Why Women Over 40 Are Starting Businesses — and Winning, with Lindsay Pinchuk
What if the business you keep daydreaming about isn’t a midlife crisis — it’s your midlife calling? In this episode, Wendy sits down with award-winning entrepreneur and small business mentor Lindsay Pinchuk, one of the less than 1% of female founders to lead her company through an acquisition. Lindsay built her first brand, Bump Club and Beyond, from a $500 investment into a seven-figure powerhouse — partnering with Target, Nordstrom, and Huggies and reaching three million people a month — before selling it and starting over.
Today she runs Dear FoundHer…, a top podcast and community helping women over forty build businesses that actually last. Lindsay and Wendy dig into why it’s never too late to bet on yourself, how to start before you feel ready, the simple two-question litmus test behind every brave pivot, and why your decades of life experience are your biggest entrepreneurial advantage. If a little voice keeps whispering “someday,” consider this your wake-up call.
What You’ll Learn
- The two-question litmus test Lindsay uses before every scary leap — “What’s the worst that can happen?” and “Can I live with that?”
- Why “just start” beats waiting for the perfect plan — and how messy beginnings become real businesses
- How listening to your community (instead of forcing your own ideas) builds something people actually want
- Why women 45–54 are the fastest-growing group of entrepreneurs — and the life experience that gives them an edge
- How to give yourself permission to pivot when something no longer feels aligned
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