The very first company I started failed with a great bang. The second one failed a little bit less, but still failed. The third one, you know, proper failed, but it was kind of okay. I recovered quickly. Number four almost didn’t fail. It still didn’t really feel great, but it did okay. Number five was PayPal.

Levchin frames entrepreneurial success as the cumulative product of repeated, increasingly instructive failures. By narrating a sequence—each venture failing “less” until PayPal—he emphasizes iteration, resilience, and learning-by-doing rather than innate genius or a single breakthrough idea. The casual, conversational phrasing (“proper failed,” “kind of okay”) also demystifies startup mythology: progress is uneven, emotionally taxing, and often only recognizable in hindsight. The quote functions as a corrective to survivorship bias, suggesting that what looks like sudden success is frequently the fifth attempt built on the hard-won lessons of the first four.