Mind the Machine

What does AI actually change about how businesses operate?

In this conversation, Wiley Jones (co-founder and CEO of Doss) breaks down the real shift happening right now — and why most people are thinking about it the wrong way.

From the evolution of computing (mainframes → cloud → AI) to the rise of “AI-native” companies, this episode explores how work is being redefined… and what actually matters if you want to build something that lasts.

This isn’t about tools. It’s about how you think.

The IQ Era: https://www.linkedin.com/pulse/recap-mwc-final-day-iq-era-cheryl-k-goodman-tsuic/

00:00 Opening: “You can’t escape who you are”
00:13 Intro to Wiley Jones and Doss  
01:06 What Doss does (explained simply)  
03:00 The architecture shift behind AI  
05:50 Should companies rebuild everything for AI?  
08:02 What actually matters in an AI-driven world  
10:06 What machines vs humans should focus on  
11:54 Why understanding your business matters more than AI  
13:30 Wiley’s path and early lessons  
15:17 Why great products still fail  
21:15 Finding your “thing” (the constellation idea)  
23:00 Why conviction matters in building anything  
25:08 The myth of “AI magic”  
28:10 How to actually start using AI today  
32:09 The truth about hallucinations and limitations  
37:54 The future of AI and society  
41:52 What Doss is building and who it’s for

AI is rapidly transforming how work gets done, but most people are only scratching the surface of what’s possible.

In this episode of Mind the Machine, we sit down with Jay Hack, Head of AI at ClickUp and co-founder of Codegen, to explore how AI is changing productivity, software, and the future of work. Jay shares his journey from studying AI at Stanford to building startups and eventually leading AI strategy at one of the fastest growing work platforms in the world.

We discuss common myths about AI, why hallucinations shouldn’t stop you from using it, and why learning AI today may be as important as learning to use the internet in the 1990s.

If you’re curious about where AI is headed and how it will reshape the way humans work alongside intelligent systems, this conversation offers a thoughtful and optimistic perspective.

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Website: https://findgood.tech/
LinkedIn: https://www.linkedin.com/company/findgood-tech/

Timestamps

00:00 Introduction and why AI will shape everything we do
00:18 Meet Jay Hack, Head of AI at ClickUp
01:06 Jay’s background and early interest in AI
03:30 Learning AI as a student and early machine learning work
05:40 What AI looked like before ChatGPT
07:00 The biggest myths people believe about AI
08:30 Why AI hallucinations shouldn’t stop you from using it
12:30 Why AI will transform industries like medicine and law
15:30 What it means to build an AI-native company
18:20 The rise of AI agents and productivity tools
22:00 How ClickUp is integrating AI into work
26:00 AI tools people should explore beyond ChatGPT
29:40 Why the future of work will involve humans collaborating with AI
33:00 “A nation of geniuses in a data center” and what that means
36:00 Final thoughts on learning AI today

Artificial intelligence feels overwhelming for a lot of people right now. The speed is fast, the tools are endless, and the noise can make it hard to know what actually matters.In this keynote-style talk, Cheryl Goodman reframes AI through a different lens: not hype, not fear, and not magic, but understanding. By grounding AI in history, fundamentals, and purpose, this session focuses on how real people and organizations can think clearly, act responsibly, and move forward with confidence.You’ll learn why AI is a general-purpose technology, how to think about risk and cost, what hallucinations really are, and why understanding matters more than speed. Most importantly, this talk centers on the idea that hope in AI is not wishful thinking, but a valid expectation when knowledge replaces fear.This a framework for leading and building in the age of AI.AI Fluent Course: https://findgood.tech/ai-fluent-in-person-course/Book Cheryl to speak at your company or community, she’s trained executives at Fortune 100 companies and has taught practical AI courses at 7 universities and has led a series of Hack-a thons for all levels of learners. You can submit a booking inquiry through FindGood.tech speaking contact page to discuss keynotes, panels, or corporate events. https://findgood.tech/speaking/AAE Speakers Bureau: You can check her availability and request fee information through All American Entertainment (AAE). They handle logistics, offer negotiations, and contractual assistance.Direct Contact: For general inquiries, her team can be reached at [email protected] or via her LinkedIn profile. https://www.linkedin.com/in/ckgoodman00:00 Introduction – What This AI Talk Promises01:23 The “Three Theories” Behind AI03:17 The Hope in AI Framework04:54 What We’ll Cover Today06:20 Where Do You Stand on AI?08:11 The Generative AI Explosion09:41 Why AI Is Not Just Hype12:19 Why Speed Isn’t the Goal14:18 What AI Actually Is15:26 Tokens – The True Cost of AI17:18 Core Concepts: Vectors, Embeddings, Weights18:19 Everything Is Numbers – How Prediction Works22:42 Temperature – Creativity vs Predictability24:10 Context, Meaning & Word Embeddings26:13 Weights & Bias – Why Training Matters31:56 Hallucinations & Error Rates33:32 AI as a Partner (Not a Replacement)35:12 What AI Can Already Do36:05 Prompt Engineering Explained38:42 Jobs, Infrastructure & Investment Implications39:10 The Hope Framework Recap40:48 Final Takeaways

If your marketing isn’t compliant, the risk isn’t theoretical. It can mean lawsuits, fines, or having your ad accounts shut down overnight.

In this episode of the Mind the Machine Podcast, we sit down with the co-founders of Loopholes, an AI-powered marketing compliance platform built to catch risk before it becomes expensive. They explain how a single word or image can trigger massive penalties, why highly regulated industries struggle to scale marketing safely, and how AI can act like an antivirus for your brand’s messaging.

We cover how Loopholes emerged from years running a regulated marketing agency, what Techstars helped unlock for their growth, and why compliance is becoming a core part of modern go-to-market teams. This conversation is essential for marketers, founders, legal teams, and anyone using AI to scale content in a regulated world.

Get a free trial: https://www.loopholes.com

Timestamps:
00:00 Why non-compliant marketing is dangerous
02:00 The real problem with marketing compliance
03:36 A full AI platform
07:12 Why compliance slows companies down
09:34 How one word can trigger massive fines
11:25 Who actually needs marketing compliance
14:02 The future of AI compliance agents
18:35 Cutting weeks of review down to seconds
25:20 Why GPT alone isn’t enough
30:28 Staying creative without getting fined

Doug Harrison breaks down the 10 mind traps he’s seen repeatedly while working with over a thousand brands and businesses. These traps are subtle, common patterns that work against people’s best interests without them realizing it: the Over-Explainer, the Copycat, the Day Jobber, the Tactician, the Pillar Pitcher, the Glorifier, the Defender, the Interrogator, and the Schmoozer. Doug explains why they happen, how they create risk in the buyer’s mind, and why clarity is the real advantage.Then the conversation shifts into Doug’s next chapter: the Keep Rising platform, built to solve what happens between appointments for advisors like therapists, coaches, case managers, and clinicians. The platform focuses on behavior change through systems instead of willpower, using “extreme humanness,” specificity, and a whole-brain approach to help people follow through on the habits they want to build.Get the book: https://www.amazon.com/Rise-Framework-Business-Distinctly-Matter/dp/1631959514Follow Mind the Machine:Instagram: https://www.instagram.com/mindthemachinepodcastTikTok: https://www.tiktok.com/@mindthemachinepodcastWebsite: https://findgood.tech/LinkedIn: https://www.linkedin.com/company/findgood-tech/0:00 Intro0:30 Episode overview and guest intro1:07 Setting up the mind traps concept1:57 Overexplainer3:09 Copycat4:00 Day Job5:42 Tactician8:02 Pillar Picture21:41 Glorifier26:24 Defender27:07 Interrogator28:18 Schmoozer29:36 Reflecting on all mind traps32:36 Transition to the Rise / Keep Rising framework37:50 Whole-brain approach to behavior change45:21 Why good intentions fail52:57 Closing remarks