Alain Benzaken: I think in terms of my career, I’ve been involved in a lot of very successful internet startups. From early in my career, I worked at Priceline. It was really the early days of Priceline.
Alain Benzaken: Priceline was one of three companies that came out of the dot com boom. They were valued over a billion dollars.
Alain Benzaken: I was there very early on, I helped build a lot of core systems and since then, they’ve become, I think, the most successful stock on the New York stock exchange because they just had incredible growth.
Alain Benzaken: We had a lot of challenges early on. It was a crazy dot com boom, we went through craziness. The stock actually went from 160 to 2, so we’re sort of all in a very, very compressed time period. But it was actually, we really built a core product that has stood the stand of time.
Alain Benzaken: So I think that was probably my biggest success early on. Since then, I have also been involved in a bunch of different startups in the New York area, on East Coast.
Alain Benzaken: And the East Coast is a little different than the West Coast. It’s a lot more about the number, it’s not so much about let’s create some cool product and we’ll see if we can eventually monetize it.
Alain Benzaken: So it’s always been a little more challenging to find success stories even in New York area because if you see, it’s much more concerned about actually making money and exiting, and so forth.
Alain Benzaken: So in terms of that, I’ve always been very focused on interesting business models. So I’ve also worked at Buddy Media. I helped that company grow and eventually sold to Salesforce for 800 million dollars, one of the bigger New York city exits.
Alain Benzaken: I helped, at a slightly earlier stage, food52 raised their first angel round, so they’re doing great now. A big success story as well.
Alain Benzaken: And I was at TheLadders, we had a huge success story for a while. We’re doubling in size, we’re getting close to a hundred million in revenue.
Alain Benzaken: So on all these I think I’ve had a pattern of, maybe it’s picking the right companies to choose early on, to know when to come in and seek opportunity because I think a lot of that is important as well.
Alain Benzaken: As a technologist, you kind of have a choice a lot of times of what areas to get into so it’s not just a matter of, executing is important but also you can choose them upfront which of the ones you think have a potential opportunity.
Alain Benzaken: And I’ve made my share of mistakes as well but I think overall, I feel like in my my career, I’ve had some pretty good success stories.
Alain Benzaken: So everyone think leadership is about inspiring people and getting them to achieve more and there’s a large part of that. At the base level, to me, leadership is about influence, about using your influence, knowing how to use influence on maybe it’s one person, even in a lot of way it’s yourself as well.
Alain Benzaken: You need to sort of master that first and then you can apply to other people, and then to a larger group. And it’s really about knowing what the levers are and it’s almost different in every situation.
Alain Benzaken: Every company I’ve been at has been slightly different and every time I come in to a new situation, I try to remember, “Don’t fight like the last war.” And it’s very hard because you remember what you did wrong the last time, you’re like, “I’m not going to do that again.” But it’s always slightly different.
Alain Benzaken: And so, in terms of leading people, the basic things about you need to make decisions quickly. I think it’s important. Giving people the freedom to fail is important.
Alain Benzaken: Just giving them an environment where you want them to excel and to achieve as much as possible and I think that, if you can inspire people that way and really play to their strengths, which again is influence, which is really about understanding people and getting them to achieve more than they even think they can achieve.
Alain Benzaken: You know, I really don’t look at people as part of these are millennials or these are baby boomers, whatever. People are people, they all have the same needs and same sort of value systems that they have created in their heads, and so forth.
Alain Benzaken: So I think understanding them at a more elemental level than just part of generation, I’ve never really subscribed to a theory that I should treat them differently because they’re a part of a generation.
Alain Benzaken: I really try to look at people individually. Yes, there are some Gen X people that do have certain tendencies but in the end, I think it goes deeper than that. I think more understanding, like I said, what they want to achieve in their career and how to help them succeed.
Alain Benzaken: Some people want to succeed because they’re competitive, some people want to succeed they want to prove it to their parents, who knows. Some people wants to succeed because people most people want to succeed.
Alain Benzaken: So you just have to understand people at a more elemental level than just part of a generation. So I’ve never really had challenges so much on that. I’ve tried to say current.
Alain Benzaken: In this industry, it’s a very young industry so it’s important to stay current with the trends and so forth. So I feel like I need to adapt more to that than anything else and that’s kind of what I work on more than anything.
Alain Benzaken: So I’ve had challenges in a bunch of different companies. I always call the biggest challenges as the Super Bowl challenges because literally, a couple of companies this happened to, I had to keep a site up during the Super Bowl. When they were advertising our company in the Super Bowl and literally we would have Super Bowl traffic coming to our website.
Alain Benzaken: And so, those are really hard challenges because you can manage scale and growth at a steady level but when you get these incredible spikes of traffic, that’s when it becomes a challenge. That’s usually when your systems break down because it’s hard to test for and it’s hard to anticipate.
Alain Benzaken: And so I had that a couple times and we had to plan for months ahead of time. One was at TheLadders when we did a commercial and we really got to keep the site up and Taco Bell was down for, like, 6 days.
Alain Benzaken: And the other was by the Buddy Media when we had huge spikes we had brand advertisers advertising on Super Bowl, go to our Facebook page, and we were hosting the page.
Alain Benzaken: And so, those are the challenges. So I call those the Super Bowl challenges and they’ve happened a bunch of times. But in the long run, I’ll tell you that in terms of the scale and growth, again and again, the challenge has always been more on the people side.
Alain Benzaken: If you hire really, really good technologists who know architecture and know how to build things correctly and you challenge them and you make sure they build it correctly…
Alain Benzaken: The technology is like math. And so, if you do the math and you know this is where we are, this is where we need to be, and this is the scale we’re going to hit, you could usually solve the problem.
Alain Benzaken: But people are not math and so handling the growth of people and managing everything that goes on when your company is doubling in size, at Priceline, we’re doubling every month.
Alain Benzaken: So just handling that growth and hiring people who can manage maybe one person now, maybe ten people within three months, and then becoming a VP in a year. And so, you got to really, really get the right people in the right position and that’s more of a challenge overall, I think.
Alain Benzaken: And it’s the biggest challenge in technology in general where technology managers are hard to find. Really good technology managers are hard to find so that’s probably been more of a challenge on the scaling side than the technology itself.
Alain Benzaken: I think in the West Coast they’re much more open to fail fast and move on. On East Coast, they’re still, even today, is a “Let’s push it through, let’s make it happen.” And I’m like, “Either we’re going to make it or we’re not going to make it, and let’s find out earlier and let’s move on.”
Alain Benzaken: So what I learned was a couple of things from now on, I will say, is one: executive teams matter incredibly. And I’ve been on some very successful ones and it’s just easy. The success comes quickly and if things don’t work, you change into that.
Alain Benzaken: And two, that was also a problem of timing as well. I think there’s recently an article about startups, what’s the biggest indicator of success or failure in startups.
Alain Benzaken: And it turns out timing is important. If you get in too early, even before Priceline I was at Prodigy, which was one of the first online services. This was pre-internet.
Alain Benzaken: We were way too early and then AOL came and had, not necessarily better service but they had better marketing and eventually beat us. So that’s probably a bunch of learnings I’ve had over the years: timing, executive team, and your points of marketing.
Alain Benzaken: I had a really good mentor when I was at Priceline, he was an executive who’s CTO. It’s very hard in technology to sort of stay in touch with the code and stand the code while also managing and understanding the business side of stuff.
Alain Benzaken: Because when you’re in the code and you see the challenge, it’s easy. But when you stop coding, it becomes a little hard and you don’t know exactly what’s going on, you’re really relying on your team to give you the information that you need because you kind of start to lose touch with the technology.
Alain Benzaken: So it’s important to have a sense, and this is what he was really good at and that’s what I learned more than anything else from him, a sense of where to know where the soft spots are in any sort of project or any big endeavor that you’re working on with your team.
Alain Benzaken: It was a skill that, I won’t say it’s black science but it was a skill that he had where he would like, “I bring the big project plan on that, everything is good.” And he’d be like, “How are you going to do this one thing?”
Alain Benzaken: It would always be the one thing that was like, “God damn it, I don’t really know how I’m going to do that.” And that’s a skill that I’ve worked really hard at achieving.
Alain Benzaken: Some of the stuff, you know it’s going to get done, you know it’s going to get done but in any project and any situation, there’s always one thing that they don’t want to tell you is the part they haven’t quite figured out yet.
Alain Benzaken: And so, that’s a skill that you learn over time and I’ve been lucky enough to work with some important mentors. And I’ve seen that in different areas, not just in technology, I saw it in finance. Same thing at Priceline we had a guy that would point at rooms of spreadsheets and would point point at one number and go, “How are you going to get to that number?” And make people squirm every time. It was unbelievable, I never saw anything like it.
Alain Benzaken: And that’s a skill you gain over time, that’s experience. So that’s important to me. I think mentorship in general is important because it helps you achieve faster, basically.
Alain Benzaken: Working with someone who’s already been there, who’s already done that. As you know, we do triathlon training and having mentors in sports, actually growing up, although I was a pretty good athlete but I didn’t train very effectively. And I was okay, I was average.
Alain Benzaken: But I really learned the importance of mentors in terms of getting you to where you need to be faster. And it’s really just like a shortcut and so when you have them, you have to take advantage of them.
Alain Benzaken: So it’s a great importance so I try to be a mentor to my technology leaders as well but I’m still learning from a lot about this.
Alain Benzaken: I’m having this situation now in my current company where every day we have a status report on how things are going. And every day, I hear an excuse about why things didn’t work exactly the way they should have.
Alain Benzaken: And the excuses are all good and it hit me this morning, I don’t actually want to hear an excuse ever again because an excuse is really a reason for not doing something earlier. So at the end of the day, something didn’t work and the next they’ll say is, “Well it didn’t work because X, Y, and Z happened.” And that’s just not valid. You have to be much more proactive, you have to communicate upfront about what the problems are and then we’ll resolve them.
Alain Benzaken: I always tell my team, for example, “I just want to hear the bad news.” That’s my management mantra number one. As long as you tell me the bad news, I won’t get upset, we’ll deal with the problem, and we’ll move on.
Alain Benzaken: That’s just screwing up every day, that’s a whole other story. We’ll deal with that but as long as I hear the bad news, I can do something about it. That’s the reason I’m here.
Alain Benzaken: But don’t come to me three weeks late and say, “Hey, Alain something screwed up last week and I didn’t tell you about it.” And you might have a good excuse about why it happened but I don’t want to hear about it.
Alain Benzaken: So the executive level, it’s really about being open, transparent. Communicating is really number one thing and working well together. And if things don’t go well in your area, I want to hear about it and I can help you, and so forth.
Alain Benzaken: There’s just so many, so many unbelievable new technologies that are coming up in all the areas. The internet is one thing and sort of like the groundwork but that’s easy stuff.
Alain Benzaken: I’m currently working actually in the garment industry which is still running in backwoods mode and some of the technologies that we can apply there and some of the things we could do would just be some, which is still unbelievable. Basically to be able to design your own clothes and print them right there, just simple stuff like that.
Alain Benzaken: But there’s just so many new technologies coming up. It’s kind of exponential. The way technology works is it kind of grows but then it grows on top of stuff that’s been invented before and so we’re still reaching the early stages of the exponential current and what can be done.
Alain Benzaken: So I think in biology, there’s some unbelievable stuff going on, obviously in tech. So I’m excited, it’s all fun.
Alain Benzaken: It’s important for me to be an example to my kids, to be successful at that level. I mean, I’m very, very competitive. I like doing it in sports, I like doing it in any situation I’m in. But in the end, I have a very close family. I want to be successful and I want them to be successful.
Alain Benzaken: So I don’t know if it’s a driving cause, I think it’s more that you enjoy life as well and have a good time and laugh. It’s funny. I don’t live life with a super, super important cause sort of hanging out there. I’m a little more day to day and enjoy things.