Max Levchin may still be most well-known as a member of the founding "PayPal Mafia," but that payments company is just one of his many entrepreneurial efforts. "I started four companies before PayPal, and they all failed one way or another," says Levchin, now the co-founder and CEO of lending startup Affirm. "It sucks when you fail ... but I was so caught up in the whole [excitement of] starting companies in rural Illinois, that none of it was too difficult."

PayPal's success significantly changed that track record, of course. Now Levchin is attacking another part of the staid financial services industry, trying to make retailer-specific credit more transparent and Millennial-friendly. In a recent conversation, edited and condensed below, Levchin spoke about one of his earliest business breakups--and how that helped him grow into his founder confidence.

I'm fairly black-and-white about everything. It's probably a product of my socialist upbringing.

And it's probably a shortcoming as opposed to an advantage--but I'm now comfortable enough with my black-and-white self to realize that that's how I'm going to operate. Even if as a result, I sometimes blow through opportunities.

 inline image

I didn't always accept that about myself--which, when I was younger, was something that resulted in a very unpleasant founder divorce. There was some money involved, and it basically destroyed a relationship with someone who was maybe a very fine human being.

There was just enough of a personality and stylistic difference between us; I was black-and-white, and this type of person seemed a lot more sophisticated in understanding how the world works than I was. So when we were figuring out the distribution of stock, I wanted a 50-50 split, but his view of the world was, "I bring something to the table and you bring something to the table, and they're different things."

I was kind of flabbergasted--how could you not have a 50-50 partnership? That wasn't the thing that blew it all up, but it was the first sign that we probably didn't value things the same way. I let it go at first, and kept on working...but at some point I woke up and thought, "This is a startup. It's like war, and you don't want to be in a foxhole with someone who doesn't have the same view of everything."

Now, when I counsel entrepreneurs, I advise them: "If the equity split isn't 50-50, do you have the right partners?" You want everyone to have the same level of investment.

And the advice I would have for my younger self is: Just be comfortable with who you are. Your black-and-white view of things may be an advantage or it may be a disadvantage. But that's who you are.