There haven’t been many books written about venture capital. I’ve come across only one great journalistic account that brings the reader inside a venture firm: eBoys by Randall E. Stross, published in 2000. Stross chose wisely when zeroing on Benchmark, then a newly minted firm with a lot of buzz but no track record. A historian by training, Stross describes himself as a “writer-in-residence” inside Benchmark from 1997 to 1999. The resulting book gives a great sense of time and place while introducing readers to the six tall men (their average height is six feet, five inches) who backed eBay, Webvan, and other billion-dollar start-ups. Stross was there when eBay was a small thirty-person start-up eager for attention and there after its 1998 IPO—much to the chagrin of at least some of the partners, embarrassed by the unimaginable wealth they were pocketing. On his watch, each of the six partners had increased his net worth by approximately $350 million. Benchmark has been press shy ever since.
If you are looking to better understand the nitty-gritty of venture finance, there’s no better book than Venture Deals by Brad Feld, one of the venture world’s more well-respected practitioners, and Jason Mendelson, one of his partners. The book offers a readable primer on everything from the basics of a venture term sheet to negotiating tactics to the specific issues likely to come up at every round of funding. I’ll quote Dick Costello, the former CEO of Twitter, who said in an endorsement of the book that he wished this book had been around in his time to save him from having to learn “all the tricks, traps, and nuances on my own.”