An Interview with Scott Raney, Managing Director, Redpoint Ventures

Scott invests in entrepreneurs at the seed, early and growth stages with a focus on cloud infrastructure, open source and SaaS. He’s especially interested in the rise of distributed computing and developer-facing businesses. Scott serves or has served on the boards of Guild Education, LaunchDarkly (an Alchemist company), Hashicorp, Platform9, Sourcegraph and Twilio, and led Redpoint’s investments in Stripe and Collective Health. Past investments include adap.tv (acquired by AOL), Cloud.com (acquired Citrix), Heroku (acquired by Salesforce), Jumptap (acquired by Millennial Media), and RelateIQ (acquired by Salesforce).

Prior to joining Redpoint, Scott was responsible for new products at NorthPoint Communications, a data CLEC providing nationwide DSL services. Prior to NorthPoint, Scott worked at Bain & Company helping clients in the private equity and technology industries.

Scott, how did you get into the world of Venture Capital?

I’d worked as a developer, product manager, and business development manager at a variety of companies including a couple of startups. I had a passion for entrepreneurship and technology, and I had an opportunity to join Redpoint as an associate a number of years ago. I’ve been lucky enough to get promoted a number of times and be in a position to work with a lot of really great entrepreneurs over the years. It's been a lot of fun.

You said you were a developer. Is that what you graduated college with?

I graduated with a B.S. in Electrical Engineering and had done a bit of software development as a part of my academic career. Then I joined, what at the time was called Andersen Consulting, but is now Accenture, as a software developer and, among other things, worked in their Advanced Technology Group. I did a lot of software development there at the dawning of client-server, and also got exposed to networking and communications and really fell in love with that.

Is your background in software development what led to your investment in LaunchDarkly?

I'm going to take it back a few years to 2007 and the launch of Amazon Web Services. As a former software developer, I saw the impact that would have on development, but also the emergence of this trend called DevOps, that we all know and love today. I met the founding team of Heroku, which was building the first PaaS (Platform as a Service.) Through that experience, I developed a deep admiration for entrepreneurs working on building products that developers love. You’re not selling products to developers, but you're selling through developers to organizations to solve big business problems. Heroku is near and dear to my heart and I learned a lot about the power of developers through that time. After that, we invested in companies like Stripe and Twilio and another company called Sourcegraph that's working on “code intelligence” again to help developers accelerate writing software. Through these experiences I was lucky enough to meet Edith and hear what LaunchDarkly was doing. It felt like it was the perfect continuation of that trend. It’s a piece of technology and a solution that helps developers, but ultimately unlocks so much value across an organization and could have a profound impact on how they think about their business.

What separated them from the other investments you were thinking of making in the space?

The things I look for when we find these developer-facing businesses are indicators that the projects have impact not just within the development organization, but with other functional areas. By changing the software development lifecycle, these companies can end up having repercussions that affect product, marketing, and even senior level decisions how a company runs its business. LaunchDarkly was an amazing example of that, through the idea of feature flagging: the ability to transform the velocity at which you could release product; the ability to give product managers control to deliver specific features to individuals; the ability for marketing to be able to provide early looks on functionality. These are interesting, profound capabilities that span across an organization. Maybe the most exciting thing to me is, we talked to one of their early customers during the due diligence. It's a very successful, large company today, a brand name. We talked to the CEO who was not only aware of the impact LaunchDarkly was having on the organization, but talked about how it impacted the way he managed the business. It changed the way he thought about what his team could do. I was incredibly excited when I heard that, because that’s the way you create massive value and have the opportunity to build a significant business.

What are your thoughts on Alchemist in general?

I love what Alchemist is doing. I think it’s clear that when Alchemist got started, there was a dearth of opportunities for entrepreneurs thinking about enterprise businesses to find mentors and advisors and organizations that could them to help them grow those ideas.  Ones that understand the nuances associated selling to enterprise buyers. There were things like this available to consumer and more consumer-like enterprise businesses, but there were very few people that could act as a resource for entrepreneurs who wanted to build traditional enterprise businesses. I've heard time and time again from the people that go through the program just how much value they're getting out of it. I don't want to suggest here that building a consumer business is easier than building an enterprise business, far from it. They're very hard, but they're very different. As a young entrepreneur, when you think about selling to businesses, there's some realities you just have to know. You have to understand what it means to build an enterprise-grade product. You've got to understand what it takes to market to enterprise buyers, and you have to understand what it takes to build and manage a sales force that can sell to enterprise buyers. Having an organization that helps young entrepreneurs understand the importance of all those things and what it means to do that is invaluable. I view it as a pretty unique entity in terms of what it's doing. The entrepreneurs that have been a part of the program say it was incredibly helpful.

What’s the size of Redpoint, and how does it compare to other funds of similar stage in the Valley?

We’re a unique animal in that we are always actively putting money to work out of two funds simultaneously. We have an early stage fund that is $400M focused on Seed, primarily Series A and occasionally Series B. We also have a $400M early growth fund that is focused on Series Bs and Cs. As a result, we span from Seed all the way through mezzanine financing with these two funds totaling $800M.It makes it a lot of fun for us. Our approach in the way that we we work with entrepreneurs, is they do not need to worry about which fund the money is coming from. Here we're going to work every deal exactly the same with an identical approach to thinking about engagement with entrepreneurs and the value that we want to add to them. We just have two pockets we can pull from.

What size checks do you typically write and how is that structured?

It's a hard one to answer given our stage-agnostic approach.  We write seed checks of a few hundred thousand to grow checks well north of $30M. The most important thing for us is to not try to force an entrepreneur to raise an amount of money that isn’t in the best interest of their company.  Ultimately, we want to do what is in their best interest and the good news is we have the flexibility to support a couple of smart people with an idea all the way up to a company well on its way to an IPO.  

What stage do you prefer to enter into, if there is a preference?

The earlier we can be involved with great entrepreneurs, the better, but again we are primarily interesting in working with great companies regardless of stage.  

Does your fund have a specific focus?

Broadly speaking, Redpoint invests in disruptive ideas across both enterprise and consumer technologies. That being said, with the rise of things like artificial intelligence and what's happening within SaaS and cloud, we're finding ourselves moving into adjacent markets. We've been spending time understanding how things like machine learning can transform the drug discovery process and the delivery of healthcare. We are spending time in areas like space and robotics. We have a pretty wide aperture. The common denominator is we are looking for bold ideas.  Companies that are building innovative technologies and that have the chance to fundamentally transform a market.

How do you think your fund differentiates itself from other funds?

First and foremost, it starts with entrepreneurs. Few jobs are as challenging as that of a founder creating and scaling a business; our team’s job is to work collectively for our founders and help them build successful companies. We view ourselves as going to work for the entrepreneurs, as opposed to them going to work for us. It’s a privilege.  

As a firm, we’re very collaborative in nature and we take a team-based approach. Most of our team have been former operators or founders ourselves and we have a deep empathy for the entrepreneur’s journey. We try to operate like a startup ourselves with a small and nimble team. Our firm’s 19 + year legacy gives us a fair amount of experience, perspective and connections, as well as a foundation for doing what’s right for the entrepreneur.   

The last thing I would say is that we really have deep domain expertise and we invest a lot of time and energy in building the networks and relationships around the thematic areas we invest to make sure that we can make a difference. This allows us to see over the horizon, and help our companies do the same.

How do you think you individually differentiate yourself from other VCs?

I try to be the best possible partner that I can be. I've been lucky enough to be a part of a lot of great companies and to have had a chance to work with a lot of great entrepreneurs. I hope that when they sit down across the table, they'll say “This is somebody who helped me, who had my best interests at heart, and who was great to work with.”

The other thing is just try to be a good human being. This is a long term relationship and we’ll be working with these folks for many, many years. The last thing that an entrepreneur needs is to be dealing with somebody that isn't 100% aligned with them and has their best interests at heart. I try to make sure that I'm always looking at the world through their eyes and trying to be as helpful as I can.

What makes an investment compelling for you?

It starts with the team. We spend a lot of time in our diligence process assessing whether or not we think a team has the opportunity to build something really differentiated and transform whatever market or industry they're part of. That is top of our list, bar none. We want to work with good people that we think are going to do things the right way. Second, we look at the markets the companies are operating in. We want to be going after big markets and taking bold bets. The last thing is we look for products and technologies that are differentiated and will create defensible moats making  it difficult for other people to replicate.

That used to stand primarily on the basis of high quality products and good technology. Increasingly, a lot of businesses we look at have other moats like network effects that can be extraordinarily powerful for businesses. In enterprise increasingly there are communities that get built up around some of these technologies. We put that all together and try to find things that are special and where we feel we can add value.

Bottom line is, we want to work with great people, and they come in all different shapes and sizes and all different experience levels. We've been fortunate to work with a lot of folks who are building amazing businesses as their first job. We've also been very fortunate to work with experienced executives who are doing it for the second, third, or fourth time. In the end, we don't think that talent comes in one shape or size or profile. At some level, to be a great entrepreneur, it’s some magical combination of intelligence, grit, determination, and experience. There's always a different combination of all those things, but in the end we think that people that have a vision for the future and have the ability to get it done are what matters the most.

Is there was a piece of advice that you could give to founders fundraising, that doesn’t get shared enough, what would it be?

The more honest and open and transparent you are, the more likely you're going to find somebody who is investing for the right reasons. I encourage everybody to make sure that you're not trying to manage the conversation. As an entrepreneur you need to be able to sit across the table from your investor and lay it all out there - the good and the bad - and get an honest reaction. It gives me great comfort when founders name the issues or challenges in their business because I don't feel like I'm being managed and I don't feel like there are things I don't know. Obviously, things are not always going to be going up and to the right. Every company has things that need to be worked on. Once I know what the issues are, it's much easier for help the entrepreneurs. There are a number of founders in these conversations that feel like they need to come off as infallible and “we've got this, it's all good.” No business is like that.

Which investment are you most proud of and why?

I love them all the same! But Heroku is special to me because it was my first investment.  It wasn’t obvious at the time, but I loved the founders and their vision.  Seeing their success was incredibly gratifying. As with all our founders, I am forever grateful to have had the chance to work with them.  

What areas are you excited about now and in the future?

It's a broad question and I don't think I'll be exhaustive in my answer. I will tell you where I spend a lot of time personally. I believe in this move-the-cloud-native movement - this move away from traditional monolithic to microservices and from on-premise to the cloud.  These moves are having profound repercussions it has in terms of software development, deployment, and operations, and also the impact it has on a company’s ability to move faster than ever through software. You can look at every tier of the application stack and realize that they're going to be fundamentally changed. Many already have been, but there are many things left to do. I'm a big believer in things which help organizations move to the cloud. I’m a profound believer in the power of the public cloud and the long term trends there. All the solutions that help companies begin to make that migration, I'm very excited about. We continue to be interested in SaaS in the way that it’s moving beyond broad horizontal applications and into more vertical solutions that do more than just automating a business process, but really help people do their jobs better by delivering insight. We continue to be excited about the long term trend trends there. And as I mentioned earlier, we're very interested in broad applications around AI and ML and in particular how these technologies might disrupt industries typically not addressed by venture capital.