tax on shares paid by company

[fefeto]

Hope someone can help with my case. I started part time/freelance work as CTO for a small start up about two years ago. At the time the company couldn't pay salary as no revenue and was living on angel investor's cash. The angel investor put in 160K for 30% of the company, which value the company at 533k. The deal with me was 2.5% of company shares for every six months service until reach 7.5% in total. There is a potential for extra 2.5% top up as well. Now the company run out angel's fund and the second around funding is almost in place. The second round funding will be 500k for 30% which values the company at 1.5M. At this stage the company is still no revenue. anyway, the founder told me my shares (currently 7.5%) is under his name and he is happy to transfer to me any time. Also he is happy to top up the 2.5% when I join the company full time. So here are my questions:

1. if the founder transfers the shares tomorrow, do I need to pay any tax at all. The reason for asking is I am currently a high tax payer. Also paying tax on something hasn't got a clear future doesn't sound very well. what's the best way I could take those shares in tax efficient way?

2. this questions is due to the second funding round. The new cash injection will bring my shares down to 5% and any new funding round will bring it below 5% which disqualify me from Entrepreneurs' Relief. I know even the company succeed, it would require another round of funding. The founder offered 2.5% top up when I am on full time which is nice. But it might not be suitable for me to go full time with them. What's the best way to protect myself in this case?

Thanks in advance for any help on this.

Regards,

[LozaACCS]

There are complex issues here involving both legal and tax aspects, you should seek formal advice, however I would offer the following observations from the information provided.
You indicate that shares will be issued (or more likely transferred to you) it is important that you clarify this since if new shares are issued by the employer there are likely to be PAYE implications when the shares become due to you.
If however the shares are transferred from the existing holder (the founder) then CGT is more likely to be in point, if however the founder held those shares from the outset as a nominee to advance to you when the conditions are met for allocation then income tax would again be in point, the shares would be restricted securities since conditions are involved on when and if you become entitled to the shares.
I would reiterate the need for formal advice