Hacker News: simonswords82

New comment by simonswords82 in "Ask HN: Entrepreneurs, how long did it take you to succeed?"

simonswords82 — Thu, 28 May 2026 22:02:28 +0000

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.com

Rough 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 - fed up with call outs to fix networks at the weekend.

2004 - started to design AND code websites, grew Atlas out as a custom software shop - had about 10 employees. Made about 10% margin on a good year. Tough business.

Around 2006 - Vowed to find ARR working with our team on various software solution ideas.

2007 - built first version of what would become Fundipedia - a data management platform for buy side asset managers e.g. HSBC/Barclays/LGIM etc.

2011 - got fed up with internal HR admin as we took on more staff. Built internal HR/time off tracking system that would eventually become Staff Squared - a SaaS HR solution for small businesses.

2012 - 2016 - ran Atlas, Fundipedia and Staff Squared - not very well, but never made a mistake that killed these businesses. Although it nearly killed me - super stressful.

2017 - Fundipedia showed signs of promise as clients were coming to us via word of mouth - we did not market it at all. So I put a plan in place to grow Fundipedia and take on challenge of learning more about the asset management space.

2021 - landed massive Fundipedia client. Sold Staff Squared to a private buyer, wound down Atlas clients.

2025 - With Fundipedia leading the sector it was in - busting the rule of 40 it was now a real threat and an opportunity to our larger competitors in the space. I sold to FE FundInfo (who backed by Hg Capital).

New comment by simonswords82 in "New gel restores dental enamel and could revolutionise tooth repair"

simonswords82 — Wed, 05 Nov 2025 19:58:15 +0000

Where? Source please?

New comment by simonswords82 in "Why aren't smart people happier?"

simonswords82 — Wed, 05 Nov 2025 19:53:12 +0000

I think most of us are hard wired to progress - progression looks different for each of us but matters all the same.

I've also had side quests in addition to my main quest which is financial stability and the extreme and total control of my circumstances. Side quests are hobbies, friendships, fitness targets etc.

New comment by simonswords82 in "Why aren't smart people happier?"

simonswords82 — Wed, 05 Nov 2025 19:38:51 +0000

I love this line from a 2024 TV show called "The Gentlemen" and I think about it a lot:

"It’s a lucky man who is happy with his place in life"

https://en.wikipedia.org/wiki/The_Gentlemen_(2024_TV_series)

Most Gen AI Players Remain 'Far Away' from Profiting: Interview with Andy Wu

simonswords82 — Tue, 04 Nov 2025 20:00:33 +0000

Article URL: https://www.library.hbs.edu/working-knowledge/many-gen-ai-players-remain-far-away-from-profiting-interview-with-andy-wu

Comments URL: https://news.ycombinator.com/item?id=45815264

Points: 4

# Comments: 1

New comment by simonswords82 in "Taking money off the table"

simonswords82 — Thu, 30 Oct 2025 22:24:15 +0000

AKA quit while you're ahead

New comment by simonswords82 in "Five years as a startup CTO: How, why, and was it worth it? (2024)"

simonswords82 — Sat, 04 Oct 2025 19:24:23 +0000

Yes! That’s exactly what we’re doing. It’s not as easy as it sounds.

New comment by simonswords82 in "Ask HN: What are you working on? (July 2025)"

simonswords82 — Sun, 27 Jul 2025 19:31:46 +0000

Just sold my data management software business https://www.fundipedia.com.

Now bootstrapping https://www.minute-master.com - AI formal minute generation for regulated firms primarily in financial services space but also free to use for charities.

New comment by simonswords82 in "Scottie Scheffler raised questions about happiness and fulfillment"

simonswords82 — Wed, 23 Jul 2025 17:40:53 +0000

https://archive.is/FGu4h

New comment by simonswords82 in "India launches attack on 9 sites in Pakistan and Pakistani Jammu and Kashmir"

simonswords82 — Wed, 07 May 2025 11:14:06 +0000

I was going to say the opposite. Seems on all the main news outlets (Financial Times et al) have disabled comments. I was happy to see this being discussed on HN and I’ve yet to see Middle East or Trump being censored but happy to be signposted to evidence of this on HN.

New comment by simonswords82 in "How much are LLMs boosting real-world programmer productivity?"

simonswords82 — Sat, 08 Mar 2025 20:37:08 +0000

Without over complicating it, using AI is currently about 4x productivity in mid to senior developers.

New comment by simonswords82 in "Executive wealth as a factor in return-to-office"

simonswords82 — Sun, 02 Mar 2025 18:52:40 +0000

Good on this guy for having the courage to be honest about his circumstances. Still, shitty that this is the situation.

New comment by simonswords82 in "Zelensky leaves White House after angry meeting"

simonswords82 — Fri, 28 Feb 2025 20:44:22 +0000

Weird in what way?

New comment by simonswords82 in "Zelensky leaves White House after angry meeting"

simonswords82 — Fri, 28 Feb 2025 20:29:43 +0000

@dang perhaps you could pin https://u24.gov.ua/ to the top of the comments?

Either way, I've donated 50 bucks; seems like a great way to show support on a difficult day for Ukraine.

New comment by simonswords82 in "Richard Feynman's blackboard at the time of his death (1988)"

simonswords82 — Fri, 21 Feb 2025 21:30:55 +0000

Seriously? That is so cool that you were there. Sad that we lost him fairly young. Such a legend, I love his work.

New comment by simonswords82 in "Grim Fandango Puzzle Document (1996) [pdf]"

simonswords82 — Wed, 19 Feb 2025 10:32:03 +0000

I’d just like to say thank you from the bottom of my heart for making my childhood and engagement with computers all that more magical. I went on the make a career and a livelihood from them and games like yours shaped me.

You guys must have impacted thousands upon thousands of lives with your hard work and creativity.

New comment by simonswords82 in "Starship Flight 7"

simonswords82 — Thu, 16 Jan 2025 21:41:03 +0000

This NASASpaceflight stream is up now: https://www.youtube.com/live/3nM3vGdanpw

New comment by simonswords82 in "I am rich and have no idea what to do"

simonswords82 — Fri, 03 Jan 2025 16:13:25 +0000

If true, he probably knows this already and now just needs to work out how to fix it.

New comment by simonswords82 in "I am rich and have no idea what to do"

simonswords82 — Fri, 03 Jan 2025 16:10:59 +0000

Contact your local university, most have mentorship programmes you can apply to be a part of for under and post grads.

New comment by simonswords82 in "Ask HN: What's Your Morning Routine?"

simonswords82 — Thu, 02 Jan 2025 20:02:16 +0000

Spotted the Brit!