Q. Were you an entrepreneur early on?
A. As far back as I can remember. My mother says that when I was about 4 years old, I was selling my toys. Later on, I had a paper route, but I didn’t stop there. I started selling synthetic motor oil to the people on my paper route. I figured that if I was already collecting the money for the papers, I could sell them oil, too. I also rebuilt and sold bikes that I pulled out of the Dumpster. Then, when I was about 19, I got my first PC. I just fell in love with software.
Q. You’ve started a few companies. What were some early leadership lessons you learned, particularly about culture?
A. My aspirations were always bigger early on than our resources. The way that manifested itself was that I never raised enough money early on to make money less of a factor in the way we made decisions. That meant I was either always pressured to ship software that wasn’t quite ready, which is a little bit of a death spiral, or I was always raising money within a few days of payroll — and asking the employees to trust me and to not quit.
So I was trying to be bigger than I could afford to be, and your decision-making is always convoluted by these factors. That was a big early lesson. It ingrained in me the importance of matching the entrepreneurial aspirations with the resources. Those all have to be aligned. And ever since, I’ve always raised money when I don’t need it ahead of time, for a rainy day. I just never put myself in that position again.
Q. Other big lessons?
A. I would say the overarching lesson is that there are no shortcuts, no Hail Marys, no silver bullets. It’s easy, early on, to think that you can somehow just jump right to the endgame. I can tell you that kind of thinking is pretty dangerous and unhealthy. In my experience, when you reach the goal you’re after, more often than not it’s fairly well deserved by the time you get there.
Here’s another lesson I learned. When you’re younger, you create a lot of expectations about who you’re going to be, where you’re going to be when you’re 40. It’s as if life past 40 doesn’t exist. So when you think of your relationship to time in that construct, you’re very impatient. My mind-set at 20 was that I had self-imposed deadlines that ended at 40.
But here’s the paradox. When you get to 40, a couple of things happen. You look at the second half of your life, and you realize that life is not endless, and that it is very finite. Yet somehow you can learn patience. I became very cognizant of the relationship between patience and time and decision-making. When I became patient, I simply made better decisions.
Q. So much of leadership is about finding the right balance point. Other thoughts on that?
A. One of the things I’ve really come to appreciate is that you tend to work harder when you’re winning. So you have to make sure that when you’re setting goals for people and the organization, they aren’t so far out that they’re unachievable, which will leave people demoralized.
You have to be careful and thoughtful about the way you set expectations. You don’t want them to be slam-dunks, but you don’t want them to be unattainable, either. They need to be within the realm of attainable. Even though you don’t have every step of the way figured out, you’re pretty confident that you’re matching the resources and the talent and the goals, and that all of those are aligned.
You can either create a circumstance where you build this positive vortex where everything right out of the gate is leading you toward more and more success, where you’re more motivated to not miss, or you can become trapped in what I call a cyclone of doom. And they start with these very small, seemingly innocuous decisions almost out of the gate and then they build on one another. So you’re either heading down or you’re heading up.
Q. How do you hire? What qualities are you looking for?
A. There is a subtle but important difference between people who want to work at a company to do something great and people who want to go to a company because they want to join something great. One group wants to pull and one group wants to ride.
Q. What questions do you ask to determine that?
A. I listen carefully to the language they use as we’re talking. I haven’t distilled it to a question yet that embodies the difference between these two, but oftentimes it just shows up in conversation in little ways. Somebody might say: “I’ve always liked what you guys were about. I’ve taken a look at what you’re offering and I can see how I can help.” They’ve identified a need and they’ve assessed their own skill set and they see how they can bring value.
Q. And what’s the off-key version of that?
A. I’ve had conversations where people will say: “I’ve visited your ‘About’ page and your ‘Culture’ page and your ‘Career’ page and it looks like a lot of fun. You guys look like you have a great culture.”
Q. What advice would you give aspiring entrepreneurs?
A. Everyone talks about the role of persistence, and I’ve come to like this one-liner: “The world filters out the uncommitted.” It’s not just entrepreneurship — it’s true about anything you want to do.
I also see a lot of brilliant people overthinking. They overanalyze an idea before it’s even off the ground. They have a smart idea, but they spend all their time thinking about all the what-ifs. By the time they’ve done their risk assessment, they don’t do anything. It’s like, “Well, what’s the point?”
Yes, there are all sorts of unknowns. I like to say the first step is not nearly as big as you think, and success takes a lot longer than you might think. It’s that weird dichotomy. The first step literally is just to say you’re going to do it, and then start doing it.
A. As far back as I can remember. My mother says that when I was about 4 years old, I was selling my toys. Later on, I had a paper route, but I didn’t stop there. I started selling synthetic motor oil to the people on my paper route. I figured that if I was already collecting the money for the papers, I could sell them oil, too. I also rebuilt and sold bikes that I pulled out of the Dumpster. Then, when I was about 19, I got my first PC. I just fell in love with software.
Q. You’ve started a few companies. What were some early leadership lessons you learned, particularly about culture?
A. My aspirations were always bigger early on than our resources. The way that manifested itself was that I never raised enough money early on to make money less of a factor in the way we made decisions. That meant I was either always pressured to ship software that wasn’t quite ready, which is a little bit of a death spiral, or I was always raising money within a few days of payroll — and asking the employees to trust me and to not quit.
So I was trying to be bigger than I could afford to be, and your decision-making is always convoluted by these factors. That was a big early lesson. It ingrained in me the importance of matching the entrepreneurial aspirations with the resources. Those all have to be aligned. And ever since, I’ve always raised money when I don’t need it ahead of time, for a rainy day. I just never put myself in that position again.
Q. Other big lessons?
A. I would say the overarching lesson is that there are no shortcuts, no Hail Marys, no silver bullets. It’s easy, early on, to think that you can somehow just jump right to the endgame. I can tell you that kind of thinking is pretty dangerous and unhealthy. In my experience, when you reach the goal you’re after, more often than not it’s fairly well deserved by the time you get there.
Here’s another lesson I learned. When you’re younger, you create a lot of expectations about who you’re going to be, where you’re going to be when you’re 40. It’s as if life past 40 doesn’t exist. So when you think of your relationship to time in that construct, you’re very impatient. My mind-set at 20 was that I had self-imposed deadlines that ended at 40.
But here’s the paradox. When you get to 40, a couple of things happen. You look at the second half of your life, and you realize that life is not endless, and that it is very finite. Yet somehow you can learn patience. I became very cognizant of the relationship between patience and time and decision-making. When I became patient, I simply made better decisions.
Q. So much of leadership is about finding the right balance point. Other thoughts on that?
A. One of the things I’ve really come to appreciate is that you tend to work harder when you’re winning. So you have to make sure that when you’re setting goals for people and the organization, they aren’t so far out that they’re unachievable, which will leave people demoralized.
You have to be careful and thoughtful about the way you set expectations. You don’t want them to be slam-dunks, but you don’t want them to be unattainable, either. They need to be within the realm of attainable. Even though you don’t have every step of the way figured out, you’re pretty confident that you’re matching the resources and the talent and the goals, and that all of those are aligned.
You can either create a circumstance where you build this positive vortex where everything right out of the gate is leading you toward more and more success, where you’re more motivated to not miss, or you can become trapped in what I call a cyclone of doom. And they start with these very small, seemingly innocuous decisions almost out of the gate and then they build on one another. So you’re either heading down or you’re heading up.
Q. How do you hire? What qualities are you looking for?
A. There is a subtle but important difference between people who want to work at a company to do something great and people who want to go to a company because they want to join something great. One group wants to pull and one group wants to ride.
Q. What questions do you ask to determine that?
A. I listen carefully to the language they use as we’re talking. I haven’t distilled it to a question yet that embodies the difference between these two, but oftentimes it just shows up in conversation in little ways. Somebody might say: “I’ve always liked what you guys were about. I’ve taken a look at what you’re offering and I can see how I can help.” They’ve identified a need and they’ve assessed their own skill set and they see how they can bring value.
Q. And what’s the off-key version of that?
A. I’ve had conversations where people will say: “I’ve visited your ‘About’ page and your ‘Culture’ page and your ‘Career’ page and it looks like a lot of fun. You guys look like you have a great culture.”
Q. What advice would you give aspiring entrepreneurs?
A. Everyone talks about the role of persistence, and I’ve come to like this one-liner: “The world filters out the uncommitted.” It’s not just entrepreneurship — it’s true about anything you want to do.
I also see a lot of brilliant people overthinking. They overanalyze an idea before it’s even off the ground. They have a smart idea, but they spend all their time thinking about all the what-ifs. By the time they’ve done their risk assessment, they don’t do anything. It’s like, “Well, what’s the point?”
Yes, there are all sorts of unknowns. I like to say the first step is not nearly as big as you think, and success takes a lot longer than you might think. It’s that weird dichotomy. The first step literally is just to say you’re going to do it, and then start doing it.
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