What does it look like to build a legacy brand when everyone around you is raising big and scaling fast?

Melissa Mash spent years at Coach, helping launch its wholesale e-commerce channel and leading the turnaround of its first UK/EU location at Heathrow Terminal 5. There, she heard the same request over and over: travelers wanted a beautiful bag that could actually organize their laptops, tech, and currencies, without costing $500+. Nobody had it. So she went to Wharton, found her two co-founders, focus-grouped and surveyed 1,000 people, and launched Dagne Dover in 2013 with $40,000 in presales before raising a dollar. Thirteen years later, Dagne Dover is known for its neoprene bags in iconic colors, has a 40%+ repeat customer rate, and gets about half its site traffic from completely unpaid, organic search.

In this conversation, we talk about why Melissa refused to play the "hot potato" game of raising at inflated valuations, how she thinks about choosing co-founders (and why three can be better than two), why being product-first beats outspending on marketing, how the brand handles dupes of its designs and colors, and what gives a brand permission to expand into something new.

This episode is about building with patience and intention, and knowing exactly why you're building in the first place.

What does it take to turn around one of America's most iconic (and, for a while, most irrelevant) brands? Chip Bergh spent 28 years at Procter & Gamble, where he created Swiffer and ran Gillette and Old Spice, before taking over as CEO of Levi Strauss & Co. in 2011. At the time, Levi's was $2 billion in debt, hadn't grown in over a decade, and had all but disappeared from culture. By the time he stepped down 12+ years later, revenue had grown 40% and Levi's was back at the center of the cultural conversation.

In this episode, we talk about the listening tour Chip ran in his first months as CEO (and the six questions he asked 60 executives that cut through the noise fast), the bet on Levi's Stadium before the ground was even broken, the in-home interview in Bangalore that produced the "Live in Levi's" campaign, and the decade-long shift from a wholesale business to one built on direct consumer relationships. We also get into Chip's advice for leading a long, fulfilling career: why he was up at 5am working out no matter where in the world he was, why he thinks of a career as both a marathon and a series of sprints, and why he came to define himself as an athlete before he defined himself as a CEO. His bigger point: don't let a company's culture dictate how you live your life, because the choices you make are the ones you have to live with. 

Chip was also my marketing professor at HBS and the person who encouraged me to start this podcast in the first place, so this one is a full-circle moment for me.

This episode is about what it actually takes to rebuild a brand's relevance from the inside out and the discipline, curiosity, and self-knowledge required to do it, both in business and in life.

What does it take to build a brand nobody knew they needed? Lily Geiger started Figlia in the middle of the pandemic, betting that non-alcoholic drinkers deserved something more sophisticated than soda water (and did it without a single connection in food and beverage). Five years later, Figlia is in Whole Foods, on menus at Michelin-starred restaurants, and growing 194% year over year through distribution alone.

In this episode, Lily shares how she taught herself formulation from scratch, insisting on a preservative-free bottle even when it made manufacturing harder, and how she knew Figlia needed to be its own category, not an analog to alcohol. She also gets into the deliberate strategy behind going deep in New York before ever considering national expansion, why she built a team out of her closest friends and family and made it work, and how she bootstrapped the business for a full year before raising a dollar of outside capital.

If you're building (or dreaming of building) a consumer brand, this episode is full of lessons on conviction, discipline, and betting on yourself before anyone else will.

Ariana Ferwerda co-founded Halfdays in 2020 alongside Olympic freestyle skier Kylie McKinnon, after both kept running into the same problem: women's ski wear was ugly, ill-fitting, way too expensive, or all three. What started as a scrappy DTC ski brand launched mid-pandemic has grown into a $25 million community-first outdoor apparel company, with a flagship store in Denver, 150 wholesale doors, and a recently closed $10 million Series A.

In this conversation, we talk about the origin story behind Halfdays, how a 10,000-person waitlist for ski pants became the proof point that changed everything, why Ariana believes founders can over-index on "building community," and how the brand is expanding beyond ski into year-round apparel without losing what made people trust it in the first place.

This episode is about trusting your own instincts as a founder, even when you might think the experts around you know more than you do.

Michelle Cordeiro Grant is a serial entrepreneur and brand builder who has spent her career identifying white space in consumer markets and building true communities around them. After years in retail at Victoria's Secret, VF Corporation, and Nautica, she founded LIVELY in 2016, coining the term "Leisurée" and redefining the lingerie category by leading with community before product. In three years, she grew LIVELY to over 165,000 brand ambassadors and a $105 million acquisition. She then turned her attention to the wellness space, founding GORGIE in 2022, a better-for-you energy drink that is now the #1 fastest-growing energy brand in the U.S. natural channel. In the past year, GORGIE has seen massive growth; they are now in thousands of retail doors nationwide across over 25 retail chains, have a strategic partnership with Alix Earle, and closed a $24.5 million Series A.

Michelle is known for doing things backwards, building the audience before the product, and the community before the brand. In this conversation, we talk about how she built LIVELY's community before she had a single product to sell, what it felt like to sell her first company, how she found GORGIE after a winding road of failed ideas, and what it really means to build with your customers rather than just for them.

This episode is about what happens when you stop guessing what people want and just ask them.

What does it really take to build a brand that lasts? Scott Tannen co-founded Boll & Branch with his wife Missy 12 years ago after a frustrating hunt for sheets that were both high-quality and ethically made. They've since built it into a category-defining luxury bedding brand known for comfort, trust, and supply chain transparency.

In this episode, Scott shares the early days of wiring his life savings to a factory in India and hoping for the best, why Missy insisted on designing their fabric from scratch when no one else would, and the moment they almost blew it by launching too many products too fast after their first big sales spike. We also dig into why every new product is a risk to brand equity, how sustainability became a "reason to believe" rather than the main pitch, why retail stores act as a marketing channel as much as a sales one, and how AI is shifting the consumer journey from "best sheets" to "best sheets for me."

If you're building (or dreaming of building) a product-first consumer brand, this one's full of hard-won lessons on patience, focus, and staying true to what made people trust you in the first place.