From the beginning Tesla and SpaceX were in dire straits; nobody took them seriously. At the start he thought Tesla maybe had a 10% chance of success, and he was close to a nervous breakdown before Christmas 2008.
"for the beginning we were in in really Dire Straits"
He never thought Tesla would succeed from the beginning — maybe 10–20% odds; at the end of 2008 it looked like failure and he put in his last money, closing financing on Christmas Eve 2008 at 6 p.m.
"I actually thought we would fail"
When he started SpaceX he thought the odds of success were very low and they would most likely fail, but they should give it a try anyway.
"When I started SpaceX, I thought the odds of success were very low"
The Mars-greenhouse idea would have been a 100% chance of losing the money. SpaceX, which he thought maybe had a 10% chance of success, was an improvement.
"SpaceX, which I thought maybe had a 10% chance of success"
The Tesla round closed 6 p.m. Christmas Eve 2008, last hour of the last possible day; they would have gone bankrupt about two days after Christmas otherwise.
"we would have gone bankrupt like 2 days after Christmas"
He thought success was maybe 10% likely; both companies nearly failed in 2008 after three SpaceX launch failures and a Tesla financing round that closed Christmas Eve.
"we came very close to both companies not succeeding in 2008"
The real key was 2008, or mid-2007 to mid-2009: a super-bad two years, almost every early Tesla decision wrong, company almost completely recapitalized in 2007.
"that two-year period was super bad"
When they first started Tesla and SolarCity they thought they would fail. Tesla in particular he thought maybe a 10% chance of success. Cars are one of the worst risk-adjusted returns.
"maybe 10% chance of success"
Probability of success was so low he provided all the money from PayPal into Tesla, SolarCity and SpaceX. For Tesla they closed the financing round on Christmas Eve 2008, the last hour of the last day possible. Even as recently as early 2013 they were operating with maybe one to two weeks of money.
"we actually closed the financing round on Christmas Eve uh 2008"