Finding FI Interview #23: How Dylin achieved fatFIRE before knowing It

Michael QuanBeliefs, Education, FI / FIRE, How to, Interviews, Misc2 Comments

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Welcome to the Finding FI interview series where we highlight and learn from individuals focused on achieving financial independence and the strategies they are using.  Everyone is at different stages of their FI / FIRE (financial independence, retire early) journey, so let’s learn from their personal stories and be inspired.

Finding FI Interview #23

Today I have a special guest, Dylin, from Retire by 45. He’s got a great story on how he retired at 43, and a varied work history you’ll have to read about. 

Take it away, Dylin!

Finding FI Question #1

What’s your story?

Finding FI

I’m 48 years old, and I live in Oakland, CA with my wife, Allison. We FIRE’d at the beginning of 2015, and we have never looked back.  In 2016, we started our blog Retire By 45, which provides inspiration, tips, and resources to help others reach FIRE.

Allison and I fell into FIRE totally by accident.  We were both laid off from our tech start-up jobs in San Francisco within a month of each other.  What could have been seen as bad luck actually turned out to be a blessing in disguise.  

Initially, we thought we would just take a few months off to travel and recharge ourselves.  But our little sabbatical turned into a permanent vacation after we crunched the numbers and realized we didn’t need to go back to work.  

In addition to working on our site, we do a lot of stuff that perhaps traditional retirees would do:  we’re involved in our community, we travel domestically and abroad, we eat out a lot and go to museums and shows, and we’re very into health and fitness.

Michael here – Cool story, Dylin. I like that you took a few months to yourself to recharge yourselves before making any major decisions. I think a lot of people would enjoy a permanent vacation!    

Finding FI Question #2

What types of routines and/or life hacks do you use?
  • Automation — We’re all about the “set it and forget it” strategy with our investments and expenses.  We pay everything we can automatically, including insurance, credit cards, and HOA dues. Before we FIRE’d, we put all our investments on auto-pilot, including contributing to 401(k), IRA, and taxable accounts.
  • Frugal Living — We actually really enjoy living the frugal lifestyle.  We save money by buying in bulk, driving used cars, doing things ourselves (we’ve completed several plumbing, painting, and insulation projects over the years), and getting (and giving away) stuff for free.  We haven’t bought new clothes (other than underwear, socks, and shoes) in probably 15 years, because we get all of our “new to us” threads from clothing swaps.  
  • Travel — We just started getting into “travel hacking” with our new Chase Sapphire Reserve credit card.  We also tend to save money when we travel by staying in AirBnBs or hostels, taking public transportation, and looking for deals on tours and cruises.

Michael here – DIY and Travel Hacking… tools of the trade when it comes to FIRE! 🙂  

Finding FI Question #3

Describe your past relationship with money. How has it evolved into your present views today? How do you want it to change in the future?

I like to tell the story about what initially changed my perception of money.  I was in my mid-20s when I first met Allison. We were food servers in a big sports-themed restaurant located in the middle of Times Square in NYC.

We made most of our money from cash tips, and after work we would all go out and spend half of it at our favorite local tavern.  One night, Allison saw how I was treating my cash — just crumbling up and shoving it into pockets without much thought.

She taught me that I should treat my hard-earned money with more respect.  She showed me how to put it in nice orderly stacks tucked away neatly into my wallet.  What seemed like such a small and basic lesson had a profound impact on how I viewed money.  By being more mindful about money, it really helped me with my spending and saving habits.

See also4 Money Lessons I Learned from My Super Frugal Wife

Michael here – It’s fun to see how life evolves over time and how seemingly little events can shift our mindset.      

Finding FI Question #4

What is something about yourself that only your closest family and friends know about?

Here are some random interesting facts about me that most people wouldn’t know:

  • My parents met at the Playboy Club in Manhattan in the ‘60s.  My mom was a bunny and my dad was a floor manager.
  • Was born in Southern California, one day before a massive earthquake 
  • I had a near death experience in 2009 when I got double pneumonia and was in ICU for 10 days
  • Got Dengue Fever in Thailand and had to spend 3 nights in a hospital in Chiang Mai
  • Although I retired at 43, I’ve held over 30 jobs in my lifetime, including 11 different Internet startups in San Francisco
  • Before getting into Internet jobs, I tried being an actor for several years and had a lead role in an Independent horror film

Michael here – Wow, you’re an interesting, dude! You can’t say you haven’t tried a lot of things. I’ve always wondered… is filming a scary movie actually scary?  


Finding FI Question #5

When did you first hear about FI/RE?

I heard about FIRE in late 2016 / early 2017, which was about two years after Allison and I already achieved FIRE.  

We had originally started a site called Experiencify, which is a travel blog encouraging readers to pursue amazing life experiences.  One of my early blog posts described how Allison and I were able to retire in our early 40s.

That article got a lot of buzz, which made me realize there was a sizeable audience just for that topic.  I bought the url and started writing about our experiences as early retirees.

A few months after I launched Retire By 45, a podcaster contacted me for an interview.  During our conversation, he asked for my thoughts on the “FIRE movement.” I think I just said something like “yeah, I think it’s great,” not knowing what he was talking about (although realizing that I should know it).  I Google’d it afterward, and needless to say, my mind was blown.

Michael here – Haha, that’s funny that you learned about FIRE live on a podcast! It’s great to see the FIRE movement continuing to make strides.   

Finding FI Question #6

Why does FI or FIRE appeal to you?

Maybe because I’m an only child, I’ve always been very independent, resourceful, and entrepreneurial.  One of my all-time favorite jobs was my part-time college job delivering meals from restaurants. This was in the early 90s before DoorDash and Uber Eats.  

Customers would call the main office and order something from the paper menu guide, which had more than 30 restaurant menus.  The office would dispatch the order to the nearest driver over a walkie-talkie. As a driver, you could do anything you wanted in between pickups, so it was total freedom.

The FIRE lifestyle is a lot like that.  It gives you total freedom and independence to do what you want and what makes you happy.  You can work on whatever personal projects you want. You can volunteer and help others. And if you only want to travel and explore the world, you can do that too.

Michael here – Excellent analogy. Freedom and independence are what it’s all about.    

Finding FI Question #7

What type of FIRE are you pursuing (i.e. leanFIRE, FIRE, fatFIRE)?

In many ways, Allison and I were lucky that we FIRE’d accidentally because we didn’t know anything about the 4% Rule, FI numbers, etc.  So, when we crunched our numbers after learning all this stuff, it turned out we were already fatFIRE (Allison likes to say that we are AmpliFI’d, because we have more than enough to fund our lifestyle very nicely).  

If we had known all the rules of thumb, we may have FIRE’d sooner.  But I’m glad we spent more time building up our nest egg to better prepare for any crazy unexpected downturns / catastrophes that could happen in the future.

Michael here – Where will you go from here? fatFIRE is quite the starting point. 😉   

Finding FI Question #8

How has life changed since reaching FI? Or, if you haven’t reached FI yet, how will it change?

It’s changed in many ways, mostly for the better.  We live life at a slower pace now. Before, we were always in a hurry – to get to work, to get home from work, to do our shopping and errands, to work out, etc.  Now we do things with much more of a mindful intention and enjoyment.  

Overall, our lives are much healthier now.  We eat better, sleep better, and tend to our minds and bodies much better.  We have more time to be social. We’ve gotten to know our neighbors and local merchants, which we rarely ever did when we were always working.  

We travel much more now, too.  We’ve been to a couple dozen countries, including the Mediterranean, SE Asia, and China.  And we’re always planning a new adventure. Our next one is a 2-3 month trip exploring Spain and Portugal before venturing down to South America. 

See also: 10 Cool Things We’ve Done Since Achieving FIRE (& 5 We’re Planning)

Michael here – Health and wealth go hand-in-hand. Enjoy your trip to Spain and Portugal! I love Spain but haven’t had the opportunity to visit Portugal yet.   

Finding FI Question #9

Do you actively speak with others about FI / FIRE?

We try not to speak too much about it to friends and family, unless they ask.  When I first started blogging about it, I would regularly post our articles on my personal Facebook page.  

I think our friends really enjoyed those blog posts at first but then got a little tired hearing about how awesome our FIRE lives were when they were still grinding away at stressful jobs.  So now I keep my posts mainly on our business pages.

We do enjoy meeting up with others in the FIRE community. We belong to a number of FIRE-oriented Facebook groups, and do a fair amount of Meetups in the Bay Area.  It’s always fun getting together with like-minded people, and discussing where they are on their FIRE journeys. 

We will be attending our second FinCon next month in DC, and are really looking forward to hobnobbing with all the FIRE fans, bloggers, and podcasters.

Michael here – Sorry our paths didn’t cross at FinCon. I was going to say hi and one point and then we each got pulled in different directions. Hope to see you next year!   

Finding FI Question #10

Is a side hustle a key component of your FI / FIRE journey? (i.e. second job, side biz, real estate investing, etc.)?

I had a few side hustles over the years, but one, in particular, was very lucrative.  In the mid 2000’s, I set up an affiliate business using online dating offers like, True, eHarmony, etc.

Rather than promoting them on a website, I ran Google Adwords ads and linked directly from my ads to the dating sites through affiliate links.  Unfortunately, Google cracked down on this practice a long time ago, but I took full advantage while it was allowed on their site.  

For a couple of years, that side business earned more than my regular full-time salary. We took all the proceeds from this business and funded a SEP-IRA and taxable account.

Michael here – That’s awesome! Gotta take advantage of opportunities when they’re available.

Thanks again for sharing your story with us.   

Readers, what is your favorite takeaway from Dylin’s story?

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2 Comments on “Finding FI Interview #23: How Dylin achieved fatFIRE before knowing It”

  1. For me it was that Google affiliate thingy he did that earned him more money than his full-time salary! Awesome!

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