$ZM the most asymmetric bet on Anthropic/AI. You get the core business basically for free
u/Zeneph007 ·
Reddit — r/ValueInvesting
· April 23, 2026 at 23:13
· ⬆ 45 pts
· 💬 27 comments
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Summary
The post argues that Zoom (ZM) is deeply undervalued because its market cap (~$25B) is only slightly above its cash ($7.8B) plus an estimated $10B stake in Anthropic, leaving its core enterprise video business at a ~3x EV/FCF multiple.
The author views ZM as an asymmetric bet: a cash‑generating core business with a “free” AI moonshot via its early Anthropic investment, which could re‑rate as Anthropic approaches a rumored IPO.
The analysis is well‑researched but depends on secondary‑market valuation of Anthropic ($1T) and assumptions about dilution; it blends fundamental value with speculative AI proxy logic.
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I know, I know. "Zoom? That's a 2020 pandemic relic, right?" That’s exactly what the market wants you to think while it ignores one of the most insane valuation disconnects in tech right now.
If you look at the math, $ZM it’s a massive pile of cash and a "hidden" AI moonshot that the market is valuing at almost zero.
Most people don’t realize Zoom was an early strategic investor in Anthropic back in May 2023.
The Entry: Zoom invested roughly $51M when Anthropic was valued at just $4.5B.
The Current Reality: As of this week (April 2026), Anthropic’s implied valuation on secondary markets (like Forge Global) has touched $1 Trillion, officially overtaking OpenAI.
The Math: Even accounting for heavy dilution from Anthropic’s massive Series G and recent funding rounds, a \\\~1% stake in a $1T company is worth $10 Billion.
2. The $8B Cash Fortress
Zoom is sitting on $7.8 Billion in cash and short-term investments with zero debt.
They generate roughly 1.7B - $1.9B in Free Cash Flow (FCF) annually.
They aren't burning money to grow; they are a cash-printing machine that just happens to have a video app.
3. The "Free" Business Logic
Let’s do the "back of the napkin" math on the valuation:
Current Market Cap: \~$25 Billion
Minus Cash: -$7.8 Billion
Minus Anthropic Stake (Estimated): -$10 Billion (conservative adj. for liquidity)
Remaining Enterprise Value (EV): $7.2 Billion
The market is saying Zoom’s core business—which generates $5 Billion in annual revenue and has 75%+ gross margins—is only worth $7.2B.
That is an EV/FCF multiple of roughly 3x
For context, legacy "dying" businesses usually trade at 8-10x. Zoom is being priced like it's going bankrupt tomorrow, despite having a massive enterprise moat and a dominant seat at the AI table via their Claude integration.
4. The Catalyst: The "AI Proxy" Play
As Anthropic prepares for an IPO (rumored for late 2026), investors are going to look for ways to get exposure. You can't buy Anthropic on yet but you can buy the company that owns a multi-billion dollar piece of it.
When the market realizes they are essentially getting a global enterprise software leader for a 3x multiple—plus a lottery ticket to the world's most valuable AI startup—the re-rating is going to be violent.
TL;DR: You’re buying $17.8B in "hard" assets (Cash + Anthropic) for $25B. You’re paying $7B for a business that nets $1.7B a year. It’s a crazy margin of safety.
Not financial advice. I like the stock and the math.
Zoom holds ~$7.8B cash/debt-free and owns a ~1% stake in Anthropic valued at ~$10B on secondary markets; its core business generates ~$1.7B FCF on $5B revenue. The market effectively prices the core business at a ~3x FCF multiple, implying extreme pessimism. A catalyst (Anthropic IPO or market re‑rating) could compress that gap violently. Buy ZM for a hard‑asset floor ($17.8B cash+stake) plus a free, profitable enterprise business; the asymmetric payoff favors upside if AI sentiment improves. Anthropic’s secondary valuation may be illiquid or overstated; core Zoom revenue could decline due to competition (Teams, Google Meet); IPO may be delayed or fail to materialize.