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Gopi Rangan ☂️ Here to answer your biggest Venture Capital questions (#8).

Episode 8 🍍90×9.co

Gopi Rangan is a Silicon Valley based venture capital investor.

Gopi Rangan is the founder and General Partner at Sure Ventures, an early stage venture capital firm investing in insurtech startups. The mission of the firm is to enable peace of mind for individuals and businesses. Portfolio: Blitzz, Decent, Hi Marley, Mile Auto, Rocket Dollar and SpotAngels. 

He is also an Adjunct Professor of Entrepreneurship at INSEAD. Gopi has an M.B.A. from INSEAD, an M.S. in Electrical Engineering from Arizona State University, and a B.E. degree in Electronics and Communication Engineering from Coimbatore Institute of Technology in India. 

www.sure.ventures 




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Gopi Rangan Founder & General Partner Sure Ventures

Gopi Rangan ☂️ Here to answer your biggest Venture Capital questions (#8).

Gopi Rangan is a Silicon Valley based venture capital investor.

Gopi Rangan is the founder and General Partner at Sure Ventures, an early stage venture capital firm investing in insurtech startups. The mission of the firm is to enable peace of mind for individuals and businesses. Portfolio: Blitzz, Decent, Hi Marley, Mile Auto, Rocket Dollar and SpotAngels. 

He is also an Adjunct Professor of Entrepreneurship at INSEAD. Gopi has an M.B.A. from INSEAD, an M.S. in Electrical Engineering from Arizona State University, and a B.E. degree in Electronics and Communication Engineering from Coimbatore Institute of Technology in India. 

www.sure.ventures 




Listen to this podcast on your favorite platform:

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OvercastPocket CastsRadioPublic



Full transcript

Introduction

Welcome to the 90×9 podcast, here we talk about the who, how & why behind explosive startup growth. I’m your host, Adi, previously I was the Fast Growth Executive at the million dollar pineapple, the main sponsor of this show. Now, thanks to you lovely people for bringing explosive growth to this podcast, I’m officially the Head of Growth & Operations at 90×9. Really? Yes, last week we passed more than 2000 plays in Paris alone. Exciting times people, we are officially playing on 9 platforms in more than 10 countries! So thank you for tuning in and sharing with your friends. 

A quick note about our main sponsor: if your startup is ready for explosive growth, then you want to checkout The Million Dollar Pineapple, the only Consulting Firm to specialize in growing startups to $1MM in revenue within 2 years guaranteed, GUARANTEED. If your startup is ready for this type of growth then go to 1in2.co, I will include this link in the show notes & now for today’s episode. 

Adi 🍍

Hello lovely listeners! Today we have a very special guest on the show. Gopi is one of the most brilliant advisors that I currently, and very frequently rely on for guidance when it comes to epic feats in need of a highly strategic mind. After episode 7, I received quite a few questions around Venture Capital and immediately thought of him. So here to answer all of your VC questions is my favorite Silicon Valley based Venture Capitalist, Gopi, the founder of Sure Ventures.

Gopi Rangan ☂️

Hi Adi, thank you for inviting me to the show. I am delighted to share my experiences and insights. Hello everyone, I am the founder of Sure Ventures.

Adi 🍍

When did you start Sure Ventures and why?

Gopi Rangan ☂️

I launched the fund early 2018.  The reason I started the fund was that I felt there was a clear need in the world of the start-up ecosystem, especially in the InsureTech sector, who were struggling to find investors to work with. So that became a huge opportunity. More importantly, I wanted to work on a business that had a strong mission that lasted many years. I came up with the mission of enabling peace of mind for all individuals and businesses. I wanted to invest in startups that focus on that type of mission. That is the genesis story from building Sure Ventures from the early days.

Adi 🍍

What did you do before starting Sure Ventures that equipped and prepared you for this? What is your origin story? You are a superhero in this field.

Gopi Rangan ☂️

I am not really a superhero. I am just an investor and I love working with entrepreneurs, especially in the early stages. The early stages of a business is a roller coaster ride. A small contribution that I make can have a huge impact on their business and that is very fulfilling to me. I had this type of experience of many years being active in the Venture Capital world. That’s what inspired me to start my own fund. Prior to starting the fund, I helped start an Angel investment group and that was very helpful for me. It gave me a window into the world of the startup ecosystem and how entrepreneurs think, especially at the founding stages and the very early stages. Prior to starting the Angel Investment Group, INSEAD Angels, for the alumni community for Angel Investors that graduated from business school INSEAD and living in the Silicon Valley. That was a fantastic, strong group that came together and we made a bunch of investments as a group. 

Prior to that, I was with two different organizations. I was on the investment team at USAA’s Corporate Venture Group. I was a Managing Director. There I was exposed to the world of financial services, banking, insurance, and invest-management, and many other things. I saw that especially in the world of insurance, technology barely had an impact. Having seen technology have an impact on the telecom world or media and other sectors, I noticed that various aspects of insurance could benefit from the use of technology in a substantial way. Over the next 10-20 years there will be a lot of opportunities for technology to improve the way insurance works and create new products and services in that sector. That was a fascinating experience for me at USA.

Prior to that I was at a company called Altera, which is now part of Intel. Intel acquired the company. I help manage investments for Altera on the strategic investment side. That was my foray into the world of Venture Capital. I learned a lot from some amazing entrepreneurs that I work with. Between the two organizations, at Altera and later at USA, I worked with some entrepreneurs that are easily some of the best in the world. There was one IPO that came out of the portfolio and there were a bunch of acquisitions and most of the other startups would always follow on funding. I had the distinct pleasure of working with entrepreneurs that were successful in the ecosystem. That prepared me for this journey that I am starting now with Sure Ventures. 

Adi 🍍

Some people may decide one morning to become a Venture Capitalist, get some money, and see what they can do, and no one takes them seriously. When we hear a story like yours, you have really been in the trenches and through the wars. You cut your teeth with the greatest wolf packs out there and come up within the startup space and really know what you are doing. 

What questions did you ask yourself when looking at starting Sure Ventures? We now know you have an extensive background, a lot of knowledge, and have worked with a lot of heavy hitters. What are some things based on your experience, that you need to look at in terms of qualifiers before you make a move?

Gopi Rangan ☂️

With Sure Ventures, I am an entrepreneur myself so I have more empathy for entrepreneurs than I did in my early years of my career. There are two things I ask myself. 

  1. Do I have the commitment to stay with this for many years? Building a venture fund is actually very difficult and the story of a venture fund doesn’t play out until the third or fourth fund. So it takes many years for each of these funds to be operational, make an impact, and portfolio companies are built, and eventually to generate exits. To see that whole story play out, it takes many years. I want to know that I have a purpose and a mission that I can marry and stay with me for those years.
  2. Do you have the guts to cut the cord and walk away from other equally attractive opportunities? And instead start this new business that shows promise, but it might be a very adventurous ride with ups and downs, high highs and low lows. Do you have the guts to jump into something like this? That’s what most people talk about. That is also important to have the bravado to go out and start a business, especially something like a Venture Fund is a hard thing to do.  

Those two questions are on my mind. The first question is more important to me. The bravado and everything I was very fortunate to see many entrepreneurs start businesses. I understood that it takes that type of courage to go out and start a business. Courage alone is not sufficient especially with a Venture Fund. It takes the ability to stay through. What convinced me that I had the right idea and right type of opportunity to stay through is the space I found. The space is just like how FinnTech revolutionized banking. 

In a similar way, InsureTech is likely to revolutionize the world of insurance. If you look at the world of insurance, it touches people’s lives in a meaningful way almost everyday. Every business and every person has the access to it. People who do have access to financial services in the world of insurance, benefit from it. People who don’t will hopefully have that in the future. If you look at that whole sector, it’s a massive sector. It’s 5 trillion dollars of premium collected by all the insurance companies put together worldwide. That becomes the backbone of the world economy. This large powerhouse within the economic world has had very little innovation. Something that touches people’s lives in a meaningful way hasn’t really evolved. The products, services, and the internal infrastructure hasn’t really changed a lot over decades. I used to joke that for decades the auto insurance products and home insurance products, the way we deal with insurance has remained the same for decades. I was a little shy to say that insurance companies haven’t innovated in decades. But then the CEO of Aviva came out and said insurance is stuck in the stone age. That made it easier for me to claim my own words and say there’s a lot of room for innovation out here. That becomes a ripe ground for startups to go out and build innovative solutions because the incumbents aren’t. That became a really strong reason for me to stick with something to work on for many years. 

Adi 🍍

I am dying to know your thoughts on the new app that’s supposed to be disrupting the insurance space, Lemonade. What do you think? 

Gopi Rangan ☂️

There are many companies like Lemonade. It’s a story we hear quite often. It’s an example of how new ways of designing products, especially reaching customers through mobile platforms and web platforms can change engagement in insurance. Distribution is one of the most popular addressed issues in insurance, that is why we get to see companies like Lemonade and others focus on this problem. But there’s more to insurance than just distribution. Don’t get me wrong – distribution is an important and complicated problem. I don’t think we have fully solved it and there are many more solutions like Lemonade that we would get to see in the future. But I also see a lot more opportunities in other aspects of insurance, like underwriting insurance, how you do that, fraud, how do you build a better policy administrative platform, and how do you build core systems and infrastructure that’s part of the digital world. Can you use technology like Blockchain or Machine Learning with advanced capabilities to significantly improve the world of insurance? Lemonade is scratching the surface of that and one of the few examples that we see today. I expect to see hundreds of startups that will begin to solve some of the problems that we see today. 

Adi 🍍

What were a few surprising lessons that you learned when you first launched Sure Ventures?

Gopi Rangan ☂️

I’m still learning. I’m an entrepreneur so I have many good days and there are also days where I curl up and ask myself, “What did I sign up to do?” But that’s part of the journey and there are many lessons that I reflect on. Pace of learning is quite accelerated when being an entrepreneur and I am experiencing that now. There are many lessons that I learned. One of the lessons I learned more recently is the timeline for entrepreneurs and how they think about building a solution, especially in the world of insurance. It is not the same timeline as other companies in other sectors. For example, the kind of complicated regulations that happen in the world of insurance. That sometimes scares both other entrepreneurs and other investors. There has to be some level of maturity in understanding the regulations before an insurance startup can launch a business. 

At the same time, there are also some entrepreneurs and even some other VCs think they can build anything and disrupt a sector and take down a whole chunk of industry quite easily. That’s not easy. It takes time to establish an insurance business and be respectful of some of the regulatory guidelines. Not every regulatory guideline is perfect and some of them need to go but the assumption that some entrepreneurs make is we can disrupt some sectors if four people in my garage write software and can take down a chunk of the industry. That is not going to happen easily. Most opportunities require existing incumbents to come together, sit at the table, and work with the innovative startups. That building a bridge between the startups and the existing incumbents, a successful relationship between the two will make it possible for startups to grow much faster, and also for these large companies to get access to innovation. That was one of the lessons I learned just as I was starting Sure Ventures. I knew this was important but I now realize how important it is. It is important to bring different players into the room to make it work. 

Adi 🍍

I can’t tell you how many times I had meetings with first-time founders where they say “we are going to be the first movers and disrupt an industry” and they are talking as if the incumbents won’t fight back. Their war chest for a month is more than your 5 year marketing budget. There’s no way you can outscale them. You’re going to have to find someone to partner with and an ally that’s going to help you to grow because there is no way you are going to compete with $10 million companies. It’s just not going to happen. 

Gopi Rangan ☂️

That’s true. If you look at some of the most successful insurance companies, like the top 20 insurance companies, they have a very healthy business and they have been going on for years, some of them for decades or even more than a century. They have learned to evolve over different types of business cycles over the years with generational stability. Kudos to them for being able to build a business like that. What I tell large corporations when I meet them is what got you here will not get you to the future. The world is different today. But at the same time, the flipside is for startups to learn from these successful businesses that have lasted for decades. It’s good to know the foundations of those businesses are very strong and that’s something startups can learn. 

Adi 🍍

What made you decide to launch Sure Ventures instead of joining another firm? 

Gopi Rangan ☂️

Just like everybody else I also had insurance problems. Very early in my life I had an incident that opened my eyes to how insurance has an impact on people’s lives. I got into a car accident when I was 23 years old. I was a new immigrant in the country. I got my first job in the Silicon Valley. I was at the top of my world but all that came crashing down when I got into a car accident. My car was totaled and thankfully nothing happened to me. I went to the movies that day and everything was fine. But the impression that stayed with me was the presence of an insurance solution that put me back on my feet and I went to work the following day. That really opened my eyes. Since then it’s like photography. Once you are a photographer, you see everything through a lens of a camera. I started looking at the world through that lens and asking why is that person taking a risk? Because there’s a safety net that protects them. Why is this business able to take a risk? Because there’s a safety net that protects them. 

Later when I was in business school and I visited Bangladesh and I saw how Nobel Laureate Mohammad Yunus had created an impact in Bangladesh – person after person, family after family, village after village. What he had done was create safety nets for people so that when bad things happen – it could be as simple a bicycle getting stolen that has an impact on a family or it could be a natural disaster, a famine or a flood that wipes an entire village out and how do you get those people back on their feet. That’s when I saw that access to financial products that create a safety net will have a massive impact on people’s lives. So when I started thinking about Sure Ventures, I asked what do I want to do with the next 20-30 years of my life. This became the crux of that thesis. That was the genesis of Sure Ventures and what I thought about when I started it. 

Adi 🍍

Powerful origin story here. Knowing what you know now, what will change with Sure Ventures 2.0?

Gopi Rangan ☂️

I am still in the early stages of 1.0! I don’t want to get too far ahead of myself. I think it’s a very good question. These kinds of questions are very relevant for Venture Capital investors. Every entrepreneur should ask this question: What is the future of this firm? That’s important. The VC should be able to answer these kinds of questions because they should always have a vision for their next fund and subsequent fund. 

My vision for Sure Ventures, it will start as a small fund and I expect that bridge we talked about between startups and large corporations. I want to build that bridge so well that both corporations can access innovation in the startup ecosystem, and startups can also benefit from learning to work with large corporations. 

Let’s unpack that. What I expect to do even better with Sure Ventures 2.0 is to help startups navigate the confusing, complicated, bureaucratic landscape within a large corporation, where if ideas not invented here it goes to die, or there are enough antibodies that kill new ideas in a large corporation. How do you navigate that as a startup? You find champions within these corporations that understand what you do and appreciate what you bring. They will fight for you and at the same time they also find a strategic goal that aligns with them so it would be a meaningful commercial partnership. I want to be able to facilitate that from the startup side. From the other side, a corporation’s perspective, it is very difficult to work with a startup that barely has an idea or a prototype that’s not very stable or robust and even if they have a revenue, it’s not a stable revenue that is steadily growing. What do you do with a company like this? How do you wrap your head around a business that is young and growing, but has great potential? How can you find opportunities that can tap into the innovation outside the four walls of the corporation so that you can get access to innovation in the startup ecosystem? There is so much noise in the startup ecosystem. How do you find the few that are a perfect fit for the business to build a commercial partnership? It is not possible to build a commercial partnership with many of them so you have to be picky with who you choose as a partner. That’s a problem that’s quite difficult for large corporations to solve. 

I want to be able to help both sides, the corporation and startup, by building a bridge between them. I want to be able to do that better with Sure Ventures 2.0. Sure Ventures 1.0 is a start, but 2.0 will be even better. 

Adi 🍍

I think a lot of people find value in that. For me personally, I have only ever been in the startup space and sometimes when I am trying to communicate and work with people who are coming from the corporate world into the startup space, it’s like we are speaking two completely different languages. We have to find someone who has had a foot in both to translate because if there isn’t a translator, yes, we are both speaking English, but two completely different versions of English. If there isn’t a translator, the pieces all end up falling on the floor, simply because we don’t realize we are saying the same thing just using different terminology and metaphors, and coming at it with different worldviews. I am definitely excited for 2.0. No pressure. 

Do you prefer to lead or co-invest with other VCs?

Gopi Rangan ☂️

That’s a very popular question asked of many VCs. There are some VCs that only follow and wait for a lead and there are investors who have a very strong preference to lead. But let me answer the question in a slightly different way. The way I want to position Sure Ventures is when I make an investment in a startup, that should be a very strong, positive signal for the world. It should be positive signal of confidence for customers, for potential future employees to join the company, for other VCs in the future who will invest in the company, so that’s the way I position myself. There will be situations where I will lead investments and that would be the appropriate thing to do, and there will be situations where I will co-invest with the appropriate lead who prepares the investment funding for the startup. 

I am not going to force the situation that I will only lead or I will only co-invest, although I prefer to lead. The important role I want to play is I want to be among the first people that the entrepreneur calls to get help. Either to call and celebrate “we had a victory today, we won a customer contract” or “I am having trouble and I need someone to talk to or a shoulder to lean on and brainstorm problems.” I want to be the first phone call that I get from these entrepreneurs. That’s a spot that should be earned and it’s not easy. It’s an enormous amount of trust and it’s an honor to get those phone calls, the first phone call from entrepreneurs when they are feeling jubilant or when they are feeling down. That’s what I am going to work towards. The question of leading or co-investing is important from a practical point of view, but my aim is to be an important investor and earn that spot so I get the first phone call from the entrepreneur to help them.  

Adi 🍍

That’s very cool. I think that’s one of the reasons you are one of my top mentors.

Gopi Rangan ☂️

I like being a coach. I admire entrepreneurs who are the players. They deserve to win all the accolades, but I really enjoy playing the role of a coach where my small contribution makes a huge impact on them. Most of the time they don’t need any help, but occasionally they might need a little bit of support, a nudge here or there, and that’s what I am here to offer.

Adi 🍍

That’s kind of cool how you can be working on a crazy, big project with really huge risks, high reward. There’s a human element of “Hey I’m about to jump off this cliff. Hold my hand for a second,’ and getting to be there with the founders when they are making huge jumps having that front seat and being that support is one of the coolest things about working in a startup space. 

Gopi Rangan ☂️

That’s what makes my job the best job in the world. Front row seats to this adventure. It’s amazing. 

Adi 🍍

I always say I don’t want to be the smartest person in the room. I want to be the secret weapon or the right hand of the smartest person in the room. But it’s a very fun spot, very exciting spot to be. How is your firm different from the thousands of others around the planet? 

Gopi Rangan ☂️

I play a specific role in this market. I invest in pre-seed and seed stage startups in the Silicon Valley. I’m located in the Silicon Valley, but I make investments nationwide in the U.S. There are not many firms like this. There are a few large VC firms that focus on the InsureTech sector, but they don’t primarily focus on just insurance. They are pretty generic and they also want to dabble in the world of insurance. I welcome that, it is great. I am glad there are players like that. There are FinnTech focused funds and even some InsureTech focused funds but they are much larger. They invest only in series A stage or later stages and that leaves a gap in the market for investors like me. I hope to see a few more like Sure Ventures focusing on seed stage in the InsureTech sector. There are a few small funds, micro VC funds that focus on many different types of topics. But when they make investments at seed stage, they look at also insurance and not just insurance. It’s good they have exposure to the world of InsureTech, but none of them really focus primarily on insurance. There’s a lot of synergies and cross-pollination that can happen when multiple portfolio companies are facing similar problems, solving for the same type of efficiencies that they want to bring, but in different ways. There are possibilities for collaboration and that is something that I would be able to do that most other VC firms wouldn’t be able to do. 

Adi 🍍

What criteria do you look for in startups before you make an investment?

Gopi Rangan ☂️

I’m glad you asked that question and not the question predict the future and tell me what’s going to happen because I have literally no idea how the future is going to go. I don’t have a crystal ball; I’m not a psychic. I have no way to predict what is the next best thing. If I was a psychic, I would be an entrepreneur. Entrepreneurs are the ones that create the future and they have a much better view on where the world should be. Often they are frustrated because they see that world in the future and they are working hard to make that future happen, but they are stuck in the present and they are dealing with current situations and problems. Leave it to the entrepreneurs to predict the future. My work here is to find ambitious, mission-driven, motivated entrepreneurs, who are working towards a problem that will improve the way we live and they are committed for the long-term. My aim is to find such entrepreneurs and once I find them, I want to be able to add value to their mission. If I can be a part of their journey, it will be an honor to participate. I would fight my way to get a spot in the front row seat, watch the adventure happen, and hopefully contribute to that journey. That’s the approach that I take. 

When I look for entrepreneurs, there are a few things I look for. I can give you an example. In the past, one of my portfolio companies called Roost – Roel Peeters is the Founder and CEO – he didn’t come from the world of insurance but he is one of the most prolific entrepreneurs that built a business and has had an impact on many insurance companies. I like entrepreneurs who are not necessarily from the world of insurance or any domain. Entrepreneurs coming from the outside tend to have a fresh perspective, a new way of looking at things. The lack of detailed knowledge is actually good because they are not jaded. So when they see new ideas, they walk in with a spark in their eyes, and they just go out and try things. That’s not something that can be done by experts. Experts have brilliant ways to kill a new idea and they know a thousand ways they would fail. But entrepreneurs who are fresh in their thinking, and can come up with a lot of creativity. That is something I look for. 

It doesn’t mean that people who have a little bit of expertise cannot come up with a new idea, especially in the world of insurance. It is very helpful to have someone that has knowledge in the sector, but I would tell entrepreneurs, if you are looking to solve a problem, go to a sector where you won’t be held back by your past experiences. Then you will be able to find something you can do differently. Such entrepreneurs have a much greater impact in the world. That’s one thing I look for. 

Different people ask different questions. Like, iIf it was your own personal money, would you make an investment? They have their own emotional filter that they use. I ask the question – is this an entrepreneur that I could work for. If I was VP of business development working for this this founding team, how would I feel about it? I need to get a very strong feeling about it and of course backed by a lot of data to show there’s an opportunity in the market. If the opportunity is huge and the problem being solved is real, it’s not just a hobby. There’s clearly a business plan flushed out. All of those things come together. 

The cherry on top of the cake is personal feeling that if I did work for this founding team, how would I feel? When I cross over that bridge, it gives me the confidence that all right, I can back this team and stay forever, committed to building this business. Those are the two main things that I look for. 

Adi 🍍

Why do you focus on the InsureTech sector?  

Gopi Rangan ☂️

We talked about a few reasons. My own personal reason and where I see the business opportunity here, there’s lots of room for innovation. But let’s go to the next level of detail here. If you look at the FinnTech sector, depending on which report you read, there’s about $150 billion of venture capital funding that has gone into the FinnTech sector. The FinTech sector targets the banking industry. The FinTech sector has produced a significant amount of innovation that has transformed the world of banking. Examples like Robin Hood on wealth management, many Robo Advisors, Peer-to-Peer lending companies like Prosper lending club and those types of companies, and a host of other companies which has led to more than 25 unicorns in the FinTech sector. 

As a Venture Capital investor, I am looking for a pond where I can fish that would be rich with opportunities like this in the future. Where is that opportunity? When I look purely from a business perspective, I see the opportunity in InsureTech and I see there’s about $10 billion funding over the past 4-5 years. I expect that in the next 10-20 years, that number is going to multiply a lot. The number of startups today in InsureTech is about 300. There will be many more in the InsureTech sector. I can only imagine the number of unicorns to come out of this space. This is a space that is very ripe for innovation and there will be lots of opportunities for startups to build billion dollar businesses and even bigger than that. That makes it very attractive as a venture capital investor. At a personal level, this topic of providing access to insurance products creates a safety net. Once we figure out a better way to manage, measure, and distribute risk, it creates an even better world for all of us. 

There are new types of insurance products that will be created, like cyber insurance, that’s a whole new set of liabilities that we haven’t encountered before we will. It’s only growing to grow, different types of new liabilities that we will be exposed to. We will need new insurance products for that. There are some legacy insurance businesses, like auto insurance and others, where there needs to be a new way to build a business model. These legacy insurance products and services are stuck in the way auto insurance was sold 40 years ago and the business model is the same. Can we use technology to make a difference in how we build these insurance products? Can these products be born in the digital world? That makes an impact on people’s lives and there are lots of opportunities there. Especially in the world of insurance, engagement with customers is very poor. Insurance sector lags behind many other sectors. Even banking is better. I asked an executive management team of an insurance company why are you in the Silicon Valley? They said we want to be like the banks, innovative. I rolled my eyes. I can’t believe they are using banks as a benchmark for innovation! 

There is clearly a lack of trust and there’s an opportunity to build trust using digital platforms. How do you build trust in a digital world with customers who don’t want to meet agents anymore? They sometimes make a phone call but even that is dwindling away. How do you engage with them on a mobile platform? Maybe through text messages, maybe through video, chatbots, or web platforms. How do you build trust through those platforms through engagement opportunities. The legacy way of only engaging with the customer twice – once when insurance companies negotiate premiums and sell a new policy and the other opportunity is when there is a claim. The claim experience, no matter how awesome it is, customers don’t want it to repeat. Besides these two opportunities, how do you engage with customers in a more meaningful way? Perhaps throughout the year and throughout their life so insurance companies and products are seen as a trusted solution that they rely on for their lives. How do you do that both for individuals and businesses? Commercial products have a very similar problem as well. That creates a whole new opportunity. 

At the end of all of this is so much data, and we are barely scratching the surface on the amount of data that will be available. In the future when IOT devices and many other technology-based sensors will produce data, how do you use that data to generate meaningful insights that will help us measure, manage, underwrite, and distribute risk? That’s the most interesting thing and we are still a long way from capturing opportunities on the data side. Innovation of a business model, creating of new products, and engaging with customers are things that are relevant today.

Adi 🍍

You have a long list of reasons. I’m looking forward to you changing the sector. I am definitely part of that group that does not want to talk to an agent. 

Gopi Rangan ☂️

It happened in the travel world. There was a time when there were a lot of agents and agents helped you book tickets. Distributing insurance products was very effective through agents and how can you replicate that success? It’s not that all the insurance companies are laggards and they don’t have valuable knowledge. That’s not true at all. In fact, if we can find knowledge that resides with these agents, we can learn from them and enable the future of insurance through technology platforms that can replicate the success of these agents. The average age of these agents is 59. They aren’t training the next generation in distribution of insurance so their wealth of knowledge is disappearing and how can we can tap into that wealth of knowledge so that we can benefit in the future without having to reinvent how they did work. That’s something that many startups can learn.

Adi 🍍

I don’t know if you know Ladino or Yiddish but they are not very well documented languages so the only way to learn is for someone older to invest the time and energy. Both of the languages are kind of dying outside of certain areas because so few old people are having that time to sit down with the young ones and teach them. 

Gopi Rangan ☂️

That’s happening in the world of insurance, especially with the agents.

Adi 🍍

I believe it. If languages that were core to the Jewish culture are dying, imagine insurance know-how.  

Gopi Rangan ☂️

The other aspect of it is the underwriting is done manually and there is a lot of subjective thinking. There’s a lot of know-how and intuition that is used, in addition to data. But can we make it more optimized and more data-driven. Now that we have access to data, we have better ways of gathering insights from data. How can I automate a lot of these things? I believe that is going to have a huge impact. Incumbents should be ready to embrace those things, whether they like it or not technology will have an impact on a big chunk of the insurance industry. 

Adi 🍍

How many startups are in your portfolio right now? 

Gopi Rangan ☂️

I have 6 startups in my current portfolio at Sure Ventures, and I am very excited about them. I got very lucky to find some amazing entrepreneurs to back. They are Mile Auto, it’s a pay per mile insurance business. Decent.com is a blockchain based health insurance platform. Rocket Dollar is an investment diversification platform, where people can invest their retirement funding into alternate assets. Hi Marley is an intelligent conversation platform for insurance companies. Blitzz is a video-based customer support platform that can be used for claims processing and underwriting. The sixth one is Spot Angels, a data analytics for parking. 

Adi 🍍

If someone wants to find out more about these startups, they can go to your website?

Gopi Rangan ☂️

Yes, my website www.Sure.Ventures and that has details about all these portfolio companies.

Adi 🍍

As much as I love to spend the rest of the podcast talking about each one of those, maybe we can have those people on the show. Does the general process of a startup look similar to the process of what ends up in your portfolio? 

Gopi Rangan ☂️

Each case is different. There is no one set way. The typical opportunity is that I get introduced to the entrepreneur through someone in my network. Most VCs operate this way. Getting introduced to me through someone I already know is a good way to start the relationship. In some cases, some of these relationships have been established for a long time that has lasted many years. But in other cases they are brand new relationships and I make an investment after a few meetings. The process varies; there isn’t one set way. But getting an introduction through someone I already know is very helpful. 

The second step of the process is that I like to learn. I am an ultra-geek on so many different topics. I am always interested in learning. My wife makes fun of me that I spend too much time on obscure things that may or may not have any consequence. For me, I get excited when I sit down and talk about something that the entrepreneur is very passionate about and they thought about it so much that I have never thought about it that way. After an hour of conversation, we are still talking about it and painting different scenarios. That is very fascinating to me. To be honest, that’s what makes my job very interesting and fun and that’s what I live for. If I can have that kind of conversation with an entrepreneur, then I get to learn and that’s very fulfilling for me. My process that comes very early in my engagement.

Adi 🍍

I didn’t realize this is an actual strength on the strength-finders test, but learner is one of them. It is a strength for you and it’s an addiction. It’s so much fun learning something new, but what I tend to forget is that’s not a strength for someone. If I say “Hey let’s go learn a new language,” it sounds quite stressful to anyone that doesn’t have that strength in their top 10.

Gopi Rangan ☂️

I learned conversational Sanskrit and I found out that only a few thousand people speak Sanskrit. Let me be clear, I am not an expert. I speak sub-beginner level, and there is no utility value for it. But I love it. I like learning things that are obscure. 

Adi 🍍

For a while I was addicted to Udemy because I was buying new courses thinking “I have to do this one and that one.” My husband reminded me that I have work and a family, and I might not have time for 800 hours of courses. Then I tried to pull my daughter in thinking “Would she want to learn this with me?” My husband, again the voice of reason said, “You are not teaching our three-year old Python.” Do you maintain an anti-portfolio?

Gopi Rangan ☂️

I do. Most good VCs have an anti-portfolio. I have my own regrets of startups that I wish I had invested but didn’t. Many of those things came from this pattern. I would meet an entrepreneur, hear the story, and I would dig deeper and get very excited. Then something starts to bother me because I don’t know too much about something new. Then I wonder if a little bit of knowledge can be dangerous. Then I would argue with myself and over a period of time, I have convinced myself that maybe this is not good anymore. While I started with a lot of optimism and positivity, it faded away. I feel too scared and I walk away from the opportunity. I try to catch myself and avoid falling into this trap, but I don’t think I can completely immunize myself from this. I am improving and learning everyday. I always ask myself a rational question, am I scared because of a past experience or is it a real red flag here. 

That helps me, but of course I have missed opportunities in the past. I went to business school at INSEAD. My classmate, Frederick Mazzella was the Founder of BlaBlaCar. I saw how hard it was, especially the first 6-7 years. It was a struggle for him to build that business. When I met him, it was called Commuto, and it morphed in different ways, and now he has become wildly successful. BlaBlaCar is doing well and they have raised millions of dollars from various VCs. Around the same time, I saw ride-sharing startups in the U.S. I was jaded because I felt like this was a tough one. I saw first hand how my friend was building the business and it really made me skeptical about it. I was so wrong. Ride-sharing market has exploded. There are so many opportunities out there. Even the leaders are way bigger than I thought they would ever be. As a VC, I feel embarrassed about it that I didn’t see this coming. In fact, I should have used my experiences from the past to get inspired and get behind it. Instead, I let my own bias hold me back. I hope that doesn’t happen too frequently in the future, but I am always learning.

Adi 🍍

That’s a really good approach to sit down and say, am I having this negative sentiment because there are red flags or because of a previous poor experience. I heard a really good quote from a CEO of a startup I am working with right now. He said when you have a gut feeling or intuition, it’s a culmination of all your past experiences condensed into a two-second reaction. When your gut is telling you something, if you break it down later when you have time to go through and write about the science behind why you are feeling this way. You will find it’s because of 300 different things that have happened over the past 4 decades. This one-second reaction is my brain quickly leaping through everything that has happened in the past. It’s kind of cool how the human brain can do that. What are some tools and tactics that you use to manage your time and team effectively as an entrepreneur yourself?

Gopi Rangan ☂️

I put everything on my calendar. I live by Google Calendar and that helps me stay organized. I have many symptoms of Dyslexia and I miss a lot of details. I rely on the calendar quite a bit and a to-do list.  Those two things help me streamline my days and help me stay on top of things. The key lesson here is that I have learned to say no to a lot of interesting things. For someone like me who likes to learn and dabble in different things, it’s a hard thing to do. 

I have learned to be a little more disciplined and be tough on things that are fun, but not very productive, like watching YouTube. I deleted some of the social networking apps from my phone so I don’t use Facebook. It’s very easy to get distracted by those things. As a VC I am in the business of helping people, and unleashing their maximum potential, but there is only so much time I have. I can only meet certain types of people who I can add value to. I have to say no to others and figure out where that boundary is. I have learned over the years to say no, and stick to a routine so that my calendar dictates and tells me what to do. 

Adi 🍍

I don’t know if you read the book Tools of Titans by Tim Ferris. One quote from there is when he is talking to a gentleman he says “If it’s not a ‘Hell Yes’, it’s a ‘No’.” Otherwise you end up looking back and realizing I have done a bunch of mediocre things and when some amazing opportunity came along I had to say no because you signed up for so many mediocre things. I reshaped my own schedule that way. It takes a while. Being addicted to learning, makes it really hard because there are all these cool, random things you can learn about. But you are moving in many directions and not really getting anywhere, and maybe feeling like you are on a hamster wheel. I can definitely resonate with that. It’s a struggle I have been trying to overcome.

Gopi Rangan ☂️

All of us get 24 hours. It’s a question of priority. We can prioritize the things that we care about and only say yes to the things that matter to us. It’s not easy to do it consistently, but that it something that will make a huge difference on how we live our lives. 

Adi 🍍

It gets harder, as you now know, when you have a family. You have a young family and a young Sure Ventures. How do you balance the demands of work with the responsibility of raising this adorable family?   

Gopi Rangan ☂️

Strangely, that actually helps me stay on top of things and be more organized. Family is #1, and comes above all else. My evenings and weekends have become more precious. Being in the venture business, it’s really hard to be away from events and things like that in the evenings. I have tried to limit them to one or two a week. I have become very picky about what kind of events I attend and where I spend my time. That has helped me streamline and constantly look at my priorities. At the end of all this, why I do what I do, is for family. So I can have a beautiful family life and I don’t want to sacrifice that. Having that part of my life fully developed – being a good father, a good husband, a good son, a good brother – brings a wholesomeness to who I am and that allows me to be a good VC and a good investor to my portfolio companies. I don’t think I would be as good without my family.  

Adi 🍍

That’s an interesting take on it. Your saying having all of that together makes you balanced. 

Gopi Rangan ☂️

This is something I admire about the millennial generation even though I am not a millennial. The importance of purpose in life and where you spend time is very clear to them. The previous generation of business leaders came from the philosophy that you kill yourself, sacrifice your family by not spending any time, and spending more hours at work is the best way to demonstrate that you are a committed employee and a good leader. That has changed. I am not inventing this, but the world has changed to a point where it rewards people who are fully developed, wholesome, and not just one dimensionally superior in one area, and weak in other areas. We are moving in that direction, and the credit goes to the millennial generation for pushing us in that direction. 

Adi 🍍

You’re one of the very few people I have heard say anything positive about the millennial generation.

Gopi Rangan ☂️

They are entitled, but it does come with a very strong spirit of self advocacy and that advocacy includes fighting for time for my family or an annual vacation with your buddies. They make sure that happens and that’s the rhythm that keeps them going. They will never compromise on that. It’s a good thing and it will lead us to a better place.  

Adi 🍍

As a millennial I can tell you, we graduated from college into a recession, after having spent our childhoods being told “If you go to college and get a degree, you will get a great job.” No one was getting hired. Not only did we graduate into a recession, we are up to our eyeballs in student loan debt. We also had the wrench thrown into healthcare, where the cost of our health insurance is up through the roof. And we were watching our parents lose everything they have spent their entire lives working on. All of this has pushed my friends and I to be more firmly planted into the belief that if I am going to have a job, it’s going to give me my life’s purpose. Instead of waking up at 60 thinking I spent my whole life working for a nest egg that was lost in a recession. The perfect storm that we graduated into created a unique personality for an entire generation. 

Gopi Rangan ☂️

Hopefully, many of the problems you highlighted will be solved by some of my portfolio companies.

Adi 🍍

I totally expect it. I am there with high expectations for the startups. Founders, if you’re listening, high expectations for all of you.   

Gopi Rangan ☂️

Challenge accepted. 

Adi 🍍

Game on! If you can tell an app developer outside of your portfolio companies to create the perfect new tool for Sure Ventures, what would it be?

Gopi Rangan ☂️

I would love to have a personal CRM that helps me manage everything that happens on a day-to-day basis. To keep track of all my relationships, contacts, bills, data, and all the administrative tasks that have to happen a certain time. Also, if we could automate taxes and so many other things. Everything is connected to everything else, but it’s all living in many different locations. If there was a CRM that put it all together, I would be the first customer.  

Adi 🍍

That actually would be amazing. That would be insane for a cybersecurity of that company because everyone would want to hack it on a regular basis, but I have never heard that answer before. I would be the second customer, if and when it’s created. 

Gopi Rangan ☂️

We hope that happens.

Adi 🍍

For those listening who know how to code, get on it. Let’s go. 

Final question: if an inspiring entrepreneur wishes to connect with you, can they and where can they connect with you?

Gopi Rangan ☂️

I am everywhere. I am an advisor at many accelerators. I love spending time with entrepreneurs and learning more about how they build their business. You have the work for the future. I am out there all the time. I teach as an adjunct professor at INSEAD. I teach an entrepreneurship class there. I also do guest lectures at Berkeley and Stanford. I am out there in many different ways. I like getting a personal reference from someone who I know because I am out there in different places and many people know me. Having that personal introduction through someone matters most. I get so many blind emails through so many platforms, it is really hard to tell for me which to pay attention to. But when someone I know sends an email to me saying to take a look at something, it makes it easier for me to prioritize that.

Adi 🍍

Now I’m going to have an inbox flooded with “Please introduce me to Gopi.” 

For those of you listening, I cannot introduce you to Gopi. 

Gopi Rangan ☂️

For those of you listening, Adi knows a lot of people. She is extremely well networked. Please email her. If we had that personal CRM to take care of it, we would be good.

Adi 🍍

Here’s the plan: find someone to build the personal CRM. Once it is built, I will introduce you yo Gopi. 

Gopi, thank you so much for your time. I appreciate you coming on the show. I look forward to seeing what Sure Ventures does and keeping tabs on all your cool startups. 

Gopi Rangan ☂️

Thank you so much for bringing me on the show. Thank you for inviting me to share my experiences and vision for how I am going to build Sure Ventures. The spirit of enabling peace of mind for all individuals and businesses is something I hold close to my heart. I am very honored to have the opportunity to share that vision with you and everyone listening.  

Outro

Hi All, thanks so much for joining us for another episode of 90×9, which is sponsored by The Million Dollar Pineapple if you enjoy this content and would like to hear more, don’t forget to subscribe, rate & review this podcast. It helps us to get more amazing guests on here to share their knowledge and experience. After you rate & review we have a special gift for you. Visit 90×9.co/resources and confirm your review to gain access to some exclusive resources curated and created just for you!

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About your host Adi Pineapple 🍍

Adi Soozin recently transitioned from working as the Fast Growth Executive at The Million Dollar Pineapple to the Head of Growth & Operations at 90×9. Over the past decade she has worked as an on-call consultant and marketing freelancer for more than 300 companies throughout 48 countries, across 6 continents. The fastest she has grown a company is from $0 to more than $100,000,000 in sales in less than 5 years.

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