Highlights from my 15-year Stanford reunion

A few weeks ago, Cass and I flew to Stanford for my 15-year college reunion. 

Going to Stanford was transformative for me. It taught me what excellence really is. I met amazing friends. And Stanford gave me the freedom to explore topics like technology and social psychology, persuasion, cults, deception, and ethics.

I shared some of my highlights and takeaways from my trip on Instagram, and now I’d like to share them with you here.

I wanted to give Cass a tour before the reunion, starting with the spot that had the most impact on me during my 5 years at Stanford.

Los Altos Taqueria.
The best Mexican place near Stanford.

Should we move to California?

After tacos, Cass and I headed over to campus, walking through Stanford’s iconic Palm Drive entrance. This “Welcome to Stanford” banner was one of the first things I saw when I visited for the first time, and I’ll never forget it.

Welcome to Stanford

During my first visit, I was really surprised at all the trees along Palm Drive. I thought, “Why don’t they hire someone to do some landscaping?” But it turns out, this is all intentional. 

This is an 8,180-acre campus with foothills, plains, and more than 43,000 trees. There are all kinds of animals, birds, hikes, places to walk.

The Oval

Look at that grass! What does it take to maintain something like this? It’s the same love I feel toward luxury hotels. It’s not just that it’s beautiful, it’s that there’s a team of people looking after you, and they value beauty and care.

We were lucky to be there on a leisurely Wednesday afternoon and take our time exploring the campus. And if we got tired, we could always head back to our hotel and take a nap. No rush. We could rest and come back tomorrow. That’s the beauty of a flexible schedule, even in the middle of the week. 

We headed over to Memorial Church, a beautifully architected, interdenominational church that was built in the late 1800s. Many alums get married there — there’s a years-long waiting list. Cass was blown away, even though there were so many other mind-blowing buildings on campus. She said, “Wow, I’ve never been on a campus with a church.” I loved seeing Stanford through her eyes.

Memorial Church

Cass built SoulCycle’s retail business before starting her own business, Next Level Wardrobe. So I wanted to take her to the Stanford Student Enterprises store, a student-run merch store on campus. I worked at SSE as the marketing manager, one of my first business jobs, and met a lot of friends who went on to start their own businesses. It was great to see it still running 15 years later.


One of the first things I noticed when I came to Stanford was that all the classroom doors were unlocked. You could walk in and explore, use a conference room if you wanted to. There were essentially unlimited resources. 

What a beautiful symbol. It’s hard to get in, but once you do, they trust you. 

I created my business in the same way. It’s hard to be able to join — we don’t let everyone in. But once you’re in, we offer you amazing resources. We call you, we check in on you, we let you join any of our other courses.

It’s also a way for me to think about who I want to be surrounded with. I want to trust the people around me. Coming here taught me that you can treat people like they’re going to do GOOD by default. This profoundly shaped the way I think about my life, my business, and the people I want to be around.

Later, we dined at Tamarine, an upscale restaurant in Palo Alto. When I was a student, this restaurant was too expensive for me. Now as an adult, being able to come here on a whim shows me how far I’ve come.

The wine director even stopped by to say hello and say he and his wife were both IWT students. Thank you Brent and Liz!

On Day 2, we looked at all our breakfast options. American, eggs? No thanks. It was back to…

The day of the reunion was packed with activities, and I got to meet up with old friends and catch up.

We sat in on class panels, where alums talked about what they’d learned since Stanford. I’m deep in the self-development world, and I appreciated hearing moments when people realized what they were doing wasn’t working. 

These conversations can’t always happen in public, just look at high earners asking for advice on Reddit. That’s why I take pride in surrounding my students with other people who understand.

We also visited my old stomping grounds at the Program in Science, Technology and Society. 

This is a very small major at Stanford, and most people found it confusing and wanted something easier to explain, like computer science or econ. But I got to customize my curriculum and studied technology, psychology, persuasion, social influence, ethics, and more. All of this plays into my business today. And I found that if you tell your story right, people are fascinated, not confused.

After my reunion, I got to spend a day with my family in San Francisco. I took them to the Cal Academy to show them the aquarium and penguins. 

Imagine being a kid and seeing this for the first time!

We took a break in a cafe for a bit. My friend Nick Gray once told me that if he went to a museum, he would spend 90 mins tops, and the first 30 would be at a cafe planning his trip. That blew my mind, since I grew up only going to a place once, so we’d spend the entire day seeing everything. This time, I slowed it down, knowing we could always come back. A totally different experience.

When I shared all this on Instagram, some of you were asking how much student loan debt I had after leaving Stanford. I got scholarships that paid my entire undergrad and grad work there. Little known fact: Elite colleges are incredibly generous with their financial aid. (To find out more about my scholarship system, click here.) 

My parents used to say, “Be good enough to get in. The money will take care of itself.”

This is an example of the subtle ways parents who revere education show their values. They visit colleges, talk about why education matters, introduce you to professors and teach you to respect them.

My dad once brought our entire family to Berkeley. He put my sisters on his shoulder and said, “One day, you can come here.” And they did.

My scholarships also paid for ANY books I wanted. This was one of the best things in my life. I literally had an account at the bookstore. Whatever I bought, any book, would be covered. This was my first example of true abundance with books. Ever since then, I never think twice about buying a book. This is the origin story of Ramit’s Book Buying Rule!

I loved sharing my time at Stanford with you on Instagram, and loved reading your comments. Follow me there for more travel stories and send me a DM anytime. I read them all.

Highlights from my 15-year Stanford reunion is a post from: I Will Teach You To Be Rich.