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.

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.

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

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.

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.

Before acting, before Power Book IV: Force, before the cameras and recognition—Isaac was chasing the NFL. And when that dream ended, he didn’t just lose a career… he lost a sense of who he was.

In this powerful conversation, Isaac opens up about what really happens when success is taken from you, how losing football forced him to confront shame, ego, and identity, and how acting ultimately became the unexpected path that saved him. He shares the reality of going from professional sports to rock bottom, navigating faith during moments of doubt, and learning how to rebuild his life without letting bitterness take over.

This episode isn’t just about sports or television—it’s about reinvention.

Isaac reflects on the emotional toll of starting over, the discipline required to transition from athlete to actor, and why Power Book IV: Force represents more than a role—it represents the birth of a new chapter built on purpose, patience, and self-belief.

If you’ve ever had to let go of a version of yourself you thought defined you, this conversation will resonate deeply.

Akea J is one of the rawest, realest voices in comedy today — but the journey behind that honesty has been painful, complicated, and expensive. In this powerful and unfiltered conversation, she sits down with Jay Hill to reveal the truth about what it really takes to survive and succeed as a Black woman in a male-dominated comedy industry.

For the first time, Akea opens up about the battles she fought behind the scenes: being silenced, being overlooked, being mistreated, being blamed for things she didn’t do, and even being sexually assaulted in spaces where she was supposed to be protected. She shares the emotional toll of being punished by association, blackballed without explanation, and left to navigate an industry where power, ego, and silence often matter more than skill or integrity.