It’s time for Philly’s premier emerging tech conference, and I’m going to be speaking once again this year. The conference, Emerging Technologies for the Enterprise, is taking place March 26-27, 2008 in Philadelphia.

I’ll be giving a more technical talk this year than last, combining my interests in leading-edge web applications and security. The talk is called Securing Web 2.0 Applications:

The challenges of securing first generation web applications and infrastructure seem like a distant memory: immature technologies throughout the stack, coded in a culture that didn’t understand or value security. Today we have a much more security-conscious community producing components from operating systems to routers to web servers, and the basic architecture of the Internet application has had 10 years to mature under fire.

Even so, the security challenges of Web 1.0 were in many ways less daunting and harder to ignore than those of the current generation. This talk will review the challenges and lessons of the past, and survey security requirements, issues and techniques for dealing with a new generation of web frameworks and tools, massively multi-tenant applications and hosting environments, and loosely-coupled systems.

When evaluating new ventures, a lot of energy goes into thinking about the risks involved. I’ve been breaking things down into two major categories, and trying to consider those relatively independently.

The first, execution risk, has been well covered - I especially like this old post from Martin Tobias. In a nutshell, execution risk covers the risk involved with successfully doing those things that are under the company’s direct control. I think many entrepreneurs have a tendency to underestimate execution risk in the same way that drivers who correctly understand the population’s risk of having an auto accident underestimate their personal risk, but that will have to wait for another post.

The second category is what I think of as ‘assumption risk,’ the risk that the world does not actually end up working the way the entrepreneur believes it does. Market risk is one type of assumption risk, but it is by no means the only one.

Since I focus on ventures with a big technology component, I’ve noticed that technical assumption risk is often misclassified as execution risk. This may be due in part to the problem of modeling complex systems - many of the systems we work on are sufficiently complex that it is not feasible to prove the validity of a solution without some measure of real world trial.

The misclassification may also be due in part to the roles in a startup; often, the people thinking about risk in a business planning context are different from those thinking about technical assumptions. When senior management is relatively non-technical, there are a couple of ways to deal with technical risk:

1. Think about all technical risk in terms of “the chance that our technical team will pull this off.” Essentially, this is an intentional classification of all technical risk as execution risk.
2. Work with the technical team to distinguish execution and assumption risks, and plan accordingly

It likely goes without saying that well-run startups choose the 2nd approach.

When we first started building the TurnTide product, we faced plenty of technical risk from both categories. There were a couple of primary assumption risks: how effectively would the application of our traffic shaping techniques to email streams control spam? would good email get through even from nodes that also sent spam?

No amount of modeling or analysis could tell us with absolute certainty what would happen in the real world. The only way to deal with these assumption was to get a beta product deployed in a large, real-world mail stream and test.

There were also execution risks from every direction: would we build a stable network appliance? would the traffic shaping implementation work as designed? would the analysis system accurately determine how much of the network resources to allocate to each sending node?

Execution risk is certainly quite different, in that we know from the outset that a correct solution is possible. We knew that we could do all of these things successfully; in order to mitigate our execution risk we needed to figure out how to maximize the chances that we would do so.

In a sense, the elimination of assumption risk could be considered the creation of value, in the same way that the discovery of mineral deposits would be. The elimination of execution risk, then, is the realization of value - analogous to the process of extracting and refining the buried minerals. Both are clearly necessary, but the require different investments and deliver different returns.

The process for technical startups is nowhere near as linear as I’ve just implied, but since the amount of risk is inversely related to the valuation of a startup company during its various rounds of funding, it seems to be well worth thinking about these issues when planning funding rounds and the progress made between them.

I’ve never gotten very into new year’s resolutions, but since I’m working on a few things and it happens to be December 31st, I’ll take my inspiration from Josh and call them “resolutions.”

1. Keep my home office organized

This one is tough for me… Ever since college I’ve used the “pile” method of filing, and can typically find anything I’m looking for within a few seconds (of course, the occasional item requires a search party). I’ve made the shift at work, and my desk at the office has been uncharacteristically tidy for a year now. Today, I managed to get the home office close - a little more time tomorrow and it will be in good shape. Keeping it that way, of course, is the resolution.

2. Adopt a new system for personal time management

I haven’t even read the book yet (its been on my shelf for a couple of years… how sad is that?), but at this point I need a better todo list tool, let alone time management tool, so it seems to be a good time to try out the GTD approach. I’m leaning toward OmniFocus, a new app from the company behind OmniOutliner and OmniGraffle. I’ve downloaded the pre-release version and will post my thoughts once I’ve used it for a while.

3. Blog more frequently

This one is obvious - I posted frequently for the first half of 2007, and then all but disappeared. I want to blog more, and my final resolution is to do so.

Happy New Year!

My friends at Invite Media are hosting Jeff Barr, Web Services Evangelist at Amazon.com, for an Amazon Web Services Evangelist Meetup on November 7th.

Its great to see Jeff coming to Philly for this; we have a small but vibrant and growing emerging tech and startup community here, and some people are already using S3, EC2 and the rest of AWS for new projects. For details on the meetup and to sign up, see the event page.

A few weeks ago at the Emerging Technologies Conference at MIT, Ann Winblad made the comment, “Finally, math is cool again.” The comment stayed with me, as math has been an important part of virtually everything I’ve worked on - from InfoSec Labs in the 90’s, translating mainframe-era security models into methodologies appropriate for companies taking their first steps online, to TurnTide a few years ago, restricting use of resources by spammers to break the economic model behind their theft and abuse.

There does seem to be a general upswing in the visibility of math in the commercial world, starting with the extension of the quant revolution in the finance markets to the optimization of a diverse set of industries. The rise in the popularity of poker, and the influx of new players, has led to some new popular interest in math as well - books like The Mathematics of Poker (which I recommend) were hard to imagine on bookstore shelves a few years ago, but have been remarkably successful.

In the world of technology-driven startups, which was the context for Ann’s comment, I draw an imaginary line between two applications of math:

• Creation of a fundamentally new product, business or market
• Optimization of an existing business

The latter of these applications is the one that is driving the quant revolution in finance, poker, and a thousand other areas. In the online world, some big ideas have already broken ground and fundamentally changed the way a number of markets work. The mechanics of business online and the rush to market, however, mean that a lot of the decades of quant optimization in the offline world has been left behind.

I’m pretty excited about the opportunities that come from taking inefficiencies out of businesses that operate at Internet scale, as well as recapturing some of the subtleties of the offline markets. Math is cool again, and some very cool new answers are being created to the age-old question asked of math teachers - “But when will I ever use this?”

Fred Wilson posted yesterday about overcounting web audiences, highlighting a study on the topic put out by comScore.

The goals of comScore’s research, of course, is to make the case for panel data in accurately measuring audience. Fred’s conclusion is more general:

You cannot rely on your own analytics data. You need third party data as well. That’s not to say that third party data (primarily panel data) is perfect either. You have to triangulate between all the numbers to get a decent view of what’s actually going on.

Undercounting conversions

All of that said, I titled this post “undervaluing web audiences” because I think there is an interesting flipside to the big “audience is overcounted by 2.5x” message of the study. If audiences are overcounted by this much, and those overcounts apply to ad impressions as well as overall unique visitor counts (according to the study, unique ad impressions were indeed part of the analysis), then there is likely some depression of conversion rates in many of the cookie-based analytics tools.

I’m sure that some simple conversion paths are exempt from this problems: a click on a search ad that results in a conversion during the same browser session is unlikely to suffer from any of the cookie-related issues outlined in the study. More complex paths, however, such as those based on brand impressions, repeated display ad impressions or deferred conversions, are likely to be undercounted by the same measure as the unique audience.

The behavioral ad networks are known for the application of their technology to targeting. Another key asset, however, is the ability to measure the value and ROI of online brand advertising. They use their networks, based largely on cookies, to track the deferred conversions that prove the value of a brand impression campaign.

If they are undercounting these conversions by 2.5x, perhaps current impressions are undervalued such that a correction for overcounting of audience would need to be somewhat offset by an adjustment to effective CPM for the brand ads run on the site. In any case, I’m sure advertisers doing brand impression campaigns, as well as the ad networks, will want to figure out how to more effectively measure deferred conversions if cookies present such significant accuracy problems. It sounds like Tacoda might be using comScore’s data to try to adjust.

There is a growing trend in consumer web applications in which one site will ask users for their usernames and passwords on other sites. Using these credentials, a site will log onto the other sites to carry out actions on behalf of, and hopefully with the informed consent of, the user.

‘On behalf of’ logins

LinkedIn and Plaxo are examples of sites doing this to import contact information. In fact, Plaxo makes this functionality available as a service to developers of other applications. Slide, RockYou, Photobucket and a bunch of other widget publishers do this to smooth the process of getting their widgets on users’ pages on MySpace, Bebo, Hi5 and the others. Also, some of the more interesting mashups involve data from the deep web, and require usernames/passwords to get it from 3rd party sites.

API-based authentication

Contrast the ‘on behalf of’ approach with that of Facebook, which exposes APIs providing for access by 3rd party applications, on behalf of users, through a direct authentication by the user to Facebook. As long as the APIs support the access required, this eliminates the need for the 3rd party to collect usernames and passwords.

The fact that MySpace and others don’t have API access (or complete enough APIs) to their sites is what has driven developers to collect credentials and act on behalf of users.

Some sites actually have APIs but don’t take advantage of the fact that they could use them to tighten up security. While Salesforce could use the Facebook-style authentication for 3rd party apps, they instead have those apps solicit and store user credentials (by policy, they allow only “certified” apps to do so).

Why are ‘on behalf of’ logins a problem?

If the 3rd party site is deserving of users’ trust, and everything works properly, there should be nothing wrong with these logins. We don’t worry much about local applications doing this type of thing: blog editors, web design programs, browsers and countless other local apps all store user credentials for 3rd party apps and sites. In fact, this type of login is enabling startups to drive innovation in the new social network ecosystem; if they had to wait for the MySpaces of the world to publish APIs or enable new functionality, these companies would be dead in the water.

In reality, there are some real problems to think about. In addition to a couple of shared issues, the key differences from local applications are also the problems here:

• Trust of the application and vendor - an issue with both web and local applications. The decentralized and volatile nature of web applications, and the lack of user-centric security infrastructure (such as local anti-virus and anti-malware software), make this a tough problem for web applications.
• Authorization of the specific actions that apps take on behalf of their users - an issue with both web and local applications; if this is done really well, the problem of trust of the app and vendor is diminished.
• Location of user credentials - in web applications, these credentials live ‘in the cloud’ somewhere. The vendor claims and reality of the security of those credentials are at best hard to verify.
• Scale - the barriers of installing, and updating, local software limit the scale of this problem in that world. Web applications are easy to sign up for and can be updated multiple times a day, leading to a lot of complexity in managing overall user security.

It looks like a solution probably starts with a way to give users centralized control and management of:

• Authentication credentials
• Authorization of ‘on behalf of’ logins
• Authorization of specific ‘on behalf of’ actions

What about OpenID?

OpenID is a framework for decentralized identity. It supports decentralized authentication and structured sharing of personal information.

‘Decentralized’ in OpenID terms means decentralized from the perspective of web applications; this can in fact mean centralized from the user’s perspective. OpenID could be used to do logins on behalf of users without the collection of credentials, but it does not address the problem of authorization of those ‘on behalf of’ actions. The structured sharing of personal information involves a narrow kind of authorization, but too limited to solve this problem.

The transparency of ‘on behalf of’ action is itself a pretty complex problem - it requires giving the user a way to see and understand what the 3rd party app will go and do for them on the other site. I’m not sure whether this is a problem OpenID is interested in tackling. If it develops momentum as an identity standard, it would certainly be nice to see it go beyond authentication and identity to a more complete view of security (something Microsoft’s virtually dead Passport initiative and the Liberty Alliance project both failed to do).

Here are the slides from my talk on the impact of the current generation of emerging technologies on the startup, given at the Emerging Technologies in the Enterprise conference in Philadelphia yesterday. The event wrapped up today; by all accounts it was the best value in web technology conferences in recent memory, and I look forward to attending next year.

I’d like to throw out an idea for discussion, especially as it applies to startups selling into the enterprise:

Small buyers of technology, acting early in the technology adoption life-cycle, are motivated by hope (hope == ROI, opportunity, etc). Large buyers of technology, acting late in the life-cycle, are motivated by fear (fear == risk of loss or punishment).

A good example of this can be found in the typical upgrade cycle. Early, individuals and small groups upgrade to new hardware, operating systems and applications because they hope that access to new features and capabilities will be more than worth the effort and disruption of the upgrade. Large groups don’t upgrade until much later, even if the benefits of doing so are dramatic; they often wait until the fear of loss of support from vendors forces a transition.

I remember experiencing this dichotomy in the major changes to the practice of information security as the commercial Internet grew in the mid 1990’s. Security shifted from an operational part of IT, where purchases were motivated by fear of loss rather than ROI, to a source of enabling technology for new ways of doing business. Within startups and large existing enterprise, small teams tried to figure out how to build online businesses. Along the way, they pushed the nascent Internet security product companies into building the right pieces to enable and protect the new ecommerce ventures.

Today, it seems like information security has largely returned to the operational state: anti-malware technology is a cost of doing business online, regulatory requirements drive new security spending, and fear of public outcry and regulatory enforcement prompts increased scrutiny on the handling of customer data.

It is likely that large organizations will miss much of the benefit of web 2.0 technologies as well, as they wait for incumbent software vendors to deliver later in the adoption cycle, when they will buy out of fear of being left behind by competitors. Most of the startup companies I see trying to sell innovative technologies into the enterprise today through the IT organization haven’t really figured this out.

A few companies, however, are dealing with this really well. Most are SaaS plays, and Salesforce is among the first of the good examples. Salesforce established small, dedicated groups of customers who bought the service with company credit cards rather than purchase orders, and used it without the authorization of central IT. Companies like 37 Signals, Zoho, ConceptShare, and countless others are using roughly the same model.

Going back to the idea of hope vs. fear in the acquisition of technology, I think there are a few things these startups could be doing differently to scale sales to big organizations.

Enterprise Freemium

The freemium pricing plans offered by the three startups I mentioned above are structured in a way that makes sense for small teams, but breaks for very large ones. They all offer some kind of free trial, and then price their services based on the amount of use (number of users, amount of storage, etc). Within a large company, this means that a small number of initial users can evaluate the product, and probably pay for ongoing use on a credit card, but growth becomes more difficult at that point. After the trial period, new users typically can’t be added without moving up to a pricing plan that supports them. The team footing the bill, however, is only willing and able to pay for its own use, not the much higher prices that come with larger plans.

I think there could be an enterprise twist on the freemium model, with the following characteristics:

• Free trial for each additional user within a company
• Easy options for billing/payment by user or group, rather than for the whole company
• Premium options for IT

The last of these, ‘Premium options for IT,’ is the most important. Knowing that IT won’t make early technology buys to support their users’ hopes for opportunity and improvement, the startup should support broad grassroots adoption of their products at lower levels. When the motivators that drive IT purchasing, such as fear of losing central control over data, backups, users, access control, and management complexity, kick in due to the grassroots use, the startup needs to be there to directly support IT with purchase options.

For a SaaS product, these IT premiums might be things like onsite, appliance-based offerings of:

• Directory services integration for user accounts
• Enterprise backup integration
• Data integration with reporting, dashboard, data warehouse and other systems

There are plenty of examples of enterprise IT banning the emerging technologies that come onto their radar when they don’t have a way to mitigate their fears. The best way I can think of for the startup to deal with this is not the traditional attempt to convince IT that their fears are unfounded, but rather giving IT a way to purchase that mitigation in the way they are used to and comfortable with.

This isn’t a big shift for most startups. The model still provides early revenue and a short sales process, but also offers a level of scale previously available only to those selling to a central organization. From a product perspective, this approach requires some thinking about the needs of IT and perhaps some new development; chances are that the thinking and planning will have benefits for internal SaaS operations if done early, and the development can be done at the right time to fit in with the adoption and growth of the product. If startups continue to deliver these innovative SaaS products with direct application in the enterprise, there may even be a Feedburner or Mashery model here: a company could focus on providing the IT premium layer for SaaS offerings.

I gave a talk today at the pre-conference CxO breakfast for the Emerging Technologies for the Enterprise conference. The group was great; so much discussion that we didn’t make it through all of the material I had planned.

As promised, here are the slides from today’s presentation. We talked so much about each point that I’m not sure how much value these have to folks who weren’t in the room… maybe we can get the organizers to do audio or video next time.

Each generational transition in IT, such as from mainframe to client server or from client server to web applications, has presented challenges to enterprise security. The pattern is clear, and will likely sound familiar to anyone working in IT through these last two major shifts:

1. The emerging technology is initially ignored as a lab project or toy.
2. As the technology is first applied to solve business problems, organizations often attempt to restrict or ban any meaningful use.
3. When the production status of systems or apps built on the new tech can no longer be ignored, security is typically enforced through controls on the legacy infrastructure, which are the systems of record for existing enterprise data used by the new apps.
4. Eventually the emerging technology matures, and adoption increases, to the point that its security role and context is understood and verified to the same level as legacy systems.

This pattern results in a series of enterprise security risks, and perhaps more unfortunately, a series of missed opportunities to improve protection and decrease cost with each generation of technical change in IT. I would love to see IT security getting involved with emerging technologies at stage 1 in the pattern above, thinking about how the new tech can be used in ways that improve security rather than threaten it. Attempts at banning emerging technology in stage 2 usually push the use under the radar, so that departmental systems exist outside of normal production boundaries, increasing the risks over sanctioned use. The first attempts at security controls in stage 3 discount the value of data that lives in the new systems, and leads developers of the new applications to create their own security models from scratch, or largely ignore security under the assumption that it is a legacy system problem. Finally, at stage 4, a massive task has built up. As formal security models are applied to the new systems and applications, large, costly changes have to be made that would have been almost free if thought about earlier.

There is a generational change happening today in the enterprise, and I think it is not too late to change the pattern. The technologies that are driving down the cost of starting Internet companies are having an impact in the enterprise as well: open source software such as Linux and MySQL, newer languages such as Python, Ruby, Erlang and PHP, frameworks such as Ruby on Rails, and other technologies like virtualization and outsourced web service infrastructure (EC2, S3, etc) are all enabling rapid, inexpensive development of production-capable apps by very small teams.

This generation of emerging technologies brings with it some wise principles: a core focus on testing, continuous integration, convention over configuration, and loose coupling via well-defined interfaces (among others). I think the opportunity presented here is a great one. If people who care about enterprise security get involved with these technologies and the communities behind them now, then security can be built into these frameworks in a way that makes it tough to build new applications that don’t do security well.

Using Ruby on Rails as as a simple example, if good security becomes the convention, it is built into every application and tested for at every stage. Simple investments in gem-based integration of enterprise security infrastructure such as single sign-on and role-based access control systems can create an environment where developers build and verify security by default. The enterprise can do this internally, and can also encourage or require outside vendors of security components to support emerging technologies much earlier than they do today.

This kind of investment is a big shift for most enterprise security organizations. It will require spending, managing and perhaps hiring a bit differently, but I believe the result is better security at a lower cost to both the security organization directly and to the enterprise in general.

I’m going to be speaking at a couple of related events in March. The Emerging Technologies for the Enterprise conference on the 28th and 29th in Philadelphia has an interesting array of topics, centered around open source, lightweight architectures and Web 2.0, all with an enterprise twist. On the first day, I’m giving a talk called Startup 2.0: Harnessing Emerging Technologies in the New Startup World:

Whether building a new company from scratch, or keeping a big company competitive, emerging technologies have changed the rules. Open source software, web services, mashups, AJAX, Ruby, Rails, and RSS… only a few of a seemingly endless list of technologies that have redefined what is possible for small teams. This talk will focus on startup experiences, lessons learned about technology choices and tradeoffs, and on building, funding and running a technology startup in the new environment.

The Emerging Technologies for the Enterprise folks are also putting on a pre-conference breakfast for CxO’s and executives on the 15th. I’ll be the keynote speaker for that event, talking about Tiger Team Innovation:

Startup companies use small teams beginning with a blank slate and the latest emerging technologies to build incredible value overnight. This talk will focus on using the same techniques, with a few twists, to deliver measurable value to the enterprise in new ways.

The main conference is open to everyone and seems to be quite reasonably priced compared to most such events; registration is here. I believe the breakfast is by invitation, so if you’d like to attend leave a comment or send me email and I’ll ask the organizers to include you.

The long tail of content presents an interesting set of problems both for publishers and advertisers. Content in the tail may be seen only a few times a day; if the publisher has a small amount on content in the tail (one blog, for example), that content is:

• Not valuable enough to the publisher to justify looking for advertisers or even signing up for a network
• Not valuable enough to advertisers or networks as inventory based on the low number of views

I think there are a number of things to talk about around advertising on the long tail, but I’m going to focus in this post on what happens when the tail wags. In other words, what happens when a chunk of content in the long, skinny part of the tail suddenly moves toward the fat part.

There are some interesting numbers in an analysis of the results of Digg and Reddit homepage hits for one long tail page. The author describes a site with less than 100 uniques per day growing to a total of 234,000 uniques over 5 days, and describes the process of adding AdSense ads to the site:

After being Dugg, our Adsense account was finally approved 36hrs later, and some adsense ads went on the front page. … Over the four days we used adsense, we made a total of 71.87 [dollars]. Our average click through rate was a dismal 0.24%, although the ads on our site seemed to be fairly highly targeted.

The first problem is the 36 hour delay in getting AdSense ads up on the site; this is a common issue with this type of content, as the ‘wag’ of the long tail content to high visibility can happen very quickly. I’m sure Google could optimize this somewhat, but the nature of long tail content is such that the publisher may not even know about the rush of traffic until days later. The only real solution is for the long tail content to somehow be enabled for advertising before the traffic comes.

The AdSense clickthrough rate of 0.24%, and thus the overall value to the publisher, is another problem: That site’s ad space was only worth a very low $0.70 on a CPM basis. This could be due to a lack of any historical data in AdSense to improve targeting, it could due to the differences in reader behavior for Digg/Reddit/etc referrals versus organic search referrals, or it could be something related to the specific content.

In all likelihood, there is an opportunity for publisher and ad network to get a lot more value from this content. Were Digg, for example, to create a new kind of ad network where signing up was just about as easy as putting a “Digg It” button on a page, they would have a good stab at signing up long tail publishers beforehand, and solving the problem that caused a 36 hour delay in monetization in the example above.

Digg, like similar sites, also has access to some great raw data about content. They know categorization, topics and tags, along with the momentum of individual content moving out of the long tail. Given an ad network, they would also be able to create multiple-impression campaigns across member sites, adding value for ad buyers. I’m betting the value of the space on each popular content page would be higher in the context of a common ad network across the Digg site and many of those linked pages. Consider the value to advertisers of being able to buy, in advance, ad space on the sites that will be on Digg’s front page in the future.

The real value may be the power of the social bookmarking sites’ community to, implicitly or explicitly, control the ads associated with each linked page. This could be as simple as doing what any smart ad network does, and showing the better performing ads more often on a given page. A more interesting approach might be to make the control explicit by giving users the ability to vote up or down the various ads associated with a page, or by showing how many previous users had clicked an ad.

I’m curious to see how directly the user generated content wave impacts advertising, and how sites like Digg evolve to increase the ad value of the long tail content that they rocket to prime time.

It has always been hard for the enterprise to address emerging information security issues proactively; usually these things end up dealt with by the majority of companies once a loss has hit close to home or regulatory attention has been brought to bear. I was lucky to be able to work with some very smart companies during the transition to the Internet-connected enterprise and ecommerce, as these companies recognized that dealing with new information security risks proactively enabled them to aggressively go after new revenue or cost savings.

I think this is the kind of thing that CIOs and CISOs will need to be thinking about as emerging technologies reshape the organizational and physical footprint of IT and add an order of magnitude more interconnections between applications and systems.

My good friend and long time co-conspirator Stephen Cobb recently asked what I thought were the emerging threats to enterprise security. There are a few threats that I’ve been giving some thought to lately that I haven’t seen addressed effectively; I’ll tackle one of these in this post and leave the others for later.

Security of Software as a Service

There is a lot of momentum behind the software as a service model; Salesforce.com is the poster child, but a big set of products that used to be delivered from inside the corporate datacenter are now bought as services and delivered from shared vendor resources outside. Some dismiss security concerns about SaaS as cynical, but I think there is a lot more to this story. The enterprise security issues can be broken down into a few sections:

Product security

The concerns about product security are much the same for SaaS as they are for traditional enterprise software purchases. Architecture, security features, and underlying implementation are all key factors in the overall security of the product.

There a couple of distinctions between the two that come into play: the evaluation of SaaS offerings is feature driven and does not typically include implementation detail, and the lack of an in-house integration phase (a key benefit of the SaaS approach) means that vendor claims are never put to the test in the way that happens during the real-world integration of software products in the enterprise.

Among the risk elements that come from these distinctions is the lack of visibility onto and control of scope of compromise and consequences of component failure. Essentially, without visibility onto implementation detail, and real-world verification of vendor claims, it is very difficult for the enterprise to understand the security impact of the failure of any part of the system.

Multi-tenancy

A set of security issues unfamiliar to the enterprise is introduced by a key component of the SaaS model: the hosting of multiple customers on shared infrastructure. Multi-tenancy takes a variety of forms:

• application level divisions between customers

The most basic form of multi-tenancy is implemented by SaaS vendors as an application construct. This means that the divisions between customers are unique to the application, and are not subject to outside scrutiny. A bug at the application level can result in a failure of separation, meaning that other customers or even the general public may have access to enterprise data.

This option requires custom development by SaaS vendors, typically provides for the most attractive customer density and scalability profiles, and presents the most difficult security challenges for the enterprise.

• logical separation between customers

Separation implemented below the application level relies on integration mechanics to keep the divisions between customers intact. For example, individual web server instances (running on shared hardware) mapped to different hostnames might provide a front-end separation. This can be continued through routing of requests to similarly configured middleware instances and database servers. Often some components will still be fully shared, such front-end load balancing / caching and back-end storage networks.

Since this option depends on features of 3rd party components, and implements multi-tenancy through integration and component configuration rather than software development, it is both easier to validate from a security perspective and involves less up-front cost to the SaaS vendor. Customer density and scalability, as well as complexity of new customer deployment, can be impacted.

Security issues can sometimes be severe in this case as well, when the failure of an infrastructure component threatens a key assumption about logical separation. Failure of VLAN separation due to a bug in Cisco’s switching software, for example, could compromise logical separation between customers if those protections are not implemented in a layered way.

• physical or pseudo-physical separation between customers

An extreme case of the integration-level separation described above is the use of virtual OS instances or physically separate systems to provide independent instances of applications and supporting infrastructure such as database servers. This case provides the most easily validated architectural security; as OS virtualization matures and server hardware is designed for these workloads, the scalability, density, and deployment cost/complexity challenges of physical separation will likely improve.

The security impact of multi-tenancy, along with core product security, comprise the directly technical part of the challenge for the enterprise.

Operations

The operational issues stemming from the use of SaaS are not particularly technical, but can be difficult to manage and control. At the heart of the issue is the fact that critical enterprise data must exist, for an extended time, on systems controlled by a third party.

• Direct Operational Issues

The employees of the SaaS vendor manage its systems; they have access, ultimately, to the data of their enterprise customers. While not unmanageable, the potential for access by employees not subject to direct monitoring and control by the enterprise presents a significant risk.

• Organizational Issues

Custody of enterprise data by a 3rd party presents some broader challenges as well. Since the 3rd party has access, they could faced with subpoenas or other challenges that might be handled differently by the enterprise directly. Business relationships, changes of control, or even acquisition of directly competitive customers can create real or perceived misalignments of interest.

Essentially, the law recognizes certain providers of business services, such as legal counsel or accounting services, as having a special or protected relationship with their clients. It remains to be seen how the law evolves to handle these new types of service provider whose access is no less sensitive.

SaaS isn’t going anywhere, but the fact that there haven’t been any front-page losses yet isn’t a reason to put off thinking about these security issues. I think that there are probably some opportunities for technical solutions to control some of this risk, and make the process of ensuring and validating security of SaaS deployments much more manageable for the enterprise.

In the mean time, I think an exploration of these issues by the enterprise in looking at SaaS deployments will lead to more sophisticated requirements and vendor selection, and better understanding and control of risk today.

When a company like Yahoo comes out with a cool new horse, it’s easy to get caught up in the technology and its potential, and forget about the product strategy differences between startups and big players.

Looking at the technically innovative startup pitches I’ve heard from this perspective, I can break them down into two basic categories.

Horse before the cart: we have built this really incredible technology. Here’s what it is and how it works. Take a look at our demo, which proves that we have built this technology. Here’s a list of amazing things we can do better with this new technology.

Cart before the horse: we are doing this amazing thing. it wasn’t possible before, and doing this thing enables an awesome new business. Take a look at our demo, which proves that are doing this amazing thing. It works because of this really incredible technology we have built.

Yahoo, and other big companies, can afford to occasionally build and launch a new horse without putting a clear, focused application of the technology out in front. In fact, doing so can help them maintain their influence and claim leadership in new areas. Some successful startup companies have built technology first without a narrow application guiding the business, but I’d argue that these are the exception rather than the rule.

From the founder perspective, I think that focusing on a technology, however cool, can lead to some problems. When the technology comes first in my thinking, I can fall into a trap of not diligently evaluating even one of the many potential market opportunities. Focusing on one little application of the cool new technology means thinking about things like who, exactly, will buy it… what will they pay for it… how will they use it… how will it change their lives. Cool technology is really exciting to a few people, but the thing it does is what makes it exciting to lots of people.

Looking at companies from the outside, as an investor or otherwise, I find the technology/application focus question to be even more important. Founders may have a grand vision for an eventual application of the technology, but if they are focused on building a business around a focused, narrow application first then they will make better decisions about how much money to raise, how much to build before launching, and how to measure success. The focus on an initial application makes business decisions, external and internal, quite a bit easier. It also turns the technology into a key asset and competitive advantage, rather than the company’s raison d’être.

Funding or starting this type of company means that the initial, focused application stands on its own as a business that should be built. If that business is successful, the company can leverage its technology assets in tackling larger opportunities.