PODCAST · business
Are You In? with ChicagoJon & Crys D.
by Jon and 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 leftbehind.Hosted by Chicago John and Crys D. this is your weekly reality check at theintersection of Al, entrepreneurship, creativity and community. Let’s break down the TrendDesk and open up the textthread to deliver raw, honestinsights without the expert jargon.The future is moving fast. Are You In?
Episodes
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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…
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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…
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AI Keeps Receipts: Can You Trust What You Put Into AI? | 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,...
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Stop Starting Over With AI
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…
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AI Is Getting Smarter. Are You?
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…
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Stop Learning AI. Start Using It.
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,...
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AI Can Do It. But Should It?
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…
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AI Is Everywhere. But Can You Trust It?
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…
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The Platform Raised the Rent
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…
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EVERYONE HAS THE SAME TOOLS
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...
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The AI Tool Trap
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…
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Fear Is Costing You More Than AI
Anthropic destroyed millions of physical books to train AI—and internal court documents suggest they never wanted the public to know. In this episode of Are You In?, ChicagoJon and Crys D. unpack one of the biggest AI controversies yet, from Project Panama and the $1.5 billion copyright…
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Smarter AI Is Costing You More Than You Think
Everyone wants smarter AI. Almost nobody is asking what it actually costs. Every new AI model promises better performance, faster answers, and more automation. But behind every breakthrough is a growing price tag—billions spent on infrastructure, rising cybersecurity threats, energy demands…
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You Don't Own Anything Online
What do you actually own anymore? From Spotify playlists and Adobe subscriptions to AI tools and social media audiences, more of our lives are built on access instead of ownership. The problem isn't subscriptions—it's believing you own something when you only have permission to use it. In this...
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Stop Feeling Guilty About Using AI
Remember when using Google for homework was considered cheating? Today, many professionals feel the same way about using AI at work—even as the world's biggest companies invest billions to build their future around it. In this episode of Are You In?, ChicagoJon and Crys D. explore why the real...
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You Don’t Own Your Platform
Four AI models launched in 30 days. Creator reach is dropping, algorithms keep changing, and too many entrepreneurs are still building their entire business on platforms they don't own. In this episode of Are You In?, ChicagoJon and Crys D. break down why audience ownership is becoming one of the...
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Why Access Won’t Save You When the Pressure Hits
Attention is not ownership. In this episode of Talk Data To Me, Chicago John and Chris D break down why creators, entrepreneurs, and business owners need to stop building only on platforms they don’t control. From AI tools and TikTok trends to email lists, content pillars, digital products, and...
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Attention Is Not Ownership (And It's Costing Creators Millions)
Everybody’s focused on being seen… but the people winning are making sure they actually own what people see. In this episode of Talk Data To Me, Chicago Jon and Chris D break down the difference between attention and ownership in the creator economy. From Taylor Swift’s likeness trademark moves…
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AI Tools vs Systems: Why Most People Lose When Tech Shifts
AI tools are everywhere, but tools alone are not what keep businesses alive when technology shifts. In this episode, we break down why most creators, marketers, and business owners fall behind when they chase the newest app instead of building real systems. We’re talking AI workflows, automation,...
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Talk Data To Me LIVE | AI Is Changing Everything (Again) — What You Missed This Week
This week on Talk Data To Me LIVE, we break down the biggest shifts happening in AI, creator economy trends, tech infrastructure, automation, and digital business strategy. From the latest AI news and platform changes to what creators, entrepreneurs, and small business owners should actually be...
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Talk Data To Me AI Fatigue is Here & Sora is Dead (What Creators Must Do Next)
The AI hype wave is cooling off… and the infrastructure era is here. ☕🎙️ This week on Talk Data To Me, Chicagojon and Crystal break down AI fatigue, the fall of Sora, why audiences are rejecting fake experts, and how creators can actually survive the next shift in the digital economy. We’re...
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Surviving the AI Pivot: Strategy, Content & The Future After Sora
AI is moving fast, and with all the conversation around OpenAI Sora, a lot of business owners and creators are wondering what’s next. In this episode, we break down the shift happening in AI, how to adapt instead of chasing every trend, and practical ways to actually use AI to grow your business,...
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Talk Data To Me | Al vs Search, Marketing Data Shifts & The Real Al Economy
In this episode of Talk Data To Me, we break down the real impact of AI vs search and what it means for the future of marketing. From major data shifts in digital marketing to how AI is reshaping search engines, content strategy, and online visibility, we cover what most people are missing right...
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AI Is Becoming Government Infrastructure | What Entrepreneurs Need to Know
Artificial intelligence is no longer just a tool. It is becoming part of the foundation of how systems operate. In this episode of Talk Data To Me, we break down how AI is evolving into government infrastructure and what that means for entrepreneurs, business owners, and creators. From public...
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What Everyone Missed This Week: AI, Markets & Social Media Trends LIVE
Stop waiting for headlines to tell you what’s trending. This week on Talk Data To Me, Chicago Jon and Crystal (Chris D Creates) break down the signals everyone else missed. AI isn’t hype anymore, it’s operational. If you’re not using it as your personal staff multiplier, you’re leaving money and...
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Talk Data To Me: How AI Is Changing Relationships, Money & Travel in 2026 (ChatGPT, Spending Trends & Lifestyle Hacks)
Welcome to Talk Data To Me — the podcast decoding how AI, money, and culture are actually shaping real life right now. No fluff. No surface-level takes. Just real insight into how people are moving in 2026. In this episode, we break down: ❤️ AI for Relationships & Communication How people are…
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What Actually Moves the Internet (And Your Money)
Everyone’s talking about trends—but what’s actually moving attention, money, and influence right now? In this episode, ChicagoJon and Crystal break down what’s really happening across social media, AI, and the creator economy. From TikTok and social search to real-time conversations on X and...
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Social Search, Real Talk: What’s Actually Moving Money, Attention & Power in 2026
Everyone’s talking about the weather. We’re talking about what actually moves attention, money, health, and power. In this episode of Talk Data To Me, we break down what’s really happening right now across social media, search behavior, AI, pop culture, and money—without the hype, fear-based…
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You’re Searching Wrong | AI, SEO & Social Media Truth
Most people are thinking about search completely wrong. In this episode of Talk Data To Me, we break down how people actually search in 2026 — and why traditional SEO thinking is no longer enough. What we really get into: How people actually search Why people don’t search for names — they search...
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Don't Be A Trend Zombie
In this episode we talk about the danger of becoming a “trend zombie.” Too many creators chase every viral sound, topic, or format without asking if it actually serves their audience. Just because something is trending doesn’t mean it belongs on your page. We break down how to recognize trends…
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ABOUT THIS SHOW
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 leftbehind.Hosted by Chicago John and Crys D. this is your weekly reality check at theintersection of Al, entrepreneurship, creativity and community. Let’s break down the TrendDesk and open up the textthread to deliver raw, honestinsights without the expert jargon.The future is moving fast. Are You In?
HOSTED BY
Jon and Crys D.
CATEGORIES
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Frequently Asked Questions
How many episodes does Are You In? with ChicagoJon & Crys D. have?
Are You In? with ChicagoJon & Crys D. currently has 30 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Are You In? with ChicagoJon & Crys D. about?
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 leftbehind.Hosted by Chicago John and Crys D. this is your weekly reality check at theintersection of Al, entrepreneurship, creativity and community. Let’s break...
How often does Are You In? with ChicagoJon & Crys D. release new episodes?
Are You In? with ChicagoJon & Crys D. has 30 episodes. Check the episode list to see recent publication dates and frequency.
Where can I listen to Are You In? with ChicagoJon & Crys D.?
You can listen to Are You In? with ChicagoJon & Crys D. on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Are You In? with ChicagoJon & Crys D.?
Are You In? with ChicagoJon & Crys D. is created and hosted by Jon and Crys D..
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