Secrets from the Dropout Millionaire

In this episode, Charles delves into the world of exclusive fashion and entrepreneurship with Kola Tytler, the visionary founder of Dropout Milano. Kola shares his remarkable journey of building a thriving streetwear and sneaker store in Milan, Italy, while still pursuing his medical degree. Get ready to be inspired as Kola unveils his unique approach to creating an aspirational brand that resonates with its target audience.

Uncover the power of exclusivity and experience-driven marketing as Kola reveals how he transformed Dropout Milano into a community-focused brand that goes beyond just selling products. Through engaging stories and practical insights, Kola and Charles explore the importance of understanding your market, identifying customer motivations, and leveraging data to optimize your marketing efforts.

Kola’s passion for continuous learning and self-improvement shines through as he discusses his pursuit of multiple degrees from prestigious UK universities, including an upcoming Masters at Cambridge. He emphasizes the significance of investing in your own education and network to build confidence and make better business decisions.

Whether you’re a seasoned entrepreneur or just starting your journey, this episode will provide you with valuable lessons and frameworks to help you create a brand that stands out in today’s competitive landscape. Get ready to be motivated and equipped with the tools necessary to build a loyal community around your brand and achieve remarkable success.

Key Takeaways:

  • Learn how to identify and capitalize on niche market opportunities
  • Discover strategies for creating exclusivity and building brand loyalty
  • Understand the importance of balancing multiple interests and skill sets in entrepreneurship
  • Gain insights into effective marketing techniques for luxury and streetwear brands
  • Explore the value of continuing education and expanding your network



This episode uncovers Kola’s innovative approach to creating buzz and exclusivity around his brand. He shares the strategy behind Dropout’s first store opening, where minimal information was released online, yet crowds gathered in anticipation. Kola’s tactics for leveraging scarcity and mystery offer valuable lessons for businesses looking to generate excitement and loyalty among their customer base.


The conversation shifts to explore Kola’s philosophy on experiential retail and community building. He explains how Dropout goes beyond selling products to create memorable experiences, from hosting pop-ups with international brands to organizing exclusive events for customers. Kola’s insights on building a brand that resonates with a specific community while remaining aspirational to a broader audience provide a masterclass in modern brand strategy.


The episode is structured to guide listeners through key milestones and strategies in Kola Tytler’s entrepreneurial journey:

Key Points

  • 1:00 Entrepreneurial Journey: Explains balancing medical school with starting a sneaker business.
  • 5:55 Multiple Interests: Discusses the importance of pursuing diverse passions simultaneously.
  • 7:26 Market Opportunity: Details identifying and capitalizing on a gap in Milan’s fashion market.
  • 10:27 Business Model: Shares insights on creating a model catering to enthusiasts and aspirational customers.
  • 13:53 Brand Exclusivity: Explains strategies for building an exclusive brand image.
  • 15:36 Store Launch: Describes the unique approach to Dropout’s first physical store opening.
  • 18:09 Online Exclusivity: Discusses maintaining brand exclusivity in e-commerce.
  • 20:22 Product Curation: Shares approach to selecting products for online sales.
  • 22:07 Brand Partnerships: Explains the benefits of collaborating with other brands.
  • 24:02 Customer Engagement: Describes innovative strategies for creating unique brand experiences.
  • 25:55 Brand Identity: Discusses the importance of developing a strong, consistent brand identity.
  • 28:00 Content Creation: Shares strategies for developing lifestyle-focused, experiential content.
  • 30:00 Community Engagement: Explains the value of active participation in online communities.
  • 32:24 Viral Marketing: Offers insights on creating shareable, viral content.
  • 33:55 Brand Consistency: Shares approaches to maintaining consistent brand messaging.
  • 36:24 Advertising Balance: Discusses balancing brand awareness with conversion-focused advertising.
  • 40:14 Continuous Learning: Emphasizes the importance of ongoing education and self-improvement.
  • 42:30 Further Education: Reveals plans to study entrepreneurship at Cambridge University.
  • 44:58 Academic Recognition: Host encourages acknowledgment of impressive academic achievements.
  • 46:42 Online Resources: Discusses leveraging online learning for personal and professional growth.
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This episode is a goldmine of information for anyone interested in entrepreneurship, brand building, or the fashion industry. Kola Tytler distills years of experience into actionable advice, offering a roadmap for identifying market opportunities, creating a unique brand identity, and building a loyal customer base. He emphasizes the importance of continuous learning, sharing his decision to pursue further education at the University of Cambridge despite his business success.

From leveraging social media and influencer partnerships to creating in-store experiences that drive foot traffic and online engagement, the strategies discussed provide a comprehensive guide to thriving in today’s competitive retail landscape. Kola’s journey also highlights the value of a diverse educational background, demonstrating how skills from different fields can contribute to entrepreneurial success.

Tune in to gain insights from a true innovator in the streetwear space and learn how to apply these principles to your own business ventures. Whether you’re just starting out or looking to take your brand to the next level, Kola’s story offers inspiration and practical wisdom for navigating the ever-evolving world of fashion and retail.

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