Just part of a pattern if it is Barry selling. His highly successful strategy seems to be to get in on the ground floor - well actually a level below basement prices in reality.
Given the number of unquoteds that fail then it can only be a successful approach for those that have a highly sensitive nose regarding unlisted start-ups that are going to make it. I think 99% of investors would flounder but Barry thrives on it because he has a rare - perhaps unique - combination of business, sales and engineering skills. So he can spot a blue sky, saleable and commercially solid idea. The third part of the criteria isn't essential as the dream is sold and good profits can be made before knowing if the dream is going to a commercially successful reality.
Where the approach may fail is in the future if people who follow him in secondary fundings decide that it is not worthwhile doing so because their investment will take a beating when he or close associates bail out early on in size without getting a matched buyer for all the stock at the prevailing market price. Barry was never afraid to take a profit with BPRG, Voller and now perhaps Cyan and good luck to him.
Aside from short-term nuiscance fluctuations any early selling isn't enormously signficant. What's important is if the business shows early signs of being a commercial success. Cyan are sufficiently funded for the business to have time to show whether it can be a success and bring in some decent orders. If it does that then it will be a multi-bagger. I'd suggest, however, that based on past history, Ormston Gore is likely to go under 3% at some stage.
Barry would have made a good football manager in the transfer wheeling and dealing days. Nick a few bargains from the conference and then sell them on for a multiple of the purchase price. Of course the player might go on to international honours and multiply in value again but it's not a bad strategy for those that can do it.