Instead of scheduling rigid, three-hour co-founder check-ins that often get canceled, adopt a 'counter-puncher' mindset. Keep important topics top-of-mind and seize spontaneous opportunities—like another meeting getting canceled—to have those crucial conversations. This fluid approach is more effective in a chaotic startup environment.

Contrary to the belief that success is measured by rapid email responses, the most important people for a founder to be responsive to are their own team. Prioritizing internal communication channels like Slack over an external email inbox ensures the team has the support it needs to execute effectively.

Status update meetings are a major productivity drain. Replace them with asynchronous videos (e.g., Loom). This method is more efficient, allowing people to consume updates on their own time. It also conveys more signal—tone, emphasis, and personality—than a written update, fostering better connection on distributed teams.

Engaging with founders a month before Demo Day, even without a formal pitch, provides a vital baseline. Witnessing their spectacular progress over that month creates a powerful second data point on execution velocity, making the investment decision far easier and more informed.

Prepared's founder rejected running a formal fundraising process. Instead, he had infrequent 'coffee chats' with investors to share progress. This built relationships and momentum, leading to preemptive term sheets and much faster closes without the distraction of a full-time fundraise.

CPC separates board meetings into two sessions: a virtual one for reviewing past results with functional leaders, and a subsequent in-person meeting for forward-looking strategy with the CEO. This structure prevents the common trap of getting bogged down in past performance when strategic, future-focused discussion is needed.

Adopt the private equity board meeting model: circulate a detailed brief a week in advance. This forces attendees to consume updates asynchronously. The meeting itself can then be dedicated entirely to debating critical, forward-looking decisions instead of wasting time on status reports.

Instead of using meetings for context-setting, Loom’s team sends a required 'pre-watch' video walkthrough of the strategy. This forces stakeholders to arrive with full context, allowing the live meeting to be shorter and entirely focused on critique, asking clarifying questions, and making decisions.

Instead of a top-down agenda, Brad Jacobs has his leadership team collaboratively create it for key meetings. Attendees submit and rank questions based on pre-read materials. Only the highest-rated topics make the final agenda. This bottom-up approach ensures the meeting focuses on what the team collectively deems most critical.