Alper Özöner
University of Groningen
Groningen (53.2° N, 6.5° E)

featuring JD Leonard, Founder & Chief Solutions Architect, Modern Biz Consulting, New York City (40.7° N, 74.0° W)

I had a great time interviewing JD Leonard. He is an entrepreneur, web development consultant, and a project manager who currently leads a project called Copperly, a new concept that provides merchant services to businesses. From the moment I took a glance at JD’s LinkedIn profile, the aspect of his career that interested me the most was that he worked in a diverse range of positions. His career path is a very interesting one, as he has mainly worked in e-commerce, web development, and consulting. Thanks to his openness, our interview followed a natural path going through topics we each found interesting, including his personal development, what decisions shaped his career, and the philosophy of his work.

We started our interview with JD’s background. He mentioned that growing up in London and living there until his college years gave him a unique perspective of life in Europe as an American. As a child, he quickly figured out what he didn’t want to be when he grew up—an investment banker like his father, since investment bankers work long hours away from their family. JD started designing websites as a hobby when he was in fourth grade. He didn’t have a concrete idea what he wanted to be then, but it was clear that he enjoyed “computing,” in his own words. He says he picks opportunities as they come to him and that he doesn’t “get too attached to future me.”

This unique mindset shows itself in the choices that ultimately shaped his career. Starting with web development, he was introduced to the world of e-commerce and marketing through networking that naturally came with his computer skills. One interesting turning point in JD’s career was when he received an unexpected response from Microsoft to his application for a software engineer position: they wanted to interview him as a program manager instead. JD believes that his social skills, along with the soft skills in communication and management developed further at Microsoft and helped him to transition to full-time consulting. He underlines the importance of soft skills by saying the factor that differentiates him from others in consulting is that his clients are comfortable speaking with him, and he is good at “communicating complex concepts to people in a way that they can understand.”

When JD left Microsoft after two years to pursue his entrepreneurial drive, his first big step was building a website called Textbook Madness, where students could reach many alternative ways of acquiring textbooks in order to save money. JD reflects back to this as a valuable experience despite considering it a failure. He says, “you can learn a lot from failure,” and from this experience, he learned he was “not a great salesperson” but he also learned much about the bureaucracy and logistics of setting up a company, which helped him in his later projects. JD believes that it is very important for web development students to dedicate the time to teach themselves and learn on their own by finding client projects where they can make mistakes and learn.

I was struck by JD’s laid-back attitude about his career and his thoughts on work-life balance. For him, his family and his well-being come first. He is open to take breaks for family phone calls, and he allows minor distractions in his home office, such as his cat, Oliver. This was something I didn’t have in mind when I thought about an entrepreneur, but it all comes down to being relaxed and happy rather than being stressed and sad. In the end, efficiency isn’t everything. Another aspect of JD’s career that captured my attention is that it has not been shaped by predetermined long term goals; instead, he has embraced new things as they have come. From starting in program management to his expertise in Drupal (a content management system), he went with what felt natural and did his best on every project he worked on, even though sometimes it meant stumbling or discovering shortcomings. Last, but not least, I think that his decision to leave Microsoft required a certain amount of courage and elevated his career to what it is today. His transition into a “solo-preneur” (an entrepreneur of “size one”) was a product of self-awareness of his skills and a willingness to change.

I think the biggest lesson for me from JD is being good at something is certainly a prerequisite for professional success, but if you are willing to take risks, people may come to you and can open up new doors for invaluable experiences. Embrace your skills, and if you don’t know what they are, take action anyway; by doing, you will eventually learn more about yourself and what you should be doing.

Highlights from the Interview

You started off in web development early, got your first job at Microsoft, then went into freelance consulting. Is there a story to that?

I started making websites just for fun, teaching myself how to make websites in fourth or fifth grade. A long time ago. That was one of my extracurricular activities. Learning to code and hang around that stuff. I have always found that fun, and I never parted ways with that too much since fifth grade. The program management work I did at Microsoft was something that just kind of came in a sequence of events. When I was at Rice University studying computer science, trying to look for a job, a lot of students applied to big tech companies. They recruited on campus. I applied at Microsoft as a software development engineer, and they came back to me, and they said Nope! We don’t want you as a software development engineer, but we are interested in interviewing you as a program manager. I didn’t know what a program manager was. They told me what that was, and I said that sounds kind of interesting. So that certainly diversified my field of experience and knowledge beyond just software development. Certainly, it caused me to be more well-rounded and led me to do some of the freelance consulting that I’ve been doing mostly full time now since 2013.

Could you give a brief overview of the working environment at Microsoft in your first professional job?

As a program manager coming out of a bachelor’s degree at a university, it’s kind of an entry-level position at the company, in an engineering field. At Microsoft there are kind of three key engineering roles and they all work closely together. In addition to program managers, there are also software developers and testers. And so these three roles all work together on the same project, on the same applications. The job of the program manager is to shepherd the project along, deal with a lot of miscellanea, a lot of overhead, a lot of communication, also planning. I think what Microsoft saw in me, perhaps, was not the strongest developer but someone who could work very well with developers, know the language, and somebody who had more of the soft skills than a stereotypical developer.

Could you give a brief example of what you did after Microsoft as a consultant?

I was a one-man shop doing web development consulting, so I focused on complex web application development—and the soft skills are super important in that kind of role. I did a lot of interaction with clients because there isn’t anyone else in the company to do that. You wear all the hats. I think there are a lot of developers out there who find it much more difficult to go into a freelance consulting role because perhaps they don’t have some of the soft skills, and those are a little harder to acquire through self-teaching, whereas learning to program is something that most people could attain through self-teaching. So certainly I lucked out there. The soft skills are something that happened; it’s not really something I planned for. And it definitely paid dividends. Being able to talk with clients and have them be comfortable speaking with you and interacting with you is super important. A lot of clients have had bad experiences with communication with freelancers or consultants, especially in the tech world. So being able to differentiate yourself that way is super helpful.

What does your current work entail? What sort of skills do you use, other than your soft skills and personal skills?

I specialize in Drupal. Drupal is a content management system (CMS) or content management framework. You’ve probably heard of WordPress. WordPress is the most popular CMS out there, and Drupal is the third most popular by market share. Drupal is enterprise-grade software for developing websites or web applications. It can be used for very simple or very complex websites. There are a ton of really popular websites out there that run Drupal, things like Whitehouse.gov (previously), NBCUniversal uses Drupal for virtually all of their websites, Sony BMG—including various music artist websites—and Economist.com. My niche is focusing on complex web application development. I just kind of made up that phrase, but the idea is that I don’t work with small businesses that just want to tell you about their business. I take on development of complex web applications. It’s super important to differentiate yourself because somebody who is coming to you for your type of services can’t just go to any other developer to have the same work done.

Are there challenges to remaining productive in your work?

Yes, it certainly can be tough as an entrepreneur and somebody who is self-employed and self-directed. There’s always some distraction or something that can keep you away from your work. I’ve been working from home since 2013. Working from home is a challenge, but it’s also a tremendous benefit. A lot of people have trouble with that. A lot of people find that working in a library or cafe works well for them. For me, I find that to be worse and kind of more distracting.

Is working from home making you more productive?

I absolutely make a lot of decisions that shy away from productivity for other things. Whether it’s flexibility, spending time with family, relaxing, whatever it is, I’ve come to a point of realization in life where there’s only so much money that one needs to be happy in life, and once you have those needs met, I’m not so motivated to, you know, try to hit it big. It kind of contradicts the stereotypical image of an entrepreneur.

I gave a talk for my university recently where I talked about being a “solo-preneur.” An entrepreneur of size one. And I talk a lot about the work-life balance and the ability, if you can, to get in the right mindset of really being much more relaxed and happy—and being able to provide that for your family and friends as well by being flexible. If my wife wants to call me whenever and talk about something, I’m always available. Unless I’ve got a client call or something like that. There are these little things that nobody ever thinks about, nobody plans for, but having had that now for so long, I know I would never go back to a real job. Full-time employment. There’s just too much to benefit from.

Do you have any recommendations for a student starting off studying at university right now?

I’m not sure if you’ve heard of the book The 4-Hour Workweek. So this book is very idealistic, the title is meant to sell copies. I read this book, you know, probably in 2011 or 2012. And it kind of changed my perspective on a lot of things in life. Work, life, retirement, money, all these things. I do recommend it to people, particularly if they’re interested in kind of planning for the long term. It talks a lot about setting long-term goals and how to plan to meet those goals. Especially in the context of maybe trying to reduce the amount of work you’re doing—from a traditional kind of forty-hour workweek down to something perhaps more desirable. That definitely affected me. As far as my planning, talk about long-term planning, I don’t do a ton of that. I let things come to me. I’m very flexible and adaptable.

Thinking about the future, how are science and technology reshaping the web development space?

There’s a lot of innovation. In many ways the web has been around in its current form for a long time, and all its innovations are kind of incremental. But I think you do see a trend towards more people using native apps on their phones or on their devices, and that bypasses the web browser and the kind of technical experience you get with a website. But at the same time, that is causing web developers to innovate and make the websites closer to mobile apps than they have been in the past. There are a lot of new technologies in modern web browsers that allow web applications—websites—to do things that previously you could only do in a native app on a phone. For example, in Google Chrome, the website might ask for your location on a map—that’s the kind of thing you could only do with a mobile app. There are other things having to do with push notifications, which is something that you’re kind of familiar with now using phones, but that’s becoming more common with websites now. So I think there’s going to be a kind of continued merging of capabilities, or sets of capabilities, between mobile apps and websites.

(Interview excerpts have been lightly edited for clarity and readability and approved by the interviewee.)