Skiff

Andrew Millic started writing code for Skiff in late 2019, working eight to nine hours daily after his day job for four months. Having worked on security and privacy at SpaceX and on autonomous vehicles, he felt the pull toward building software that demanded the same rigor, security, and performance standards he'd experienced in those roles. The vision was clear: create a collaborative workspace as polished and intuitive as Notion, but fundamentally different in its architecture—encrypted end-to-end, decentralized, and built on the principle that companies should never have access to what users create or share.

By early 2020, Andrew partnered with Jason, a Stanford electrical engineer and designer, who became co-founder and CTO. The two split equity roughly 50-50 (with some adjustment for Andrew's early groundwork) and committed to working as equals. "Having a co-founder who isn't a 95-5 split was one of the only ways we got this far," Andrew reflected. They built from the ground up with a different philosophy than existing collaboration tools—no client-side tracking, end-to-end encryption, and a company architecture where Skiff's team literally cannot access user data. While visually similar to Notion, every technical and operational decision prioritized privacy and user data ownership.

Skiff's early traction came through deliberate, ground-level community work rather than paid marketing. Andrew and Jason grinded privacy communities where they were already members: DEF CON, LocoMocoSec, Ethereum conferences like DevConnect and NFT New York/Miami. They engaged in subreddits like r/privacy and r/privacy tools, hung out in Telegram and Discord privacy channels, and built relationships in pseudonymous crypto circles. These weren't random audiences—they were ideologically aligned people who cared deeply about privacy and data ownership. Many gave critical feedback that shaped the product, pushing them to refine privacy policies and security models. By mid-2020, roughly eight months in, this community immersion had created enough clarity and traction to raise a seed round.

In June/July 2020, Skiff raised $4.1M in seed funding ($2.5M initial + $1.5M from angels) on reasonable valuation caps for the time. Then in late summer 2021, they closed a $10.5M Series A, with Series A investors taking 10-15% of the company (valuing Skiff at roughly $70-100M post-money). What worked was pure product-led growth: tens of thousands of monthly active users (with over 1,000 paid seats by the interview date) signing up organically through communities, not ads. The monetization model was pragmatic—$10/month for individuals, ~$20/month for enterprise on a per-seat basis—but Andrew was thoughtful about not paywalling features critical to onboarding (like templates or encrypted search). Month-over-month growth hit 30% consistently, helped by viral moments like a YouTube video about Skiff released in China that bumped growth 30% in three days. However, Andrew was candid: "We don't really know the exact number" of MRR (estimating $10-20k/month but not tracking it precisely), choosing instead to obsess over seven-day retention curves, DAU, and month-over-month user growth as the true north metrics.

With $14.6M raised and more than two-thirds still unspent (~$10M in the bank), Skiff was running lean—15 to 20 engineers distributed globally (Bay Area, New York, France, Israel, Hungary, Egypt, Taiwan), with almost no marketing spend. The team consisted of engineers with backgrounds in security, blockchain, and autonomy work from places like SpaceX and Stanford. Andrew's near-term focus wasn't revenue but scale: reaching millions of users, which he saw as a prerequisite for meaningful monetization and a competitive Series B. The roadmap included broadening the platform beyond collaboration/writing to include more Google Workspace-like features (announced in the coming weeks) and rolling out self-serve enterprise options. When asked if the DOJ ever demanded a backdoor, Andrew was unequivocal: "Definitely not." The decentralized, crypto-wallet-linked architecture made forced access technically infeasible—a feature, not a bug.