How Chocolate Stole the Heart of a Tech Millionaire

In this episode, we chat with Todd Masonis, Co-founder of Dandelion Chocolate, about his journey from tech entrepreneur to leading a craft chocolate movement. Todd shares his story of starting Plaxo, selling it to Comcast, and then diving into the world of chocolate-making with nothing but curiosity and determination.

Todd talks about the lessons he’s learned, from hiring the right people to building a company culture that truly reflects his values. He explains what success means to him, not just in terms of growth, but in creating something meaningful and long-lasting. 

We also explore how Todd approaches storytelling, works with investors who share his vision, and keeps his focus on the bigger picture while staying grounded in the day-to-day work. 

This episode is packed with down-to-earth insights for anyone dreaming of starting something of their own—or just curious about what it takes to build something special.

Key Topics:

• How Todd started his journey as an entrepreneur
• Turning a love for chocolate into a business
• Building a strong team and company culture
• Staying focused while managing challenges
• Defining success and creating something meaningful

Quote  From The Episode: 

"I'm just trying to build something that I want to exist in the world"

- Todd Masonis

Timestamp:

[01:54] Todd shares his incredible journey with Adam, recounting how he transitioned from co-founding Plaxo to leading the American craft chocolate movement with Dandelion Chocolate. His passion for creating something meaningful is evident as he reflects on the drive behind this significant shift.

[10:37] In their discussion, Todd talks about what entrepreneurial excellence means to him, emphasizing the importance of building something meaningful and sustainable while cultivating a strong and adaptable team culture.

[21:24] The conversation deepens as Todd shares his approach to embedding sustainability and mission-driven values at the heart of Dandelion Chocolate, providing Adam with a glimpse into the principles guiding the company.

[29:43] Todd explains how Dandelion navigates complex challenges by implementing robust data systems, exception-based management, and multi-threaded planning, giving Adam a detailed look into their strategic operations.

[39:50] The discussion shifts to scaling, where Todd shares with Adam the intricacies of growing Dandelion Chocolate, reflecting on the challenges and opportunities that come with expansion.

[50:58] Todd reflects on his evolving role as a founder, explaining to Adam how he moved from being deeply hands-on to focusing on strategic delegation and team-building, allowing him to lead more effectively.

[59:52] As the conversation nears its end, Todd talks about the importance of staying true to your vision, highlighting key lessons from his entrepreneurial journey that resonate deeply with Adam and the audience.

[1:08:50]  Outro

Connect with Todd Masonis

LinkedIn - linkedin.com/in/todd-masonis-42a2

Website - www.dandelionchocolate.com/

Connect to Entrepreneurial-Excellence

Website - https://www.levy.company/entrepreneurial-excellence