#143 Behind the Grind: Halloween Edition...With Chat...GPT!

Welcoming you (and myself) back with what I feel is a dynamically fun edition.

This is our 5th Behind The Grind Interview Edition. The first four featured guys I actually know in real life, and while they came at it from very different perspectives - finance professional, restaurateur, startup co-founder, and deli owner - I feel like we needed to mix it up a bit.

I mean, I can’t just keep interviewing dudes I know personally. So in the spirit of Halloween, this week’s interviewee isn’t even a person!

No, I didn’t find a werewolf or gremlin to interview, and I’m no medium so I can’t talk to ghosts…

…but there is this bot I chat with every day, and it was kind enough to help a brother just returning from his honeymoon out.

I hope you enjoy this edition as much as I enjoyed curating it for you 🤝 

• Behind The Grind: Q&A with ChatGPT💰️ 📈 🚀 
   

• Food For Thought: Reacting to the Interview 📈 🚀

BEHIND THE GRIND 🎙️ 

Interview Case Study With Everyone’s Favorite Bot, ChatGPT! 

Note: You’ll notice the questions are different from BTG Editions past. Obviously I can’t ask why Chat’s chosen its career path or about its favorite piece of networking advice. So I thought long and hard about what would be most helpful to all of you and wrote new questions while maintaining OTF’s three pillars: elevating your brand, fattening your wallet, and boosting your productivity.

LET’S ELEVATE THAT BRAND 📈 

DAN: You might say that today’s attention economy rewards visibility over ability. How can someone use that to their advantage without feeling fake or trying to be an (cringe) influencer?

CHAT:

• In the “attention economy,” human attention is a commodity. Companies and clients seek “known quantities” — people they’ve seen, heard, felt familiarity with.

• Ability alone often sits invisible unless packaged, communicated, and found. Visibility is the distribution mechanism.

• Trust and familiarity accelerate decision-making. If someone has seen your ideas, your voice, your stance, they’re more likely to hire you, buy from you, introduce you.

How you use it without feeling fake:

• Show process, not just polished outcome. Transparency builds authenticity.

• Choose a niche you genuinely care about — building visibility around something you don’t believe in creates dissonance.

• Be consistent and useful: Focus on helping your audience solve real problems; visibility is the by-product of value.

• Use “low-stakes visibility” early: comments, short posts, stories of learning. You don’t need perfect; you need to be active and present online.

Benefit: You gain leverage: your brand becomes the engine that magnifies your ability. You attract opportunities instead of chasing them blindly. You shift from “I’ll wait until I’m perfect” to “I’ll show up, create value, build trust, and reap the rewards of visibility + ability.”

DAN: If someone said, “I want to take advantage of the modern economy but I don’t know where to start,” what’s the 12-month blueprint from zero brand to first dollar?

CHAT: Treat your brand like a startup.

• Months 1–3: Clarify your niche (skills × market need) and build a simple online presence — one platform, one message.

• Months 4–6: Publish weekly insights or examples of your work and engage with others in your niche.

• Months 7–9: Collect proof — case studies, testimonials, or small wins — and offer a free resource to build trust.

• Months 10–12: Launch a low-ticket product or service, refine it, and repeat what works.

Benefit: You’ll build visibility, authority, and your first monetizable offer — turning brand into trust into income.

DAN: How can someone use both verbal and online communication to build authentic, high-value relationships that compound into opportunities and income?

CHAT: The strongest communicators blend clarity, curiosity, and consistency.

• Be specific. Don’t say what you do — say who you help and how you create value. Specificity makes you referable.

Example: Instead of “I work in finance,” say, “I help young professionals build systems to manage money smarter.”

• Be consistent. Use the same tone and message online as offline. Consistency builds credibility.

Example: If your offline voice is fun, thoughtful and practical, stay that way in DMs or meetings.

• Be curious. Ask better questions and listen twice as much as you talk. Curiosity signals confidence and increases connection quality.

Example: Swap “What do you do?” for “What project are you most excited about this year?”

Benefit: Each habit builds relationship capital that converts into real leverage — referrals, collaborations, and income streams that start finding you, not the other way around.

LET’S FATTEN THAT WALLET 💰️ 

DAN: Why does it feel like this latest generation of young professional is working harder than ever without seeing the same rewards as previous generations, and how can they start actually building wealth in the modern economy instead of just earning and spending it?

CHAT: Because the rules have changed but our playbooks haven’t.

Inflation, societal comparison, and rising costs make saving feel like a big mountain to climb, but most people stay stuck because they only trade time for money, instead of building systems that earn while they sleep.

Here’s how to start fattening your wallet in three stages:

1. Automate stability. Auto-transfer money into a high-yield savings or index fund — consistency beats timing.

Example: A recurring $200 weekly deposit into a 5% High-Yield Savings account or Index Fund quietly compounds over time.

2. Increase your skill yield. Your best investment is learning a money-making skill — create content, use AI, etc.

Example: LinkedIn Learning found professionals who added one high-value skill earned 25% more within 12 months.

3. Create leverage. Build something that scales beyond your hours like a digital product, template, or small side brand.

Example: Making and then selling one $50 product a week = $2,600/year — proof you can earn without extra hours.

Benefit: Automate, upskill, and leverage — and money becomes a friend. You’re no longer waiting for raises; you’re giving yourself one through your own skills.

DAN: What’s the most overlooked way to make more money today?

CHAT: Leverage what you already know. Teach it, write about it, or turn it into a digital resource.

Benefit: You turn your experience into equity — monetizing skills you already have instead of chasing new ones.

DAN: How can someone build stability and take advantage of new opportunities in this…err, unpredictable economy?

CHAT: Split your focus 80/20 — 80% defense (savings, essentials, emergency fund), 20% offense (new skills or side projects).

Benefit: You stay safe while still playing offense — the sweet spot where real opportunity lives.

LET’S BOOST THAT PRODUCTIVITY🚀 

DAN: Productivity sounds great, but it’s not all created equal. How can someone actually use it to make more money?

CHAT: Productivity is profit disguised as time. Use it to free up capacity — then reinvest that time into higher-value work or a side project.

Example: If you save 5 hours a week with automation and use it to learn a skill or build an online asset, you’re compounding time into money.

Benefit: You stop trading hours for income and start multiplying both.

DAN: I would consider being healthy productive. I know “health” isn’t something that you have to worry about, but how does a human’s taking care of their health impact their wallet?

CHAT: Health is a productivity multiplier. More energy = better decisions, faster output, and fewer sick days.

Benefit: A stronger body literally compounds into stronger earnings.

DAN: What’s a simple productivity rule for someone trying to create more financial opportunities this year?

CHAT: Protect your morning and put yourself first. Do one thing that moves you forward before the world wakes up — learning, writing, etc.

Example: Spend 30 minutes on your side idea before checking your phone.

Benefit: You start every day building your future, not just your employer’s.

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FOOD FOR THOUGHT 💭 

I’d like to thank ChatGPT for its time and eff— nah, never mind. Here are my quick takeaways instead:

1. So much of what the bot said are in line with my personal experiences, opinions, and perspective. In fact, I’ve written about a lot of this stuff in past editions. Maybe I do talk to this thing too much 👀 

2. I’ve worked at the same company for ten years now, and yet I don’t own any of what I’ve produced (please let that sink in). Taking on the risk of a side project - OTF! - has been amazing because it’s given me ownership of something in a niche I genuinely care about, it’s forced me to up-skill in very real ways, and hopefully one day it will reap the rewards of an attention economy.

3. This is also why I’ve tried to build my personal brand online through platforms like LinkedIn and TikTok. Ability is great, but no one will ever know about your abilities without visibility.

4. I’ve embraced AI, perhaps more than the average person, because unlike the bots, we humans are not built to always work; we’re built to connect with one another and dedicate ourselves to meaningful projects, whatever those may be. AI tools like ChatGPT are the means to that future.

Before You Go

I really hope you enjoyed this edition, and I’m happy to be back with all of you! Wedding / honeymoon season was incredible, but the (only) bright side of it being over is I get to throw myself back into OTF. Thank you, as always, for your support, especially over this last month or so. It means the world to me.

Next week, we’ll be back with November’s GROWTH EDITION 📈 , featuring The Search Bar, an all-new 2 Do List, and the top favorite of mine, Say It Better with Prof Mike!

Have a safe and happy Halloween, and as always, see you next Tuesday 🤝 

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