A venture capitalist's career security directly impacts the founder relationship. VCs with a proven track record (like Sequoia's Andrew Reed) act as supportive partners. In contrast, junior or less successful VCs often transfer pressure from their own partnerships onto the founder, creating a stressful and counterproductive dynamic.

In today's founder-centric climate, many VCs avoid confrontation to protect their reputation (NPS) within the founder network. This fear of being blacklisted leads them to abdicate their fiduciary duty to shareholders, failing to intervene even when a company's performance is dire and hard decisions are needed.

A founder's request for help in an investor update should be placed at the very end. This tactic, similar to Van Halen's 'no brown M&Ms' clause, serves as a test to see which investors read the update thoroughly and are genuinely engaged enough to offer assistance.

A powerful, low-effort fundraising tactic is to maintain two investor update lists: one for current investors with full transparency, and a "dream investor" list. BCC your dream list on polished, highlight-reel updates showcasing strong traction and momentum, creating inbound interest without a formal ask.

To manage investor expectations effectively, adopt a contrarian communication cadence. Only report good news (like a major deal) after it has officially closed, since many B2B deals fall through at the last minute. Conversely, report bad news as early as possible. This builds trust by preventing over-promising and demonstrating transparency when it matters most.

The most fulfilling and effective angel investments involve more than capital. Founders benefit most from investors who act as operators, offering hands-on help and staying involved in the business. This approach is more rewarding and can lead to better outcomes than passive check-writing.

To avoid stalled deals, continuously test the prospect's engagement. If a stakeholder consistently fails to meet small commitments—like providing requested information on time—it is a strong indicator that the deal is not a priority for them and is at high risk of stalling.

Instead of presenting information that can be read in an email, a successful founder sent updates beforehand. This freed up meeting time for strategic discussions on product, capital, and hiring, which accelerated the company's growth.

A frequent conflict arises between cautious VCs who advise raising excess capital and optimistic founders who underestimate their needs. This misalignment often leads to companies running out of money, a preventable failure mode that veteran VCs have seen repeat for decades, especially when capital is tight.