Are You In? with ChicagoJon & Crys D.

Do you have to be famous to build a successful business? Or do you simply need to be visible, memorable, and good at what you do?

In this episode of Are You In?, Chicago John and Crystal D. get into the realities of building a business in today's social media-driven world. From short-form video and personal branding to influencer marketing and customer trust, we're discussing what it really takes to get your business noticed without feeling like you have to become an entertainer.

Does every business owner need to be the face of their brand? Should corporations hire creators to represent them? And how can small businesses use social media to attract the right customers instead of chasing viral moments that may not even lead to sales?

We also discuss the importance of showing your personality, building relationships with your audience, creating content around common customer problems, and using your expertise to establish trust.

In this episode, we're talking about:

• Building a recognizable personal brand as a small business owner

• Why being visible matters more than being famous

• Short-form video, TikTok, Reels, and social media marketing

• Whether business owners need to become content creators

• Hiring influencers and employees to represent your brand

• Protecting your business when working with creators and employees

• Using AI while keeping your content authentic and human

• Finding your audience and turning attention into potential customers

• Why local businesses need community support and visibility

• Creating educational and entertaining content that builds trust

This week's challenge: Pick one thing you know how to do and explain it to someone who doesn't. Show your expertise, share your process, and let people see what makes your business valuable.

You don't need millions of followers to make an impact. You need the right people to find you.

Join the conversation: Would you rather buy from someone who's entertaining online or someone who's simply excellent at what they do?

Welcome to Are You In? with Chicago John and Crystal D.

Your phone knows more about you than you might think. 👀📱

In this episode of Are You In?, we're breaking down how artificial intelligence is already woven into our everyday lives, how companies use our data, and whether we're paying enough attention to our digital privacy.

From personalized ads and phone tracking to AI-generated art and small business marketing, we're having an honest conversation about who benefits from AI, how everyday people can use it, and why the conversation around AI isn't as simple as it seems.

Plus, we're sharing a practical challenge: a quick phone privacy audit to help you take a closer look at your settings and the information you're sharing.

In this episode, we discuss:

• How AI influences your everyday life—even if you don't use AI tools directly

• Why your phone seems to know exactly what you're interested in

• Data privacy, personalized ads, and tracking

• How AI can help with budgeting, planning, and everyday tasks

• AI-generated art and the debate around creativity

• Why small businesses are often judged differently for using AI

• Simple steps you can take to review your phone's privacy settings

💡 This week's challenge: Take 10 minutes to review your phone's privacy settings and see what information your apps can access.

AI is here, but how we use it—and how much of our personal information we share—is still worth questioning.

🎧 Listen, join the conversation, and tell us: Are you using AI, or is AI already using your data?

Welcome to Are You In?

Who's Really Making Money From Side Hustles? | Are You In?

Everyone is talking about side hustles, digital products, affiliate marketing, and passive income. But how much of the conversation is about building a real business, and how much is about selling the dream?

On this episode of Are You In?, Chicago John and Crystal D break down the side hustle culture we see across social media. They discuss how to evaluate income claims, why revenue doesn't always mean profit, the hidden costs of gig work, and the difference between creating something of value and simply selling something.

They also explore the stigma around teaching what you know, the risks of confusing passion with business, and how to recognize when someone is selling a lifestyle instead of a realistic opportunity.

Whether you're considering a digital product, exploring affiliate marketing, driving for a delivery app, or trying to turn a skill into income, this conversation is a reminder to look beyond the highlight reel.

In this episode:

• Side hustles versus building a business

• Digital products and passive income

• Revenue, expenses, and actual profit

• Evaluating income claims and success stories

• Startup costs and the economics of gig work

• Affiliate links and referral programs

• Turning your skills into something people will pay for

Before you buy into the next big opportunity, ask yourself: Are you building a business, or buying into somebody else's version of success?

Are you in?

Follow Are You In? with Chicago John and Crystal D for conversations about creators, business, social media, and the decisions behind making it work.

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?