An Interview With Dana
On my computer screen is a small profile picture of a face and the words “Dana Wensberg is in this call.” As usual, he’s precisely on time.
Dana and I met while working at Paperless Parts, a small startup working to build software to solve problems in the manufacturing industry. I was an intern, and at the time he was a full-time engineer. He was the very first person I met at the company, during a virtual career fair. In the span of just ten minutes, he gave me a live demo of the product, used the word “jazzed,” and gave vigorous rubs to both of the office dogs. I knew immediately I wanted to work with him.
His desk used to be right behind me, facing the opposite wall. It was commonplace to, every few hours, hear a profanity loudly exclaimed from his vicinity. After a while my shock gave way, and I learned to love his enthusiasm. It’s been over a year since my internship ended, and we’ve taken to calling almost every month to catch up and update each other on our lives, both professionally and otherwise. Aside from my mom, he’s my biggest cheerleader.
I click the big blue button to join the online meeting, and hear the “entering call” Google Meet sound. The first thing I see is Dana’s huge grin. “Heeeyy!” he says. He’s in his office at work. The walls are the company shade of orange. He’s wearing a button-down and a baseball cap, and there are a few more baseball caps hanging above a whiteboard behind him. On the board he’s written “no excuses, leverage tenacity” so that it will show up on his video calls.
Dana leans forward, elbows on knees, rubbing his hands together. “Ok, tell me what I’m in for today.” Meetings with Dana always have purpose. I tell him that today’s purpose is for me to learn more about him. I begin the questioning.
Do you like being a product manager?
He laughs. “Yeah I think it’s a lot of fun.”
What do you enjoy about the day-to-day?
His eyes fixate on various objects around the room as he thinks of the right words to combine many months of experiences into one answer. It doesn’t take him long. “It’s a really dynamicposition. At times it can feel like babysitting and at times it can feel like you’re building the first rocket engine.” His face lights up when he mentions rockets. “Dynamic is the best word to use because you’re a lawyer, you’re an engineer, you’re a designer, you’re a diplomat, you’re a comedian, you’re a jester, you’re all of these things at once.” Each role is enumerated on a different finger.
Does it feel rewarding?
“It’s demanding, but it's really rewarding when you get it right. The days where I feel like I've been the most productive are when at the end of the day, everyone is on the same page and totally aligned on what we're getting after and what we're doing. More so than any other time where we'd shipped code or I've written a really good document.” These tangibles are recalled with ease – he’s had a lot of practice measuring performance. He dismisses them, pushing them to the side with the back of his hand. “None of that really matters. It's getting people excited about things. That's what’s exciting for me, and ultimately the major reason why I switched from being an engineer to being a PM.”
What do you think makes you good at being a product manager?
“I think I have a really high give-a-shit factor.” The words come matter-of-factly and without hesitation, like he’s answering a math question. Like there’s just one right answer. “And I think ultimately that is what is the most important quality in a PM, more so than anything else.” He leans forward, looking right at me. As if making a silent challenge: learn this lesson or be unsuccessful. Then on second thought, he shrugs, adding more. “That along with the fact that like I'm a decent talker and I can think on my feet. Me having a technology background and knowing the manufacturing problem space is honestly just a bonus. You don't really need to know that much to have a high impact quickly, as long as you understand how to navigate people.”
Has it been hard to learn those people skills coming from an engineering background?
“Yeah, definitely. I say this all the time, I'm not an eggshell guy. I've been told that my diplomacy has gotten better, but I'm not a very diplomatic person. I very much wear my heart on my sleeve. Yeah I mean it’s definitely hard.” An exhale of amazement. He seems to be reminiscing on past challenges. “It's been kind of a long time for me to get to the point where I feel confident in what I'm doing with the job.” His fingers betray his smile as he rubs his temples, alluding to a harsher struggle than he lets on. “The intangible is always hard because there isn't some test you can go take that tells you you're good at it. Because, you know, people are hard.”
You have been a mentor to me for over a year. Why do you do it?
A grin. “That’s a good question too.” This one catches him off guard. “I dunno, I mean, it's cool.” It’s as simple as that. “Watching people just go crush it is a lot of fun.” He starts another sentence and then cuts himself off. “–It's almost like a gentleman's bet.” He leans back in his swivel chair, moving both hands into the air to add emphasis to his words. “You're like, ‘I know this person's gonna be just wildly, out of her mind successful. I'm going to hitch my wagon to that trailer.’ I think we get excited about similar things. I just find it very rewarding to see you go be successful.” A shrug. “It's kind of hard to articulate why. I just like it when good things happen to good people.”
Who inspires you and why?
“Well, I'm a big Elon fanboy.” Controversial. “He just kind of gave the finger to everyone and just said ‘I'm going to do it my way and I'm going to do it better than anyone.’ And he did it.”
What areas do you think you need to improve in, both in terms of your current job as well as your career beyond?
A deep sigh. “I’ve really struggled as a company has gotten larger. I've been so used to everyone operating in similar ways to me, which is just be gritty, get it done, make it happen, we'll solve it right now on the call.” He uses his hands to emphasize each word, showing exactly how direct he means. “You just can't really do that as much when you get bigger. As for beyond … so honestly I want to be an entrepreneur. And being a PM is kind of just a precursor to doing that. I kind of like being a Jack of all trades. So to answer the question professionally, I don’t really know. I think if Paperless does well, I'm going to have a good career because being the first employee at a startup that wins is kind of your ticket. So that's really what I'm focused on, more so than anything else.”
What has being at Paperless taught you about creating your own company?
“Well, I mean, it’s taught me everything about that.” He doesn’t name any specifics. He doesn’t need to. This company didn’t add another few bricks to his existing desire to create his own company. It laid the foundation and then went along and built the whole house too. “As a product manager you only have so many chips. It’s like you’re playing poker on a smaller scale as to what you would as a CEO. It's not the same game but it has a lot of similarities.”
When you create your own company, what's the impact that you're hoping for?
“I want to do it because …” A long pause. “I couldn't imagine what my life would be like without Paperless.” Then he adds more quickly. “Not in like an overly dramatic sense, it's just been a part of me for a long time now.” It’s as if he’s talking about an old friend. “And I feel like I'm a pretty centralpersonality in how the company is developed. And I kind of trust myself to be able to like, create something similar to this. It's been wicked fun and amazing.” A shake of his head, as if he can’t believe it. “It doesn't feel like a job to me, and if I can get paid to do that, I think that would be a really good idea.” A laugh. Lucky guy. He leans back and adjusts his hat. “In terms of impact to the world, honestly, I think everyone has a responsibility to leave a place in a better state than they entered it. There are infinite ways to make that happen. And I don't have the next idea yet, but when it comes, I'll jump on it.”
You said that you don't know where you'd be without Paperless Parts. Do you think it's easy to pull yourself away from work? Do you feel like you have an identity outside of the company?
“Umm, I would say I do.” He says the last word without finality. “I just took my first vacation in a few years.” His eyes are on the lower part of the wall to the side. “So I mean, a lot of people would disagree with that, but I think I do.” This time he sounds more sure. He narrows his eyes. “And also I get, I don't know if flack is the right word, but the whole work-life balance conversation’s obviously really hot right now with COVID and stuff. And, you know, there's definitely a lot of blurred lines for me.” Then he shrugs. He knows who he is. “But you know, I'm 26. Like what the hell else am I going to do? I love what I do. It brings me immense joy. So, I don't think it's a bad thing that I work a lot. There are many other things in life that bring me joy and I go do those too. So I think to that end, well, I'm definitely pretty far on the work heavy side of the work-life balance spectrum. I think I've got as healthy a life as any person could ever ask for. So I'm very grateful for that, and I think I'm doing okay.” End of question.
I inform him that I’m all out of questions, and he offers his future assistance in the case that I think of any more. “You’ll see it when I’m done!” I tell him, in regard to the piece of writing that this interview is research for. “I’m excited. You’re gonna crush it.” In true Dana fashion, he’s rooting for me.