Information technology companies constitute the core of many investment portfolios nowadays. With so many new startups popping up and some highly visible IPO’s and acquisitions by public companies egging things on, many investors are clamoring for a piece of the action and looking for new ways to rapidly qualify or disqualify an investment ; particularly so when it comes to hottest of hot investment areas – information security companies. 

Over the years I’ve found myself working with a number of private equity investment firms – helping them to review the technical merits and implications of products being brought to the market by new security startups. In most case’s it’s not until the B or C investment rounds that the money being sought by the fledgling company starts to get serious to the investors I know. If you’re going to be handing over money in the five to twenty million dollar range, you’re going to want to do your homework on both the company and the product opportunity. 

Over the last few years I’ve noted that a sizable number of private equity investment firms have built in to their portfolio review the kind of technical due diligence traditionally associated with the formal acquisition processes of Fortune-500 technology companies. It would seem to me that the $20,000 to $50,000 price tag for a quick-turnaround technical due diligence report is proving to be valuable investment in a somewhat larger investment strategy. 

When it comes to performing the technical due diligence on a startup (whether it’s a security or social media company for example), the process tends to require a mix of technical review and tapping past experiences if it’s to be useful, let alone actionable, to the potential investor. Here are some of the due diligence phases I recommend, and why:

1. 1. Vocabulary Distillation – For some peculiar reason new companies go out of their way to invent their own vocabulary as descriptors of their value proposition, or they go to great lengths to disguise the underlying processes of their technology with what can best be described as word-soup. For example, a “next-generation big-data derived heuristic determination engine” can more than adequately be summed up as “signature-based detection”. Apparently using the word “signature” in your technology description is frowned upon and the product management folks avoid the use the word (however applicable it may be). Distilling the word soup is a key component of being able to compare apples with apples.

1. 1. Overlapping Technology Review – Everyone wants to portray their technology as unique, ground-breaking, or next generation. Unfortunately, when it comes to the world of security, next year’s technology is almost certainly a progression of the last decade’s worth of invention. This isn’t necessarily bad, but it is important to determine the DNA and hereditary path of the “new” technology (and subcomponents of the product the start-up is bringing to market). Being able to filter through the word-soup of the first phase and determine whether the start-up’s approach duplicates functionality from IDS, AV, DLP, NAC, etc. is critical. I’ve found that many start-ups position their technology (i.e. advancements) against antiquated and idealized versions of these prior technologies. For example, simplifying desktop antivirus products down to signature engines – while neglecting things such as heuristic engines, local-host virtualized sandboxes, and dynamic cloud analysis.

1. 1. Code Language Review – It’s important to look at the languages that have been employed by the company in the development of their product. Popular rapid prototyping technologies like Ruby on Rails or Python are likely acceptable for back-end systems (as employed within a private cloud), but are potential deal killers to future acquirer companies that’ll want to integrate the technology with their own existing product portfolio (i.e. they’re not going to want to rewrite the product). Similarly, a C or C++ implementation may not offer the flexibility needed for rapid evolution or integration in to scalable public cloud platforms. Knowing which development technology has been used where and for what purpose can rapidly qualify or disqualify the strength of the company’s product management and engineering teams – and help orientate an investor on future acquisition or IPO paths.

1. 1. Security Code Review – Depending upon the size of the application and the due diligence period allowed, a partial code review can yield insight in to a number of increasingly critical areas – such as the stability and scalability of the code base (and consequently the maturity of the development processes and engineering team), the number and nature of vulnerabilities (i.e. security flaws that could derail the company publicly), and the effort required to integrate the product or proprietary technology with existing major platforms.

1. 1. Does it do what it says on the tin? – I hate to say it, but there’s a lot of snake oil being peddled nowadays. This is especially so for new enterprise protection technologies. In a nut-shell, this phase focuses on the claims being made by the marketing literature and product management teams, and tests both the viability and technical merits of each of them. Test harnesses are usually created to monitor how well the technology performs in the face of real threats – ranging from the samples provided by the companies user acceptance team (UAT) (i.e. the stuff they guarantee they can do), through to common hacking tools and tactics, and on to a skilled adversary with key domain knowledge.

1. Product Penetration Test – Conducting a detailed penetration test against the start-up’s technology, product, or service delivery platform is always thoroughly recommended. These tests tend to unveil important information about the lifecycle-maturity of the product and the potential exposure to negative media attention due to exploitable flaws. This is particularly important to consumer-focused products and services because they are the most likely to be uncovered and exposed by external security researchers and hackers, and any public exploitation can easily set-back the start-up a year or more in brand equity alone. For enterprise products (e.g. appliances and cloud services) the hacker threat is different; the focus should be more upon what vulnerabilities could be introduced in to the customers environment and how much effort would be required to re-engineer the product to meet security standards.

Obviously there’s a lot of variety in the technical capabilities of the various private equity investment firms (and private investors). Some have people capable of sifting through the marketing hype and can discern the actual intellectual property powering the start-ups technology – but many do not. Regardless, in working with these investment firms and performing the technical due diligence on their potential investments, I’ve yet to encounter a situation where they didn’t “win” in some way or other. A particular favorite of mine is when, following a code review and penetration test that unveiled numerous serious vulnerabilities, the private equity firm was still intent on investing with the start-up but was able use the report to negotiate much better buy-in terms with the existing investors – gaining a larger percentage of the start-up for the same amount.