Why I Founded The Simple Dollar

Over the years, I’ve written about my own financial turnaround in bits and pieces, with an article here telling one piece of the story and another article over there telling another piece. Today, I thought I’d lay all of it out in one place, something of a financial and life biography that hopefully I can link back to in later articles for clarification.

So, let’s start from the beginning.

I grew up without a lot of money.

I grew up in rural Illinois, far away from the Chicagoland area, with two really loving parents. I cannot possibly say enough kind things about them.

My mother was a stay-at-home mom when I was young, taking care of me and my older brothers. She handled most of the domestic chores, though my father handled some of them, and was a pretty fierce advocate for us in school. She never missed any of our school events and made sure our home life was as smooth as possible. When I got older and my two older brothers were moved out or close to it, she took a job as a postal clerk.

My father worked most of the time in a factory making heavy machinery. Early on, he was a welder, but later he took on some special training and helped with inventory management and part retrieval. His shifts were erratic and there would be periods where I wouldn’t see him much even though we lived in the same house. The unfortunate part was that he was frequently laid off from this job, as the factory would close down during periods of low demand. He supplemented this job with several side gigs, most notably a small commercial fishing business.

We never had a lot of money growing up. I never really felt in danger of not having food on the table, but our house was small and there were a lot of things our friends had that we didn’t. We went on precisely two short summer vacations that I can remember during my entire childhood; most summers, the highlight was a camping trip somewhere within an hour or two of home. Sure, we had times where things were good, but there were some challenges.

My parents dealt with this by being very frugal. We had an enormous vegetable garden and preserved a lot of the produce, particularly through canning and fermentation. My dad kept a portion of what he caught in his commercial fishing business. We also hunted for some of our food supply and even gathered berries and wild mushrooms in the right season.

I went to college and tried to stay frugal.

I got into a pretty good college and, thanks to my parents’ relatively low income and my solid academic record, I was able to get a nice collection of need- and merit-based scholarships and grants that paid for a very large portion of my education. My parents didn’t really have the means to pay for the rest, so I did have to take out some student loans to supplement that aid.

During the first few years of college, I lived as cheaply as possible. I lived in the dorms for a while, and then I lived in a couple of very tiny apartments. I did almost everything as cheaply as possible. I practically lived on ramen noodles for a few years, wore a lot of secondhand clothes, and ate a lot of free meals on campus. I actually joined a bunch of on-campus groups simply for free meals.

Later on, I started to work at some internships and jobs related to my field of study. I got myself on track to get a nice job in the field of genetics data analysis and it became clear that I had multiple good job offers coming my way as I neared graduation.

That caused me to loosen up a little with my spending. I got my first credit card during my last year of college and built up a small balance on it, figuring I would pay it off when I got that nice job. During my last few years of college, I started seriously dating Sarah, who would eventually become my wife.

I graduated, and then things really started spinning out of control.

My early professional years included a lot of overspending.

As I had expected, I got a solid “entry-level” job in my field of choice upon graduation, where I had a ton of opportunities to build up a good skill set and get to know a lot of people in my field while also making solid money. This job was in central Iowa, among the many companies and organizations that are involved in biological and medical research, so I chose to settle there. Sarah found a teaching job about an hour away from my job, so we found a nice little apartment halfway between the two jobs and settled in.

It wasn’t long before the floodgates on our spending opened wide. We decided to get married shortly after our graduation and wanted time to plan out a “really great” wedding. While the wedding did have some frugal elements to it, we certainly spent a lot on that event, and we spent a lot more on our honeymoon, which was a 10-day trip to the United Kingdom.

That trip and much of the wedding was financed with debt. We put most of the cost of all of it onto credit cards, believing, again, that we would pay it off in the future.

At the same time, Sarah and I were settling into a lot of expensive life routines. We ate out for a lot of our meals, only making meals at home for occasional novelty. I started hanging out with a group of young professionals in the area in my field — there were a lot of us at the time — and we went out for drinks and appetizers many days after work. I also started golfing a lot with a few of them. We got into fairly expensive hobbies — Sarah got into wine tasting, and I started buying a lot of video games and computer games. Both of us were passionate readers and started rapidly accumulating books. We both bought new-ish cars. We furnished our little apartment with some really nice furniture. We invited family and friends to visit and treated them quite well.

Much of that spending was financed on credit cards and other forms of debt. At the time, we really held onto the idea that we would be able to pay all of it off in the future when we were making more money, but as we both got some nice early-career raises, we weren’t paying things off. Rather, we were digging more holes.

For our first anniversary, we traveled to Mexico and to the Pacific Northwest. For our second, we traveled to Las Vegas for several days, going to Hoover Dam as a day trip and to the Grand Canyon over one night.

The debt was piling up.

Sarah and I really only made one smart financial move during those early years: we both contributed pretty strongly to our retirement plans. I can’t tell you how glad I am that we did this, because those contributions have grown a lot since then and is the foundation of our retirement plans.

Our first child arrived, and with him came a lot of changes.

When we learned that our first child was on the way, it was a moment of celebration. We knew we wanted to have children and, although this was perhaps a bit earlier than we thought it would happen, we were still thrilled. This was our big plan, all along!

However, with Sarah’s pregnancy zipping along, we both began to have some mild second thoughts about the direction of our lives. For example, I wrote this journal entry in my personal journal one day during her pregnancy.

Then, our first child was born, and when Sarah returned to work after maternity leave, things got interesting.

For starters, the costs of having a child hit us hard. He needed all kinds of things, and most expensive of all was child care. We were exhausted, as all new parents are, and we spent several months leaning heavily on takeout food and other conveniences.

Needless to say, our credit cards started quickly boiling over and we started to have difficulty paying our bills.

This all came to a head one spring afternoon where I came home from work and sat down to pay bills, only to realize that we didn’t have enough money to pay them. This state of affairs seemed completely ridiculous and unacceptable, and I was ashamed of myself. Sarah and I both had really good jobs and yet we couldn’t afford to even keep our bills paid, let alone make any progress toward our dreams?

We wanted to eventually move into a nice family home with a big yard for our kids to play in. We talked about retiring at the earliest possible moment and doing a lot of traveling around the country together. Those dreams felt like they were fading away, more distant than ever.

So, we decided to start making some real changes.

Our first wave of change was intense.

Within a day or two, I went to the library and checked out a giant pile of personal finance books. Most of them didn’t speak to me in any way, but one really stood out: Your Money or Your Life by Joe Dominguez and Vicki Robin.

The ideas behind that book nudged Sarah and I down a path of pretty intense frugality and some pretty rapid life changes.

I basically checked out of that group of young professionals — no more after-dinner drinks and appetizers, no more one-upping each other with gadgets and clothes, no more golf outings. I completely stopped buying new video games and books; instead, I started using the library a lot more and started playing the games I had to a much deeper level. Sarah and I started cooking at home every night and making lunches for each other for the next day — we went from eating out for lunch and getting takeout for supper to home-cooked suppers and brown bag lunches almost overnight.

At the same time, we purged a lot of our possessions. I sold off most of our DVD collection, a lot of our book collection, most of my video games and a bunch of my sports cards and trading card collection.

We took that money and hit our debts hard. We annihilated most of our credit card debt pretty quickly and within a few months, it was mostly gone. We had some money in savings for emergencies. Things were much better.

At that point, we started to relapse a little. We started getting takeout fairly often. I showed back up at that young professionals group a few times. We bought some books. I picked up a few video games.

After a month or so, Sarah and I sat down together and talked about our future, and we realized that we simply did not want to go back to the way things were. We felt we didn’t need to be quite so intense with frugality as we were at the start, but we wanted to be on a strongly positive financial track.

So, we started evaluating all of the changes we made really carefully. Which of our new routines made a lot of sense? Which of our old routines did we really miss? It turned out that, for the most part, we preferred our new frugal routines, because we knew those routines came with optimism about the future, less stress and more peace of mind.

That’s when The Simple Dollar was born.

Around then, a few friends wanted to know what we were up to. They hadn’t seen me around lately and were just checking in, or they had noticed that I was doing some things differently.

I decided to answer them all at once and basically just wrote down everything we had learned about personal finance during those few months of turnaround, and I sent it out by email.

I got a lot of positive feedback from that email, and a couple of people asked if they could send it to some of their friends, too. A few people asked some follow-up questions, including an email from some guy I didn’t even know! Apparently, my email had been passed along to him.

So, I wrote a follow-up email and sent it to the original people I sent it to and all of the new email addresses I had. That one was an even bigger hit and it got passed around to a lot of people. Again, someone I didn’t even know who had seen the email as a forward wrote to me and said I should turn this information into a website.

That website was The Simple Dollar version 0.1. That’s literally how the site started. I turned those original emails into a few of the earliest articles on the site, and I sent out the URL to those friends.

In my spare time, I kept writing about our financial turnaround. I wrote about how we paid off our credit cards, paid off our car loans and even paid off our student loans, and how we used frugality to do it.

Over the first year of the site, I wrote hundreds of really short articles, and the site made a pittance. I could see that the readership was slowly ramping up, but I didn’t make any money from it. Rather, it was a way to collect my thoughts about our financial experience — what was working and what wasn’t. It didn’t take a whole lot of work to keep the site running then, as it was pretty low traffic.

At some point, for reasons I don’t really understand, the traffic growth really took off. I had a friend who knew something about monetizing websites give me a bunch of advice about how to turn that traffic into a nice side gig, which was great, but the site took up more and more and more time.

As The Simple Dollar was taking off, Sarah and I had a second child and saved up for a down payment on a house, because our tiny apartment wasn’t going to work with two young children. We found a great house at a great price and moved.

What happened next?

Within a year after moving, I was at a crossroads with The Simple Dollar. It was simply taking up too much of my time to keep it going as a side gig. I was also experiencing some frustration with my primary career.

Sarah and I had a number of conversations about it and we decided that I should take a year or two off from my career, keep the kids home with me at least a few days a week to cut our child care costs, and see if I could turn The Simple Dollar into a full-time job.

That decision was a hard one. It meant a significant drop in income, and it meant I would be working from home and being a stay-at-home parent much of the time.

It worked out. Within a couple of years, we had a third child, Sarah took most of a year off of work for maternity leave, and I leaned into building The Simple Dollar hard.

After a year of building and working and burning the candle at both ends, though, I began to feel overwhelmed again. There was too much to do to keep the site going and the income wasn’t exactly making us rich. We were doing fine, but we weren’t doing great.

We were thriving financially, but it was largely due to our frugal lifestyle, not due to making a mint from the website.

Gradually, I started hiring help for The Simple Dollar. The site kept growing gradually, but the work needed to grow it kept growing as well. The problem was that, before long, I was spending more time managing people than I was spending actually writing and connecting with readers, and it was that writing and connecting that was what I enjoyed. I was trying to do all kinds of things to really grow the site (I wrote some books, I got involved with a potential reality show, and many other things), but what I realized was that I really just wanted to write really good material and put in the time to create stuff that really affected people.

During all of that, Sarah and I actually managed to pay off our home mortgage in about four years, leaving us completely debt-free, which was an incredible feeling.

However, I was burning out on managing The Simple Dollar, so I started talking to other website owners about different possibilities that would let me focus on articles and not on backend management and ad sales and all of that other stuff, and I eventually found the right arrangement and sold the site with a very long term agreement for me to stay around as the primary writer. If I hadn’t done this, I don’t believe The Simple Dollar would exist today, as I would have just burned out completely and probably turned back to my old career.

What’s happened since then?

Sarah and I set a long term goal of early retirement. We hope to retire around the time our youngest child fully leaves the nest, a decade or so from now. I’m trying to be the best parent and the best husband I can possibly be.

We’re still living the frugal principles that got us here, with some natural refinement over the years, and I’m still writing about those refinements and the things I’ve learned along the way.

Thanks so much for reading, both then and now, and I hope that you’ll stick around for the rest of the journey.

Trent Hamm

Founder & Columnist

Trent Hamm founded The Simple Dollar in 2006 and still writes a daily column on personal finance. He’s the author of three books published by Simon & Schuster and Financial Times Press, has contributed to Business Insider, US News & World Report, Yahoo Finance, and Lifehacker, and his financial advice has been featured in The New York Times, TIME, Forbes, The Guardian, and elsewhere.