The Stacking Benjamins Show

Ever feel like your money questions don't fit neatly into one category? One minute you're thinking about retirement, the next it's insurance, emergency funds, gifting money, or whether your workplace plan is helping or hurting you.

This is one of those episodes where Stackers bring the real-life questions, and Joe Saul-Sehy, CFP Anna Allem, and Neighbor Doug help sort through the noise. It's a true Q&A show built from the issues you're wrestling with right now. No perfect spreadsheets. No one-size-fits-all answers. Just practical guidance for making smart decisions when your financial life has a lot of moving parts.

You'll hear how to prioritize when everything feels important, how to adjust your strategy as rules change, and how to stay flexible without losing control of your long-term plan. College planning comes up, but it's part of a bigger conversation about balancing competing goals, not the center of the episode.

What You'll Learn:

• How to make better decisions when multiple financial priorities collide

• Smarter ways to think about life insurance when cash flow feels tight

• How to build or rebuild an emergency fund with inconsistent income

• What changes to 401(k) rules could mean for your saving and investing strategy

• When opting out of a workplace plan might make sense, and when it's a mistake

• How automatic enrollment and contribution changes can impact your future wealth

• The right way to gift money to kids or grandkids without creating tax or planning problems

• How HSAs fit into your bigger financial picture

• Why financial gridlock happens and how to break through it

• How to balance short term flexibility with long term security

• A clear explanation of FAFSA and financial aid, and how it fits into overall planning for families who need it

This Episode Is For You If:

• You're juggling multiple financial priorities and not sure which one to tackle first

• You feel stuck because everything seems important and nothing feels urgent enough

• You want guidance that fits your messy real life, not just textbook answers

• You're tired of financial advice that assumes you only have one problem at a time

• You need permission to prioritize imperfectly and still make progress

If your finances feel like a maze, this is your map.

FULL SHOW NOTES: https://stackingbenjamins.com/answering-stacker-questions-with-anna-allem-1792

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

Enjoy!

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Some people kick off a new year with a vision board. We prefer a runway show in sweatpants from Joe's mom's basement.

Joe Saul-Sehy, OG, and Neighbor Doug throw personal finance into the spotlight and ask the question every Stacker secretly loves: What's officially "so last year" in your money plan, and what's worth keeping for 2026?

Because here's the truth. You don't need a total financial makeover. You need a few smart "wardrobe swaps" that fit your real life. The habits that quietly drain your progress (hello, lifestyle creep). The stuff people obsess over that doesn't matter as much as they think. And the overlooked moves that make everything else easier.

The crew breaks down what's out (financial habits that looked good but never delivered), what's in (the practical moves that reduce stress and create actual progress), and why real financial planning isn't just about investments but about building a system that holds up when life gets messy.

Also on the docket: a fresh start to the yearlong trivia competition with new rules, new twists, and the kind of competitive energy that makes you wonder if the trophy comes with a safety warning label.

What You'll Learn:

• What financial trends are out for 2026 and why they weren't helping anyway

• The habits that are in if you want more freedom, less stress, and fewer "where did my money go" moments

• Why real financial planning isn't just investments but a system that works in real life

• How lifestyle creep sneaks in and a couple ways to stop it before it becomes your full-time hobby

• What tax strategy means for normal people, not just spreadsheet enthusiasts

• The money conversations you should have early in the year before life gets loud again

• A realistic take on housing in 2026 and what to focus on when markets don't behave

• New trivia rules including a twist that changes everything if you're not paying attention

This Episode Is For You If:

• You want to know what to stop doing so you can focus on what works

• You're tired of financial advice that adds more tasks instead of clarity

• You suspect some of your money habits aren't pulling their weight

• You want permission to quit the financial trends that never fit your life

• You're ready for a few strategic changes that make 2026 feel more manageable

Questions to Think About:

What's one money habit you're officially retiring in 2026? If you could upgrade one part of your financial plan this year, what would it be: spending, saving, investing, insurance, or taxes? Drop your answers in the comments or the Basement Facebook group because this episode is all about figuring out what stays and what goes.

FULL SHOW NOTES: https://stackingbenjamins.com/finance-hot-or-not-2026-1791

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

Enjoy!

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If you're making decent money but still feel like you're one bad month away from stress, this episode is for you.

Joe Saul-Sehy, OG, and Neighbor Doug sit down with Mel Abraham to talk about something most Stackers think about but don't know how to start: creating income that doesn't depend entirely on showing up to work every single day. Not side hustle mania or get-rich-quick schemes. Just practical ways to build what Mel calls a "money engine" that makes your financial life steadier and way less stressful.

Mel breaks down the different types of income streams, how they fit into real life (not just theory), and where to start if you're tired of feeling like your paycheck is the only thing keeping everything afloat. The goal isn't to quit your job tomorrow. It's to create options and breathing room so one surprise expense or career hiccup doesn't derail everything you've built.

Then Joe and OG tackle the January financial to-do lists that flood your inbox every year. You know the ones: "15 money moves to make before February!" They separate what's worth your time from what's just financial busywork designed to make you feel productive without moving the needle.

Because here's the truth. You don't need more financial homework. You need a few strategic moves that make 2026 feel more manageable from the start.

What You'll Walk Away With:

• How to think about building income beyond your paycheck without burning out

• The different types of income streams and which ones fit your actual life right now

• Where to start creating assets that work even when you're not clocking in

• Which January money tasks are worth doing and which ones waste your time

• How to prioritize your financial checklist for maximum impact with minimum stress

• Simple ways to organize your money for the year without it becoming a second job

This Episode Is For You If:

• You're making decent money but still feel financially stressed

• You want options beyond your paycheck but don't know where to start

• You're tired of feeling like everything depends on your next paycheck

• January financial advice usually overwhelms you more than it helps

• You want systems that reduce anxiety, not add more tasks to your list

Before You Hit Play, Ask Yourself:

What's one income stream you'd love to build if you knew it wouldn't be complicated? If you only had one hour this month to improve your finances, what would you spend it on? Drop your answers in the comments or the Basement Facebook group because Mel's framework plus Joe and OG's January reality check might be exactly what you need to start the year without the usual stress.

FULL SHOW NOTES: https://stackingbenjamins.com/build-your-money-engine-mel-abraham-1790

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

Enjoy!

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What if some of the "rules" you've been told about money aren't rules at all, just assumptions that haven't been questioned lately?

Joe Saul-Sehy, OG, and Neighbor Doug pull apart a handful of deeply held financial beliefs and see what holds up when real life enters the conversation. From Social Security timing to investment return expectations, the crew explores where common advice works, where it falls short, and why context matters more than catchy rules of thumb.

Along the way, the discussion shifts from spreadsheets to behavior, because knowing what to do is one thing and doing it (especially in retirement) is another. The team talks through spending realities, inflation anxiety, and how small mindset shifts can make your plan feel less fragile and more livable.

Then, just when things get serious, Doug introduces a challenge that's equal parts practical and revealing. The Survivor Pantry. It's a simple idea that uncovers how prepared (or not) we really are, and why preparedness isn't about fear but flexibility.

In This Episode You'll Explore:

• Why popular Social Security advice isn't one size fits all

• What real world investment returns look like over time

• How behavioral blind spots can derail otherwise solid plans

• The difference between planning for retirement and living in it

• Smarter ways to think about spending as prices change

• Why some financial myths refuse to die (and how to spot them)

• What the Survivor Pantry reveals about readiness and resilience

• How questioning assumptions can lead to calmer, more confident decisions

This episode is less about finding new answers and more about asking better questions, especially if you're tired of feeling like you're "behind" for not following every money rule to the letter.

Conversation Starter for the Basement:

What's one money belief you've always accepted but now you're not so sure about? Drop your thoughts in the Facebook group or comments and compare notes with other Stackers who are rethinking the playbook right alongside you.

FULL SHOW NOTES: https://stackingbenjamins.com/challenging-money-assumptions-1789

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

Enjoy!
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It's that time of year when we look ahead, squint confidently into the future, and pretend we have any idea what's coming next. In this annual Stacking Benjamins tradition, Joe Saul-Sehy welcomes back Mindy Jensen from the BiggerPockets Money Podcast, Len Penzo of LenPenzo.com, and OG for the predictions episode that blends money talk, pop culture, and just enough nonsense to keep everyone honest.

Instead of pretending anyone can forecast the markets, the crew leans into what really matters: how to think about uncertainty. With help from a Magic 8 Ball (clearly the most reliable forecasting tool available), the panel throws out bold guesses about stocks, crypto, AI, inflation, interest rates, and the kinds of headlines that will dominate conversations in 2026. Some predictions are financial. Some are cultural. Some are optimistic, let's say.

But beneath the fun is a useful reminder for Stackers. Predictions don't build wealth, process does. This episode isn't about acting on guesses. It's about stress-testing assumptions, questioning narratives, and remembering that long-term success comes from good habits, not crystal balls. If you've ever wondered how much attention to pay to forecasts (and how much to ignore), this conversation delivers clarity wrapped in entertainment.

And yes, there are sports predictions, celebrity guesses, and enough wild speculation to guarantee at least a few laughs when we look back a year from now.

In This Episode You'll Hear:

The crew's biggest financial and cultural predictions for 2026

What the Magic 8 Ball "thinks" about markets, rates, and inflation

Why forecasts are fun but dangerous if taken too seriously

Thoughts on AI, energy use, and how technology may affect daily life

Predictions about crypto, gold, and the stories investors love to chase

A reminder of what matters when markets surprise everyone

Sports, pop culture, and wildly specific guesses that will age somehow

Join the Conversation:

Which prediction do you think has the best chance of being right, and which one will age the worst? Share your take in Spotify comments or the Basement Facebook group so we can revisit it next year and keep receipts.

This episode is a reminder that while nobody knows what 2026 will bring, Stackers who stay curious, flexible, and grounded tend to do just fine. Magic 8 Ball or not.

FULL SHOW NOTES: https://www.stackingbenjamins.com/magic-8-ball-and-2026-predictions-1788/

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

Enjoy!
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