Originally posted on ideamensch.

Rob Villeneuve is passionate about the Internet, its development, and its use. He’s an expert in Internet domains, hosting, infrastructure, and policy management. Before becoming the CEO of Rebel.com, Rob worked as a software engineer, a web developer, a small business owner, and a startup founder.

Rob actively contributes to global Internet policy through the Internet Corporation for Assigned Names and Numbers and currently sits on the board of directors for the Canadian Internet Registration Authority, which manages the .ca domain space.

Where did the idea for Rebel.com start?

Rebel.com isn’t new as much as it is a reimagining of something old. We had the name, and we liked it — but we didn’t have an identity, a culture, a brand, or really even a story behind what we were all about. We’d been running a successful business in our industry for 15 years, so it took some courage to make a change we knew could disrupt our customers. But taking our business to the next level meant we had to put more of ourselves into it, and we had to build something that we related to and that really drove us. We took a giant step back and looked at why we existed.

We wanted Rebel.com to reflect the bravery, thoughtfulness, humor, and audacious spirit of the people behind it. We wanted to make amazing, simple products and have a support team that left our customers smiling. We wanted to be in the business of inspiring people to contribute their ideas, knowledge, perspectives, creative pursuits, products, or services to what we see as the world’s bravest communication space — the Internet. We didn’t change the fact that we’re a domain registrar or much about our products and services, but we focused on a purpose and brand that motivated us to take everything to the next level.

And Rebel.com was (re)born.

What does your typical day look like, and how do you make it productive?

My role is to be a leader and to inspire people, which doesn’t come with a schedule. Some days, I’m the team captain — I jump in and get my hands dirty, not asking anything of others if I’m not doing it myself. Some days, I’m the coach empowering people and removing impediments so they can do their best work. Most days are a balance of the two.

I believe in ceremony and cycles — daily, weekly, monthly, quarterly, and annually. This type of planning, along with team-led check-ins, keeps our work moving down the right path in a predictable, rhythmic way. So as haphazard as my day sometimes is, it keeps the whole organization on beat and moving toward our goals. When things are going well, I focus on the other important aspects of leadership, like research, strategy, and maintaining some semblance of work-life balance.

How do you bring ideas to life?

We get the idea in front of a customer as quickly as we can so we can start learning. We listen, collect feedback, make improvements, and repeat.

What’s one trend that really excites you?

Beards. And when plaid comes back in every once in a while, I get excited.

What is one habit of yours that makes you more productive as an entrepreneur?

My degree is in computer science. In software, you’re trained to think about a problem from every angle, identify all of the variables, think through the use scenarios, and tease out exceptions. You analyze systems and simplify their function into models of layers and hierarchies. After a while, this becomes so natural that you can approach every problem this way.

It sounds like a lot of work, but it isn’t. Once you have a model, you can develop your hypothesis quickly and predict outcomes. My colleagues sometimes call this overthinking, but approaching problems from this hyper-logical space works for me.

What was the worst job you ever had, and what did you learn from it?

I’ve never really had a “bad” job. I started my own software and web business at 18, so if work sucked, then I was to blame. In fact, if your job sucks, you should fix it. If you can’t fix it, then move on. Either way, take control.

I did have a few strange jobs along the way, though. I bagged groceries, paved sidewalks, cleaned ditches, and worked office demolition. These jobs showed me that I would rather write software, and each of them encouraged me to fully dedicate myself to the craft.

If you were to start again, what would you do differently?

Career-wise, I would change everything. Life is a journey — a series of experiences. If you can do it all over, don’t focus on eliminating regrets. Instead, do it all differently. Experiment. Make the experience totally new.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

No team is perfect, and agile retrospectives offer an iterative approach for a team to self-improve through experimentation. You should inspect and adapt. Make a small change, and see whether things improve. If they do, great. If not, try something else. This simple approach eventually leads to significant insights and improvement. Best of all, it empowers the team to control its own destiny.

What is one strategy that has helped you grow your business?

People don’t buy what you do, they buy why you do it. There’s so much value in being yourself because you own it, and customers are drawn to that. Customers can feel it. If someone understands why you’re doing something, you’ll be surprised by how excited he is to support you.

What is one failure you had as an entrepreneur, and how did you overcome it?

We failed a startup after two very hard years. I didn’t overcome it as much as I just moved on. Many of my friends finished their master’s degrees around the same time. They also had two very hard years and a lot of debt at the end.

Looking back, a failed startup is the best education I could have received. It enabled me to experience the roles of software developer and leader. It’s rare for people to have solid experience in both. I believe the insight (and humility) gained during this failure sent my career on a unique path.

What is one business idea that you’re willing to give away to our readers?

You don’t need my ideas. Do what you’re already most passionate and excited about. Starting a business requires huge sacrifices, and you’ll probably fail. So you better be directing the sacrifice toward something you’re passionate about.

Oh, and an Uber for dogs.

What is the best $100 you recently spent?

A Big Trusty Rusty wedge. It fixed my short game.

What software and web services do you use? What do you love about them?

I use Rebel.com for all my domain and web hosting needs, Trello for replacing Post-it notes on the wall, Slack for better team communication, SpeakUp for product feedback, TINYpulse for employee feedback, and Siri for sending my wife a message while I’m driving.

What is the one book that you recommend our community should read and why?

Agile Estimating and Planning is a book that I give people who are new to managing a team. It teaches them how to think systematically about the workload and challenges in front of them, and it is a great way to learn agile.

What people have influenced your thinking and might be of interest to others?

Here are two people who have influenced me recently:

Simon Sinek, the author of “Start With Why” and the leader of the “Why Discovery” course that followed
Dr. Balaji Krishnamurthy, chairman and leader of Think Shift