Are You In? with ChicagoJon & Crys D.

About Are You In? with ChicagoJon & Crys D.

Welcome to ‘Are You In?’ The podcast where we break down the reality of tomorrow's technology and business, so today's culture doesn't get left behind. Hosted by Chicago John and Crys D. this is your weekly reality check at the intersection of Al, entrepreneurship, creativity and community. Let’s break down the Trend Desk and open up the text thread to deliver raw, honest insights without the expert jargon. The future is moving fast. Are You In?

Publisher

Jon and Crys D.

Category

business

Language

en

Explicit

No

First episode

7 Mar 2026

Latest episode

27 Oct 2026

Latest episodes

31 episodes in the feed.

1. 

   27 Oct 2026

   Why Your Phone Knows You So Well | Are You In? Podcast w/ ChicagoJon & Crys 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?

2. 

   19 Oct 2026

   Who's Really Making Money From Side Hustles?

   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.

3. 

   12 Oct 2026

   Brand Deals & Contracts: Protect Your Money as a Creator | Are You In?

   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?

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

1 ratings

Spotify

5.0 / 5

8 ratings

Contact Are You In? with ChicagoJon & Crys D.

Guest appearances

Does not typically book guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.