Episode 39: Letting go to find success

Women need to believe in themselves and trust themselves. We have internalized so much misogyny. We have internalized so much doubt that’s projected on us that becomes self-doubt.” – Judith Winfrey

Eight-figure serial entrepreneur and founder of peachdish.com, Judith Winfrey, shares the valuable lessons she’s learned from starting five businesses in under 15 years.

Most of us don’t think beyond our own personal health and nutrition when it comes to the type of food we buy and where we buy it. But Judith sees the broader effects that choosing to support local farms can have on the economy and the environment. It’s no wonder she’s been able to achieve such longevity and success in business - a rare feat in the food industry.

Helen and Judith talk about the unseen sacrifices that entrepreneurs make and how finding success as a Self-Made CEO™ sometimes means letting go of expectations.

What we tackle in this episode:

  • How surrounding yourself with the right people impacts your business

  • How the entrepreneurial journey rarely ends up looking like we imagine it

  • Why delegating can be one of the hardest (but most important) lessons to learn as a business owner

  • Why the best leaders are those who put their own ego aside

  • The stresses that come along with being CEO that most employees (and outsiders) never see

Resources mentioned in this episode:

GUEST: Judith Winfrey

To learn more about Judith’s background and what she’s currently working on, check out her recent feature in Pretty Southern.

Follow Judith on social media or visit her websites:


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HOSTED BY: Helen Ngo



Music by Muciscal_Chef

Track title: “Motivational Happy”