Today’s 10 Questions features Jason from Winning Personal Finance! Jason has a lot to say, so I’m going to shut up and let Jason get right into it. Take it away Jason!
There are approximately 476,492,292,928 personal finance blogs last time I checked. Why should we read yours?
We’re lucky to have so many options for our entertainment and knowledge. It’s amazing there are so many choices that we can each find one – or more – that resonates with us. I encourage everyone to find content that educates and motivates them to take the needed steps to improve their lives and reach their goals. I hope my voice does that for you but if it doesn’t, find one that works. I write about everything from choosing between a Roth or Traditional 401(k) to teaching my preschooler to play poker and being a sucker for bacon. Since this is my first question, I’ll give a quick blurb about myself and maybe it would intrigue you to learn more. I’m currently 35 and a “family man.” I live with my wife and two boys (ages 4 and 1) in the New Jersey suburbs of New York City. I believe there’s no better feeling in the world than coming home to a baby screaming “dada” when you walk in the door while the preschooler is running around like crazy out of excitement from your arrival. I’m a
What is one post that you’ve written that you wish would have gone viral?
This post with an easy hack to become a millionaire. While not everybody will be able to get there by age 43 like my imaginary friend Jane, the trick should work for anybody motivated enough to grow their income. The biggest push back I get from folks who don’t want to worry about their personal finances is that they don’t want to save because they don’t want to make any sacrifices. The approach described eliminates that excuse.
Why did you start your blog?
- I’ve relied on blogs and financial books to point me in the right financial direction from the start and I’ve thrived.
- I wanted to make more of a difference in the world. Working in corporate finance pays the bills but doesn’t give much in terms of life satisfaction from helping others. I figured I’d be able to write blog posts during my commute without giving up any “quality time.”
- I’d always said my dream “early retirement job” was to help others build wealth, I figured the blog would be a way to get the ball rolling on that goal while I was still working to reach financial independence in corporate America.
Transportation (how do you get around): car, train, bus, bike or VTOL.
I have a very long commute right now from the NJ suburbs to New York City. It takes between 1.5 to 2 hours each way. I walk to the train from my house and to my office once I get to NY for a total of 2 miles of walking each direction. I walk because we are a one car family. I don’t want to pay for a second car and a parking spot at the train just to avoid some forced exercise. On the rare occasion that having one car on the weekend is not acceptable or if our Altima can’t handle the burden of all our stuff on a road trip, we’ll occasionally indulge in a rideshare or renting a bigger car. If this sounds awful, well sometimes when the weather is bad, it is. I’ve made the most of the commuting time though. As an introvert, this is truly the only time during the day that I have to myself. I initially used it to read. Then I discovered podcasts and finally started writing my own blog on the train. More recently, I’d used this time to study for my CERTIFIED FINANCIAL PLANNER™ exam.
How do you stay fit? (If you’re one of those crazy Crossfit people, please don’t tell me that I suck because I don’t do it. This has happened.)
Years ago, I ran a couple of marathons and staying fit was not really a problem. Once my first son was born, I’ve had a harder time choosing exercise over family time and my fitness level and waistline have suffered. My past strategy has been to set goals that scare me into working out like running long distance and obstacle course races or climbing mountains. This year, I’m going to try and add a small daily workout habit to my morning routine and hope that helps.

Financial Independence, Investing, and Money
Is your goal financial independence? If so, where are you on the journey?
Isn’t everybody’s goal financial independence? I know that not everybody achieves it but I can’t imagine any other personal financial goal. What other alternative is there? Planning to rely on friends, family or the government to survive? So yes, my goal is FI and I’ve actually had the goal from the day I started working full time. Watching Office Space one night during orientation at my accounting firm may not have been such a good choice to motivate new hires. I didn’t really have career ambitions from the start but I had lots of things I wanted to do outside of work. I understood that if I’d saved enough, I’d have the ability to “buy back my time” and spend it how I wanted. This led me to start saving a good portion of my entry-level accounting salary from the start by living with my parents for two years after graduation, never buying a car, and choosing residences that were well below our means. I calculate that I’ll hit a high cost of living FI number at 45. Initially, I was trying to FIRE as quickly as reasonably possible. Now, I’m a bit more focused on life design. If I can fit meaningful work that I enjoy around all the other stuff I want to do with my time, I’d be okay working much longer than 45 years of age. I
You rub a magic lamp and an evil genie pops out and says this: “You must pick one, specific investment to have all your money in for the next decade!” What do you pick?
Easy choice, I’d pick a super low or no cost total stock market index fund. A majority of my investments are allocated to this type of fund already.
Evil genies aside, what is your investing strategy? Stocks? Index funds?? Real estate??? Crypto????
I don’t own any individual stocks, just index funds both in and out of retirement accounts. No Crypto either. I get that crypto may have a functional purpose but can’t really understand it as an investment. From a real estate perspective, I own my personal residence. I had rented out my first condo for a little while and did not really enjoy the landlord thing. I do believe there’s a path to wealth in real estate but it’s not really passive. I choose to focus my time and assets elsewhere right now.
What is your favorite money management tool? (Yes, you can include your affiliate link.)
Can I say Excel? I’m a spreadsheet junkie and as much as I try, I still can’t find any software I like better than the classic program from Microsoft. I use Mint to aggregate my transactions and then just dump them into my spreadsheet for the analysis.
Money
What is the best thing you ever bought? The worst?
The best thing I ever bought was my wife’s engagement ring. I know it’s a bit corny but she completes me. We’ve been together since we were teenagers and I can’t imagine life without her. Sure the rock was expensive but she said yes! Best-Investment-Ever! My second pick may be the book Job Interviews For Dummies. In a job interview, you need to aggressively accentuate the positive. Being conservative by nature, this comes very unnaturally to me. I’m pretty sure all of the success I’ve had in job interviews is somewhat related to this gem of a book. I’ve reread it with each career transition and it’s always helped to put me in the interview mindset. As for the worst, I’m going with the white picket fence we added to our home. At the time we figured it would keep the kids and/or potential future pets in the yard. It cost thousands of dollars. I’ve blocked out the exact amount from my head. My son was able to open the gate as soon as he could walk. Even without it, I trust him to stay out of the street. We still don’t have a pet. It’s a royal pain every day to have to open a gate to get to the house from our driveway, which is outside the gate, especially with our hands full as they normally are with two kids. Now I just prop it open all the time.
What is your splurge? Don’t be shy. Mine set me back $45,000.
In looking at my budget there are

Your best friend tells you that he just got a raise at work and is going to buy a new car to celebrate. His current car is in perfect working order. How do you react?
I’ll do my best to gently question that the increased expense won’t impact reaching any higher priority goals and offer to work through a new budget with him to make sure. I’d also try and subtly forward him this post about the impact of car expenses. In general, my friends tend to do well from an earning perspective and are not shooting for early retirement so there’s a good chance they can afford the new car while staying on track for their goals. If that’s the case, I’d just wish him the best on his new car and happily let him do the driving if we carpool somewhere.
Children
What is one unique thing you’re doing to raise your kids to be financially smart?
I do my best to teach 4-year-old son finance and economic concepts at a preschool level. One day we emptied his piggy bank and put the money in the bank. That money magically pays him cash interest whenever dad has singles. I don’t give him an allowance or anything yet but I think this concept teaches passive income and the benefits of saving and investing. When we were just in Disney, we give him a budget of $30 to buy whatever he wanted. It was great to hear
Travel
Ideal vacation: road trip, beach, mountains, forest or city?
Mountains for sure. I avoid the city like the plague outside of work. My ideal vacation is staying slopeside at a ski area known for good snow and big terrain and having the budget for lessons and guiding so that everybody gets the most out of the trip.
What is the most beautiful place you’ve ever seen?
Flying by the Matterhorn via helicopter on my way to ski Monte Rosa in Zermatt, Switzerland. That whole day had mind-blowing views of open

Big Questions
How is the world going to be better because you lived?
Until this point in my life, I’d say my biggest contributions would be my children. I don’t think this is enough though. During my current “midlife crisis” I studied my butt off to start a career as a financial planner that will probably pay me less money and is all about helping people. I’m doing this because I believe it’s the best way for me to leave the world a better place. I think there are millions of people out there who would benefit from an advice-only (no commissions or assets under management) brand of financial planning. This is what I’m starting to practice because I believe in it.
What is one thing you believe that most others do not?
A car is a way to get from point A to point B, nothing more.
If you could change one thing about yourself, what would it be?
I wish I was a bit more extroverted. While I like (some) people, I’m super happy to be alone doing my thing.
What is something you’ve read that changed your life?
In my first year working full time I read “The Automatic Millionaire” and “Rich Dad Poor Dad.” I bought those books knowing I wanted to build wealth and do it fast so I already had the right mindset. The books helped shape my decisions though and helped me keep a close eye on small spending habits (aka coffee) and big decisions like cars and houses.
Random Silliness
Favorite beer? Favorite pizza place? (this is a throwback to the original series)
Celebrator
Who is your favorite leader in business today?
Warren Buffett. He’s one of the few public figures I’d ever considered a role model. He makes business decisions based on value. He lives insanely below his means. He uses his wealth for good. The man really is one-of-a-kind.
Is there anything else you’d like to promote?
Um, sure. I can’t turn down an opportunity to pitch something.I’m about to start working as an associate at Atwood Financial Planning. Our business model is to be a fiduciary for our clients and provide personal financial planning advice for a very reasonable hourly rate. We have no affiliations with any financial institutions and clients pay neither commissions nor assets under management fees. If you (or someone you know) is looking for some financial guidance and don’t want to deal with a commissioned based salesmen or turn your assets over to be managed by an advisor, click here to read more about our process and then fill out this contact form to email me (Jason) directly and we can determine if we’d be a good fit. Thanks for the opportunity to share this Carl!
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That is one heck of a commute you’ve got there!
When I moved, I went from a 2 minute drive to a 50 minute drive. I thought I had it bad…!
I like this philosophical attitude! The post is really thought-provoking.
Not many people have the luxury of moving back in after college to pay off their student loans. Many people are on their own at 22, with 100k in student loan debt. If you are this latter group, its alright. Keep your head up, and fight through it one day at a time.