In his two decades running Cisco Systems Inc., John Chambers transformed what was a small networking-equipment company into a tech giant. His second act? Investing in and coaching more than a dozen startups with the hope of creating the next Cisco.
After retiring as Cisco’s executive chairman last year (he stepped down as chief executive in 2015), the 68-year-old Silicon Valley pioneer launched a venture-capital fund, JC2 Ventures, with $100 million of his own money. But it’s not just his money at work. To the fledgling companies...