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Avvo web development director Justin Weiss.

Avvo software development director Justin Weiss still remembers the days when the legal advice company — where he’s worked for the past eight years — still had that new startup smell.

That was back before the company saw its headcount double to 300 workers in a single year, and before it fueled its next phase of growth with a $71.5 million investment, raised in July at a reported valuation of $650 million.

practicing-rails-large“When I started, it was a real startup environment: everybody pitched in, sometimes with developers making design decisions or marketing calls,” Weiss said of joining the company the same year it was founded in 2007.

Now, he oversees 24 web developers spread across eight different teams.

But Avvo isn’t the only thing that’s changing with age. Weiss says he’s the kind of person who always needs a side project. He spent his off hours growing up studying 1980s computer magazines and writing cheats for video games he played throughout high school.

“Now, at home, I’m much more focused on playing around with my wife and two kids, a three-and-a-half year old and a five-month old,” Weiss said. “A new kind of programming!”

That didn’t stop him from taking a deep dive into the Ruby on Rails web development framework, going so far as to release an e-book on the subject.

Meet our new Geek of the Week, and continue reading for his answers to our questionnaire.

What do you do, and why do you do it? “I love working in software development, it’s like getting to solve puzzles for a living. You see this problem, and you’re here, but you want to be there. It motivates you to keep going and find a way to get from here to there. Along the way, you may run into a bug, and you just can’t let it go. You persevere all day or all night and keep trying new solutions to the problem until you solve it. I have the maturity now to know that it’s usually better to set it aside and come to work ‘fresh,’ but the energy of problem-solving never goes away.

From the management perspective, some of the core ideas are the same, but people and company problems are much more complicated. In programming, we have really tight feedback loops. We can see the direct impact of our actions right away, allowing you to easily know what’s working and what isn’t working. If you make a change as a manager, though, it could take years to know if you made a good decision, if you can even figure it out at all.”

What’s the single most important thing people should know about your field? “If you have the knack for problem solving – the natural inclination to not rest until you figure it out, the math, the algorithms, etc. – then you’ll succeed. The specifics of the language, the frameworks, the tools you use don’t matter as much. If you’re committed and capable of solving tough problems, the rest will come.”

Where do you find your inspiration? “When I want to learn something, I totally immerse myself in it. I’ll check out a bunch of books, start to synthesize lots of different perspectives and philosophies of things, and begin making connections between things that I’ve heard about various pockets of my life. I used to say that I wasn’t just doing well in school because I was a good student, but because when I was first taught something, it was already the second, third, or fourth time I saw it. It was just a review. I love to completely drown myself in knowledge, and collect the pieces of understanding through osmosis.”

What’s the one piece of technology you couldn’t live without, and why? “The iPhone. I do things on mine that I probably shouldn’t. I’ve written entire blog posts and committed code with the phone in one hand, and my kid in the other. I guess you could say if I need something to work for me I’ll make it work, even if I find myself without a keyboard or laptop.”

Weiss in his workspace.
Weiss in his workspace.

What’s your workspace like, and why does it work for you? I keep my personal workspace pretty light: just my laptop, notebook, and water bottle with some pictures and figurines on the side. No external mouse, keyboard or monitor. Since I’m not usually at my desk, they just get in the way. I’m around the office for much of the day in meetings and connecting with colleagues, so I just keep my handwritten notebook on hand for the most part. It’s easier to remember important things and say focused in meetings if I leave the laptop behind. The Avvo workspace is a great environment for the product development team. We’re lucky to have product managers and all of their supporting developers, testers and designers all sitting in one area together. This keeps the teams moving and helps form an identity around the product, since problem solving can happen in real-time.

The question always comes up, should teams be organized around a skillset (development, design, test) or a product area (Q&A, Advisor, etc.)? Here, I feel like we have the best of both worlds. Day to day, we’re really product focused, but we all still have shared dev meetings, shared dev culture, and still see ourselves as one dev group. Of course, it’s still important to have cross team developer meetings to share videos, knowledge…or beer.”

Your best tip or trick for managing everyday work and life? (Help us out, we need it.) “Two things: break big tasks into smaller, actionable ones, and if you aren’t planning on working on something today, you shouldn’t even see it. I’ve never found due dates to be very helpful. Scheduling tasks, though, have been incredibly helpful. On Monday morning, I can say, ‘I’ll work on this on Friday,’ and not have to think about it again until Friday – that’s really powerful.

The other important thing is to keep your personal life as a priority. We need that time to recharge. When I’ve been too focused on work when I’m at home, I’m less productive when I’m at work. This has been a part of Avvo’s culture since the beginning: we want everyone to be able to go home and live their personal life, so they come to work with a clear mind, able to function and be fully energized while they’re at work.

Mac, Windows or Linux? “Mac.”

Kirk, Picard, or Janeway? “Picard.”

Transporter, Time Machine or Cloak of Invisibility? “Time machine.”

If someone gave me $1 million to launch a startup, I would … “I recently started writing about Ruby development, and I’ve found it incredibly rewarding to give back to the community and see the talent you’ve been able to help bring out. So I’d probably invest it in creating something around developer education, helping developers bridge the gap between just starting out and being a fully productive, independent developer. I’m especially impressed by things like the Ada Developers Academy, which has been able to help talented students who can’t put a lot of money into their education.”

I once waited in line for … “one of the iPhones. I think it was for the iPhone 4. The longest line was probably to see the Flaming Lips at the Paramount Theatre – but getting a great spot for that show was worth every second!”

Your role models: “Two come to mind: Amy Hoy and David Heinemeier Hansson.

Amy runs a product development course called 30×500, and has taught me so much about writing, about research, about teaching, and about creating things that solve actual problems that real people run into. It’s not just things that seem like fun to build. I’ve learned so much from her, but the most important were the constant reminders to focus on the person whose problem you’re trying to solve, not on yourself or what you’re providing.

David Heinemeier Hansson is the creator of Ruby on Rails. At a time where it seemed like everyone was focused on the structure, architecture, and flexibility of software (and ended up with things like EJB), he took a different approach, and wrote a framework that sacrificed flexibility in favor of convention and understandability. Hansson mentioned that he thinks of himself as a software writer, not a software engineer — and it shows. He evaluates code based on how readable it is, and how easy it is to understand, not how beautiful the architecture is or how easy it is to change.”

Greatest Game in History? “Without a doubt, I’d have to say Deus Ex. It’s a roleplaying game, heavy in conspiracy theory goodness, that came out in the early 2000s. I still replay it about once a year.”

Best Gadget Ever? “The iPhone. It’s the gadget I use most, and it’s not even close.”

First Computer? “Apple //e.”

Current Phone? “iPhone 6.”

Favorite App? “I commute to work by bus, so the podcast player Overcast is probably the app I use most.”

Favorite Cause? “I mentioned them before, but I love non-profit developer education programs, like The Recurse Center and Ada. I love the idea of finding talented people, paying for their tuition by contracting with companies, and teaching people to navigate new worlds in development.”

Most important technology of 2015? “Advancements in virtual reality technologies, like Oculus Rift or HTC Vive.”

Most important technology of 2017? “Self driving cars. I’ve lived without a car for a few years, and I can’t wait to rent a self driving car time once that becomes a thing.”

Final words of advice for your fellow geeks? “No matter what you think you’re up against, there is almost no project that can’t be attempted and accomplished without breaking it into smaller parts, and working on those parts regularly. Almost everything important that I’ve done, I’ve done that way.”

Twitter: @justinweiss

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