.

AI assessment note: “One of the big takeaways was this keen focus on talent.”

Q thereafter. I mean, speaking of kind of zero to one, I spoke to Gordon before the show, and he said very specifically, the incredible thing about Spike is he's been the CEO that we've needed at each stage of the business. I was writing this question. I was like, gosh, this is a terrible question, but I want to ask it anyway. How would you describe your style of leadership?

A Well, that's very kind of Gordon. It sounds like you maybe also talked to my mom. But I very much view myself as a work in progress who's had the chance to learn from incredible coaches and leaders. When I think about the style of leadership that I aspire to, I think about something my parents used to tell me. One of the things they'd say is that the most important quality someone can have is bringing out the best in others. And so I think of my job and the job of any leader, really, as creating the environment for others to do great work. Across the board, we've hired people who know infinitely more about what they do than I do. And I think of my job as giving them autonomy and putting them in their zone of genius.

AI assessment note: “creating the environment for others to do great work”