Base intentionally constructs its cap table with a mix of investor types: growth funds for pattern matching, sector funds for domain expertise, strategic partners for market access (e.g., homebuilders), and endowments for long-term stability. This turns the cap table into an active asset beyond just capital.

The Jeeves founder strategically includes potential leads for his next funding round in his current round, even for a small check. This gives them an insider's view of the company's progress, building trust and making it easier to secure their lead investment in the subsequent round.

While first-time founders often optimize for the highest valuation, experienced entrepreneurs know this is a trap. They deliberately raise at a reasonable price, even if a higher one is available. This preserves strategic flexibility, makes future fundraising less perilous, and keeps options open—which is more valuable than a vanity valuation.

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.

The initial capital for a new fund-of-funds doesn't come from cold outreach to institutions. The process mirrors an emerging VC's first fundraise, relying on a personal network of operators, VCs, and high-net-worth individuals who already believe in the founder. The strategy is to work the existing network outward, not pitch institutions from day one.

Reflecting on his first company, Ryan Rouse's regret was not raising more capital from individual investors earlier. He stresses that founders often stop the difficult process of asking for money too soon, prematurely filtering out potential investors from their extended network due to the personal discomfort of the process. The key is to be relentless.

Raising venture capital is often a network-driven game. If you don't already have a network of VCs or a clear path through an accelerator, your focus should not be on fundraising. Instead, dedicate your effort to building a product people want and gaining traction. VCs will find you once you have something compelling to show.

A clever strategy for first-time fund managers is to raise smaller checks from a large number of operators and domain experts. While harder to execute, this turns the LP base into a powerful, built-in expert network for diligence and support, converting a fundraising challenge into a strategic asset.

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.