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Ask HN: Entrepreneurs, how long did it take you to succeed?

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TL;DR · WeSearch summary

The entrepreneur shares their journey of building multiple businesses over two decades. After selling Staff Squared in 2022 and Fundipedia in 2025, they are now focusing on angel investing and consulting. They plan to document their experiences on their personal website in the coming months.

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Ycombinator
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Record

Original publisherYcombinator
Canonical URLhttps://news.ycombinator.com/item?id=48315206
Publication timeThu, 28 May 2026 20:45:28 +0000
Retrieval time2026-05-28T20:54:38.012Z
Last seen2026-05-28T20:54:38.012Z
Headline sourcePublisher (no WeSearch rewrite)
Excerpt sourcepublisher body
Excerpt methodFirst ~120 words (~800 chars) of extracted publisher body, fair-use limited.
SummaryWeSearch · cerebras-chat (WeSearch summarizer)
Summary source textcontentText
Citation coverageSummary is a WeSearch-generated derivative; primary citation is the original publisher URL.
ClusterNACeKlXXYHUH · 2 stories
Cluster logicGrouped by semantic title/content similarity across sources within a rolling window. Same-publisher template collisions are excluded from coverage comparison.
Ranking reasonStory pages are not engagement-ranked. Hub feeds use recency, with optional source-diversified chronological ordering (cap consecutive stories per source). No personalized ranking.
Publisher visitYes — open original
Substitutes article?No — link-out required for full text

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Machine-readable
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WeSearch interpretation
WeSearch declared handling (basis: Derived from the published RSS/Atom feed). This is WeSearch policy, not a legal grant on the publisher's behalf.
Unknown
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WeSearch handling by dimension

Indexing May the item be indexed (stored, ranked, made findable)? Allowed
Snippet May a short excerpt of the publisher's text be shown? Allowed
AI summary May WeSearch generate its own short summary of the article? Limited
Retrieval / RAG May the content be exposed for third-party retrieval-augmented generation? Not asserted
Model training May the content be used to train AI models? Not asserted
Commercial reuse May the content be reused commercially? Not permitted

Basis: Derived from the published RSS/Atom feed. Contact: [email protected]. Reviewed: 2026-07-24.

Opening excerpt (first ~120 words) tap to expand

It took me about ten businesses and over 20 years to "succeed". I wanted to retire at 35 for as long as I could remember, missed that by 7 years.Sold Staff Squared in 2022 for a good sum (7 figure), reinvested most of it into Fundipedia.Sold Fundipedia for life changing (8 figure) sum in 2025.All businesses were bootstrapped, reinvesting profits to grow them organically.I'm now angel investing and consulting. I'm posting more about my journey on my personal website over the coming months https://www.simonswords.comRough timeline:2000 - started a computer hardware company called Atlas alongside a speed dating company (that's not a joke, I ran a speed dating company and some other weird businesses).2002 - switched Atlas to designing websites, stopped selling hardware and associated support…

Excerpt limited to ~120 words for fair-use compliance. The full article is at Ycombinator.

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