There is a common assumption in venture capital that the path in, follows a fairly predictable sequence: earn the MBA, build experience at a bank or consultancy, and work your way into a seat at a fund. For many, that sequence has worked well. But a growing number of investors are finding that the most valuable thing they bring to an investment committee is not the credential itself, but the distinctive lens they developed long before they entered venture.
I recently spoke with Drew Gonzales, Principal at Side Door Ventures, about how professional background and domain knowledge shape the way investors evaluate opportunities and build portfolios.
Drew spent two years at Silicon Valley Bank and 2.5 years at Carta, where he performed 409A valuations for early-stage, venture-backed companies. He then transitioned to the investing side, spending 18 months at Manhattan Venture Partners before joining Side Door Ventures, where he has been full-time for the last three years.
He had a perspective on career development in VC that was quite interesting because it centers on a deceptively simple idea: the experiences that differentiate you from other investors are often the same experiences that allow you to identify what others cannot.
Domain Expertise as a Foundation for Conviction
One of the recurring themes in our conversation was the role of domain expertise in venture investing. Drew distinguished between familiarity with a sector and the deeper, accumulated understanding that comes from years of professional experience within it.
Emphasizing that professional background functions are far more than a credential. It can shape the lens through which an investor evaluates deals. Someone who spent a decade in aerospace, for instance, will recognize patterns or specific information in a deep tech pitch that a generalist may not have the context to assess, or be able to evaluate different industries with a unique perspective when applied to that particular context.
The instinct for many aspiring VCs is to position themselves as generalists, capable of evaluating opportunities across sectors. There is logic to that approach, particularly early in a career. But in the reality of deploying capital effectively, of building a portfolio with a coherent narrative and strategy, it can require conviction.
Conviction, in turn, tends to emerge from depth of knowledge rather than breadth. The investors who can distinguish between a genuinely differentiated technical approach and an incremental improvement are often the ones with firsthand experience in that domain. And again, it’s not just about experience but that rather you get a different lens or perspective when you view things from a knowledge point.
Side Door Ventures reflects this principle in its team members, all with their diversity of experiences, opinions and investing patters. The lean on each other to fill in gaps, bring diverse deal flow, networks and unique perspectives. The fund invests across software, life sciences, space, deep tech, blockchain, gaming, and more. Each partner contributes a specific vantage point that expands the team's ability to access and evaluate founders working at the edges of their respective fields.
Drew's view is that a team with genuinely different areas of expertise is better positioned to find unique founders and unique opportunities, precisely because each investor sees a different slice of the market.
Leveraging What You Already Know
How should aspiring investors think about the credentials and experience they accumulate on the way into a venture? An MBA, for example, is useful for building familiarity with deal evaluation, financial modeling, and the procedural lifecycle of how GPs meet LPs and how capital gets deployed. These are important competencies. And can be considered tools for positioning, that can be for a different approach rather than for perspective building that helps round out the type of investor you become.
Formal training matters, of couse, but perhaps a more distintic ability needed to emphasize is that of leveraging the professional world you come from, whatever that world happens to be, and specifically the worldview that came from it.
Bradley Tusk offers an instructive case. Tusk built Tusk Venture Partners by applying deep expertise in political strategy and regulatory affairs to the startup ecosystem. His work helping Uber navigate regulatory challenges against entrenched incumbent interests demonstrated that understanding the intersection of policy and technology could be a genuine investment thesis, not just an advisory service. Corporate affairs, government relations, and regulatory navigation became his domain, and he built a practice around it that few other investors could credibly replicate.
The principle at work is straightforward: Building your positioning in venture capital can come from expertise that is difficult to imitate because of the uniqueness of having built it yourself.
Formal credentials open doors, knowledge and perspective that set you apart as an investor tend to come from your unique experiences.
Continuous Growth as a Professional Imperative
Drew was candid about something that deserves more discussion in venture career development: this is not an industry that rewards complacency. The investment landscape evolves quickly, and the skills and relationships that made an investor effective five years ago may not carry the same weight today.
He highlighted that growth should be a priority. He emphasized a principle that resonates throughout the industry: venture is a space that requires constant curiosity to learn new things. The venture landscape shifts too quickly and being intellectually curious maintains you on the moving ground.
This connects to something I explored in a previous piece on finding your fit. The strongest candidates for venture roles, and the investors who sustain long careers in the industry, tend to demonstrate continuous learning and intellectual curiosity. They refine their thesis over time, seek out new areas of competence, and remain open to perspectives that challenge their existing frameworks.
At Side Door Ventures, this orientation toward growth shows up in the daily work of portfolio management. It is not simply about making initial investments. It is the ongoing discipline of supporting founders through introductions, providing substantive help where it is needed, and continuously sharpening how the team evaluates valuations and market dynamics.
Drew reflected on how his prior work performing 409A valuations at Carta gave him a foundational skillset for valuing early-stage companies—learning to speak the language of founders and evaluate cap tables from the lens of a VC—and how the day-to-day responsibilities of an investor, from due diligence to sourcing to portfolio support, constitute a craft that requires constant refinement.
What Side Door Represents
The name Side Door Ventures carries an implicit thesis about how the venture capital industry is evolving. It does not suggest an inferior point of entry. It suggests an alternative one, grounded in the recognition that the conventional pathway into venture, while valuable, is not the only route that produces strong investors.
The fund was founded in 2020 and has grown to a team that manages multiple fund structures, including two Seed Funds and two Opportunity Funds, as well as a Digital Asset Fund focused on web3 and blockchain technologies. They have made +150 investments to date.
They care about investing in audacious founders building technologies at the fringe. And usually we like backing founders that have the advantage of some sort of R&D or technical moat. AI has created a lower barrier to entry for software. So we're leaning in more on deep tech or hard tech, which usually requires deep, technical skillsets that are hard to replicate.
This aligns with patterns I observe regularly through GoingVC. The professionals who build the most durable careers in venture tend not to be the ones who followed the most conventional trajectory. They are the ones who identified where their specific expertise addressed a genuine gap and who had the persistence to develop that position over time.
Practical Takeaways
For those working to build a career in venture capital, or for current investors reflecting on how to develop their practice, Drew's perspective suggests several considerations.
First, conduct an honest assessment of your areas of genuine expertise. Not the sectors you have researched, but the domains where you have accumulated real professional depth. That depth is what allows you to evaluate opportunities with the kind of conviction that generalist knowledge typically does not provide.
Second, treat credentials and networks as tools rather than endpoints. An MBA, a prestigious employer, a strong professional network: these are means of positioning. They create access. But the perspective you bring to an investment committee, the insight that makes your evaluation of a deal different from anyone else's, needs to be rooted in something more substantive.
Third, commit to ongoing development. The venture capital industry does not reward static skill sets. Each year brings new technologies, new market dynamics, and new founders with different backgrounds and ambitions. The investors who remain relevant are the ones who keep growing alongside the ecosystem they serve.
There is a growing body of evidence that diverse investment teams generate stronger returns, in part because they access a wider range of deal flow and evaluate opportunities through a broader set of lenses. Firms like Side Door Ventures are contributing to this evidence. When a team brings genuinely different professional backgrounds to the table, they are better positioned to identify founders and opportunities that a more homogeneous group might overlook.
Your unique perspective is not an obstacle on the path to becoming an effective investor. It may well be the foundation on which your entire practice is built.
Special thanks to Drew Gonzales and the team at Side Door Ventures, who generously shared their time and perspective for this piece. The venture capital community thrives when investors at the forefront of the industry open the door for the next generation — helping aspiring investors find their footing, develop genuine conviction, and contribute meaningfully to the ecosystem.
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