I Will Teach You To Be Rich

Making more money doesn’t automatically make you feel better about money. In this video, I break down the 7 habits that help people spend confidently, automate their finances, and stop stressing about money every day.

5 days ago | [YT] | 11

I Will Teach You To Be Rich

“I thought I’d win it back.” That’s how it starts. Today I’m reacting to real gambling stories and breaking down the mindset that pulls people deeper—even when they think they’re being smart. The same thinking shows up in investing, crypto, and everyday money decisions.

1 week ago | [YT] | 20

I Will Teach You To Be Rich

Why would I spend MORE to own a WORSE place in a WORSE neighborhood, that requires me going to the WORST place on Earth, Home Depot, every Saturday?!

Before buying, it’s important that you ask yourself some questions:
– Is it a better financial decision to buy or to rent and invest the difference?
– If I buy, can I comfortably afford it?
– Are payments on this house less than 28% of my gross income, maybe even 32% or 34% in expensive cities?
– Do I want to buy a house? Why?

When we don’t ask these questions, we just go, “Oh, that’s what everybody does. So I’ve got to do it, too.”

That’s the wrong way to go about making the biggest purchase of your life.

Read the rest of the article: www.cnbc.com/2026/06/28/some-renters-say-homeowner…

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2 weeks ago | [YT] | 335

I Will Teach You To Be Rich

People spend hours researching investments while ignoring the skills that have the biggest impact on their income. In this video, I break down the 8 skills that helped me earn more money, negotiate better, and create opportunities that no stock portfolio could match.

2 weeks ago | [YT] | 47

I Will Teach You To Be Rich

What if spending an extra $50 could completely change how your week feels? In this video, I break down the different levels of convenience and show how small purchases like grocery delivery, cleaning services, and other simple upgrades can help you buy back your time and enjoy your life more.

3 weeks ago | [YT] | 40

I Will Teach You To Be Rich

Weddings are full of emotional spending decisions. In this video, I react to real wedding spending stories and break down how couples can spend intentionally, avoid common mistakes, and feel good about the choices they make.

3 weeks ago | [YT] | 9

I Will Teach You To Be Rich

TOMORROW! 🎟️ www.iwillteachyoutoberich.com/mcrs-event-registrat…
Chris Hutchins, points expert and host of the popular podcast, All The Hacks, is ready to share his tricks for using points you already have to book the vacation of your dreams.

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4 weeks ago | [YT] | 76

I Will Teach You To Be Rich

You're trying to plan summer travel.

The flights are $1,200. The hotel is somehow $487/night. You open your credit card rewards app, see a point price that looks reasonable, and think, "I guess this is better than paying cash."

But imagine if that same stack of points could get you 3x – 5x more value. That's what Chris Hutchins, points expert and host of the popular podcast, All The Hacks, is going to show you.

Chris has booked over 15 million points worth of travel, and he knows the moves most people never learn:
→ when to use credit card rewards
→ when to transfer points
→ which tools to search
→ how to avoid wasting points on mediocre redemptions

The good news? You don’t have to become a full-time points nerd in order to travel better this summer.

In this live session, Chris will show how to turn the points you already have into better flights, better hotels, and smarter summer trips. He'll walk through real examples, taking audience point balances and showing what they could actually be worth.

Bring your card, your balance, and the trip you're considering.

Join us:
📅 Tuesday, June 16, 2026
⏰ 12:00 PM ET / 9:00 AM PT

The event is completely free. Before you book your summer trip, see what your points are really worth.

Reserve your spot 🎟️ www.iwillteachyoutoberich.com/mcrs-event-registrat…

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1 month ago | [YT] | 99

I Will Teach You To Be Rich

In this video, I break down five money lies you’ve been hearing your whole life from politicians—lies that are costing you thousands of dollars. The real problem isn’t your discipline. It’s the rules you’ve been following.

1 month ago | [YT] | 56

I Will Teach You To Be Rich

My wife and I took a 3.5-month sabbatical this year!

It was life changing. We went to:
- Barcelona
- Paris
- Marrakech
- Japan (lived there for 2 months)

We set up our businesses to run without us so we could focus on each other and our experience. Every day we'd wake up and decide what we wanted to experience every day.

One day, I wanted to visit an umbrella shop that's been making umbrellas by hand for 100 years. Another day, we went to an art class.

We love design & architecture, so we set up private tours in Morocco & Kyoto to explore craftsmanship, textiles, and interior design.

We're not really into fine dining so we skipped eating at super-nice restaurants and found our favorite bakeries & yakitori spots.

We had some custom art made from local artisans.

And since I'm a hotel guy, I chose some of the world's most inspiring hotels to stay at. I usually take the manager out for a walk around the property and ask them about their business, clientele, and the hotel itself.

It was truly life changing.

I gave a presentation covering the details of our sabbatical:
- How we planned it
- Where we stayed
- What we splurged on & what we didn't really care about spending $ on
- How we stayed in shape
- What we spent our time doing

You can see the replay in my Money Coaching program: iwt.com/moneycoaching-ct

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1 month ago | [YT] | 3,194