Personal Finance

I Paid $4,000 for a Week-Long FI Retreat in Greece—And It Was Worth Every Penny. Here’s Why.

Expertise: Personal Finance, Personal Development, Real Estate Investing Basics, Landlording & Rental Properties
59 Articles Written

I just returned from a week-long financial independence retreat called Chautauqua (pronounced “Sha-tak-wah”) in Greece. When I tell people this, one of the first questions I get is, “Did you go for work? Or for fun?”

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My response? “Both.”

Then I usually get one of these, “Huh?” stares.

I began to realize that I am one of the few lucky people who cannot distinguish between work and fun. While I booked this trip with my own money and took paid time off of work, a lot of the things I did were related to what we do here at BiggerPockets. In fact, I even went with one of my coworkers, the infamous Mindy Jensen, who feels the same way.

Before you read this entire article, let me preface it with this. This is not a post about real estate. It’s a post about why the heck I spent thousands of dollars on a financial independence trip to Greece, what I did, and what I learned.

Side note:Neither BiggerPockets nor I make a penny for promoting this event.

What is Chautauqua?

Chautauqua was started by living the legend and author of The Simple Path to Wealth: Your road map to financial independence and a rich, free life, JL Collins. It is now being facilitated by Katie and Alan Donegan of Pop Up Business School and has quickly become the crème de la crème of events in the financial independence community—a bucket list item for many.

In one sentence, Chautauqua is a financial independence retreat with 40 people from all over the world who believe in ditching a 9-to-5 job to live an extraordinary life.

Many people in the FIRE community feel lonely because none of their friends or family quite understand. None of their friends are saving 50%, 60%, or 70%+ of their incomes, so those who do feel like outliers. Chautauqua makes these folks feel like they belong for once.

But How?

Over the course of the week, you get to know your tribe—these 40 other people who are just like you. When you tell a fellow Chautauquan that you are saving thousands of dollars per month and 50% or more of your income, there is little time spent on “how you do it” and more time spent on the deeper conversations like “why are you doing it?”

While it is described as a “retreat” for folks pursuing or perhaps who have already achieved financial independence, it is much more than that. The conversations you have span much more than money and go much deeper than your typical two to three minute daily conversations. The conversations at Chautauqua can sometimes last 20-30 minutes on the same subject, whether that’s money, political views, family upbringing, relationship, life views, whatever.

The best part is that somehow, everyone knows when to be serious and when to have fun. When you start opening up, no one is there to transition the focus back on them by saying, “Well, I…”

Have you ever spilled your guts out to someone and they answer with, “Well, I…” and they transition the focus of the conversation back to them? This is one of the most frustrating things to me, and I feel as though I deal with it semi-regularly.

For some reason, at Chautauqua, at least during my week, there were none of these people. Everyone understands that there is plenty of time to talk about each individual, so the subject of the conversation remains the subject of the conversation until that person seems satisfied.

What We Did

I think you get the idea now. Chautauqua is a retreat where a bunch of folks in the financial independence community have deep conversations about money, health, relationships, and more. What exactly did we do to promote these discussions?

Each day, there are one or two official speakers, three official meals—and the rest of the day is yours. There were speakers such as the Firecracker from Millennial Revolution, Mr. and Mrs. 1500 from 1500 days, Alan Donegan from Pop-Up Business School, and JL Collins himself.

After the presentation, there was time to hang out by the hotel’s infinity pools, catch some rays, and, of course, chat about whatever we wanted. In many situations, alcohol was involved, so these conversations got even deeper as we drank that liquid courage.

Don’t get me wrong—the week was not just filled with presentations and buzzed conversation. That would get quite boring for most. On one night, we all teamed up and competed in the FI Olympics. My team got in third place—something I’m not too happy about, but I digress.

We also had a day where we got to explore the town we were staying in. Some of us paid Zeus a visit atop Mount Olympus, while others checked out a nearby castle or monastery.

What I Learned

Truthfully, I went into this event thinking I knew everything there was to learn about financial independence. Save a significant portion of your earnings, invest it in assets the produce passive income, and once your passive income exceeds your expenses, you are financially free. Man, was I wrong! There’s so much more.

It is not possible to tell you everything I learned from the event, but I will at least convey to you the big things I took away from each speaker.

Jim Collins: Simple Path to Wealth and

If I were to sum up what Jim said in two words, they would be, “Buy VTSAX.”

It’s comical, but it really is that simple. You ignore the critics and continuously buy shares of the Vanguard Total Stock Market Index (“VTSAX”). When the market is up, you buy. When the market is down, you buy. Ignore the noise, and over time, compound interest and the long-term appreciation of the stock market will make you a wealthy individual.

There are some complexities and ways to make your strategy more efficient. Increasing your savings rate and rebalancing are among the few. If you’d like to learn more, I highly recommend picking up his book.

Kristy and Bryce: Millennial Revolution

The Millennial Revolution folks absolutely blew me away. To be honest, I did not know much about them before going to Greece. Both engineers in their 20s, they were able to retire millionaires in their early 30s, mostly just by saving like crazy. So now that they are “retired,” they blog and travel the world, spending only $30,000 per year for the TWO of them.

This is a dynamite couple! Kristy is always on the hunt for the best deals, while Bryce is looking for advanced ways to access retirement accounts and protect their assets so that they can continue traveling indefinitely.

I can’t wait for their book to come out in the next six to 12 months.

Mr. 1500: How to Find Happiness Once You’re Financially Independent

Carl Jensen, aka Mr. 1500, first off… is THE MAN! I’ve known Carl for a little while now, but I surprisingly learned a whole bunch from his presentation.

For those who haven’t heard his story, Carl was an engineer for the first 15-20 years of his working life. He had a horrible day one week, and when he came home, he started to Google “how to retire early.” He stumbled upon Mr. Money Mustache and fell head first down the FIRE rabbit hole.

He and his wife Mindy Jensen (you may have heard of her) set a goal that they would be financially independent in 1500 days. Lo and behold, they beat their goal and have one of the most popular blogs in the space.

Carl has been retired for almost two years now. The truth is, many people are worried that they won’t know what to do once they hit “retirement.” Carl’s entire presentation covered what to do in early retirement and why you shouldn’t be scared of eternal boredom.

Mrs. 1500: How to Use Real Estate to Become Financially Independent

Mindy Jensen, a.k.a. Mrs. 1500, aka co-host of the BiggerPockets Money Podcast, does not need an introduction on this site.

Not surprisingly, Mrs. 1500 talked about how to achieve financial independence through real estate investing. Her best point was in saying that you don’t need to be in Index funds OR real estate.

You can be in both.

Real estate will likely get you there faster. Index funds will likely be the safer bet. However, the wisest decision might be to invest in both. Speed up your timeline to Financial Independence, but do it safely with a combination of real estate and index funds.

Alan Donegan: Pop Up Business School

I’ll be honest. I had no idea what to expect from Alan’s presentation. I’ve never seen him formally speak. I’ve only heard him on podcasts. While he is very entertaining, I was almost thinking of skipping his presentation because I have no interest in starting a pop up business school (no offense).

However, I felt like a jerk not going, so I went—and I sat in the front row! I’m sure glad I did. He absolutely blew it away. Without a doubt, it was one of the most inspirational speeches I have ever heard. By the end of the presentation, he had everyone ready to get out there to start pursuing their ideas.

The one that stands out the most was when one woman stood up and screamed, “I am going to create a woman’s truck driver business!”

This came from an attendee extremely passionate about the safety of woman truck drivers who wants more of them on the road. Almost everyone was shocked by the idea—and her intense passion!

A handful of attendees helped her get started, and I believe she is now on her way to creating this network of women truck drivers.

Should You Go?

If I haven’t given you enough reason to think of attending by now, then you probably shouldn’t go.

If you don’t like traveling to exotic places, meeting new people, and talking financial independence (without explaining it), then definitely do not go to Chautauqua.

But if you do go, I think that you will find that you have established an unbreakable bond between you and 40 other individuals. By the end of it, you’ll as feel as though you’re all family helping each other pursue the same goal—financial independence and happiness.

I look forward to seeing your pictures!

Would you consider attending Chautauqua? Why or why not?

Weigh in below!

Craig Curelop, aka thefiguy, is the author of The House Hacking Strategy and a driven pursuer of financial independence. Starting with a net worth of negative $30K in 2016, he has aggressively saved and invested to become financially independent in 2019. From sleeping on the couch and renting out his car, he was able to invest in three house hacks in Denver, a flip in Jacksonville, and traditional rental properties in North Carolina. He plans to continue to invest in both Denver and Jacksonville for years to come. Craig's story has caught the attention of several media outlets, including The Denver Post, BBC, Money Magazine, and many other real estate/personal finance podcasts. He hopes to inspire the masses to grab hold of their finances and achieve financial independence. Follow his story on Instagram @thefiguy!
    Cheryl Vargas Rental Property Investor from Rohnert Park, CA
    Replied about 2 years ago
    Wow! This is an amazing article! Makes me want to go to Greece for the next conference, and before that— to read the books you mentioned.
    Christian Carson from Cleveland, Ohio
    Replied about 2 years ago
    Sounds interesting, but my pedantic self must point out that the idea of Chautauqua has been around for a long time… Really pretty lake. It’s a lot closer to home than Greece too. 🙂
    Clay Gradis Rental Property Investor from Newbury Park, CA
    Replied about 2 years ago looks interesting as well, how much fun would it be to take the kids there for some summer classes. Thanks for pointing to this.
    Clay Gradis Rental Property Investor from Newbury Park, CA
    Replied about 2 years ago
    Sounds like an incredible trip, I’ll have to try to join in on one of the near future events. Thanks for the article.
    Ana Perez Investor from Burbank, California
    Replied about 2 years ago
    Very interés place to go and be surrounded with such a great people. Thank you for sharing
    Costin I. Rental Property Investor from Round Rock, TX
    Replied about 2 years ago
    All good and dandy…congrats to all of you…but I don’t see any kids in the pics…so I have to askL how many of you have children? And how much of this wonderful “save 50%+ and FIRE in 1500 days” would apply to a family with kids?
    Jeff White Rental Property Investor from Denver, CO
    Replied about 2 years ago
    Congrats Craig! Sounds like it was an amazing trip!!