Stock price when the opinion was issued
Pay attention to the old highs (~$200), and stock's getting close to them. Recent peak does appear to be breaking the last one. Probably will get to the $200 area, so still a few bucks to go. From there, that's when to start chewing your nails, as it's stalled there before when those old buyers just want their money back.
A tough one. Lots of speculation in the name. If you look at it with a purely quantitative view, you'd be a bit nervous. Still in the high growth, ramping up operations, risky "startup" phase. Improving ROC. Valuation makes him pause.
Doesn't have a problem owning it, but should not be core. If your portfolio has 20 stocks, 5% each, then this one should only be ~2%. With today's earnings pop, good to trim.
Great run. If you believe that e-commerce retail has a lot of legs (which he does), there are other ways to express that view. SHOP is stuck in the middle. Doubled off bottom, but faces structural issues of having to go up-market to enterprise customers, and AMZN is already there.
Moving up from micro-merchant is easier said than done. Being the UI layer and the feature layer is the most vulnerable part of the value chain that is global e-commerce. Tactically, he'd own AMZN.