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“There was never any trust there. He was constantly conspiring behind my back with the other board members. At the board meetings, it was clear that he was leading a bunch of side conversations…”

I heard this quote from a CEO I had called for a backdoor reference on a potential board member for IronPort. It instantly made me realize the importance of transparency between a CEO and his board. If I were to totally suck at being a CEO, I wanted someone who would have the hard conversation with me. How else does someone learn and improve?

As a first time CEO, I wasn’t sure if I would scale to run IronPort long-term. But I wanted a legitimate shot at it. And I wanted a board member that considered the company’s interest first, but was also committed to helping me become a better CEO.

I will never forget that backdoor reference because it made me think twice about the fundamental skills and characteristics I wanted in a board member. Early on it became clear that transparency and the ability to provide honest feedback were paramount. I learned this through receiving instant and honest feedback following every board meeting (a healthy board practice). When this was coupled with annual 360 performance evaluations I always knew where I stood. The feedback was crucial for my growth.

In addition to transparency and feedback, through my own personal CEO journey, I came to realize that the following represents table stakes for the best board members:

Experience: I wanted someone that had been there, done that. In addition to the investors, I went out of my way to recruit three CEOs to the IronPort board because I wanted to surround myself with people that could help steer me around common potholes and would be unflappable as things were going haywire. Diversity of experience was also very helpful. Some of my board members had been on 50 boards while others had run large direct sales organizations; both contributed in completely different ways. If given a choice, I don’t see why any entrepreneur would take a term sheet from a VC with little or no board or operating experience.

Sharp opinion: Quiet is not helpful. A Melvin Milquetoast who sits there nodding his head all meeting is not helpful. I wanted someone who consistently contributed meaningfully and constructively to the conversation, however wide ranging it became. Every board member slot is an opportunity to find someone truly amazing who will speak up and help you build your business. The traditional “financial expert” as a board member essentially compromises a valuable seat with a former CFO or accountant that rarely contributes outside of their domain. It’s worth working hard to find a CFO that later became a CEO or interviewing hard for a financial expert who really contributes. The thorniest business problems will surface at the board meetings and the different, sharp, opinions help to to better explore the poles of the arguments to make better decisions.

Responsive: Board members need to respond to texts within hours and emails or phone calls within 24 hours – no excuses. Things move fast at startups and when I needed help with a lawsuit, contract, employee situation or financing, I wanted to have a damn batphone with my board members. Yes, I realize that I was not in the business of saving lives, but the difference between landing a rock star candidate or closing a round often depended on the timeliness of a board member’s response.

Does real shit: Being on a board is not just about showing up for the meetings. A board member needs to materially contribute to the success of the business. This includes making numerous introductions to potential customers, partners and employee candidates. This is in addition to being available to interview/sell employee candidates, coach management team members, speak at sales kickoffs or just about anything reasonable that a CEO asks you to do to help the business.

I once had a venture capitalist explain to me that a board doesn’t have many options when it comes to affecting the direction of the company. That if you don’t agree with where the CEO is leading the company, you basically have two levers: 1) threaten to fire the CEO, or 2) fire the CEO. He also added that the former gets pulled much more often than the latter. This describes well the authoritarian and adversarial nature of many CEO-to-board relationships. Given the makeup of most boards, where most of the members lack the practical experience to help coach the CEO, the lever approach is not all that surprising. But like any bad relationship, it’s something to avoid.

The best board members aren’t elected by default. CEO’s that set themselves up with their choice of board member – which means getting more than one term sheet and doing extensive reference checking – are better off. You want to find a coach, not a lever puller.

All great pitches have a few things in common: the founder/team is wicked smart, the idea is big and a breakthrough, and the market is potentially enormous.

But the best pitches are also usually non-obvious and unique to the particular entrepreneur’s story and background. “Founder/market fit” is important. Does the founder’s life story, educational background, personal struggles, Ph.D thesis, or prior work experience somehow qualify them to unfairly prosecute the opportunity they are pursuing? At our firm we always start off our meetings with a deep dive into the entrepreneur’s background, and the most convincing pitches literally pour out of them with some deep connection or “aha” that led them into the business they are explaining. By doing so, the idea is unique/original and is presented authentically versus a canned sales presentation.

A lack of originality and authenticity is probably the biggest turnoff. Stereotypically, this can be a couple of MBAs that have been churning through different business ideas in order to find something that might make them rich. Or it could be a hired gun/former sales VP as the CEO adopting or explaining someone else’s idea. In both cases, they typically have done a superficial, McKinsey-esque market analysis but have no passion or connection to the business.

Another important quality of a “perfect” pitch is when a founder exudes in many different ways, the confidence and courage to go the distance, against improbable odds, to make an enduring or lasting business. They come off as expertly informed, determined and unflappable during the hard questions. And they usually lay out a series of chess moves that reveal an even bigger ambition: “If we do this, then we can do that…”

A lack of confidence is also a huge turnoff – usually typified by a single slide in the deck entitled, “Exit Strategy or Exit Options.” This is the kiss of death for our firm.

This post originally appeared on the WSJ Accelerators Blog.

One of the most famous hackers in the world, Kevin Mitnick, published a book about his exploits — “The Art of Deception” — after he got out of prison. This guy broke into corporations, government agencies – even the FBI cell phone network to find out they they were closing in on him. Surprisingly, the most interesting “a-ha’s” of the book weren’t related to his prowess behind the keyboard but something much simpler — he was a master of “social-engineering.” Kevin would get unsuspecting staffers on the phone and trick them to reveal passwords, backdoor locations, and critical tidbits of information to enable his hacking. He used well-worn techniques like urgency, name-dropping, and a folksy familiarity that were popular in the Depression era and updated them for the modern times.

Kevin Mitnick was not alone.

Most of the largest online fraud hauls begin with a live telephone conversation. The existing caller ID infrastructure is useless as there are plenty of software options available for fraudsters to spin up millions of fake numbers and spoof the origin of the call. Quite honestly, there really isn’t a good way to authenticate who is on the other end of the line other than a series of painful security questions and even those are getting harder — my great aunt’s maiden name? There’s just got to be a better way…

While working on his PhD degree in 2009, Vijay Balasubramaniyan, had an unusual thought: could each phone call possibly have its own unique acoustic signature? Specifically, are there patterns in the sounds, packet loss and latency that could tell you the network, phone type and specific location the call was coming from? After some investigation, Vijay decided to focus his efforts on proving out the technology and the results became the core of his PhD thesis.

In 2011, Vijay completed his studies and hooked up with Paul Judge, a fellow Georgia Tech PhD alum and security industry veteran, to co-found Pindrop Security. The company’s technology is a commercialization of Vijay’s unique primary research and patents. Pindrop provides an enterprise solution that helps prevent phone-based fraud. Vijay’s pioneering acoustical fingerprinting technology detects fraudulent calls and authenticates legitimate callers, helping customers eliminate financial losses and reduce operational costs.

I’m very pleased to announce that Andreessen Horowitz will be leading Pindrop’s $11M Series A financing round. Our friends at Citi Ventures, will also be participating in the financing round. Here’s why we’re so excited to work with Vijay and Paul:

Founder/market fit. This is really our kind of opportunity — a very unique technology with virtually all the intellectual property invented by the founder. And it works! Vijay developed and patented the core technology while pursuing his doctorate at Georgia Tech, a school renowned for its cyber security and signal processing research.

Focus on voice fraud. As much as we talk about data overtaking voice — every customer we talk to has seen voice calls increase linearly with customers. And voice is becoming even more of an attractive alternative for fraudsters as the online channel is maturing and becoming more secure.

Very differentiated technology. It’s a very differentiated solution and the only one that isn’t purely fingerprint based so it detects zero-day attacks. Customers rave, “we are finding whole new fraud rings that had previously gone undetected…”

A track record of execution. Since we participated in Pindrop’s seed financing, Vijay and Paul have executed to plan in a remarkable way — they launched the product and had a stable of excited, apostle customers. The game film on their progress has been universally positive.

I’m super excited about joining Pindrop’s board of directors and look forward to helping Vijay and Paul bring this technology to everywhere people are answering phones and wondering who is on the other side of the line…

When I first met Logan Green and John Zimmer nearly a year ago, I was struck by the authenticity of Lyft’s founding. Originally called Zimride, everyone assumed the company was named after John but it’s actually a much better story: When Logan was traveling in Africa — Zimbabwe, to be exact — he noticed that despite the lack of infrastructure, people were able to get around efficiently thanks to a vibrant ridesharing movement. Every car, van and bus was full and people would literally stand on the side of the road waving money instead of sticking out their thumbs.

African Combi

At nearly the same time, John was sitting in a college course exploring the history of transportation: canals, trains, and then roads and planes. He wondered to himself, what would be the next big innovation in transportation? He thought, “I’ll bet it’s about using information to fill seats — especially all those empty seats in cars.”

I’m acutely aware of John and Logan’s observations when I’m sitting alone in my 7-passenger minivan on the 101 inching along while others are zooming past me in the High Occupancy Vehicle (HOV) lane. These are times when I really wish I had a few extra people in the car! But it’s just not that simple — I don’t want to go way out of my way and I want to feel comfortable picking up someone new.

With this unique vision in mind, John and Logan went about launching Zimride and Lyft. The information technology problem was essentially solved with the proliferation of GPS-enabled smartphones. If they could get a critical mass of people on the same network with information about when and where people wanted to go, it would be relatively easy to pair up drivers and riders that were headed in the same direction. But how to get it started? And what about safety?

The first incarnation, Zimride, launched in 2007, tackling these issues by targeting college students headed home on holiday. Logan and John’s big insight was that by using Facebook profile information via Facebook Connect, both the drivers and the riders could find out about each other to develop enough trust to get into a car together. As a driver, you’d post the where and when details of your trip and then passengers would apply for a ride with a predetermined chip-in. Over the years they have showed steady and solid growth and built a real community of people making friends and sharing rides.

Last June, they launched Lyft in San Francisco, a made-for-mobile, ridesharing app that was geared towards ridesharing within a city as opposed to between cities. Since its launch, Lyft has absolutely exploded and is now doing over 30,000 rides per week! Now active in four major cities and expanding at a blazing pace to meet demand, the key for Lyft has been the community. Lyft has a very different offering and experience than anything else in this space. To be specific:

–  Lyft is all about taking cars off the road via ridesharing. This is NOT merely a cool new use of technology to efficiently onboard and route more cars, cabs, towncars and limos. Lyft wants to use technology to get everyone who currently owns a car to join a trusted information network to share rides.

–  As such, the Lyft drivers are regular folks with underutilized cars. They are college students, engineers, entrepreneurs and retirees. As the founders like to say, a Lyft driver is “your friend with a car.”

–  As demonstrated by Airbnb, the person-to-person sharing economy is all about earning trust and establishing a good reputation. If I am going to rent my spare bedroom or get into the car with someone I don’t know, I have to find a way break the trust barrier. Lyft requires all drivers and riders to connect through Facebook. They have intentionally limited the potential market to people who have established social network identities as a way to improve trust and safety. The drivers and passengers also rate each other after each ride to further build their reputations.

–  Lyft screens their drivers with interviews and full background and DMV checks. They are looking for real people with great driving records and a knack for hospitality.

–  You also get to ride up front in a Lyft. As the car pulls up with its unique pink mustache on the front (as John says, “it always brings a smile!”), you jump in the front seat and do a ceremonial fistbump with the driver. You are offered a phone charger and the chance to play DJ for the ride. Many of the drivers I’ve ridden with even offer something unique and fun like Capri Suns or snacks for the road.

Lyft is a real community — with both the drivers and riders being inherently social —  making real friendships and saving money.

I am pleased to announce Andreessen Horowitz’s partnership with Logan and John. We will be leading Lyft’s Series C financing round of $60 million to propel the Lyft movement globally. I am honored to be joining the board of directors and excited to help the founders realize their dream of filling all of those empty seats!

Ben Milne has a special relationship with transaction fees.

An entrepreneur with a design and manufacturing business in Iowa, Ben found himself obsessed with one simple notion: transaction fees were eating into his profit margins. If you consider money as data, there had to be a better way with so much money sloshing around in the system when the marginal cost of actually transferring the money is practically zero. So why did it cost him $55,000 a year to access it? Why then did he have to wait seven days to get paid?

This is the frustration out of which Dwolla was born. Ben set out to redesign a much better, and radically cheaper, payment network.

But how in the world would he scale a new, two-sided payment network today?

The PayPal and Visa stories are well documented. Visa’s story is famous. A genius by the name of Dee Hock pioneered a brilliant strategy that empowered a loose association of affiliates to distribute the card all over the world, almost entirely manually. And while eBay was distracted building and scaling their marketplace, PayPal snuck in to become the defacto standard for eBay transactions between individuals. eBay bought a competitor and tried to unseat PayPal but the network effects were just too strong and they ended up having to buy PayPal for $1.5B.

So how would Ben do it then? This is the beauty of his approach at Dwolla. Ben began designing a system based on the impending ubiquity of the Internet; something consumers, banks, businesses, and developers had immediate access to on their phones and computers. This would give Dwolla the ability to bypass the traditional systems, hardware, and distribution costs associated with the card networks birthed in the 60s and 70s.

Dwolla moves money for only 25 cents and can do so instantly (versus two to seven days it takes other processors). Signing up is free and there are no other costs. Not counting the hardware, gateways, and hidden fees, businesses and consumers were paying three to eight percent per swipe, adding up to over $48B in 2009. Ever walk into a bar, buy a drink and been told, “there’s a $10 minimum to use a card?” Yeah, that’s why.

What’s astounding? In addition to payments only costing 25 cents, transactions under $10 are free — this opens up a huge opportunity for Dwolla to be the defacto standard for micropayments. This “flat fee or free” pricing model strategy is such a compelling value proposition that large players, like the state of Iowa, are signing up for Dwolla in droves.

What about checks? Small business owners and consumers know the pain points associated with manually processing checks all too well and all the problems with the slow, antiquated Automatic Clearing House (ACH) network. How much does it cost to do a wire? $50? $10? That depends on where you bank. But either way, ouch.

These slow-moving, expensive, fraud proliferating systems aren’t just the United States’ burden. In many countries around the world, the luxury of ATMs, having cash on hand, or retaining the value of money as it moves from one person to the next, just isn’t possible. In many developing areas, networks charge up to 30 percent of a transaction because of the way you paid for a particular good or service.

The world needs a better way to transfer value, the same way it needed a better way to transfer information before the Internet went mainstream.

Now here are the other wonderful parts: Dwolla has created straightforward APIs, simple user experiences, social integration, and one of the United States’ most sophisticated and advanced banking software, called FiSync. And whenever Dwolla signs up a new customer, those users now send out their payments via Dwolla. The payee is then highly motivated to activate and bank-enable their Dwolla account to claim their cash. It’s natural convenience.

I am pleased to announce Andreessen Horowitz has led a $16.5 million investment in Dwolla to help Ben and his team realize their vision of fixing the worldwide payment network. Here’s why we believe this is such an amazing opportunity:

  • Founder/market fit: Ben is one of the most determined and scrappy entrepreneurs we’ve met and has a deep knowledge of the entire payment network.
  • Ridiculous market size: Dwolla’s FiSync is taking on ACH and FedWire, a combined $730+ trillion market with real-time transactions, new revenue streams and incentives for key players in the payment process.
  • A snowball of traction: Its annual processing run rate has moved from the hundreds of millions to billions and its business development pipeline is chock full of opportunities.
  • The simple strategy of “natural convenience.” Especially as it pertains to ACH and payout needs, Dwolla offers an easy-to-use platform for payers and a free, low-cost platform for payees.
  • Radical innovations in anti-fraud and risk management technologies: For example, Dwolla removes much of the sensitive financial information, which is often exposed when someone uses a paper check or plastic card, from its transactions. This reduces liability for merchants and developers, and mitigates the threat of identity fraud for its consumers. Genius.
  • One of a kind technology: Underneath Dwolla’s beautiful front facing experience belies a complicated, intricate series of systems, technologies, and considerations that we’ve never seen before.
  • Our customer references came back over-the-top positive on responsiveness, customer/ developer friendly, and intuitive/ easy to navigate user interface.

Ben and his team are introducing an entirely new way to think, access, and use money. I am excited to be joining Dwolla’s board of directors and look forward to helping Ben build the next multi-billion dollar payment company!

The personal computer is dead. As quickly as we moved from the desktop to the laptop, we are moving to the tablet — never to return. With the death of the PC, an entire ecosystem dies with it. The chipset is ARM based, rather than Intel. The operating system is all iOS and Android, rather than Windows. The applications are hosted cloud apps like Box, Google Apps, and Evernote rather than Sharepoint, Office and Outlook.

This is rocking the industry. Dell is being taken private — closing a curtain to start the dirty work of restructuring. HP, Microsoft, and Intel are all trading well off their peaks when the Dow has recently hit an all time high. IBM, looks like the sole winner, jettisoning its PC business years ago to China-based Lenovo. Well, it’s a good thing all of these companies also play a big part in the $55B* server market — that’s not going away anytime soon, right? The worst days are over and hopefully their collective market caps will recover? Not so fast…

Modern web services, such as Google, Apple and Facebook are pushing the limits of data center scaling to unprecedented levels as they deal with an exponential growth in user traffic. They are playing a massive game of Tetris as they grapple with deploying and operating data centers with tens of thousands of servers versus hundreds. They are all on the bleeding edge of trying to contain costs while cramming as much capacity into a physical building as possible. The result is a complete architectural rethink of datacenter designs and the incumbent server vendors are struggling to stay relevant in this new reality.

The new data center designs use only commodity “vanity free” components procured directly from the original design manufacturers (ODM) — the current incumbent’s suppliers. For easy serviceability, components are velcro’d together versus mounted in a box. All bells and whistles are stripped off and the hardware is purpose built for a specific application and therefore carefully tuned. As compute utilization rates skyrocket from virtualization and parallel processing, the CPUs are running harder and hotter and therefore the new expense bottleneck is all about power and cooling.

Take for instance, Facebook’s Open Compute initiative, which lays out a blueprint for an energy efficient hyper-scale datacenter that is 38 percent more energy efficient and 24 percent less expensive than current datacenters. Locating in cold climates and next to super-cheap hydro power has become de rigor. Power distribution, cooling and building layouts have been redesigned from the ground-up to maximize mechanical performance and electrical efficiency of the datacenter. And unfortunately for Intel, the relentless march of Moore’s Law no longer affords them differentiation, as customer needs have shifted from performance to power efficiency, an area where they lag rival ARM processors.

The evolution of the modern hyper-scale datacenter reflects the hyper-scale needs of the applications that run on them. Modern web 2.0 (and increasingly SaaS) applications need to handle thousands of user requests per second, processing terabytes of information in real-time across hundreds of customers. They are by necessity massively parallel and work in concert to service a user request. This is the modern equivalent of a giant supercomputer — except cobbled together from commodity server components and interconnect fabrics. It’s a profound software and hardware architectural shift that is taking us from a world where datacenters consisted of small number of independent high performance branded servers to a brave new world where the giant, datacenter building is the server.

Meanwhile on the enterprise front, the corporate datacenter is becoming increasingly sedate as on-prem applications give way to their SaaS counterparts.

The new data center architectures, borne of necessity from the giant web service providers, have the potential to massively drive down the cost of providing software as a service, the new winner in enterprise applications. As such, the cloud service providers (CSPs) such as Amazon and Rackspace, are adopting these “scale-out” architectures.

So fast forward: SaaS, will win the enterprise market. Face it — it’s just so much better and now, infinitely cheaper than any of the alternatives. And modern SaaS applications will be delivered through hyper-scale data centers that do not have branded servers from Dell, HP or IBM, but rather highly optimized, scale-out white box servers made by Asian ODMs. In addition, the operators of these massive data centers will be experts in servicing their creations — monitoring, fixing and rapidly swapping out their expected-to-fail components. Therefore, there will no longer be a need for the recurring revenue, high-margin service and maintenance contracts that have been a mainstay of the OEM server industry.

I wonder if Lenovo is in the market for a server business too?

: )

I would like to thank my partner, Ramu Arunachalam for his research, analysis, and material contributions to this blog.


*IDC estimates (2012)

It is now clear that App.net (ADN) is not just a for fee twitter clone but a full on platform for developers to build a whole new set of services on top of.

With the announcement and launch of a free tier, ADN is following in the footsteps of Evernote, Dropbox, and Github in providing a well-worn business model. And the media, including Fast Company, Forbes, Quartz, TechCrunch, the Verge, VentureBeat, plus many more – are taking notice.

According to Forbes, “Caldwell is part of a larger trend that is trying to apply the way developers think about the digital world to products that can be easily used by non-technical consumers. These attempts buck the more general trend in the app-o-verse of insulating users from any direct contact with their own data or any sense of how much control they could actually exert upon it, given the slightest effort.”

Exactly right. ADN gives developers the ability to build innovative products and solutions that users love and gives users the ability to choose which social experience is best for themselves.

One of my favorite quotes from the coverage is from the Quartz piece: “While Twitter is trying to provide the social-media equivalent of a fully fitted bathroom, App.net’s could best be described as just the plumbing.”

We couldn’t agree more. Some people like marble bathrooms with jeweled faucets and others like a bare bones outdoor shower, but both need running water. Just like plumbing, your social graph is an incredible tool and we support ADN’s vision to let developers design countless “bathrooms” and let users choose what works best for them.

TechCrunch points to the importance of timing in making a critical move like this. Dalton has been very thoughtful about the impact of freemium on the ADN community. And wanted to build out the broader developer ecosystem before attracting a broader audience. The invitation system is a prudent way to open the doors slowly.

I want to congratulate the ADN team for the work and preparation behind this freemium launch – the coverage has been uniformly positive and the users are responding!

We are excited about the possibilities of this new platform and can’t wait to see what the developer community builds using the power of this new model. Sign up here for instant access or get a hold of an invite to check out freemium!