BiggerPockets Money

Natalie Kolodij is a tax strategist. (You’ve probably seen her in the forums!) With April 15 looming around the corner, we’re going to chat about ways to choose the RIGHT tax professional who can best serve YOUR specific needs.

Natalie also shares a few red flags about potential tax preparers, as well as specific things your tax pro should be asking for—and what it means if they do not.

She’ll also share some common missed deductions that can cost you BIG and how to prepare and organize your documents so your tax pro can process your returns quickly, efficiently, and with the least amount of time billed to you.

Looking for that seemingly-elusive real estate professional status? Natalie explains in detail how to qualify for this lucrative benefit. She even shares how long you can depreciate a kangaroo!

If you’re a taxpayer, this show can help you save time and money. If you’re a real estate investor/taxpayer, you can’t afford NOT to listen to Natalie’s advice!

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On episode 110, we interviewed A Purple Life. As she was sharing her story of financial independence, she casually mentioned that her mother didn’t start investing until later in life, and STILL managed to retire at age 55!

So this week, we’re talking to her mother - who has her own amazing story of early retirement which she was able to accomplish even though she didn’t START investing until she was 40!

Momma Purple shares her pragmatic approach to money in general - buying what you need, trying to make repairs instead of buying something new, sticking to a budget and banking bonuses instead of spending them.

Momma Purple is also a big advocate for having multiple, passive income streams like rental properties and a pension.

Hear her story of weathering TWO market crashes during her investing journey, taking immediate action when she discovered her money was in the wrong investment, and how fabulous her life is now, after retirement.

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Purple graduated from college and got a job in New York City making $35,000 a year. And spending $35,000 a year. Her net worth was a whopping $5,000. Her partner shared the concept of financial independence with her, but she wasn’t interested.

Two years later, her net worth had grown considerably, but she was still not tracking her spending or paying attention to much of her finances.

So, she took a good look at her money situation and discovered that there were places she could make cuts—yet not really feel them.

She moved across the country, she changed jobs, she asked for raises. And she saved and invested her money.

And her net worth grew to the point that she is retiring before the end of the year and traveling the world—all because she looked at her financial situation and said, “I can do better than that!”

Listen in to hear just how she increased her income and decreased her spending to craft the life she wanted!

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This week, we sit down and talk with Airman Mildollar, from Military Dollar.

(Spoiler Alert: Despite the name, Airman Mildollar is a woman!)

Airman Mildollar shares her story of college debt, car loans and rapid payoff to start building her wealth to become financially free, despite not being married, having kids or working in tech. In fact, she’s an officer in the Air Force.

She shares her systematic goal setting and goal reaching strategy that allowed her to pay off her debt ahead of schedule - including stretching her military benefits to cover more than just food or housing.

She started reading finance blogs and books and starting putting money away. Moving in with a friend reduced her rent payment, and she began investing in a Roth IRA, opened up a TSP (Military version of a 401k) and also invested in individual stocks in after-tax accounts, saving about 20% of her pay.

Every time she received a raise, she committed to put at least 50% of that raise into her investments.

In 2011, she bought a rental house as she was deploying, put tenants in place and then went overseas for one year, returned home and bought another property for herself to live in. Originally intending to live there for a year then rent it out, she ended up staying for two years then selling to realize HUGE tax-free gains.

2013 is when her Financial Independence journey really hit its stride as she read Your Money or Your Life, and she took a much closer look at her budget, finding another thousand dollars to put into her investing.

MilDollar shows that you CAN become financially independent on your own, without working in an ultra-high-paying job, when you diligently pursue your goal.

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Kristi Tanner Smith considers herself privileged—she was an only child in a big house with lots of toys. But Kristi’s mom was diagnosed with a fatal disease and given six months to live when Kristi was five. While her mom did beat that estimate, she ultimately lost her battle when Kristi was 12.

During her mom's final years, she tried to teach Kristi about money: "Save up and pay cash for purchases. Be responsible with your finances."

Her father was the opposite. So Kristi was able to see both sides of the coin and recognize that being responsible was the better way to go.

Kristi lost her father to a freak accident in 10th grade, and she used the insurance settlement to pay for college, where she studied Criminal Justice. Kristi’s husband worked at Nike; they paid for his entire college tuition once he went full-time with the company.

(Pro tip: If you need your college tuition paid for, look for a company that offers tuition reimbursement!)

After college, she took a job in the Probation Office. She didn’t like it. To make matters worse, on her honeymoon, she discovered they were looking to replace her!

She knew she didn’t want to be dependent on someone else for money, so she turned to real estate. She discovered BiggerPockets, ChooseFI, and the concept of financial independence—this became her new focus.

She started with the home she inherited from her mother, then bought a home from the MLS, followed by a primary residence, then another MLS purchase, and a cabin in the mountains.

Her cash flow on these few properties covers her monthly living expenses, freeing her to pursue her passions. Because when you take care of the money part, you can pursue your dreams and live the life you TRULY want!

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Financial Panther (Kevin) went to law school, graduated from law school, and took a job as an attorney. Attorneys make a lot of money, right?

So, with all this income potential, why is he doing side hustles that pay him significantly less? Happiness.

Being an attorney didn’t make Kevin happy. In fact, it made him decidedly unhappy. He changed jobs several times but in the end decided being a lawyer simply wasn’t for him. So, he left the field to pursue fun things that he liked doing.

Kevin loves to be outside. He lives near a university in a large city. He loves dogs. Put that all into a shaker, and out comes Kevin 2.0.

Kevin 2.0 takes dogs for walks during lunchtime. He gets out of his downtown office (he makes himself go to a co-working space so he accomplishes things every day) and delivers meals to office workers who can’t get away.

Kevin walks dogs around the downtown area for their owners who can’t get away at lunchtime to take them out. Kevin charges scooters overnight, and on his way home, he delivers even more meals.

Best of all? Kevin gets to spend time outside almost every single day. He does what he CHOOSES to do, regardless of what it pays.

Financial freedom isn’t about quitting your job. It's about living your best life, which Kevin 2.0 is now doing.

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Megan Gorman started learning about money very early – at age 5 she begged her parents for a Little House on the Prairie Dress. Her parents said we’re not buying it for you, but you can save up for it yourself. 18 months later, she was the proud owner of a new dress – and a bonus bonnet from her parents who were so proud of her for saving up and being so determined.

Fast forward to high school, and she got a job at a vacation resort during the summer high season. Her father made it clear she was to save some of her earnings to contribute to her college tuition, and she was able to save $5,000 a summer. Her experiences with money were empowering up through college, but she ended up with credit card debt and eventually had to negotiate with the banks on a payoff.

She took a year off between college and law school, choosing a state law school to keep her costs low. Megan graduated from law school, got a job, and had to navigate adulting – getting an apartment, buying a work wardrobe, starting her adult life on very little funds, again trying to not incur more debt after having so recently paid off her credit cards. 

Megan’s student loan story is different from others we’ve heard on the Money podcast – while she aggressively paid down her private loans, Megan actively chooses NOT to pay off her public loans because they have such a low interest rate. She feels she can make a better return in the S&P 500, so she leverages her debt and is comfortable with her decision. However, Megan readily admits this strategy is NOT for everyone, and you definitely need to be comfortable with the decision to continue to carry debt. Once her private debt was paid off, she started investing in a Roth IRA and 401k to grow her assets.

And because she’s from Generation X, Megan bought a house when she got a HUGE promotion. She watched the value of her home soar, then sold to move to California. She bought in 2007 in CA, and watched that price drop, then rise again. Location location location.

Megan now advises high net worth and ultra-high net worth individuals manage their money, because no matter how much money you make, everyone struggles with expenses.

And today, Megan shares excellent advice with us for strategically thinking about our money for the present as well as planning for the future.

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Jen Hemphill was born in Colombia and lived there for the first eight years of her life. The economy was really bad, and her earliest memories were of a scary time when her educated father did whatever he had to do to make money.

Her redheaded dad stood out in Colombia, and it wasn’t a safe place for him to be. So, they moved to the U.S. Jen remembers being embarrassed for not having money, knowing her friends had it.

She attended the same college where her mother was a professor. Discounted tuition coupled with scholarships and a bit of parental help allowed her to graduate with no debt. She bought a car, paid it off quickly, and felt very proud of herself for doing so.

Then, she met and married her husband. They took 15 years to pay off his $40,000 in student loan debt. She thought they were doing great, but a deeper look at their finances about 10 years in revealed a huge mess.

Thinking back to her childhood, she realized she needed to make big changes in order to get ahead. Her family went on a budget, cutting out all unnecessary spending to focus on paying off the debt. Jen uses a series of labeled bank accounts to ensure they stick to their budget and now saves for purchases rather than raiding the emergency fund to pay for things.

Jen took what she learned and became an Accredited Financial Counselor, knowing that there are so many others who need to be pointed in the correct direction. She calls herself a Money Confidence Coach, because when you have confidence in your money management skills, you can tackle any problem.

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Lauren and Steven met in high school and attended the same college. After undergrad, Steven was accepted into the Ph.D. program at UC Irvine. During the first year, he decided he didn’t really want a Ph.D. in Physics, but he really enjoyed working with students.

They moved back to Florida so Steven could get his master’s in Education, while Lauren worked her first “real” job.

But after two years, they were burned out from working full-time. After learning about financial independence and achieving an incredible savings rate—to the tune of $100K in two years—they decided to take a break.

Their “break” was a six-month trip to Hawaii, paid for up front by their big savings account—but repaid by a series of side hustles in Hawaii. While most people spend lavishly to go on a tropical vacation for one week, they ended up $1,000 positive while spending six months there.

Re-energized, they returned to Florida for a full-time job for Lauren and a continuing tutoring job for Steven—making more money than before they left for Hawaii. Increased income meant increased savings rate for these two, having lowered their expenses by purchasing a three-bedroom condo, periodically renting out an unneeded bedroom.

But after about three years, they felt burned out again. This time their “break” was a trip around the country to visit every national park—all 61 of them—in seven months. Again, they wanted to pay for the trip with income generated during the trip.

They cut expenses by buying a compact cargo van and sleeping in it for the majority of the trip. They continued working about 10 hours a week during the trip, rented their condo for seven months, and hit the road.

Each time they return from their mini-retirements, they are refreshed, re-energized, and ready to jump back into work with both feet. Their end goal isn’t early, permanent retirement, but several small mini-retirements to enjoy their journey.

In This Episode We Cover:

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J Money wasn’t necessarily BAD with money, but his first home purchase - made because everyone else was doing it - prompted him to seek out advice about money.

He stumbled upon the blogging world and was enthralled with the transparency. Here were real people talking about real issues they were facing - similar to what he was going through himself.

He started his own blog called BudgetsAreSexy, and soon was approached by someone who wanted to buy an ad on the site. A new source of income generation!

His blog success brought attention from national news sites, and traffic grew exponentially once they started sharing his articles. But as traffic grew, so did his time commitment. 

As he became more entrenched in the blogging space, he discovered that people buy and sell blogs - so he started flipping web sites. Another source of income generation.

When it came time to choose between his full time job and his side hustle, he discovered the decision was made for him when he was called into his manager’s office and let go. (The company later went out of business.)

Thrust into entrepreneurship, J buckled down with his spending, and discovered that Budgets really ARE sexy, and they can be the key to your financial success.

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