The Stacking Benjamins Show

Live from Joe's mom's basement (where receipts go to be judged and spreadsheets fear OG), this episode tackles two big questions Stackers are asking right now. What's the best tax software for filing your 2025 return? And what should normal, long term investors make of gold, silver, and crypto taking a wild ride?

Joe Saul-Sehy and OG are joined by Robert Farrington from The College Investor to break down the tax software landscape without the marketing fluff. Because if you're our Stacker avatar, you don't want hype. You want something that works, doesn't overcharge you, and doesn't suddenly upsell you because you clicked the wrong box.

Then in the headline segment, the crew digs into the sharp pullback in precious metals and crypto. Is this the beginning of something bigger? A buying opportunity? Or just another reminder that chasing shiny objects (literally shiny in gold's case) can make your portfolio feel like a roller coaster?

As always, Doug brings trivia, there's some basement banter, and the team separates smart strategy from financial fashion trends.

Choosing the Right Tax Software (Without Overpaying):

• Why FreeTaxUSA might be the best overall value for most Stackers

• When TurboTax or H&R Block make sense and when you're just paying for bells and whistles

• The pros and limitations of truly free options like Cash App Taxes and Chime

• Why TaxSlayer can be a solid choice for student loan borrowers, landlords, and side hustlers

• What investors and crypto traders need to know about brokerage imports and the new 1099-DA form

• Why filing taxes is mostly data entry and where real tax planning can make a difference

• Simple tools to track mileage, expenses, and side hustle income without losing your mind

Bottom line: the best software isn't universal. It's the one that fits your situation without surprise fees.

Gold, Silver, and Crypto: What the Drop Means:

• Why assets without earnings (like gold and many cryptocurrencies) can swing wildly

• The danger of investing based on FOMO instead of a plan

• How concentration risk increases the range of possible outcomes, both good and bad

• Why short term volatility doesn't automatically change a long term strategy

• The risks of misinformation, including AI generated financial advice that isn't real

OG walks through how disciplined investors think during volatile moments: zoom out, revisit your allocation, and stick to your strategy instead of reacting emotionally.

The Big Takeaway:

Whether you're picking tax software or deciding what to do during a market drop, the lesson is the same. Choose tools that fit your life. Build a plan before the chaos hits. Don't let headlines or shiny objects hijack your strategy.

This Episode Is For You If:

• You're trying to pick tax software without getting ripped off

• Markets are making you nervous and you're not sure if you should do something

• You want to understand what's happening with gold and crypto without the hype

• You're looking for calm, practical guidance during a chaotic time

• You believe steady wealth beats chasing shiny things

Let's Hear From You:

What tax software are you using this year and why? When markets get volatile, what helps you stay disciplined? Share your thoughts in the Spotify comments or The Basement Facebook group. Your experience might help another Stacker avoid an expensive mistake.

FULL SHOW NOTES: https://stackingbenjamins.com/the-best-tax-software-2026-robert-farrington-1805

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

Learn more about your ad choices. Visit podcastchoices.com/adchoices

Think building seven figure wealth requires exotic investments or perfect timing? This President's Day episode from Joe's mom's basement tells a very different story.

Joe Saul-Sehy, OG, and Neighbor Doug dig into a Kiplinger My First Million case study featuring a Wisconsin couple who started saving at age 32 with exactly zero invested and quietly built $2 million over the next 22 years using mostly retirement accounts and steady habits. Their success sparks a bigger conversation about why simple strategies often outperform complicated ones, and how surviving the boring middle is where wealth is created.

Along the way, the gang tackles advisor fees, the psychology of enough, long term care decisions, and the real value financial professionals can bring. Of course, it wouldn't be a basement episode without trivia, community wins, and a few unexpected detours (including a conversation about giant toilet paper rolls that somehow reinforces the episode's central theme).

What You'll Take Away:

• Why ordinary retirement accounts (401(k)s, SEP IRAs, and Roth IRAs) can be enough to build significant wealth without chasing complex investments

• How starting with just enough to earn the employer match creates momentum without overwhelming new savers

• A simple escalation strategy: increasing contributions by 1% each year to grow savings almost painlessly

• The often missed detail of contributing through the final paycheck to capture the full employer match

• A creative gamification approach to Roth contributions tied to the Social Security wage base

• How reframing long goals into months instead of years helps investors stay motivated during the long, quiet middle stretch

• Why imperfect plans with higher fees can still beat waiting for the perfect investing setup

• The real concerns people have about trusting workplace retirement plans and how those plans actually function

• Lessons the featured couple learned, including the value of post tax flexibility later in life

• Long term care planning as risk management, including balancing insurance coverage with self funding strategies

Big Behavioral Conversations:

• A TikTok minute featuring Dr. John Delony sparks a discussion about defining enough and whether chasing more success is driven by purpose or ego

• How redefining success can shift financial decisions more than any spreadsheet ever will

• The danger of constantly moving financial goalposts once progress begins

Listener Mailbag: When Is a 1% Advisor Fee Worth It?

OG walks through how to evaluate an advisor relationship beyond performance numbers, including whether your advisor helps you make money or avoid costly mistakes, the value of saved time and reduced stress, planning continuity for spouses or heirs, typical fee structures, and how to have an honest fee conversation without damaging a long standing relationship.

This Episode Is For You If:

• You're behind on saving and worried you've missed your window

• You feel like wealth building requires strategies you don't understand

• You want proof that simple plans work if you stick with them

• You're wondering if your advisor's fee is worth it or if you should manage it yourself

• You need reassurance that boring and consistent beats exciting and complicated

This episode is a reminder that wealth rarely comes from brilliance or shortcuts. More often, it comes from steady decisions repeated consistently while everyone else searches for something more exciting.

FULL SHOW NOTES: https://stackingbenjamins.com/how-to-make-a-million-after-starting-late-1804

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

Learn more about your ad choices. Visit podcastchoices.com/adchoices

Nothing says romance like a heated debate about the 4% rule.

Live from the basement (which suspiciously resembles YouTube headquarters), Joe Saul-Sehy, OG, Neighbor Doug, and the panel celebrate Valentine's Day weekend the only way Stackers know how: by putting their favorite financial ideas on the hot seat.

This isn't a polite discussion. It's a rapid fire "love it or leave it" showdown where popular money strategies either get roses or get shown the door.

On the chopping block:

Paying off a low interest mortgage early: financial freedom or opportunity cost disaster?

The FIRE movement: empowering clarity or accidental misery?

Lifestyle inflation: natural evolution or silent wealth killer?

Real estate as passive income: dream scenario or second job in disguise?

The 4% rule: reliable rule of thumb or outdated security blanket?

Budgeting apps: behavior changer or digital guilt machine?

Expect strong opinions. Expect pushback. Expect OG to bring spreadsheets to a knife fight. Expect Doug to stir the pot. And expect at least one take that makes you argue out loud in your car.

Along the way, the crew swaps Valentine's Day plans, reviews survey results from listeners, and throws down in a trivia challenge that could shake up the leaderboard. With margin call rules in play, nobody's position is safe.

What You'll Discover:

Which popular financial strategies hold up under scrutiny and which ones deserve a breakup

Why smart people disagree about mortgage payoff strategies

Whether the FIRE movement creates freedom or just different problems

The truth about lifestyle inflation and when it's okay versus when it's dangerous

Why real estate investing is rarely as passive as it sounds

Whether the 4% rule still works or needs serious revision

If budgeting apps actually help or just make you feel guilty

How to question your own financial assumptions without second guessing everything

This Episode Is For You If:

You want to understand WHY you believe what you believe about money

You're tired of one-size-fits-all financial advice

You enjoy hearing smart people debate and disagree respectfully

You've been following certain money rules without questioning if they fit YOUR life

You believe the most loving thing you can do for your financial plan is challenge it

This episode is for anyone who doesn't just want answers but wants to understand the thinking behind them. Because sometimes the most loving thing you can do for your financial plan is break up with strategies that aren't serving you anymore.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

What's more romantic than roses and chocolate? How about not fighting about money.

Joe Saul-Sehy and OG welcome Douglas and Heather Boneparth, the financial planning power couple who literally wrote the book on navigating money in relationships. Broadcasting from the basement (where love is patient and spreadsheets are kind), the crew dives into how people can build financial trust, avoid money secrets, and actually enjoy talking about dollars without it turning into a heavyweight title fight.

Whether you're navigating finances with a romantic partner, a roommate splitting rent, an accountability partner keeping you honest, or a family member you're in business with, these principles apply. Because let's face it: our Stacker avatar isn't trying to impress Wall Street. You're trying to build a great life with the people who matter, without money becoming the thing that creates tension.

Douglas and Heather break down what healthy financial communication really looks like, how to spot and prevent financial secrecy, and why shared goals matter more than perfectly matched spending styles. They also tackle the tricky stuff: different money upbringings, emotional baggage around finances, and how to reset when conversations go sideways.

And since this is the basement, you'll also get practical reminders about key financial deadlines (because nothing kills momentum like IRS penalties), smart ways to teach kids about money, and Doug's festive trivia to keep things light.

What You'll Learn:

How to talk about money without it escalating into a debate or argument

The warning signs of financial secrecy and how to prevent it in any relationship

Why shared goals matter more than identical personalities or spending styles

Practical ways to align spending, saving, and investing with another person

How your childhood money experiences shape your adult financial behavior

Smart ways to teach kids patience, work reward connections, and intentional spending

Important financial deadlines to keep on your radar

Why communication, not math, is often the real key to financial success

This Episode Is For You If:

You avoid money conversations because they always seem to go badly

You're navigating shared finances with a partner, roommate, or family member

You want to align financial goals with someone without constant friction

You're single but have accountability partners or friends you talk money with

You believe better communication is the key to better financial outcomes

Question for You:

What's one money conversation that felt awkward at first but ultimately made a relationship (romantic, friendship, or otherwise) stronger? Drop your answer in the Spotify comments or the Stacking Benjamins Facebook group. You might just help another Stacker start a better conversation.

Because in the end, mastering money isn't just about returns. It's about building a life and relationships that work.

FULL SHOW NOTES: https://stackingbenjamins.com/relationships-and-money-with-doug-and-heather-boneparth-1802

Learn more about your ad choices. Visit podcastchoices.com/adchoices

Joe Saul-Sehy, OG, and Neighbor Doug pull up a rickety basement chair and unpack a growing trend: people treating investing like a series of high stakes bets instead of a long term plan. Sparked by a recent Wall Street Journal piece on aggressive investing, the gang digs into where the line is between smart risk taking and straight up gambling with your future.

Using plenty of real world examples and a few basement metaphors, the crew breaks down how stocks, businesses, options, and even so-called innovative products can fall into very different categories depending on why you're using them. The key theme? Good investing isn't about being bold. It's about understanding probabilities, controlling what you can, and stacking the odds in your favor over time.

Along the way, the team also tackles listener questions, including some strong feelings about Costco (because of course), and shines a flashlight into the dark corners of complex products like Indexed Universal Life insurance, explaining why "sounds sophisticated" doesn't always mean "fits your plan."

If markets feel noisy, confusing, or a little unhinged right now, this episode is your reminder that boring, disciplined strategies still win, and that you don't need to bet the farm to build one.

What You'll Learn:

• Why so many investors are confusing betting with investing right now

• How to tell the difference between calculated risk and speculation

• Why understanding probability matters more than chasing big wins

• Where options, businesses, and alternative investments can fit and where they often don't

• The hidden risks behind complex products like Indexed Universal Life (IUL) policies

• Why compounding beats hype even when headlines say otherwise

• How small, consistent decisions quietly outperform flashy moves

• Yes, what Costco has to do with smart money choices

This Episode Is For You If:

• Markets feel confusing and you're not sure if you're investing or just guessing

• You've been tempted by strategies that sound sophisticated but feel risky

• You want to understand the line between smart risk and gambling

• You're tired of flashy investment advice and want clarity on what actually works

• You need reassurance that boring, disciplined strategies still win

Question for You:

What's the riskiest financial move you've ever considered, and what stopped you (or didn't)? Share your answer in the Spotify comments or the Stacking Benjamins Facebook group. Bonus points if hindsight made you laugh or wince.

Learn more about your ad choices. Visit podcastchoices.com/adchoices