By: Kelly White, Founder and CEO, RiskRecon
If you are starting a cybersecurity company, you will be very fortunate if you win the seed investment from Deepak Jeevankumar of Dell Technologies Capital. Two reasons. First, Deepak is a Founding Investor in every sense. Second, Deepak built RiskRecon by building its CEO. For a CISO turned entrepreneur that means everything. I don’t know if he does that for every company, but he did that for RiskRecon, and it made all the difference.
Deepak is a Founder Investor. I don’t say this lightly. Being a company founder is the most challenging and most rewarding role in any company’s history.
Being a founder means you were there at the start – the day a very small group of people came together and decided to build something big out of essentially nothing. Deepak does that. Like all founders, he doesn’t make the decision lightly. He is constantly engaging with CISOs, security engineers, and entrepreneurs in their offices, at conferences, and meetups to understand what they are thinking about. He asks questions and listens. He thinks about it. He studies it. Deepak has already developed the investment thesis before he sees a pitch deck. He’s looking to put the pieces together to make it happen.
Deepak has guts. At the time I pitched to Deepak and his General Catalyst partners there were two well-established cybersecurity rating providers. Deepak knew there was room for a third player in the space. He also knew that there was a better approach to cybersecurity ratings. He saw that in RiskRecon. Deepak put his neck out to make the investment – he staked his reputation on it. Founders do that.
Deepak was committed to RiskRecon. I never doubted it. We rode through some tough times together.
Raising our Series A was not easy. Though we had performed well during our Seed stage, we still had two headwinds. The VC world was still not convinced there was room for a third cybersecurity ratings company. And we were raising our funding during the 2016 elections – Hillary Clinton vs Donald Trump. The VC markets were locked up, waiting to see what the world would look like at the end of November. During that time, Deepak moved over to Dell Technology Capital. After the election, we got calls back from VCs we had pitched to. Closed. Deepak had already led the round with all Seed investors doing their pro rata.
The standard line you’ll get from VCs is “we are very helpful.” Deepak was beyond helpful. He was like having an employee that flexed across sales, marketing, human resources, and strategy. Deepak takes on very few investments because, when he invests, he invests his time. On the first day of investing in RiskRecon, Deepak drove me around the Bay to meet up with half a dozen CISOs. It is where our first customers came from. And he kept at it. His help wasn’t just about introductions. He was constructively engaged with the team, getting to know the people and providing them support. He did this when we were a five-person company and he did it when we were a 70 person company. It mattered. Employees of startups have to deal with a lot of uncertainty; investor perspective and encouragement on a personal level makes a big difference. Deepak did that.
I met up with Deepak for tacos during the 2020 RSA conference. Of course, we had already sold RiskRecon to Mastercard (which has been fantastic). The whole lunch, Deepak was pitching me on becoming a customer of one of his companies. I laughed and smiled because Deepak did that for RiskRecon and it was fun to be on the other side seeing him do it for one of his other companies.
Deepak built RiskRecon by building its CEO – me. Four years ago I was a very technical CISO. I was great at network and application security penetration testing. I knew how to architect a network and harden a system. I knew how to protect a complex enterprise, but I had no clue about how to build a business. MAL? MQL? SQL…what’s that? The makeup of an executive team? Nope.
Deepak knew what he was getting in to. He had a CISO with a good industry reputation and a passion to build RiskRecon. It was enough. Shortly after company founding, I met Deepak in San Francisco and he helped me through the initial stages of how to build the company. The first employee I should hire. Then we discussed the second and third. He guided me through thinking about where we needed to build to in six months – high-level milestones across people, product, and go-to-market. He helped seed these by making introductions to companies that would become my first customers. He helped me with recruiting.
He kept doing this. Not in any way that was intrusive or that made me feel like I wasn’t doing my job. He did it in a helpful way. He did it in a way that enabled me to grow into a CEO through experience – through my successes and my mistakes. And so it went, through the different stages of the company. Through our first customer on to our 100th customer and beyond.
The most aggressive Deepak got was around pipeline building. It just took me a long time to get the marketing thing. Too long. Despite the boards' concern about pipeline development, I under-invested in that area. We were doing so well on a thin pipeline, I didn’t pay too much attention to it. Finally, Deepak cornered me and said, very quietly mind you, “Kelly, I am using my loud voice now. You have to get a good marketing head and invest in building pipeline.”
Sometimes Deepak just propped me up. Being a CEO will lay bare all of your strengths and weaknesses. It will also wear you out. Revenue uncertainty, closing deals, people challenges, filling gaps that always exist, raising money, winning customer renewals – the stress can grind you down. And, unlike every other person in the company, the CEO has nowhere to turn. No boss to vent to. No ability to just walk away from something that has to be done. It stops with the CEO.
Deepak propped me up in some pretty dark times. It didn’t happen often, but I did vent to him. He heard my fears. He heard my frustrations. He listened. He didn’t hold it against me.
I reflect quite often on the advice Deepak quietly gave me during the building of RiskRecon. I wish I would have listened more closely. But hey, we did it. And Deepak played a big role in RiskRecon’s success. I am forever grateful to Deepak.