105: CEO Reveals The Strategy Behind Building A BILLION Dollar Company (BarkBox) | Henrik Werdelin

Are You Missing the Next Big Business Opportunity by Making Innovation Too Complicated? 

What if the key to successful innovation isn't brainstorming clever ideas but simply identifying what genuinely frustrates people? Henrik Werdelin, co-founder of BarkBox and pioneer of the "it sucks that" methodology, demonstrates how focusing on solving real problems rather than generating novel ideas can lead to multimillion-dollar businesses. 

This episode explores how Werdelin has consistently built successful ventures by identifying and solving clear customer pain points. From his early days hijacking MTV's airwaves to showcase internet content, to building BarkBox into a pet industry powerhouse, to his current mission of democratizing entrepreneurship through AI, Werdelin shares practical insights about innovation, problem-solving, and adapting to technological change. His approach challenges traditional notions of entrepreneurship and offers a refreshingly straightforward path to building valuable businesses. 

 This Episode Covers: 

• Why starting with "it sucks that..." leads to better business opportunities than brainstorming ideas 
• How BarkBox evolved from a subscription box service into a comprehensive pet happiness company by staying focused on their core customer 
• The critical difference between selling products and solving problems for a specific customer group 
• Why most senior leaders are failing to properly implement AI (and what to do about it) 
• How AI is democratizing entrepreneurship by making startup resources and expertise accessible to everyone 
• A practical framework for testing business ideas quickly without overcomplicating things 
• The importance of continually planting new "acorns" of innovation around your core business 

Episode Highlights:

(00:00) Introduction to Henrik Werdelin – Damon introduces Henrik, highlighting his journey from MTV to building Bark and his approach to problem-solving. 

(01:30) The Power of “It Sucks That” – Henrik explains his problem-first framework for entrepreneurship and why identifying frustrations leads to better ideas. 

(05:00) Lessons from MTV – Henrik shares how his time at MTV taught him to focus on lifestyle branding over utility and how this shaped Bark’s success. 

(08:33) Building BarkBox – Henrik recounts the early days of BarkBox, using rapid prototyping and customer feedback to validate ideas. 

(12:00) The Acorn Method – Henrik introduces the concept of planting small ideas (acorns) to grow scalable solutions while staying close to customers. 

(17:00) AI and Entrepreneurship – Henrik discusses how AI is lowering barriers for entrepreneurs and enabling faster, more efficient problem-solving. 

(21:30) Autos: Democratizing Entrepreneurship – Henrik shares his vision for Autos, an AI-powered platform that helps anyone start a business in just days. 

(33:18) Advice for Aspiring Entrepreneurs – Henrik offers practical tips on getting started, testing ideas quickly, and overcoming the fear of failure. 

About Henrik: 

Henrik Werdelin, co-founder of NYSE-listed BARK (known for BarkBox) serving over 2.5 million dogs monthly, brings deep expertise in entrepreneurship and innovation from his prior role as MTV's VP of Product Development. As a founding partner of venture development firm Prehype and founder of AI platform Audos, he has advised major companies like Coca-Cola, LEGO, and Microsoft, while his methods are taught at leading institutions including Stanford. A prolific thought leader, Henrik hosts the "Beyond the Prompt" podcast and has authored books on corporate innovation and AI's impact on entrepreneurship, cementing his position as a respected voice in both the startup and corporate innovation spaces. Originally from Denmark but now based in New York, Henrik has consistently been recognized for his creative impact, including being named among Fast Company's Top 100 Most Creative and Silicon Alley Insider's '100 People in Tech'. 

Resources Referenced: 

Henrik Werdelin on LinkedIn 

Beyond the Prompt podcast 

The Acorn Method: How Companies Get Growing Again by Henrik Werdelin   

BarkBox (now BARK) NYSE: BARK 

Audos AI entrepreneurship platform 

PreHype venture development firm 

What's Your Problem?: To Solve Your Toughest Problems, Change the Problems You Solve 

by Thomas Wedell-Wedellsborg  

Co-Intelligence: Living and Working with AI by Ethan Mollick 

Podcast Contact Information: 

Website: www.learnit.com 

Email: podcast@learnit.com 

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