Beyond the Algorithm: Relentless curiosity & asking the right questions

Before WDR Aspen existed, Olivier De Ridder was working in corporate America, tackling problems alone that most people would need a team to solve. I was running a small SEO agency at the time, and when a client I couldn’t say no to came to me with a challenge I struggled to say yes to, I knew I needed help. That’s when Olivier stepped in. 

What started as a collaboration quickly became a partnership. Olivier was the missing piece — the person who could turn raw speed and vision into structure, momentum, and measurable growth. Together, we built WDR Aspen from a niche local agency into a full‑stack marketing firm of more than fifty professionals. He often jokes that I was like a race car without a race track; he built the track. 

Olivier is one of the sharpest minds I know — equal parts creative and analytical, blending the discipline of an engineer with the imagination of an artist. He sings opera, is a professional card game player, worked as a data scientist, is a brilliant marketer, and is a friend. 

In this conversation, I wanted to give the community an intimate view of the person behind the ‘DR’ in WDR, and take a look at what shaped him, what drives him, and why curiosity has always been his compass. 

 Q: Olivier, can you start by sharing a bit of your origin story? 

Olivier: I grew up in Belgium. Since childhood, I’ve always been passionate about learning and discovering new areas. I remember in high school I could never quite decide whether I wanted to explore languages or to focus on sciences, and so I just decided to do both. 

I completed the maximum hours of Latin and Greek, but also the maximum hours of math. Even going into college, I was like, Oh, let’s study Chinese, but also, let’s minor in economics! 

Q: You’re multilingual. How many languages do you speak? 

Olivier: Well, it depends on the definition of speak, right? So, my mother tongue is Dutch, and obviously, I’m pretty fluent in English. Then there are probably another three to five languages that I speak with various degrees of fluency. 

Q: You’ve also trained to learn how to sing opera. Where did that begin? 

Olivier: I first fell in love with musical theater, and decided if I was going to sing, I should learn how to do it properly, so I started by enrolling in some courses and eventually began taking private lessons. I started to pick up that some of the best musical theatre singers were trained classically, and began to seek out that level of education. When I moved to the U.S., I started training under some amazing maestros and began focusing more on opera. It became a great passion of mine. I used to sing with the Omaha Opera. 

Q: How has your passion for music contributed to your professional life? 

Olivier: I think you always need to have a creative outlet in life. I haven’t been able to perform professionally since COVID, but I love to have a creative outlet. Marketing is fundamentally a creative endeavor. It’s about storytelling, about bridging datapoints together to find a unique angle, and I’ve always seen a lot of analogies between music and marketing. At the end of the day, you have to be able to harmonize different marketing channels to make a beautiful symphony. 

Q: Considering your diverse interests, have you found yourself trapped by the “Jack of all trades, master of none” dichotomy? 

Olivier: Well, I think the term itself is a bit of a trap. The full saying is “a jack of all trades is a master of none, but oftentimes better than a master of one.” In reality, I think the number one skill set you can develop is relentless curiosity. If you’re able to ask the right questions, you can become quite good at many things, just because you’re able to get to the core of what it is that you’re trying to solve. 

Q: You’ve built impressive departments within WDR, ranging from IT to web design and everything in between. How did you develop so many different capabilities? 

Olivier: It again comes down to asking the right questions. I’ve always believed that if you can understand the root of a problem, you can learn how to solve almost anything. I was also inspired by Bryan and the pace at which he tackles and solves problems. I think oftentimes people waste hours on tasks that could take minutes, not because the problem is too hard, but because of indecision or unnecessary contemplation. 

I think the pathway to scaling the way we did across so many departments is combining thoughtful, deliberate strategy with relentless energy and work ethic, and fully committing to the intended result. That’s our playbook. 

Q: You have a team of people who look to you as you navigate new challenges with strategy and expertise. Has that framing of the term made you immune to impostor syndrome? 

Olivier: No, I struggle with it all the time! I think some of the most successful people probably struggle the most with impostor syndrome, not that I’m considering myself the most successful. For me, there is a fundamental tension that is always present — this relationship between overconfidence on one hand and impostor syndrome on the other, and the goal is to make it a successful marriage, right? Balance a sense of curiosity with a focus on getting to the core of a problem — let that focus give you the confidence to get it done without holding yourself back with impostor syndrome. 

I’ve also learned that everyone deals with impostor syndrome to some extent at some point in their life. It’s up to you whether you let it cripple you or choose to push ahead anyway. Early in my career, I decided to say yes to every good opportunity, regardless of the inevitable feelings of insecurity. If you’re committed and believe you can do it, you’ll find a way. 

If you wait for everything to line up perfectly, you’ll miss out on great opportunities. The beauty is that in the act of doing, you acquire the skill, and those lived experiences gradually quiet the voice of doubt. 

Q: What is your strategy for learning? 

Olivier: I discovered early on that my learning style is holistic, and what I mean by that is: I learn through narrative. When I was in school, I sometimes struggled if a teacher didn’t explain something in a way that I understood, and at a certain point, I realized it wasn’t that the material was too difficult — it was that the way it was being explained didn’t click. So I started developing my own way of learning. 

I would look up how different teachers and professors approached the same subject, read their blogs and materials, and then write out my own version as if I were teaching it. Almost like my own personal curriculum. That became my personal strategy for life. 

I learn by putting puzzle pieces together into a narrative I understand. Once I have that story, I can make it my own, apply it, and master it. 

Q: Has that process evolved? 

Olivier: Now, in a world with AI, that whole process is supercharged. I still gather information from podcasts, books, and YouTube, etc., but AI helps me process and interact with it much faster. 

Q: What would be your advice to a young person who felt they were too curious for their own good? 

Olivier: Realize that no problem you have is novel. All your problems have been solved by people before you, thousands of times over. With research, you can find what others have shared on those topics and leverage those learnings to supercharge your project. Always have a bias for moving fast, and don’t wait for the perfect conditions to act. 

From budding Belgian polymath to the cut and thrust of corporate America, Olivier De Ridder’s reflections remind us that curiosity isn’t a distraction but a true superpower, and that confidence grows not from certainty but from saying yes and committing to the fullest extent. 

Bryan Welker lives and breathes business and marketing in the Roaring Fork Valley and beyond. He is President, Co-founder, and CRO of WDR Aspen, a boutique marketing agency that develops tailored marketing solutions. Who should we interview next? Reach out and let us know bryan@wdraspen.com.