May 15, 2022 · 25m · top-founders
Skiff is Privacy Focused Notion, Breaks $60m Valuation, 10k MAU's
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of Conversations with Nathan Latka, Skiff co-founder and CEO Andrew Milich details how his startup is building an end-to-end encrypted workspace to rival Notion and Google Workspace. He explores Skiff's monetization strategy, zero-knowledge privacy architecture, capital efficiency, and organic community-led growth toward a near-$100 million valuation.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 39.5% of the talking time here. How this is scored →
Nathan as informed peer 4.7 Guest teaching 2.4 Guest disagreement 2.0 Nathan pushing back 3.6
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 9:27 Milich refuses to disclose monthly recurring revenue
Milich firmly resists Latka's direct pressure to state MRR figures, pivoting instead to prioritize retention and user growth metrics.
Hardest push from Nathan ▶ 9:25 Latka rejects revenue vaguenessLatka directly confronts Milich's deflection, insisting that as CEO he must know his company's monthly recurring revenue.
Biggest teaching moment ▶ 21:09 Milich explains mathematical impossibility of key backdoorsMilich explains why decentralized architecture and client-held private keys make government backdoor compliance technically impossible.
Nathan holds their own ▶ 18:24 Latka deduces valuation from dilution metricsLatka uses Series A round size and dilution percentages to pinpoint Skiff's valuation range despite the founder's attempt to keep it secret.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Introducing Andrew Milich and the SpaceX Connection | 4 | 2 | 1 | 1 | Latka inquires into Milich's transition from SpaceX autonomous vehicle engineering to privacy-centric software. The tone is collaborative as Milich defines Skiff's end-to-end encrypted workspace vision. | |
| Evaluating Paywalls Versus User Engagement | 6 | 3 | 2 | 4 | Latka shares strategic frameworks around pricing psychology, advising against premature paywalls that sacrifice viral adoption. Milich agrees, noting Skiff focuses monetization on storage capacity rather than basic collaboration utilities. | |
| Origin Story and Co-Founder Equity Split | 6 | 3 | 4 | 7 | Latka pushes hard to extract exact MRR and paid subscriber figures, refusing to accept Milich's deflections. Latka also challenges lenient MAU definitions, warning that passive login metrics frequently mislead early founders. | |
| Sponsor Message: Remote.com for Global Hiring | 2 | 1 | 0 | 1 | The segment primarily consists of a sponsor read for Remote.com followed by brief technical questions on day-X retention cohort tracking. The atmosphere is neutral and standard. | |
| Seed and Series A Funding Overview | 5 | 2 | 2 | 3 | Latka details market norms for seed valuation caps and compares them against Skiff's capital structure. Milich details raising $4M at seed and $10.5M at Series A to fund a specialized engineering team. | |
| Cash Reserves, Dilution, and Valuation Estimates | 6 | 3 | 3 | 6 | Latka questions whether Skiff can raise a competitive Series B without prioritizing revenue and calculates an implied valuation above $70M based on standard 10-15% dilution. Milich coyly declines to confirm the exact valuation while discussing growth channels. | |
| Backdoors, Decentralization, and Regulatory Requests | 4 | 3 | 2 | 3 | Latka presents a regulatory scenario involving hypothetical government backdoor demands, prompting Milich to explain how cryptographic decentralization prevents compliance. The episode wraps up smoothly with the rapid-fire Famous Five questionnaire. |
Statements from this episode (25)
Milich: Skiff will expand into Google Workspace competitor within weeks
“Actually in a few weeks, we're kind of broadening that vision significantly and bringing in kind of more aspects of the typical Google WorkSuite, and so you'll see that in the next few weeks.”
Milich: Skiff cannot access any content that users write or share
“We don't have access to everything you write and you share, and you're the only person who owns your data.”
Milich: Skiff has paying individuals and SMB customers up to 100 employees
“We have some paying customers, a bunch of individuals, and then we're kind of, we have some kind of, I'd say small to medium sized businesses up to a hundred people paying for skip.”
Milich: Skiff charges $10 monthly for individuals and about double for enterprise
“So for the individual plan, people are paying, I believe it's 10 dollars a month, or maybe there's an annual plan discount. And enterprise is anywhere from depending on the options you choose, you know, about double that.”
Latka: Paywalls carry a hidden opportunity cost in lost user engagement
“I mean, I think what, where I do think there's a big gap here is what people never quantify with pricing is what you miss out on when you put up a paywall in terms of engagement and what the opportunity cost is.”
Milich: Skiff Refuses to Paywall Encrypted Search and Templates
“Like, we specifically don't want to put paywalls on things that will make you kind of have a better experience on day one on Skit. So, for example, our templates feature, which lets you kind of share and use anti-encrypted templates searching through anti-encr…”
Milich: Skiff monetizes easily on storage because users expect linear pricing
“So one of the things we can monetize pretty easily is storage space. People are probably paying for storage space in their life already, whether it's on Google or it's on Dropbox or something else. And so that's something that's pretty common. Also it's, you k…”
Milich: Skiff co-founders split equity roughly fifty-fifty
“Yeah, roughly that. I mean, I kind of set up a lot of the structure in those interim few months. And so then we kind of, we want it to work together as equals.”
Milich: Founders should avoid highly unequal equity splits
“Well, I think it is really important to have a co-founder who's not, you know, like not a five 95 split or, you know, a really unequal split just because there are so many rough and grinds, you know, grinding moments in that first few years that I think just h…”
Milich: Skiff's MAU growth exceeded 30% month-over-month
“It's been, I think, over 30% for the last few months.”
Milich: Chinese YouTube video lifted Skiff growth 30% in three days
“Like we had a YouTube video released about Skiff in China on Friday that probably bumped our growth up 30% in three days.”
Milich: Skiff aims for 30% monthly growth over next year
“So well, it's unclear how sustainable those events are, but you know, we're kind of aiming to do 30% month over month growth for the next year or so.”
Milich: Skiff utilizes zero client-side tracking
“So like, there's no client side tracking, anything like that.”
Milich: Mobile and desktop apps drive higher retention in workspace products
“And obviously stuff like mobile apps, desktop apps leads to much higher retention in products like ours.”
Milich: Skiff raised approximately $4M in seed funding
“So we raised, I think, two and a half million initially, and then we ended up adding about one and a half a million from angel investors right after that. So it ended up being about four.”
Milich: Skiff Wants 10x User Growth Before Series B
“I think we want to have at least 10 times or more as many users.”
Milich: Skiff Has Retained Over Two-Thirds of Its $14M Raised
“Also, by the way, of the kind of fourteen million we raised, like more than two thirds is still unspent.”
Milich: Skiff Cannot Generate Significant Revenue Without Millions of Users
“But the kind of most important thing is like, we just cannot, we'll never generate significant revenue if we don't Reach millions of users.”
Milich: Skiff has 15 to 20 full-time employees globally
“So we're about 15, 15 to 20 all over the world. Bunch in the Bay Area, some in New York, some in France, some in Israel, some in Hungary and Egypt and, you know, the rest of the world.”
Milich: Product-led growth appears flat before compounding vertically
“Product like growth, I think is very difficult and also very time consuming as in like, you will not see thousands of users immediately signing up. Like the whole point of like compounding growth is, you know, it'll look flat and then you look back and it look…”