Are You In? with ChicagoJon & Crys D.

Want brand deals, sponsorships, and paid collaborations? Make sure you're protecting your money before you sign.

On this episode of Are You In?, Chicago Jon and Chris D. break down why content creators, freelancers, and entrepreneurs need contracts, what to look for before signing, and how AI tools like ChatGPT, Gemini, and Claude can help you understand the fine print.

From payment terms and deadlines to content ownership, usage rights, revisions, and deliverables, this conversation covers the business details creators can't afford to ignore.

Plus, learn how AI can help you draft a first agreement, explain confusing legal language, compare contracts, and identify missing clauses. Just remember: AI can make mistakes, so review everything carefully and seek qualified legal advice when needed.

In this episode, we discuss:

- Why creators need contracts for brand deals and sponsorships

- Content ownership, usage rights, and perpetual licensing

- Payment schedules, deadlines, deliverables, and revisions

- How AI can help you review and understand agreements

- Protecting your personal information when using AI

- Building a creative business that protects your time and money

Whether you're a content creator landing your first collaboration or an entrepreneur building a growing business, it's time to treat your work like a business.

The best time to have a contract is before the money comes.

🎙️ Are You In? with Chicago Jon & Chris D.

📺 Join us live Wednesdays at 1 PM EST and let's talk content, business, data, and opportunity.

Are you in?

AI can create almost anything these days, but what happens to the information you give it?

On this episode of Are You In?, Chicago Jon and Chris D. get into the reality of using AI in everyday life, business, and content creation. From digital footprints and privacy to AI-generated content, research, business organization, and the information we willingly hand over to technology, this conversation is a much-needed reality check.

They talk about why AI keeps receipts, how your digital information can come back later, why you shouldn't blindly trust AI-generated information, and how creators and entrepreneurs can actually use AI as a tool instead of chasing every new trend.

Plus, they get into using AI for things like researching your own emails, finding opportunities, improving workflows, creating content faster, and even helping you think twice before sending that angry text. 😂

The question isn't whether AI is here.

The question is: Are you using it wisely?

🎙️ Are You In? with Chicago Jon & Chris D.

📺 Join the conversation live Wednesdays and tell us...

If every AI conversation starts from zero, you’re probably spending way too much time repeating yourself.

On this episode of Are You In?, Chicago Jon and Crysd break down why random AI chats can leave your work scattered—and how dedicated AI projects can help you build a more organized, consistent workflow.

They get into setting up projects with the right context and instructions, keeping important conversations and resources together, and avoiding the constant cycle of explaining your business, goals, voice, and work all over again.

But there’s another side to it: your AI workspace shouldn’t be the only place your important information lives. They also talk about keeping your original files and source material backed up somewhere you control.

The goal isn’t to keep retraining AI every day. It’s to build a system where the AI already has the context it needs so you can get straight to the work.

Stop starting over. Build the project. Keep your files. Own your work.

AI keeps getting smarter. The bigger question is whether we are getting better at using it.

On this episode of Are You In? with ChicagoJon & Crys D., we’re talking about how AI is changing content creation, work, money, research, and everyday decision-making.

We’re getting into:

• Using AI to find opportunities hiding in your email and workflow

• AI-written content versus using AI to improve your own ideas

• Whether creators are becoming more productive or more dependent

• Using AI for brand deals, research, negotiation, and follow-up

• What happens when one creator uses AI as part of their workflow and another does everything manually

• Where human judgment still matters

The question for today:

Are you using AI to make more stuff, or are you using AI to make better decisions?

Join ChicagoJon and Crys D. live and bring your opinion to the conversation.

A new AI model drops, everyone rushes to try it, and suddenly the project you were supposed to finish last week is still sitting there.

In this episode of Are You In?, Chicago Jon and Crys D. talk about the difference between learning about AI and actually using it to move your business, content, and goals forward.

They break down how creators and entrepreneurs can use tools like ChatGPT, Claude, Gemini, NotebookLM, and other AI platforms for research, planning, analytics, content creation, outreach, email management, websites, and everyday business systems. But the bigger question is: are you actually executing?

The conversation also gets into setting measurable goals, using real data instead of guessing, avoiding shiny-object syndrome, improving your workflow, finding missed brand opportunities, building creator portfolios, reaching out for collaborations, and using AI to support your ideas instead of replacing them.

Because having access to the newest AI tool doesn’t give you an advantage if you never finish anything.

The play is simple: pick the goal, use the tool, measure the result, and execute.

AI can do more than ever—but should it do everything?

In this episode of Are You In?, Chicago Jon and Crys D. talk about the growing role of artificial intelligence in business, content creation, marketing, research, and everyday decision-making. They break down the difference between using AI as a helpful tool and relying on it so heavily that you stop thinking for yourself.

From AI-generated ads and “AI slop” to ChatGPT, Claude, Gemini, Canva, automation, small business marketing, and creative work, they explore where AI can actually save time and money—and where human judgment still matters most.

They also discuss why small business owners are often criticized for using AI while major corporations are already building it into their operations, how creators can use AI without losing their voice, and why chasing every new AI tool may be less valuable than learning how to use a few tools well.

The lesson isn’t to avoid AI. It’s simple: use the technology, but don’t stop thinking.

AI is everywhere—but can you actually trust it?

This week on Are You In?, Chicago Jon and Crys D. are cutting through the AI hype and talking about what it really looks like to use artificial intelligence without handing over your creativity, judgment, or common sense.

From AI-generated content and “AI slop” to privacy, environmental concerns, automation, and the growing pressure to learn every new tool, they break down where AI actually helps—and where humans still need to stay firmly in the driver’s seat.

They also get into choosing the right AI tools for your workflow, using AI for the boring back-end work instead of automating your relationships, and why the people who win probably won’t be the ones using the most AI. They’ll be the ones who know where AI ends and their humanity needs to begin.

If you’ve been wondering whether you should embrace AI, avoid it, or figure out somewhere in between, this is your reality check.

Are you in?

Every platform eventually reprices access. YouTube just proved it.

Beginning February 1, 2027, YouTube is raising the bar for new creators entering the Partner Program. But this episode isn't really about YouTube.

It's about what happens when someone else owns the platform your business depends on.

In this episode of ARE YOU IN?, Jon and Crystal break down the business model behind YouTube's latest monetization changes, why platforms always change the rules, and how creators can build businesses that aren't dependent on someone else's algorithm or policies.

In this episode:

- What YouTube's new Partner Program requirements really mean

- Why every platform eventually reprices access

- How to follow the business model instead of the headlines

- Why creators should measure business, not just views

- How to build infrastructure instead of just content

- The one audit every creator should complete this week

This Week's Homework

Record one long-form video.

Create three Shorts from it.

Add one email signup or community invitation.

Track movement—not just views.

The creators who survive aren't the ones with the biggest audience.

They're the ones who own the relationship.

Technology Shifts Power. Are You In?

🎙 Live Wednesdays at 12 PM CT on YouTube, TikTok, and LinkedIn

🎧 Full episodes available on Spotify, Pandora, and Amazon Music

What happens when everyone gets access to the same technology?

The advantage moves.

This week on ARE YOU IN?, Jon and Crystal look at what happens after AI, social media, video, and other business tools become available to everyone.

We break down why execution is becoming more important than access, how communities are becoming part of the search process, the five types of capital every entrepreneur should understand, and what billions of dollars flowing into AI infrastructure tell us about where business is headed.

If everyone in your industry had the same tools tomorrow, why would someone still choose you?

That’s the question.

ARE YOU IN?

#areyouin #businessstrategy #entrepreneurship #ai #smallbusiness #blackbusiness #creatoreconomy #businessnews

Everyone is looking for the next AI tool. Almost nobody is building the systems that actually create lasting businesses.

In this episode of Are You In?, ChicagoJon and Crystal explore what separates creators who chase every new AI trend from entrepreneurs who build businesses that continue growing long after the latest tool disappears.

From Hank Green's viral conversation about trust to the growing backlash against AI-generated content, this episode dives into why ownership, systems, and consistency matter more than chasing every new technology.

In this episode:

Why everyone wants the next AI tool

What Hank Green teaches us about trust in the AI era

Why audiences are rejecting AI slop

Black Business Month and the importance of ownership

How systems outperform shiny new tools

One simple challenge to make your business stronger this week

This week's challenge:

Don't download another AI tool. Improve one system you already have.

Technology shifts power—but lasting businesses are built on systems, trust, and ownership.

Technology Shifts Power. Are You In?

🎙 Live Wednesdays at 12 PM CT on YouTube, TikTok, and LinkedIn

🎧 Full episodes on Spotify, Pandora, and Amazon Music