Bobbi Brown is one of the most legendary names in beauty. Not only is she the makeup artist responsible for introducing no-makeup makeup, but she's also an author 10 times over and the founder of both Bobbi Brown Cosmetics and Jones Road. On this episode, she reflects on her career through the lens of money, power, and style while discussing her recent memoir, Still Bobbi. She shares how she dealt with the difficult emotions she felt after being fired from her own company, the wise financial advice she got from her father, and how she found her personal makeup aesthetic.

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In this live-recorded episode, we’re talking about money, power, and style with actor, producer, and founder of Personal Day Lili Reinhart. She first rose to fame in 2017 as Betty Cooper in The CW’s Riverdale and since then has gone on to star in countless other projects, including the recent Mubi release Hal & Harper. In addition to her work as an actor, she’s also a producer (a role she says makes her feel powerful) and has founded her own production company, Small Victory Productions. Outside of the entertainment industry, Reinhart launched the award-winning skincare line Personal Day last year, which was inspired by her personal struggles with acne. In this episode, she discusses being a romantic, why she sometimes feels “unstylish,” and the important money conversations she had with her fellow Riverdale castmates.

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This episode, we're focusing on power with the founder and CEO of Deep Blue Sports + Entertainment Laura Correnti. In 2019, she witnessed the crowd chanting "equal pay" when the U.S. Women's National team won the World Cup, and at that moment, she knew she had to leverage her background as an advertising-industry powerhouse to expand the commercial investment in women's sports. Today, Correnti discusses the correlation between being an athlete and being a C-suite executive, why she teamed up with Sue Bird to create her company, and what the future of women’s sports looks like.

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This episode, we’re focusing on the topic of power with Crooked Media VP of Political Strategy Shaniqua McClendon. With the special “odd year” elections coming up on November 4, she’s here to break down what’s at stake this Election Day. She’s also offering advice on how to stay engaged in politics when cynicism creeps in, what to expect in next year’s midterms, and how to build a robust media diet without being constantly overwhelmed. As the creator of Vote Save America and a longtime political organizer, McClendon has so much important information to share, so be sure to tune in.

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On this episode, we’re focusing on the topic of money with financial translator and author of the Broke Millennial book series Erin Lowry. In 2013, Lowry began sharing money advice on her blog, Broke Millennial, and quickly became a trusted source for personal finance advice. Today, she’s sharing how to approach money conversations in romantic relationships, why you might need a financial therapist, and the helpful scripts you can use when declining invitations to dinners that you just can’t afford. Plus, in case you missed it, Nikki got engaged recently! So Lowry shares all her wedding and future planning advice with her. Tune in to hear Lowry’s expert financial POV on everything from prenups to trad wives.

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Today, we’re focusing on the topic of style with content creator and disability advocate April Lockhart. She began her career in fashion and beauty, working for companies including Victoria’s Secret, Tarte, and Caudalie. While working a 9-to-5, she also created content on the side, and in 2022, she gained traction for her series Normalizing Disabled Fashion Girlies. When she realized she was earning five times her salary from her side hustle and maxing out her PTO, she decided to leave her role as director of influencer and partnerships at Ilia Beauty to pursue content creation full-time. In addition to her work as a creator, Lockhart is also a disability advocate. This year, she founded Disabled&, a community for creatives with disabilities. In this episode, she gets into what it’s like to go to fashion week as an influencer, the state of disability representation in fashion, and why inclusive design is so important.

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In this live-recorded episode, we’re talking about money, power, and style with Michaela Jaé Rodriguez. She’s well-known for her roles in projects like Pose, Loot, and Tick, Tick… Boom! and made history in 2022 as the first transgender actress to win a Golden Globe. Though Rodriguez is widely lauded for her acting performances, her first love was music, and in 2024, she released her debut album, 33. Today, we chat about why she’ll always spend money on herself, the shoes that are worth the pain, and the impact she hopes her career will have on the next generation. Plus, Rodriguez shares the two music industry icons she looks to for fashion inspiration.

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On this live-recorded episode, we’re talking about the new rules of networking with career influencer and author of Interviewology Anna Papalia. Papalia spent her early career in recruiting, and now she uses her massive social media platform to help millions of people nail their interviews and climb the corporate ladder. Papalia's here today to break down all nitty-gritty of modern-day networking, including how to reframe the practice, why helping yourself will lead to others helping you, and which kind of interview style you fall into. Plus, Papalia shares tangible tips for how to practice for your next interview.

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Issa Rae truly does it all. Not only is she a multifaceted entertainment powerhouse, but she also runs businesses in various industries—from prosecco to food to haircare. Today on the show, the former Marie Claire cover star joins us to talk about money, power, and style, including how she crowdfunded her early projects like Awkward Black Girl, how she overcame "grateful to be here" energy after partnering with HBO, and what it means to be boldly elegant in her style. She also tells us about her newest projects: her book I Should Be Smarter by Now and her two-part docuseries Seen and Heard. Plus, Rae shares why creativity is not the most important trait to be successful in the entertainment industry.

The full video of this episode is also available on YouTube.

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Today on the show, we’re focusing on style with Brynn Wallner, the founder of Dimepiece. Wallner unexpectedly fell in love with the world of watches while working at Sotheby's and founded Dimepiece to encourage more women to take part. Since getting her first job writing about watches through host Nikki Ogunnaike, Wallner’s voice has been featured in publications like W Magazine, Nylon, and Harper’s Bazaar as a leader in the field. Wallner sits down with us to talk about sourcing watches for megastars like Simone Biles, spotting “It-girl watches,” and launching her own sold-out watch with Timex. Plus, she dishes on the best secondhand sites and brands to go to when you’re looking for a starter watch or another timeless timepiece to add to your collection.

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