Joe Stump on Working With Investors as a New Entrepreneur

In Chapter 9 of 17 in his 2011 Capture Your Flag interview, Internet entrepreneur and SimpleGeo CTO Joe Stump shares his experiences learning to work with startup company investors. In his 2009 Capture Your Flag interview, Stump shared how he developed a "tell it like it is" approach. He carries this into venture capitalist and investor meetings. Surprisingly, he finds his transparent and honest approach well-received. Stump is the co-founder and CTO at SimpleGeo (, a San Francisco-based mobile location infrastructure services company. Previously Stump was Lead Architect at Digg. He programs in PHP, Python, Django and enjoys scaling websites. He earned a BBA in Computer Information Systems from Eastern Michigan University.


Erik Michielsen:  How has your approach of telling it like it is went over with the investment crowd?  

Joe Stump:  Uh, surprisingly well, actually.  I think that the things that investors hate the most is the unknown.  They’ll talk about the more information that they have the better investment decisions that they can make.  And so I really don’t sugar coat anything, I tell them exactly what is going on and exactly how I feel like I fit in, and it’s resonated pretty well.  They know exactly what they’re getting and they know exactly where they stand on the whole thing and where I stand.  So, it’s gone over a lot better.  It’s a fine line between being overly abrasive and being honest and open.  And as long as I stray more on the open and honest and away from the abrasive, it’s gone mostly fine.

Erik Michielsen: What were you expectations going into those conversations and what has played out in reality?

Joe Stump: It’s really funny, I thought that basically a tattooed, t-shirted asshole who doesn’t filter himself coming into those offices on Sand Hill Road will basically get me thrown in jail and it’s been the direct opposite. I think what really resonates with them and I think actually terrifies them is that I’m okay with things failing because my failure is a lot better than most people’s.  

My failure is to go have a nice, cushy salary at Facebook or Netflix or something like that.  So, I don’t really care and that resonates with them but it also scares them because they know that a lot of other entrepreneurs that don’t have that possibility, particularly younger ones, the investors in part rely on the fact that if they fail that they go back to the ground floor and have to work their way up through the system.  And with me I’m like failing one rung down.  Like, it’s not a big deal.  So, I think that is good and bad for them.