Why Most Founders Fail: Midday Squares’ Jake Karls on Building in Public

For Episode 3, we're joined by Jake Karls, co-founder and Chief Rainmaker of Midday Squares, the chocolate snack company that grew from a tiny condo kitchen in Montreal to more than 10,000 stores across North America. Jake shares why authenticity beats perfection, how building in public helped Midday Squares stand out in a crowded market, and the lessons he learned from multiple failed businesses before finding product-market fit. We also dive into entrepreneurship, storytelling, burnout, hiring, content creation, and what it really takes to build a lasting company.

In this episode, we cover:

• Why building in public creates stronger customer relationships

• The importance of product-market fit before focusing on growth

• How Midday Squares went from 50 bars per day to 150,000+ per day

• Why authenticity wins in a world full of AI-generated content

• How posting online led to fundraising, partnerships, and growth opportunities

• The biggest mistake Jake made in his first failed startup

• Why founders should focus on their strengths instead of their weaknesses

• How to build teams with complementary skill sets

• Lessons from burnout and sustaining high performance over the long term

• Why the people who stay in the game the longest often win the biggest

If you're a founder, creator, operator, student, or anyone trying to build something meaningful, this episode is packed with practical lessons on entrepreneurship, storytelling, resilience, and building a business that lasts.

#Entrepreneurship #Startups #MiddaySquares #ConsumerBrands #BuildingInPublic #FounderStory #ProductMarketFit #LinkedIn #ContentCreation #BusinessGrowth #ZeroToOnePodcast #StartupAdvice