“I actually thought I’d stay at Flexport my entire career.” Ben Braverman’s Path Into, and Out of, His Dream Job and Then Founding Saga, a New Venture Firm

Ben Braverman and I went to a women’s college. Not at the same time (I’m older), and after it went coed. But Vassar itself is a small school, so that plus its liberal arts focus means you don’t find many of us in Bay Area tech. Ben and I started to hang out because of the Vassar connection and then even more so because he was just so darn helpful. His experience at Flexport; his pay-it-forward nature; and his friendly user interface, made his a desirable angel/advisor for startups. So I wasn’t totally surprised when he shared moving from operating to venture capital. And I was glad to hear it was at a new firm of his own co-creation. Saga says they’re a ‘return to tradition’ and the trio of founding Managing Partners are committed to the craft and to one another. Excited to share more about Ben via Five Questions.

Hunter Walk: Flexport was a life-changing experience which of course in hindsight seems like a ‘no brainer’ job to take but I know at the start of things, it’s not always so clear. How did you originally get introduced to the startup and do you recall how you thought about the ‘pros and cons’ at the time?

Ben Braverman: There were no cons! I met Ryan at Duboce Park (we both had giant dogs). The few times in life when you meet an n of 1 person obsessed with a worthy quest, it’s genuinely obvious what you’re supposed to do. You’re supposed to join the mission and I did exactly that. Side note: really smart people get obsessed with the wrong quests all the time (see model trains or social discovery apps).

HW: As Flexport grew and created a leadership team, how did you decide about promoting from within versus hiring from the outside? Was it case by case for each individual role? Or was there a different framework/circumstances which influenced how you made the decision? And in the event you hired from outside, did existing high performers chafe at being ‘topped?’

BB: We built flexport during a somewhat dogmatic period and the new ‘founder mode’ trend is a reaction to that time in history. Lots of clever people told us there were fixed rules for span of control (aka number of direct…