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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 teaching re-entry classes and serving as a peer support specialist upon his release. Rouse is now launching an accountability app that uses AI and facial recognition to provide third-party drug testing for individuals in recovery. This technology aims to preserve healthy relationships by removing the need for loved ones to act as "probation officers."
The discussion highlights how personal suffering can be converted into meaningful growth and innovative solutions for the entrepreneurial journey. Want to feel truly inspired today? If so, this is an episode you donât want to miss! Be sure to check it out on the podcast player of your choice.
A HUGE and SINCERE thanks to Garrett for sharing his powerful story!
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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 market manipulation.
The conversation highlights the ethical complexities of profiting from âmaterial non-public informationâ and the risks of incentivizing bad actors. Ultimately, the speakers reflect on the scary implications of these tools and emphasize the need for transparency and spiritual grounding in an increasingly speculative world.
Oh, and Caleb talks about how is getting old and officially got his AARP card. =)
Check out the episode on the podcast platform of your choice!
Special thanks to NPRâs Marketplace for the podcast clip! -
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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 its impact on the labor market. He reflects on his journey from a 90s "internet kid" to a specialized tech professional thatâs now facing modern AI-driven industry shifts that not only is impacting his personal livelihood, but his entire industry.
LeCompte explores the transition from the mobile app era to the current artificial intelligence epoch, noting how tools like Claude and ChatGPT are now performing tasks once reserved for senior engineers (like him). He encourages entrepreneurs to experiment with AI to automate menial tasks, suggesting that while the technology presents unprecedented challenges (employment and otherwise), it also offers a chance to reclaim time for human connection and faith. Ultimately, the conversation highlights the necessity of reskilling in a world where the boundary between human intelligence and machine automation is increasingly blurred.
Curious about what AI is doing to industry now and not five years from now? Then this is definitely an episode you donât want to miss!
Special thanks to Jody LeCompte for getting behind the mic and telling his fascinating story! Be sure to check out this episode on the podcast player of your choice!
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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 exhibitions. They describe their very early and necessary strategic pivot from exclusively showcasing Latin artists to inviting all local creators to reinterpret Latin themes, which successfully grew their network to hundreds of participants.
The conversation explores the cultural significance of traditions like DĂa de los Muertos along with the challenges of navigating artistic insecurity and local skepticism. Hector and Tom also candidly share the economic realities of running an art gallery while aiming to build empathy and visibility for the Hispanic community through public events like downtown parades.
Wanna hear about starting a new art gallery and association in rural America, or curious about the business side of being an artist? Then donât miss this episode! Be sure to check it out on the podcast player of your choice!
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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 brand standards.
Williams attributes her "whatever it takes" mentality to her childhood battle with leukemia, which instilled in her a profound sense of resilience and grit. Now operating as a corporate executive, she emphasizes the importance of mentoring her staff and finding unique opportunities in small-town markets. The conversation highlights her commitment to core values like spreading light and working hard while pursuing aggressive nationwide growth.
Wanna hear a story on hypergrowth? Wanna hear about what happens when you really commit to a grit and grind mentality? Then this is an episode you donât want to miss! Check it out on the podcast player of your choice!
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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 office (as tested by Season Two of Shell Game), and even in their own social network ("Moltbook") where bots engage in deep theological and economic debates without human intervention. A cautionary tale is also shared about an AI agent that fraudulently used a stolen credit card to order food for its owner after analyzing his schedule and caloric needs. To conclude, Caleb introduces a new AI voice assistant for his coffee shop designed to handle phone orders while filtering out rude customers.This overview emphasizes both the innovative potential and the significant risks associated with giving AI tools access to personal data and the internet. Check out this chat on the podcast player of your choice!
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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 significant time or expensive agencies. They emphasize how this technology empowers small business owners who lack the budget or expertise to maintain a consistent online presence. Ultimately, the conversation explores the broader impact of artificial intelligence on professional labor and the importance of adapting to these digital innovations.
Check out this episode on the podcast platform of your choice!
Shout out to Ric McCluskey for telling us about this incredible tool!
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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 travel.
Perry shares insights on the necessity of brand adaptation, the power of video content in social media algorithms, and the challenges of balancing a creative business with a full-time career. Additionally, she discusses her current initiative to rebrand the company to better reflect its broad focus on travel beyond just food destinations.
Want some advice utilizing authentic digital marketing to reach new demographics? Then this is an episode you definitely want to check out on the podcast platform of your choice!
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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 âFairy Smutâ 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 roots after college and explains his passion for documenting some disappearing traditions through his email newsletter. He emphasizes the importance of learning from older generations and using nostalgia as a tool to maintain a community's identity. The episode concludes with a focus on the value of human connection and the spiritual foundations that guide Barrettâs life and work.
Wanna learn more about his small-town life and how to better appreciate the one you come from? Then check out this weekâs episode on the podcast player of your choice!
Special thanks to Patrick Patrikios for letting us use his cool song âCruise controlâ on this weekâs episode!
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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 insights into his decision to become an entrepreneur and freelancer, discussing the challenges of marketing and the benefits of specializing in niche production skills like motion graphics. The conversation also touches on the changing media landscape, the impact of AI and other creative technologies on content creation, and wraps up with Sibley providing some advice for aspiring content producers.
Check out this episode on the podcast player of your choice! Special thanks to Chris for editing this episode!
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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 strategic shift required to transition from solely a coffee shop to a coffee shop + roastery. Chris emphasizes the value of investing vertically within the current industry to mitigate risk and cautions against making decisions based on boredom, urging Caleb to be an objective "consultant to himself". The discussion concludes with an appeal to listeners for feedback on the challenging but important decision!Wanna weigh in on what Caleb should do? Check out the episode on the platform of your choice! Special thanks to Chris for editing this episode.
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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 and his pursuit of a medical career, emphasizing the importance of faith, mitigating risk through skill and experience, and the aspects of running a business with a spouse. Michael stresses the need to overcome the fear of the unknown and the notion that success is found in contentment and serving as a good steward of one's time and resources.
You can listen to Michaelâs chat with the guys on the podcast platform of your choice. Sincere thanks to Michael for getting behind the microphone with the guys and thanks to Chris for editing this episode!
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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 companiesâ potentially positive impacts in treating conditions like autism, ALS, and chronic traumatic encephalopathy (CTE) â where Jory used his own cell therapy on himself to test its effectiveness, due to prior concussions from his bullfighting career.
He details the scientific basis and ethical considerations of their adult-derived stem cell process, addressing common misconceptions and the challenges of operating in a complex, competitive, and highly scrutinized medical sector. Jory also offers advice for small business owners on the importance of self-awareness and seeking honest counsel to achieve success.
Listen to Joryâs fascinating professional journey on the podcast player of your choice!
Special thanks to Chris for editing this episode!
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âJust do the next right thing.â â Wise words of advice from this weekâs 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.
The conversation also explores the challenges and triumphs of building Main Street Collective, an online marketplace for Mississippi artisans, including the importance of automation, trusting others, and navigating the departure of a founding business partner. Fredman also provides advice for aspiring entrepreneurs and discusses the uniqueness of both her business model and her local/Mississippi vendor base.
If you want to hear a candid story about what itâs really like to start a business while also being a parent, a spouse, and a full-time employee, this is an episode you donât want to miss! Check it out on the podcast player of your choice!
Special thanks to Chris for editing this episode!
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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 â and wow, a LOT has happened since that time!
This week Ric tells the guys how his new company, FlyBy Shine, utilizes large drones for pressure washing and soft washing commercial and industrial buildings. Ric discusses the challenges and triumphs of building his new business, including the initial anxiety of scaling, the importance of branding in a niche market, and the difficulties encountered during the first winter of operations.
He shares insights into expanding the company through a licensing model as an alternative to franchising, the crucial need to delegate tasks and avoid being the sole "touch labor" provider, along with the impact of entrepreneurship on family life. The conversation also explores the future of the drone and AI industries, emphasizing the importance of embracing new technologies for small business owners and preparing the next generation for a tech-driven workforce.
Special thanks to Ric for getting behind the mic with the guys and bringing the Sippi Community up to speed on what itâs really like to get a new project off the ground (quite literally)! *Insert the punny joke sound effect. *
Special thanks to Chris for editing this episode!
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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 damaging the car and leaving him with a potential concussion and a perplexing mechanic's screwdriver found in the engine. Chris then shares a personal story of a severe concussion he sustained as a teenager, highlighting the disorienting effects of head injuries.
Despite Caleb's potentially concussed state, the two continue recording, emphasizing their commitment to the podcast and attributing the week's events to divine protection.
Check out this bizarre series of events on the podcast player of your choice!
Special thanks to Chris for editing this episode!
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According to Freakonomics author and podcast host, Stephen J. Dubner, âThe difference between success and failure is sometimes justâŠtiming.â. At least thatâs the argument he makes in his Episode 563, âHow to Succeed at Failing, Part 3: Grit vs. Quit (Update)â, which Caleb & Chris reference in this weekâs episode. They even play a short clip from that episode, which offers a really poignant and layered example of Dubnerâs 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.
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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 weekâs 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!
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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!
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In this weekâs episode, Caleb and Chris discuss a variety of topics, beginning with their recent two-week break from recording and Chrisâ 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 Chrisâ 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!
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