Venture capitalist Ben Weiss has logged on to a video call to discuss his latest deal at about 7am in Tel Aviv, three hours into the ceasefire between Israel and Hezbollah, which he is hopeful – but not confident – will hold.

The New Zealand-born, Sydney-educated son of corporate raider and turnaround specialist Gary Weiss has just pulled off the toughest assignment of his career. It is one he proudly tells The Australian Financial Review his dad would not have touched, but which led one of his investment peers to declare he has “the biggest testicles in VC”.