The acquisition of Hunter Douglas wasn't a quick transaction; it resulted from a 15-year relationship with the founding family. This long-term trust-building created a unique opportunity window when the family was ready for a succession plan, bypassing a competitive process.

An investor's best career P&L winners are not immediate yeses. They often involve an initial pass by either the investor or the company. This shows that timing and building relationships over multiple rounds can be more crucial than a single early-stage decision, as a 'missed round' isn't a 'missed company'.

In a competitive M&A process where the target is reluctant, a marginal price increase may not work. A winning strategy can be to 'overpay' significantly. This makes the offer financially indefensible for the board to reject and immediately ends the bidding process, guaranteeing the acquisition.

Landing a major client in the B2B health tech space requires extreme persistence. Sales cycles can last for years, and success often depends on the long-term effort of 'chipping away' at barriers and objections. Resilience is more critical than having the perfect initial pitch.

Instead of dismissing harsh criticism, extract the underlying truth. A brutal investor rejection focused Gamma on intertwining product and growth from the very beginning, acknowledging the difficulty of competing against incumbents. This became a foundational part of their strategy.

Orlando Bravo didn't get a return offer from his internship. Instead of giving up, he sent 500 resumes and cold-called firms, landing his pivotal role just two weeks before graduating. It shows that persistence, not a linear path, is key to breaking into competitive fields.

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.

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.

A 'no' from a high-value candidate shouldn't be the end of the conversation. The best approach to recruiting is to be persistent over a long time horizon. A rejection today may turn into a hire five years from now if you maintain the relationship.