EP30: Building web3 email, drive and docs with a privacy-first and decentralized approach, with Andrew Milich, founder of Skiff ($10M Series A led by Sequoia)

Paradigm Shift

Andrew is the founder of Skiff, which is a privacy-first, end-to-end encrypted, wallet native workspace with email, file sharing, and collaboration.

Skiff has hundreds of thousands of users and is part of a broader trend towards privacy-first and decentralization. Skiff is backed by Sequoia Capital who led their seed and Series A.

In this conversation we discuss Andrew’s path to building privacy-first products, approach to finding Product-Market Fit with Skiff, and the various tarde-offs and opportunities when building privacy-forward and web3/decentralized products.

This was a really fun conversation and we learnt so much about what why privacy products matter, their path to increasing mainstream adoption, the business models that are working, and how companies like Skiff are taking us into an exciting future where technology continues to democratize and protect privacy and digital freedom.
Topics discussed:

1. How did you end up working on privacy-first products?
2. What is your vision for Skiff and what does the product to today?
3. How did you approach integrating crypto login with meta-mask and decentralization?
4. How did you approach being privacy-first from the ground up? How does that affect the user experience and user journey?
5. How did you approach the trade-offs between building on centralized and decentralized APIs/components for the best user experience? Eg: onboarding, account recovery, etc.
6. How did you approach e2e encryption and interoperability when building a privacy-first Skiff email product?
7. How did you get started building the initial Skiff MVP and who was your first user?
8. What are your thoughts on competing with very mature incumbent products like GMail, Drive, Notion and Evernote? How have you approached it?
9. How did you build conviction in the opportunity around Skiff and the market opportunity?
10. What have you noticed are some triggers that make people switch to a privacy-first email or collaboration product like Skiff? What are some archetypes of people who seek out these products and switch?
11. Since you don’t track your users, how do you figure out who they are, what they want and figure out how to improve the product?
12. How do you think about the global opportunity and internationalization?
13. How do you cross the user adoption chasm to mainstream adoption from where we are today to privacy-first networked products like email?
14. How do you think about business models for Skiff and privacy products?
15. What made you decide to be consumer first vs enterprise and b2b focused?
16. Who should use Skiff and how should they use it?
17. Zooming out what are some areas in the privacy space that you’re most excited about?
18. Closeout questions: what is the most challenging or difficult feedback you’ve received and how have you processed it? What are some superpowers you’ve identified in yourself that you like to lean on?

Links

• Follow Andrew and Skiff on Twitter
• Signup for Skiff for end to end encrypted web3 email, drive and docs

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