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).