Skimm'd From The Couch

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. 

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

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. 

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.

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

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. 

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 “wil

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. 

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. 

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.

You might’ve noticed that we’ve been talking about money lately at theSkimm. A big part of money 101: knowing how to negotiate. Peggy Johnson’s an expert. She’s the EVP of business development at Microsoft. Translation: she drives strategic partnerships for the company … and negotiates. A lot. Peggy’s been running the show since 2014. She’s an avid runner, and she’s been known to carry out negotiations with sneakers on. While running. Before Microsoft, she spent almost 25 years working her way up the ladder at Qualcomm. On the couch, she talks to us about maintaining business relationships, standing out as an introvert, and playing to her strengths at the negotiation table.

Anu Duggal and Sutian Dong are the partners of Female Founders Fund, where they invest in tech companies started by women. Anu began her career as an entrepreneur -- including starting India’s first wine bar, and an e-commerce company. Sutian came from the investing side of things. In 2014, Anu decided to launch Female Founders Fund. A couple years later, she brought Sutian on as a partner. Together, they’ve invested in companies like Thrive Global and Rent the Runway. On the Couch, they talk to us about what makes a great cold email, the companies in their shadow portfolios, and why they’re so focused on building communities for female founders.

Valentine’s Day is coming up. And Amber Venz Box knows a thing or two about making relationships work … at work. She’s the president of RewardStyle -- the company she founded with her then-boyfriend, now-husband Baxter. Amber started out as a personal shopper. But she realized that people were buying the products she recommended on her blog on their own … and cutting her out of a commission. So in 2011, Amber and Baxter started RewardStyle. It connects brands and influencers so both sides can benefit. In 2017, they drove over a billion dollars in sales. And launched their app, which attracted a million users in just 9 months. But building her company hasn’t been easy. On the Couch, she talks to us about being an introverted leader, how to network, and what it’s like to build a business with your SO. 

New York Fashion Week kicks off this week. So we sat down with Rebecca Minkoff -- the co-founder and creative director of, you guessed it, Rebecca Minkoff, LLC. That’s the fashion brand she started in 2005 with her brother. Since then, their company has been a leader in shaping the future of fashion: Rebecca Minkoff was one of the first fashion brands to engage with their customers through social media and influencers. But she hasn’t stopped there. In 2018, Rebecca launched the Female Founder Collective to support and invest in women-led businesses. At this LIVE power breakfast, she talks to us about taking risks, going to couples therapy with her brother-slash-cofounder, and supporting other women in the workplace.

Arielle Charnas is the super influencer behind the style blog-turned-brand Something Navy. Arielle started the blog in 2009, when she was just 22 years old. And since then, she’s gained a following of more than a million people. Last year, she launched her brand with Nordstrom… which was so popular that it crashed the site. Now, she’s rolling out more and more collections with the retailer. On the couch, she talks to us about being her own boss, choosing the right opportunities, and building a team.

New Year...new Skimm’d from the Couch. We’re starting off the year with the queen of motivation, Jillian Michaels. You might remember Jillian from her role as a trainer on the hit NBC show, “The Biggest Loser,” or from her fitness DVDs. But you might not know that she also built a wellness empire, including an exercise streaming platform, and her award-winning fitness app. Jillian’s also a best-selling author, with a brand-new book out: “The 6 Keys: Unlock Your Genetic Potential for Ageless Strength, Health, and Beauty.” On the couch, she talks to us about how she motivates herself, leading by example, and making long-term resolutions...that you can actually keep. Get ready to be inspired.

When Alexa von Tobel graduated college, she still had a lot of q’s about how to manage her cash. So she did what anyone would: wrote a 75-page business plan. And took it to Harvard Business School. Casual. But within a semester, she decided to drop out and start her business for real. Enter: LearnVest, the company that makes financial resources more accessible for everyone. In 2015, LearnVest was acquired by Northwestern Mutual. And now, Alexa has responsibilities at both companies. On the couch, she talks to us about dropping out of business school, why she has two executive coaches, and going through an acquisition...while 9 months pregnant.

Samantha Barry grew up in Ireland. And she always knew news was the path for her. Sam started out her career as a researcher, and then became an international reporter. Her reporting took her around the world, where she started to see the power of social media. She took that realization and went on to help major news organizations build out their social media presences. We’re talking huge names like BBC and CNN. Now, she’s the editor in chief of Glamour. Anna Wintour has called her Glamour’s first digital-native editor...so it’s no surprise that Sam’s taking the magazine entirely online. On the couch, she talks to us about being fearless, making changes at an established company, and the three ways she negotiates for herself.

Our guest this week is the one and only Martha Stewart. Growing up, she had a knack for all things lifestyle: cooking, gardening and sewing. But after college, she decided to follow a different path. To Wall Street. Martha eventually took the business skills she learned there...and used them to build an empire of her own. There have been bumps along the way. But now, she’s the Chief Creative Officer of Sequential Brands Group, where she oversees everything from the Martha Stewart Living Magazine to her cooking show with Snoop Dogg. We had a lot of questions, too. On the couch, she talks to us about her very first side hustle, how she got her company started, and what she’s like as a manager.

Beth Comstock is the first female vice chair of GE. But before that, she built a career in communications at companies like CBS, CNN, and NBCUniversal. At NBC, Beth helped launch one of your favorite binge-ing sites: Hulu. And she kept working her way up the ranks. All the way to becoming the first female Vice Chair of GE. Most recently -- Beth wrote a book about courage, creativity, and making change. It’s called “Imagine it Forward.” On the couch, she talks to us about what a vice chair actually is, why she took the job nobody else wanted, and what it means to be an introverted leader.