Stories Business Finance & Insurance · Chicago,

What This Mom Founder Learned After Hiring Her First Employee

Jenna Cole hovered over her first hire for two months. The second time, she handed over the keys and left for a week.

Interview by MMM Editorial
Sep 15, 2026 · Updated Sep 30, 2026

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“I hovered for two months. She quit. I deserved that.”
— Jenna Cole, Cole Bookkeeping

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The Founder

Jenna Cole

Founder · Chicago,

The Business

Cole Bookkeeping

Finance & Insurance

Jenna Cole hovered over her first hire for two months. The second time, she handed over the keys and left for a week.

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