"Many a man thinks he is buying pleasure, when he is really selling himself to it."The classic 20-minute investor pitch, wherein entrepreneur, PowerPoint and investor come together, can be: (1) a clash of powerful egos where no useful information is shared, but all parties retain their (fragile) sense of self, (2) the supplicant (i.e., the pitcher) tries to entice the money (investor) with promises of vast, relatively easy riches or (3) an egoless, discerning mutual exploration where entrepreneur and investor map their respective known knowns and known unknowns, while also acknowledging that there are things that just can’t be known, at least in that moment anyway. Scenario (3) can take an hour or a month, but both parties will be better for it. At the very least, they can agree to disagree and come away smarter and more informed about the world. Or, alternatively, they can stick with a tired script and take their chances accordingly. There is one view where entrepreneurs are “selling” their concept to investors. In this mode, the pitcher tries to convince a usually jaded and skeptical investor with data, opinion and experience. With this approach, the investor needs clear proof there is money to be had. To be sure, there are plenty of such investors and some do very well. However, these types of exchanges too often take on the stilted and artificial character of a televised presidential debate or, worse, any episode of “Shark Tank.” A different view of a pitch is more like a date, where (ideally) two curious and discerning parties thoughtfully, constructively and even playfully try to determine if the person in front of them has the qualities, interests, values, beliefs and goals that they too have, admire and/or seek. A “no” in this exchange is not necessarily a rejection of the person or the quality of their idea. Rather, it is just not a good match, period. An entrepreneur’s most precious resource is time. Capital, colleagues working at a high tempo, customer patience with a klunky product and lack of competition all have a short half-life. Asking for money can be a burden or an opportunity. It is up to the entrepreneur and investor to determine which it will be.