Jamie Wong, Entrepreneur, TV Producer, & Investor: “ The beauty of storytelling lies in its universality — it’s an innate ability that everyone possesses, waiting to be unlocked.”

Meet Jamie Wong, a dynamic force in the world of storytelling. With a rich background as an entrepreneur, investor, and Emmy Award-winning TV producer, Jamie brings a unique perspective to the art of narrative. Her expertise in crafting compelling stories has not only captivated audiences but also transformed businesses.

Currently, as the General Partner at Antler France, Jamie leads both the investment fund and the founder program, imparting her extensive knowledge and experience. Her entrepreneurial journey includes founding Vayable, an online travel marketplace backed by Y-Combinator, and Benefit Studios, a startup studio focused on social impact backed by Google. Her remarkable stint as a TV producer at The Daily Show with Jon Stewart, where she earned an Emmy, Fahrenheit 9/11 by Michael Moore which won the Palme D’Or and her frequent TV appearances, further showcase her versatile storytelling skills.

In this interview, Jamie delves into the essence of storytelling, sharing her invaluable experiences and techniques that transcend traditional boundaries. Join us as we explore the storytelling journey with Jamie Wong, a master storyteller who redefines the way we perceive and tell stories.

In your diverse roles as an entrepreneur, investor, and TV producer, how have you tailored your storytelling approach to resonate in each of the roles?

The essence of storytelling remains unchanged across different roles; it’s fundamentally about understanding and connecting with your audience. Whether I’m crafting a narrative for TV, film, or a business venture, the goal is to create a compelling user experience. The core elements of storytelling — engaging emotions, introducing a conflict, and leading to its resolution — are universal. What varies is the medium and the tools used to bring the story to life, whether it’s the technology in filmmaking, or building a product and taking it to market.

For a founder, storytelling revolves around customers, where the narrative goes beyond marketing. It’s embedded in the very essence of the product, making the product a medium of the story itself. As an investor, my audience shifts to founders and entrepreneurs. Here, the story I tell is through my ability to support and enhance their vision. In both realms, the key element is to consistently focus on the audience or user, placing them at the heart of every story told.

What are the ingredients that go into a fantastic story?

Crafting a fantastic story involves several essential ingredients. First, you need to clearly identify your hero, who should be a reflection of your audience, enabling them to connect and identify with the narrative. Understanding your audience is crucial to this process.

The hero of your story needs to face a conflict or pain, which exists within a specific space or context. This space defines their current reality, and it’s important to establish and understand this reality to set the stage for the story’s progression.

Next, you should introduce a new, special world in your story. This is where the hero’s conflict or pain encounters potential solutions. However, these solutions often come with their own set of obstacles or challenges that the hero is not yet ready to face or overcome, but through guidance, intimately does. Understanding these obstacles is a critical part of the storytelling process.

Finally, the vision of the story, or the ‘promised land’ of transformation, is where the plot transports your hero. This involves understanding the new world that the story creates and how it differs from the hero’s original world. Most importantly, it’s about who the hero becomes in this new world. This transformation is a key element of a fantastic story.

What is the biggest misconception of storytelling?

I think people often confuse storytelling with a fairytale, believing it’s fictional, meant only for entertainment, and solely belongs to the realm of art and literature. However, none of these perceptions are true!

What has been the most challenging aspect of storytelling for you?

The most challenging aspects of storytelling for me revolve around two key areas: the internal mechanics of the story and its external form.

Firstly, pinpointing the exact conflict that will resonate with your audience is a complex task. While conflicts in stories might seem obvious, delving into the depths of a hero’s true conflict still requires a lot of attention and care. It’s about striking the right chord that not only aligns with the story’s essence but also resonates deeply with the audience.

Secondly, tailoring the story’s format and form to suit diverse audiences can also be a challenge. It’s crucial to have a profound understanding of your audience and what truly engages them. A masterful storyteller can transcend these forms by creating content that is universally appealing. However, it can still be tricky to overcome certain forms and stylistic mechanisms that are more relative than universal. The key is to identify these challenges and always revert to the universal aspects of storytelling.

Can you describe a moment in your career where storytelling significantly impacted a situation or outcome?

A standout moment was the launch of my startup, Vayable, in Silicon Valley in 2011. Despite lacking a technical background and domain expertise, my strength lay in storytelling. This skill was instrumental in developing a robust customer acquisition strategy, creating a consumer product, and laying the foundation of a solid business.

Through storytelling, I was able to build a product that people loved. It enabled me to articulate a value proposition that not only spoke to the audience in their language but also empathetically addressed their needs and pains. This aspect of storytelling — understanding and articulating the audience’s challenges and conflicts — became my entrepreneurial superpower, one that I hadn’t fully recognised initially.

Especially in terms of user experience, storytelling played a crucial role. It’s about more than just presenting a product; it’s about crafting a narrative, a journey that the user embarks upon. This approach to storytelling has been a key factor in building products that aren’t just functional but are loved and cherished by users because it meets them where they are.

Where do you look for inspiration on storytelling?

Yeah, there’s so many! The beauty of storytelling lies in its universality — it’s an innate ability that everyone possesses, waiting to be unlocked. While some may spend a lifetime striving to master a musical instrument or excel in a scientific field, storytelling stands apart as a skill that is inherently accessible to everyone. It’s a unique medium that allows us to express our individual perspectives.

Many individuals have mastered this art, each bringing their own distinct flavor to it.

Personally, I’ve found great inspiration in the works of the late Joan Didion, the renowned American author. Her essays have been a source of inspiration for me from a young age and have continued to influence my perspective throughout my career.

How about brands?

When considering brands that I find have done an exceptional job, particularly in their approach to storytelling, BlaBlaCar and Alan stand out. Both companies have done an exceptional job. What makes these brands compelling is their understanding that nailing storytelling isn’t just about crafting clever marketing copy; it’s about focusing on the usersIt’s about building a user experience that is so delightful that it makes people want to do even the worst, most mundane tasks, because you’re taking them on an adventure everytime they use your product. That’s mastering storytelling.

How have your storytelling skills evolved from your time as a TV producer at The Daily Show with Jon Stewart to your current roles as an entrepreneur and investor?

I’ve seen a significant evolution in my storytelling skills. My time abroad, living three years in Spain and three years in France, has enriched my perspective, allowing me to weave diverse cultural narratives into my storytelling.

In my current role as an investor, I focus more on the critical importance of data in storytelling. I’ve come to appreciate how the power of a story often lies in its details. The data I share isn’t just a backdrop; it’s the heart of the story. It’s about conveying information with accuracy and making sure every piece of data tells a part of the larger narrative.

This evolution in storytelling is fundamentally about precision. It’s not about painting with broad strokes. Instead, it’s about carefully planting seeds that grow into a well-informed and compelling narrative.

Join Jamie Wong on February 29 for an insightful session on storytelling techniques that can make a real impact. Her Pollen session, titled ‘How to Tell Impactful Stories,’ is tailored for founders, C-level executives, and professionals in sales and marketing. Don’t miss this opportunity to enhance your storytelling skills. For more information and to register, here.