Could he have sold the shares so that he could then buy them back in 30 days in his TFSA so that the anticpated future (hopefully dramatic) growth wouldn't be taxable? By selling from his investment account and waiting 30 days he can then buy in his TFSA and claim the loss. If he just transferred into the TFSA he couldn't claim the loss. Hopefully it wasn't because he needed he money. If he needed the money he could have arranged a cheap tax deductible bridge loan for this small amount and used his other shares as collateral. There has to be some reasonable explanation like the tFSA swap above. He is probably one of the most optimistic of the team for having put 30 years into this and now seeing some real practical applications coming to life inside a company he helped found and build. I hope he gets a huge financial and personal reward for his sacrifies, genius and persaverance.
