Emma May — entrepreneur, lawyer, and former insider in the Alberta Premier's office — joins Chris to talk about building Sophie Grace under relentless pressure, trusting your creative gut, and a candid take on Alberta's referendum from someone who's been in the room. I've known Emma May a long time — long enough to have watched her move from law, to real estate, to the inner workings of the Alberta Premier's office, and now to building one of the more quietly remarkable companies I know. Sophie Grace makes modular, mix-and-match workwear for professional women, and its customers are the kind of people who lead governments, run trials, and preside over universities — women who, as Emma puts it, are "the executive producer, not the movie star." I wanted Emma at the tavern because she's an entrepreneur in the thick of the scale-up grind, the same as me, and she's fought off a run of challenges most founders never face all at once: a 145% tariff that made her U.S. business impossible overnight, the death of her manufacturer with product half-made on the table, an inventory crunch that landed straight into a port strike. She talks openly about how she got through it — including the "rule of first sale" comeback that rebuilt the U.S. into 60% of her business — and about the personal ground underneath it all: a separation, losing her mother, and finally finding the stability to trust her own vision. We got into the things that make her business unusual — why authenticity beats AI-generated marketing, what Lululemon and Chip Wilson reveal about the war between product innovation and corporate drift, and why she personally messages her best customers just to understand them. And because Emma and I share a political past, I couldn't not ask: as someone who once helped run the Premier's Southern Alberta office, what does she really make of the separation referendum? Her answer is as candid as anything I've put on this show. This one runs from founder resilience to national identity and back again. If you're building something, or just trying to make sense of where this province and this country are headed, it's worth your time. Chapters 00:00Introduction to Emma May: A Multifaceted Entrepreneur 01:28Navigating Daily Challenges as an Entrepreneur 03:41Personal Growth and Business Vision 06:02Facing Tariffs and Market Challenges 09:08The Birth of Sophie Grace: Modular Workwear for Women 12:20Marketing Strategies for a Unique Customer Base 19:27Motivation Behind the Business: Pride and Customer Satisfaction 31:15Insights into the Fashion Industry: Challenges and Realities 34:57Embracing Creativity in Fashion 38:45The Importance of Brand Identity 41:59Navigating Corporate Culture and Innovation 44:21Quality vs. Fast Fashion 47:35Political Landscape and Leadership 01:03:26Preparing the Next Generation for Uncertainty
