BRANDED Leaders

In this inspiring episode, Layla Kasha, Chief Marketing Officer at Grocery Outlet, joins Ben Kaplan to discuss how immigrant grit, entrepreneurial roots, and fearless marketing have shaped her unique leadership style.

Layla dives into Grocery Outlet’s “extreme value” model, selling branded products at deep discounts, and explains the brand’s bold pivot from traditional paper ads to fully digital campaigns.

She shares her powerful personal story, from growing up in a Middle Eastern immigrant family and working in her father’s Michigan party store as a child, to running her own restaurant and eventually becoming a CMO. Layla breaks down her approach to ruthless (yet win-win) negotiation, how failure became her greatest teacher, and why betting on yourself matters, especially when the stakes are high.

You’ll hear candid lessons about leadership, gender dynamics in the corporate world, and why she keeps Chris Voss’s Never Split the Difference in her car door. Plus, the surprising pet project she and her husband run on the side.
Whether you're an aspiring marketer, a fan of founder stories, or just someone trying to stretch a dollar at the grocery store, this episode delivers plenty of value.

Larry Kim built a $150 million company. Then he walked away.

In this episode, Larry opens up about the pressure of scaling a company from nothing, the emotional toll of success, and why he chose to start again—this time betting on AI.

As the founder of WordStream, Larry helped businesses spend over $1 billion on digital ads. But behind the numbers was a founder grappling with burnout, imposter syndrome, and a growing belief that the ad industry was broken.

Now, as CEO of Customers.AI, he’s building something radically different—a platform that finds customers without wasting money on ads. He reveals the mistakes that nearly broke him, the moments that defined him, and what it really takes to walk away from something you built.

This is a conversation about obsession, reinvention, and the uncomfortable truth behind growth at all costs.

In this episode of BRANDED, host Ben Kaplan sits down with Toby Burns, the founder and CEO of The Silent Disco Company. What began as a premium headphone rental service for exclusive weddings has evolved into a global silent party phenomenon, shipping thousands of kits to events across the world every week. Toby shares how he built his brand from the ground up, navigated the chaos of the pandemic, and defended his business against rising competition and cheap knockoffs.
Discover how Toby's relentless focus on innovation, customer service, and market positioning turned The Silent Disco Company into a leader in a rapidly growing industry. Whether you’re curious about scaling a niche business or redefining an entire market, this episode is packed with insights on building a brand that speaks volumes, without making a sound.

In this episode of Branded, Ben Kaplan sits down with Tammy Nam, CEO of Creatopy, to explore how AI is radically transforming the world of digital advertising.

From slashing campaign creation time from months to minutes to unlocking new efficiencies for enterprise brands, Tammy shares insights from the frontlines of AI innovation.

They dive into how enterprises are adapting faster than expected, why workflow integration is the next big unlock, and what skills marketers will need to thrive in an AI-driven future.

When the pandemic hit, Dig, a brand known for its vegetable-focused, farm-to-table menu, faced a harsh reality: their entire business model was built around in-person dining.

In this episode of Branded, Ben Kaplan sits down with Jessica Serrano, CMO of Dig, to uncover how the company transformed its strategy to not just survive, but thrive in a post-COVID world.

Jessica shares the bold moves that redefined their menu, expanded their reach, and turned digital ordering into half their business.

From pivoting their messaging to rethinking their approach to food, Dig’s journey is a masterclass in resilience and adaptation.

In this episode of Branded, Ben Kaplan sits down with Caitlin Choate, Chief Marketing Officer of Boatsetter — the platform transforming how we think about boating. Often called the “Airbnb of boats,” Boatsetter is making the luxury and lifestyle of the open water accessible to everyday people, not just yacht owners. Caitlin reveals how Boatsetter is doing more than just renting boats — they’re selling experiences, building trust in local markets, and redefining what it means to belong on the water. You’ll hear how Boatsetter overcame industry skepticism, why marketing seasonal products is a hidden advantage, and how emotion and storytelling fuel their growth.

Jen Grant, CMO of Dialpad, joins Ben Kaplan to talk about the reality behind AI in business, what actually helps customers and what’s just tech for tech’s sake.

She shares how Dialpad is shifting focus from shouting about AI to showing how it improves everyday conversations. They dive into the challenge of keeping messaging clear in a fast-moving market, what it really means to be customer-first, and why personality and real human connection still matter more than ever.
If you’re navigating brand, marketing, or just trying to stand out without the buzzword bingo, this one's for you.

Joe Miller didn’t plan to work in AI translation — but he’s now at the helm of Pocketalk, one of the most trusted names in secure real-time language translation across healthcare, education, and government. In this episode of BRANDED, Joe joins host Jackson Carpenter to break down what separates a novelty product from a real business, and why Pocketalk exploded when it leaned into “language friction” as a market problem.
Joe also shares stories from his wild ride through DirecTV, TiVo, clean tech, and mesh networking startup eero (which sold to Amazon), revealing a career built on chasing disruptive ideas, betting big early, and always knowing who your product is for — and who it’s not.
If you’ve ever wondered what makes a product stick, how to build a brand with purpose, or what great leadership looks like during chaos, this episode is packed.

In this episode of BRANDED, host Jackson Carpenter sits down with Meredith Binder, CMO of Novata, to explore her unexpected rise from technical communicator to marketing executive. Meredith shares how Novata is tackling ESG data challenges in private markets with a user-first approach inspired by TurboTax.
She opens up about the power of “happy accidents” in career growth, what it takes to lead with empathy and curiosity, and why marketing clarity is still a superpower. From leading teams across mergers to helping redefine how we talk about sustainability, Meredith brings a refreshing perspective on what real leadership looks like.

What happens when a single trampoline park expands into a powerhouse of seven youth-focused franchises? Jessica Correa, Chief Marketing Officer at Unleashed Brands, joins Jackson Carpenter to break down the art—and science—of scaling a brand ecosystem without losing the heart of each individual identity.

From legacy systems and AI-powered automation to marketing across wildly different age groups, Jessica shares the strategies driving growth across brands like Urban Air, Snapology, and Premier Martial Arts. It's a deep dive into building structure without suffocating creativity—and how to keep your brand agile in a world that’s constantly evolving.

Whether you're building a multi-brand empire or just trying to market to both 3-year-olds and teens (spoiler: not easy), this episode has something for you.