Choosing the Best Tax Software for Your Needs

Tax season is here—so which software should you trust with your hard-earned Benjamins? Eric Rosenberg from The College Investor joins us to break down the best options, whether you're a side hustler, crypto investor, or just looking for a free filing solution.

• Will TurboTax take the crown again, or is there a surprise champ? You might be shocked by which software stands out this year.

• H&R Block’s virtual tax prep – If you want real humans to double-check your numbers, this might be your go-to.

• Which tax software works best for unique situations – Side gigs, stock trading, crypto investments… different situations call for different solutions.

• Navigating Tax Day without the stress – Tips to avoid last-minute panic and make sure you’re not leaving money on the table.

• Crypto scams and meme coins – Because tax season isn’t stressful enough without adding that mess into the mix.

Meanwhile, Doug serves up world-famous trivia with a nod to classic children’s books, beloved authors, and sing-song rhymes. Plus, we take a detour into sector betting, market trends, and—of course—movie recommendations.

If tax season feels overwhelming, this episode breaks it down, keeps it light, and helps you pick the right software to file with confidence.

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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Ever wondered if working for yourself could be the game-changer your finances need? Grant Sabatier thinks so, and today, he’s diving into the realities of entrepreneurship—from smart strategies to potential pitfalls.

• Where to start if you’re considering entrepreneurship – Not every side hustle is a winner, so how do you know if this path is right for you?
• The power of systems and constraints – Why guardrails and structure matter more than unlimited freedom.
• Pricing strategies and finding customers – Because even the best ideas need paying customers.
• Entrepreneurial misconceptions – Spoiler: It’s not all Ferraris and private jets.
• Can your wedding be a tax deduction? – We explore the entertaining but highly questionable ways some people try to make this work.

Meanwhile, Doug serves up trivia on the highest-grossing console game ever (bet you won’t guess it). And if you stick around long enough, let’s just say there may or may not be a discussion about a comedy movie that turns financial struggles into pure entertainment. But, you know… no promises.

If you’ve been toying with the idea of starting your own thing, this episode is packed with insights, real talk, and a few surprises along the way.

FULL SHOW NOTES: https://stackingbenjamins.com/unlock-your-inner-entrepreneur-with-grant-sabatier-1654

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

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Feeling the pressure to constantly tweak your investments? Today, we uncover the surprising benefits of financial inaction with insights from CFP Dana Anspach, Len Penzo, and OG. We dive into the wisdom of sometimes doing nothing—because, as it turns out, sitting on your hands (financially speaking) can be a power move.

• Why lazy portfolio management might be the smartest strategy you’ll ever adopt (spoiler: it involves less work).
• The power of downtime—turns out, stepping away from your money might actually make you richer.
• Why your future self will thank you for setting up auto-pay (hint: fewer late fees, more naps).
• The sneaky ways peer pressure messes with your finances—and how to keep the Joneses from running your budget.
• When rebalancing your portfolio is necessary…and when it’s just a fancy way to micromanage yourself.
• A wildly unexpected insurance claim (because finances are never boring in the basement).

Oh, and Doug’s got a trivia question about a particularly controversial activity that was banned—because, apparently, not everything fun is legal.

Stick around for weekend plans, final thoughts, and maybe even a surprise or two (because we like to keep you on your toes).

This episode originally aired on June 10, 2022. Please disregard any mention of current events.

The original show notes can be found here.

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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A great financial plan isn’t just about numbers—it’s about creating a roadmap that turns dreams into reality. Today, Joe and OG take a trip down memory lane, reflecting on their favorite parts of building a great financial plan. Whether you're tackling long-term goals, fine-tuning your tax strategy, or simplifying complex decisions, they’ll walk you through the key elements that turn financial chaos into a well-oiled machine.

• Breaking down big goals into bite-sized wins – Because climbing a financial mountain is easier when you focus on one step at a time.
• The magic of tax strategies – Why a little planning now can keep more Benjamins in your pocket later.
• Risk management done right – Avoiding financial pitfalls so your plan stays strong, no matter what life throws your way.
• The power of simple solutions – Complexity doesn’t always mean better. Sometimes, the best financial strategies are the easiest to execute.
• The role of a financial guide – Whether you DIY your plan or bring in an expert, knowing when to get guidance is a game-changer.

Meanwhile, Doug tackles a ‘Winnie the Pooh’-inspired predicament (honey jars may or may not be involved) and drops some surprising trivia on the massive market value of antidepressant drugs.

If you’re ready to streamline your financial life and celebrate your progress along the way, this episode is packed with insights, strategy, and a few unexpected twists.

This episode originally aired on January 18, 2023. Please disregard any mention of current events.

The original show notes can be found here.

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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Ever felt overwhelmed by buying a car or managing your time? You’re not alone. Today, we tackle both topics with expert insights and a few unexpected surprises along the way.

• Car buying decoded – Joe sits down with Phil Reed, Senior Consumer Editor at Edmunds, to break down the best strategies for buying new or used cars, leasing vs. buying, and negotiating with dealers like a pro.
• The ultimate time management playbook – Paula Pant, Dominique Brown, and returning guest Carrie Smith share real-world productivity hacks—whether you're self-employed, working 9-to-5, or just trying to make better use of your day.
• Avoiding social media missteps at work – The team dives into the do’s and don’ts of posting while employed.
• Email overload? Phone calls running your life? – Smart strategies to take control of your inbox and stop wasting time on endless calls.
• Celebrity wealth secrets and entertainment picks – Because financial wisdom can come from surprising places.
• A roadside hawk encounter?! – An unexpected story that proves you never know what’s coming next.

With practical advice, engaging discussions, and a few twists you won’t see coming, this episode packs in everything you need to take control of your finances and your time—without taking life too seriously.

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If disaster struck tomorrow, would your financial essentials be ready to grab and go? Today, Joe—along with contributors Paula Pant from Afford Anything, Jesse Cramer from Personal Finance for Long-Term Investors, and our resident expert OG—assemble the ultimate financial go bag. Meanwhile, Doug handles his usual duties as announcer, trivia master, and general chaos instigator.

• The must-have documents – Passports, Social Security cards, insurance policies... what belongs in your bag, and what can stay in the filing cabinet?
• Cash vs. digital access – How much should you keep in physical cash? And is gold really a smart emergency asset, or just a really heavy way to slow yourself down?
• Estate planning and emergency preparedness – The financial moves today that can make a crisis less stressful later.
• Password managers: genius or a liability? – We debate whether your digital keys should be stored in the cloud, on paper, or tattooed in invisible ink.
• Trivia showdown: Doug tests the team’s knowledge with a question that (probably) has nothing to do with financial preparedness.
• Campus co-op stores and Harvard history—why are we talking about this? You’ll find out.

If you’ve been meaning to get your financial house in order for emergencies, this episode has everything you need to build your own financial go bag—without overpacking.

FULL SHOW NOTES: https://stackingbenjamins.com/your-financial-go-bag-1650

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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Is your insurance setup rock-solid, or are you unknowingly leaving gaps that could cost you big time? Today, we break down the essentials of managing risk in our no-nonsense (but totally entertaining) insurance guide.

• How much coverage do you really need? We tackle the must-haves and the unnecessary add-ons that might just be draining your wallet.
• Auto, home, life, and disability insurance—what’s essential and what’s overkill? We walk through the key policies that keep you protected without breaking the bank.
• Oddball insurance policies—are they worth it? From pet insurance to that ‘just in case’ coverage you saw on late-night TV, we separate the smart buys from the money traps.
• A TikTok minute that perfectly sums up the difference between dogs and cats. Trust us, you’ll relate.
• Listener questions: Breaking up with a financial advisor—when it’s time to walk away and how to do it right.
• Insurance company showdown: Who’s the biggest player in the game, and does size really matter?
• DIY money moves: How to take over your own investment accounts without making costly mistakes.

Stackers, this episode is packed with tips, laughs, and real-world insights to help you protect what matters—without wasting a dime. Don't miss it!

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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Ever feel like your budget is running you instead of the other way around? Today, we’re bringing in Shaun Morgan from The Teacher Money Show and Kristin Wade, budgeting coach at My Budget Coach, to help you flip the script. They’ll share how tracking your expenses is the first (and easiest) step toward financial freedom, why budgeting shouldn’t feel like punishment, and how to make your money work without the guilt.

But wait—there’s more! We’re diving into creative ways to gamify saving, some unexpected solutions for real estate dilemmas (hint: selling isn’t your only option), and why sometimes renting out your home might be the smarter move. And of course, we sprinkle in some personal stories, real-life lessons, and a few side tangents that may or may not include baseball, beer trends, and an ode to Steve Jobs.

What’s Inside Today’s Episode:

• Budgeting Basics: How to make your spending work for you.
• Tracking Expenses 101: The first step toward a stress-free financial plan.
• Finding the Right Budgeting Tools: What actually works?
• Gamifying Your Finances: How to make saving and budgeting fun (yes, fun!).
• Accountability & Motivation: Why most people quit budgeting—and how to stick with it.

• Turning Real Estate Woes Into Wins: If your house won’t sell, here’s what to do next.
• Renting vs. Selling: When keeping your home might be the smarter play.
• Running a Business on a Budget: The hidden costs and how to stay profitable.

• Community Shoutouts & Listener Feedback: Your wins, your questions, and more.

• Random Topic: Cancun adventures and off-the-cuff fun.
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Key Takeaways from the Episode:

✔️ Budgeting doesn’t mean restriction—it means intentional spending.

✔️ Tracking your money is like using a GPS—it keeps you from getting lost.

✔️ Real estate has more options than just “sell or stay put.” Renting could be a game-changer.

✔️ You don’t have to budget alone. The right tools and accountability partners make all the difference.

✔️ Even Cancun has budgeting lessons. (Or at least a few good stories.)

Tune in now and take the first step toward mastering your budget—without making it feel like a chore.

FULL SHOW NOTES: https://stackingbenjamins.com/how-to-take-control-of-your-budget-1648

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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Is it time to break up with international stocks? They’ve been underperforming U.S. markets for years, so should we finally call it quits, or is there still hope for a global comeback? On today’s episode, Joe, OG, Paula Pant, and Jesse Cramer dig into the great international investing debate.

• Are international funds a lost cause? The panel unpacks why they’ve lagged U.S. stocks and whether diversification still makes sense.
• Beyond stocks: Exploring other asset classes—private equity, real estate, commodities, and collectibles (because who doesn’t want to invest in Beanie Babies and vintage lunchboxes?).
• The $3 coin mystery: Yep, that was a thing. And yes, it’s as weird as it sounds.
• Election results and wooden nickels: The intersection of money, history, and questionable currency choices.
• Weekend plans and podcast highlights: Because investing is important, but so is having fun.

Of course, it wouldn’t be a Stacking Benjamins episode without some friendly debate, expert insights, and the occasional off-the-wall tangent. Tune in for a laid-back but insightful conversation on making smart investment decisions!

FULL SHOW NOTES: https://stackingbenjamins.com/is-international-investing-dead-1647

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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Ever experienced the gut-wrenching moment of losing a job—or worried about what you’d do if it happened? Today, we tackle how to prepare, what to do immediately, and the smartest moves to protect your finances if your job ever disappears. From building an emergency fund to making the most of employer benefits, we’ll walk you through the steps to keep your financial house in order when life throws a curveball.

But that’s not all. Estate planning gets a shake-up thanks to the new Secure Act 2.0, and we’re diving into what it means for inherited Roth IRAs (hint: the government has new rules, and you’ll want to know them).

And because we can’t resist a good detour, we also explore the real cost of horse ownership (spoiler: it’s more than just hay money) and why tide pooling is more financially educational than you’d think. All that, plus trivia, TikTok wisdom (or nonsense), and plenty of lively discussion from the basement crew.

What’s Inside Today’s Episode:

• Job Loss Survival Guide: How to prepare before, during, and after a layoff.
• Emergency Fund Essentials: Why you need one (and how much is enough).
• Navigating Employer Benefits: Making the most of what’s available before you leave.
• Secure Act 2.0 & Estate Planning: The new rules around inherited Roth IRAs.
• Trivia & The TikTok Minute: Because questionable financial advice is always worth dissecting.
• Horse Stackers & Expensive Hobbies: Ever wonder what it really costs to own a horse? We break it down.
• Tide Pooling Adventures: A financial lesson wrapped in sea creatures and crashing waves.

Key Takeaways from the Episode:

✔️ Job security is a myth—be ready. Build that emergency fund, update your resume, and keep networking.

✔️ Your employer’s benefits might be your hidden lifeline. Know what’s available before you walk out the door.

✔️ Secure Act 2.0 changes estate planning. If you’re inheriting a Roth IRA, don’t assume the old rules apply.

✔️ Horses aren’t just expensive—they’re financial black holes. But that won’t stop people from trying.

✔️ Tide pooling might be the best investment lesson in disguise. Patience, observation, and avoiding getting pinched—it’s practically a stock market metaphor.

Tune in now to make sure you’re financially prepared—whether it’s for job loss, estate planning changes, or just the unexpected expenses of a very expensive hobby.

FULL SHOW NOTES: https://stackingbenjamins.com/spring-cleaning-your-estate-plan-1646

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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Feeling stuck in your financial plan—or maybe just in life in general? Whether it’s your money, career, or day-to-day habits, a little innovation can go a long way. Today, we’re breaking down how to rethink and restructure your approach to financial planning and work-life balance using lessons from Microsoft (yes, the Xbox folks). Dean Carignan and JoAnn Garbin insights on how to build a system for innovation—because the best financial plans (and lives) aren’t built by accident.

Meanwhile, a woman was scammed out of her savings, and a major financial company had to pay a fine—even though they didn’t actually rip her off. What happened? And what does it mean for how we protect our own money? We’ll break it all down.

Elsewhere in the episode, we discuss why trusted contact forms are crucial for safeguarding elderly relatives’ finances, how OG wants you to rethink your daily money habits, and why the Xbox case study holds lessons for designing a better financial plan. Plus, Doug has thoughts on podcast innovation, trivia, and—because it wouldn’t be a proper basement gathering without it—a hot take or two.

What’s Inside Today’s Episode:

• A Woman Gets Scammed, But Who Pays the Price? A big financial firm faces a fine—without actually doing anything wrong.
• The Xbox Case Study: What Microsoft’s innovation strategy can teach you about structuring your financial future.
• Financial Planning Innovations: Why thinking like an engineer (or a game developer) might help you build a better plan.
• Rethinking Your Everyday Financial Habits: OG’s take on how small changes lead to big results.
• Trusted Contact Forms & Safeguarding Elderly Relatives: A simple but powerful tool to prevent financial disasters.
• Charitable Giving Strategies: How to give smarter, not just more.
• Doug’s Trivia Time: A deep dive into financial (and podcast) innovation—because why not?
• Building a Network in Retirement: Why relationships matter just as much as money when designing your post-work life.

Key Takeaways from the Episode:

• You can’t just wing it with your finances. Microsoft doesn’t build Xbox consoles on a whim—your financial future needs the same level of structured innovation.
• Don’t assume big financial firms will protect you. A major company had to pay up even though they weren’t the scammers—learn how to protect yourself before something happens.
• Small financial tweaks can make a massive difference. Just like product innovations, incremental changes in your money habits can lead to big wins over time.
• Retirement isn’t just about the money. You need a network, a purpose, and a strategy—or you’ll find yourself wealthier but bored out of your mind.

Tune in now to learn how to bring structured innovation into your finances, career, and life!

FULL SHOW NOTES: https://stackingbenjamins.com/the-importance-of-innovation-1645

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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