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Innovating with AI

"It's a big investment. I want to make sure it's worth it" - Me

Published 4 months ago • 6 min read

Hey Reader,

Story time: Over my 20-year tech career, I have generally made one or two big investments in professional development each year. In fact, I vividly remember thinking about spending $1,000+ on a program to help me grow my business.

I was a web developer with some early success under my belt in 2009:

  • I was making around $5,000 per month.
  • Living with my then-girlfriend, now-wife, in a 1-bedroom apartment.
  • Reading books on personal and professional development, trying to "get to the next level."

I didn’t have many friends who were also freelancers who I could connect with, and definitely didn’t have a mentor I could learn from directly.

That's when Ramit Sethi, a NYT bestselling personal finance author, launched his first online course.

Nowadays, some people know Ramit from his Top 10 Netflix show that came out last year that got 33,900,000 hours of watch time in 6 months, beating out ~2,000 shows including several Hollywood blockbuster movies.

Back then though, Ramit didn't have a 10+ year track record, a hit Netflix show, 1M+ book buyers, and 100,000+ people who bought his online courses.

So when he launched his first online course called "Earn $1,000 on the side" (Earn1K for short), I was skeptical for a few reasons.

1 – His book was on personal finance, not business.
2 – I'd already made more than $1,000 on the side.

I paid close attention while he was revving up to his first launch because it was almost perfect for me.

It taught you how to grow a freelance business (exactly what I was doing as a web developer) and seemed like it was packed full of serious, actionable advice, strategies, tactics and templates.

I researched it for several weeks…but when the course opened, I didn’t buy it.

Why? Money (or so I thought).

The main reason I told myself was that I just hadn’t ever spent anything close to that amount of money on one learning experience before.

And the main objection I latched onto was the fact that I was already earning more than $1,000 a month on my business (I was in the 5k/mo range) and I was already working full-time, so the money wouldn’t really be “on the side.”

I didn’t take action, but I did stay on Ramit’s newsletter so I could keep learning from him.

Fast forward: About six months later, he opened the Earn1K course again. This time, I had six months to look back – business was okay – I was still making around 5k/mo, but I didn't have any real breakthroughs to show for it.

A – I’d read some more books and they’d helped a bit with how I thought and felt, but I hadn't translated them into having a measurable business impact.

B – My then girlfriend, now-wife, was still leaving every morning to work in a bustling downtown office. Then, I'd still be tap, tap, tapping away at my laptop from the kitchen table of our 1-bedroom apartment. Alone.

C – I didn’t have many friends who were also freelancers who I could connect with, and definitely didn’t have a mentor I could learn from directly.

So even though I was already a little ahead of the title of the program (Earn $1k On The Side), I decided to take a fresh look. At the very least, meeting fellow students and having direct mentorship from Ramit and his team was worth a try.

So I shelled out $1,000 and joined the second time around.

And oho, let. me. tell. you. SOMETHING.

Remember how I thought I was too advanced for the Earn1K program?

Boy, was I wrong.

In just a few months of implementing everything I learned, I'd scaled my freelance business up to $10,000 a month, officially eclipsing my friends’ full-time salaries at traditional jobs.

Even though Ramit framed it as a starter course, the strategies were just as applicable for me at the next level of business growth.

Then, I joined another program he launched, and paid $4,000 in full for it.

That investment took me from $10,000 to $20,000 a month the next year.

But, it didn't stop there.

Fast forward quite a few years and HDC, my tech firm, generates millions in revenue with a lean-and-efficient team of employees I'm proud to call my colleagues.

And, I attribute 90% of my success to what I learned from Ramit.

$5,000 investment.
$1M+/year results.

The wins weren't just from the curriculum though.

They continue to get multiplied by the community of people who also went through the curriculum…even after 13 years.

I got one referral from a friend in the program last year that paid me $24,106.50. And this year I redid the website for another friend from the program, who has paid $27,388 since we started and is still going. The community alone has already paid out way over 40x my investment.

Building a $1M+/year business wasn't the biggest win

The financial results of investing in myself have given me quite the insane ROI. For that reason, I never bothered with the bite-sized $10 courses.

One of the biggest wins for me is how investing in these programs has shaped me as a teacher and mentor as I advance in my career.

Personally, I've never heard of students who took a $10-Udemy-course or 3-minute YouTube tutorial video going on to create advanced success for themselves and others.

Heck, I've never heard of the creators of those courses developing real relationships with their students either.

I know just how impactful having the right curriculum, coaching, and community has been on my life.

And it's a big part of why I've invested over $100,000 and 12+ months to develop the IWAI Incubator.

Personally, I get a lot of fulfillment from being able to create and continuously upgrade a program that has the best of everything I've experienced in my own journey, to give you the greatest advantage in your own learning and professional development journey.

Is IWAI a significant investment?

Absolutely.

Is it at a level of investment that maybe you, like I did, might pause for 6 months before deciding to try it (with our risk-free guarantee)?

Definitely.

Am I in there rooting for you to win at every step of the way?

Yes – I'm on live calls with every student who joins The Incubator.

With all of this, are there still reasons to be skeptical?

Actually, YES – just look at the words of fellow IWAI readers like you:

Erich: “These days, evaluating any professional development program requires careful consideration. Anything that takes time and money away from other things needs to provide a ton of value.”

Karl: “What was the biggest obstacle or hesitation? I'd say the price. I think it's fair, but it's still a lot of money.”

Matt: “Obviously you can spend a lot of money and a lot of time on something like this.”

Keanan: “I think for me the biggest hesitation that I had was it seemed like all of the information that I needed to learn about AI was available for free online.”

When I read their words, I think back to my own words many years ago.

They are discerning, just like I was.

And now, every one of them are now featured students on our results page – each a graduate of our IWAI Incubator, describing on video how they launched their own AI products and processes.

In the age of AI though, there's even more reason to remain skeptical, and so I've gone one step further.

I started working with Trustpilot to collect verified, independent reviews from our students in one place.

My favorite thing about Trustpilot is they take no prisoners about fake or sketchy reviews. Unlike Udemy, Coursera and YouTube, they have no stake in my revenue so all they care about is the truth (rather than likes / views / commissions).

They are so harsh that every new company starts at 3.5 stars and has to work their way up to a higher rating.

In other words, there is no B.S. 5-star rating available on Trustpilot. Right now, we have six 5-star student reviews and because of how seriously Trustpilot takes their ratings, our “overall” rating is still “4.2 Great” instead of “5.0 Perfect.” It’s mathematically impossible to get a 5.0 and I like it that way.

I know.
This email has gone on for quite a bit.

But I'm doing all of this because The Incubator opens this week, and I don’t want it to be a last-minute decision for you.

If you're discerning, like I was, I'd prefer you to have everything you need to make an investment in yourself that you're proud of.

That way, when the time is right, there's nothing to deliberate – you'll be first in line to strike while the iron is hot – because the faster you enroll, the more time you have to do the work and win.

So, I write to remove every logical reason you have that’d get in the way of that.

I also shared my professional development story to remind you of something you already know:

You never lose when you invest in yourself.

This year is yours, but only if you choose for it to be that way.

– Rob

P.S. There's nothing to buy in this email. I wrote it to help prepare you to win. Tomorrow, we'll go deeper on what it takes to do that through examples of those who have already done it. You’ll hear more from the discerning students I mentioned today. If you want to get a head start though, you can start watching their student video reviews here.

Innovating with AI

Rob Howard

We help entrepreneurs and executives harness the power of AI.

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