YouSaid · the spoken record

Spike Lipkin

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25
first
2020-10-16
most recent
2020-10-16
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1
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podcast

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  1. “In our experience, if you leverage technology to provide a differentiated client experience, you often can also leverage technology to provide differentiated margins. So I think it may not be the world of 99% gross margins that Google experience, but it will be the world of entering very, very large industries and improving the economics of those industries and also improving the client experience.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  2. “If the last phase of technology was characterized by companies selling technology, I think the next phase will be characterized by technology companies selling services. Technology is in our world today, and I think the next set of breakaway companies are going to leverage technology to provide a differentiated client experience.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  3. “So, my co founder Gordon's father was an insurance industry executive, and he pulled together this group of financial services execs who Angel invested in our company. We affectionately call them the Sharks, and they constantly remind us how much work we have to do, help us understand some of the metrics and our comparables. So they've been crucial to our success. The other one is Michael Ovitz. He built CAA, which is the largest talent agency in Hollywood. We've learned a huge amount from him about how to build our culture and team at Newfront.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  4. “My real name's Eugene, named after my grandfather. My parents started calling me Spike since I was born because my hair was always sticking up.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  5. “Team of rivals by Doris Kearns Goodwin. It's incredibly inspiring how a group of people who didn't see eye to eye work so well together.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  6. “Very nice of him to say because when Kevin invested, we had some other offers that were materially higher than his. I think his was 30% lower than the next offer. So I actually think Kevin is the pro here. That's a nice thing of him to say, but I think he's the real negotiation pro”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  7. “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 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.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  8. “So I think we've been lucky in that we've been able to hire people based on our mission and the traction of our business. So we haven't necessarily needed the external validation of funding to fuel hiring. We've also been really thankful for intros from investors, even if we're not public about who our investors are. They've been great at funneling incredible people our way.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  9. “I heard the founder of Qualtrics speak years ago, and they were a bootstrap business, and he talked about how weird it was that when they first raised money, everyone congratulated him. He pointed out that no one congratulated him when he got his mortgage. While financings are a nice external validation, we've wanted to celebrate business successes, not financings. I think that's one part of it. The other part of it is that we've wanted to standard the radar until we get to a scale so as not to invite competition. I think that will likely change soon as we want to start building a brand and showing our scale, but that's been our historical approach.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  10. “We've optimized for finding investors that can help us de risk core parts of our business. So as we were scaling new front, we wanted to learn from one of the best operators out there. And so we were lucky enough to work with Kevin Harts and met with him once a week for a number of years to think through some of the common challenges of scaling, recruiting incredible people, building out common processes at Newfront. And so we have other investors who've helped us de-risk other parts of the business, but we've thought about bringing on investors that can help us solve a discrete problem in the business.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  11. “Our approach has been to work with a small number of investors and take a very targeted approach. We've been lucky that our last three funding rounds have been preemptive, and mostly it's been insiders wanting to lead subsequent rounds. And so what we've done is we've asked friends which investors they respect most, and then we've optimized for working with those people. We work really closely with our investors early on for about the first two years of the company, we sent weekly metrics to one of our investors. We also made the conscious decision to restrict outside investor meetings so that we can focus on the business. Last year in 2019, I think I met with one investor who's not on our cap table right now. Our view is that if we build a great business, the rest will take care of itself.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  12. “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 New Front, 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.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  13. “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.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  14. “I don't think it's me. I think it's the potential to improve a mission critical industry that affects every business. I think it's the potential to make it easier for our clients to innovate and create jobs. I think it's the potential to create a platform for our brokers that helps them serve their clients and achieve financial freedom. I think those are the things that motivate our team. And if there's anything I do, it's get out of the way so that they can do the great work they're doing.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  15. “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 but certainly one that's been difficult for me.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  16. “A lot of things broke. I think we outscaled many of the systems we had in place early on. I think some of the right decisions, which were not obsessing about creating the perfect system, but really growing the business so that we can learn and improve our product and eventually improve our systems. And so we were running a scaled customer service org without a ticketing system, for instance. We didn't have SLAs in place. And so it felt like there were some common best practices from larger orgs that we could pull in. We had an incredible team that was bringing those things and putting those things in place, but bringing Mike in just accelerated our progress towards those goals.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  17. “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 opsorg. 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.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  18. “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 Newfront that the folks who were currently in the ops org were just excited to learn from him. I mean, it was so clear that we could all up-level 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.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  19. “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.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  20. “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 Newfound. Pretty quickly thereafter my role changed from being scratched.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  21. “We did this exercise early on where a lot of the execs on my team wrote down a list of things that gave them energy and that they loved doing and felt like they were very good at and things that took energy from them and they didn't enjoy doing and didn't feel like they were particularly good at. And one of the interesting things was there was not a lot of overlap on those lists. And so one person loved sales work and closing candidates, another person loved more analytical work. And so we kind of figured out how to divide up the jobs to be done at Newfront based on what people love doing and felt self-actualized in doing and things that took a lot of energy from people and they didn't feel like they were particularly good at. And so we kept our shoes on. We don't have a cultural norm like that. It's more just figuring out what's going to make people leap out of bed in the morning to go to work and what takes a lot of energy from them and they don't feel like they're particularly good at.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  22. “That's very kind of Gordon. It sounds like you maybe also talk 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.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  23. “My co-founder, Gordon and I have talked a lot about this in 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 times, we find someone much more capable than us to grow up the systems and build a 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.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  24. “Being early at Open Door 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 OpenDor was building a great company as 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 OpenDOR 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.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source

  25. “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 Open Door and worked on some of the initial insurance at OpenDor, 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 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.”

    2020-10-16 · The Twenty Minute VC · 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance · IDENTIFIED FROM THE TRANSCRIPT · source