What's it like to work at I Will Teach You To Be Rich

Written on February 20, 2022

When people ask where I work and I share with them that I work for a company that is called, I Will Teach You To Be Rich (IWT), I usually get a raised eyebrow as a response.

My wife did when I told her I was interviewing with IWT.

Healthcare staff do every time they see my insurance card and notice the name of my employer.

Friends do every time I share about something cool we’re doing at work.

And I get it—it’s an unconventional business name that also sounds kind of scammy.

But after working at I Will Teach You To Be Rich for more than two years, I thought I’d share my personal experience with working at the company.

At the time of this writing, I run the IT department at IWT as their senior IT lead. I came into this role having been a software developer for almost 10 years. I share this because it’ll paint some of the experiences I’ve had at IWT.

Challenged by core values

I Will Teach You To Be Rich has five company core values.

Those are:

  • We’re constant learners
  • We communicate with intent
  • We practice extreme ownership
  • We’re better as a team
  • We focus on what’s possible

While most companies have core values, it’s very rare they actually live it and allow those values to direct outcomes of your work.

At IWT, we all know our core values and we challenge each other to practice those values in our work.

As someone who’s in a management role, I feel the need to always pull my own weight. But this often backfires. Why? Because, I’m not always the best person for the task at hand.

When I get busy, my default is to become focused and work on solving the issue at hand. Which is what happened for a project I was once managing. I knew we had some hard deadlines and the large amount of work that needed to get done in order to finish.

No one told me to work long hours, but I convinced myself that that’s what it would take in order to succeed. When my coworker realized the amount of effort I was putting in, she challenged me to step back and assess if it was the most efficient way because I was on a clear path to burning out.

Together we came to the conclusion that there were teammates better skilled for some of the tasks I had on my plate and that I should ask for their help.

When I finally asked my coworker for their assistance, it was not only met with enthusiasm, but the solution that they came up with in order to finish the task I was delegating to them was far better than anything I could have come up with by myself.

I learned quickly at that moment what it looked like when we worked better as a team.

Many companies have been forced to become remote due to the pandemic. I Will Teach You To Be Rich has been remote since day one. I have colleagues in every time zone in the US. I even have a colleague who is a nomad—living and working out of his RV.

Being a remote company takes a mind shift and I believe IWT has had the right mind set about being a remote company from day one.

I believe this is possible because of their value—communicate with intent.

So you want to hold a meeting? Great! Invite who you need to the meeting, but you better be sure to have an agenda sent ahead of time.

While we do have water cooler type Zoom calls to catch up, all other meetings must have a purpose and must be clear on what you want out of that meeting.

Everyone at IWT value deep work. As such, we’re also encouraged to block out our daily schedule with deep work sessions so that we won’t be disrupted with meetings. Heck we even have a company-wide, no meeting day on Wednesdays.

This team knows its values and it shows in our day-to-day work and interactions.

Super awesome colleagues that will level you up

All of my coworkers at IWT are super smart. Way smarter than me.

One of the things that I’m sure of with working with such a talented group of people is that I’ve leveled up both personally and professionally.

We use Slack at IWT to communicate as a team. One of the channels is called “better”. In this channel we share about articles or recent learnings that has personally improved the way we work, think or live.

In the channel, I’ve learned how coworkers utilize Tiago Forte’s PARA method to organize work and life projects.

I also get book recommendations like Cal Newport’s Deep Work or Four Thousand Weeks by Oliver Burkeman. Both of which has impacted the way I think and live.

We also have a channel dedicated as our digital water cooler. Not only do you get a healthy dose of the best gifs that the Internet has to offer. But I also get glimpses of how my colleagues are living their rich life.

The rich life is one of our principles of living your ideal life.

For me, I’ve shared that being able to work for a remote company has allowed me to be a better father since I was able to walk my kids to school daily from home which is part of my rich life.

Countless stories of how my coworkers are living their rich life has shown me two things. One, it’s that we not only talk about what it’s like to finding a rich life at IWT but two, we challenge each other to continue to refine and live our personal rich lives.

Your work makes an impact

As someone who has had a career as a software developer, one of the challenges I’ve faced is being too far removed from the feedback loops of what I produced and how it solved a business or a customer problem.

At IWT this isn’t the case.

Our readers and students are literally everywhere on the Internet.

Ever see a person tweet about needing advice on personal finance? It’s likely Ramit Sethi’s book, I Will Teach You To Be Rich, will come up as a recommendation.

As a company we identify as a business that’s in the online education and self-development industry. I’ve come to realize, we’re in the business of changing lives.

I mean really.

Ramit’s book, I Will Teach You To Be Rich, is one of the best personal finance books I’ve ever read. Chock full of actionable steps that has lead to so many people changing their financial trajectory for the better and not by cutting back on lattes.

Our flagship products, Earnable and Dream Job teach you how to start your own business or find your dream job. But not just by telling you how, but showing you. Along the way giving students glimpses of what sort of rich life it could unlock, should they achieve their goals.

Just have a look at our success stories page and you’ll see that these are real people, who have been impacted by the work we’ve done and how it has changed their lives for the better.

We’re also self-funded and a private company. Which means, the company is always aligned in serving its customers—the readers and students.

You’ll think differently

My colleagues at IWT challenge me to think differently about how to work.

I once sat in a meeting with some teammates when we were trying to decide on a vendor to go with for a project we were working on.

We listed each company with their pros and cons and ranked them based on their bid for the project. Conventional wisdom might tell you to go with the company that came in second place since they aren’t the cheapest and they aren’t the most expensive.

But Ramit made us pause and then asked something along the lines of, “aside from the sticker shock of the most expensive option, what other value would you get by going with them?”.

We responded with higher quality of work, less vendor management, less churn and less stress.

Once we acknowledged those points of value, the choice became clear. We were only looking at the basic inputs and outputs. But Ramit challenged us to look at the bigger picture and the added value we would be getting by going with the most expensive option.

What?! You had direct access to the CEO of the company? Yup! I was in the same (virtual) room as my coworker, Ramit Sethi. Ramit is a very cool and approachable guy.

Coming from multiple start ups in my career; speed and velocity isn’t uncommon for me. But one thing that I’ve learned at IWT that I haven’t ever seen in my career is slowing down, to go fast.

Speed can come in two forms—haste and fast. When you’re moving in haste, you aren’t making the best decisions and you’re rushing to get to your destination. When you’re moving fast, you’re in control of the speed. Decelerating when you need to and speeding up when it’s safe.

There have been times projects I’ve worked on at IWT will intentionally be slowed down because we might’ve missed something. By slowing down, we can course correct on where we’re going and then once finding our bearing, speeding up to make sure we hit our mark—fast.

Great benefits

If you’ve reached this far in the article, you might have caught on that I had anticipated that you as a reader probably found this article because you’re wondering what it might look like to actually work at I Will Teach To You To Be Rich.

I’m hoping that this article has provided some insights on what it’s like actually working at IWT. If you’ve got any questions, please feel free to reach out on Twitter or LinkedIn and I’m more than happy to share my experience.

By now you should know that IWT is a legit company, with super smart people and with work that’s making an impact in peoples’ lives.

As a husband and father, I don’t make career moves unless it provides a certain level of financial security for my family.

As such I thought I’d share the benefits working at IWT has afforded me and my family. The benefits I’ve enjoyed at IWT has rivaled some of the bigger technology companies I’ve worked for.

Our compensation is competitive. Don’t believe me? Well, use our material, show us that you’re a top performer once you apply and then negotiate your salary if you get an offer.

IWT covers the majority of your medical benefits for the employee and family.

A generous company matched, 401K plan.

In addition to the basic benefits mentioned above, you also get access to services like Headspace and Ginger to help with mental health and meditation.

Finally, you get a $100 per month allowance to put towards technology. Be it your Internet or online service. But really it’s an allowance that can be used for whatever you need. I’ve used it to buy books that I was interested in.

Oh, I almost forgot! You also get access to all the courses that IWT offers absolutely for free. I may be biased, but these courses are super top notch. The bar for the quality of these videos is high and it’s packed with so much value. Thousands of dollars of education is free to you for just working at IWT.

Join IWT

I Will Teach You To Be Rich doesn’t hire often, but if it does have an opening and the team sounds like a good match for you, apply!

It’s a great place to work, where you’ll be making an impact in peoples’ lives and you’ll grow—professionally and personally.

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