"Startup.com" is a documentary filmed during the dot com bubble burst that follows the life of a start-up, GovWorks.com, and its two co-founders and CEO's, Kaleil Tuzman and Tom Herman. The film focused mainly on the period of time when Kaleil was raising VC (venture capitalist) funds prior to their IPO (initial public offering), and short periods of operation after the IPO. The main focus was really on the relationship between the two co-founders, Kaleil and Tom. Kaleil left Goldman-Sachs to help get the company off the ground, and his expertise in finance and procedures for funding gave him an edge in the initial stages of the business. Though the friendship between the two CEO's was very interesting (and I found quite detrimental to the business overall), the most interesting part of the movie were the meetings with VC's. The meetings seemed very uncomfortable, with many of the VC's criticizing (tearing apart really) the business plan for GovWorks. The last meeting shown in detail (the biggest investor who they didn't end up working with -- their name eludes me at the moment) was the most uncomfortable, mainly because both parties seemed hostile and un-trusting of one another. This is a process that I hopefully will never be required to be a part of, because I cannot stand tension like that.
Something surprising about Kaleil was that his lifestyle was very different from Tom's. Tom (I recall) owned a large retreat where he invited the entire company, while Kaleil seemed to live in small apartments or hotel rooms (a rather modest lifestyle for a CEO). This could possibly be the way that the filmmakers portrayed them, but it highlighted an underlying message that I felt was either fabricated or was an actual truth: Kaleil is a savvy businessman, while Tom is a passionate, techy idealist. Although neither of them came out of the business on top (as was glazed over in the end of the film), you leave assuming that Kaleil will continue to be successful, while Tom will probably find his place somewhere else (other than as a CEO). It seems that this is a good assumption, as Kaleil is now a board member for multiple companies/firms (according to Wikipedia) and Tom is obscured. The biggest lesson I took away from this documentary was that it is ill-advisable to enter into a partnership with someone who doesn't have the same vision as you do. Either one of these men could have had a better vision for the company, depending on how you look at it, but it was obvious that their vision was not the same. In any case, friendship should never get in the way of business, bottom line.
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