From Aspiring Architect to Engineer and the Importance of Being Yourself
Today we are proud to present an in-depth interview with Dana Underwood, an accomplished executive, entrepreneur, and photographer. Dana has a very inspiring story about how he discovered engineering as a career path and how he has grown in his career as a product manager. He has many great insights about what it takes to succeed in product management and how to make your passion your profession.
How did you get into the world of technology?
In high school, I transitioned from an aspiring architect to an aspiring engineer. I thought I wanted to teach, but being in Silicon Valley for grad school in the late 90’s convinced me that there were far more exciting things to learn by jumping into the workplace. So after earning a BS and an MS in Mechanical Engineering, I began my career as an electromechanical engineer. Four years later, the bubble had burst and I was a little frustrated with always being on the receiving end of decisions made by company leadership. I wanted to, at the very least, weigh in. I chose business school as a way begin that transition.
My post-MBA career began with sales and marketing roles at Genentech. There have been lots of twists and turns, but product management is where I’ve thrived. The fluency challenge extends from high-level strategy to every detail of implementation. I dig that.
Who has been your most important professional mentor and why?
Dean Alford has been my most important mentor. Two years out of business school, I was at Genentech and my career was going well. I had taken on a number of extra initiatives during a sales rotation and, as a result, gained a tremendous amount of credibility. Suddenly, though, I found myself in a new role, under a new manager who did not seem interested in my development, in helping me maintain my relationships with the rest of the team, or in being an effective manager of people in general. My instinct was to get the hell out.
Until then, the largest company I had worked for had 45 people. I didn’t know how to gracefully manage my way out of a bad situation in a highly politicized environment, other than to just quit. Enter Dean, the head of sales operations for my franchise. First and foremost, Dean was a listener when I needed one. I blew off steam in his office. And I did so often. But after listening to me vent, Dean coached me on what it took to create opportunities within an organization like Genentech. He shared with me some personal stories about what he’d learned about sticking things out. But most importantly, he offered his counsel without judgment. I always got the sense that Dean was a friend before he was a formal mentor. That meant a lot to me.
In the end, upon his promotion, I ended up backfilling Dean’s role in sales operations. That was, by far, my favorite role at the company.
There have been a number of experiences in my life that have chipped away at my notion of impossibility by challenging it. Up against the frustration I was feeling, I couldn’t imagine a way to work through it while remaining at the company. Dean was the sounding board and (very importantly) the advocate I needed to help me see another way. Even today, I try to keep those lessons close.
What has been the most meaningful professional experience you’ve had and why?
I always say that fear is too great a motivator for me. I know that I’ve let it make decisions for me before, personally and professionally. The professional experience that has been the most meaningful is the one that required overcoming the most fear: quitting my job and founding a startup. In 2011, I left my job as product manger for a $700k DNA sequencing instrument to found a startup with Tony Deifell. The first catch: we didn’t know what we were going to do.
Innovation Endeavors had taken a risk on Tony and me, and we spent 6 months researching our focus area: gift giving. That process gave birth to what is known today as AwesomeBox. The way that I describe the time building that company is always the same: “it was the most worthwhile, rewarding, and awful thing I’ve ever done.” One reason why its most meaningful to me was because managing my fears required daily effort. And, while building a company, there is more than enough fear to go around.
Another unanticipated benefit was how much I was able to learn about myself. Having a cofounder really helped with this, because it is, in some ways, much easier to lie to yourself than the person with whom you spend 18 hours each day. I thought I understood a thing or two about vulnerability and being exposed, but being a cofounder helped show me how much more I have to learn.
I thought I understood a thing or two about vulnerability and being exposed, but being a cofounder helped show me how much more I have to learn.
What is the most difficult professional or personal challenge you’ve had to overcome?
Hmm. This is a tough one, but mostly because its so easy to answer. The biggest challenge I’ve faced has been on the personal side. It has been being able to let people know me. That sounds a bit fuzzy, so let me try to explain. For much of my life, I have prioritized making sure I was perceived favorably over being respected for all of who I actually am. In the professional context, that isn’t so devastating, because I think its fair to say that an arms-length understanding of your colleagues is “normal.” However, carrying over that same walled-off posture to my personal life was eventually pretty emotionally debilitating.
At a particularly difficult time in 2008, I decided that what I needed most was to figure out how I could shed the fear of being known. In retrospect, that’s a convoluted way of saying that I needed to begin a process of learning to accept all sides of who I am (both good and bad). I really didn’t have that kind of vulnerability in me, so I took a very brute force approach by combining a passion of mine (photography) with daily, public journal entries. For 365 consecutive days, I practiced photography and disclosure, posting one image per day with some thoughts based on the day. Photography was the carrot and writing something that was hard to share was the stick.
By the end of a year, a couple of things had happened. First, I was much more able to talk openly with anyone about things I had been terrified to discuss before. That exercise is what makes it possible to answer this question with any sort of honesty. Second, and completely unanticipated, I got a LOT better at photography, and I didn’t even realize it was happening until the very last month of the exercise.
I needed to begin a process of learning to accept all sides of who I am (both good and bad).
Whether you want to be a photographer, an entrepreneur, or a trumpet player — there is somebody who is closer to that goal than you are. Try to find those people to understand the path to that goal and the reality of what it’s like once you attain it.
What advice do you have for young people of color who are looking to get into technology?
Growing up, I was very privileged to have parents who invested heavily in my education; so, as a “bookish” kid, I didn’t feel like a fish out of water at school. I did feel a little more of that at home, because not all the kids I grew up around had those same educational opportunities, including most of the kids in my extended family. So sometimes I did feel a little different outside of school. Today’s young people of color cannot let that deter them. Pursue your curiosity. Don’t walk away from it. Technology, although still out of reach for many, has never been more accessible. I see that trend continuing. Chase the answers to your questions, and don’t be afraid to be seen as different.
Whether you want to be a photographer, an entrepreneur, or a trumpet player — there is somebody who is closer to that goal than you are. Try to find those people to understand the path to that goal and the reality of what it’s like once you attain it. Success stories receive most of the focus in our culture, but they don’t often tell the stories of the struggle in enough detail. Or at all. Getting closer to the those who are close to where you’d like to be is a worthwhile part of the exploration process.
You started your career in biotech / life sciences and made the transition to the world of the Internet. What motivated you to make that transition?
Early in my career, what attracted me to biotech was two things. Because I’d never taken a biology class in my life, I knew that I would always be learning. I was also inspired by the persistence of scientists who went to work every day on a problem, without the promise of fulfilling their dream of finding the discovery that would improve humankind forever. In my world of mechatronics, you knew right away whether your robot was working, but I was fascinated by the dedication of scientists working hard to find cures for cancer or infectious diseases.
After a few years in biotech, I did feel a bit frustrated by the uncertainty and the long timelines. Even at a wildly successful place like Genentech, the drug development process can typically take a decade. I definitely missed being able to conceive of, plan, and build something that worked within a few weeks.
At the same time, I was spending more and more of my time on photography. The internet was inextricably linked to perfecting, promoting, and sharing my art. I wanted to make my passion a lifestyle choice.
Photography has been a passion of yours for some time. How did you decide to pursue your love of photography as part of your professional path?
This is the part I call “make your passion a lifestyle choice.”
I always knew I wanted to go back to smaller companies. So I actually chose to leave Genentech while things were still great, and it was under the best circumstances I could have imagined. I joined a photography technology startup called Lytro (then called Refocus Imaging). I was the 4th team member. It was an opportunity to fuse my passion for photography, my technical background, and my business background. I believed their technology would fundamentally change the photography industry. Ren, the founder, is brilliant technically; he was great with the community and with investors. But we had very, very different styles. I didn’t stay there long.
I didn’t plan to take nearly a year off, but photography took over. I chose to feed that passion 100%. Making my passion a lifestyle choice included setting up a website to become very intentional about my photo sharing. It included carrying around a huge DSLR everywhere I went and taking pictures of friends, even when they sometimes didn’t want me to. By July, I was asked to do a shoot at a political fundraiser. I did it for free and photographed Kamala Harris, among others. My second professional shoot was on August 17, 2008, and it was with Barack Obama. That was the day that I decided that I should start charging for my photography, and I have made part of my living as a photographer ever since.
Finally, making my passion a lifestyle choice includes finding a job at CreativeLive, one of the best online resources I found as I worked to improve as a photographer. I now help build the product that people just a few years behind me will use to become great artists in their own right. Being able to work on something that I believe in so thoroughly fills me with gratitude and is a huge source of motivation.
What tips would you offer someone looking to get started in product management?
I have one high-level tip and one more tactical one, though they are related.
I really believe that being a great product manager includes being able to speak many languages. The languages of the executive team, the design team, the development team, and (most importantly) the language of the customer. Listening is a terribly underrated and underutilized skill. Listen for *why*. Don’t listen for what. Understanding underlying motivations will get you very far as a product manager (and in life). Being able to fluently communicate with groups having different goals lets you stay exactly where you need to be: at the intersection of those groups, considering all the trade-offs, and making the right decisions.
My second tip is make a product. It doesn’t matter what. Paper airplanes, glass blown bowls, new board game, an app (or even drawings or mockups of any of those). Pick anything to build, but make sure you do a few things along the way:
- Ask people whether what you’re building is something they want. Does it solve a problem? Provide some value?
- Make prototypes of as many ideas as you can. Lots of them. Again, they can be as simple as paper drawings. If you get attached to them emotionally, you’ve spent too much time on them.
- Based on the prototypes, ask people if they want what you’re building BEFORE you build it. Make tweaks based on this feedback.
- Go up to strangers along the way to get feedback. This one is really difficult, but, trust me, you will learn more than you ever imagined if you push through this exercise. It never fails. As Tony and I were building AwesomeBox, we made a regular practice of stopping people on the street in San Francisco to get feedback on our prototypes (which ranged from pencil sketches to Balsamiq mockups to iPad prototypes) and videotaped those conversations. Make tweaks based on the feedback.
Listening is a terribly underrated and underutilized skill. Listen for *why*. Don’t listen for what. Understanding underlying motivations will get you very far as a product manager (and in life).