Q&A with Rey Kirton: From College Safety to Safeguarding Data and DevOps through Investing

Reynaldo “Rey” Kirton is a Senior Associate at Forgepoint Capital. Learn more about his background here.

Rey, you’ve had quite the journey so far, with so many personal achievements already in your career. Please share your story and how that has made you who you are today.
My background is grounded in sports (I was an athlete from age five through college). Growing up in South Florida, I naturally gravitated toward football. I was recruited and played all four years at Harvard, where I was a part of two Ivy League championship teams. Through sports, I learned invaluable lessons about teamwork, leadership, perseverance, and discipline.

It wasn’t until after college that I applied what I learned from sports to my career. I started when I signed up for the CFA, which forced me to teach myself corporate finance and accounting concepts (which were a foreign language to me at the time). While I leaned on the CFA to learn financial concepts, I completed “Training the Street” and “Wallstreet Prep” courses to learn how to apply these concepts to practical applications. Years of self-taught courses helped me develop a cadence for utilizing mornings and weekends that I continue to leverage to this day.

Getting my MBA at Wharton made me more proactive and taught me how to multi-task. I attended business school with the sole purpose of breaking into Venture Capital and dedicated all my efforts to achieving that goal. I took a pre-MBA through first semester internship at a growth equity firm that invested in Food and Beverage, I interned at Harlem Capital, a VC firm that invests in women and minority owned businesses, I TA’d for Venture Capital finance courses, and I was a team lead for the Venture Foragers Club for which I pitched a cybersecurity thesis to a handful of VC firms in the Bay Area (this was my first introduction to Forgepoint Capital). In a nutshell, through my achievements I learned how to grind and put in the extra work to achieve my goals.

What inspired you to pursue a career in venture capital? How about your interest in cybersecurity?
Candidly, after undergrad I didn’t know anything about investing: my undergraduate internships were in the non-profit space. However, I was always curious about investing, and I thought it could be a good fit since I enjoyed research and working with numbers. This led me to take a job at Cambridge Associates, an investment portfolio management firm, which gave me much needed high-level exposure to the investment world. My primary job function was to evaluate investment funds, but I soon realized I wanted to work directly with portfolio companies instead. This led me to accept a job with Altman Vilandrie & Company, a strategy consulting firm now known as Altman Solon that focuses on Technology, Media, and Telecom, where I performed operational and market due diligence for private equity clients.

I enjoyed the work in consulting, but I always had the itch to transition to the buy-side: in consulting, I was only exposed to a small portion of the investment process, and I wanted full visibility into the entire process, including thesis generation, sourcing, and post-investment support. This experience also helped me realize that I enjoyed working with smaller companies, narrowing my investment interest to early stage B2B tech.

As for my interest in cybersecurity – that started while I was in consulting. I worked on a few transactions in the cybersecurity space and I thought they were fascinating. The topic area for the cybersecurity thesis that I pitched while in business school was actually “the future of mobility,” but I pushed for a cybersecurity angle because I thought that was the most interesting and relevant application.

It has been gratifying to build on this interest here at Forgepoint. I love our mission of “protecting the digital future” and how we’re building such a strong community and ecosystem for innovation in cybersecurity – it’s unique. In a rapidly digitizing world, data becomes increasingly difficult to protect, and it’s awesome to work with companies that are on the front lines of the cybersecurity battle. With my background working for non-profits as an undergrad and as a co-founder of a social enterprise, it’s an added bonus to continue the mission-oriented nature of this line of work.

Speaking of that social enterprise, you’re also an entrepreneur yourself! What is Pack Elephant and how has your experience building it influenced your perspective?
Yes! I also work with my sister on a startup called Pack Elephant, a values-driven corporate gifting platform dedicated to funneling corporate gifting spend into underrepresented communities that reflect the values of the gifter and the giftee. I’ve worn the hat of Chief Strategy Officer, Chief Financial Officer, and Chief Operating Officer while experiencing the ups and downs of bootstrapping a company from the ground up. Co-founding a company, especially as a first-time entrepreneur, is a lonely and taxing experience. I liken the experience to a football game: there are so many small wins and losses, but you can never get too high or too low because you’re still in the first quarter.

This experience has also given me the unique opportunity to see the startup fundraising process from the other side of the table, and I enjoy advising on a company that’s outside the general purview of my usual investment focus, especially for a social enterprise. It’s been a great learning experience and has given me even more empathy and respect for entrepreneurs.

Sounds like it. Shifting gears back to investing: which cyber and technology focus areas are you especially passionate about now and why?
At Forgepoint, we don’t see cybersecurity as a niche vertical within enterprise software, but instead we see cybersecurity as horizontal and foundational to all software development. With that in mind, I’ve always had a passion for data and analytics, so I’m most passionate about companies that facilitate the secure use of data in software applications (e.g. data observability, AI / ML, and DevSecOps).

So what do you do here at Forgepoint?
At Forgepoint my responsibilities can generally be split into three buckets: sourcing and market mapping, deal execution, and supporting portfolio companies.

Sourcing broadly encompasses building market maps that are representative of how we view the world, developing investment theses, identifying interesting companies, and meeting the leaders of those companies to understand their vision, mission, solution, and strategy, and how we might partner.

Deal execution is the market and operational diligence process that includes product deep dives, customer calls, financial returns analysis, etc.

Supporting portfolio companies involves working with the executive teams at our portcos to provide whatever support they may need. In my role, this typically includes financial projections and financial analysis for fundraising considerations. Our team also provides customer introductions, product and business strategy, operational and go-to-market guidance, and supports talent and hiring – basically however we can help our companies grow.

My time spent on each bucket can vary drastically week to week, but on average this tends to fall within a 40% sourcing, 40% deal execution, 20% portfolio support split.

That’s great that you can apply your background and training across these areas, with such depth and breadth. What’s the most rewarding aspect of what you do?
The most rewarding aspect of my job is building companies – not only the startups Forgepoint invests in, but also the entities we incubate like SolCyber, the modern MSSP which emerged from stealth last August. We currently have two Entrepreneurs in Residence starting new companies that will bring powerful new approaches to their respective areas. I have been working closely with one of the companies that will launch soon – I can’t name it publicly but let’s just say it has been very rewarding to collaborate with the CEO and see the progress of the firm so far.

From a personal development standpoint, serving as a board observer for two of our portfolio companies (Symmetry Systems, which offers robust data security for hybrid cloud environments, and the incubated company I just mentioned that’s in stealth) has also been rewarding. Forgepoint has a dedicated interest in mentoring and coaching team members to become value-add investors and board members, and I’m very excited to get some board experience under my belt!

What skills are necessary to succeed at what you do now?
From a competency standpoint, any VC firm will expect its associates to have a solid grounding in financial modeling and analysis and attention to detail – those skillsets are table stakes. I think what sets you up for success is being curious, passionate, and proactive – that you bring real insight while delivering on each deal and supporting your stakeholders during every step of the process, pre and post investment. You have to genuinely enjoy learning new things while being entrepreneurial in finding ways to add value. The hustle is real – on this side of the table too.

What advice would you give to someone interested in becoming a VC?

First, develop thoughtful, informed opinions about investable market areas. This is a great way to demonstrate that you can think like an investor.

Second, build your network. Venture Capital recruiting is opportunistic, and you never know when you’ll come across an opportunity.

If you weren’t an investor, identifying, backing, and helping incredible founders and teams, what would you be doing?
Realistically, I’d probably be consulting, advising early-stage companies, or working with Pack Elephant full time. Alternatively, I’ve always wanted to go to culinary school and then travel the world mastering different cooking techniques…

Ha! A chef as well, what a Renaissance man. Now you must share: what’s your favorite dish – that you’ve eaten or made?
The first thing that comes to mind is a dish called “Rundown” – it’s red snapper in a coconut-based cream sauce served over rice. The first time I had it was at a restaurant in Panama for a family reunion and I absolutely loved it. When I got back to the US, I spent weeks trying to recreate the recipe – I got pretty close too.

Recently I’ve gotten more into BBQing – I just bought myself a smoker for Christmas. Hopefully I’ll become a pit master one of these days.

Thank you for reading. Have a question for Rey? Get in touch: rkirton@forgepointcap.com.