C-suite career advice: Michael Rodriguez, DreamHost

What are some common misconceptions about working in IT? "You'll often hear that "A formal education isn't important" - but it is very helpful."

Name: Michael Rodriguez

Company: DreamHost

Job Title: CEO

Location: Brea, California

Michael Rodriguez brings senior leadership experience as the founder and CEO of DreamHost. After meeting classmates who became his business partners at DreamHost in the mid-90s, he has spent the last 23 years growing DreamHost into a leader in software and product development whose output includes a managed application platform that helps customers leverage open source software such as WordPress. Before founding DreamHost, he started his career as a programmer for a local business.


What was the most valuable piece of career advice that you received? From an early age I was captivated by computers. It was just playing around at first, but became a more serious interest over time. My high school physics teacher encouraged me to expand my thinking around possible applications of computers.

I knew what I loved. But I had to figure out how to funnel that love and that interest into something useful. While it wasn't strictly advice, that one simple question of "But computers to do what?" set me down a new path: Try to do something that is useful to people. Don't just chase success. Think about what you want and what drives you.  Find meaning in your passions and dig deeper there.

What was the worst piece of business advice that you received? In grade school, I knew that I wanted to be a businessman - before I really understood computers and their potential. In those early years I remember taking a career aptitude test (We've all taken them - multiple choice tests to gauge your personality and interests) and at the end you're given career advice.  At that age those tests don't mean a lot, but the results stand out in my memory. I learn and operate best when I have lots of information on-hand to inform my decisions.  As a result, the test determined that I was risk averse and strongly recommended that I avoid a career in business.

Better advice would have been to suggest I learn how to apply a high information learning style as a strength. Business isn't primarily about taking bold unnecessary risks, but rather about understanding risk and learning to mitigate it while balancing the risk against potential rewards.  

What advice would you give to someone starting their career in IT? No matter how much experience you may have, no matter how long you've been in the workforce or in school, strive to make learning an integral part of your daily process. Carve out as much time as you can to learn new technologies and new processes. This industry moves and changes so quickly that ignoring trends means you risk getting left behind. Embrace change and be open to learning new ideas from each person you work with.

Did you always want to work in IT? I saw this screen way too much growing up and I took it as a challenge.  Man vs. machine!

But seriously, yes. I've loved using computers from an early age, and once I hit high school I knew I wanted to use them professionally.

I did consider other careers in science and engineering or law. Math, logic and computers all represented smart, analytical approaches to problems and I knew I wanted to work with those.

What was your first job in IT? I started out as a programmer at a small educational software company. They made school management software and I was doing database application programming.  I remember having to program in FoxPro which was a painful programming environment. There is nothing worse than dealing with a buggy underlying platform when trying to solve a problem.

What are some common misconceptions about working in IT? You'll often hear that "A formal education isn't important" - but it is very helpful. You'll want the experience and the structure of an organised educational programme to help you understand the theoretical underpinnings of computer science. With a thorough understanding of the fundamentals, you'll be able to apply your knowledge across a wide range of computer languages and applications. The amount of open courseware available has widened the opportunity considerably.

Trends in programming and business software can change within a matter of weeks. Being able to adapt quickly and tap into a strong foundational skill set is key to your success - no matter what you do in IT.

What tips would you give to someone aiming for a c-level position? We've never put an emphasis on titles at DreamHost, but they can be helpful progress markers. To anyone seeking a role at the c-level, I would strongly recommend that you study leadership as a discipline. At DreamHost we've chosen to embrace the concept of Tribal Leadership, detailed in CultureSync's book of the same name. It has provided us with a framework that helps us measure the health of our organisation and lays out clear growth paths. (It's worth noting that there are dozens of proven leadership methodologies out there, and Tribal Leadership is one that's worked well with our unique culture.)

Strive to do something meaningful and learn to align your organisation around the values and goals that precipitate from that.

What are your career ambitions and have you reached them yet? The ultimate goal for me is to help our customers find success. That takes time and a lot of thought, but it gives me a tremendous amount of satisfaction to hear their success stories. Personally, I've achieved my early ambitions. I've hit many milestones. I've helped to build a company that continues to be successful. I've seen many employees, past and present, grow and flourish. I'm enjoying the journey but I don't feel done. 

Do you have a good work life balance in your current role? When you're running a business there's a tendency to funnel all of your energy into it. It's important to give that same focus to the important people in your life. The time that you take away from work is really about recharging your batteries. You'll need energy and strength to accomplish your professional goals, and that personal time is really an investment in yourself.

Like everyone, I'm constantly trying to find that balance  Currently the balance is working and I have been investing a lot of my free time in becoming a better musician.

What, if anything, would you change about the route your career path has taken? When you have several business partners (there were four of us at DreamHost) there's a feeling that you don't necessarily need to seek out mentors. The four of us all had specialised talents and enough trust to bounce ideas off each other. That approach can have benefits, but can also lead to an echo chamber effect.

Knowing what I know today, I would have likely sought out some professional mentorship in our early days. We managed to figure things out on our own, but if we'd had external expertise to rely on from someone that had grown businesses in the past, some things could have gone a lot easier for us.

Which would you recommend: A coding bootcamp or a computer science degree? I would favour a computer science degree. A formal education can help you understand the theory of generalised problem solving. A coding bootcamp can be helpful as well, but most importantly I would start with whatever you are motivated to do.

How important are specific certifications? Certifications are a great way to signal to employers specific skills that you may have. They can be a structured, consistent indicator of skill level. Certifications can also demonstrate that a job applicant has the initiative, the discipline, and the drive to further their own skill set. We don't look for specific certifications when evaluating applicants for roles - but we appreciate those that are applicable and they do play some part in our hiring decisions.

What are the three skills or abilities you look for in prospective candidates? Problem solving ability. Self-starters and self-motivated people. People with follow-through and the ability to sell an idea.

What would put you off a candidate? If you don't find joy in helping customers find success, then you immediately become less interesting as a potential hire. Everything that we do is focused around our customers and helping them achieve their goals. If that piece is missing, the whole puzzle breaks down.

"That's not my job" is also a big turn-off. Rigidly staying in your lane and showing reluctance to go outside of a job description to learn new things and better yourself is also a red flag. Life is learning, and as soon as you throw up roadblocks to that process you're interfering with your own professional growth and the growth of whatever organisation you choose to work with.

What are the most common mistakes made by candidates in an interview? How can those mistakes be avoided? We specifically tell interviewees to dress casually, and many will still show up in formal business clothes. There's a detail we never miss: "Too much cologne" is a long-running inside joke of ours.

A lot of candidates don't do their homework about the company they are interviewing with. It's not hard to spend some time doing research before you come in for an interview. You will be spending a lot of time at a job, so make sure you find meaning in what they are working on. Read up on their values and look for a good fit.

Above all else, we want prospects to be honest with us about their capabilities. We'd prefer that they come in and share their strengths, weaknesses and areas of expertise - then let us determine whether or not they'd be a good fit for a given role. Misrepresenting a skill level puts the relationship on an unstable foundation from the outset.

Do you think it is better to have technical or business skills - or a mix of both? Our focus here is on problem solving, and everyone's workplace challenges are different. Some may be better off with hard technical skills, and some may be better served by a deeper understanding of well-performing businesses.

You should be able to learn things quickly to solve problems. Those problems can be technical. There can be people problems. There can be optimisation problems. I always encourage people to get involved whatever their role, and whatever the challenge. "Always be willing to fill the gap."