His Father/Family had a net worth of $250M https://en.wikipedia.org/wiki/Fred_Trump

It's estimated he Inherited $40M http://www.politifact.com/florida/article/2016/mar/07/did-do...

Trump himself claims he started off with "a small loan of 1 million dollars" https://youtu.be/mkKBXJRySFw?t=20s

The famous quote from Trump himself is "My father gave me a small loan of $1 Million dollars" (around 0:40 in this video):

https://www.youtube.com/watch?v=TXEOFHf1q9A

On the other hand, that's less than the investment funding I've seen to some folks on HN, and it's the same amount of capital that would be required if you wanted to open a McDonald's store [1]. But I think a majority of people would regard that as starting from a wealthy position, and certainly not bootstrapping anyway.

[1] https://www.franchisehelp.com/franchises/mcdonalds/

Don't forget that $1 Million at that point in time is different than $1 Million now.

Good point. As far as I can tell the loan must have been around 1968 - 1971, and this inflation calculator [1] puts that at $7 Million in today's money.

[1] http://www.usinflationcalculator.com/