Last updated on November 3rd, 2021 at 07:43 am

5 years ago, I was waiting tables at a Thai restaurant (thanks for the reminder, Facebook).

To be honest, it was a low-point: I lost 20lbs on my diet of peanut butter sandwiches for lunch and wonton soup for dinner. I made $35 in tips during my shifts. Everything in my life felt like… you remember that B-movie with Matthew McConaughey and Sarah Jessica Parker, Failure to Launch? Basically, that.

In an act of desperation and tapping into my savings, I bought an online course from this blogger named Ramit Sethi. It was called Find Your Dream Job, and to say it was a game changer doesn’t do the course justice.

I quit my job waiting tables, focused on working for free and learning how to create value for others. Yes, I also landed my dream job. One thing led to another, and years later, I found myself working for Ramit at his company, I Will Teach You to be Rich (IWT).

For the last 3 years, I worked with the smartest, hardest working team I’ve ever had the privilege to work with. Every day, I worked on decoding human behavior and creating amazing courses. I thought an appropriate goodbye to the IWT team and community would be sharing my 8 favorite lessons learned there.

1. Write it up

Have an idea that could improve the product? Read a book you think could 2x revenue? Take notes and write it up.

Knowledge stuck in your head helps one person. But when you take action, “write it up” and share with your team, you scale knowledge.

For example, when Ramit came back from vacation, he passed around the 4 pages of notes he wrote about his hotel, and all the different things they did to make his holiday a magical experience.

“How” you share doesn’t matter. Put the lessons into a blog post. Post on Facebook. Or just create a Google doc. As long as you’re getting that knowledge out of your head and into the world.

2. Be professional

I’ve never seen another company prepare for meetings the way we do at IWT.

“Professionalism” isn’t just about showing up on time, or wearing the appropriate footwear for the meeting. Being on time is a commodity. It’s table stakes — it’s expected and impresses no one.

At 95% of IWT meetings, there’s an agenda, with detailed bullet points on what we need to cover. Everyone reads it before we meet, so no time is wasted “setting the table,” so to speak. We get right into the meat.

You’re going to get called on, so be ready to contribute your ideas.  No checking your Instagram feed while you’re on a call. Come prepared. And after most meetings, I come away with more notes on how to be a better thinker, leader, and product developer.

3. Serve steak but sell sizzle

The first program I was hired to create was supposed to help shy people with their social skills. I remember my first draft of the “system” I recommended: It was some crazy Venn diagram with dyslexic arrows pointing every which way. It looked like a flowchart drawn by Salvador Dali.

I called it a “social fluency system”… and thank goodness wiser minds prevailed.

Eventually, we named that program How to Talk to Anybody, and the “social fluency system” died a quiet death.

That was my crash course on the timeless lesson:

You don’t sell features (250 Horsepower; works your trapezius and rear deltoid; includes 8, 30-minute HD videos).

You sell benefits (drive fast, impress women, land a new job with these skills).

In other words, the steak (the features) has to be good — great even — but you sell the sizzle (the benefits).

The first 50 times or so I heard this advice, I saw it as a sales tactic. “Oh, it’s just the best way to get more people into the top of your funnel.”

In the past 6 months it finally dawned on me that “sell benefits, not features” is the tip of the spear to change any behavior.

Before you can convince anyone to change — whether it’s to live healthier, save more money, or improve their social skills — first they have to be receptive to the idea. If they’re never receptive to the idea, it doesn’t matter how good your program or system is.

Features don’t make people receptive. Benefits do.

4. Working smart isn’t enough

The I Will Teach philosophy is built around the idea of systems: Build smart systems, automate the mundane parts of life, so you can focus on things that matter.

It’s true, but I think a lot of readers — especially those who come from the lifestyle design space — misinterpret the message: That if you just work smart (aka build systems) you don’t have to work hard.

I can see how some people get this impression. And look, if you’re happy, and you just want to cover your nut living in Thailand or Oklahoma or somewhere where the cost of living is quite low, then yes, systems will make work A LOT easier.

But… if you’re not happy with what you got… or you want to impact millions of people’s lives, then working hard isn’t enough.

We use hundreds of systems at IWT. Most of them are automatic. And people here work hard… and Ramit sets this pace. He sets the culture of hard work. This is one of those things you realize the more you work with him… when you see him in his downtime, (when he’s not running his million dollar company) he’s writing emails, articles, and guest posts. While you’re at the gym or eating dinner, he’s posting a new article on Slack you should read, or replying to every single comment in a blog post, or checking in with you to see if there’s anything you need…

You see this behavior and it makes you rethink the time you wasted during a YouTube death spiral and the 30-minute break you took to watch another episode of Masters of None between meetings.

I’m not saying this is the “right” culture. Happiness and productivity experts will give you a hundred reasons why you shouldn’t live your life like this. It’s certainly not for everyone.

But I wanted to dispel the notion that you can achieve this kind of success by just working smart.

5. Do things that don’t scale

Before I started working at I Will Teach, my wife sent Ramit an email. When I got home, she was grinning. “He replied,” she said.

“What’d he say?” I asked.

“‘hahahhaa’”. It made her day.

That one email — an actual real reply — was worth a dozen emails, “personalized” with a snippet of code dropped into the greeting.

In a world of viral loops, ad retargeting, and shopping cart abandonment emails, turns out behaving like an actual human gets a reaction from people — even something as simple as “hah”.

If you follow what I Will Teach talked about, you know systems and automation are the bread and butter. We turned everything into a system: automating your personal finances, using proven email scripts to network, even paying $50,000 a year on a personal trainer, chef, and nutritionist to automate your health.

But if you watched Ramit’s behavior closely, you saw a lot of Ramit’s day was spent doing things that didn’t scale. For example:

• Meeting journalists for coffee 1x per week
• Meeting advanced students 1-on-1 to help with their business (for free)
• Throwing parties so he could help dozens of students connect in person
• Countless hours replying to Tweets, emails, and comments

No fancy automation, outsourcing, or bots doing the above. Just Ramit doing the street-level work it takes to build relationships. Doing things that don’t scale is as much the “secret sauce” for the company’s success as all the systems we have in place.

6. The customer isn’t always right

As Product Developers at I Will Teach, a big part of our job is research calls. We usually have another PD “shadow” our calls on another line, who takes notes. Once, Ramit shadowed mine.

Afterwards, his biggest criticism was, “You’re too polite.”

I’m paraphrasing here, but basically he said:

“People will ramble on these calls if you let them. I know you think the polite thing is to let them ramble. It is polite. It’s also wrong.  

“You do them a disservice by letting them ramble. You think you’re doing them a favor by not cutting them off, but you’re doing them a disservice. You’re wasting their time and yours.

“If you want to best serve the customer, you have to listen, challenge them when you think they’re not telling the whole truth, and get all the answers you can to help them solve their problems.

“So go into the call knowing what you want, get it, then get out.”

7. Find the analogy

Anytime we ran into a difficult concept we wanted to explain simply, the approach was always the same: “Find the analogy.”

How was the concept used in other industries? What are examples outside of the topic we’re talking about?

For example, one of the hardest ideas to explain in Zero to Launch, our course on starting an online business, was positioning. So instead of trying to explain it with examples in online business, we used gyms to explain the concept. For example:

“You probably wouldn’t tell your mom to sign up for a Gold’s Gym or a Crossfit box… but Planet Fitness would probably be perfect for her. Meanwhile, most bodybuilders from Gold’s look down at ‘globo gyms’ like Planet Fitness. Because all these gyms are positioned differently.”

An analogy is the best way to take a concept from the clouds to the street. When it came to social skills, we used fashion analogies. With fitness, we used military metaphors. And with food, we used fitness.

How do you use more analogies? The best way is to become more of a Renaissance person. You have to taste a lot of different things outside of your domain, and be able to draw from all sorts of experiences. Politics, fashion, television, film, fashion, design, tech culture, etc.

If you follow our material, you’ll notice that it’s the ability to draw from all sorts of worlds that make the content so evocative.

8. Be candid

Some of the best advice Ramit gave me was also the simplest: “I need you to get better at writing.” Obviously, he gave more context than that, but the message was simple: Do better.

It hurt to hear that — a lot. But it also laid out a pretty clear path: I needed to spend all my time getting better at writing.

So I started writing more. I joined an internal writing program, where we critiqued our work everyday. I read books on the craft. I studied all of our best pieces, dating back 5 years.

The end result: I wrote about a dozen pieces with Ramit and in 5 weeks, helped complete the first IWT ebook for Amazon called Your Move… which quickly hit a #1 bestseller spot.

None of which would have been possible if Ramit wasn’t candid. Candor isn’t an excuse to be mean or to make it personal. But you have to let people know where they are, where they stand. Anything else is a disservice.   

What’s next

I joined I Will Teach to build their first social skills product in 2014, while we were still a small team. Since then, we’ve tripled in size, I created 2 other programs, hosted events from bowling parties to swanky dinners, wrote a dozen articles and an ebook.

I’m moving onto the next challenge, working full-time as a senior product developer with another company.

But I’m enormously grateful to Ramit Sethi and Jeff Kuo for the opportunity to work at I Will Teach. I recognize you guys took a chance on me. Your candor, mentorship, and friendship have shaped me into a better PD and person.

Working at IWT has been a privilege and is directly responsible for so much of the richness in my life, from living in NYC, putting a priority on my health, and friendships all over the world. I’ll always be grateful, and can’t wait to see what the team does next.

At the end of the day, I remain a student for life. Thank you.