Bay opens up about becoming more serious about music after his father was incarcerated, making pain music, building momentum in New York, working with artists like Lil Durk, G Herbo and Rich The Kid, and repeatedly getting close to his breakthrough without completely getting over the hump.

Eventually, that momentum led to a deal with Interscope Records around 2018. But what Bay thought would take his career to another level instead became another setback when the A&R who believed in him left the company shortly after he signed.

Bay says budgets stopped moving, communication changed, and his ability to release music slowed down.

Years and multiple situations later, Bay finally became independent.

Then came the timing that changed everything:

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In this episode of The Jay Hill Podcast, Biskit breaks down how his years in nightlife gave him the relationships, skills, and access that would eventually help him become an entrepreneur. He shares how R&B Mimosa Festival started from a simple idea, unexpectedly took off, and forced his team to quickly learn the difference between promoting an event and actually operating one.

Biskit also opens up about the business behind large-scale festivals, including marketing, vendors, staffing, liquor laws, touring into new cities, and why a full festival can cost around $100,000 to produce. He explains how the success of his events helped him expand into the restaurant industry, the lessons he learned from his first restaurant deal, and how relationships became a form of capital when he didn't always have the money himself.

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In this episode of The Jay Hill Podcast, Baltimore entrepreneur 7Streams sits down with Jay Hill for a wide-ranging conversation about his journey from the streets and prison to entrepreneurship, ownership, relationships, wealth, and building a life on his own terms.

7Streams opens up about spending roughly 11 years incarcerated throughout his life, including six years in federal prison, and explains why he doesn’t believe every formerly incarcerated person should be given the same blueprint for success. Instead, he believes people have to identify their individual gifts, strengths, and what they’re actually willing to work for.

The conversation then turns to money and independence, where 7Streams explains one of the philosophies that has shaped the way he does business:

“If you allow me to feed you, then you’re giving me permission to starve you.”

For him, financial freedom isn’t about looking rich. It’s about ownership, controlling how you make your money, employing your people, and building something that can’t disappear because someone else decides to “cut you off.”

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Yahki Awakened joins The Jay Hill Podcast for a deep and unfiltered conversation that goes far beyond herbs and holistic health.

Known for challenging conventional ideas about the human body, food, disease, and healing, Yahki breaks down his views on modern medicine, nutrition, spirituality, education, Black trauma, incarceration, and the experiences that transformed his life.

But this conversation isn't simply about what Yahki believes. It's also about why he believes it, where he's changed his mind, and why he thinks people should question everything — including him.

Yahki opens up about his journey from the streets and gang involvement to incarceration, studying the human body, and eventually dedicating his life to health and education. He discusses how trauma can shape individuals and communities, why environment matters, and how his own experiences ultimately pushed him toward a completely different purpose.

The conversation also tackles some of Yahki's most controversial views. He explains why he believes natural approaches to health deserve greater attention, while also making it clear that he doesn't believe holistic health means rejecting modern medicine altogether. Yahki even reflects on beliefs he's changed over the years and why receiving new information should sometimes force you to reconsider what you once thought was true

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There’s a side of Nino Paid that the music, social media, and public image don’t always show.

In what may be his most vulnerable interview yet, Nino Paid sits down with Jay Hill for an honest conversation about family, mental health, success, music, and the emotional weight that can come with experiencing everything you once wanted.

Nino opens up about meeting his biological family and how deeply the experience affected him mentally. He talks about crying, processing emotions he wasn’t prepared for, and eventually having to find his way back to a place where he could work and create again.

But that vulnerability carries throughout the entire conversation.

Nino explains how signing a deal changed his relationship with music, admitting that something he once did purely because he loved it eventually began to feel like a job. He discusses the pressure to recreate successful records, navigating meetings and industry expectations, learning when to network and when to protect his energy, and trying to remain creative when creativity becomes a business.

The conversation also explores his upbringing in Landover, Maryland, his time incarcerated and how being around people from different cities unexpectedly expanded his musical influences, the importance of hometown support, streaming, relationships, misconceptions about who he is, and the difference between the person people see and the person behind the music.

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In this episode of the Jay Hill Podcast, Omeretta joins Jay Hill for one of her most honest and thought-provoking conversations to date.

Known for her viral record "Sorry Not Sorry," Omeretta opens up about the truth behind the song, why she has no regrets, and the biggest misconceptions about how it impacted her career. She explains why she stepped away from music, why she refuses to chase trends, and why staying true to herself has always mattered more than fitting the industry's formula.

The conversation goes far beyond music as they discuss authenticity, social media, going viral, label expectations, and the pressure artists face to sacrifice who they are for success. Omeretta also shares her thoughts on building a lasting career, creating timeless music, and why she believes too many artists are chasing moments instead of legacies.

This is a conversation about choosing purpose over popularity and staying true to yourself in a world that constantly asks you to be someone else.

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Most people in the beauty industry believe success means getting more clients.

Selina Alexander believes that's only the beginning.

After spending more than two decades building a successful salon, Selina realized that working behind the chair alone wasn't enough to create long-term freedom. Today, her mission is to help beauty professionals stop relying solely on their hands and start building businesses, credit, funding, and financial security that will last long after they step away from the salon.

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Trishonna Helm

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A lot of people think the only way to make money is by working harder.

Long hours. Physical labor. Doing whatever it takes just to get by.

In this episode, we sit down with Abram Mitchell, who went from doing hard labor fixing car windows in the heat… to making real money in real estate.

Not overnight. Not by luck. But by finding a different path and committing to it.

We talk about how he discovered wholesaling, why it stood out to him, and how that one decision changed the direction of his life. From making his first deal to eventually building homes from the ground up, this conversation breaks down the real progression — not just the highlight moments.

This isn’t about skipping work.

It’s about understanding that there are different ways to apply it.

If you’ve ever felt stuck doing work that doesn’t move you forward, this episode might give you a different perspective.

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The crew talks through everything from house parties, Atlanta traffic, hosting events, DJ chemistry, and professionalism, to relationships, first arguments, emotional maturity, and what it really means to understand somebody instead of just wanting to be understood. Along the way, the conversation opens up into bigger topics like inclusion, internalized homophobia, representation in media, embarrassment, starting over, and how people grow through discomfort.

Later in the episode, the conversation takes a sharp turn into language, cultural ownership, and the controversy around Jack Harlow’s album title Ma’Nicca. That opens the door to a bigger debate about Black culture, appropriation, music, race, who gets access, and why some things hit differently when history is attached to them.

This episode is funny, honest, uncomfortable, and thoughtful all at once — the kind of conversation that bounces around naturally but still lands somewhere real.

If you’ve ever thought about professionalism, relationships, freedom, growth, or what it means to love a culture you didn’t create, this one is for you.

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Baltimore Mayor Brandon Scott joins the Jay Hill Podcast for an open and honest conversation about leadership, criticism, and the real challenges facing the city of Baltimore.

In this interview, Mayor Scott addresses the allegations surrounding the misuse of city funds and explains what actually happened behind the headlines. He also speaks candidly about everyday issues Baltimore residents care about — including potholes, infrastructure, and the responsibility of leading a city that is constantly under national scrutiny.

The conversation also dives into his public back-and-forth with Donald Trump, the pressure that comes with being a young Black mayor, and why he refuses to change who he is depending on the room he walks into.

More importantly, Mayor Scott talks about growing up in Baltimore, why he always believed he would one day become mayor, and what it means to lead the very community that raised him.

This episode goes beyond politics — it's a real conversation about purpose, criticism, authenticity, and the responsibility of leadership.

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Most entrepreneurs think if their business is making money, they should automatically qualify for funding. But that’s not how the system works.

In this conversation, financial strategist Rosie Thomas breaks down why banks and lenders often say no — even when a business appears profitable on the surface.

We talk about the real reasons entrepreneurs struggle to secure funding, how your financials are supposed to tell a story, and why bookkeeping, tax strategy, and proper financial structure matter more than most people realize.

Rosie also explains the difference between simply making money and building a business that looks stable and fundable on paper. Many entrepreneurs are leaving opportunities on the table because their financial records don’t properly reflect the strength of their business.

If you’re an entrepreneur, freelancer, or small business owner trying to grow, this conversation will help you understand how banks actually evaluate businesses — and what you can do to position yourself better.

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In this episode, he opens up about turning down traditional label structures, protecting his ownership, and why freedom was never negotiable — even while working with Roc Nation.

We talk about what independence really means in today’s music industry. Not “doing it alone,” but building real infrastructure, owning your masters and publishing, and creating leverage before signing anything.

LaRussell breaks down:

Why he said no to deals that didn’t align

What “non-exclusive” really means

How ownership changes your negotiating power

Why numbers don’t always reflect real life

The difference between support and control

Building a machine instead of chasing a moment

Confidence through competence

He also reflects on growth, ego, turning down opportunities early on, and how his perspective has evolved.

This isn’t a “labels are bad” conversation.

It’s a masterclass in leverage, discipline, and knowing your value before the world agrees with you.

If you’re an artist, entrepreneur, or anyone building something from the ground up — this episode will challenge how you think about independence.

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Jay Jay has been moving fast — viral skits, rapid growth, and real conversations behind the scenes of comedy and content creation.

In this episode of The Jay Hill Podcast, Jay Jay breaks down how his skits started gaining traction, what really happens once the motion starts, and why collaboration in comedy isn’t as easy as people think. He opens up about creator politics, egos, and the unspoken tension that comes with success — including addressing his beef with Finesse 2x and how situations like that change how you move.

This conversation isn’t about pretending everything is love. It’s about the reality of building momentum, navigating weird energy, and understanding why some comedians and creators hesitate to work together once things start clicking.

If you’re a creator, comedian, or someone trying to build something from the ground up, this episode gives an honest look at what comes with visibility — the good, the awkward, and the uncomfortable.

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A lot of people are making money.

Very few are actually building wealth.

In this episode, Jay Hill sits down with Marvin for a deep, honest conversation about what separates income from true financial freedom — and why earning more doesn’t automatically fix broken strategy.

This isn’t about hype, shortcuts, or get-rich-quick schemes.

It’s about structure, discipline, positioning, and using money intentionally instead of emotionally.

Marvin breaks down:

• Why many people feel stuck even as their income increases
• The difference between flash and foundation
• How losing structure can quietly destroy momentum
• Why discipline and systems matter more than motivation
• The mindset shift required to stop chasing and start positioning
• How wealth is built through strategy, not just earnings

A major part of this conversation focuses on using life insurance as a financial tool — not as a product pitch, but as a way to think differently about cash flow, liquidity, and long-term planning. Marvin explains how he uses properly structured policies to access capital, invest, and keep money working instead of sitting idle.

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In this episode, Jay Hill sits down with S3nsi Molly for an honest, unfiltered conversation about what really happens afterthe label, after the expectations, and after people think you’ve “made it.”

This isn’t a highlight reel.

It’s a real discussion about pressure, independence, faith, grief, comparison, and staying grounded while building your own path.

S3nsi Molly opens up about:

• The reality of going independent as an artist
• What people don’t see behind “success”
• Navigating grief and personal loss while still moving forward
• Her evolving relationship with faith and identity
• Why comparison can quietly derail your progress
• Learning to trust your timing instead of chasing someone else’s
• The mental and emotional weight that comes with independence

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In this episode, Jay Hill sits down with Chris Simon, a Baltimore-born entrepreneur and operator, to talk about what most motivated people never get taught: the rules of the game.

This isn’t about hype.

It’s not about quick money or shortcuts.

It’s about structure, exposure, relationships, and learning how to think like an owner — especially when you come from environments where hustle is praised but systems are never explained.

Chris breaks down how he went from creative hustles to building real businesses by learning:

how money actually flows

how to separate hustle from structure

how to build institutions instead of just personal brands

how to navigate grief, family, and responsibility while still growing

how exposure, relationships, and discipline changed his trajectory

This episode speaks directly to men who:

already believe in entrepreneurship

feel mentally cluttered or directionless

are tired of restarting every few years

come from inner-city environments like Baltimore, Atlanta, Houston, or NYC

want to build something that lasts

This is a reset conversation.

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In this episode, Jay Hill sits down with JD, an entrepreneur who went from survival mode to ownership by changing his mindset, getting in the right rooms, and building real systems — not chasing shortcuts.

This isn’t hype.

This isn’t “get rich quick.”

This is an honest conversation about discipline, faith, proximity, and creating options when you feel stuck.

We talk about:

• What to do when you feel motivated but directionless

• Why most people stay stuck even when opportunities exist

• How proximity to the right people can change your entire outlook

• The mindset shift required to move from survival to ownership

• Why discipline beats motivation every time

• How JD built income through modern investing strategies

• Why Airbnb isn’t dead — but the old way of doing It is

• How systems, automation, and patience create freedom

• Why rebuilding yourself quietly matters more than posting progress

This episode is especially for anyone who:

Feels pressure to “have it together” by now

Is tired of scrolling motivational content without real direction

Wants to start the year with clarity, not confusion

Is open to learning new ways to build income and ownership

You don’t need more motivation.

You need clarity, standards, and the right conversations.

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Most people think they’re broke because they don’t make enough money.

The truth? Many are losing money before it ever reaches their bank account.

In this episode, Jay Hill sits down with Michel “Money Makin’ Mitch”, a Certified Public Accountant (CPA) and tax strategist, to break down why so many people — especially entrepreneurs and creators — are unknowingly overpaying the IRS.

This isn’t about shortcuts or “tax hacks.”

It’s about understanding how the tax system actually works — and why it was designed to reward people who learn the rules.

We cover:

• Why taxes are the biggest expense most people ignore

• How the “ignorance tax” quietly drains your income

• The difference between being broke vs. being uninformed

• How entrepreneurs legally reduce what they owe

• When you should (and shouldn’t) pay yourself from your business

• What “write-offs” really mean (and what they don’t)

• How travel, vehicles, and even events can become legitimate deductions

• The biggest mistakes people make that cost them thousands every year

Jay also asks the real questions most people are afraid to ask — about paying yourself, setting money aside for taxes, and how much grace entrepreneurs actually get when they’re just starting out.

If you’ve ever felt like you’re working hard but not getting ahead…

This conversation will change how you look at money.

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