Raise capital when you can clearly see upcoming growth and need resources to service it. Tying your timeline to operational milestones, like onboarding new customers, creates genuine urgency and momentum. This drives investor FOMO and helps close deals more effectively than an arbitrary deadline.

The best time to raise money is when your company doesn't desperately need it. Approaching investors from a position of strength gives you leverage. If you wait until you're desperate, you will be forced to accept expensive, highly dilutive capital.

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.

Beehiiv's founder sends investor updates to both backers and VCs who passed on investing. This tactic keeps potential future investors warm without time-consuming meetings and creates powerful FOMO. This strategy helped them raise their Series A in one week.

For startups experiencing hyper-growth, the optimal strategy is to raise capital aggressively and frequently—even multiple times a year—regardless of current cash reserves. This builds a war chest, solidifies a high valuation based on momentum, and effectively starves less explosive competitors of investor attention and capital.

Venture rounds are compressing and conflating, with massive "seed" rounds of $30M+ essentially combining a seed and Series A. This sets a dangerous trap: the expectations for your next funding round will be equivalent to those of a traditional Series B company, dramatically raising the bar for growth.

Never tell investors you've raised zero. The best narrative is that the round is nearly complete, creating urgency and social proof. This makes attracting the final checks easier, as no one wants to be the very first money in a cold round.

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.

Instead of a formal roadshow, founders should let future lead investors invest small amounts months in advance. Providing them with regular updates and hitting stated milestones builds immense trust, making the actual fundraise a quick, targeted process that optimizes for partner over price.