Reshaping the Future of Cybersecurity Start-ups

Jay Leek, Managing Partner & Co-founder of SYN Ventures

Jay Leek, Managing Partner & Co-founder of SYN Ventures

I spent most of my career as a cybersecurity practitioner. In the late 1990s, I worked for Check Point Software Technologies before joining Netrex Internet Solutions, which was acquired by ISS. After that, I was with Nokia for ten years, the last four of which I was globally responsible for Corporate IT Security for the organization, and then I went on to be the first International Security Officer for Equifax, when it was the only U.S. credit bureau that had not previously experienced a major security issue back in 2010. Then I became the first Chief Information Security Officer (CISO) in private equity, where I worked for Blackstone. In addition to having normal CISO responsibilities for the firm, and I also oversaw off-balance-sheet cybersecurity investments at Blackstone and worked with private equity on cybersecurity leveraged buyouts.  In 2017, I co-founded my first fund, ClearSky Security. We raised over $300 million in that fund, made 32 investments in security startups, and have had 14 exits thus far, making the fund a huge success.

In 2021, I co-founded my second fund, SYN Ventures, along with Patrick Heim, who was part of the founding team with me at ClearSky Security. We raised $200 million last year in SYN Ventures Fund I, and we will raise another $300 million for SYN Ventures Fund II in Q2 ‘22. Over the past five years, we have been one of the most active cybersecurity investors in the world, and I am also proud to say that we have had the 22 exits in that same period. So we are not just about making investments in early-stage startup companies but also about realizing returns for our investors and finding good long-term homes for our portfolio companies and their customers.

Backing Great Teams and Helping Them Succeed

We are extremely active in every company that we invest. Patrick and I are among the few former Fortune 500 CISOs who have turned full-time venture investor, and this is what really differentiates us. As former operators, we bought over half a billion dollars of security technologies over our 18 to 20-year careers, and we have a lot of experience, successes, scar tissue, and lessons learned as a result. This experience allows us to help our companies avoid making some mistakes and help then unlock opportunities and drive revenue through our relationships.

When making an investment, it all boils down to 'what are the attributes of a good company, and we think about the three T's — Team, Total Addressable Market (TAM), and Technology. We believe Team is number one by far in our investment thesis, where TAM and technology are interchangeable for two or three, but they all must be there. When a great team runs into challenges, it can fail, iterate, fail, pivot, iterate and ultimately succeed. On the other hand, when a team does not know what to do and hits a wall, they end up just burning venture dollars trying to figure out what to do, and this is a terrible situation for everyone involved.

Powering Disruptive Security Technologies

Our investors often ask us what category of security we are looking to invest in, and they expect us to say endpoint, networking, cloud security or something like that, but we do not think about an investment that way. Instead, we are investing in companies that are helping to address the number one problem in cybersecurity for the past decade — the talent gap. There is a massive lack of security professionals versus the demand to be able to tackle the global needs of cybersecurity and it is not getting any better anytime soon. So we are looking to invest in disruptive security technologies that help address this people challenge, which leads you to focusing on areas like prevention, automation, consolidated mini-platforms and companies that can drive other operational efficiencies. Additionally, we are focused on investing in transformational companies that cause people to go back and rethink how to solve problems completely different ways. This is all part of our aim to help CISOs transform their security programs in disruptive and more efficient ways.

Partnering with Founders and Creating Differentiated Value

We partner closely with our founders and CEOs, and the primary reason for our successful is because we do what we say we are going to do and consistently deliver.  This has allowed us to have 22 exits. Through those exits, over 300 people became millionaires for the first time, and we have been able to create over 4000 new jobs from the time we invested to the present day or exit. We have been fortunate enough to touch a lot of people's lives through our investments, and we have been able to be part of creating some very valuable companies and help many companies make fewer mistakes. Ultimately, we want to help drive the most favorable outcomes for all our companies.

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