Episode Summary
Executive Summary: Caitlin Smith explains how personal health changes led her to launch Simple Mills, a grain-free baking brand that scaled from kitchen experiments and local Whole Foods demos into a national natural-foods company. The episode highlights scrappy early execution, retail strategy, fundraising, and leadership lessons behind building a “better-for-you” pantry brand.
Main Topics: Personal health trigger and paleo discovery (Priority: 5/5): Smith’s fatigue and poor diet while consulting at Deloitte pushed her to test a paleo-style diet, which she says dramatically improved her energy and wellbeing and inspired her to rethink food as a business opportunity. From idea to product: grain-free baking mixes (Priority: 5/5): She explored multiple food concepts before settling on muffin mixes made with almond, coconut, and cassava-based ingredients, aiming for products that were both convenient and genuinely delicious. Bootstrapping, homemade production, and first retail entry (Priority: 5/5): Smith self-funded the business, produced mixes in a commercial kitchen on nights and weekends, and broke into Whole Foods by directly pitching a local store manager with samples. Amazon, influencer lift, and retail expansion (Priority: 4/5): Early online sales were slow until an influencer post created rapid demand; that momentum helped Simple Mills climb Amazon rankings and expand into additional chains and regions. Fundraising and scaling the team (Priority: 5/5): A threatened angel deal led Smith’s parents to mortgage their house for $200,000; later, a business-school competition helped her raise a larger round and hire a small team to scale operations. Leadership mistakes and learning to delegate (Priority: 4/5): As the company grew, Smith learned she was over-directing senior hires and needed a leadership coach to help her trust experts, improve communication, and stop micromanaging. Brand philosophy and category strategy (Priority: 4/5): Smith argues Simple Mills wins by avoiding shortcuts like natural flavors and by focusing on products consumers actually want, not by leaning too heavily on paleo jargon that can scare shoppers away.
Key Arguments: Food can materially affect energy, wellbeing, and performance; Smith’s own experience with paleo convinced her there was a consumer need for healthier pantry staples. A brand can win in a crowded category by making a healthier product taste great first and labeling it in a way that feels approachable rather than niche. Direct retail hustle matters early: in-store demos, cold calls, and face-to-face pitching were essential to getting shelf space and sell-through. Bootstrapping forces discipline; Smith stretched every dollar, used low-cost manufacturing hacks, and prioritized product over marketing in the early years. Scaling requires learning to delegate; as the company added senior leaders, Smith had to move from founder-doer to CEO and trust specialist expertise. Simple Mills’ growth came from both luck and relentless execution, including an influencer boost, timing with consumer trends, and persistent work over many years.
Data Points: Revenue: About $100 million - Current scale of Simple Mills as described in the introduction Store count: More than 28,000 stores in the US - Distribution footprint reached by the company by the time of the interview Year founded: 2012 - Caitlin Smith began the company after experimenting with paleo eating Initial Whole Foods order: 12 bags of muffin mix - The first purchase order after pitching a local Whole Foods manager Commercial kitchen spend: About $200 - Approximate cost over the first six months of manufacturing product Personal savings invested: About $70,000 - Smith used nearly all of her savings to fund the startup Family fundraising: $200,000 - Parents mortgaged their house after a deal with another investor nearly collapsed First institutional round: About $2 million - Raised after winning/co-winning the University of Chicago Booth New Venture Challenge Retail expansion demo output: About 600 mini muffins per 3-hour demo - Smith baked enough samples for in-store demos every weekend Amazon sales early on: 1-2 units per month initially - Early website/Amazon sales were very slow before influencer traction Amazon growth after influencer post: Sold out in about an hour - Danielle Walker’s post on Facebook caused a rapid spike in demand Amazon velocity: 50 to 100 units per day - After Amazon ranking improved, Simple Mills became a top-selling muffin mix Initial team size after fundraising: 5 people - Early hires included finance, operations, marketing, and sales support Whole Foods regional expansion: 3 regions - Pacific Northwest, Southern California, and Denver were the first regional Whole Foods wins Baking mix growth during COVID: Up 50% over prior year at times - Pandemic baking lifted the company’s baking mix sales
Pivotal Quotes: "The difference between success and failure is a few small disciplines practiced every day." — Caitlin Smith: A quote she kept above her desk to motivate daily cold-calling and consistent execution "It was a complete accident that I actually took the product into stores." — Caitlin Smith: She describes how a local Whole Foods pitch unexpectedly became the company’s first retail breakthrough "I think every year the business teaches me a different aspect of leadership." — Caitlin Smith: Reflection on how leadership skills evolved as Simple Mills scaled
Implications: The episode shows how consumer brands can grow by combining personal conviction, scrappy distribution, and disciplined product decisions. It also suggests that in food, taste and trust can beat trend labels, while founders must evolve from maker to manager to scale.
About How I Built This with Guy Raz
Guy Raz interviews the world’s best-known entrepreneurs to learn how they built their iconic brands. In each episode, founders reveal deep, intimate moments of doubt and failure, and share insights on their eventual success. How I Built This is a master-class on innovation, creativity, leadership and how to navigate challenges of all kinds.New episodes release on Mondays and Thursdays. Listen to How I Built This on the Wondery App or wherever you listen to your podcasts. You can lis...