Playing Offense vs. Defense

Surviving and thriving requires both, but it’s too easy to fall into defensive mode.

As a venture capitalist, you can often find yourself perpetually playing defense. The constant influx of inbound deal flow alone consumes any amount of time which you allocate to it, leaving little room for anything else. Beyond that, there’s critical portfolio work, where being as responsive as possible to the founders who you support is paramount.

A glance at the typical VC’s calendar reveals a jam-packed schedule, often overscheduled down to the precise minute. I remember at the start of my career being struck that seasoned VCs whom I worked for were always running late, overwhelmed by their own calendars. Over time I realized, although we don’t like to admit it, that the reason is we as VCs are in the client service business.

We aspire to think of ourselves on a more noble plane than that - applying critical analysis and judgment about our investment decisions, righteously supporting founders, and virtuously shepherding capital with the utmost adherence to our fiduciary responsibility. However, in practice, we submit to entrepreneurs like the discerning customers which they are and treat our limited partners (LPs) with the responsiveness they deserve. Plus, for junior VCs, serving your superiors is also part of the job, but even now, I consider my partners as my clients, striving to be as attentive and thoughtful as possible. This set of circumstances means that your time is not always your own.

This observation leads us to the critical distinction between playing offense and playing defense in our daily lives as VCs. Playing defense encompasses all the reactive work we do: managing deal flow, supporting portfolio companies, and handling the day-to-day demands of the business. These tasks are crucial, but they can easily consume your entire schedule if you're not careful.

Playing Offense

Playing offense, on the other hand, involves proactive, strategic activities that can significantly impact your career and your firm’s success over time. Examples include:

1. Deep Work: Engaging in activities that require uninterrupted focus and/or a dedicated consistent practice, like writing, developing a social media presence, and conducting in-depth thematic research.

2. Proactive Outreach: Reaching out to founders and companies rather than waiting for them to approach you. Many of the best opportunities arise from systematic outreach to founders who align with your fund’s thesis, profile, and objectives.

3. Firm Building: While some view firm-building tasks as chores, they present significant opportunities. By contributing to your firm’s growth and success, you can enhance your own career prospects, especially by extending your tenure (don’t forget the second rule of venture capital: don’t lose your seat). This effort might include organizing events, assisting with a website redesign, and other non-investing activities which assist the firm. The key is to ensure your efforts are recognized and you get the credit for the effort put in.

4. Strategic Thinking & Action: Taking steps that may not have an immediate payoff but will benefit your career over the long term. This can involve developing new soft skills, personal brand building, and purposeful networking.

Balancing Offense and Defense

One of the most challenging aspects of our career journey, even for experienced VCs, is finding the right balance between offense and defense. It’s something which I struggled with for a long while, equating busyness with true productivity. For myself, I’ve found that the most successful tactic is to directly schedule time for offensive activities on your calendar, treating them with the same importance as your defensive tasks. While these slots can be moved if necessary, having them on your schedule ensures that they don’t get completely overlooked, prioritizing that they receive attention.

A balanced approach here is essential. Like a successful sports team, you need to play both offense and defense effectively. All your constituents are important, and being responsive to them is critical. Additionally, the serendipity which can arise from maintaining flexibility in your schedule, like attending events or taking random meetings, can lead to positive, unexpected outcomes.

Mastering the balance between playing offense and defense can set you apart over the long run. A successful VC career is made not by just addressing the immediate demands of the day, but also by prioritizing strategic steps that will benefit you and your firm over time.