Raised in a household that prioritized the stability of government jobs and low-risk investments, Kerpen spent her early adulthood clinging to the safety nets her parents had championed. It was only when the reality of an unhappy marriage became more daunting than the uncertainty of divorce that she began to view risk as a survival mechanism rather than a threat. This shift in perspective eventually redefined her professional trajectory.
When her second husband expressed a desire for a lavish wedding, Kerpen sought a creative solution that wouldn't drain their finances. She approached a minor-league baseball team to rent their stadium and aggressively courted sponsors to cover the $125,000 costs. What was initially an unconventional way to fund a ceremony turned into a proof-of-concept for her future business, Likeable. The media company grew rapidly, eventually leading to a lucrative exit in 2020.
Now an advocate for calculated risk-taking, Kerpen teaches other female founders to move past the paralysis of uncertainty. Her methodology is simple: evaluate both the best and worst-case outcomes. If the worst-case scenario is manageable, the risk is worth taking. She encourages her own children to adopt this mindset, urging them to embrace volatility while they have the time to self-correct, rather than settling for the hollow comfort of a secure, predictable life.
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