SV Angel Founder Profile: Andrew Milich — Skiff

The third installment of the SVA Founder Profile Series features Andrew Milich, Co-Founder & CEO of Skiff, the company building the only end-to-end encrypted document collaboration platform with password protected folders, expiring links, and secure workplaces. We are so excited to highlight the work that Andrew, Co-Founder Jason Ginsberg, and the Skiff team are doing. We hope you enjoy learning a bit about Andrew’s experience as a founder and how Skiff came to be!

Name: Andrew Milich

Hometown: New York, NY

Role: Co-Founder & CEO

Company: Skiff is a privacy-first, end-to-end encrypted collaboration platform.

Company Location: San Francisco / Remote

Year Founded: 2020

Founding & Mentorship

Q: When did you realize there was a need for your product/service?

A: Jason and I had spent years working on or around cutting-edge security and safety tech — but the lightbulb moment was during a bus ride in Siberia. Today, messaging and communication products have almost universally migrated to end-to-end encryption, placing privacy front and center in product marketing. Spending time around the world (including in Siberia), and working around people with deep security needs — from developing display software for SpaceX’s Dragon 2 capsule to editing Political Risk — revealed a paradigm-changing opportunity to build a huge company.

Q: What was the impetus for starting your company?

A: While building tech prototypes and interviewing hundreds of colleagues, engineers, and potential users, I started working with Jason Ginsberg — Skiff’s co-founder and CTO. Beyond being an incredibly close friend, Jason brought a critical mass of engineering, design, and management skills to get Skiff airborne. Consumers think about the trust, brands, and security behind these products, and our love for engineering and design made it incredibly clear that there is a deep and unmet desire for trusted, privacy-first, and secure-by-design software.

Q: Why the name?

A: Skiff’s name is loosely inspired by the term SCIF — or a sensitive compartmented information facility. However, unlike a cramped or stuffy SCIF, our product is built to be intuitive, freeing, and inspirational.

Q: How does your original business plan differ from what you’re working on today?

A: Generally, our business plan is quite similar in seeing Skiff as building a privacy-first, end-to-end encrypted ecosystem. However, as the product took off, we spent more time focusing on product-led growth. Iteration speed, product feedback, and consumer education on privacy (such as the WhatsApp privacy policy moment in early 2021) were great kickstarters for product-led growth.

Q: Was there a pivotal moment that felt like “failure” at the time, but actually helped to propel your company forward?

A: No pivotal “failure” moments — although building security-first products requires months of design, analysis, auditing, and review. Writing a security model and building it into a product takes time.

Q: When you’re feeling stuck on a problem or idea, what helps you to progress?

A: New engineering designs (particularly those that may touch product privacy or security) are often puzzles — but always solvable ones. Running and Avicii are helpful to get unstuck.

Q: Any advice you’d give yourself when you were starting?

A: Companies aren’t built overnight.

Q: What’s a really difficult part about being a founder that no one talks about?

A: State tax websites are extremely user-unfriendly.

Q: Do you have any thoughts about supporting other founders?

A: Especially in the last year, empathy and generosity mean a lot, particularly when speaking with other founders.

Q: Did/do you have a mentor and how were they most helpful?

A: Teachers, colleagues, and friends have become wonderful mentors. I spent almost three years as a student, research assistant, and thesis-advisee of Professor Amy Zegart — now a member of Skiff’s advisory board; Jason and I were both students in Professor David Mazieres’ cryptocurrency class two years ago (another Skiff adviser). I had the incredible privilege to meet Eddie Fishman and Bert Kaufman during a short summer at Zoox, and to build deep and trusting relationships with Konstantine at Sequoia, Ali and Jenny at Neo, and other Skiff investors over the last five years.

Q: Who or what were/are the best sources for support and advice as you develop(ed) your business?

A: Friends who don’t work in tech often give the best advise: They’re often able to answer the questions I don’t know to ask.

Q: Was there an unexpected piece of advice, or something you heard or read, that stuck with you or reframed your thinking as you built your company?

A: Thucydides’ quote “Who dares wins” has become a deep source of inspiration. Privacy is not the default. It takes courage, engineering discipline, and true daring to build this new vision. The world changes incredibly quickly — giving us a narrow window to build and scale an ambitious dream for privacy-first software.

Fundraising

Q: Were there any important lessons learned during your fundraising process(es)?

A: We realized more and more how valuable the 1–1, individual relationships are, from the partners we work with to angel investors — and want to bring on people who believe in Skiff’s future and in our team.

Q: Why did you choose to partner with SVA?

A: Every one of our existing investors made it clear that SV Angel delivered on their mandate to change company trajectories at critical junctures. We also loved meeting Beth Turner, who we immediately connected with and understood the technical and human dimensions of our product and mission.

Team & Culture

Q: Can you share any valuable lessons about recruiting and scaling a world-class team?

A: We’ve doubled down on putting our ambitious mission to build an ecosystem of privacy-first software in all parts of our recruiting process. The more daring the mission, the more we’ve found world-class team members to join us.

Q: What are your go-to tools for productivity?

A: Going for walks is focusing. It’s been easy to focus on work and spend hours on Zoom this year.

Q: How has Covid-19 affected your company?

A: The shift to remote work accelerated by the pandemic has made our product even more essential. Distributed teams constantly share and collaborate on sensitive information, and the most critical conversations in companies, governments, and families have migrated to secure channels. Skiff’s official start date was April 1st 2020 — only a short time into COVID pandemic — so our team knows no other reality.

Q: How are you supporting company culture and employee engagement through the pandemic/remote working?

A: We’ve started virtual game nights, team lunches, “open Zoom” calls, and random 1–1 coffee chats over Slack. Doing some in-person dinners and other events in the Bay has also been great.

Q: Is there a social cause or organization that you’re particularly passionate about?

A: I love teaching computer science and have spent time doing so all around the world. Before starting Skiff, I also spent time working for the Princeton Gerrymandering Project — to ensure our country’s elections remain free and fair.

Q: How do you think about integrating philanthropy into your company’s culture?

A: Service and empathetic understanding of our mission and users is the foundation of Skiff’s culture. Months of traveling in Asia, Eastern Europe, and other parts of the world revealed a need for Skiff’s product — and families of many Skiff team members (including Jason) made it to the United States as refugees via secure communication channels. We all have personal connections and existential beliefs in the lives our product protects and improves, which has led to deep relationships with our users and opening Skiff up to broader access.

Inspiration

Q: What are you reading, listening to, or watching for inspiration right now?

A: I like listening to Two Friends mixes, watching For All Mankind, and reading books about history — most recently The Anarchy (William Dalrymple) and The Splendid and the Vile (Erik Larson).

Q: As we move toward some return to normalcy following an unprecedented year, what are you looking forward to doing or seeing the most?

A: I’m looking forward to going to baseball games and Bay to Breakers.

SV Angel is a San Francisco-based seed fund.