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).
>“… all wear green,” said a soft but very distinct voice, beginning in the middle of a sentence, “and Delta Children wear khaki. Oh no, I don’t want to play with Delta children. And Epsilons are still worse. They’re too stupid to be able to read or write. Besides they wear black, which is such a beastly colour. I’m so glad I’m a Beta.”
>There was a pause; then the voice began again.
>“Alpha children wear grey. They work much harder than we do, because they’re so frightfully clever. I’m really awfuly glad I’m a Beta, because I don’t work so hard. And then we are much better than the Gammas and Deltas. Gammas are stupid. They all wear green, and Delta children wear khaki. Oh no, I don’t want to play with Delta children. And Epsilons are still worse. They’re too stupid to be able …”
The only thing I think a lot about is advancing at work and saving up for a bigger home.
Whenever I stop up to appreciate both my current working and living conditions, I’m happy for that period of time.
Yet, if I’m content, I’ll never live somewhere else doing something harder. I’d rather be a little unhappier always if I can think of ways to advance in the minigames I favor.
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.
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.
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.
I've no issue with this being discussed here. I welcome it.
I can't find you a list of showdead. They're unlisted and Algolia doesn't preserve them. I see them because I subscribe to a 50+ score RSS feed. I regularly see popular posts flagged off the home page for what appears to be partisan reasons, but is often justified as "non technical".
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).