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 reports/manager) – Jensen and his 60 direct reports hadn’t conquered the world yet. With lots of managers, you feel pressure to bring in ‘managers of managers’ from the outside.
Outside leadership is a series of paradoxes. The existing team always accepts them if the new leader is world class and the company is thriving. And yet, you’re also almost always better off just promoting someone from within – context and speed trump experience in most cases, for most startups. The second paradox though, is that we had a number of exceptional people leave the company too early because they were leveled too high, too fast. This was actually much more common than someone leaving because they were leveled (unless their new boss was an idiot). Balance in all things, I suppose.
HW: Did you ‘stay longer than you imagined you would’ or ‘leave before you were necessarily ready’ (even if it ended up being the right decision)?’ What was it like giving up your email address, so to speak? It can be very intoxicating to be at a high profile startup knowing that your identity kinda gets the rub of success along with the company.
BB: I actually thought I’d stay at Flexport my entire career. It’s an endless market (I’m a sales guy at the end of the day, remember) and you’re fixed squarely at the center of global commerce. You can’t imagine a more interesting window into global politics than leading a global transportation business. Unions, tariffs, geopolitics, the world’s largest ships and aircraft supplying the world with every conceivable good. It doesn’t get much better. Even the hurricanes in the American south are potentially related to global shipping – the poorly designed new sulfur regulations are likely increasing global warming and fueling hurricanes because we’re allowing the fleet to pump sulfur into the oceans instead of into the air in the name of progress.
Giving up the email address has tactically been quite a pain in the ass. I was so proud of Flexport that I used the email address to sign up for everything. Recently had to cancel HBO MAX as a result. There was no reason to use my corporate email address to watch the Sopranos other than that I just liked seeing it every day.
HW: I know from experiences within the Homebrew portfolio that you were doing some angel investing already, as well being very generous with your time as a formal/informal advisor to founders. Were you intentionally road testing whether you wanted to try venture capital before forming Saga, or was it more casual than that?
BB: My first angel investment ever was the Flexport seed. I also got advisory shares. This is the equivalent of going on a 7 figure run on your first trip to Las Vegas. I had a completely unrealistic expectation of my picking ability and assumed I’d be able to 100x my money in a few years. It hasn’t quite worked out that way but I did learn that I don’t get tired of meeting founders. My late Uncle Richard used to buy lottery tickets next door to a convent in Boston. He’d see the same nun buying tickets every week. He asked her, ‘you don’t seem particularly financially motivated – why do you play the lottery?’. She said ‘I’m here, talking to you. Look at all the fun I’m having for a dollar!’ That’s sort of how I feel about investing in startups at this point, except that I very much also do care about the outcomes.
HW: Saga has three GPs, essentially three cofounders. What you feel like you needed to be 100% sure of about these relationships before formalizing the commitment, versus things that you might not be absolutely sure about until you’re actually in business together (but you figured would work themselves out). Maybe put differently, is choosing cofounders for a venture fund more or less similar to choosing cofounders for a startup?
BB: Vibes. Max is the common thread – he and I and he and Thomson were friends for years. When he brought the 3 of us together, it just felt right. It was fun from the jump and never felt like work, even in the midst of doing hard things together. If you want a more objective answer for why the partnership works so well, we’re extremely different from each other and bring totally different skills to the partnership. There’s never a moment where it’s unclear who is supposed to do what to move the ball forward for Saga and our partners. In that way, very similar to a great CEO/CTO partnership in a startup. The big difference is that an investment firm makes a lot more sense to run as a partnership whereas the great startups often look at lot more like benevolent dictatorships.
Thanks Ben! See you on some cap tables!