Derek, My AI Co-Pilot: A VC Intern’s Perspective
Alex Dong is currently pursuing his MD at Harvard Medical School. I was happy to learn that he is also interested in earning an MBA simultaneously. So, in the summer of 2025, he spent some time interning with us (Golden Section VC) at our Houston office. We enjoyed his presence along with two other brilliant interns, Aidan Lei of the University of Washington and Jameson Cronin of Texas A&M.
Below is the essay written by Alex Dong
Meet Derek —
Derek isn’t your typical AI chatbot. Yes, Derek can do everything your regular chatbot can do—help you write emails, find restaurant recommendations, and such—but Derek is more like a high-powered employee than a generic assistant.
Short for “Deep Extraction & Reasoning Engine for Knowledge,” Derek was designed to be a data-driven partner built specifically for the needs of venture capital, private equity, and their portfolio companies. Its goal: to revolutionize the way investment analysts, general partners, and business leaders interact with data.
The eSapiens Platform
Derek is part of eSapiens, an advanced language intelligence platform engineered to support end-to-end human-AI collaboration. Born out of Golden Section VC’s experience as an active investor in B2B SaaS companies, eSapiens was designed to address the lack of large language model (LLM) deployment in specific business environments where challenges such as domain-specific requirements, tool integration limitations, latency constraints, and interpretability issues remain.
The eSapiens team realized that it was incredibly difficult to gain real-time operational insights from a company’s portfolio. Financial reports and investor decks often reflected lagging indicators—or worse, aspirational storytelling disconnected from actual performance. Meanwhile, they floated on oceans of rich, underutilized data within their SaaS applications.
Thus, the eSapiens platform focuses on two complementary capabilities: a Text-to-SQL module that translates natural language questions into executable queries using structured databases, and a Retrieval-Augmented Generation module for finding and synthesizing information from lengthy documents and spreadsheets. Derek is part of this second module to extract, analyze, and interpret raw information with speed, accuracy, and clarity.
Both capabilities are easy to access, seamlessly integrated into the eSapiens user interface, and adaptable based on its conversational memory. eSapiens is thus a unified, multi-tenant platform that can support plug-and-play integration into real-world enterprise workflows.
Derek Use Case: Generating an Investment Deal Memo
Let’s dive into an example of how Derek can empower users to make smarter, faster, and more informed decisions by providing instant access to financial insights. An investment deal memo is a comprehensive evaluation of an investment opportunity widely used in venture capital and private equity to assess opportunities as objectively as possible. It helps guide investment committee decision-making, communicate with various stakeholders, and document the due diligence performed. However, due to the level of detail an investment memo requires—including a significant amount of information gathered from the founder as well as independent research—preparing and writing an investment deal memo is a laborious process that can take weeks to complete.
Enter Derek, again. Derek’s “brain,” or knowledge base, can take in a wide variety of documents, such as founder pitch decks, balance sheets, profit & loss statements, cap tables, cash flow forecasts, legal contracts, and more. Once you simply upload all relevant files for a specific company into Derek’s brain, he parses these files and understands their structure to retrieve relevant data and generate insights quickly on demand. This deep document analysis would otherwise take several days or even weeks for an individual employee to perform.
Next, upload a template document for your investment deal memo into Derek’s brain. Each firm may have a slightly different structure that they prefer, but the bottom line is that this template document doesn’t have to be written in a technical manner or follow specific prompt engineering guidelines. Rather, it can be written in plain English, with bullet points for what to include in each section. It’s as easy as uploading to Derek a Word document template that you would otherwise provide your investment analysts.
Finally, simply ask Derek to generate an investment deal memo based on the given template and all the company information that you’ve uploaded. You may have to iterate a few times and tweak your template or question for Derek to show exactly what you want, but it does so very quickly—within a mere minute or two.
I created a Derek specific to one of Golden Section’s portfolio companies by using the steps outlined above, uploaded 39 company-specific documents and one template, et voilà! The 15-page investment memo draft that Derek generated was structured, professional, and up to the firm’s standards. The deal memo included all key sections, such as company overview, management team, financial performance, market size and scope, competitor landscape, growth projections, deal structure, company valuation, risks, potential return on investment, recommendations, and much more.
Derek isn’t just performing simple data retrieval—he excels at interpreting numbers. Derek can calculate key financial metrics (e.g., gross margin, EBITDA, runway), compare performance across periods or between competitors, and identify trends, anomalies, and growth opportunities, to name a few. For instance, if you ask more specifically for a company’s monthly burn rate, Derek will locate the appropriate files, perform the calculations, and present the results in a clear, concise format while citing its sources.
You only need to double-check the deal memo and add to missing parts when indicated, since Derek is specifically designed to never invent or fabricate data. If information is not available, Derek will clearly communicate this message to the user, who can then go back and upload the required information or fill in the gap themselves. Derek’s output can then be edited, exported, and shared with your team or external organizations in a fast, streamlined manner.
While Derek is a powerful tool, its two main limitations are data scope and qualitative nuance. For the former, Derek’s insights are limited to the documents and data provided in his knowledge base. As such, he cannot access real-time market data or external sources unless explicitly integrated. Secondly, while Derek is built for quantitative analysis, he may not fully capture qualitative nuances, such as management quality or market sentiment, unless these are documented in his uploaded documents.
An Intern’s Perspective
Derek bridges the gap between raw unstructured data and actionable intelligence, making financial analysis accessible to experts and newcomers alike.
As an intern at Golden Section, I have personally learned a lot from Derek—specifically because he shows his work for his calculations, cites his sources so I can see what parts of each lengthy document or spreadsheet are most relevant to finding key data in my future work, and can explain financial jargon while modeling how to present and phrase certain insights. I have ultimately been much more independent and productive since I have both a teacher and a worker at my fingertips.
For more seasoned professionals, this automated data extraction, interpretation, and presentation frees up your time to focus on higher-value tasks, like strategic decision-making and relationship building. As you and your team only get busier, Derek will ensure that every decision is grounded in accurate, timely, and actionable information.
Looking Ahead
The capabilities of Derek—and eSapiens as a whole—extend far beyond generating investment deal memos and accelerating financial due diligence. A colleague recently used Derek to generate ‘tough questions’ for a second meeting with a founder team based on notes uploaded from their first conversation. The eSapiens platform is already being used for portfolio management—tracking the health and performance of multiple companies in real time—and for providing data-driven updates for board meetings. Other current use cases include scenario modeling for the impact of different business decisions using historical data, contract analysis, and even a visual dashboard dubbed ‘Immersive MAX’ that shows key financial metrics with real-time graphs that are updated every 24 hours.
This use case offers only a taste of Derek’s capabilities. Whether you’re evaluating a startup’s performance, preparing an investment memo, or seeking to uncover hidden trends in a company’s financials, Derek is here to streamline the process— turning raw operational data into real-time intelligence that empowers both investors and operators. Not to mention, as far as understanding plain English and being available 24/7 goes, Derek will be one of your highest-functioning employees.
By Alex Dong
July 11, 2025
