The Tech Founder Who Became America’s Best Chocolate Maker

Warm Intro

Todd Masonis makes the best chocolate in America—but he took an unexpected path to get there.
Todd co-founded a startup with Sean Parker (yes, that Sean Parker from The Social Network). After selling it for over $150 million, he walked away from Silicon Valley to make chocolate in his friend’s garage.
Seventeen years later, that experiment became Dandelion Chocolate—considered by many to be America’s best chocolate maker (not just a chocolatier, mind you).
In this conversation, we talk about:
– Building fast vs. crafting slow
– What makes good chocolate truly good
– Chocolatiers Vs Chocolate Makers
– Why Chai thinks that Dandelion is the "Mike Tyson of chocolate makers"
– Why thinking in centuries, not weeks, might be the secret to building truly big things
If you love stories about craftsmanship, purpose, and the pursuit of excellence—this one’s for you.

Warm Intro
A conversation, not an interview. Warm, sometimes weird, conversations with interesting people doing big things.

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Hosted by Chai Mishra
Chai is the Founder of The Essential, an ethical commerce company funded by the leading lights of Silicon Valley.
Chai served on the board of UNICEF, and has advised cities, universities, national sports teams and Fortune 500 corporations. A Forbes 30 Under 30 honoree, Chai’s work has also been covered in publications ranging from the SF Chronicle to Business Insider.
Presented by Wefunder
Wefunder created The Community Round.
— allowing founders to raise funds directly from their communities
— allowing anyone to support their favorite founders and join their success.
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Views here are those of the host and the guest. Wefunder makes the show possible but doesn't control who we have on or what we say.

챕터

1. Warm Intro to Todd (00:00:00)

2. Growing up in Connecticut (00:03:48)

3. Being a young nerd (00:05:15)

4. Applying to college (00:06:15)

5. Expectation of Silicon Valley around the internet bubble (00:07:56)

6. Nostalgia for Silicon Valley as an optimistic place (00:08:30)

7. The "Startup industrial complex" in Silicon Valley (00:09:35)

8. Thinking of yourself as an entrepreneur for the first time (00:11:29)

9. Starting Plaxo (00:12:25)

10. Cofounding with Sean Parker (00:12:53)

11. Was Justin Timberlake accurate in The Social Network movie? (00:16:10)

12. Final iteration of Plaxo (00:16:59)

13. The thin line between success and failure (00:19:00)

14. Selling Plaxo for $150M and working at Comcast (00:21:15)

15. Founders don't last at big companies (00:23:02)

16. When did Todd start thinking about chocolate? (00:31:00)

17. Todd’s goals when he started making chocolates (00:31:35)

18. The first moment when he realized that his chocolate was good (00:32:59)

19. Evolution of Todd's palette over the last 15 years (00:34:14)

20. Chai's hot take: "Single origin is not always the best" (00:37:20)

21. Scaling a startup Vs a chocolate company (00:42:44)

22. Scaling craft without killing it (00:45:57)

23. Companies with short term-thinking make everything worse (00:46:40)

24. "This is what we want to exist in the world" (00:47:44)

25. When's the right time to scale? (00:49:57)

26. Dandelion Chocolate is part of the landscape of San Francisco (00:51:32)

27. Building a business with your spouse (00:52:31)

28. Kidnap vacations (00:53:59)

29. A new crisis every day (00:57:26)

30. The agenda Vs the incoming fire (00:59:32)

31. "Dandelion is the Mike Tyson of chocolates" (01:00:20)

32. What success means to Todd (01:01:21)

33. Todd's daily chocolate consumption (01:02:41)

34. Building "the most respected chocolate company in the world" (01:03:54)

35. Dandelion in 30 years (01:04:57)