Ep. 4 - Jake Karls - Mid-Day Squares, Costco, and the Chaos of Scaling a Startup

In this raw and inspiring episode, Jake Karls, co-founder of Mid-Day Squares, opens up about the highs and lows of building a breakout CPG brand. From navigating burnout and identity loss to surviving near-recalls and Costco rejections, Jake shares the unfiltered truth behind the hustle. He reflects on the power of storytelling, staying authentic, and why reconnecting with your inner child might be the ultimate entrepreneurial edge.

00:00:00 – The Nonstop Mind of a Founder Jake and Harrison discuss the mental load of entrepreneurship and how hard it is to “turn off.” They explore the importance of stepping outside your day-to-day environment to reset and avoid burnout.

00:04:01 – When Business Becomes Your Identity Jake opens up about losing his sense of self while building Mid-Day Squares. He reflects on how he forgot who he was outside of work and is now trying to reconnect with his passions and hobbies.

00:07:16 – Childhood Lessons, Sports, and Embracing Failure A conversation on how competitive sports shaped their mental toughness. Jake shares how rejection in youth sports and personal setbacks taught him to bounce back stronger.

00:12:01 – Hustle, Naïvety, and the Joy of the Early Days Jake recounts his first failed business and the wild energy he had in the early days—sleeping in cars, building brand momentum, and chasing the dream with childlike excitement.

00:17:31 – The Burnout That Changed Everything Jake details a 40-day mental and physical collapse, including symptoms he thought were MS. He shares how hypnotherapy helped him recover and how critical it is to listen to your body’s warning signs.

00:24:01 – Health Over Hype: Redefining Success Jake examines how chasing validation and constant movement took a toll. He discusses how eating well, moving daily, and getting quality sleep are now his non-negotiables.

00:30:01 – Why Jake Quit His CMO Role Jake explains how ego drove him to take on a role he wasn’t built for. After stepping down as CMO, he focused on his true strengths—brand energy, storytelling, and relationships—and the business improved because of it.

00:36:01 – Fans, Not Customers: Mid-Day Squares’ Storytelling Strategy The MDS team documented everything—from legal battles to product launches—like a reality show. This authentic storytelling helped them build deep emotional connections with fans.

00:42:01 – Breaking Into Costco After Years of Rejection After three years of hearing “no,” Mid-Day Squares got into Costco by breaking records during a roadshow. Jake talks about teamwork, conviction, and staying persistent until the deal landed.

00:47:01 – Final Advice: Learn to Dance Jake closes the episode with his biggest piece of advice to entrepreneurs: reconnect with your inner child, don’t lose yourself in the hustle, and learn to dance through the ups and downs.