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.
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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.
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.
Applying the "weird if it didn't work" framework to fundraising means shifting the narrative. Your goal is to construct a story where the market opportunity is so massive and your team's approach is so compelling that an investor's decision *not* to participate would feel like an obvious miss.
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.
Desperation repels investors. Negreanu advises against front-loading a pitch with an ask. Instead, talk passionately about your project, then explicitly state you're not actively seeking money but are "open to listen." This creates scarcity and shifts the power dynamic, making them want in.
A powerful fundraising tactic is to continually increase your total round size as you hit initial targets. This allows you to always be '50% closed' or more, constantly signaling momentum and de-risking the opportunity for new investors you speak with.
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.
For their seed round, the founders scheduled all VC meetings back-to-back over just two days. This tactical move not only manufactured urgency and social proof among investors but also served as a forcing function to rapidly refine their pitch with each successive meeting.
Founders mistakenly believe large funding rounds create market pull. Instead, raise minimally to survive until you find a 'wave' or 'dam.' Once demand is so strong you can't keep up with demo requests, then raise a large round to scale operations and capture the opportunity.