Hitting The Mark

Advertising veteran Jeff Grace and his wife, Stacy, founded the underwear brand KENT, which uses no synthetics, pesticides, or plastic. Every piece of KENT clothing (even the packaging) is fully biodegradable and compostable, reducing landfill waste and helping to reverse climate change.This episode felt more like a casual yet fascinating chat between two brand marketing guys who also started their own D2C businesses. So if you seek advice on running (or not running) ads, influencers, optimization, brand authenticity, and brand stories, this episode is for you. And we made sure to drop lots of brand gossip in between. 

SendCutSend is a B2B manufacturing company, yet it's become a beloved brand among those familiar with it. The 700-employee company makes custom parts for DIYers in the garage and for innovation giants like Disney, Waymo, and Blue Origin. Jim pivoted from running a software and marketing shop to becoming a Sequoia-funded manufacturing giant. We discuss how both constraints and conviction drive his business and what it took to craft a brand.

Brandon McCraney is the Founder and Master Blender at Olde Raleigh Distillery, a family-owned and operated craft distillery focused on small-batch and limited-release bourbon and whiskies. Two years into this journey, Olde Raleigh was honored with the prestigious title of Best Micro Distillery in the US. This brand story is as much about persistence as it is about art, and Brandon was so focused on brand storytelling that there was a line around the block on opening day.

Allison Taylor grew up on her family’s plum farm in Northern California, which has been around since 1916 and is one of the world's largest producers of dried plums. In 2018, Allison and her sisters launched Le Prunier, a plum-based skincare brand that reunited them with the farm and created a new family business that is rooted in authenticity and sustainability.

Dan Lilienthal and José Chayet co-founded [untitled], a sacred place for work-in-progress music used by hundreds of thousands of artists and producers, including Justin Bieber, Hayley Williams, and Geese. The brand was recently awarded one of Fast Company’s 10 most innovative music companies of 2026.