They were never losing that much cash, and they have recently become cash flow positive, https://www.macrotrends.net/stocks/charts/TWLO/twilio/price-...

The large GAAP loses comes from dilution – mostly in the form of stock based comp. In theory if growth exceeds dilution then investors are still owning an appreciating asset, and if the stock is richly valued (as TWLO was) then it makes sense to fund that growth with capital rather than debt.

But yeah, as a shareholder I felt their stock based comp was egregiously high and it took management a little too long to realise we're in a new world and things needed to change... A side point, but that's actually why I invested in TWLO because the stock got so beat up and their SBC was so excessive that it was kinda obvious that things were going to need to change and the market would react to that positively.

The markets seem to be reacting favourably to this news and again I think that's because there was an assumption that Jeff Lawson was largely to blame for the lack of focus on profit optimisation.

Personally I think Jeff is a great CEO though and I didn't want to see him go. I just wanted him to make some tough decisions to stop the burn – which more recently he seemed to be doing. While I do think they need to be more finance minded in this next stage of the business, I would doubt whether a developer focused tech company like Twilio will benefit much from a managerial leader like Shipchandler. We've seen this mistake made repeatedly by tech companies in the past.