Wall of Failure — IASV OS

Companies we passed on that went on to succeed. Every miss is a lesson — we track them openly so we get better.

Massive: 2

Large: 1

Total: 3

Company	We Passed	What Happened	Magnitude	Lesson
Rippling	Sep 2020	Passed on Rippling's Series B at a $1.35B valuation. The company reached a $13.5B valuation by 2023 and is building a unified workforce management platform that combines HR, IT, and Finance.	Large	Dismissed it as another HR SaaS competitor to Gusto and Workday. Missed that Parker Conrad was executing on a genuine compound startup strategy — each module creates defensible data moats for the next. Founder pedigree after Zenefits should have earned more credit, not less.
Notion	Jun 2019	Passed at seed in mid-2019. Notion raised their Series A in 2020 at a $2B valuation and grew to over $10B by 2021. Now one of the defining productivity tools of the decade.	Massive	All-in-one workspace tools looked crowded (Confluence, Google Docs, Dropbox Paper). Missed that Notion's block-based flexibility created a fundamentally new category. Team quality and product obsession should have outweighed market-overlap concerns.
Figma	Mar 2018	Evaluated Figma in early 2018 and passed, believing Sketch had the design tool market locked up. Adobe acquired Figma in 2022 for $20B — the largest design software acquisition ever.	Massive	Browser-based collaborative design was a genuine platform shift, not just feature parity. Sketch's desktop-only moat was fragile. Real-time multiplayer in creative tools was massively undervalued.

Rippling

Passed Sep 2020

Large

Passed on Rippling's Series B at a $1.35B valuation. The company reached a $13.5B valuation by 2023 and is building a unified workforce management platform that combines HR, IT, and Finance.

Lesson

Dismissed it as another HR SaaS competitor to Gusto and Workday. Missed that Parker Conrad was executing on a genuine compound startup strategy — each module creates defensible data moats for the next. Founder pedigree after Zenefits should have earned more credit, not less.

Notion

Passed Jun 2019

Massive

Passed at seed in mid-2019. Notion raised their Series A in 2020 at a $2B valuation and grew to over $10B by 2021. Now one of the defining productivity tools of the decade.

Lesson

All-in-one workspace tools looked crowded (Confluence, Google Docs, Dropbox Paper). Missed that Notion's block-based flexibility created a fundamentally new category. Team quality and product obsession should have outweighed market-overlap concerns.

Figma

Passed Mar 2018

Massive

Evaluated Figma in early 2018 and passed, believing Sketch had the design tool market locked up. Adobe acquired Figma in 2022 for $20B — the largest design software acquisition ever.

Lesson

Browser-based collaborative design was a genuine platform shift, not just feature parity. Sketch's desktop-only moat was fragile. Real-time multiplayer in creative tools was massively undervalued.