This seems odd to me, given that he looks (from the outside at least) to be one of the most ambitious CEO's around. E.g. Building a fulfilment network to compete with Amazon.

Can I ask what your source for this is? Perhaps you're an ex-employee?

I never worked under Tobi directly (or even close), but I was almost always thoroughly impressed with his communication and direction. I think I have a totally different take than the one you stated. The only axis I could see Elon & Tobi both sitting on is being members of the tres comas club.

Externally he has a personal writer whose whole job it is to make him seem smart. He's the darling of the Canadian tech industry, which badly needed a win since the implosion of Nortel, so he has a ton of advantages. In SV he would be a mediocre wannabe founder but in Ottawa he's hot shit.

That seems disingenuous at best—the man helped create Ruby on Rails & founded a mutli-billion dollar tech startup that has been wildly successful. Is there really any ground to question his intelligence, or rather, whether or not he's smart?

Tobi is cool as fuck.

Your experience reminds me of the saying, sometimes "the best people to work WITH are the worst people to work FOR".

This reminds me of SNL's Undercover Boss Starkiller Base ~ Kylo Ren

https://www.youtube.com/watch?v=FaOSCASqLsE

Kylo Ren as Matt: "He said Kylo Ren has an 8-pack. That Kylo Ren is shredded."

* * *

Not OP, but I worked for Tobi when I was at Shopify. He is indeed cool as fuck.

Classic Canadian spirit. Ambition is never on the charts. Anybody who comes to Canada gets steeped in lethargy and sloth.

So classic german-canadian spirit: I will do it perfectly ... tomorrow.

Ooof I sense a juicy backstory here

Not really, I come from a similar country. If you’re ambitious – move to the US or UK, if you want balanced lifestyle – stay and don’t work too hard.

Aussie?

Tobi still actively works on project within Shopify.

I've worked on projects within the last year that had (pretty heavy) direct involvement from Tobi.

Paging @xal

/s