039: Travel in Style with Freelancer and Credit Card Expert Jason Steele

Jason Steele is an expert on credit cards and awards travel. He writes for several of the top personal finance websites including PTMoney.com, and his work is syndicated to mainstream publications.

Jason has launched the CardCon conference. Find out more at CardConExpo.com.

So let’s dig in. Let’s meet today’s Master of Money.

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I hope you enjoyed that. A big thank you to Jason for giving us the gold today.

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Today’s guest has traveled all over the world, along with his wife and children, for free. This has allowed his family to travel much more than they would be able to if they had to pay for air travel. Jason Steele is a credit card and reward travel expert and is here today to share all of his secrets with us.

Focusing on the Big Picture

Jason always tries to look at the big picture. In every area of finance, he sees people focusing on the small things. When it comes to credit, Jason likes to tell people to just pay their bills on time and don’t carry any debt and if you do those things, it’s almost impossible to not have good credit. Sweating the small details may be important in other aspects of your life, but not in finance.

Jason talks about the “big things” for his family, like saving for a new house or paying off student loans. Jason’s philosophy is to minimize recurring expenses while being more lenient with one-time expenses. Cable TV and buying gas for the car every week are the type of recurring expenses that Jason tries to avoid.

Jason credits his parents with his “big picture” mindset. They were all about personal finance, even before “personal finance” was a term. For example, his dad drove an older car so that the family could afford to do fun things together. His parents taught him to make choices to deny himself in the present in order to achieve long-term stability.

Become a Fan of Personal Finance

Jason says you have to become a fan of personal finance in order to truly learn it. Find an author, blogger or podcaster that you really enjoy and learn all you can.

Jason remembers dropping his daughter off at school one day, and a lady asked him what he did and when he told her, she said, “Oh, I’m a huge fan of personal finance websites.” For Jason, it was a cool experience to meet someone in the real world who listens to and loves bloggers that he knows personally.

From Dependent to Independent

Jason wasn’t always independent, but the transition wasn’t too difficult once he moved out of his parents home.They taught him to use credit cards by giving him one of theirs, with strict instructions on when and how he was to use it.

In college, Jason applied for his own credit card and his parents provided instruction on how to pay it off every month so as not to accrue interest. At the time, the constant oversight frustrated him, but now he is appreciative of their efforts to keep him out of debt. The only disadvantage of this system is that now he can’t write a really great book about how he got out of debt!

Jason’s parents wanted him to realize that you can’t just swipe a magical card and not be held accountable for it.

Becoming a Homeowner at Age 22

Jason became a homeowner at the age of 22. He was coming out of college and looking for a place to rent and a roommate. The roommate and the house never seemed to line up at the same time. After a year of living in his parents’ house, they were moving and so Jason realized he was either going to have to rent or buy a house.

Thankfully real estate prices were low back in 1995 in Atlanta and he was able to put $3,000 down on a $70,000 house. Through an ad, he found a roommate who could help pay the mortgage. That’s a time that Jason looks back on fondly and that roommate is still one of his best friends.

How does a 22-year-old, with no credit score, buy a house with only $3,000 down?

Jason had been an authorized user on his parents’ credit card for at least 5 years, he had paid all his bills on time and he’d had his own credit card for several years. For this reason, Jason is a strong believer in graduating from college with at least some credit experience.

Avoiding Student Loan Debt

Jason’s parents created a deal with him. They would pay for his college if he paid it forward by paying for his kids’ college. They didn’t want his kids saddled with student debt if he wasn’t. Jason said he’s hoping to be able to give his kids the same “leg up” that his parents gave to him. His parents didn’t write him a blank check. They kept a tight rein on the spending. At this point, he hasn’t started his kids’ college funds but believes he still has plenty of time to make that happen.

From Old House to Dream House

Jason lived in his first house in Atlanta for about two years. His dream was to move to Colorado and so he rented out his house in Atlanta while getting settled in Colorado. After a year, he sold the Atlanta house and bought a loft in downtown Denver. He was living there when he met his wife and shortly after they got married, they sold the loft and moved into a house a few miles outside of downtown Denver.

Jason’s parents explained to him how they used the equity in a home they owned, combined with savings, to purchase a nicer home. Jason and his wife bought the house outside of Denver and restored it, but eventually tired of some of the frustrations of living in an old house. Last year they moved into a newer house that was built in 2014. They love the house they’re in, but the end goal is to build their dream house in the neighborhood.

They’ve built up equity and added savings in each home along the way. It’s a path that his parents showed him and that he’s tried to follow.

Jason comes from 3 generations of real estate agents, starting with his grandmother, so it really is a family affair. But when it came to selling his loft in downtown Denver, he was able to sell it using a flat e-listing. He entertained a dozen potential buyers and then sold it without paying commission. With his last home, he did use a traditional broker. Working as a freelancer, any missed hour of work is money lost, so Jason was glad to have a real estate agent to help him with finding his last home.

When Jason and his wife get ready to build their dream home, he intends to look for the property himself using tips that a real estate friend shared with him to find properties that aren’t listed on the market.

The ultimate lesson here is that home ownership is a lot more approachable than you might think. He didn’t really take his parents seriously at first when they told him to buy his own house. It seemed unattainable and he was nervous about making the monthly payments, but because they reviewed the numbers well, he had good credit, and the government offered first time home buyers assistance, he was able to make it happen.

Becoming a Personal Finance Writer

Jason grew up in a healthy financial household and he now writes about credit cards and travel. Not only is he a student of healthy finances but now he’s helping others.

Since personal finance was his family’s thing, it was natural for him to begin writing about it. Of course, the beauty of blogging is that you can write from inexperience. “How I Learned to Do…” whatever it is. As a blogger, Jason writes hundreds of articles every year. He chooses his topics based on things he already knows, research he’s done, and new ideas he encounters. Digging through those new ideas is one of his favorite things to do.

Making a Priority of Investing

The one area of personal finance that Jason is just not good at is investing. He says there’s no way around the fact, no matter how much he tries to rationalize it. When his wife was in grad school, he would pay for her tuition in cash because it seemed like a good investment. She became a pharmacist, which is a good paying job. He views his kids’ college funds as a good investment. And even his dream home. But he says he definitely needs to dive into the fine print and figure out how investment really works.

Jason has simply prioritized other things. He hasn’t actively managed his 401k’s and knows he needs to work on that. He also talks about diversifying and just spending a few minutes a month looking at what’s going on with his investments.

Jason’s traditional career, with 401k access, only spanned a period of 17 years. After graduating from college in 1994, he held a series of jobs, some of which offered 401k’s. He began freelancing full-time in 2011, so it’s been just over 5 years since his last 401k ended.

Using Mortgage Debt to Pay Off Student Loans

Purchasing multiple homes, each in a higher price bracket, is one of Jason’s proudest financial achievements. Paying off his wife’s high-interest school loans would be another. When she graduated, about 2 or 3 years ago, she had $180,000 in student loans at 8%. For someone who has never had credit card debt in his life, this number was unimaginable. It was working out to be $800-1,000 in interest alone every month. Jason was determined to pay it off as quickly as

One way that they did this was by borrowing the maximum amount possible when they bought their new home at just under 3% interest. It was a no-brainer to borrow at 3% to pay towards 8%. After that, Jason paid off every bit he could by making multiple payments a month, postponing other purchases, and even using a credit card with 0% interest to pay towards it.

How to Travel, as a Family, for Free

I mentioned at the beginning of this episode that Jason is a travel hacker; that means he uses credit card points and accumulated miles to travel for free.

Jason travels often…like, every month often. And nearly half of that time, his family of 5 travels together. The difference for Jason is that he spends no money on this travel. He uses points for everything. He attended my conference, FinCon, in San Diego with not only his wife and 3 kids but even his in-laws.

In October of 2017, Jason and his family will travel to Israel completely free, and not only free but with all of them in Business class. This is a $20K trip for the tickets alone. In the first 9 months of 2017, his entire family flew domestically three times, costing nearly $6K total, but Jason never came off a single penny.

If your interest is peaked and you want to know more about traveling for free, be sure to check out Jason’s articles on The Points Guy’s site. You can also go to My Bank Tracker and scroll to the bottom of the page and sign up to receive Jason’s free ebook that he wrote on this topic. Jason has also contributed several articles to my own website which you can access by going to PT Money.

Getting Your Dream Home with Less Hassle

So what are Jason’s goals now? He mentioned retirement and his dream home earlier. The house that they’re hoping to build is close to 4000-5000 square feet with a basement. Their plan is to purchase a small, outdated home in the neighborhood, buy it, and rent it out for a year while he and his wife meet with architects and get all the right permits to remodel and upgrade it to get the house they want. It’ll be easier to get a loan for a lower priced rental home, and then continue to save money towards a construction loan and then the home mortgage.

Jason’s wife has worked in some pharmacies but for the last 8 months has been home with their newborn son. She really loves being a stay-at-home mom and as long as she loves it, Jason wants her to keep doing it. Whenever she’s ready, she can jump back into a pharmacy.

Jason is super content with his career and the fact that they aren’t dependent on his wife’s career or just barely getting by on his income. They’re doing well and he feels that it’s a gift to his wife for her to be able to stay home with no worry about their income.

Layoffs, Blizzards, and Babies

Looking back, Jason feels great. There were some bad times, like when they bought that really old house and spent $6-70K to fix it up. At the time, he was working in computers as a contractor. IN a very short time after finishing the house, he found out he was laid off, and then his wife came home and told him she was pregnant.

They had been counting on his income and now they were down to zero. And with a baby on the way.

Two really dramatic blizzards weren’t making it an ideal time to go try and find a job. Jason thought they might have to sell their house and move into a less than desirable apartment. But he got a contract job for a few weeks in January and by February he was working a decent job with Boeing.

His last full-time job was a contractor of the federal government. They dug out of the pit and made it work. Now they can look back and laugh. After getting laid off from the federal government job, Jason really started pursuing his freelancing. The beauty of freelancing is that it allows you to make more and more money each month.

Show Notes

Time Stamp

  • 01:20 How looking at the big picture has helped Jason to win in his personal finances
  • 03:00 How Jason manages to not buy gas for his car to reduce recurring expenses
  • 04:20 Who was the inspiration behind Jason’s “big picture” style?
  • 08:55 Ensuring a smooth transition from dependent to independent
  • 12:35 Becoming a homeowner at the ripe old age of 22
  • 15:25 The deal Jason’s parents made that kept him and his children out of student loan debt
  • 17:40 Using equity and savings to go from old house to dream house
  • 20:40 When to use a traditional real estate broker and when to do it yourself
  • 24:17 Choosing topics for hundreds of blog posts per year
  • 27:40 Investing in college tuition, college funds, and real estate
  • 30:40 Why Jason took out a larger mortgage than he needed
  • 36:50 Traveling to Israel as a family of 5, in Business class, for free
  • 42:00 How a guy, who has admitted to not saving for his kids’ college, plans to retire early
  • 47:30 How a lay-off, a baby, and two blizzards got Jason to his current freelance life

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This show is part of the FinCon Podcast Network and was produced by Steve Stewart.

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One Comment

  1. Avatar Oliver @ Appreneurinvestor.com says:

    I have to listen to this over and over so I can spread the word to my clients who frequently travel using their cards. CardCon also got my attention here.

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