A FIRE-Side Chat with Master Duke

A FIRE-Side Chat

Hello folks! I have something special for you today, a FIRE-side chat with the dynamic duo of Chris and Jack from the Duke of Dollars! With a fresh perspective toward personal finance from the perspective of just starting a career (Chris) to about ready to FIRE (Jack), there may be no stopping these Dukes of Dollars.

The FIRE-side chat is an interview series I’ve started to share the journey toward FIRE (Financial Independence Retiring Early) from others. I’m a believer that personal finance is personal and it is important to find our own path toward FIRE. I think hearing from others is a great way to help us formulate our own ideas and our own path.

So without further ado, let’s hear from Chris and Jack and their journey toward FIRE!

Introduction Questions:

First, tell me a little bit about yourself. Who you are and what’s your story?

Thanks JW for the invitation! We’re excited to sit around the Green Swan fire and tell a bit of our story with the personal finance community. We just launched our blog at the beginning of 2017, but the passion for personal finance started much earlier. Soon after we met, we discovered a mutual interest in a strong drive for self improvement. While Jack, the older author, was fine tuning his frugality engine, Chris received his first few paychecks from a full time job. What started as a form of mentorship quickly developed into a partnership as we pushed each other beyond our comfort zones and encouraged one another to succeed in many areas of life. From the on-going dialogues that revolved around money management plans, we decided to convert those text message conversations into blog posts, opening our thoughts to the public and expanding on the topics that interest us most.

There are two authors at the Duke of Dollars:

Chris -> I’m the younger of the two authors: a recent college graduate who endured financial hardship during those years. My parents, who provided for me throughout my life, were in trouble. This instability at home meant I had to get a job, change my mindset very quickly, and start adulting! I went from caring about Xbox Live to instead working so I could pay for my college education. I sought to stabilize my financial environment and also to become a steward of my own time. Both of these mindsets have been the driving forces in my life since, and I’m hoping to inspire the younger crowd to hop on the bandwagon early. The sooner you start on your financial journey, the easier it is to take control!

Jack -> I’m at the tail end of a white collar career. At an age when many of my peers are moving into middle management or senior leadership roles, I’m ready to jump out of the rat race entirely. I developed a lucrative and specialized skill set that allowed me to sell my time to the highest bidder in a global market. I married young and set roots in an area with a low cost of living. Combining a keen sense of frugality with a high income, I was able to sock away a substantial amount of money early in my life. Helped along by a perfectly timed recession and subsequent bull market, my passion for investing turbocharged my retirement efforts, and I’m on the verge of submitting my notice. But first – I have some loose ends to tie up and a few extraneous goals to meet while my marketable skills are at their peak. In other words, I suffer from onemoreyearitis. Part of my blogging efforts are intended to encourage me to more clearly defined my goals and strategies for pulling the escape hatch. While younger readers will benefit from Chris’s fresh and dope outlook (and his memes), the older cohort can tag along for my last couple years on the corporate treadmill.

When did your interest in personal finance begin? Did your parents have an active role in your financial literacy growing up?

Chris -> My interest began after meeting Jack during my college years (~2012) during the time my family was going through financial trouble. The conversation about why he didn’t stop for a soda on his drive home from work every day, due to the “Sharon’s Muffin Calculator” cost intrigued me to learn more. I started reading Mr. Money Mustache’s blog (by starting, I mean read every post that week). I was hooked! From that moment, I added personal finance blogs to my news reader and started incorporating the frugal tips into my lifestyle. This passion with the addition of personal growth has been the catalyst towards my FIRE journey.

Jack -> Money was a secretive and reckless topic in my family. I didn’t a support system coming out of high school, so I took matters into my own hands and immersed myself in the best personal finance writing I could find. Early on, I developed a drive for taking care of myself.

FIRE Journey Questions:

Where are you currently on your path toward FIRE? Just starting, retired already, or somewhere in the middle?

Chris -> Somewhere in the middle. I’m currently maxing out retirement accounts and began my debt free life goal this year. Graduating from college with student loans like many Americans, I want the peace of mind and the removal of that required payment each month. Their interest rates are high enough to warrant paying them off early, compared to outside investment accounts for me. The debt free peace of mind relates back to my initial challenge when going to college and gives me the “why” needed for the required sacrifices! The earlier we start; the friendlier compound interest is to us.

Jack -> I’m on the home stretch. I’m financially independent, but not yet ready for retirement. First and foremost, I have the job that I set out to achieve in the very beginning of my career. It’s exactly the right fit for me as far as lifestyle, work satisfaction, and compensation go. I have minimal desire to leave it compared to some of my earlier, more stressful gigs. On top of the cushy job that I worked hard to secure, the past couple years have been a roller coaster of life events that I never imagined happening, and tracking my every expense to determine if I can retire hasn’t been a priority. The ride isn’t over yet, but as soon as I can exit, I’ll spend some quality bonding time with Excel to see what’s my next move.

If you are already in FIRE, reflect on your path and if there were any things you would change if you had to do it again? Or conversely, what would you make sure you do again on your journey?

Jack –> I’m FI but not RE, close enough that I’ll answer this question. I wish I’d have learned more about investing earlier in my financial journey. Fear and ignorance led me to a slew of missteps in my critical early years. If I had known better to avoid those mistakes, my net worth would be at least 50% higher than it is today. On the flip side, I’m glad that on day one of my journey that I figured out and acted to maximize my contributions to tax-advantaged accounts through automated savings.

Strategizing FIRE Questions:

What has been your primary motivation to reach FIRE?

Jack -> In a nutshell, it starts with self-reliance. I think I can speak for both of us when I say that we feel a strong sense of personal responsibility. This duty to provide for oneself is the root of our efforts to establish impenetrable balance sheets. Our ambitions go beyond just achieving financial independence and extend to the people we love and the community and the world around us. We feel that if we can achieve a level of individual success that allows us to purchase our remaining time on Earth, then we can focus that time and excess capital into making the world a better place.

What has been your greatest success in the “engineering” your life path or lifestyle? Or are you more of the “go with the flow” type?

Chris -> The greatest success in having a purpose aligned with goals for the long-term has motivated me to become better. Life can be a roller coaster full of new job opportunities, relationship changes, and money problems – if we have a plan with a purpose, work hard to achieve our dreams, live up to high character values, and get better every day – it will begin molding into the shape we desire it to be. Strong personal monetary policy intertwined with your goals will lead to strong results!

Jack -> When my income was lower, the by-the-penny approach was the only way that financial success was possible for me. Having developed a sense of the value of $1 during lean times, I don’t rely on charts or budgets at this point. Right now, I’m definitely a “go with the flow” type guy, but I’ll be transitioning back to a black belt Excel ninja over the next couple years while I dial in the formulas to determine if and when I can walk away and sleep soundly at night. I’m excited to be sharing this decision making process with our readers.

I can’t remember where I heard this first, but I hold dear the advice that it is important to “retire to” something rather than “retiring from” something. What will you be retiring to?

Jack -> Chris asked me almost this exactly question recently, and I was honest: I have no freaking clue. Although I’m within sight of the RE horizon, I’m at peace with that answer. I do know that I’ll take about a year to just relax and breathe. I’ve been hustling for as long as I can remember, helping not only myself but also the people I love. I need a break, and the big break is right around the corner. I’m comfortable saying “No” to opportunities that require a lot of my time, and I’ll exercise that skill with gusto after I retire. Eventually, something compelling will float my way, and I’ll be ready with the time, energy, and capital to give it my all.

What will your housing situation be like in retirement? Do you plan on moving to a low cost area, to the beach or mountains? Or will you become nomadic, traveling the world more freely?

Chris -> My early retirement dream has two visions. Living somewhere that gives you access to many different landscapes. A location with beaches, mountains, rural, and urban opportunities; plus a welcoming warm climate. That’s my type of life! Secondly, I would not object to living next to a lovely beach in Florida. Both visions include travelling the world with my wonderful future wife as well.

Jack -> I own a beautiful home in the heart of a happening college town. I’m in walking distance of all necessities and most amenities. This will be my home base for many decades, but I also hope to explore the world on many extended trips.

Wealth Creation Questions:

Retiring early is quite an extraordinary feat…and requires some pretty extraordinary behaviors to rapidly create wealth. In your focus on wealth creation, do you tend to gravitate toward making more money or arresting expenses?

Jack -> Arresting expenses, easily. Contrary to the myriad of retirement calculators sponsored by financial institutions – income is not required to answer the question, “Can I retire?” You need only input your annual expenses and your liquid assets. By my calculations, a penny saved is much greater than one penny earned. A $100 monthly savings is ~$2,500 of invested principal that you don’t need. Internalizing those kinds of figures makes frugality an appetizing choice.

What has been one of your biggest successes in either advancing your career to make more money or taking control on the expense side to progress on your journey toward FIRE?

Jack -> Even before I landed my first full-time job, I focused on the earning potential of my career field. Within that broader industry, I kept a keen eye out for a specialization that was enormously in demand. When that chance came, I had established myself as a hard worker who could learn quickly and produce results. I walked into my boss’s office the day the project was announced and said, “I want this. The whole thing.” I’m now an expert in my craft, recruited globally. I learned a bit late that the phrase “job hopping” is corporate propaganda intended to keep your earnings below market rate. When you have a desirable skill, max it to 99 and then sell it to the highest bidder in terms of your Real Wage. That’s been my greatest success in my FIRE journey.

While controlling expenses are important, you still need to live and enjoy life. What is one or two of your favorite areas to spend money on?

Chris -> Traveling and experiences. Heading to a new place, experiences their culture and seeing their top sights continues to be one of my favorite things to do! Credit card and travel hacking really helps me to find opportunities while keeping cost low. Shopping as a recent grad was a huge expense as I upgraded my wardrobe for the professional world. With my debt free journey underway, it has been on totally on hold. Experiences and travel continue :).

Jack -> Coffee and video games. Over the years, I’ve found ways to achieve the balance of high quality and low expense in these areas.

The Wrap-Up:

If you won the lottery or received a large inheritance to the tune of $1 million or so, what would you do with it and why?

Jack -> I have enough. I’d put the entirety into a self-directed charitable remainder trust. After investing the whole balance into a small handful of companies I select for their ability survive for a figurative forever, I’d set it to reinvest and compound for about 30 years before touching it again. At that point, I’d begin annual distributions of interest, dividends, and other income. I’d write explicit instructions never to sell a single share of any investment or spinoff that existed at the time of my death. 50 years after my death, I’d instruct the trustee to sell everything and distribute the entirety to a single entity. Something like that.

Chris -> I’m with Jack here – it would be a great opportunity to impact the world like the Hershey Trust. A second consideration would be to utilize it to provide for generations of my family to use for their children’s college expenses.

What is your favorite finance and non-finance related book, podcast, magazine, blog, etc and why?

Chris ->

  • Podcast -> School of Greatness – Many great people who have impacted the world are interviewed by Lewis Howes, a professional football player who turned entrepreneur. My favorite thing about his business has been him using money from it to build a school in South America – inspiring person doing inspiring things.
  • Book -> Inheritance Series – The fantasy story weaves many life values into a great story about a young farmer turning into the world’s greatest hero. It reminds me that each of us, if given the opportunity with character and defiance, can achieve what we want in the world!
  • Blog -> Joshua Kennon – He has helped transform the way both of us think, live, and invest. He has had an influence on our lives without ever meeting him in person. Not only his blog, but his investing articles on about.com have helped tremendously as well!

Jack ->

  • I love the classic novel. I’m slowly working my way through the best novels ever written as defined by a myriad of lists made by random people on the internet. I try to read novels from all geographies and time periods, though I have a preference for modern American writing. So far, my favorite novels that I’ve read recently are The Corrections by Jonathan Franzen and The Winter of Our Discontent by John Steinbeck.

What advice would you give to folks considering or just starting their journey toward FIRE?

Jack -> Start now. Invest at the beginning. It’s a long and wide road with plenty of room for mistakes, side quests, personal growth. Life has a way of taking you down paths you didn’t foresee, but you’ll never find yourself at a fork in the road thinking, “If only I had less money, this decision would be easier.” Whether you end up retiring early or not, learn that money is a tool to serve your needs and desires. It opens doors, makes enduring hardship easier, and allows you more agency over an unpredictable life.

Chris -> Totally on the same page as Jack on this one. We’ve wrote about it before – follow the progressive overload principle and begin little by little, adding into a database of personal finance knowledge for your future!

If you are a fellow blogger, where can I find you?


Duke of Dollars

Social Media:
Master Duke on Twitter



Thanks for sitting down and chatting, Chris and Jack! What a pleasure having you both!

I hope you give the them a follow and check out their blog. Look for more FIRE-Side chats to be featured here in the future. And if you are interested in a FIRE-Side chat yourself, give me a shout.

Thanks for taking a look!

The Green Swan



share on:


  1. TIL Chris and I would get along pretty well ha! We’re half way to RE too but there’s no hurry, we’ll just see what’s on the horizon. Plus if you include kids…nope not even 1/3 there.

    I could want to live in the middle of nowhere too but hubby is very against that idea so in Seattle we stay.

Leave a Reply