Contrary to the 'get in early' mantra, the certainty of a 3-5x return on a category-defining company like Databricks can be a more attractive investment than a high-risk seed deal. The time and risk-adjusted returns for late-stage winners are often superior.

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.

Instead of being discouraged by over 100 rejections, Canva's founder treated each one as a data point. She added new slides to her pitch deck to pre-emptively address every objection—such as market size or competition—making the pitch stronger and more compelling with each "no."

Frame your initial angel investments as a sunk cost, like business school tuition. Instead of optimizing for immediate financial returns, focus on building relationships, acquiring skills, and developing a strong reputation. This long-term mindset reduces pressure and leads to better, unforeseen opportunities down the line.

To win highly sought-after deals, growth investors must build relationships years in advance. This involves providing tangible help with hiring, customer introductions, and strategic advice, effectively acting as an investor long before deploying capital.

Instead of dismissing harsh criticism, extract the underlying truth. A brutal investor rejection focused Gamma on intertwining product and growth from the very beginning, acknowledging the difficulty of competing against incumbents. This became a foundational part of their strategy.

Competing to be a founder's "first call" is a crowded, zero-sum game. A more effective strategy is to be the "second call"—the specialist a founder turns to for a specific, difficult problem after consulting their lead investor. This positioning is more scalable, collaborative, and allows for differentiated value-add.

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.

The founders of Free Soul endured multiple rejections, including literally being laughed out of rooms. They frame this brutal process as a necessary filter that weeded out misaligned VCs and ultimately led them to investors who were personally connected to their mission.