The internship program is one of the pillars of Harlem Capital that we are most proud of. Over the years we have been lucky to work with more than 130 interns. Every one of them has left a mark on this firm, and they have gone on to do amazing things across the tech and investment landscape.

Once a month, we catch up with an alum of the Harlem Capital internship. This month, meet:

Name: Derek Oliver | Current Role: Investor, Vista Equity Partners

Why did you choose to apply to the Harlem Capital internship?
The mission. Harlem Capital was built around backing exceptional founders and investing in diverse communities, and I wanted to contribute to that impact. At the time, I was working in investment banking and looking to transition into investing. The internship offered an opportunity to develop a different skill set, moving beyond financial analysis to understanding how investors develop conviction, evaluate founders, and identify emerging opportunities.

How did the internship shape your career?
Harlem Capital was my first foray into investing. It was where I began transitioning from an advisor to a steward of capital and developing an investor’s mindset. The experience gave me exposure to technology companies at their earliest stages and helped shape how I evaluate business models, distinguish between products that solve essential problems versus those that are simply nice to have, and assess a company’s ability to remain relevant over time.

What are you doing now?
I work at Vista Equity Partners, a technology investment firm specializing in enterprise AI and software.

How are you using AI today?
I use AI as a personal learning and productivity tool. It helps me explore new ideas, pressure-test my thinking, and build familiarity with unfamiliar topics. I view AI as a complement to my own thinking, not a replacement for it. Ultimately, the judgment and conviction still have to be mine.

What advice do you have for aspiring investors?
First, develop a viewpoint. Build a perspective on which business models matter, what differentiates winning companies, and which businesses are positioned to succeed over the long term. Technical skills are table stakes. What differentiates great investors is their ability to identify trends, exercise sound judgment, and develop conviction in businesses with the potential to compound over time.
Second, invest in genuine, meaningful relationships. Relationships have always mattered, but as access to information becomes increasingly democratized, the ability to build authentic connections becomes even more valuable. Take the time to understand people, cultivate trust, and approach relationship-building with intention.
Finally, develop deep expertise in a specific domain. Particularly for those transitioning into investing, developing expertise in one or two sectors can provide a differentiated perspective, establish credibility, and give others a compelling reason to seek out your insights.

About Harlem Capital

Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome.

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