Entrepreneur With Me

ABOUT THE EPISODEIn this episode of Entrepreneur With Me, Mayer sits down with DJ Chubby Rock, a veteran Jamaican DJ with over 30 years in the business, to trace his journey from sneaking out as a teenager to catch sets at House of Leo to becoming a fixture on the club, soca, and corporate event circuit across Jamaica and beyond.DJ Chubby Rock shares how his name came about, his early love of soul music passed down from his grandmother (who sang in clubs before turntables existed), and how vinyl, cassettes, and hustling Sound Clash tapes in school shaped his ear for music. He walks through decades of residencies — from Dr. Bird and Priscilla's, to Weekends, Peppers, and Acropolis — and reflects on the evolution of dancehall, soca, and disco, the rise of auto-sync technology, and what's been lost and gained as DJing shifted from vinyl and pure ear-mixing to digital convenience.The conversation also touches on his side venture running a barbershop next to a recording studio, his work on tours and weddings, playing on private yachts, and the advice he'd give any young DJ trying to break into the business professionally.KEY TAKEAWAYS• Reputation and reliability ("showing up on time, every time") matter more long-term than any single gig• Knowing the full history of a genre, not just current hits, builds credibility and range as a performer• Corporate and private events can pay significantly more per hour than traditional club nights• Technology (like auto-sync) has sped up and simplified DJing, but something is lost from the skill of ear-mixing by hand• Brand reputation and personal name recognition directly affect which gigs and sponsors a performer can access• Versatility, reading a room and mixing genres and eras, keeps a DJ in demand across different crowds• A side skill or business (like Chubby Rock's barbershop) can build transferable leadership and management experience• Longevity in a creative industry often comes down to integrity: keeping your word and building a name people trustBEST MOMENTS"I didn't want to give myself chubby rock. So I just said chubby rock.""You have to use your ears to mix. It takes a lot of practice.""If you're not taking care of the record, you're... hearing scratching sounds.""Show up on time. Every time. Don't book a date with somebody and cancel because you get more money from somebody else. Bad business.""Your name is one of the biggest things in the business, especially if you're professional.""I'm a man of my word... I don't like to make promises and don't keep them."FOLLOW OUR INSTAGRAM: entrepreneurwithmepodcastFOLLOW THE GUEST'S SOCIALS: c_rock_jaABOUT THE HOSTHosted by Mayer Morrison on Money Roundup, a podcast featuring honest conversations and personal lessons on entrepreneurship, content creation, and building a business from the ground up.Hosted by: Mayer MorrisonExecutive Produced by: Mayer MorrisonProduced by: Kyle ExellEdited by: Kyle Exell

ABOUT THE EPISODE In this episode of Entrepreneur With Me, Mayer sits down with Lamont Bourne, a former bookstore owner from Clarendon, Jamaica, to unpack the full arc of building and scaling a community-rooted business from the ground up.Lamont shares how he left a career at a university bookstore to open his own shop, Turning Pages, in rural Longville Park before expanding into Old Harbour and later May Pen. He talks candidly about forming a FedEx drop-shipment partnership, running back-to-school health fairs, sourcing books internationally, and building a loyal customer base through genuine, personalised service. He also opens up about the toll of repeated break-ins and rising crime, the tough decision to consolidate locations to protect his family, and why he ultimately chose sustainable, strategic growth over expansion for its own sake.The conversation closes with reflections on leadership, legacy, and the Jamaican proverb that still guides his thinking today: "one one cocoa full basket."KEY TAKEAWAYS • Being impactful and memorable in every interaction builds long-term loyalty far beyond any single sale • Market research and community insight can justify bold, unconventional business locations • Strategic partnerships (like a FedEx drop-shipment point) can diversify revenue without major overhead • Treating every customer — big spender or small — with the same care builds lasting word-of-mouth • Growth should match your comfort and capacity, not competitors' pace or pressure to expand • Family safety can and should outweigh business ambition when risk escalates • Strong internal culture and leadership at the top filters down to consistent customer service across locations • Small, consistent actions compound into meaningful long-term impact ("one one cocoa full basket")BEST MOMENTS "Once you treat people well, they're always gonna come back." "You have to be strategic about growth because getting too big can also harm you." "You recognize that it was about to change you, and that's not who I am." "Even to this day... people remembered about you. Those are the things that they carry." "Don't try wanting to do everything or too many things one time. Build from the ground up." "If you are given lemons you turn it into lemonade... it is your opportunity to do good with whatever hand you're dealt."FOLLOW OUR INSTAGRAM: entrepreneurwithmepodcastABOUT THE HOST Hosted by Mayer Morrison on Entrepreneur With Me, a podcast featuring honest conversations and personal lessons on entrepreneurship, content creation, and building a business from the ground up.______________________________________________________________Hosted by: Mayer Morrison Executive Produced by: Mayer Morrison Produced by: Kyle Exell Edited by: Kyle Exell

ABOUT THE EPISODEIn this solo episode, Mayer opens up about why he's starting a podcast in 2026 and takes listeners through his full podcasting origin story — from discovering the Podcasts app on his first iPhone in 2022, to launching his first scripted news show (also called Money Roundup) in 2023, to burning out trying to keep up with a weekly upload schedule while working full-time.Mayer shares the honest, sometimes painful path that followed: Instagram lives that flopped, a pivot to unscripted YouTube videos, six months of relentless daily Shorts, and a formative brush with a European podcasting agency that opened his eyes to just how big the podcasting industry really is overseas — including two visa rejections that stopped him from attending their training in person.He also breaks down how the concept for this show was born, blending guest interviews with two types of solo episodes — educational breakdowns and raw, unscripted vulnerability inspired directly by Alex Hormozi's personal reflection segments and Steven Bartlett's earliest, rawest Diary of a CEO episodes.KEY TAKEAWAYS• Podcasting is one of the most intimate media formats — the more time someone spends listening, the deeper their connection to the host• A fully scripted, research-heavy format can be unsustainable without support or a team• Tracking listenership across only one platform can hide your true audience size• Instagram and YouTube reward creators differently — testing multiple platforms reveals what actually works• Big life pivots (job loss, illness, burnout) often create the space needed to commit to a new path• Being part of a supportive creator community can completely shift your belief in an industry• The best podcast concepts often develop through pitching and conversation, not a whiteboard session• Mixing interview and solo formats lets a host highlight guests while still building a personal connection with the audience• Unscripted, vulnerable solo content tends to build a far deeper bond with listeners than polished, scripted contentBEST MOMENTS"The stories that you share on podcasts... are not things that you just share with any and anyone.""No one has ever stopped me and been like, Mayer, I like your podcast.""For about a good five seconds there was a thought that went through my head, like, I wonder if I'm really getting scammed.""I finally see why so many persons love Stephen Bartlett.""I want to be really authentic, really vulnerable. Just my deepest thoughts with you guys.""As much as this is therapy for me and me sharing... I want to know what it is that you want to know more of."FOLLOW OUR INSTAGRAM: entrepreneurwithmepodcastABOUT THE HOSTHosted by Mayer Morrison on Entrepreneur With Me, a podcast featuring honest conversations and personal lessons on entrepreneurship, content creation, and building a business from the ground up.

ABOUT THE EPISODEIn this solo episode, Mayer breaks down the real, unfiltered journey of starting entrepreneurship after losing his job in 2023 — from launching a financial education business and webinars, to nervous Instagram lives, to grinding out daily YouTube and Instagram Shorts for six months straight.Mayer walks through what worked, what flopped, and the lesson that changed everything: it's not about having the best product, it's about having the right audience. He shares how testing content (including an unplanned viral angle around UK politics and millionaire migration) revealed the different ways YouTube and Instagram algorithms actually reward creators, and why he ultimately had to step away from content creation to focus and rebuild with intention — leading him toward podcasting.He closes the episode with the three core reasons people become entrepreneurs: passion, job loss, and the need for a second income stream.KEY TAKEAWAYS• Your audience matters more than your product — the best offer can still fail with the wrong audience• Free value doesn't guarantee paying customers, even with strong engagement• Testing content direction reveals what the algorithm rewards, even if it's not the audience you want• YouTube rewards watch time and interaction; Instagram rewards consistency and volume• Entrepreneurship has no manual — the market is your only teacher• Sustainable growth sometimes means stepping back to protect focus and mental bandwidth• People generally enter entrepreneurship for one of three reasons: passion, job loss, or the need for extra income• Consistency compounds — early low-view content can build into real traction over monthsBEST MOMENTS"Your audience is the most important thing in business.""You can have the most amazing product and the worst audience and you just be frustrated.""I had to actually start doing deep breathing on the live to start it.""The algorithm sees you as someone who is active and who is speaking.""Entrepreneurship is not a straight walk in the park.""A lot of persons get into entrepreneurship because they're not being paid enough to live. They're being paid enough just to work."FOLLOW OUR INSTAGRAM: entrepreneurwithmepodcastABOUT THE HOSTHosted by Mayer Morrison on Entrepreneur With Me, a podcast featuring honest conversations and personal lessons on entrepreneurship, content creation, and building a business from the ground up.

On this episode of Entrepreneur With Me, Mayer Morrison welcomes Latoya Spence who went from working full time in corporate to working as a full time author, designer and artist. We touch on her journey, trials & tribulations and balancing both her work life and her home life as a mom.FOLLOW OUR INSTAGRAM: entrepreneurwithmepodcast FOLLOW THE GUEST'S SOCIALS: theyellowroom_studio ------------------------------------------------------Hosted by: Mayer MorrisonExecutive Produced by: Mayer MorrisonProduced by: Kyle ExellEdited by: Kyle Exell