9 to 5ish with theSkimm

Joi Gordon is the CEO of Dress for Success. That’s the nonprofit that provides low-income women clothing and career counseling to help them succeed in their careers. But she didn’t start there. Joi got her start as a lawyer and volunteered at Dress for Success on the side. Not long after that, she switched over full time. And she’s spent the last 20 years growing the nonprofit from one storefront in NYC … to a global entity. On the Couch, she talks to us about why she gave up her law career (6:00), what she looks for when hiring full-time employees (10:50), and the key to convincing people to get on your side (14:25). PS: This week, we’re getting our focus on with Oprah’s new book, “The Path Made Clear.” Get it here.  Learn more about your ad choices. Visit megaphone.fm/adchoices

Shilpa Shah and Karla Gallardo are the co-founders of Cuyana, the fashion brand that’s all about “fewer, better things.” Aka high-quality clothes and bags at a price that doesn’t hurt your wallet. Shilpa spent the first part of her career building web and mobile apps for Fortune 500 companies. Karla grew up in Ecuador and had a quick career in finance before she and Shilpa met at business school. And decided to start Cuyana together. It paid off. Earlier this year, they closed their Series C round of funding. On the Couch, they talk to us about how to find a cofounder (7:00) and why fundraising is so hard (19:33). Plus we put them to a cofounder compatibility test that a VC gave us way back when (30:52).PS: The spring refresh has officially hit our bookshelves. We’re adding “The Hill to Die On” by Jake Sherman and Anna Palmer to our list. Get it here. The Hill to Die on/ Get it Here https://skimmth.is/2IzPxtI Learn more about your ad choices. Visit megaphone.fm/adchoices

It’s Stress Awareness Month. Chelsea Handler has been working on managing hers. You know Chelsea as the comedian … turned late-night host … turned Netflix documentarian … turned activist and advocate. And she just became a 5-time best-selling author with her new book “Life Will Be the Death of Me … And You, Too!” – which came out the day we recorded this episode. Chelsea is a long-time friend of theSkimm and one of our earliest investors. On the Couch, she talks to us about what led to her latest shift, going with her gut, and navigating criticism. Which she’s very familiar with.  Learn more about your ad choices. Visit megaphone.fm/adchoices

Tracy Sun is an expert at making big changes in her career. She started off as a neuroscience researcher. Casual. But then she decided to follow her passion for fashion and business. Throughout her career, she’s helped start – and grow – several companies. Today, she’s the founder and Senior VP of New Markets at Poshmark, the platform that helps 40 million people buy and sell their clothes and accessories online. One of us is a superfan. On the couch, Tracy talks to us about finding a cofounder, managing a team through the failure of her first business, and not being afraid of the things she doesn’t know.PS: What we’re reading this week: NBC correspondent Jean Chatzky’s new book, “Women with Money: The Judgment-Free Guide to Creating the Joyful, Less Stressed, Purposeful (and, Yes, Rich) Life You Deserve.” Get it here. Learn more about your ad choices. Visit megaphone.fm/adchoices

Sarah Goldberg has been passionate about acting since she was a little kid. She got her first big break at the Young Vic Theatre in London, but eventually made the switch from the stage to the screen. Now you know her as Sally on HBO’s “Barry,” the show about an ex-marine-turned-hitman who decides to make a career transition. To acting. On the show, Sarah stars alongside some of the greats: Bill Hader and Henry Winkler. On this episode of “Skimm’d from the Couch” – live from HBO’s Inspiration Room – she talks to us about being 45 minutes late to her audition for “Barry”, what it’s like to work with Stefon and the Fonz every day, and dealing with imposter syndrome Learn more about your ad choices. Visit megaphone.fm/adchoices

Sarah Kate Ellis started her career in the magazine industry, where she helped launch and revitalize major media brands at outlets like InStyle, Vogue, and New York Magazine. Now, she’s the President and CEO of GLAAD. Translation: she’s an expert at using storytelling to shape coverage of the LGBTQ community in media and entertainment. On this episode, recorded live in HBO’s Inspiration Room in NYC, Sarah Kate talks to us about the challenges of leading an activist organization, the GLAAD Media Awards, and writing a book about the time she and her wife were pregnant at the same time.  Learn more about your ad choices. Visit megaphone.fm/adchoices

Arlan Hamilton started her career in the music industry, working with artists like Jason Derulo, Toni Braxton, and CeeLo Green. But in 2015, she took a look at Silicon Valley and saw a major lack of diversity there. So she decided to change it. Casual. Arlan started her venture firm Backstage Capital to invest in startups led by underrepresented founders. It wasn’t always easy (think: sleeping at the San Francisco airport while she built her business). But it paid off. Backstage Capital has invested nearly 5 million dollars into startups led by women, minorities, and members of the LGBTQ community. On this LIVE episode, Arlan talks to us about speaking up, taking risks, and getting inside the door… as an outsider.PS: After we recorded our interview with Arlan, Axios reported that Backstage Capital has run into trouble raising money for their most recent fund, and that the firm is shifting focus to its accelerator program. Arlan told us in an email Tuesday that Backstage is still working on the fund, and “will continue to until it's raised.”  Learn more about your ad choices. Visit megaphone.fm/adchoices

Katia Beauchamp started her career in finance. But after a few years, she decided that she didn’t feel challenged. So Katia switched gears … and went to Harvard Business School. Casual. That’s where she met her cofounder, Hayley Barna. And together, they launched Birchbox, the subscription company that helps people discover new beauty products. Since Katia and Hayley launched it in 2010, the company has grown and changed a lot: they’ve earned two and a half million active subscribers. They were acquired by one of their investors. And Hayley decided to leave in 2015. Katia has stayed on board as CEO. On the couch, she talks to us about learning to lead on her own, working through a complicated pregnancy, and the time she cold-emailed Apple co-founder Steve Jobs. And got a response.  Learn more about your ad choices. Visit megaphone.fm/adchoices

Rebecca Jarvis grew up with two passions: journalism and econ. As a teenager, she was even a reporter for a local kids’ program in Minnesota. But after college, Rebecca decided to go into finance. Years later, she got back to journalism. Today, she’s the Chief Business, Tech, and Economics Correspondent at ABC News. On the couch, she talks to us about the time she was on “The Apprentice”, how she made the switch from finance to journalism, and what she looks for in candidates now.PS: Rebecca has her own podcast, No Limits with Rebecca Jarvis, where she interviews female entrepreneurs about what it takes to build their business empires. After this episode, check it out -- because Rebecca’s interviewing US this week.  Learn more about your ad choices. Visit megaphone.fm/adchoices

If you like hearing from us once a week, how about audio from theSkimm every day? Our daily news podcast, ‘Skimm This,’ launches on Monday. Every weekday, we’re breaking down the most important stories of the day and explaining why they matter. Search ‘Skimm This’ and subscribe. You won’t want to miss it. Learn more about your ad choices. Visit megaphone.fm/adchoices