Evidence on some parts of the prediction is directional but the core claim about free cash flow is not verifiable now that Zendesk is private.

What we can see:

• Deal happened as described. Zendesk was acquired by a Hellman & Friedman / Permira–led consortium for about $10.2B and taken private in November 2022, shortly after the podcast. (en.wikipedia.org)

• Revenue growth did slow materially. Public and secondary data sources agree on roughly:

  • 2021 revenue ≈ $1.34B, growing ~30% YoY (pre‑buyout). (getlatka.com)
  • 2022 ≈ $1.58B (~18% growth), 2023 ≈ $1.75–1.9B (~11–16% growth depending on source), 2024 ≈ $1.93B (~10% growth). (getlatka.com)
    Over 2021–2024, this implies a revenue CAGR of ~13%, i.e., a clear slowdown from ~30%. That’s directionally consistent with Chamath’s claim that growth would be pulled down, but it ended up below his 15–20% range rather than inside it.

• There has been some cost cutting, but not clearly "slashing" R&D and S&M.

  • Zendesk cut about 5% of staff (~300 employees) in November 2022 explicitly for cost optimization, and later announced a smaller layoff (51 employees in SF) in 2025. (sfchronicle.com)
  • At the same time, the company is investing in growth initiatives like a major Austin office that it describes as a “go-to-market hub” with sales, engineering, marketing and support roles, and plans to expand that location from ~300 to ~500 employees. (statesman.com)
  • Some secondary write‑ups say adjusted EBITDA margins “have improved to approximately 12%” post‑privatization, implying improved profitability but still modest margins for a SaaS LBO. (grokipedia.com)
    Overall, this looks like typical PE efficiency work (moderate headcount cuts, price increases, focus on AI/enterprise) rather than an obviously radical shutdown of R&D and sales & marketing.

• Pre‑buyout free cash flow was far from his $300–500M target. Public filings and data aggregators show trailing‑twelve‑month free cash flow around the time of the deal at roughly $95M on ~$1.59B of revenue (≈6% FCF margin), with historical FCF margins mostly in the mid‑single to low‑double digits. (discountingcashflows.com) That’s well below the $300–500M he envisioned, but those figures stop at Q3 2022 (right before going fully private).

What we cannot see (and why this is ambiguous):

• After November 2022, Zendesk no longer files detailed financials, so there is no authoritative public data on:
  • Actual free cash flow in 2023–2025 (his key numerical claim was $300–500M in annual FCF).
  • Exact R&D and sales & marketing spend levels or their percentage of revenue post‑buyout.
• Third‑party sites and AI/consulting write‑ups that give 2023–2024 revenue and margin estimates appear to rely on company marketing materials or modeled estimates, not audited statements; none credibly report free cash flow in the $300–500M range, but they also don’t rule it out explicitly. (getlatka.com)

Because the centerpiece of Chamath’s prediction—the ability to generate $300–500M in annual free cash flow on roughly today’s revenue base—depends on private, unreported cash‑flow numbers, we cannot definitively say whether that part came true. We can confirm the growth slowdown and some cost optimization, but not the magnitude of profitability he forecast.

Given that enough time has passed but the relevant post‑LBO cash‑flow data is not publicly knowable, the fairest label for this prediction as stated is "ambiguous" rather than clearly right or wrong.