Actress-turned-entrepreneur Cameron Diaz and consumer brand builder Katherine Power (WhoWhatWear, Merit Beauty, Versed) had been friends for years before they decided to launch Avaline, their transparently produced organic wine brand. After realizing the wines they loved were full of additives and hidden ingredients, they saw an opportunity to create a new kind of bottle – and transform the wine industry in the process. We spoke with them about how they've transformed their careers, and their lives, by launching this brand.

In this episode, they share: 

Why Cameron left acting behind – and what that’s unlocked for her

Katherine’s tips for time management and efficiency 

What we can’t Google about Cameron 

How they broke into the alcohol industry 

The surprising things you should look for when choosing wine

Cameron Diaz and Katherine Power on Evolving Their Careers and Finding Peace

The work advice you need, from women who’ve been there. Every week, join the co-founders and co-CEOs of theSkimm, Carly Zakin and Danielle Weisberg, as they help you get what you want out of your career by talking to the smartest leaders they know.

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At 59, Edith Cooper never thought she’d make a career pivot. She spent nearly 30 years working her way up at Goldman Sachs, but then, she was approached to co-found a company called Medley. Who was the other co-founder? Jordan Taylor, AKA her daughter. The mom and daughter duo launched Medley, a coaching platform equipping Millennial-aged workers with the skills they need to be dynamic, inclusive, and authentic leaders. 

In this episode, Jordan and Edith share: 


Whether Jordan calls Edith “mom” or “Edith” in the workplace

The parts of her Wall Street HR career that Edith misses 

Why we forget to support middle-level managers – and how Medley solves for it

The moments Jordan relies on Edith as “mom” vs. “co-founder” 

Why boundary setting is crucial to success as co-founders who are friends or family


Psst…this episode of “9 to 5ish” is brought to you by New York Life. Their financial professionals can help you navigate life’s decisions, big and small.

Jordan Taylor and Edith Cooper on Running a Business as Mother and Daughter

Kentucky-born model Molly Sims never met a biscuit she didn’t like. Her southern charm brought her to college at Vanderbilt University, where she made the boldest move of her career: quitting her pre-law studies to become a full time model. Molly was in her early 20s, alone, and homesick halfway across the world. But with placements on the cover of Sports Illustrated, French Vogue and more, it’s safe to say she made a name for herself.  

In this episode of 9 to 5ish, Molly shares: 


Why southern sorority culture wasn’t for her 

How her mother encouraged her to think beyond the US for her career + life experience

Why she’d never want her daughter to become a model 

The secret to building resilience and the “thick skin” that helped her survive the modeling industry

How confronting her mental health challenges helped her be OK with work curveballs


Check out Molly's beauty brand, YSE Beauty.

YSE Beauty Founder Molly Sims on Leaving a Job with Dignity

Alli Webb was a stay-at-home mom for five years when she realized she needed to get out of the house more. So she started a mobile hair business. She’d go house-to-house and offer $40 blowouts to moms in LA, something that pretty much no one was doing at the time. She soon opened her first brick and mortar and called it Drybar. 100+ locations later, Alli sold the company for more than $200 million. All without a college degree or formal business training. 
In this episode of 9 to 5ish, Alli shares: 


The sunshine and beach-haired days of her childhood growing up in Boca Raton 

How having parents who operated a small biz gave her life lessons in entrepreneurship

Why it felt intoxicating building and scaling Drybar, plus the mental cost that came with it

How her divorce, son’s visit to rehab, and burnout led to her book, “The Messy Truth” 

Why she felt intimidated when fundraising + curating the Drybar board – and how she got through it

Drybar Founder Alli Webb on Scaling a $200+ Million Dollar Business without a College Degree

Before September 2018, the public didn’t know Dr. Christine Blasey Ford. She was a busy mom and professor at Palo Alto University and Stanford. Then, she leveled a sexual assault accusation against Judge Brett Kavanaugh, a SCOTUS nominee. She testified in front of the Senate Judiciary Committee and 5 million people tuned in. From then on, any concept of a private life went out the window. Christine needed security to go…well, anywhere. Strangers sent her and her family death threats. Five years later, Christine shares how she navigates her new normal, plus the story behind the headlines and soundbites. 
In this episode, Christine shares: 

The behind-the-scenes leading up to her testimony against Judge Kavanaugh

What she makes of her unique connection to Anita Hill

Suggestions on what to say to sexual assault survivors instead of “I believe you”

What parts of working on her memoir, “One Way Back”, were therapeutic – and which were re-traumatizing 


Content warning: this topic deals with sexual assault. Please take care when listening.

Christine Blasey Ford on Detaching Yourself from the Outcome

Zibby Owens witnessed first-hand the payoff of great entrepreneurship as she watched her father build his company, Blackstone, from the ground up. She freelanced as a writer earlier in her career. She focused on raising her kids for 10+ years. Then her marriage ended. So she spent her weekends without the kids rekindling her love of literature – and developing a media empire focusing on all things books. 

In this episode, Zibby shares: 

The story behind her iconic color-coordinated bookshelf

What she learned watching her father build his private equity business, Blackstone

Her recent Vogue article she published – and why she almost wishes she hadn’t

How her podcast became the vehicle to sell her first book

Why building your personal brand is key in almost any industry today

Cameron Diaz and Katherine Power on Evolving Their Careers and Finding Peace

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