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"There are a couple of times that I would not raise money. The first is, when your business concept is still nascent and you are not exactly sure of the business model, it's a big mistake to take a large round of capital because you may be better off raising that capital later in your evolution. So keep that burn rate low until you know you actually have your concept proven. The other time, and I think it's the most important, is when you don't have great chemistry with the folks you are raising money from. A venture-backed company is inevitably a rollercoaster and you need to work with a partner who is going to be with you through thick and through thin. Therefore, you want to look at bringing on a new venture capitalist almost like a new executive that is going to be with you all the way through the ride." — Doug Mack