I was wondering if I qualified for the Entrepreneur Relief?
You haven't mentioned what the company does. That's the starting point.
We'll presume it meets the 'Qualifying Business' condition i.e. a business other than the holding of securities or other assets as investments; the holding of development land, or the development or letting of land.
The fact that you held less than 5% at the time of disposal shouldn't disqualify you from the relief.
The requirement for an individual to have owned a holding of at least 5% of the ordinary share capital for a continuous period of 3 years in the 5 years immediately prior to the disposal was amended by section 24 Finance Act 2020, so that the shares can qualify for relief if they were held for a continuous period of 3 years
at any time prior to the disposal of those shares. If you held at least 5% of the ordinary share capital for 3 years you will be regarded as a relevant individual and the shares will be 'chargeable business assets'. The subsequent dilutions down to 2.1% shouldn't matter if you had 5% for 3 years at any point.
What's considered 5%? It is unclear from the legislation whether the 5% threshold should be calculated by reference to the nominal value of shares or the number of shares in issue; however, Revenue guidance clarifies that “it is the nominal value of the ordinary shares issued rather than the number of such shares that is relevant” in paragraph 2b.4 of the
Tax & Duty Manual on Entrepreneur Relief.
However, the 'Qualifying Person' condition could trip you up here i.e. the requirement to spend not less than 50% of your working time in the service of the company in a managerial or technical capacity, and served in that capacity for a continuous period of 3 yrs in the 5-yr period immediately prior to the disposal. Based on the info provided, this condition may not be met but as I've hopefully given you a glimpse at the complexities of the relief, specialist advice would be no harm.