According to Freakonomics author and podcast host, Stephen J. Dubner, “The difference between success and failure is sometimes just…timing.”. At least that’s the argument he makes in his Episode 563, “How to Succeed at Failing, Part 3: Grit vs. Quit (Update)”, which Caleb & Chris reference in this week’s episode. They even play a short clip from that episode, which offers a really poignant and layered example of Dubner’s point.

Caleb & Chris then relate this concept to entrepreneurship, highlighting how atypical journeys and perceived failures might simply be nothing more than incorrect timing or a rigid definition of success. They encourage listeners to embrace their unique paths and not to succumb to negative self-talk, suggesting that even challenging experiences can be valuable, life-enriching (not defeating) lessons.

Check out this episode on the podcast player of your choice and let the guys know if you agree or disagree! Special thanks to Chris for editing this episode, and a very special thanks to the Freakonomics Podcast Team for producing valuable content that inspires and creates thought provoking discussion. We highly recommend all of our Sippi listeners check out their full episode here.

This week the guys offer a conversational overview of various topics. Their exchange begins with personal anecdotes about their work-life balance and social media interactions, including Caleb's "fishing for hate".

The conversation then transitions to a discussion about unique treats, specifically the "Sibateaux " and "Cronut," revealing their unusual origins and names.

Finally, the hosts explore the main subject of this week’s episode: the ethical obligations of small businesses, particularly regarding pricing and staying open, in light of current events like tariffs and inflation.

Check out their chat on the platform of your choice!

Special thanks to Indicium for editing this episode!

Back in December 2024, Caleb & Chris got a chance to interview two tech entrepreneurs and learn about their really cool app, FoodScout! Now roughly a half year later, Caleb & Chris sit down with one of those two guys again, Damion Dehart, and hear a ruthlessly transparent update on their startup journey.

The conversation highlights the challenges of pivoting a business, detailing the failure of their initial app due to high marketing costs and customer churn. Damion also discusses the abandonment of a second venture, a skill-based wagering app, one week before its launch, primarily due to a lack of capital. The episode then shifts to a discussion on their current endeavor, FoodScout Go!, a white-label online ordering system for restaurants.

If you want to hear what pivoting a startup is REALLY like, be sure to check out this episode (and also Episode 36 for some context)! A SINCERE thanks to Damion for his authenticity, honesty, and willingness to share how painful (but necessary) a pivot can be!

Special thanks to Indicium for editing this episode!

In this week’s episode, Caleb and Chris discuss a variety of topics, beginning with their recent two-week break from recording and Chris’ trip to catch a FIFA Club World Cup match, followed by the controversial role of frappes as a "gateway drug" to specialty coffee.

The main focus then shifts to a refresher of Chris’ frustration with previous mainstream podcast players and how they were either acquired or shut down, disrupting the user community and data. This frustration motivated Chris to develop his own podcast player web app, Alli, utilizing AI to build a platform that empowers users with listening analytics and community features, setting it apart from music-centric streaming services.

Needless to say, the guys REALLY want to know what you think about this project so please check it out at https://Alli.Media and give them some feedback! And hey, you can even listen to this very episode directly on Alli itself!

Special thanks to Chris for letting Zac take a break by editing this episode!

This week the guys talk with Fallon Dyle, a research & product development chemist and founder of Sustainovate, a manufacturing consulting company. The discussion covers her unconventional career path from forensic chemistry to starting her own venture after a pivotal professional event.

Sustainovate focuses on sustainable and innovative product development, offering services from ideation to manufacturing and distribution, with a strong emphasis on environmentally conscious practices and educating consumers about misleading product labeling. The conversation also touches on intellectual property protection, with Fallon sharing her beliefs on trade secrets versus patents for unique products.

Ever wondered how to get from idea to physical product? Then be sure to catch this episode on the podcast platform of your choice!

Special thanks to Indicium for editing this episode!

This week’s amazing interview is with Tommy Teepell, co-owner of Grin Coffee. Tommy tells the guys all about his incredible entrepreneurial journey. He recounts his homeschooling experience, early ventures in fashion design and toy invention, and the serendipitous start of Grin Coffee as a family hobby using a popcorn machine. Tommy emphasizes the role of community support and faith throughout the company's growth, from early struggles to expanding into a physical retail location - reminding us of the critical importance of passion, grit, and humility in overcoming obstacles and achieving success.

Want to be motivated? Want to be reminded that entrepreneurship is hard and that just because it’s hard that DOES NOT mean you are doing it wrong? Then take a moment to hear Tommy’s inspiring story on the platform of your choice!

Sincere thanks to Indicium for editing this episode!

This week the guys talk with Rita Mitchell, Director of the Pine Belt Small Business Development Center, and Lori Watts, President of the Marion County Development Partnership. They discuss the vital role their organizations play in supporting businesses, from startups to established enterprises, especially in times of crises like natural disasters, economic downswings, and even global pandemics!

The conversation highlights how these centers provide free, confidential counseling and connect entrepreneurs with essential resources – emphasizing the importance of planning, realistic expectations, and adaptability in the ever-evolving business landscape. They also take some time to discuss the impact of AI on small businesses and share insights on common pitfalls for entrepreneurs, such as seeking non-existent grants and insufficient market research.

If you have ever wondered how the SBDC or your local county development partnership can help take your company to the next level, be sure to check out this episode on the platform of your choice!

Special thanks to Indicium for editing this episode!

The week the guys talk about the 2016 movie, The Founder, a period drama that tells the story of Ray Kroc, a salesman who turned two brothers’ innovative fast-food burger joint (McDonald’s) into the biggest restaurant in the world.

Caleb and Chris reflect on Kroc’s ambition, persistence, and ruthlessness, and how any of these talents (when taken to their extreme) can do as much harm as good. The guys also take some time to reflect on entrepreneurship more broadly, including the challenges of starting a business, and the personal sacrifices involved, using Kroc’s story as a point of comparison.

The conversation touches on balancing ambition with personal life, the importance of persistence, and the realities of the business world compared to idealized social media portrayals.

Check out the guys’ chat about this movie on the platform of your choice.

Special thanks to Indicium for editing this episode!