Big Red Ventures Fund Manager: Achint Agarwal
Achint: You have had a unique career trajectory, moving from serial entrepreneurship and consulting to academic leadership, and finally to venture capital. What motivated these pivots, and how does that diverse background influence your approach to investing?
Jeremy: My path has certainly been a mix of ventures and “real jobs.” It started right after college when I launched a delivery company, and later, during business school, I started an internet music company. I actually raised money in my third semester and was nearly forced to drop out, but the Dean allowed me an unprecedented part-time status to keep the company going. After running that for about four years and moving through other ventures, including an email company and my own startup, Pricing Engine, which went through the ERA accelerator, I spent eight years operating before transitioning into academic leadership.
At Columbia Business School, I became the head of the entrepreneurship center, where I managed funds and built an angel syndicate specifically for the school ecosystem. That experience, combined with over years of teaching across Columbia, Cornell, and NYU, gave me a deep involvement in the ecosystem. My philosophy on the transition to venture capital is simple: early-stage investors with operating backgrounds are often superior to pure private equity professionals. A couple of guys from private equity aren’t necessarily going to understand what it takes to hire and fire or build a company from scratch. While academic constraints initially limited my ability to focus purely on returns, I realized I could be more effective “on the other side of the dotted line” while maintaining those academic relationships.
Achint: How does Textbook Ventures differentiate itself from other funds, particularly given its name and connection to the academic world?
Jeremy: Despite the name, Textbook Ventures is not student-run; it is a professional fund structure managed by myself and my partner. My partner brings a background in critical minerals and expertise from RAND, which complements my digital experience. Our differentiation is the network we have built over years. I often joke to Limited Partners that my competitors could go back in time years, start teaching, and build up the same network, but otherwise, it is really hard to beat.
We have evolved our investment focus beyond just current students to the broader alumni ecosystem. While current students are eager and excited, they don’t always have the right ideas yet. Our sweet spot is alumni who are two or three years out of school—people who have identified big problems during their early business journey. We particularly like serial entrepreneurs, especially second-time founders who have learned from previous attempts. A great example is a former student named Saint. I helped him get into the ERA accelerator, and after he built a successful company with investment from Microsoft and Amazon, he came back to me for advice on his second venture. Because of that long-term relationship, we invested, and we have already seen a 6x markup.
Achint: Is there a specific sectoral thesis at Textbook Ventures? You seem to invest in a wide range of industries.
Jeremy: We don’t have a specific sector thesis so much as a thesis on what we won’t do. We avoid deep-pocket requirements, such as heavy hardware or companies requiring FDA regulatory approval, unless there is already a lead pocket available. Despite my background as a digital marketing professor, we exclude pure marketing plays. I also have a personal bias against ed-tech due to the incredibly slow sales cycles in that industry.
Our strengths align with my experience: SaaS, subscription models, and freemium businesses. When we look at areas like climate or sustainability, our interest is driven by business fundamentals rather than ideology. Ultimately, technology buildability is no longer the main constraint—you can build almost anything you can describe these days. The critical question we ask is: does the economics, does the value exchange, make sense?
Achint: With the rapid rise of AI and other emerging technologies, what trends are you most focused on right now?
Jeremy: I view AI as a generational transformation opportunity; we haven’t even begun to see the full impact of it. However, the best implementations are those that solve specific workflow pain points. The successful approach is the tool that, for bucks a month, saves you so many hours that you can finally get your work done and go home. I see AI less as a complete disruption and more as a new tool for familiar SaaS models.
Regarding VR and AR, I think physics constraints—weight, battery life, and eye strain—remain limiting factors. It feels similar to the history of mobile adoption, where we kept saying “every year is the year of mobile” for a long time before it actually happened. We likely need a catalytic event, similar to how the pandemic drove Zoom adoption, or a critical innovation in pricing models to really open up that market.
Achint: For students and aspiring VCs, the industry can seem opaque. What are your thoughts on the reality of working in VC and the best career paths to enter the field?
Jeremy: The industry reality is challenging, because nobody knows if you are actually good at it for about eight years. For career paths, the traditional ladder of associate or analyst positions is scarce because the industry is so small. Those roles tend to be at large AUM firms and focus on later-stage deals, which feel more like private equity or finance roles.
I believe the successful operator route is often the best path. By building a network and helping friends, you eventually move into angel investing. However, the challenge is that startups pay poorly, which limits your capacity to angel invest unless you have had a successful exit. Starting your own fund is another option, but that requires connections and capital—often generational wealth. “Doors” are the hardest thing to open. My advice is to build experience that offers a unique perspective. For example, cross-border experience is massively useful; people in emerging markets like India view someone coming with US experience very positively.