This Serial Entrepreneur Took A $1.6 Billion Dog Products Company Public, Runs An Incubator Supporting Repeat Founders, And Created An AI Platform to Assist Entrepreneurs

In the fast-paced world of startups, few entrepreneurs stand out quite like Henrik Werdelin. With roots in Copenhagen, a foundation in journalism, and a career spanning MTV, startups, and venture capital, Henrik’s story is a testament to embracing curiosity and adaptability.

Here’s a deep dive into Henrik’s extraordinary journey from his perspective. He talks about having mental models for everything and his views on customer founder fit versus product market fit. Also learn about his thesis for building relationships when raising capital and living in the AI era.

Listen to the full podcast episode and review the transcript here.

Roots in Copenhagen: A Dual Inspiration

Growing up in Copenhagen, Henrik experienced the unique influence of his divorced parents. His mother, a historian with a flair for the academic, instilled intellectual curiosity, while his father, a successful businessman, provided a foundation in business acumen.

This mix of academic and entrepreneurial exposure set the stage for Henrik’s eclectic career. At 18, he moved to London to pursue journalism, envisioning a future as a CNN correspondent.

However, thanks to his mother’s insistence that he learn about computers—sacrificing much of her income to buy a Commodore PC—Henrik’s interests expanded beyond traditional storytelling to include technology and its possibilities. He also did his Master’s in journalism.

In retrospect, Henrik reveals that he had always had this knack for organizing things even in school when he started the school magazine and student radio station. This early experience would prove to be an asset when he started his entrepreneurial journey.

MTV: A Launchpad for Creativity

Henrik’s path to MTV began as a humble internship, but it quickly turned into a pivotal chapter in his life. Here, he was combining his computer skills with his creativity using computers for editing documentaries and other materials.

Henrik recalls how his boss–watching him work on his thesis using the computer at work–asked him to create a TV show about the internet. Henrik came up with the idea to integrate a camera with the computer and do different things with it.

However, Henrik faced resistance from senior management. Undeterred, he broke into the studio late at night to produce a prototype, a one-hour live show—a bold move that earned him not termination but promotion.

As MTV’s young head of product development, Henrik combined his love for storytelling and technology, paving the way for his foray into startups.

The Allure of Startups

Henrik’s time at MTV introduced him to the thrill of building something from scratch. A partnership with a colleague led to his first startup, Tripledash, with MTV and BBC as clients. Eventually, Henrik went back to MTV to run MTV games, working in the company multiple times.

Later, Henrik joined forces with the founders of Skype to create Joost, an early video platform predating YouTube and Hulu. While Joost ultimately didn’t succeed, the experience taught him invaluable lessons about resilience and the cultural differences in how failure is perceived.

“In the U.S., failure is celebrated; in Europe, it’s criticized,” Henrik notes. This realization helped him embrace failure as a stepping stone rather than a roadblock. He also learned about maintaining a positive optimism despite having raised funding for a project that didn’t work out eventually.

Another lesson Henrik learned was that if you work with integrity and are passionate about something, the right people are open to providing backing.

From Entrepreneur to VC and Back Again

Henrik’s stint as an Entrepreneur-in-Residence at Index Ventures gave him a glimpse into the world of venture capital. At Index, he got a glimpse of life at the other side of the table. He learned about different types of programs and how to help entrepreneurs build something that could be funded.

However, Henrik soon realized that commentary and deal-making weren’t his true calling. “I’m born to be on the build side in an operational role,” he reflects. This self-awareness propelled him back into entrepreneurship, where his passion for creating took center stage.

Next, Henrik got extensive exposure to the full cycle of a company. He got the opportunity to join a company in Brooklyn which was later acquired by Facebook, now Meta. He watched the company being born, getting funding, scaling, and eventually, reaching the finish line.

Selling a company is financially rewarding, but, as Henrik points out, entrepreneurs are soon ready for the next step in their careers.

Prehype: A Collective for Founders

After selling the startup in Brooklyn, Henrik founded Prehype in 2010—a unique incubator and studio designed for second-time founders. Unlike traditional accelerators, Prehype is focused on and optimized for the founder’s needs rather than a rigid process.

As Henrik explains, they didn’t have a specific method of working. They never raised money for the holding company and didn’t create a network of founders for VCs. Essentially, they had conversations with the entrepreneurs to understand the kind of company they wanted to build.

It need not be a venture-backed company, but can also be a non-profit, a consultancy, or a solo entrepreneur gig. Founders are also encouraged to talk about the customer class they want to serve and the problems they want to solve.

This human-centric approach fostered the creation of successful companies like BARK (valued at $1.6B when it went public in 2021) and Ro (last valued at $7B). Henrik cites other examples like Managed by Q sold to WeWork for hundreds of millions of dollars and AndCo sold to Fiverr.

Prehype has also supported several consultancies and NGOs which are successfully running today. The incubator’s ethos is simple yet profound: prioritize the founder’s journey. “If you focus on delivering value to the founder, the returns will follow,” Henrik explains.

By offering a space for experimentation and collaboration, Prehype has become a breeding ground for innovation.

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Mental Models and Philosophies

Henrik’s approach to life and business is rooted in his love for systems and frameworks. His “8+1 Framework” helps him allocate time across eight key areas, from family and health to learning and relationships. Weekly reviews ensure he’s balancing priorities effectively.

Henrik talks about having a database and an air table with experiments where he dedicates time carefully, optimizing and brainstorming about different interaction models that will yield better outcomes. He considers himself a philosophical person.

For Henrik, success isn’t about rigid objectives but about pursuing “interestingness with great intensity.” Inspired by Kenneth Stanley’s book Why Greatness Cannot Be Planned, Henrik believes in building stepping stones without always knowing where they’ll lead.

This philosophy underpins his approach to startups: identify a customer and a problem, then iterate from there. Henrik believes in the thesis that “We shouldn’t make objectives and fixed goals because they tend not to materialize in the way that everybody says.”

Building BARK

When creating BARK, the mission wasn’t just about putting items in a box and shipping them. Instead, the goal was to bring joy to people who love dogs by addressing their unique needs. Henrik recalls how he built the initial website over the course of the weekend.

Next, along with his co-founder, Matt Meeker, Henrik went down to the dog park and talked to people about their idea. Interested subscribers were happy to sign up with $25 and the company ended up having 70 customers without an MVP.

Henrik emphasizes the importance of building businesses rooted in deep customer understanding and the concept, “relationship capital” or “customer-founder fit.” He underscores understanding the problem and then building many products and services for that specific user group.

After the success of BarkBox, the company didn’t branch into unrelated products like a subscription service for cats. Instead, BARK expanded within the dog-focused category, introducing airlines, treats, and other services to further enhance the experience of dog owners.

Ro – The Next Venture

Similarly, with Ro, the company started by addressing sensitive medical issues, such as erectile dysfunction, which many men find difficult to discuss. From there, Ro expanded into products for hair loss and weight loss, all tailored to the same core audience.

This focus on customer problems and the creation of interconnected solutions was also a strategy behind Managed by Q, which developed products and services to assist office managers. Henrik stresses that his entrepreneurial philosophy always begins with understanding the customer.

“What’s the problem?” he asks. From there, he reframes, tests, and identifies opportunities to create multiple solutions that align with customer needs.

Audos – A Vision to Democratize Entrepreneurship

Henrik’s latest venture, Audos, is an ambitious platform aimed at democratizing entrepreneurship. Drawing inspiration from the staggering fact that while 60% of Americans claim to have an idea for a startup, only 8–10% act on it, he believes that artificial intelligence can bridge this gap.

Henrik highlights barriers such as a lack of resources, knowledge, and support that prevent people from pursuing their entrepreneurial dreams. Audos aims to change this by leveraging AI to perform traditionally challenging tasks.

AI can accomplish tasks like interviewing customers, having a scale conversation with them, building the product, and getting financing.

Henrik envisions a future where individuals with authenticity and authority in specific customer groups can use AI to handle operational complexities while focusing on building meaningful relationships with their audience.

The goal is ambitious: launching one million companies over the next decade. Henrik likens this vision to what YouTube did for storytellers, Shopify for e-commerce entrepreneurs, and Airbnb for aspiring hosts.

In his words, “Entrepreneurship is a critical quality, and AI can empower people to create scalable solutions for the world’s endless problems.”

The Importance of Playfulness and Resilience

Reflecting on his entrepreneurial journey, Henrik offers advice to his younger self: don’t take everything so seriously. He recalls a piece of wisdom shared by Reed Hoffman, co-founder of LinkedIn, who estimated that even smart entrepreneurs only succeed one in five times.

Henrik suggests embracing the long and iterative nature of entrepreneurship with a more playful mindset. He also highlights the importance of self-care, citing a poignant piece of advice from Richard Branson: “Go to the gym.”

According to Henrik, maintaining physical and mental well-being is crucial. Success in business often requires hard work and a bit of luck, but what matters most is ensuring you remain whole at the finish line.

Entrepreneurs, Henrik says, should aim not only to succeed but to do so without compromising their health or happiness along the way. For aspiring entrepreneurs, Henrik offers a valuable lesson: embrace failure, prioritize learning, and let curiosity guide the way.

Reflections on the Startup Journey

Henrik Werdelin’s story is a reminder that entrepreneurship is less about achieving a singular milestone and more about the journey itself.

Whether breaking into a studio at MTV, building a billion-dollar company, or helping others find their next venture, his path has been defined by curiosity, boldness, and a relentless focus on creating value.

By combining empathy for customers, embracing AI-driven innovation, and fostering resilience, Henrik continues to inspire and redefine the entrepreneurial journey.

Listen to the full podcast episode to know more, including:

• From journalism to startups, Henrik’s journey underscores the value of embracing curiosity and adapting to change.
• Successful ventures prioritize deep customer understanding and alignment with the founder’s passion, as seen with BARK and Ro.
• Henrik’s experiences, like the failure of Joost, highlight the importance of resilience and learning from setbacks, treating failure as an integral part of growth.
• Henrik’s ventures, including Prehype and Audos, focus on creating value through innovation while solving specific problems for well-defined audiences.
• Entrepreneurs should approach their journey with resilience, a playful mindset, and a focus on physical and mental health to sustain long-term success.
• Audos leverages AI to lower barriers to entry for startups, empowering individuals to scale their ideas and create impactful businesses.
• Henrik’s life philosophy of building systems, experimenting, and pursuing “interestingness” over fixed objectives offers a flexible approach to achieving greatness.

 

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