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Ill-Advised Landlords, Financial Nihilism, and Negotiating with AI ✍️
It's easy to be discouraged, but don't let impulse decisions derail your future!
Happy Tuesday, everyone!
Here’s a quick reminder that progress takes time.
Maybe you’re not loving your career, you’re working hard to pay down debt, or you feel behind on saving and investing goals. Instead of getting stuck in that mindset, focus on what you can control: building skills, staying consistent, and keeping those automatic contributions going.
Small steps still move you forward, and we’re here with you every step of the way. 🤝
HOME
Becoming a Landlord… by Accident?! 🤔

Some homeowners are ending up in a situation they never imagined: renting out their home because offers are smaller than they hoped. If you’ve already moved out and are expecting a quick sale, turning your house into a rental might seem like an easy way to keep the cash flowing. But think twice before you delist your home
As of last November, about 2.2% of rental listings on Zillow had previously been listed for sale. With a housing market that’s tilted in favor of buyers, more and more sellers feel like renting is their best option.
That might be true in some cases. But becoming a landlord comes with real tradeoffs.
Here’s the catch: once you rent it out, you’re officially a landlord, whether you planned for it or not… and that comes with more hands-on work than most people expect.
Why Being a Landlord Isn’t For Everyone
Renting your home might seem like passive income, but it isn’t. You’ll be in charge of:
🛠️ Repairs and Maintenance: From busted dishwashers, surprise plumbing issues, to costly HVAC updates… it will all be coming out of your pocket. It’s crucial to plan for those costs before listing your home for rent.
👬 Tenant Management: You don’t want anyone renting out your home. If you sell, that home is no longer your responsibility. But while you’re renting it out (while also hoping for a future sale), you’ll have to do your due diligence to find a good tenant — or be stuck chasing late rent and dealing with headaches.
📄 Legal Risks: You are liable for accidents that happen on your property, which isn't just a nightmare, but can also be a potentially expensive reality.
Even if the rent covers the mortgage, unexpected costs and constant stress can make it more damaging in the long run — both to your wallet and your mental health.
What to Consider Before Renting
Renting out your home shouldn’t be a reactive move of last resort. Renting should be something you’ve considered and planned for. First, think through:
🕑 Time and Effort: Managing tenants is hands-on. Don’t underestimate it, especially if you’re going to try to manage this property long-distance. You might even need to hire a property manager, which will reduce your cash flow.
💰 Financial Risk: It may seem financially savvy to rent your property, but repairs, vacancies, and management fees can quickly eat into profits. Selling for a slightly reduced price sounds a bit less crazy now, right!?
⚠️ Future Taxation: Selling your primary residence won’t create a tax burden. In fact, an MFJ couple can exclude $500k of capital gains from the sale of their home. But you lose that benefit if you wait too long to sell. All of those gains are subject to tax if you don’t hit the IRS’s 2-in-5 window.
📉 Alternatives: Before opting to rent, think about whether or not you want to be a landlord! If you’ve owned the home for a decent chunk of time, chances are it’s appreciated nicely. So, consider selling for less, even if your neighbor sold their similar home for a little more six months ago.
Renting out your home might sound like an easy win, but in reality, it comes with more headaches than you might expect. Before taking the plunge, make sure you (and your partner, if you’ve got one) weigh the pros and cons and the potential long-term risks.
INVESTING
Feeling Behind in Your Finances? 💰

There’s a growing trend, especially among younger generations, where money doesn’t feel… real anymore. Maybe it’s because we live in an increasingly digital world. But those numbers on a screen represent real dollars and potential financial freedom!
Instead of slow, steady investing, more and more people are turning to riskier bets and alternative options: meme coins, sports betting, options trading, etc. Anything that offers a shot at a quick win. Not because they don’t understand the risks, but because the traditional path to building wealth feels further out of reach than ever.
The emotional reality behind this behavior is “financial nihilism” — the belief that doing all the right things when it comes to your finances is no longer rewarded.
Why Financial Nihilism is On the Rise
It’s not coming out of nowhere. A lot of people, especially younger generations, feel like:
📚 Education is more expensive (and less of a guarantee).
💼 Entry-level jobs are harder to land.
🏠 Homeownership is borderline impossible.
And guess what, all of these things are true! Still, the nihilistic knee-jerk reaction only makes things worse, compounding financial problems. When you let YOLO vibes impact your spending and investing, those financial goals will only seem more improbable.
So when everything feels out of reach, it may seem like the only way to get ahead is to take a big swing. Because if the safe path doesn’t feel like it’s working, why not take a risky shot at something that might?
The Problem With Taking a Shot
Nihilism doesn’t just change the way you think about your finances; it changes how you act. And more often than not, it leads straight to speculation, often in the form of:
Gambling (on sports or current events you don’t know much about).
Putting your money in meme coins, thinking it will be “the next bitcoin.”
Taking bigger and bigger risks after small wins.
This is casino behavior, folks. But the house always wins. And while a few people may hit it big, most end up in a worse position. What starts as a harmless $5 bet can quickly turn into losses that are hard to recover from.
So, What Should You Do?
We’ll be honest… the slow path isn’t exciting, but it still works.
It’s okay to feel frustrated with the system. With rising prices, AI taking over jobs, and homeownership becoming a distant dream, we get why people may be looking for the fast track to wealth. Unfortunately, there still isn’t one (if you find one, let us know!).
The tried and true path still looks like this:
Consistently contributing to your 401(k) or other employer-sponsored retirement program.
Investing in low-cost index funds like it’s your job.
Letting compound returns work their magic on your behalf.
It may not be instant, but it works.
You don’t need a lottery ticket, a meme coin, or a 10-leg parlay to build wealth. You need consistency, patience, and a solid plan. 💪
TOGETHER WITH TURBOTAX*
How Solopreneurs Can Get Ahead of Tax Stress ✔️

For self-employed individuals and small business owners, one of the easiest ways to get ahead - and stop feeling behind - is to file taxes before April 15th. But recent tax law changes can add confusion, which is why TurboTax is here to help. Small business owners and sole proprietors will match you with a TurboTax Expert who will guide you through the process and even file for you today at turbotax.com/business.
Solopreneurs will be matched with business tax experts who specialize in your industry - helping you maximize deductions and feel confident your taxes are done right and on time.
How TurboTax Experts for Business Helps:
Save You Money: TurboTax Experts uncover deductions and savings, keeping more dollars in your business.
Access to Experts: Matched to your industry with an average of 12 years of experience, TurboTax Experts securely prepare and file your taxes - virtually or in person.
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Say goodbye to feeling behind on your finances by checking out TurboTax Experts for Business and get matched with a TurboTax Expert who will be by your side to handle your taxes and maximize your deductions.
BILLS
Using AI to Negotiate Medical Bills 🏥

AI isn’t just for writing emails or planning trips anymore. It’s quickly becoming a valuable tool in your financial toolkit…if you use it well.
Medical bills can be expensive and daunting. And they’re also some of the most complicated bills to understand: full of unfamiliar codes, doctors’ names you don’t remember seeing, and a bunch of medical jargon that feels like a foreign language.
All of this can make it overwhelming to deal with. It’s tempting to just pay it and move on. But when you’re slapped with a big ol’ bill, it’s definitely worth going through it line by line, and this is where AI can step in by:
Translating complex bills into plain English.
Researching different codes and fair pricing benchmarks.
Spotting duplicate or questionable charges.
Drafting emails or talking points for negotiations.
This is exactly what a NY-based marketing consultant did with Claude, lowering a medical bill his sister-in-law was ready to pay by $163k! Of course, AI can’t do it all for you. You still need to do additional research, handle the negotiations, and fill out more paperwork.
But AI can level the playing field by giving you the relevant information as well as the confidence to ask better questions and to push back when something doesn’t look right. Running your medical bill through your favorite AI could result in big savings.
Remember: you’re your biggest advocate! You can (and should) negotiate your bills when you’re able to. It might be uncomfortable at first, but the savings will be worth it!
ICYMI!
Your Weekly Update…
Pikachu Costs How Much?! 💸
A rare Pokémon card just sold for $16 million! Time to dust off your old boxes full of cards… your childhood collection may be hiding some value!
Chase Freedom Unlimited® Bonus 💳
One of our favorite no annual fee credit cards offers a $250 bonus when you spend $500 in your first 3 months. This is a limited-time offer. Learn more here!
Hold My Spot 💺
TSA workers are finally getting paid again, bringing relief to travelers. Still, some travelers are hiring “line-sitters” to hold their spot. A reminder that your time is money, and that there are always new ways to make extra cash out there!
Chocolate Thieves on the Loose 🍫
Another heist took place in Europe… but this time it wasn’t the crown jewels, just a slew of KitKats! Selling those for profit may become tougher than the thieves thought, as Nestle announces the stolen chocolate is trackable through their batch code.
A lot of your financial journey is outside your control. You can’t predict the stock market or time the housing market, but you can stick to the habits that put you in a strong position. Stay consistent with what works, and you’ll give yourself the best shot at long-term financial independence!
Best friends out! 🍻
