Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 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 About this episode Spike Lipkin is the Founder & CEO @ Newfront Insurance, the modern insurance brokerage empowering risk management experts with advanced technology to deliver innovative solutions to their clients'. To date, Spike has raised from some of the best in the business including Founders Fund, Meritech and 20VC Fund. Prior to founding Newfront, Spike was one of the first employees at Opendoor, where he helped grow the team from 5 people to an enterprise value of over $5Bn today. Prior to Opendoor, Spike was an investor at Blackstone, where he served on the startup team that built Invitation Homes into the largest owner of single-family real estate in the United States. In Today’s Episode You Will Learn: 1.) How Spike made his way from banking to be one of the first operators at Opendoor to founding the next generation of insurance with Newfront? 2.) What were some of the biggest takeaways for Spike from his time at Opendoor as employee #5? How does Spike approach prioritisation? How does he determine what to delegate vs what to control? 3.) How would Spike describe his own style of leadership? How has Spike needed to change his style with the business? What does Spike believe is his biggest weakness as a leader? What is he doing to confront it and grow as a leader? What is the most important thing a leader can do? 4.) How does Spike think about what it takes to acquire the very best talent? What does his framework for hiring look like? Why did Spike decide to hire a COO? Why was then the right time? How does Spike think about the balance between hiring external vs promoting internal? 5.) Why did Spike believe it was important not to announce any of his prior fundraises? How did Spike approach investor selection with Newfront? Does Spike believe founders should meet with VCs between fundraises? Which angel has done the most to move the needle for the company? How? Items Mentioned In Today’s Show: Spike’s Fave Book: Team of Rivals: The Political Genius of Abraham Lincoln As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Harry Stebbings? Welcome back to the 20 minute VC with me, Harry Stebbings. And today we have a guest I've wanted to have on the show for a long time. I'd heard quietly, under the radar about this company and what an incredible CEO our guest today is. But only today do we make our episode happen. And so with that, I'm very, very excited to welcome Spike Lipkin, founder and CEO at Newfront Insurance, the modern insurance brokerage empowering risk management experts with advanced technology to deliver innovative solutions to their clients. To date, Spike has raised over a hundred million dollars with Newfront from some of the best in the business, including Founders Fund, Merit Tech, and of course, the newly founded 20 VC Fund, disclaimer attached. And prior to founding Newfront, Spike was one of the first employees at Open Door, where he helped grow the team from five people to an enterprise value of over five billion dollars today. Prior to Open Door, Spike was an investor at Blackstone,
0:44 Harry Stebbings? where he served on the startup team that built Invitation Homes into the largest owner of single-family real estate in the United States. I do also have to say a huge thank you to Kevin Hart and Max at Merit Tech for some fantastic questions, suggestions today. It really did make such a difference. But before we move into the show today, I want to take a moment to mention HelloSign, a great example of a company that found success in building a product focused on user experience. HelloSign is an effortless e-signature solution used by millions to securely send and request legally valid digital signatures and agreements. They raised a total of sixteen million dollars in funding and recently got acquired by Dropbox for an impressive two hundred and thirty million dollars. Check out hellosign.com/20vc to join the thousands of companies and founders who value fast, secure, and simple e-signatures.
1:29 Harry Stebbings? And if HelloSign helps you sign that term sheet, you need to get the term sheet in the first place. And I want to give a mention to Draper Esprit, a publicly listed VC fund that invests in high-growth European tech companies with global ambitions. Their portfolio includes companies like Revolut, UiPath, Kazoo, Graphcore, and many other top European companies. Draper Esprit writes checks of USD five to fifty million dollars, focusing on sectors like consumer, fintech, health tech, deep tech, enterprise, and SaaS. And their investment team has an incredible depth of experience, both as operators and investors, that helps businesses scale globally. If that sounds like the sort of investor you want to work with, get in touch with them at draperesprit.com. That's D R A P E. R E S P R I T dot com.
2:13 Harry Stebbings? And last but by no means least, getting SOC two compliance, my word, it can be a nightmare. Well, not anymore, not with SecureFrame. SecureFrame provide end to end compliance that scales with you. So you can get SOC two compliance ready in weeks, not months. You can secure an audit through one of their preferred auditor networks. And then most importantly, you can stay compliant with their incredible automated reports and alerts. That's why SecurePass is trusted by the likes of Stream, Hasura, BannerPass and more. So check them out today at SecureFrame.com to turn months into weeks when it comes to SOC two compliance. But enough of me, so now I'm very excited to welcome Spike Lipkin, founder and CEO at Newfront Insurance.
2:56 Speaker 01 You have now arrived at your destination.
2:59 Harry Stebbings? Spike, it is such a joy to have you on the show today. I've heard so many good things from Max and the team at Founders Fund. So thank you so much for joining me today.
3:06 Speaker 02 Thanks for having me.
3:07 Harry Stebbings? I would love to kick off today 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?
3:18 Speaker 02 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 Open Door and worked on some of the initial insurance at Open Door. 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.
3:59 Speaker 02 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.
4:14 Harry Stebbings? Can I ask, I'm always fascinated by takeaways. We had Julia Dwal on who obviously was at Open Door with you. I'm really In terms of like the lessons that you learned from the time with Open Door, how did that experience impact your operating mindset and how you run Newfront today?
4:27 Speaker 02 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 Open Door, 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 Open Door was kind of ruthlessly focused on solving the most important problems at the time, knowing that if they unblocked one problem,
5:10 Speaker 02 they'd have more resources and talent to solve the next problem.
5:13 Harry Stebbings? 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?
5:23 Speaker 02 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.
5:55 Harry Stebbings? I like that in terms of kind of owning from zero to one and then delegating 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 and I was like, gosh, this is a terrible question, but I want to ask it anyway. How would you describe your style of leadership?
6:12 Speaker 02 Well, 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. 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.
6:43 Harry Stebbings? Can I ask, what do you do specifically to create that environment? It can be little things like, you know, Tom and the team at Gusto take their shoes off and they kind of have Gusto socks. And although trivial, it actually kind of creates a warming, homely atmosphere. I guess what specifically do you think you can do to bring out the best, but also create that environment of safety?
6:59 Speaker 02 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.
7:39 Harry Stebbings? 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?
7:47 Speaker 02 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 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 Moschare and Joe Greenstein. We have an advisor named Ling Hua 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.
8:27 Harry Stebbings? 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?
8:35 Speaker 02 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.
9:17 Harry Stebbings? 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? And how do you think about that?
9:33 Speaker 02 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.
10:01 Harry Stebbings? 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?
10:12 Speaker 02 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... 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.
10:57 Speaker 02 And it felt like bringing in someone who had done it before would allow us to accelerate the business.
11:02 Harry Stebbings? Can I ask, in terms of operations becoming that crucial part, it's often when you kind of scale from phase to phase, where you have that kind of operating debt which then needs to be fixed. The question that I have is like, what broke for you and when in the early days?
11:13 Speaker 02 A lot of things broke. I think we out scaled many of the systems we had in place. Early on, we made, I think, some of the right decisions, which were not obsessing about creating the perfect system, but really growing the business so that we could 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.
11:46 Harry Stebbings? Totally agree, in terms of kind of bringing Mike in and what he's done for the organization. Can I ask, in terms of like your management, 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 sell a family office, 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 that?
12:04 Speaker 02 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, but certainly one that's been difficult for me.
12:39 Harry Stebbings? Absolutely. I think it's incredibly difficult. It's one that I've never managed for sure. So I wish you well there. In terms of like the strengths, as I said, I heard about the motivational element. Specifically, I was told about the recent offsite and how you are able to get people, and this is what one of your team members said, to run through fricking walls. So in that very blunt term, how do you motivate and energize others so well, do you think? And what have you found really?
13:00 Speaker 02 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.
13:20 Harry Stebbings? I love that in terms of getting out of the way. I have a question for you on the unwavering vision and mission, and it's a little bit controversial. So I think vision is actually quite dangerous, because I always think you always underestimate what you can do in that five to 10-year period. And so if I said she, within X amount of time, you will have achieved this, you've actually so much overshot that the vision almost undersells yourself. Would you agree with me? And how do you think about the benefits versus the cons of mission?
13:44 Speaker 02 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
14:28 Speaker 02 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.
14:38 Harry Stebbings? Can I ask, you mentioned the decision-making there. In terms of decision-making, risk is always an inherent part of it. How do you think about your own relationship to risk, really?
14:47 Speaker 02 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 of 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.
15:21 Harry Stebbings? I totally agree with you on Odehver and on CEO Edition. So totally with you there. In terms of like fueling the growth, fundraising is obviously so central to our ecosystem and this podcast being called the 20 Minute VC. I do want to touch on this. How did you approach investor selection? I'm sure you had well over subscribed rounds. What was it that made you choose the people that you did?
15:37 Speaker 02 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.
16:11 Harry Stebbings? It's a really hard one, isn't it? Because you know, you hear the invest in lines, not dots. And you hear that always be raising and you do have to build relationships and trust over time. But then I also agree, if you build a really great business, you will attract great capital. So I think it's a difficult one. My question for you is like investor value extraction, I think is something that company founders don't do very well. How do you think about extracting the most value from your investors? And have there been any lessons on what's worked?
16:32 Speaker 02 We've optimized for finding investors that can help us de-risk core parts of our business. So as we were scaling Newfront, we wanted to learn from one of the best operators out there. And so we were lucky enough to work with Kevin Hartz 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.
16:58 Harry Stebbings? I will say to investors, it's like say the one thing where you can move the needle and only do that, but kind of have your position on the field, so to speak. So totally agree with you there. In terms of like the roster of investors, why did you decide to not actively announce the rounds? Obviously, there's a lot of chest pumping, but it does help with hiring. How do you think about announcing rounds and what was the takeaways from that?
17:16 Speaker 02 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 stay under 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.
17:44 Harry Stebbings? Yeah, I do definitely agree when it comes to competition. How do you feel about like its impact on hiring?
17:48 Speaker 02 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.
18:06 Harry Stebbings? Yeah, no, I definitely agree in terms of leveraging them for talent extraction. Do 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 be. If you were advising me, what can I do to be the best board member to you, the founder?
18:19 Speaker 02 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.
18:59 Harry Stebbings? Speaking of Kevin being amazing at something, it's funny, when I asked Kevin about what I should ask him before the show, he said, well, listen, I mean, Spike is one of the best in the business when it comes to negotiation. So his question to you was, what's the secret to successful negotiation and how do you approach it?
19:12 Speaker 02 That's 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.
19:25 Harry Stebbings? I do want to move into the quickfire on it with you now, Spike. So I say a short statement and you hit me with your immediate thoughts. Does that sound okay?
19:31 Speaker 02 Great.
19:31 Harry Stebbings? Okay, so I promised I'd read more during COVID, which is obviously failing terribly. What's your favorite book and why should we be reading it?
19:37 Speaker 02 Team of Rivals by Doris Kearns Goodwin. It's incredibly inspiring how a group of people who didn't see eye to eye worked so well together.
19:44 Harry Stebbings? What would you most like to change about the Silicon Valley tech scene?
19:46 Speaker 02 I think more opportunity for folks from different backgrounds.
19:49 Harry Stebbings? Totally agree with you there. Tell me, Max from Maritex question. What's your real name and then why is Spike?
19:54 Speaker 02 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.
20:01 Harry Stebbings? Love it. Must thank Max for that question. Which angel has done the most to help the company and how have they helped? I'm really passionate about shining a spotlight on amazing angels who may be a little bit more behind the scenes in funds. What angel's done the most to help the company?
20:12 Speaker 02 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.
20:36 Harry Stebbings? Yeah, Michael's amazing and I love that in terms of the Sharks. Tell me, penultimate one, why will the biggest startups of the next 10 years not look anything like those of the last 10 years?
20:44 Speaker 02 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.
21:00 Harry Stebbings? Does that not inherently mean compressed margins?
21:03 Speaker 02 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 experienced, 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.
21:22 Harry Stebbings? Totally with you there. It's a super interesting one. I really like that transition that you state. Tell me, next five years for you and for Newfront, paint that picture. Where are we going to go?
21:29 Speaker 02 Helping hundreds of thousands of businesses manage risks so that they can focus on what they do best.
21:34 Harry Stebbings? Spike, as I said, I heard so many good things from all the investors that we spoke to. So thank you so much for joining me, Stan. I'm so glad that we could finally do this one.
21:40 Speaker 02 Thanks, Harry. Really enjoyed it.
21:43 Harry Stebbings? So loved having Spike on the show there and could not be more excited for the times ahead with new front. If you'd like to see more from us behind the scenes, you can on Instagram at Hstabbings1996 with two Bs. However, before we leave you today, I wanted to take a moment to mention HelloSign, a great example of a company that found success in building a product focused on user experience. HelloSign is an effortless e-signature solution used by millions to securely send and request legally valid digital signatures and agreements. They raised a total of $16 million in funding and recently got acquired by Dropbox for an impressive $230 million. Check out HelloSign.com/20vc to join the thousands of companies and founders who value fast, secure and simple e-signatures. And if HelloSign helps you
22:25 Harry Stebbings? sign that term sheet, you need to get the term sheet in the first place. And I want to give a mention to Draper Esprit, a publicly listed VC fund that invests in high-growth European tech companies with global ambitions. Their portfolio includes companies like Revolut, UiPath, Kazoo, Graphcore and many other top European companies. Draper Esprit writes checks of USD $5 to $50 million, focusing on sectors like consumer, fintech, health tech, deep tech, enterprise and SaaS. And their investment team has an incredible depth of experience, both as operators and investors, that helps businesses scale globally. If that sounds like the sort of investor you want to work with, get in touch with them at draperesprit.com. That's D-R-A-P-E-R-E-S-P-R-I-T.com. And last but by no means least,
23:10 Harry Stebbings? getting SOC 2 compliance, my word, it can be a nightmare. Well, not anymore. Not with SecureFrame. SecureFrame provide end-to-end compliance that scales with you, so you can get SOC 2 compliance ready in weeks, not months. You can secure an audit through one of their preferred auditor networks, and then most importantly, you can stay compliant with their incredible automated reports and alerts. That's why SecurePass is trusted by the likes of Stream, Hasura, BannerPass and more. So check them out today at SecureFrame.com to turn months into weeks when it comes to SOC 2 compliance. As always, I so appreciate all your support. And wow, what an incredible set of episodes we have next week. I cannot wait to bring them to you.
Previous 20VC: CRV's George Zachary on His Relationship To Money and How it has Changed Over Time, Why The Best Founders Have Often Experienced Parental or Home Instability and The Stories Behind Investing in Unicorns; PillPack, Yammer and Udacity Next 20VC: Cyan Banister on Her Relationship To Money, Risk, Her Investment Decision-Making Process, Why We Will See A Reckoning in the Early Stage Market, Her Biggest Takeaways from HQ Trivia & The Future of Silicon Valley Page updated September 29, 2026 · transcript and summary are machine-generated