Gail Borden, Founder Borden's Eagle Brand Sweetened Condensed Milk (1801-1874)

Gail Borden was a failed serial entrepreneur until finally he succeeded. His success was based on two strokes of good luck:

1) Jeremiah Millbank, a wealthy financier, took a shine to Borden and his passion for manufacturing condensed milk on a random train ride. Borden was down to his last nickel, and had lost everything in his repeated attempts to monetize his innovations; and

2) the Union Army decided Borden's struggling brand was exactly what it needed to get calories to troops on the front line. 

Borden's story, aside from his last-minute success against all odds, bears striking similarities to today's sad sage of entrepreneurial failure: Theranos, the blood-testing start-up that was valued at $9 billion before it was exposed as a fraud.

Elizabeth Holmes, Theranos Founder (1984-)

Both Borden and the Theranos founder, Elizabeth Holmes, spoke evangelically about the potential of their products to make the world a better place for the average consumer. Borden's milk would keep babies from dying of tainted milk, and Holmes' blood-analyzing technology could be deployed inexpensively and rapidly in any environment, from the home, to Walgreens, to the battlefield.

Both convinced hugely rich and influential backers of the urgency and viability of their visions.

And both got strong endorsements from the military, which badly wanted their products. The only difference: Borden's technology worked.

Borden left a string of failed innovation attempts behind him, not the least of which was the meat bar, which today has finally found its moment. Often, it's all a matter of timing. If only Holmes had had less pressure, more time, better luck.....As many a failed entrepreneur knows, if only........