Contrary to the prevailing wisdom of staying private as long as possible, VC Keith Rabois counsels his portfolio companies to pursue an IPO once they hit ~$50 million in predictable revenue. He believes the benefits of being public outweigh the costs much earlier than most founders think.

While multi-stage funds offer deep pockets, securing a new lead investor for later rounds is often strategically better. It provides external validation of the company's valuation, brings fresh perspectives to the board, and adds another powerful, committed firm to the cap table, mitigating signaling risk from the inside investor.

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.

For a rising media company, securing an investment from an industry titan like former CNN CEO Jeff Zucker was a strategic move for market credibility. This validation signaled to partners and competitors that Front Office Sports was a legitimate player, accelerating their path to the top tier of the industry.

When founders invest their own money, it signals an unparalleled level of commitment and belief. This act serves as a powerful 'magnetic pull,' de-risking the opportunity in the eyes of external investors and making them significantly more likely to commit their own capital.

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.

When evaluating follow-on opportunities, the conventional wisdom is to look for a Tier 1 VC leading the round. However, a specialized fund with deep industry expertise leading a Series A can be an equally powerful, or even stronger, positive signal for a company's potential and market fit.

Historically, a bridge round signaled a company was struggling. Now, this signal is split. A new class of 'bridge' is emerging as a pre-emptive investment from enthusiastic investors wanting to deploy more capital into a fast-growing company before its official priced round, making it a positive indicator in some cases.

Unlike in tech where an IPO is often a liquidity event for early investors, a biotech IPO is an "entrance." It functions as a financing round to bring in public market capital needed for expensive late-stage trials. The true exit for investors is typically a future acquisition.