Route 2 FI Interview Series – #9 – FIIntrovert

Reading Time: 15 minutes

Welcome to the Route 2 FI interview series.

I’m starting this series to get inside the heads of people that inspires me on my way to Financial Independence.

Today’s guest is Drew from FIIntrovert.

Drew is the founder of the blog FIIntrovert, which purpose is to help introverts step onto the path of financial independence.

As a INFJ-introvert myself, I was so glad when I found his blog years ago and I’ve been gaining a lot of insight from it.

For us who are still on our path to becoming FI, it’s important who we get our information from.

I hope you’ll find this interview interesting and might learn some things that you can put into action in your own life.



Thank you for having me as a guest.

I love your newsletters and passion for FI.

Hello everyone!

At 39 years old, I have made every financial and career mistake in the book.

The reasons behind those mistakes are complex.

However, a lot of struggle in my life boiled down to how my brain works.

For much of my adult life, I was an ignorant introvert operating in an extroverted culture in the type-A dominated city of Washington, DC.

My inner voice kept telling me there was something wrong with me.

It turns out, my brain just processes chemicals differently from a lot of the population.

In other words, I am an introvert.

Once I learned to manage my days to align with my brain chemistry, life became easier  and more enjoyable – though not without constant struggle.

I was able to have healthier relationships, which eventually led to getting married and recently we welcomed our son into the world.

Rewind nearly twenty years.

I started investing when I was in college during the dot com boom and bust.

Well, I would call that more gambling than investing.

I didn’t really seriously start investing until I was in my mid-thirties, only about four years ago.

I started to sock away as much as possible.

Why? Well, I wanted to escape the extroverted coporate culture.

I felt I could not succeed in that world so I planned my escape by pursuing financial independence.

Freedom from pointless meetings, small talk, forced interactions, and claim over my time.

A funny thing happens when you start to get serious about making money.

I became more motivated to be a better team member and a more productive employee.

To do that, I had to learn about myself.

After I read the book Quiet, my relationships with my coworkers and manager improved drastically – though I still had some difficulties communicating and not showing displeasure and disinterest in long meetings.

However, this was a major improvement over past employers where I was viewed as aloof and arrogant – qualities that get your passed around from manager to manager in dead end positions.

With a better understanding of myself and others, my career and earnings accelerated.

I now have about 80% of the freedom that I would obtain with financial indepdence.

With the birth of my son, I have a whole new appreciation for how rich, fluid, and unpredictable life is.

Each day is as new to me as it is to him as I get to watch him grow and see the world through a child’s eyes.

Even before he was born, I started to regain my childhood joy. In my mid-thirities, I took up long distance running for the first time since I was 18, started skiing for the first time since I was 13, and got a dog, the first I’d ever owned on my own.

Those three things represent some of the loves I had during childhood.

I am enjoying rededicating myself to skiing and running and showering my dog with attention and love (as he does with me).

Your Education

My parents gave me all the advantages in the world when it came to education.

They convinced me – against my strong objections – to stick it out at an elite prep school outside of Washington, DC.

I ended up loving my junior and senior year.

My best friends are still those friends from high school.

The dichotomy is that after a great high school experience, university was a letdown.

Forging relationships over endless nights of drinking led to an unremarkable college career.

September 11th 2001 occurred during my senior year.

I graduated with a general apathy toward life.

I floated around for many years after college.

Eventually, I decided I needed to get an advanced degree.

At 29 years old, I would have been better served to learn about myself and other people than getting myself $70,000 in debt by quitting my job and going to grad school.

However, I do believe our adversity forms who we are.

I got a Masters in Business Administration and a Masters in Government.

As a result of working toward these degrees, I got a job with a health care consulting firm.

That job would launch a new career and earning power.

Your Career

My career in my 20s was a continuation of my unremarkable chapter in college.

My apathy toward life spilled over into my career.

I was bordering on nihilism during my 20s and depressed.

I also had a sense of entitlement because I had gone to an elite high school and college.

I thought that employers should just recognize my pedigree and provide opportunities.

This entitlement and apathy would burn ten precious years of life.

However, I will again state that our struggles make us who we are.

While I wish my 20s had been more productive and positive, I am who I am now because of what I went through.

During grad school, I changed careers.

As a 30 year old, I had an internship while grad school.


After the internship, I embarked on the hardest job of my career.

I worked at what was a two man firm at times – myself and the CEO.

For three and a half years I worked at the edge of my abilities.

At times, it almost broke me emotionally.

However, I started earning six figures in the third of my three years with the firm.

Burnt out and seeing no path to equity, I started looking for a new job.

Then, a break. I found a new job in a niche industry that netted a 40% raise.

I worked hard there for two years and made a lot of contacts – and a good amount of money that I socked away.

I got another new job.

Along with it the new job, another break.

I also got a lucrative consulting contract in the niche industry I was in before.

That consulting contract was wholly based on relationships I had developed.

I never would have gotten that contract if I had not learned about my introversion and what extroverts need.

I kept the relationships – friendships really – going for two years before I got that contract.

Also, key to being able to consult was negotiating with my full time employer.

Understanding people, their motivations, and incentives, allowed me to set up a win-win-win situation for myself, my employer, and my consulting client.

I worked hard for both organizations for two years.

Then, another huge break. I got recruited by an industry contact.

The job was exactly what I had wanted to do when I first entered graduate school ten years ago.

My experience over the last eight years set me up perfectly for the job.

Oh – and the job was remote. I could work from home. No commuting. No getting dressed up.  No political posturing in the office or posing like I was working late.

My son was born two weeks before I started the new job.


 Let’s get on to it, Drew!

I got this theory that every introvert wants to reach FI, but most people don’t know that it’s possible. What is your thoughts about that, and when did you first discover that you were an introvert?

I agree that introverts want freedom.

Financial independence is a vehicle to achieve that freedom.

I believe the reason introverts crave freedom from a desk job is that the small talk, endless meetings, and constant interruptions drain the introvert all day.

By the time the introvert gets home, he has no social energy left for loved ones (or to make romantic relationships happen).

This cycle feels like an empty life.

And no wonder.

We are social animals.

The lost time and energy creates resentment within the introvert.

He starts to dislike people. We see that many introverts label themselves as misanthropes as a result.

At best, the introvert avoids chances to advance in the workplace.

At worse, the introvert is a misanthrope and gets fired.

Either way, it is a bad outcome. The introvert who does not know how to manage all this simply wants to retreat.

I also agree that most people do not know what financail independence is, much less that it is possible.

Once an introvert sees it is possible, the dream of freedom can motivate him to new self understanding, optimal money management, and career sucess – at least that is what it did for me.

What is your personality type? Do you feel your personality has shaped you in terms of getting more “money-wise”?

My personality type is ISTP-T.

I actually think it has been harmful to my financial habits.

I get bored easily and am prone to taking risks just to keep things interesting. ‘

This aspect of my personality has manifested in gambling, betting on penny stocks, and switching investment strategies frequenlty.

It is only since my mid-thirties that I have been able to stick to an investment plan.

However, I still get an itch to swing for the fences when investing in low-cost index funds gets boring.

I look at the gains in crypto, marijuana, plant-based foods and real estate.

I want to switch strategies and go for the kill.

In order to play to that aspect of my personality, I allow myself to allocate 10% of my taxable portfolio to picking dividend stocks and 5% of my portfiolio to specutivaltive stocks or ETFs.

In your post: “Yes Introverts, You Can Enjoy Your Job: Pursue Financial Independence” you explain how introverts can learn to enjoy their job by taking micro-steps to FI. Can you expand a bit on what changes you made in your life after learning about financial independence?

The biggest change I made after learning about FI was advocating for myself to make more money.

I asked for raises, I switched jobs, and I kept relationships going even when I had no idea where they would lead.

All of those activities are hard for an introvert.

It is easier for an introvert to stay in the same job where people let him hide and leave at 6 pm for a job adequately done. Obviously, I started maxing out all my pre-tax accounts, paid off all my student loan and credit card debt, and saved aggressively.

However, the biggest change was focusing on how to make more money and obtain more freedom in my day-to-day job.

Could you tell us about your investing strategy. Do you have a long term plan for your investing?

My investing strategy has been to buy and hold low cost index funds.

As I stated above, I also buy and hold dividend stocks and speculative ETFs (marijuana, artificial intelligence, biotech).

I recently started investing in crowd funded real estate as well.

Lastly, I am allocating more to cash right now as I look into launching a new project that I would try to scale for additional cash flow.

So in addition to buy and hold, my strategy is to diversify.

How many years away are you from FI now? Will you retire early or continue to work?

I do not have a FI date or number.

As I said above, the birth of my son has really changed my perspective.

My new job allows me so much freedom that I have 80% of the benefits of early retirement.

My job is what I call a HIFI job.

High Income. High Freedom. High Impact.

I am learning about myself, traveling, developing new skills, and meeting new people while earning a nice income.

I view all of this as beneficial to my son and me. I would like the option to stop working at 55, which is in 16 years.

Life is so rich and unpredictable though.

I am going to save as much as I can while taking advantage of life enriching opportunities now.

I think deciding when to stop work is like getting married or buying a house – when you know, you know.

Right now, I am not ready. There is still too much I want to learn and experience.

I have a lot of value to add yet.

Could you describe a typical day in your life? What do you want to use more time on when you eventually retire?

The best part of my day comes between 6 am and 7 am.

I hear my son babbling in his room.

I walk over. He hears me. Looks up. Smiles. I make him his first bottle of the day. I talk to him. He babbles back.

We make our way to my bedroom and he says good morning to my wife.

From there, we lay about with him and the dog until about 8:30.

I shower and get a relaxed breakfast as I start my workday.

After working for a good block, I take a break to see my son for a bit.

I may run an errand or go running.

Then I work into the evening.

The dog is ready for his exercise by that point and we go for a walk.

We bathe my son and then put him to sleep.

Then I read or listen to podcasts for a few hours before I go to bed.

It’s a good life.

When I retire, I want to ski, hike, bike, and run in nature more.

Can you give us a timeline of your FI journey, from the beginning with debt and until today? What is your net worth today?

I was about $70,000 in debt in my early to mid-thirties.

I paid that down.

Then I started maxing out my pre-retirment accounts.

For the last three years or so, we have been debt free except for our mortgage.

I have been focused on our after tax accounts for about the last year.

My wife and I have over $900,000 invested in ETFs and crowd funded real estate.

We have a large mortgage in a high-cost of living area.

We estimate $100,000 in equity in our home.

I believe that equity will continue to grow.

Amazon is briniging its second headquarters to within four miles of our home.

That will increase the value of real estate over the next ten years.

We will eventually make our exit to a lower cost of living area when the time is right for us and our son.

About one-third of our wealth came from an inheritance.

We have been working to preserve that money from taxes and anything foolish because it represents a portion of my wife’s great uncle’s time on earth.

To be poor stewards of that inheritance would be to disrespect his life and the time he spent working.

He was a simple man who lived in the same house his whole life.

He worked a simple, honest job.

Through reading the newspaper each morning, he taught himself to invest.

He was a child of the depression who was frugal but not scared of the stock market.

He knew about financial independence and frugality sixty years before this FI movement.

Do you have other life goals than FIRE?

My goal is to be a role model for my son.

I want to teach him the lessons I learned too late.

I want to stay alive long enough to see him become a man and have a family of his own.

Being an introvert, I don’t think I am the best spouse.

I would like to be a better husband, friend, and son.

I also want to qualify for the Boston Marathon. I am pretty far away right now but getting closer.

My training is much better this year so I hope to knock off another 20 to 30 minutes from my marathon time.

Last year I knocked off about 40 minutes.

What are some of the most influential resources (books, blogs, podcast..) that have shaped your money mindset or financial situation?

As I said above, the book Quiet shaped my financial situation.

Emotional intelligence is one of the most valuable tools I developed since reading that book.

People want to deal with dynamic people.

They do not want transactional relationships.

When I started giving more of myself and managing my own day and energy, I started to get a lot more back.

Mr. Money Mustache was definitely a gateway blog to FI for me.

I don’t subscribe to his extreme frugality.

However, it is important to see the extreme and then dial in where you want to be.

Right now, I enjoy Financial Samurai.

We are at similar life stages and I think we have the same outlook on a lot of things.

He has a ton more money than I do and is retired but that’s okay because he’s a lot smarter than me.

I enjoy the Jocko Podcast.

Listening to stories about life and death really puts my life into perspective.

I am actually lucky to go to work, to be alive at 39, to have lived long enough to have a child, to not be subject to a dictatorship, etc.

There is so much to be thankful for.

When I listen to that podcast I feel more grateful and motivated.

Is there an area or area(s) of your own personal finances that you’re still looking to better master and improve?

I just need to be patient.

My fear is flat stock market earnings over the next ten years.

When I get nervous, my wife is actually the one who talks me out of selling and to stay the course.

I’d like to start a business that generates a positive cash flow.

That is going to be a focus for a portion of my capital instead of putting it all in index funds or crowdfunded real estate.

When did you first start blogging? Was there a specific launching off point or what influenced you to go down that path?

I started blogging in November 2017.

Honestly, my blog is terrible.

It is not what I want it to be.

The goal is to make it a resource for introverts to succeed in their careers so they can make more money, invest, and obtain greater freedom through HIFI jobs or financial indepednece.

I just do not write enough or stick to my theme.

Is there a mission statement or underlying purpose to what you intend to accomplish with FIIntrovert?

The goal is to create more valuable content and stick to the theme of helping introverts succeed in their careers.

Are there specific short-term and long-term goals you’re working towards with FIIntrovert?

I have not done a good job of sticking to my theme at all.

The short-term goal is to improve that by creating more content that is on theme.

The long-term goal is to be a trusted resource for introverts who want to grow their careers.

I would like people to see value in my mentorship and coaching one day.

If you could recommend 3 of your blog posts for Route 2 FI’s readers to check out, what would those be and why?

The Secret to Naturally Meeting People – This is a basic concept that escaped me as an introvert. Once it clicked, it became easier for me to set expectations on developing relationships.

Five Alternatives to Financial Independence – FI is not the only way to freedom. I wrote this before I discovered HIFI jobs but these other paths to freedom are worth consideration because they can be useful at different life stages.

Your Personality is Not a Pass – This is my favorite Introvert Interview from Jim at Wallet Hack. He is right on point and a great writer.

At what age did you start investing?

I started gambling on stocks when I was 18. I started investing at 35.

What has been the average rate of return on your investments?

I honestly have no idea.

It is out of my control so why worry about it.

I am invested in equities and bonds throughout the world.

As long as human beings are productive and we continue to innovate, I will have a positive return on investment.

What has been your average annual income up to this point? And what is your average savings rate? How much do you spend annually?

I am not sure what my average is.

I started at $33,000 out of college in 2002.

I drifted in my 20s topping out at about $70,000.

Worked for $40,000 in a three day a week internship.

Then got the consulting gig at $60,000 at 30 years old.

Then $80,000/ Then $100,000.

New job at $140,000.

Got a couple raises there topping out at $165,000.

Took at new job for less money at $145,000.

In 2018, I made about $240,000 as a result of negotiating the consulting arrangement and keeping my W2 job.

In my new job, I will make about $225,000 with a bonus.

Do you think anyone can become a millionaire today?

No, I don’t think anyone can become a millionaire.

I am a firm believer in trickle down economics.

However, imagine rain coming onto a canopy of a dense forest.

The rain trickles down to the shorter trees.

Then to the plants.

Then into the soil.

But some soil is covered by dead leaves and debris.

The rotten decay blocks the water from trickling down to the soil beow where bright seeds might otherwise flourish.

The sun cannot trickle down to these potential seeds of growth either.

I do believe there are segments of our population in the US that are simply cut off from the trickle.

I am not sure what the answer is for those people.

How do we lift them above the debris so they can feel the rain and the sunlight?

When do we try to do that? Childhood? Young adulthood?

Do we make sure that they do not live in poverty in old age only?

Not anyone can become a millionaire.

No. However, we are in a time of great prosperity, wealth, and access to markets.

Most of us can become millionaires.

In your post “Why Can’t Money Buy You Happiness?” you state that financial independence wont make you happy. Can you expand on why?

I believe the pursuit of financial indepdence is what makes people happy.

It gives their day to day monotony meaning.

They enjoy the process of saving and investing.

They feel pride in growing their wealth.

However, a person who is motivated, disciplined, and lucky enough to gain financial independence is not the sort of person who will be satisfied and at rest once he reaches his goal.

That type of person will need a new challenge.

As I say in that post, the beauty of finanical independence is that now the person can self-direct their new challenge rather than it being forced on them by a boss or the need for money.

This is why I love HIFI jobs.

They satisfy most of what financial independence is all about.

High income. High freedom. High impact.

Which 5 steps do you think is the most important to gain financial independence?

1) Become emotionally intelligent

2) Save as much as you can.

3) Eliminate debt.

4) Earn more by being accountable and providing value.

5) Avoid ruin.

Have questions, comments or suggestions? I would love to help you with your FI-journey.

Feel free to reach out directly at @Route2FI on Twitter or email me at

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