I raised $125,000 in sponsorships for my wedding. It accidentally launched an 8-figure business.

Carrie Kerpen's parents encouraged her to pursue a career she loved, as long as it was stable. They were risk-averse and taught her the same. Carrie gradually became more comfortable with taking risks, which proved beneficial in her entrepreneurial journey. This essay is based on a conversation with Kerpen, the co-founder and CEO of Whisper Group. The text has been edited for length and clarity.

Carrie's parents wanted her to have a secure, steady career, but she preferred a life filled with joy. Her father had a brief career as a private law practitioner before becoming a law clerk and later a judge, seeking the security and pension that came with a government job. Her mother, a social worker, also held a steady job. They taught their children to be cautious with their finances.

During the 1980s stock market crash, Kerpen asked her parents if they were alright and recalled her dad reassuring her that they were safe since they didn't invest in the market.

Kerpen's family led a simple, low-risk life, which she found comfortable. At first, she was content with their way of living. However, when she got married at 24, she realized her marriage wasn't working. She lacked the courage to leave until her daughter was born, making the risk of being a single mom less daunting than staying in an unhappy marriage. Similarly, at work, she wasn't initially comfortable with sales, but she took the leap into sales only when staying in a lesser-paying job became too stressful.

Kerpen's biggest risk was her second wedding, which later became the launch of her business. When her husband David proposed, he envisioned a grand wedding, despite Kerpen's reservations about the idea. Despite her initial reluctance, she took a significant risk by reaching out to a minor-league baseball team to rent out their stadium and selling about $125,000 in sponsorships for the wedding.

Back in 2006, the concept of a sponsored wedding was novel and might have seemed gauche. Fortunately, their sponsors, friends, and strangers loved the idea. This led to the establishment of Likeable, a media company, which Kerpen scaled over time and eventually sold for eight figures in 2020.