Afford Anything | Make Smart Choices About Your Money, Time And Productivity

#675: Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E. Today’s letter E stands for Entrepreneurship. This episode originally aired in September 2018, at a moment when startup culture was loud, venture capital was abundant, and entrepreneurship was often framed as something that involves outside investors and rapid growth. ____ In this episode, we rewind the clock to 2018. Remember what entrepreneurship was supposed to look like back then? Build a startup. Raise capital. Scale fast. Get rich. That was the dominant story. But our guest, Rand Fishkin, told a different story – a story about founder burnout, debt, and the downside of startup culture. Rand, the founder of Moz, shares how he and his mother accumulated nearly half a million dollars in debt while running an early services business. He talks about what it felt like to face creditors, negotiate settlements, and keep going under intense financial pressure. From there, we move into one of the