A Lightspeed partner missed investing in Postman despite building high conviction. Because the founder wasn't officially fundraising, the VC hesitated. By the time they acted, a competitor had closed the deal hours earlier. In competitive, off-cycle rounds, conviction requires immediate action.

The cost of inaction can be immense. One speaker's "worst investment" wasn't a loss but passing on three startups in his direct area of expertise—Polymarket, Calshee, and Whatnot. Despite being an early user and having direct contact with the founders, he failed to invest, missing out on multi-billion dollar outcomes.

Effective due diligence isn't a checklist, but the collection of many small data points—revenue, team retention, customer love, CVC interest. A strong investment is a "beam" where all points align positively. Any misalignment creates doubt and likely signals a "no," adhering to the "if it's not a hell yes, it's a no" rule.

Early-stage startups can't afford to be strung along by enterprise prospects. The goal isn't just to close deals, but to get feedback quickly. Founders must design a sales process that forces a decision, because a "long maybe will kill you." It's better to get a fast "no" and move on.

Small funds and solo GPs can gain an edge by not reserving capital for follow-on rounds. This strategy enforces discipline, avoids cognitive biases like sunk cost, and recognizes that the skill set for pre-seed diligence is fundamentally different from that required for later-stage investments.

To avoid confirmation bias and make disciplined capital allocation decisions, investors should treat every follow-on opportunity in a portfolio company as if it were a brand-new deal. This involves a full 're-underwriting' process, assessing the current state and future potential without prejudice from past involvement.

An investor's best career P&L winners are not immediate yeses. They often involve an initial pass by either the investor or the company. This shows that timing and building relationships over multiple rounds can be more crucial than a single early-stage decision, as a 'missed round' isn't a 'missed company'.

The most critical decision in venture isn't the final investment vote but the mid-funnel choice of which companies get a deep look. The costliest errors are false negatives—great companies dismissed prematurely. Firms should therefore optimize process hygiene at this stage, implementing mandatory post-meeting debriefs to avoid these misses.

A truly exceptional founder is a talent magnet who will relentlessly iterate until they find a winning model. Rejecting a partnership based on a weak initial idea is a mistake; the founder's talent is the real asset. They will likely pivot to a much bigger opportunity.