Adding a deeply personal postscript (P.S.) to cold emails, such as referencing the recipient's favorite whiskey, demonstrates genuine research and builds rapport. This simple tactic humanizes the outreach and can dramatically increase the likelihood of getting a response from a busy executive.
In social business settings, focus attention on the partner of the person you want to influence. A positive opinion from a spouse, shared during the "car journey home," can significantly shape the ultimate decision. This indirect "power of pillow talk" is a subtle but highly effective influence strategy.
To build deeper relationships with potential investors or clients, explicitly suggest moving conversations from formal email to a personal channel like WhatsApp. This enables informal, rapport-building interactions that humanize you, making future business asks feel more natural and likely to succeed.
At 19, Harry Stebbings raised $1.75M by telling CEOs their competitors were interested (creating FOMO) and pricing sponsorships at $95k. This price point often falls just below the $100k budget line that requires more approvals, bypassing corporate red tape and securing a faster 'yes'.
The fear of failure in content creation is misplaced. If your content fails, it's typically because it gets no attention, meaning no one will even know you failed. The risk is asymmetric: failure is private and invisible, while success is public and rewarding. This mental model should encourage more people to start creating.
When investors say "no," don't just accept it. Reframe their decision as a potential mistake, comparing it to common investor errors like overlooking a great founder due to market concerns. This tactic, which turned two rejections into $12M, repositions you from supplicant to a confident peer and can reopen the conversation.
Getting access to high-level executives like Salesforce CEO Marc Benioff may require an extreme level of persistence. Harry Stebbings emailed him 53 times before getting a response. The key was that each follow-up included a new, personalized P.S., demonstrating thoughtful commitment rather than automated spam.
In a crowded venture landscape, a VC's most significant value-add can be their distribution. For example, a single LinkedIn post from Harry Stebbings about a portfolio company generated $4 million in revenue for them. This demonstrates how a VC's audience can provide tangible, immediate value far beyond advice or capital.