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The most significant investment mistakes arise from misallocating time and not leaving room for creative thought. By intentionally avoiding an over-scheduled calendar, investors can remain prepared for the "bolts of lightning"—the unexpected insights and opportunities that drive success.
Entrepreneurs trapped in a constant cycle of 'doing' often neglect strategic thinking, perpetuating their problems. The solution is to schedule non-negotiable blocks of 'thinking time' and empower a personal assistant to fiercely protect that time from internal and external demands.
Treat strategic thinking as a formal, scheduled activity, not a passive one. By blocking time on your calendar for specific thinking formats—like a walking meeting with yourself or a dedicated commute session—you create the space for your subconscious to solve problems and generate novel insights.
Instead of constantly seeking the next project, trust that when the time is right, the opportunity will appear organically. By focusing on executing your current commitments, you create the space for the next idea to find you through a conversation, an article, or a chance encounter, rather than forcing it.
New VCs often rush to make deals to prove themselves, but this leads to a portfolio of mediocre companies. These investments consume a disproportionate amount of time and energy, leaving no bandwidth to pursue the truly exceptional, career-making opportunities that may appear later.
Mastering generative AI requires more than carving out an hour for thinking. It demands large, uninterrupted blocks of time for experimentation and play. Tavel restructured her schedule to dedicate entire days (like Mondays) to this deep work, a practice contrary to the typical high-velocity, meeting-driven VC calendar.
Many entrepreneurs resist scheduling because they view a free calendar as the ultimate reward for their hard work. However, this aversion to planning leads to missed opportunities and a lack of clear vision, which can cost millions in potential growth and success. True freedom comes from the structure planning provides.
The most effective investors deliberately carve out unstructured time for deep thinking and reading. This discipline contrasts with the common early-stage VC tendency to equate a packed calendar with productivity. True investment alpha is generated from unique insights, not just from the volume of meetings taken.
Instead of focusing solely on networking and deal flow sharing, a young investor's true advantage is having more time and fewer obligations. This allows them to conduct deep research, speak directly with buyers, and form a unique, proprietary thesis that goes beyond the surface-level chatter common in venture circles.
Venture capital isn't a constant sprint. It has distinct seasons, both in an investor's career (e.g., a 'deep learning' phase) and throughout the calendar year. Summer is for strategic thinking due to fewer meetings, while the period from Labor Day to Thanksgiving is peak deal-making season.
Terence Tao argues against hyper-optimizing one's time. Serendipitous interactions—like bumping into someone in a hallway or browsing a physical journal—spark new ideas. Over-scheduling and efficiency tools eliminate these random encounters, potentially stifling the unexpected connections that lead to breakthroughs.