Announcing Redpoint VI

Today we are pleased to share the news that Redpoint has closed Redpoint VI, a $400 million early stage fund. Like its predecessor funds, Redpoint VI will be invested in Seed, Series A and Series B rounds of the next generation of industry-defining consumer and enterprise startups.

Redpoint was founded 15 years ago based on the core values of teamwork, respect and fairness and those principles still guide everything we do today. Since 2014 our companies have had 4 IPOs and 6 M&A events with a market cap in excess of $8 billion.  In total Redpoint  manages $3.8 billion with 434 companies funded and 136 IPOs and M&As.

But numbers only tell part of the story. Redpoint has been lucky to partner with many exceptional founders and develop deep, long-term relationships with people who change the world. There’s no better example than Andy Rubin, the creator of Android, and an entrepreneur Redpoint backed twice before becoming an entrepreneur-in-residence and then joining the firm this year as a venture partner.

Entrepreneurs are re-imagining the world at an ever faster pace. With Redpoint VI, we are excited to continue supporting founders pushing the forefront of technology, creating new markets, and transforming industries as we have with Stripe, Sonos, Twilio, PureStorage, HomeAway, NextDoor, RelateIQ, Zendesk, 2U, Qihoo 360, Kabam, Beepi and Luxe, among many others. We look forward to what comes next in support of the next generation of exceptional entrepreneurs.


Why Redpoint Doubled Down on Infer


When we consider investments, we look at a business’ market opportunity, its people, and its product. If the opportunity is big, the market is bound to get crowded because lots of companies will want to win in that space. That’s why at Redpoint, most of our investment decisions revolve around the people, and we look for teams or DNA that can actually go and win in their market.

We first invested in Infer’s Series A 18 months ago because it fit this investment philosophy. The company had a path-of-revenue product and early success with marquee customers like New Relic, Zendesk and Tableau. We knew that if Infer could prove repeatability and deliver predictive-as-a-service to companies of all sizes, that’d be huge. But most importantly, we were extremely impressed by CEO Vik Singh and his team. They were clearly talented from not only an entrepreneurial and technical perspective, but on the business side as well. With the recent addition of Jim Herbold, who grew Box’s annual recurring revenue from under $1 million to over $100 million, Infer has truly formed a dream team.

As a member of the board, I’ve enjoyed a front row seat as the company’s story has unfolded. Infer has grown revenue bookings 150% quarter after quarter, and consistently boosted customers’ win rates through applications that can be deployed easily by any business. Along the way, I’ve built trust with Vik and been able to see his talents at work. Since I’ve been on the other side of the table, I know how rare it is to find an entrepreneur who is so intelligent about decisions, who understands the strategy, and whom I can respect and challenge because he’s open to suggestions.

When it came time for Vik to raise the Series B funding, he garnered considerable VC interest due to the company’s great traction and vocal customers. At Redpoint, we have so much trust in Infer that we just had to go all-in and lead the B round as well. We have tremendous belief in this A+ team and their ability to win in a hot market, and we couldn’t be more excited about what’s to come.


Microsoft buys Acompli


Redpoint Ventures and I would like to congratulate and thank Javier Soltero, Kevin Henrikson and J. J Zhuang for their amazing insights, entrepreneurship and leadership at Acompli. Today Microsoft announced that they will purchase Acompli.

It is bitter sweet for me. While we are thankful for the amazing ROI that they delivered us, I will really miss working with them hacking on product and business strategy at Acompli. I have had the privilege and fun of working with these guys for literally more than a decade since before Acompli and it has been great every time. Javier was a product guy at heart but always had a great business acumen (Javier and I used to compare strategies on the open source business model back in the day!) while JJ and Kevin are among the best product guys in the messaging landscape (even before JJ and Kevin worked on Zimbra). When these three guys came together to found a company in the mobile mail landscape, it was a no-brainer for us to fund.

Every step of the way, they continued to remind us why it’s so exciting to be in the venture business and work with great entrepreneurs. This is what wakes me up every day – to work with people like them on exciting new products.

While it’s the end of the first chapter of their journey at Acompli, I am confident we are going to see some great new products emerge from Microsoft directly as a result of this team. We wish them continued success in their endeavors.


Backing Tactile’s Series A

At Redpoint, we have been excited about the consumerization of the enterprise for some time. The idea is simple – target professionals inside of businesses with applications that make their working lives more productive. Many successful businesses have emerged that employ this business model. Good examples of these are Yammer, Dropbox and Evernote. Redpoint has invested in this business model as well, backing Expensify and Acompli recently. Today we are excited to announce a third investment – Tactile.

I remember when we hired my first sales guy at Zimbra. He came with a huge cardboard box full of business cards — literally hundreds of business cards each rubber banded into stacks. Fast forward to today, and Tactile gives you a personal mobile app to manage your sales rolodex and your sales relationships individually. Of course, there is a way to publish your contacts and your notes to the corporate CRM (like SFDC). But you maintain control on the individual contacts and meetings and publish it to the CRM system when you deem its appropriate. This is how sales people work in real life, and Tactile gives you a way to do this using a mobile app. Tactile works with your calendar, contacts and emails and gives you an easy way to log and modify existing contacts and meetings. And an easy way to publish it to your corporate CRM.

What makes Tactile even more attractive is that the person leading the effort has incredible experience in the CRM space. Chuck Ganapathy was most recently an SVP of products at Salesforce and brings a wealth of product knowledge in the area. His vision and idea around this space is refreshing, and we are super excited to partner with Chuck to bring this important sales productivity app to the market.


Backing Acompli & the Value of a Veteran Team

Last year, I wrote this post detailing what I would do if I was starting my last company, Zimbra, today. I wrote about the massive opportunity for a smart company to serve the professional market with a real, thoughtful solution for mobile email. Just a few months later, I was lucky to begin working with the team answering this exact challenge: Acompli.

Today, we are thrilled to officially welcome the Acompli team to the Redpoint portfolio. Backing their Series A was an easy decision. They have an incredible, proven team at the helm of an amazing product.

Javier, Acompli’s CEO was an EIR with us here at Redpoint after he sold his last company to VMWare,  Co-Founders Kevin Henrikson and JJ both worked with me at Zimbra, and Kevin was an EIR with us as well – albeit shortly, as he and Javier quickly got to work on Acompli while here at Redpoint.

Beyond their incredible product and vision, the value of a proven team like Acompli’s is huge. In this video, Javier and I discuss the pros and cons of working with startup veterans, what went into building the initial Acompli team, and how Javier is approaching being a CEO the second time around. Enjoy, and request your invite for Acompli today!


Email Again

I think it’s time to revisit email. revealed the demand in the market for a better mail client. But I think more can be done and a venture scale company can be built around email, particularly corporate email.

Microsoft Exchange dominates the corporate email market with greater than 60% market share. But that seemingly unshakeable grasp is showing weakness because of the lack of innovation in the core product, powerful mobile app distribution channels and the BYOD/consumerization of IT waves.

It has been proven that you don’t have to sell to IT anymore. You can sell directly to the consumer who happens to work in a business and flood the business with your software without the IT team knowing about it.

Through my days at OneBox and Zimbra until now, I’ve built a deep passion for email. If I were to start Zimbra now, this is how I would approach the market:

First, build a beautifully designed mobile email client that talks EWS/AS to Exchange and is available on iOS and Android.

Second, develop an email client with a built in social feed for all those people on the same domain as a left shelf. One tap to post your location so you can tell your co-workers you are traveling or working from home. One tap to share the latest news on a sales call. The right shelf is an attachments and files browser combining Dropbox and Box files with email attachments.

Third, enable full text indexing of all emails in the cloud so it’s easy to search for everything. i.e. bring a Gmail like experience to exchange of fast and effective searching.

Fourth, embed gesture based shortcuts within the mobile client. Unlike keyboard, a smartphone has a much more sophisticated input system – the touch screen. Users could configure gestures not just for simple actions like delete and spam but more complex actions. For example, a single tap responds to a message with the answer “Yes” and a double tap will reply with “No.” A three finger tap might add an appointment to the calendar; something else would add a map of your current location to the body of a mail. And a pinch might ask the app to read your calendar, figure out who you are meeting with at this hour, emails everyone on the invite with “I am running late!”

Fifth, automatically generate a whitelist for your inbox to limit junk. Everything whitelisted is prioritized and the rest is put into another folder. The whitelist is created from implicit signals when you use the app. Every email recipient from your account is automatically whilelisted, as are CC’ed people, and everyone in calendar invites. Also, imagine a one button unsubscribe within the app to quickly triage junk.

Last, to-dos and notes should be integrated into my inbox and appear like emails. Alongside the compose button for email, there should be text box to quickly create a task. Every task appears in my inbox like an email. Emails, Tasks and Notes have a subject, a body and attachments (optionally). I think a fully searchable and mobile mail product can store notes and tasks the same way it stores email. It’s a matter of UI to surface it right. Deletion is the same as completion of tasks. A note to self is the same as an email without a sender and a recipient.

The business model is self-evident: pursue a direct to consumer, bottoms up freemium approach with a top-down sale to IT.

Ideas are dime a dozen… execution is everything. If there is a world class team going after this area, I would love to be part of the journey.


Behind our latest investment: Infer’s Series A

The best part about this job is serendipity. You walk in to a meeting any day of the week and you might just find a deal that you totally fall in love with. That’s what happened when I caught up with VikSingh from Infer one morning a while back.

We believe Vik and the Infer team are building a category defining SaaS company  that leverages data science to help businesses identify their most valuable potential customers. Infer is a customer intelligence platform built by crawling your own historical selling patterns and matching it with the vast swaths of data on your potential customers available across the web. This level of customer intelligence has already drastically improved top line growth for all of its current customers.

At Redpoint, we have been looking for “path of revenue” deals. We define “path of revenue” products as those that help other companies grow their top line revenue. Salesforce is the quintessential example of this type of product. Two of our portfolio companies, Zendesk and Zuora, also have created products that help companies grow their top line revenue. We like this category because of the fundamental belief that CEOs will always find budget to grow revenue irrespective of macro factors at play. Infer and its solution directly benefits top line growth and fits in very well with our thesis. This has been ratified by the enormous sales traction that the company has enjoyed thus far – signing several multi-year agreements with customers who have seen their own sales/win rate double since they started using Infer.

But that’s not the most interesting part of Infer. In my mind, there are two reasons why we think this is going to be a very special company. First, their solution is unique and completely differentiated from everything else we have seen in the market. Most sales lead scoring or marketing automation platforms do not have the kind of technical prowess that Infer has. And its not technology for technology’s sake. It’s the first real application of big data, machine learning and predictive analysis to build a customer intelligence platform. A platform that directly benefits revenue growth.

Second – we just loved the founding team. Vik, Yang and Chung were crazy smart guys and worked really well together as a team. It’s always refreshing to see founding teams that have had a long history of working together. Vik has built a formidable tech team at Infer and was a big reason for our investment. He is a rare technical talent – but the most impressive thing about him is how good of a business leader he is. He understands the complications of the market and the go-to-market implications really well. He is thoughtful and open about the challenges and the opportunities in the market. He surrounds himself with great people and is strong willed and decisive yet open minded to hearing suggestions. In short, Vik is the kind of founder/CEO we like to back. Then we broke some bread and had some sake… it was clear that the cultural fit with Chung, Yang and Vik couldn’t be any better.

We are really excited to welcome Vik and Infer to the Redpoint family and look forward to building a great company together.



Four Common Founder Mistakes

Over the years, as both a founder and an investor, I’ve witnessed a mix of the great choices and mistakes made by entrepreneurs at the earliest stages of a company’s growth. This year is no different than previous years. Macro-economic forces are always changing, and all founders can do is plan for the worst while they work tirelessly to make the most of the initial capital they secure.

Here are a few things to keep in mind to avoid the common pitfalls I have noticed:

1. When the pitch is over, it’s time to be transparent with your board. Once you close your initial funding, it’s extremely important to be transparent about all the issues your company is facing. Is your VP of Engineering not working out? Maybe the product isn’t where it should be. This is the information your board needs to know. There’s a tendency for entrepreneurs to stay in pitch mode after the money has crossed the wire into their account, but this isn’t necessary. In fact, it can be a huge detriment to a startup’s success. In my experience, when a founder isn’t transparent, it’s the relationship between the investors and the founder that suffers. Over time, this lack of transparency can eventually lead to a failed company. Remember, your investors are your partners. Tell them what keeps you awake at night. Be honest. Time is your enemy with a startup, so tackle any problems early on.

2. Don’t confuse management with leadership. This is probably the biggest lesson that early-stage founders should take to heart. You might think you can handle all of the functional roles a successful company ought to execute on (engineering, marketing, business development, sales, finance, etc.) — but you can’t. Be realistic and hire some great managers to join your team. This will allow you to focus on the bigger picture of company vision, capitalization and hiring. Founders should lead the company — not try to manage every functional role in the company.

3. Plan for capitalization before it’s too late. I’ve found that 50% of the time startups might not be able to execute on plans based on reasons outside of their control – be it the changing competitive landscape, macroeconomic factors or some geo-political disaster that changes the capital markets. The only way to plan for the unknown is to have runway. All too often founders wait too long to start raising money for the next round of capital, and then they end up running the business to the wire (or worse, to the ground). Early stage companies should always have a solid runway of at least six to eight months left in the bank as they start fundraising for the next round. This is imperative to ensure making it through the unknown. The best way to do this is to discuss and plan clear milestones, future capital requirements and runway left at the very first board meeting. Always have a shared understanding with the board on when to raise capital and the proposed state of the business at the time of the next raise.

4. Admit failure when failure’s had. Startups are about learning to fail fast and course correct quickly. Maybe the choices you so enthusiastically convinced the board about didn’t pan out the way you hoped they would. If that’s the case, then fix these and fix them fast. The more agile you are with correcting mistakes, the more ahead of the game you’ll be. In addition to fixing mistakes quickly, it’s also important to not be afraid of making those mistakes. This is how you’ll learn. Follow your passions and your gut. If you execute on your plan and your idea flops, don’t be afraid to admit to the failure, but pick up and move on right away.

 *Originally published in the WSJ Accelerator Series on Monday, see the post here.


Redpoint invests in Big Switch Networks

Redpoint Ventures is proud to announce our investment in Big Switch Networks. We have been looking at data center architectures and how they are changing for a while now, being first exposed to that through our investment in in 2009. While selling private clouds, we realized how dramatically cost efficient compute could become — but at the same time we were constantly reminded of the limitations of storage and the limitations of the old networking architecture.

Since then, we have been searching for a team and an architecture that would usher in the next era of networking.  We were closely following the OpenFlow movement that was being led by Guido Appenzeller at Stanford University. Being strong believers in an open ecosystem, we knew that what Guido and his team were doing was the right way to build an open and extensible network architecture. We were delighted when Guido teamed up with Kyle Forster to found Big Switch. With Howie Xu, who led the networking products at VMWare in the mix, this was the dream team we had been waiting for. And we knew that OpenFlow and Big Switch were going to disrupt network architecture in data centers. This was completely confirmed in our various customer interactions where we consistently kept hearing how efficient, easy to manage and cost effective their solution was.

All of that is why we are honored to be partnered with Guido and Big Switch and to be able to participate in the disruption they are causing by their new open network architecture. We are just at the first innings of some big changes to data center architectures – and that is very exciting.


Announcing our investment in Zendesk

Today Redpoint is pleased to announce that we are leading a round of financing at Zendesk. Zendesk is one of those companies that has re-defined the SaaS landscape. Not only did it dramatically simplify a complex and old software category with a beautifully simple UI, it also embraced the emerging social media channels for providing customer service. It is very obvious now that having a great customer service experience can dramatically improve brand equity. Zendesk removes all of the software complexities that block companies from achieving that goal. When we think about investments, we worry about market, ideas and people. It was clear from the outset that this market was huge and the existing software solutions were tired and old. There were huge disruptions happening in social media and customer support must evolve with that, in addition to the traditional methods such as email. We also believed that this category of enterprise software will see a dramatic shift towards the cloud and a fresh, new, simple, flexible hosted solution that can interface well with other 3rd party services can and will disrupt this industry.  We believe Zendesk is that company and their market and revenue traction already prove that they are well on their way.


When I first met Mikkel for breakfast in the spring of 2009, he was already talking about freemium models and how it will allow him to sell without an enterprise sales force.  It is important to note that he was already doing this for a year by then and that he was way ahead of the times in leading this massive move to the freemium business model. It seems so obvious now, as a lot has been said and written about this way of selling software in the last few years, but Mikkel had this vision 5 years ago and was among the first to invent this business model. Last year, my good friend, Alan Black joined the company as CFO. I know Alan from my days at and respect him and his work immensely. I know Zack Urlocker well from our days together fighting the good open source fight. I know the board members, Peter Fenton (he was an investor in Zimbra and I respect his governance a ton) and Devdutt Yellurkar (whom I know and respect as a friend).  We knew that this was a company that not only had a disruptive product and a disruptive business model in a big market but they had surrounded themselves with world class people.


We have followed Zendesk for quite a while and are big believers in the market and the people. But, most importantly, we had such a great feeling about the business model that they are pursuing, and that a category defining company is being built here. So far, no one can dispute that Zendesk is one of the leading companies in the SaaS category that pioneered the freemium business model.