Introducing Cyber Portfolio Management

At RSA’17, I spoke on “Security Leadership Lessons from the Dark Side.”

Leading a security program is hard. Fortunately, we can learn a great deal from Sith lords, including Darth Vader and how he managed security strategy for the Empire. Managing a distributed portfolio is hard when rebel scum and Jedi knights interfere with your every move. But that doesn’t mean that you have to throw the CEO into a reactor core. “Better ways you will learn, mmmm?”

In the talk, I discussed how “security people are from Mars and business people are from Wheaton,” and how to overcome the communication challenges associated with that.

RSA has posted audio with slides, and you can take a listen at the link above. If you prefer the written word, I have a small ebook on Cyber Portfolio Management, a new paradigm for driving effective security programs. But I designed the talk to be the most entertaining intro to the subject.

Later this week, I’ll be sharing the first draft of that book with people who subscribe to my “Adam’s New Thing” mailing list. Adam’s New Thing is my announcement list for people who hate such things. I guarantee that you’ll get fewer than 13 messages a year.

Lastly, I want to acknowledge that at BSides San Francisco 2012, Kellman Meghu made the point that “they’re having a pretty good risk management discussion,” and that inspired the way I kicked off this talk.

A New Way to Tie Security to Business

A woman with a chart saying that's ok, i don't know what it means either

As security professionals, sometimes the advice we get is to think about the security controls we deploy as some mix of “cloud access security brokerage” and “user and entity behavioral analytics” and “next generation endpoint protection.” We’re also supposed to “hunt”, “comply,” and ensure people have had their “awareness” raised. Or perhaps they mean “training,” but how people are expected to act post-training is often maddeningly vague, or worse, unachievable. Frankly, I have trouble making sense of it, and that’s before I read about how your new innovative revolutionary disruptive approach is easy to deploy to ensure that APT can’t get into my network to cloud my vision.

I’m making a little bit of a joke, because otherwise it’s a bit painful to talk about.

Really, we communicate badly. It hurts our ability to drive change to protect our organizations.

A CEO once explained his view of cyber. He said “security folks always jump directly into details that just aren’t important to me. It’s as if I met a financial planner and he started babbling about a mutual fund’s beta before he understood what my family needed.” It stuck with me. Executives are generally smart people with a lot on their plates, and they want us, as security leaders, to make ourselves understood.

I’ve been heads down with a small team, building a new kind of risk management software. It’s designed to improve executive communication. Our first customers are excited and finding that it’s changing the way they engage with their management teams. Right now, we’re looking for a few more forward-looking organizations that want to improve their security, allocate their resources better and link what they’re doing to what the business needs.

If you’re a leader at such a company, please send me an email [first]@[last].org, leave a comment or reach out via linkedin.

Sneak peeks at my new startup at RSA

Confusion

Many executives have been trying to solve the problem of connecting security to the business, and we’re excited about what we’re building to serve this important and unmet need. If you present security with an image like the one above, we may be able to help.

My new startup is getting ready to show our product to friends at RSA. We’re building tools for enterprise leaders to manage their security portfolios. What does that mean? By analogy, if you talk to a financial advisor, they have tools to help you see your total financial picture: assets and debts. They’ll help you break out assets into long term (like a home) or liquid investments (like stocks and bonds) and then further contextualize each as part of your portfolio. There hasn’t been an easy way to model and manage a portfolio of control investments, and we’re building the first.

If you’re interested, we have a few slots remaining for meetings in our suite at RSA! Drop me a line at [first]@[last].org, in a comment or reach out over linkedin.

Sneak peeks at my new startup at RSA

Confusion

Many executives have been trying to solve the problem of connecting security to the business, and we’re excited about what we’re building to serve this important and unmet need. If you present security with an image like the one above, we may be able to help.

My new startup is getting ready to show our product to friends at RSA. We’re building tools for enterprise leaders to manage their security portfolios. What does that mean? By analogy, if you talk to a financial advisor, they have tools to help you see your total financial picture: assets and debts. They’ll help you break out assets into long term (like a home) or liquid investments (like stocks and bonds) and then further contextualize each as part of your portfolio. There hasn’t been an easy way to model and manage a portfolio of control investments, and we’re building the first.

If you’re interested, we have a few slots remaining for meetings in our suite at RSA! Drop me a line at [first]@[last].org, in a comment or reach out over linkedin.

Open Letters to Security Vendors

John Masserini has a set of “open letters to security vendors” on Security Current.

Everyone involved in product or sales at a security startup should read them. John provides insight into what it’s like to be pitched by too many startups, and provides a level of transparency that’s sadly hard to find. Personally, I learned a great deal about what happens when you’re pitched while I was at a large company, and I can vouch for the realities he puts forth. The sooner you understand those realities and incorporate them into your thinking, the more successful we’ll all be.

After meeting with dozens of startups at Black Hat a few weeks ago, I’ve realized that the vast majority of the leaders of these new companies struggle to articulate the value their solutions bring to the enterprise.

Why does John’s advice make us all more successful? Because each organization that follows it moves towards a more efficient state, for themselves and for the folks who they’re pitching.

Getting more efficient means you waste less time per prospect. When you focus on qualified leads who care about the problem you’re working on, you get more sales per unit of time. What’s more, by not wasting the time of those who won’t buy, you free up their time for talking to those who might have something to provide them. (One banker I know said “I could hire someone full-time to reject startup pitches.” Think about what that means for your sales cycle for a moment.)

Go read “An Open Letter to Security Vendors” along with part 2 (why sales takes longer) and part 3 (the technology challenges most startups ignore).

Adam's new startup

A conversation with an old friend reminded me that there may be folks who follow this blog, but not the New School blog.

Over there, I’ve posted “Improving Security Effectiveness” about leaving Microsoft to work on my new company:

For the last few months, I’ve been working full time and talking with colleagues about a new way for security executives to measure the effectiveness of security programs. In very important ways, the ideas are new and non-obvious, and at the same time, they’re an evolution of the ideas that Andrew and I wrote about in the New School book that inspired this blog.

and about a job opening, “Seeking a technical leader for my new company:”

We have a new way to measure security effectiveness, and want someone who’ll drive to delivering the technology to customers, while building a great place for developers to ship and deploy important technology. We are very early in the building of the company. The right person will understand such a “green field” represents both opportunity and that we’ll have to build infrastructure as we grow.

This person might be a CTO, they might be a Chief Architect. They are certainly an experienced leader with strong references from peers, management and reports.

Seeking a technical leader for my new company

We have a new way to measure security effectiveness, and want someone who’ll drive to delivering the technology to customers, while building a great place for developers to ship and deploy important technology. We are very early in the building of the company. The right person will understand such a “green field” represents both opportunity and that we’ll have to build infrastructure as we grow.

This person might be a CTO, they might be a Chief Architect. They are certainly an experienced leader with strong references from peers, management and reports.

Lead on:

  • Product development & delivery including service, platform, statistics
  • Technology platform decisions (full stack from OS to UI frameworks)
  • Product quality including security & reliability
  • Technology process & culture which values effective collaboration
  • Tech hiring aligned with budget

Qualifications:

  • Early startup leadership experience (must have early experience, for example one of the first 50 employees)
  • Shipped at least one product from concept stage (must)
  • Big data/data science product/service experience (must)
  • Outstanding communication skills – both technical and interpersonal (must)
  • Gets hands dirty
  • UI & Design thinking (should)
  • Seattle location is ideal

We’re an equal opportunity employer, and welcome applicants from diverse backgrounds, except rock stars. We want great folks with humility, empathy and a desire to learn and grow as they help our customers measure security.

If you’re interested, please get in touch with me at first@last.org.

Threat Modeling At a Startup

I’ve been threat modeling for a long time, and at Microsoft, had the lovely opportunity to put some rigor into not only threat modeling, but into threat modeling in a consistent, predictable, repeatable way. Because I did that work at Microsoft, sometimes people question how it would work for a startup, and I want to address that from having done it. I’ve done threat modeling for startups like Zero Knowledge (some of the output is in the Freedom security whitepaper), and while a consultant or advisor, for other startups who decided against the open kimono approach.

Those threat modeling sessions have taken anywhere from a few hours to a few days, and the same techniques that we developed to make threat modeling more effective can be used to make it more efficient. One key aspect is to realize that what security folks call threat modeling is comprised of several related tasks, and each of them can be done in different ways. Even more important, only one of the steps is purely focused on threats.

I’ve seen a four-question framework work at all sorts of organization. The four questions are: “what are we building/deploying,” “what could go wrong”, “what are we going to do about it” and “did we do an acceptable job at this?”

The “what are we building” question is about creating a shared model of the system. This can be done on a napkin or a whiteboard, or for a large complex system which has grown organically, can involve people working for months. In each case, there’s value beyond security. Your code is cleaner, more consistent, more maintainable, and sometimes even faster when everyone agrees on what’s running where. Discussing trust boundaries can be quick and easy, and understanding them can lead to better marshaling and fewer remote calls. Of course, if your code is spaghetti and no one’s ever bothered to whiteboard it, this step can involve a lot of discussion and debate, because it will lead to refactoring. Maybe you can launch without that refactoring, maybe it’s important to do it now. It can be hard to tell if no one knows how your system is put together.

Understanding “what could go wrong” can happen in as little as an hour for people new to security using the Elevation of Privilege game. You should go breadth-first here, getting an understanding of where the threats might cluster, and if you need to dig deeper.

What are you going to do about it? You’re going to track issues as bugs. (Startups should not spend energy thinking about bugs and flaws as two separate things with their own databases.) If your bugs are post-its, that’s great. If you’re using a database, fine. Just track the issues. Some of them will get turned into tests. If you’re using Test-Driven Development, threat modeling is a great way to help you think about security testing and where it needs to focus. (If you’re not using TDD, it’s still a great way to focus your security testing.)

Total time spent for a startup can be as low as a few hours, especially if you’ve been thinking about software architecture and boundaries along the way. I’ve never spent more than a few days on threat modeling with a small company, and never heard it called a poor use of time. Of course, it’s easy to say that each thing that someone wants a startup to do “only takes a little time,” but all those things can add up to a substantial distraction from the core product. However, a media blow-up or a Federal investigation can also distract you, and distract you for a lot longer. A few hours of threat modeling can help you avoid the sorts of problems that distracted Twitter or Snapchat. The landscape continues to change rapidly post-Snowden, and threat modeling is the fastest way to consider what security investments a startup should be making.

[Update, Feb 5: David Cowan has a complimentary document, “Security for Startups in 10 Steps. He provides context and background on Techcrunch.]

Lessons from Facebook's Stock Slide

So as Facebook continues to trade at a little over half of their market capitalization of 3 months ago, I think we can learn a few very interesting things. My goal here is not to pick on Facebook, but rather to see what we can take away and perhaps apply elsewhere. I think there are three key lessons that we can take away:

  • The Privacy Invasion Gnomes are Wrong
  • Intent Beats Identity
  • Maximizing your IPO returns may be a short term strategy

Let me start with the “Privacy Invasion Gonmes.” The short form of their strategy is:

  1. Gather lots of data on people
  2. ???
  3. Profit

This is, of course, a refinement of the original Gnome Strategy. But what Facebook shows us is:

The Privacy Invasion Gnomes are Wrong

Gathering lots of data on people is a popular business strategy. It underlies a lot of the advertising that powers breathless reporting on the latest philosophical treatise by Kim Kardashian or Paris Hilton.

But what Facebook shows us is that just gathering data on people is actually insufficient as a business strategy, because knowing that someone is a a Democrat or Republican just isn’t that valuable. It’s hard to capitalize on knowing that a user is Catholic or Mormon or Sikh. There’s a limit to how much money you make being able to identify gays who are still in the closet.

All of which means that the security industry’s love affair with “identity” is overblown. In fact, I’m going to argue that intent beats identity every time you can get it, and you can get it if you…keep your eye on the ball.

Intent beats Identity

The idea that if you know someone, you can sell them what they need is a powerful and intuitive one. We all love the place where everyone knows your name. The hope that you can translate it into an algorithm to make it scale is an easy hope to develop.

But many of the businesses that are raking in money hand-over foot on the internet aren’t doing that. Rather, they’re focused on what you want right now. Google is all about that search box. And they turn your intent, as revealed by your search, into ads that are relevant.

Sure, there’s some history now, but fundamentally, there’s a set of searches (like “asbestos” and “car insurance”) that are like kittens thrown to rabid wolves. And each of those wolves will pay to get you an ad. Similarly, Amazon may or may not care who you are when they get you to buy things. Your search is about as direct a statement of intent as it gets.

Let me put it another way:
Internet company revunue per user

The graph is from Seeking Alpha’s post, “Facebook: This Is The Bet You Are Making.”

So let me point out that two of these companies, Facebook and LinkedIn, have great, self-reinforcing identity models. Both use social pressure to drive self-representation on the site to match self-representation in various social situations. That’s pretty close to the definition of identity. (In any event, it’s a lot closer than anyone who talks about “identity issuance” can get.) And both make about 1/9th of what Google does on intent.

Generally in security, we use identification because it’s easier than intent, but what counts is intent. If a fraudster is logging into Alice’s account, and not moving money, security doesn’t notice or care (leaving privacy aside). If Alice’s husband Bob logs in as Alice, that’s a failure of identity. Security may or may not care. If things are all lovey-dovey, it may be fine, but if Bob is planning a divorce, or paying off his mistress, then it’s a problem. Intent beats identity.

Maximizing your IPO returns may be a short term strategy

The final lesson is from Don Dodge, “How Facebook maximized the IPO proceeds, but botched the process.” His argument is a lot stronger than the finger-pointing in “The Man Behind Facebook’s I.P.O. Debacle“. I don’t have a lot to add to Don’s point, which he makes in detail, so you should go read his piece. The very short form is that by pricing as high as they did, they made money (oodles of it) on the IPO, and that was a pretty short-term strategy.

Now, if Facebook found a good way to get intent-centered, and started making money on that, botching the IPO process would matter a lot less. But that’s not what they’re doing. The latest silliness is using your mobile number and email to help merchants stalk find you on the site. That program represents a triumph of identity thinking over intent thinking. People give their mobile numbers to Facebook to help secure their account. Facebook then violates that intent to use the data for marketing.

So, I think that’s what we can learn from the Facebook stock slide. There may well be other lessons in an event this big, and I’d love to hear your thoughts on what they might be.

Calyx and the Market for Privacy

So there’s a new startup in town, The Calyx Institute, which is raising money to create a privacy-protecting ISP and phone company. I think that’s cool, and have kicked in a little cash, and I wanted to offer up some perspective on the market for privacy, having tried to do this before.

From 1999 until 2002, I was Director of Technology and Most Evil Genius at Zero-Knowledge Systems, a Montreal-based startup devoted to delivering privacy-enhanced internet services. Zero-Knowledge raised approximately $71 million dollars to deliver internet privacy, and then had to pivot its business model (before pivoting was trendy). Because management pivoted and found value in what we had built, it didn’t deliver on the privacy dream, but the company did make good money for shareholders.

It’s my hope that Calyx can deliver more privacy to more people over a longer time, and make money for shareholders as it does so. To do that, they’ll need to move from the excitement accompanying their announcements to delivering products in the market. So let me turn to:

The market for privacy
There’s a lot of excitement. Nearly a thousand people have donated cash. They’ve put together a nice advisory board. That’s because people care about privacy. A lot of folks claim that there’s no market for privacy (pointing to things like Zero-Knowledge), but I believe that they’re wrong. There is a market, and it’s hard to tap into.

One of the key reasons it’s hard to tap into the market is because privacy means different things to different people. It means so many things that there’s a good book on “Understanding Privacy.” (My review.) So, does privacy mean the same thing to consumers as it will to Calyx? Resisting demands from 193 national intelligence services is great, but what about protecting me from advertisers? The disjointed things people mean by privacy make it challenging to ensure that you line up with people’s concerns.

Another issue is that privacy is rarely a thing sold in and of itself. Privacy is an aspect of some service, either by providing a privacy-protecting version of the service, or privacy protection against the service. A privacy-protecting ISP has to offer me ISP service equivalent to what I get today, or some bundle that makes sense for me. For example, I pay extra because Speakeasy didn’t demand my SSN, and had technically competent people answering the support phones. They’re less awesome since Megapath bought them, but they’re not Comcast, and they’re not running for most infuriating company in the country. Tor is an example of privacy protection against your ISP. You have to get the whole bundle right, which is likely going to be harder than getting the bundle right without privacy. Of course, sometimes it’s easier. By billing my credit card, Speakeasy doesn’t need to collect my SSN, doesn’t need to protect it, and doesn’t need to pay for a credit check. (They do have to pay a monthly cut to the credit card company, but Comcast probably also pays that for most of their customers.)

That said, consumers do care about privacy, and do spend money on it when they can understand the threat and defense. It requires entrepreneurs and hackers willing to experiment. and eventually someone’s going to make a boatload of money doing so.

For more in-depth comments on this, see my home page, especially the end of 2002 and the start of 2003.

With that, let me turn to some questions about…

What Calyx is doing
Let me start with two quotes, which is the sum of my knowledge:

This project’s goal is to raise funds for my nonprofit organization, Calyx Institute, which will launch a privacy-focused Internet Service Provider and mobile phone service using end-to-end encryption technology.

and

Through other partnerships, we are poised to offer Internet service in 70 markets in the US using wireless spectrum which we will bundle with end-to-end encrypted Virtual Private Network (VPN) technology in order to keep the customer’s data as private as possible. The next products on the roadmap include hosted email and cloud storage/sync systems that utilize public key cryptography so that only the user possesses the key required to decrypt their email or files. This means that the provider (Calyx) will not be able to read your email or files even if it wanted to. And if Calyx can’t read it, it can’t be targeted by unconstitutional surveillance tactics. (Both quotes from “The Calyx Institute fundraising page“)

So running a privacy-preserving ISP is great. And again, I want what I have to say to be heard in the context that I’ve given them money to help them get going.

My first questions are around the ISP part of the business. Is this an ISP in the form of “I can buy a DSL line from them?” (or otherwise, get internet service directly?) If it’s a partnership, how are we protected from the partner? Encryption is all well and good, but if I don’t have cover traffic, then my use or non-use of the service gives out information. Someone at the entry node (say the partner) who choses to collaborate with someone who can watch the exit node (say the NSA, or the FSB/KGB) can figure things out over time. This issue is fundamental to all low-latency internet-based privacy systems, including the Freedom Network that Zero-Knowledge operated, Tor, etc. The fix is approximately sufficient and continuous cover traffic that exceeds the bandwidth in use.

The second comment, which derives from that is “if Calyx can’t read it, it can’t be targeted by … surveillance tactics.” That is simply untrue. An observer which can see more can apply more clever analysis. I’m willing to forgive this as an aspirational statement today, but it’s important for privacy providers to ensure that they don’t over-promise.

My next question is why New York? Because the founder is there? The NYPD has done some bad things in the civil liberties camp, including for example surveillance of mosques without cause, kettling and rounding up protesters and bystanders without cause during the 2004 Republican Convention. Does New York have the most favorable laws in the US for this sort of thing?

When we get to the phone company idea, I’m in favor of the idea, but operating a nation-wide mobile phone service is expensive. If you don’t do so yourself, you can operate a “Mobile Virtual Network Operator.” But if Calyx does so, then the network operator from whom it leases bandwidth can see IMEI numbers and otherwise fingerprint phones. There are some interesting challenges here, and we need to know more to understand what Calyx can deliver.

In conclusion
There is a market for privacy, and there is a market for private internet services. Calyx has an opportunity to tap into such a market, but it’s tricky and complicated to do so successfully. There are a lot of hard questions to be addressed along the way. However, it’s important to remember that privacy is an important and cherished value for excellent reasons. Calyx is unlikely to be either perfect, or as bad as the main players in today’s market. So they deserve your support, your attention, and perhaps even your money. Why not go donate?