Sippi

This week the guys have an amazing interview with special guest Garrett Rouse, an entrepreneur who shares his transformative journey from incarceration to starting a recovery-focused business. After receiving a 24-year sentence for drug-related charges, Rouse describes the harsh realities of Parchman Prison and how accidentally stepping on a psychology book sparked a profound shift in his perspective.

He eventually found purpose by...

In this episode, the guys discuss the evolving world of prediction markets like Kalshi and Polymarket. These platforms allow users to bet on the outcomes of future events, ranging from Super Bowl performers to geopolitical shifts. While the hosts note that these markets provide a richer data signal than traditional polling by requiring participants to risk money, they also express concern over insider trading and the potential for ...

AI is going to take our jobs!!!  Have you heard this statement yet?  Better said, have you heard this statement a million times yet? Well, this week the guys interview someone who tells Caleb and Chris from firsthand experience that we have a right to be concerned!

The guys have a really interesting and technical conversation with full-stack web developer Jody LeCompte, who discusses the rapid evolution of technology and ...

This week the guys interview Tom and Hector Boldo, co-founders of the Mississippi Latinx Art Association and Nuestro Arte gallery in Hattiesburg; fellow co-founder Jacqueline Gonzalez Wooton was unfortunately unable to join them for the conversation. The couple shares experiences about their move from Austin to Mississippi and their subsequent efforts to increase Latin cultural representation through community workshops and themed ...

This week the guys interview Jordyn Williams, one of the founders and master franchiser of Grit + Grind Coffee. Williams details her rapid transition from a special education teacher to a business leader, growing their brand from a single mobile trailer in 2023 to roughly 16 locations by 2026! She explains how a partnership with founders in Alabama helped her shift from licensing to a formal franchise model that maintains strict br...

In this podcast episode, the guys explore the rapidly evolving and sometimes unpredictable world of artificial intelligence. Chris shares a humorous (and embarrassing) correction regarding a drone company's chatbot that turned out to be a real human employee, highlighting how difficult it has become to distinguish AI from people. 

The discussion shifts to autonomous AI agents participating increasingly more in the offic...

In this episode, Chris and Caleb discuss Pomelli, an experimental AI-powered marketing tool from Google Labs. By simply inputting as little information as a website URL, the software can instantly identify a company's brand DNA, including its values, aesthetic, and tone of voice.

The hosts demonstrate the tool's efficiency by generating social media campaigns and animated content in minutes, tasks that traditionally require signific...

This week the guys interview Brandi Perry, a local entrepreneur and educator from Columbia, Mississippi. Perry details the evolution of her travel and tourism brand, Backroads and Burgers, which she co-founded to highlight small businesses and hidden gems across the Southeast. The conversation explores her transition from a hobbyist blogger to a professional content creator who partners with tourism bureaus to promote regional trav...

For the first episode of 2026, the guys have a fun chat with writer and history enthusiast, Caleb Barrett. Before getting to the good stuff, the three drink some “Fairy Smut” and talk about the season finale of Stranger Things.

The conversation with their special guest then shifts to the cultural impact of small-town life and the preservation of local heritage. Barrett shares his personal journey of returning to his root...

This week the guys talk with Kevin Sibley, entrepreneur, cinematographer, and motion graphics artist. The guys talk with Sibley about his career journey, which began with making home movies on a VHS camcorder and progressed through working in news production - including the unexpected virality of a leprechaun news segment he filmed (which, according to Wikipedia, has over 28 million views at the time of this writing).

Sibley shares ...

This week the guys discuss a major capital expenditure (CAPEX) decision for Caleb's coffee shop business! Caleb is contemplating purchasing new, cutting-edge roasting equipment from a young company which would expand his business into the coffee supply chain by allowing him to roast beans in-house. 

They examine the potential 18-month return on investment (ROI), the risks associated with the new technology, and the stra...

This week the guys get to talk with Family & Psychiatric Nurse Practitioner and serial entrepreneur, Michael Schepemaker. The conversation centers on Michael's diverse business ventures, including his and his wife's journey in the clothing boutique industry (which he confesses began to flourish after he became less involved), ultimately allowing them to pay off their house.

They also discuss his entry into commercial real estate...

This week, Jory Scott takes the guys on a journey from bullfighter to bio-tech pioneer! Jory discusses his unconventional career path from being a top-ranked professional bullfighter to an occupational therapy assistant, athletic trainer, and ultimately a leader in the medical field of biologics and stem cell therapy.

Caleb & Chris focus the core of their discussion on Jory's work, particularly his companies’ potentially p...

“Just do the next right thing.” – Wise words of advice from this week’s guest, Lindsey Fredman. Lindsey sat down with the guys to discuss her varied career path and the launch of her business, Main Street Collective. Fredman shares her experiences from teaching and human resources, to working with the military and the U.S. Customs and Border Protection, highlighting her dedication to service.

T...

In May of 2024 the guys had an awesome interview with Mississippi Veteran and Entrepreneur, Ric McCluskey.  In that interview Ric hinted that he was starting on a new project, so the guys thought it would be fun to circle back with him (over a year later) and find out whatever happened with that project – and wow, a LOT has happened since that time!

This week Ric tells the guys how his new company, FlyBy Shine, utilizes l...

This week the guys have something of a riff episode where Caleb shares a CRAZY story that happened literal hours before recording.  Caleb shares a premonition to drive in the left lane, which he ignored, only to narrowly avoid a head-on collision with a truck driving in the wrong lane. The following day, while driving his wife's vehicle, Caleb experiences a mysterious incident where his airbags deploy without impact, severely ...

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 reall...

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...

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...