On this special segment of the Full Ratchet, the following
investors are featured:
Each investor describes an outstanding entrepreneur that
they’ve worked with and what key traits and behaviors
make for the best startup leaders.
Nick: In this special segment, we have Mamoon Hamid of the Social+Capital Partnership. Mamoon, have you had the pleasure of working with or investing in an exceptional founder? And if so, we hate to make you choose just one, but can you talk about what made the entrepreneur so great and unique?
Mamoon: Yeah, I mean, I feel pretty fortunate to have worked with a number of really special entrepreneurs from Aaron Levie, Stewart Butterfield now, David Sacks, Owen McCabe at Intercom who some of you may not have heard of, or Gio Colella at Castlight—I mean, I can just keep naming them down the list and I’ve been pretty fortunate along those lines to work with some pretty special people.
And I would say, I can call out Aaron because that was my first investment and my first relationship with a CEO where I got to work very closely with is Aaron Levie at Box. I invested in Box, and really in Aaron in 2007, when it was a ten person team in Palo Alto with a consumer file storage company where consumers were uploading videos and music illegally and there’s a decided pivot from that type of business to really to serving the business market. We didn’t even call it enterprise because this seemed like such a huge leap to make. But really I would say, Aaron had never had a job in any company, but really he had the vision and he was thinking like five steps ahead in terms of what it meant to be a content management platform for businesses. And the vision was way ahead of where the company was but there was this step by step approach which I think he knew in his mind on how to execute behind achieve what he’s achieved today.
So is truly a special founder. At the time, I remember when I met Aaron for the first time. Within five minutes, I knew that I wanted to invest in—Aaron, actually. Box was great, but Aaron was special. And I think Box appealed to me because the notion of having a share drive in a file storage cabinet in the office for a small firm like ours made no sense, but having it in a cloud for everyone from any device made complete sense. So, obviously, I bought into the vision of Box, but really a lot of these companies, they’re typically in very competitive areas, and if it wasn’t for the individual, it wouldn’t be the same company. I would say Stewart and Slack in a very competitive area, but they’ve stood out. David Sacks and Yammer, in a very competitive area and not first to market, but it stood out. So there’s a lot of vision, grit, passion, execution involved in all of these and it’s because these people are, I would say, special.
Nick: Is there one thing in particular about Aaron that really jumped out at you?
Mamoon: You know, it was—even though at the time, I think he was twenty, maybe twenty-one—he’d been starting companies on the internet since he was thirteen, so really…a lot of times we say “Oh, this guy’s young” he’s young, but he’s been on the internet as long as most internet entrepreneurs were in 2007. So, really, he was like a thirty year old internet entrepreneur rather than a twenty-one year old. Because he was buying and selling and creating sites, I think Box was probably like his fourth or fifth internet company.
Mamoon: So he was more experienced than most.
Nick: Just like the nineteen year old kid who graduates from college, right?
Mamoon: Oh—I don’t know any of those.
Nick: On today’s special segment, we have Eric Gasser. Eric, have you had the pleasure of working with or investing in an exceptional founder? And if so, can you talk about what make that entrepreneur so great and unique?
Eric: There’s a company here in town, Cursive Labs. It’s a small incubator—I call it a brain trust, and they kind of get crabby with me about it, but basically it’s run by Jon Belmonte. He came from Active Networks, and he’s probably one of the smarter CEOs that I’ve met. The whole notion of the organization is “Look, we’re gonna take really smart people and get them all together, and we’re gonna see what we can come up with over a set series of months.”
This type of investment isn’t for the faint of heart. Basically, at the end of twenty-four months, you either make money and you do something or you don’t. This isn’t like we’re starting with a product and you’re investing. This was “We’re gonna get some guys together in a really funky house in downtown San Diego and see what we can come up with, okay.” And I know that we’ve all made these investments, we just didn’t know we were doing it.
Eric: And so I went into this thing eyes wide open. It’s called Cursive Labs. Jon hosts these brainstorming sessions where he takes all these ideas and throws them up on the board. And what’s really cool is he pulled together some of the talent in San Diego to say “Look, one of the value props that we’re gonna have to our other investors is the ability to sort through these ideas based on what we see in the community.” And so if him and his team come up with an idea, and they put it up on the board, their visibility to what’s hiding and what’s in stealth is high, but not as high as someone out shopping for deals.
So I liked it because I thought I could help them screen deals quicker. That would be my value add. I’m gonna be an investor and I’m gonna be able to screen these ideas quicker. The second I walked in the room for our very first brainstorming session, there was four concepts on the wall, and I hadn’t seen them at all. And that’s the kind of thinking and brainpower and process oriented brain trust. You’re leveraging the brains of all these people in this room to come up with really good ideas. Ultimately, some of those will succeed, some will fail, but eventually they’ll get one, and hopefully it’ll be in the next sixteen months because I think that’s all I have left. [laugh]
So Jon Belmonte can actually see what’s coming. He can also kind of mitigate risk by reaching out to existing investor base. When he has problems, when he needs help, he calls. When he needs connections, he calls. We’re all overwhelmed with email these days, and one of the things I really like about founders is not just sending me an email when s— hit the fan, but to call some of the people that can actually help them and say “Look, s— hit the fan, everything’s going sideways, I need help.”
And that’s the difference between an average CEO and an exceptional CEO, is being able to see stuff coming and try to mitigate it. At the same time, be forward thinking enough and really focus on what the customer wants instead of tracking revenues or some of the other metrics that matter least when you’re build an organization.
Nick: On today’s Investors’ Stories segment, we have Charlie O’Donnell of Brooklyn Bridge Ventures. Charlie, have you had the pleasure of working with or investing in an exceptional founder? And if so, could you talk about what made that entrepreneur so great and also highly some of the characteristics and behaviors that made founders exceptional?
Charlie: I’ve had the pleasure of working with a lot of exceptional founders, actually. It’s interesting, because in many ways you might be able to tell that somebody is an exceptional person, but you don’t know how they’ll turn out as a founder. Those things don’t always square. Or they could be a great founder and maybe the business is just tough.
So I’m very careful when I use the term “great founder,” because I think it implies something born with. There are people who are very effective, given a certain set of information. There are lots of different types of founders, and I try not to get too caught up in sort of pattern matching.
I would say one of the best founders that I’ve gotten chance to work with is Raul Gutierrez from Tinybop. And Raul is a dad of two kids and worked in the movie business a long time and it’s managed creatives helped get movies made. He came to me a couple years ago and said “I want to build a kids app business.” Actually, he had a much broader vision and said “I want to build a toy business.” And inspired by the Richard Scary books and the Children’s Encyclopedia and the kind of things I grew up with, and “I want to build really high quality toys of tomorrow company for kids.” And had a really great vision laid out, “These are the apps we’re gonna release over the next few years and they’re gonna produce some really great illustrated assets that we’ll be able to carry into other channels and here’s some models of success and I’m going after.”
He’d done his research. He probably spent the better part of a year analyzing the market, downloading everything that was available. And so he’s a very carefully considered decision maker. So a unique set of inspirations, you know, just being a dad, and appreciating what he grew up with as a kid. And ground up in an era—he’s late forties where just the books and things kids played with and read were just really well crafted, the things he got exposed to.
And Tinybop had turned out to be a terrific company. They just released their latest app called Robot Factory, and it’s—will admit to playing it a lot more than I probably should given my age level. But you can build robots and run them around in a world and you can decide where or not each slinky leg has a rocket attached to it—which, by the way, creates all sorts of navigation problems for your robot, just as a tip for anybody using it.
And I think what’s really strong there, he’s built a really great company culture that values creativity and he’s gotten some people working for him that probably wouldn’t work for anyone else. They probably would otherwise be consultants and freelancers if they weren’t working for Raul and for that company. And so it’s been a really great experience.
Nick: Something you said there about Raul, I think about sort of the vision founders and the execution founders. Doing the right things or doing things right. And it’s hard to find those founders who are a combination of two.
Charlie: You actually nailed something that I’ve been talking about with people over the last couple of days. It’s popped up. It’s why I was never a particularly good founder. A lot of times, we romanticize the idea of starting a company and this visionary founder and the idea of like “I have an idea and this high level pitch” and all this sort of stuff. And a lot of founders get into it, and then they realize, “Wow, actually running a company is a bunch of tedious crap. This isn’t what I signed up for!”
Nick: “This is hard.”
Charlie: “This is not only hard, but it’s the kind of stuff that I don’t really want to do. And nobody told me this was gonna be”—— Company in the job recruiting space, and we were doing some interesting data analyses and I had to hand categorize 65,000 job titles. And that was like two weeks of my time that I’ll never get back! And nobody told me about that. Pitching was a lot easier.
And so, yeah, you’re absolutely right. Both the visionary founder and——takes time to sit with their audio engineer and make sure the sound it just right. And so he does both and that is absolutely rare.