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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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What if the hardest season of your life became the spark for your life’s work? We sit down with first-time mom and first-time founder Jill Olish, who launched Mama Outspoken during the pandemic while confronting postpartum anxiety, depression, and rage. Instead of waiting for a better moment, she built a platform that helps mothers find their voice, ask for help, and navigate the messy, unspoken transitions of motherhood.
Jill takes us inside the decisions that shaped her path: leaving a rigid job for virtual assistant work, turning lived experience into a podcast and a book, and building a supportive village focused on maternal mental health. We talk about the reality behind the nursery photos—emergency cesarean recovery, intrusive thoughts, sleepless nights, and the isolation of early parenthood—alongside the practices that made entrepreneurship possible with a newborn. Her simple, powerful system “sticky note time” shows how to dump the mental load, prioritize what matters, and create momentum without burning out.
Across the conversation we unpack sustainable growth, boundaries that match school calendars, and why rest is a strategy for resilience. Jill’s mantra you are the mom you were intended to be reframes perfectionism and offers a lifeline to anyone feeling behind. If you’re on the fence about starting a business, craving real talk about postpartum mental health, or looking for practical ways to juggle work and family, this story will meet you where you are and help you take your next small step.
If this conversation helped you, follow the show, share it with a friend who needs it, and leave a review to help more listeners find these stories.
Chapters
1. Season Five Kickoff & Mission (00:00:00)
2. Sponsors And Wellness Focus (00:01:33)
3. Entrepreneurial Journey Series Setup (00:02:02)
4. Introducing Guest Jill Olish (00:02:45)
5. Pandemic Motherhood Sparks A Pivot (00:05:13)
6. Expectations Versus Reality Of Postpartum (00:08:49)
7. From VA Work To Mama Outspoken (00:12:13)
8. Sharing Stories As Healing (00:15:45)
9. Considering A Second Birth Differently (00:18:07)
10. Redefining Entrepreneurship As A Mom (00:20:39)
11. Blending Work And Motherhood Boundaries (00:23:15)
12. Guilt, Resentment, And Real Self‑Care (00:26:52)
13. Finding A Voice And Asking For Help (00:30:00)
14. Naming The Hard Truths (00:33:20)
15. Grace And Sustainable Growth (00:36:08)
16. Sticky Note Time For Momentum (00:39:03)
17. Legacy, Mentorship, And Identity (00:42:00)
225 episodes
