How Andrew got into investing
My journey to venture capital has been non-linear, but each phase developed a distinct component of my investment approach. Beginning as a CPA and transitioning to institutional finance at a hedge fund provided me with a fundamental understanding of capital structures and market dynamics. This experience catalyzed my interest in investment theory, leading me to Columbia for my MBA.
Post-business school, I refined my analytical toolkit in investment banking, focusing on financial services and fintech. However, I found myself drawn to more substantive involvement with companies, which led me to co-found a fintech startup leveraging machine learning for alternative credit underwriting. This entrepreneurial experience revealed both the technical challenges and broader economic realities of building businesses in regulated environments. After selling the loan portfolio, I was drawn back to investing—this time with a deeper appreciation for the operator's vantage point.
Managing a $2 billion private markets portfolio at GCM Grosvenor exposed me to patterns that distinguish exceptional investment firms from merely competent ones. Evaluating managers across private equity, real estate, infrastructure, and venture capital, I developed a framework for sustainable competitive advantage within investment platforms themselves.
My transition to Mithril Capital allowed me to work directly with Peter Thiel and Ajay Royan, fundamentally reshaping my investment philosophy toward deep tech, healthcare, and enterprise software. Rather than relying on pattern recognition alone, I learned to evaluate opportunities through first-principles reasoning—asking not just whether something works, but why it works, and whether technological moats are genuinely defensible. This approach continues to inform my work at Alumni Ventures, where I maintain focus on differentiated teams building novel technologies with compounding advantages.
On the draw of differentiated investment models
What drew me to both Mithril and Alumni Ventures was their distinct positioning within a crowded market. In venture capital, differentiation often reduces to numerical comparisons, but Alumni Ventures has cultivated a unique narrative centered on democratizing access to venture capital for individual investors.
Starting with a single alumni fund for the Dartmouth community, AV has methodically expanded to over two dozen alumni funds serving more than 11,000 retail investors. This structure creates something fundamentally different in the venture ecosystem: a deeply engaged network of investors who, while focused on financial returns, maintain professional interests across sectors like AI, healthcare, and beyond. These investors aren't passive allocators—they are active participants who remain engaged with developments that directly impact their careers and industries.
At Alumni, we systematically leverage this network through our CEO services platform, which connects our investors with founders in substantive ways. Whether a portfolio company needs specialized technical talent, access to enterprise decision-makers, or strategic guidance in new markets, our network provides resources beyond capital. This network-powered approach, combined with our growing founder community and the professional connections of our investors, creates a compounding advantage that strengthens over time. This model represents a structural differentiation that attracted me to Alumni—there's intrinsic value in cultivating these connections that extends beyond typical venture capital parameters.
Experience, naïveté, and the ideal founder
The data regarding founder "patterns" is less deterministic than many believe. At Alumni, we support founders from diverse backgrounds, including those without connections to our representative schools. I've backed founders who departed from traditional educational paths, recognizing that credentials are not automatic indicators of success or failure.
One factor that does correlate with improved outcomes is founding experience. Having been a founder myself, I understand the value of navigating early mistakes and applying those lessons to subsequent ventures. The compounded knowledge gained from previous attempts enables entrepreneurs to anticipate challenges and allocate their focus more effectively. From an investment perspective, this experiential knowledge represents meaningful risk mitigation.
“I've been a founder myself, and I've made my share of mistakes. The true value of that experience lies in learning to avoid those mistakes the second time around, allowing you to navigate the next round of challenges more effectively. From a VC perspective, that kind of hindsight is invaluable.”
That said, many first-time founders achieve remarkable success—particularly when addressing problems they've experienced firsthand. I'm particularly drawn to founders with authentic connections to the problems they're solving. The most compelling origin stories often begin with someone determined to prevent others from experiencing difficulties they themselves encountered.
Interestingly, I also value the constructive naïveté that sometimes accompanies first-time founders. This quality—the willingness to challenge established assumptions or pursue ambitious goals without being constrained by conventional wisdom—can drive transformative innovation. As founders gain experience, they often develop greater awareness of potential failure modes, which can inadvertently limit vision. In venture investing, finding the optimal equilibrium between experience, naïveté, ambition, and resilience often defines the most successful founder relationships.
The pitfalls of market over-correction: balancing risk and vision
The current market recalibration is largely beneficial, but excessive correction in venture capital risks constraining the opportunity set. When investors become overly focused on metrics like capital efficiency, revenue traction, and near-term unit economics, they may overlook companies with genuinely disruptive potential. These companies might not satisfy every criterion on a risk-mitigation checklist, but they represent the kind of world-changing possibilities that emerge when investors back fundamental technological shifts amid uncertainty. While today's market is appropriately responding to the valuation excesses of 2021, rigid adherence to these parameters can inadvertently diminish the bold ambition that has historically driven category-defining companies.
Risk minimization can also narrow the aperture of what's considered possible. When investors become anchored to predetermined signals—insisting that a company must demonstrate specific revenue thresholds because historical analysis suggests correlation with success—they may miss more ambitious objectives that make a company truly exceptional. Venture capital at its best isn't merely about incremental improvements; it's about backing companies attempting to solve seemingly intractable problems. Especially at the early stage, one must maintain sufficient intellectual flexibility to ask: How might this technology fundamentally reshape its domain? This requires imagining potential futures and accepting the inherent uncertainty of betting on them. When investors without experience across market cycles overcorrect to minimize apparent risk, they may fail to recognize opportunities that could define their portfolios and markets for decades.
AI is a tool, not the solution
Artificial intelligence represents a powerful enabling technology that can unlock new dimensions of productivity and insight, but it should not eclipse the core problem being addressed. At Alumni, we leverage AI's capacity to analyze and synthesize information from platforms like Harmonic, enabling us to identify investment opportunities with greater precision and separate signal from noise—that's the substantive value. Similar to blockchain technology, AI's implementation is most effective when it becomes invisible; end users should benefit from enhanced capabilities without needing to understand the underlying mechanisms. If your product or service can be articulated without reference to AI, you're likely focusing on the fundamental value proposition rather than the technological means of delivery. The technology should serve the solution, not define it.
“AI should be invisible; I should just benefit from better product experiences and the tech itself should be obfuscated. If you can describe your product without mentioning AI, then you're really getting to the heart of what you're solving and the value you're delivering.”
The term "internet companies" has largely disappeared from our lexicon because internet connectivity now underpins virtually every business. A similar evolution will occur with AI in the coming years. The organizations that most effectively integrate these capabilities—focusing on solving substantive problems rather than merely implementing new technology—will establish sustainable advantages. While AI represents a generational shift in technological capability, its ultimate value derives from how effectively it addresses meaningful human and business challenges.
The business I would start
The most effective founders typically address problems they've personally encountered, and my career path has provided perspective across nearly every function within investment firms—from fund accounting and operations to investor relations and direct investing. If I were building a company today, I would focus on addressing one of the fundamental inefficiencies in private markets: the fragmentation of information and workflow systems that impede transparency and liquidity.
Having experienced these challenges directly—including instances where I observed the same portfolio company being valued inconsistently across different funds—I recognize the friction these inefficiencies create for all market participants. My hypothetical venture would develop infrastructure that increases transparency and facilitates more efficient transactions by leveraging AI to generate novel datasets and analytics.
By making private market data more accessible and interconnected, such a platform could serve limited partners, general partners, and intermediaries alike—ultimately creating a more functional ecosystem. The opportunity to build connectivity across these traditionally siloed domains represents a compelling investment thesis and would address persistent structural challenges I've observed throughout my career.
