Founder2Founder with Aaron Spivak
Entrepreneurship isn’t just a career—it’s a relentless, all-consuming way of life.
Welcome to Founder2Founder a raw and unfiltered podcast where host Aaron Spivak pulls back the curtain on what it really takes to build something from the ground up. No sugarcoating, no overnight success stories—just deep, honest conversations with some of the most driven, underrated, and game-changing founders of our time. From brutal setbacks to game-changing mindset shifts, Aaron goes beyond the polished success stories to uncover the unglamorous, deeply personal side of building a business.
As a seasoned entrepreneur himself, Aaron goes beneath the surface and gets into the nitty-gritty of what it truly takes to succeed. He’ll dive into the habits, behaviors, and routines that set elite founders apart, the tactics and strategies that are working today, and the mindset shifts required to push through the hardest moments. Through raw personal stories, late-night struggles, and breakthrough moments, guests open up about what it really means to grow, not just as a founder, but as a person.
Each week, Aaron sits down with visionary entrepreneurs from high-growth startup founders to seasoned CEOs, for real, unfiltered conversations about the highs, lows, and everything in between. Whether you're scaling a company, launching your first venture, or just looking for inspiration, this podcast will give you the insights, motivation, and real-world advice you won’t get just anywhere. If you're ready to strip away the illusion and get real about what it means to build, sacrifice, and thrive, this is the podcast for you. Join us every Wednesday!
Founder2Founder with Aaron Spivak
How to Run Your Business with True Authenticity, Momentum and The Superpower of Being Unapologetically Yourself
In the first official episode of Founder2Founder, host Aaron Spivak along with Cohost Chris Meade, welcome Jake Karls. Jake is Co-founder and Chief Rainmaker of Mid-Day Squares, the better for you chocolate brand that went from a kitchen table idea to a North American sensation. Known for his unapologetic authenticity and refreshingly relatable approach, Jake has been recognized as a rising star in the business world. He made Forbes’ 30 Under 30 list for Food and Beverage, and is currently a finalist for EY’s Entrepreneur of the Year awards.
Jake shares his journey of embracing his superpower, being himself, to build momentum and scale a brand that is as real as it gets. He opens up about overcoming insecurities, the power of showing up in person, and why building friends, not just customers, has been the cornerstone of Mid-Day Squares' success. From dealing with investor pushback to navigating the pressures of being the face of a rapidly growing company, Jake’s insights are a masterclass in leadership and authenticity.
This episode is packed with actionable advice and real talk. Jake Karls is redefining entrepreneurship with authenticity and showing why embracing who you are might just be the ultimate business strategy. Be sure to rate the podcast and subscribe or follow on your favourite platform so you never miss a new episode, every Wednesday!
Chapters
00:02 - Introduction to the Founder to Founder Podcast
02:12 - How Jake Carl’s Energy and Confidence Started from Insecurity
03:23 - Overcoming Fear and Learning to Lean Into Strengths
05:56 - Finding the Right Role in Business and Letting Go of Ego
08:15 - The Power of Communication in Entrepreneurship and Partnerships
10:41 - How Conflict Can Destroy or Strengthen a Business Relationship
12:39 - The Challenges of Being a Public Figure and Representing a Brand
15:13 - Staying Authentic While Scaling a Business and Facing Public Scrutiny
17:25 - The Realities of Traveling Constantly and Maintaining Relationships
19:53 - The Sacrifices Entrepreneurship Demands and Finding Balance
24:06 - Why Communication and Therapy Are Key to Business Longevity
29:26 - Fear of Growing Up, Taking on Responsibility, and Losing Freedom
33:53 - How Proving People Wrong Became a Driving Force for Success
38:20 - Building a Personal Brand to Elevate Your Business and Career
42:03 - The Power of Showing Up and How It Opens Unexpected Doors
48:13 - How to Separate Your Identity From Your Business for Long-Term Growth
53:44 - The Role of Momentum in Success and How to Maintain It
1:01:18 - Identifying Energy Drainers and Protecting Your Time
1:07:06 - What Jake Would Tell His Younger Self About Life and Success
1:10:19 - Final Thoughts on Canadian Entrepreneurship and Community
Guest Links:
Instagram @JakeKarls_
Linkedin
Stay Connected!
Aaron Spivak:
Instagram @Spivak
Linkedin
The Founders Club
Website www.foundersclubofficial.com
Instagram @TheFoundersClub
Founder2Founder:
Instagram @Founder2FounderPodcast
TikTok @Founder2FounderPodcast
Youtube @Founder2Founder.Podcast
