Podcasts about overpaying

College can be one of the biggest financial decisions a family will ever make.  Overpaying for college can create years of unnecessary debt and stress, but today's guest is going to share how families can be strategic, informed, and confident so they don't leave money on the table. If you get a ton of value in this episode, I would love to invite you to subscribe because it costs nothing to subscribe. Crystal Tate is the founder and CEO of Crystal Clear College Planning and co-founder of the SCHOLARS Service Center.  With more than 15 years of experience and over 1,000 families served, she helps families combine smart admissions strategy with financial planning so they can avoid overpaying for college.  Crystal's work is especially focused on first-generation, rural, and middle-income families who want a clear, confident path to higher education.  Welcome, Crystal!Support the showCheck out Strategic Sales Queen for more great interviews, podcasts, and blogs to help you achieve more, faster!https://www.strategicsalesqueen.com/​

Waiting until January to start tax planning could cost you valuable tax savings. In this episode, Tiffany shares five year-end tax strategies business owners should review before key deadlines pass. You'll learn why a tax projection should come first and how retirement contributions, equipment purchases, S corporation payroll, business expenses, and estimated payments can affect your final bill. Tiffany also explains why your bank balance is not your taxable profit. You'll discover which decisions may need to happen by December 31 and which payments can wait until later. These are practical business finance moves based on expenses and investments you already planned to make. Listen now before your best year-end options disappear. Next Steps:

Are you paying your company's bills with your own money? If you own an S corporation, your company may be able to pay or reimburse those costs without adding the money to your taxable wages. In this episode, Tiffany explains how an accountable plan works. You'll learn which expenses may qualify, including business mileage, phone service, travel, education, and a home office. You'll also discover what records to keep and why reimbursement deadlines matter. One business owner was personally paying about $24,000 in company expenses each year. A better system helped her company cover those costs correctly and could reduce unnecessary payroll taxes over time. This practical tax strategy can improve cash flow and support tax reduction, but you must follow the rules. Listen now before you pay another business expense from your personal account.

Could your business structure be costing you tens of thousands of dollars each year? In this episode, Tiffany explains how a consultant earning $1.5 million faced nearly $74,000 in self-employment and Medicare taxes. After modeling an S-Corp election and a reasonable salary, the gross employment-tax difference was about $50,000. You'll learn how S-Corps work, why owner salary matters, and which IRS rules you cannot ignore. Tiffany also covers QBI, payroll costs, state fees, and other details that can change your true savings. This is practical CPA advice for owners who want smarter tax planning, better business finance, and legal tax reduction. Before you file another Schedule C, listen now and find out whether your business structure needs a second look. Next Steps:

Health Savings Accounts are known for their powerful triple tax advantage. But an HSA is not the right choice for every business owner. In this episode, Tiffany explains five situations where an HSA could cost you more than it saves. You'll learn how high deductibles, regular medical bills, account fees, strict withdrawal rules, and unpredictable costs can weaken the benefits. You'll also discover when an HSA can support your tax strategies and long-term wealth planning. The best financial tool is one that fits your health needs, cash flow, and future goals. Before choosing an HSA for the tax savings, make sure you understand the full cost. Next Steps:

The money in your business bank account is not always yours to spend. In this episode, Tiffany shares how one business owner confused cash with profit—and nearly ran out of money after taking large owner draws. A hidden $68,500 tax bill and penalty left her business with a dangerously small cash cushion. You'll learn the three numbers every owner should track: total cash, committed cash, and truly available cash. Tiffany also explains how to build a tax reserve, update estimated tax payments, and review smart year-end moves. These practical tax planning and cash flow lessons can help you make better money decisions and protect your business finance. Before you transfer another dollar, listen to this episode. Your bank balance may be telling the wrong story. Next Steps:

Should you sell your rental property or leave it to your children? The answer could change your family's tax bill by six figures. Tiffany explains how a stepped-up basis may reduce capital gains taxes when a property is inherited. You'll learn why gifting property too soon—or adding a child to the deed—can create an unexpected tax problem. She also explains how a properly funded revocable living trust may help a property avoid probate while protecting important tax benefits. This episode breaks down the difference between equity and tax basis, why a date-of-death appraisal matters, and how to compare selling now with holding for your heirs. These tax strategies, tax planning, wealth planning, and major money decisions can shape what your family keeps. Listen before you sell, gift, or change a property deed. Next Steps:

In this episode, Tita Obii-Obioha shares his journey from a seasoned appraiser to a real estate investor and developer in Houston. Discover how his valuation expertise influences his investment decisions, market outlook, and strategies for success in a competitive market.   Professional Real Estate Investors - How we can help you: Investor Fuel Mastermind:  Learn more about the Investor Fuel Mastermind, including 100% deal financing, massive discounts from vendors and sponsors you're already using, our world class community of over 150 members, and SO much more here: http://www.investorfuel.com/apply   Investor Machine Marketing Partnership:  Are you looking for consistent, high quality lead generation? Investor Machine is America's #1 lead generation service professional investors. Investor Machine provides true 'white glove' support to help you build the perfect marketing plan, then we'll execute it for you…talking and working together on an ongoing basis to help you hit YOUR goals! Learn more here: http://www.investormachine.com   Coaching with Mike Hambright:  Interested in 1 on 1 coaching with Mike Hambright? Mike coaches entrepreneurs looking to level up, build coaching or service based businesses (Mike runs multiple 7 and 8 figure a year businesses), building a coaching program and more. Learn more here: https://investorfuel.com/coachingwithmike   Attend a Vacation/Mastermind Retreat with Mike Hambright: Interested in joining a "mini-mastermind" with Mike and his private clients on an upcoming "Retreat", either at locations like Cabo San Lucas, Napa, Park City ski trip, Yellowstone, or even at Mike's East Texas "Big H Ranch"? Learn more here: http://www.investorfuel.com/retreat   Property Insurance: Join the largest and most investor friendly property insurance provider in 2 minutes. Free to join, and insure all your flips and rentals within minutes! There is NO easier insurance provider on the planet (turn insurance on or off in 1 minute without talking to anyone!), and there's no 15-30% agent mark up through this platform!  Register here: https://myinvestorinsurance.com/   New Real Estate Investors - How we can work together: Investor Fuel Club (Coaching and Deal Partner Community): Looking to kickstart your real estate investing career? Join our one of a kind Coaching Community, Investor Fuel Club, where you'll get trained by some of the best real estate investors in America, and partner with them on deals! You don't need $ for deals…we'll partner with you and hold your hand along the way! Learn More here: http://www.investorfuel.com/club   —--------------------

Give your kids enough that they can do anything, but not so much that they can do nothing. That Warren Buffett line is where this one starts. You worked hard so your family could have a good life. So how do you keep the life you built from softening the kids you love? This is the first episode of Good Questions, where we pull the best questions dads have asked across ten years of podcasts and member-only conversations, and stack the answers worth keeping. Four dads take this one on: Mike McCarthy on being honest with your kids about your wealth and what the trust will and will not do, Chad Willardson on raising abundance-minded kids instead of scarcity-minded ones, Scott Donnell on why you should let them waste some of their own money, and Dan Miller on how early kids should start working (his answer involves a rebuilt motorcycle and a 10-year-old).   IN THIS EPISODE: The Buffett rule: enough to do anything, not so much they do nothing What to actually tell your kids about your money, and what the trust should gate Overpaying your kids on purpose: $50 book reports and a 12-year-old's dog-walking business "Let them buy the Mountain Dew": why a wasted $30 now beats a wasted $3,000 later The $410 motorcycle rebuild that taught a 10-year-old to earn what he rides Why kids learn economics from life experiences, not from sitting in seats  

One lawsuit could put more of your rental portfolio at risk than you think. An LLC alone may not be enough. In this episode, Tiffany explains the four layers of real estate asset protection: insurance, separate entities, privacy, and advanced legal planning. You'll learn the difference between a claim tied to a property and one that follows you personally. Tiffany also shares how better coverage and separate entities helped protect a client's six-property portfolio. These smart strategies can support your wealth planning, but every state has different rules. Your attorney, insurance advisor, lender, and tax professional must work together. Before another claim puts your properties at risk, listen and find the gaps in your plan. Next Steps:

Your rental properties may show big losses on paper, but that does not mean you can use those losses to lower your tax bill. The passive activity rules can keep them trapped for years. In this episode, Tiffany explains how Real Estate Professional Status works and why reaching 750 hours is not enough. You'll learn the two tests you must pass, how material participation works, and when grouping several properties may help. Tiffany also explains the special rules for married couples, real estate employees, and older suspended losses. These tax strategies could create major tax savings, but only when your hours, records, and tax planning support them. Listen now to learn whether this powerful tax strategy could work for you. Next Steps:

On this special segment of The Full Ratchet, the following Investors are featured: Larry Cheng of Volition Capital Ben Black of Akkadian Ventures and Powerlaw Corp Mark Peter Davis of Interplay We asked guests to tell the most important lesson they've learned in their career. The host of The Full Ratchet is Nick Moran of New Stack Ventures, a venture capital firm committed to investing in founders outside of the Bay Area. We're proud to partner with Ramp, the modern finance automation platform. Book a demo and get $150—no strings attached.   Want to keep up to date with The Full Ratchet? Follow us on social. You can learn more about New Stack Ventures by visiting our LinkedIn and Twitter.

Are massive frontier AI models actually worth the cost?In this episode, I sit down with Daniel Svonava, Founder of Superlinked, to break down where AI is actually heading in production. We dive into why the hype around massive frontier models is shifting toward targeted, small open-source models, and how to orchestrate smart agents without blowing through your budget.Daniel shares how Superlinked is building open-source inference infrastructure, why small models are rapidly closing the performance gap, and how you can engineer faster, cheaper, and more control-driven AI systems.

The QBI deduction can let qualifying business owners deduct up to 20% of their qualified business income. Now it is permanent—but that does not mean every owner will get the full benefit. In this episode, Tiffany explains the new 2026 income thresholds and why service businesses face tougher rules. You'll learn what happens when your income enters the phaseout range, how S corporations and owner pay affect QBI, and why a Roth conversion could shrink your deduction. You'll also discover why buying equipment or hiring workers just for a deduction can be a costly mistake. These practical tax tips will help you make smarter tax planning and money decisions before the year ends. Your QBI deduction may be changing while your business grows. Listen now so you can plan before it's too late.

Here's a question most practice owners don't ask their accountant: Do I actually owe this much? In this episode, Tracy Cherpeski talks with Rachel Michaelov, an Enrolled Agent and tax strategist who works exclusively with high-earning healthcare professionals. Rachel is the founder of Empire Tax Advisors and Practice Wealth Partners, and she has one mission: help doctors and dentists stop overpaying their taxes.  Rachel shares why most healthcare providers work with reactive CPAs instead of proactive tax strategists, the three most expensive mistakes she sees practice owners making, and strategies like cost segregation and R&D credits that could save you hundreds of thousands of dollars. She walks through a real example: a doctor with a $1.2 million tax liability who ended up with a $24,000 refund.  If you've ever felt like financial stress is stealing your time, your peace of mind, or your ability to reward your team, this conversation is for you. Rachel gets real about why this matters for your life, not just your spreadsheet.    Read the full show notes, memorable quotes, and key takeaways.  Connect With Us:  Be a Guest on the Show  Thriving Practice Community  Schedule Strategy Session with Tracy  Tracy's LinkedIn 

You've built a profitable business, and you're still handing more of it to the IRS than you need to. The real reason usually traces back to your structure. In this episode of CEO Numbers Network, I'm continuing our mid-year tax check-in series with a deep dive into business structure. Profitable business owners often keep paying self-employment tax long after their structure has stopped making sense. I break down the three signs that tell you you're ready for an S corp and the reasonable compensation rule the IRS requires once you make that switch. I also share a client story about what it actually took to get her ready, because the profit number alone wasn't enough. You will learn the three signs that tell you you're ready for an S corp, plus the reasonable compensation rule the IRS enforces once you make the switch. If you have ever wondered why your CPA never brought up an S corp, or worried you might be underpaying yourself the wrong way, this episode shows you exactly where to look.  

You've built a profitable business, and you're still handing more of it to the IRS than you need to. The real reason usually traces back to your structure. In this episode of CEO Numbers Network, I'm continuing our mid-year tax check-in series with a deep dive into business structure. Profitable business owners often keep paying self-employment tax long after their structure has stopped making sense. I break down the three signs that tell you you're ready for an S corp and the reasonable compensation rule the IRS requires once you make that switch. I also share a client story about what it actually took to get her ready, because the profit number alone wasn't enough. You will learn the three signs that tell you you're ready for an S corp, plus the reasonable compensation rule the IRS enforces once you make the switch. If you have ever wondered why your CPA never brought up an S corp, or worried you might be underpaying yourself the wrong way, this episode shows you exactly where to look.  

One business owner used $270,000 in investment losses to reduce his federal tax by about $64,000 in the year he sold his company. But was it true tax savings—or simply a bill moved into the future? Tiffany explains how direct indexing and tax-loss harvesting can help offset capital gains while keeping a portfolio invested. You'll learn how lower cost basis, added fees, investment risk, and the wash-sale rules can change the final result. Listen now and learn where the opportunity—and the hidden tax trap—may be.

One business owner paid $21,600 a year for family health insurance. He thought he was getting the tax deduction—but a simple S corporation reporting mistake cost him about $7,000 a year. In this episode, Tiffany explains how the self-employed health insurance deduction really works. You'll learn why the rules change for sole proprietors, partners, and S corporation owners. You'll also discover three traps that can erase the deduction, including low earned income, access to an employer health plan, and missing W-2 reporting. These practical tax tips can help you improve your tax planning and avoid leaving valuable tax savings on the table. Tiffany also explains why this deduction lowers income tax but not self-employment tax. If you pay for your own health insurance, listen now—before another tax year slips away. Next Steps:

Is your S corp salary putting your business at risk? Many owners pay themselves a small wage and take the rest as distributions. That may cut payroll taxes, but it can also raise an IRS red flag. Tiffany explains how the IRS decides whether your salary is reasonable. You'll learn why the popular 60/40 rule is a myth, what happens when distributions are treated as wages, and how market data can protect you. She also shares three ways to calculate your salary and the records you should keep. These practical tax strategies and tax planning steps can help you lower risk without giving up legal tax savings. Before you run your next payroll, learn how to choose—and prove—the right salary. Listen now before a surprise IRS letter forces you to learn the hard way. Next Steps:

Is your accountant preparing your taxes or actively helping you reduce them?In this episode of Grow Your Business & Grow Your Wealth, Gary Heldt speaks with Boris Musheyev, CPA, Certified Tax Strategist, and founder of BORISMTAX, about why profitable business owners often pay more in taxes than necessary.Boris explains the critical difference between tax preparation and proactive tax planning, when a growing business should begin working with a tax advisor, and why the advisor who helped when you launched may not have the experience required for your current income level.They also discuss how business owners can evaluate a tax advisor, why professional designations alone do not guarantee strategic expertise, and how year-round planning can uncover legal tax-saving opportunities before it is too late to use them.Key Takeaways✓ Why tax preparation and tax planning are two entirely different services.✓ When reaching approximately $100,000 in net profit should trigger a tax-strategy conversation.✓ How business owners can outgrow the accountant who served them during their early years.✓ What to examine before trusting a tax advisor with advanced strategies.✓ Why midyear planning and year-end projections are essential for reducing taxes legally.About Boris MusheyevBoris Musheyev is a CPA, Certified Tax Strategist, and founder of BORISMTAX, a tax planning and advisory firm serving entrepreneurs and business owners across the United States. His firm specializes in helping profitable businesses use proactive, legal tax strategies to reduce their tax liability and retain more of what they earn. Boris is also the host of the Tax Reduction Podcast, and BORISMTAX has been recognized on the Inc. 5000 list for two consecutive years.Connect With Boris MusheyevWebsite: https://borismtax.comFree Tax Strategy Training: https://save100k.comEmail: support@borismtax.comPhone: 212-430-6881Podcast: Tax Reduction PodcastLinkedIn: Boris Musheyev, CPA

Why do wealthy people often pay less in taxes? It is not always because they earn less. It is because they own assets and use the tax code differently. In this episode, Tiffany explains how business owners and investors use appreciation, borrowing, depreciation, cost segregation, and step-up in basis to protect and build wealth. You will hear real examples of people who accessed cash, lowered taxable income, and planned for future wealth transfers without relying on illegal loopholes. You will also learn why strong tax planning starts long before tax season—and how stacking several legal tax strategies can create a much bigger result. This episode offers practical CPA advice for business owners who want better tax savings, smarter wealth planning, and a stronger long-term tax strategy. Listen now and learn why keeping more starts with owning differently.

If you're stressed about buying a car with kids because it might just be the most overwhelming grown-up thing there is, this episode is for you!For this week's episode, I brought in Lauren Fix, The Car Coach, and asked her all the questions you're too embarrassed to ask: minivan vs SUV (and are minivans really less safe?), how many car seats actually fit across a back seat, leasing vs buying, and the dealer tricks that quietly cost families thousands. Come walk into that dealership knowing more than the salesperson.We dive deep into:Where to even START when you have no idea (your kids' ages, road trips, and all the GEAR)Minivan vs SUV vs full-size, and whether minivans are really the "less safe" optionHow many car seats actually fit across a back seat, and the latch system nobody explainsThe safety features genuinely worth it when you've got littles riding alongNew vs used, and the ONE check you should never skip on a used carLeasing vs buying, and the mileage number that basically decides it for youThe two discounts dealers are hoping you never ask forWhat to say a hard NO to once you're in the finance officeNever pay retail: how to walk in prepared, and when to just walk away----------------------------------------------------------------------------IMPORTANT LINKS•✨ Join our Mom Club on Patreon HERE ✨

Your September 15 estimated tax payment may be much larger than it needs to be. In this episode, Tiffany explains four tax strategies that can help business owners protect their cash flow and avoid costly underpayment penalties. You'll learn how the IRS safe harbor rule works, why S corporation withholding can help correct missed payments, and how seasonal businesses can use the annualized income method. You'll also discover how retirement contributions and properly timed equipment purchases may lower the income used to calculate your estimated taxes. Estimated payments should match how your business actually earns money. They should not force you to drain your cash when you need it most. Listen now—because there may still be time to reduce your September tax check. Next Steps:

Tom Mitchell, The Honest Car Guy, joins The Morning XTRA to share practical advice on buying the right vehicle without wasting money. From avoiding unnecessary upgrades to finding hidden value in the used car market, Tom explains why honesty and smart math should drive every purchase. He also shares the personal story behind building his business and why putting customers first has become his mission. Watch The Morning Xtra every weekday from 6 a.m. to 10 a.m. on the Xtra 106.3 YouTube or listen on the Xtra 106.3 App

Are you paying more than you should for credit card processing? The answer for many businesses is yes. In this episode of Payments Podium, Kevin Olsen sits down with Jimmy Moore, CEO of FLO Business Solutions, to uncover the biggest mistakes business owners make when choosing a payment processor, understanding processing fees, and managing payment acceptance costs. From hidden fees and PCI compliance charges to cash discounting and dual pricing, this conversation is packed with practical advice that can save businesses thousands of dollars each year. In this episode, you'll learn: Why many businesses unknowingly overpay for payment processing How to identify hidden fees on your merchant statement Understanding effective processing rates PCI compliance and how to avoid unnecessary monthly charges Cash discounting vs. surcharge vs. dual pricing How to choose the right payment processing partner What banks and credit unions can do to better support their business customers The one strategy that can significantly reduce payment processing costs Whether you're a small business owner, banker, payments professional, or fintech leader, this episode provides practical insights to help you make smarter payment decisions and avoid costly mistakes. Guest: Jimmy Moore, CEO & Co-Founder, FLO Business Solutions

We're chatting some of the things you may be forking out more money for than you need to..and the habit swaps, tips and hacks to save some cash. As always, a quick reminder that this isn’t financial advice and all tips are general! This information mentioned was correct at the time of recording the episode in June 2026. Thanks to our sponsor Finder for making today's episode of Two Broke Chicks possible. To compare your options & browse the latest Finder Rewards jump on https://www.finder.com.au/finder-rewards

Many business owners work for years to build wealth but leave it exposed without realizing it. In this episode, Tiffany explains how a holding company can help protect cash, equipment, real estate, and other valuable assets from business liability. You'll learn when this strategy makes sense, how it works, common mistakes that can destroy its protection, and where tax planning opportunities may exist depending on your entity structure. Next Steps:

Think a cost segregation study automatically saves you thousands in taxes? Not so fast. In this episode, Tiffany Phillips, CPA, explains how cost segregation really works, who benefits most, and why a large deduction doesn't always mean immediate tax savings. You'll learn how tax strategies, passive activity rules, bonus depreciation, and timing all affect your results. Tiffany also shares when she actually tells clients not to order a cost segregation study—and why that's often the smarter business finance decision. If you own rental property or commercial real estate, this episode will help you avoid expensive mistakes and make better tax planning decisions with confidence. Listen now before you spend thousands on a strategy that may not fit your situation.   Next Steps:

Many homeowners and real estate investors pay more in property taxes than they should. A missing exemption, incorrect property record, inflated assessment, or ownership change could cost you hundreds—or even thousands—of dollars. In this episode, Tiffany shares six legal tax strategies that may help you lower, freeze, defer, or challenge your property taxes. You'll learn how to check your homestead exemption, find errors in your property record, prepare a strong assessment appeal, and avoid costly mistakes involving LLCs, trusts, and property classifications. You'll also learn why deadlines matter and how a simple ten-minute review could improve your cash flow and support your larger tax planning goals. Before you pay your next property tax bill, listen to this episode and check the record behind the number.   Next Steps:

Business owners hear it all the time: "Just buy it. It's a tax write-off." But that's not how smart tax planning works. In this episode, Tiffany Phillips, CPA, breaks down the biggest myths about tax deductions under the new tax law and explains how bonus depreciation, Section 179, QBI, business debt, and estimated taxes work together. You'll learn why buying equipment just to save taxes can actually cost you more, how to make better money decisions, and why great tax strategies look at your whole business—not just one deduction. If you want practical CPA advice that helps you keep more of what you earn, this episode is for you. Don't make an expensive tax mistake because of a headline. Listen now and learn how to build a smarter tax strategy before year-end. Next Steps:

If you recently started an LLC, this episode is for you. Many business owners think filing the paperwork is enough—but that's just the beginning. Tiffany Phillips, CPA, explains the five biggest LLC mistakes that can lead to higher taxes, lost deductions, missed deadlines, and weaker liability protection. You'll learn how to separate business and personal finances, understand how your LLC is taxed, stay compliant, structure property purchases correctly, and document business expenses the right way. These tax tips, tax planning, and business strategy insights can help you avoid expensive mistakes before they happen. Small changes today can save you money and headaches later. Listen now and learn how to build an LLC that works for you—not against you.   Next Steps:

Think every repair on your rental property is tax deductible? Not so fast. In this episode, Tiffany explains one of the biggest tax mistakes rental property owners make: confusing repairs with capital improvements. Learn how the IRS decides what you can deduct today and what must be depreciated over time. You'll also discover why good documentation matters, how safe harbor rules work, and simple tax planning strategies that could improve your tax savings. If you own rental property, these tax tips can help you avoid costly mistakes, improve cash flow, and make smarter tax strategy decisions before your next renovation. Don't wait until tax season to find out you got it wrong. Listen now and learn how to keep more of your money. Next Steps:

Your bookkeeping may look organized, but are the numbers actually correct? In this episode, Tiffany explains why every business owner should reconcile bank and credit card accounts each month. You'll learn how reconciliation catches missing income, lost deductions, duplicate charges, fraud, and other costly errors. You'll also discover why accounting software cannot replace human review—and how bad bookkeeping can lead to the wrong tax bill, unreliable financial reports, and poor business decisions. This simple monthly finance routine can improve your accounting and bookkeeping, protect your tax preparation, and give you numbers you can trust. Do not wait until tax season to discover that your books are wrong. Listen now and learn how one monthly habit can protect your money and your business. NEXT STEPS

Think a luxury SUV is always a bad financial decision? Think again. In this episode, Tiffany Phillips, CPA, explains how the IRS heavy vehicle rules can dramatically reduce the real cost of certain business vehicles. You'll learn how the 6,000-pound rule works, when Section 179 and bonus depreciation apply, how business use affects your deduction, and why buying the "cheaper" SUV can sometimes cost you more. Tiffany also covers financing, leasing vs. buying, documentation, depreciation recapture, and common mistakes that can reduce your tax savings. If you're a business owner planning to purchase a vehicle, these tax strategies could save you thousands while helping you make smarter business finance decisions. Listen now before you sign your next vehicle purchase. You could keep far more of your money. Next Steps:

Most business owners work hard to build wealth—but many pay far more in taxes than they need to. In this episode, Tiffany explains the powerful Buy, Borrow, Die strategy and how it can help high earners build wealth while reducing taxes legally. You'll learn how tax planning, short-term rentals, cost segregation, bonus depreciation, and borrowing against assets can work together to create long-term financial growth. You'll also discover how today's tax rules may help protect wealth for future generations. If you want practical CPA advice, smarter tax strategies, and better wealth planning, this episode is packed with ideas you won't want to miss. Listen now and learn how to keep more of what you earn.

Disclaimer: Today's episode is sponsored by Nurp. Content is for educational purposes only. Not advice. Results discussed have not been vetted. Claims made by the guest have not been verified. The views expressed by the guest do not reflect those of the host or this show.—

Most business owners think tax season ends after they file their return. But that's when many of the biggest opportunities get missed. In this episode, Tiffany Phillips, CPA, shares seven powerful tax strategies that could help business owners keep more of what they earn. You'll learn about the Augusta Rule, heavy vehicle deductions, S-Corp health insurance, home office deductions, Solo 401(k)s, business meals, and education expenses. These aren't loopholes—they're legitimate tax planning opportunities many business owners never hear about. If you want practical CPA advice that goes beyond filing a return and helps you build long-term tax savings, this episode is for you. Listen now and find out whether you're paying more tax than you need to.

If you own a home, you may be paying far more in property taxes than you have to. In this episode, Tiffany explains seven legal forms that can lower, freeze, or even eliminate your property tax bill. You'll learn about homestead exemptions, senior freezes, appraisal protests, disabled veteran benefits, and other tax strategies that many homeowners never use. She also shares common mistakes that cost people thousands of dollars every year and explains the deadlines that matter most. This episode delivers practical tax tips, tax planning, and tax reduction strategies that can help you keep more of your money. Don't assume your county will tell you what's available. They won't. Listen now and make sure you're not leaving money on the table. Next Steps:

The person next to you probably paid less for their seat than you did — and you'll never know it. Spencer talks with Sam Hollander, founder of Autopilot (withautopilot.com), about the overlooked art of saving money after you've already booked. Since U.S. airlines killed change fees, you can claw back cash every time your fare drops and snag last-minute premium-cabin upgrades for a fraction of the sticker price. Sam breaks down how to automate all of it, which tools every points-and-miles traveler should be using, and why free elite upgrades are quietly disappearing in 2026. Questions Asked What is Autopilot, and how does it save travelers money after booking? Are you canceling and rebooking the ticket, or filing a claim for the fare difference? What happens if the price drops multiple times? Does this work on codeshare flights? What do you need to share with Autopilot to get started? Does it work if you book with points or miles? How does the pricing and success-fee model work? How do the upgrade-offer alerts work, and do you recommend a bid amount? Do you need a credit card on file for the free tier? What travel tools are you using besides Autopilot? What's most exciting to you in the travel space right now? In 2026, with airlines selling most premium seats, what actually works to get up front? Where can people find you and follow what you're building? Main Topics Covered How the post-COVID end of change fees created the opening for Autopilot Lowest Fare Guarantee: automatic refunds when your booked fare drops $20+ Automation as a money philosophy — low-cost, automated, diversified, simple Importing trips via Gmail sync, email forwarding, or confirmation code Free tier vs. 25% success fee vs. $9.99/mo Pro plan Upgrade-offer bidding and how to judge whether an upgrade is worth it Why 2026 airlines are pulling back on free elite upgrades Day-of-departure price drops and pricing anomalies (business cheaper than premium economy) Best days to book and fly, and why "book now" beats waiting Building Alaska/Atmos Rewards miles through Bilt Autopilot's new hotel repricing feature Resources Mentioned Autopilot (withautopilot.com) MLA & SCRA fee waivers Google Flights (https://www.google.com/travel/flights) Seats.aero (https://seats.aero/) PointsYeah (https://www.pointsyeah.com/landing) ExpertFlyer (https://www.expertflyer.com/) CardPointers (https://cardpointers.com/) Travel Freely (https://travelfreely.com/) Max Rewards (https://maxrewards.com/) Flighty (https://flighty.com/) Bilt Rewards (https://www.bilt.com/) BofA Atmos Rewards Summit card Sam Hollander on X @samhollander_ https://www.withautopilot.com/ Advertiser Disclosure: This video may contain links through which we are compensated when you click on or are approved for offers. The information in this video was not provided by any of the companies mentioned, and has not been reviewed, approved, or otherwise endorsed by any of these entities. All opinions, analyses, and recommendations are the author's alone, not those of any bank, credit card issuer, airline, or hotel chain. Military Money Manual may receive compensation from JPMC.  Spencer and Jamie offer one-on-one Military Money Mentor sessions. Get your personal military money and personal finance questions answered in a confidential coaching call. militarymoneymanual.com/mentor Over 24,000 military servicemembers and military spouses have graduated from the 100% free, Ultimate Military Credit Cards Course available at militarymoneymanual.com/umc3 In the Ultimate Military Credit Cards Course, you can learn how to apply for the most premium credit cards and get special military protections, such as waived annual fees, on elite cards like the Chase Sapphire Reserve® Card. Learn how active duty military, military spouses, and Guard and Reserves on 30+ day active orders can get your annual fees waived on premium credit cards in the Ultimate Military Credit Cards Course at militarymoneymanual.com/umc3 If you want to maximize your military paycheck, check out Spencer's 5 star rated book The Military Money Manual: A Practical Guide to Financial Freedom on Amazon or at shop.militarymoneymanual.com. If you have a question you would like us to answer on the podcast, please reach out on instagram.com/militarymoneymanual. Offers may be expired: Offers, rates, fees, and benefits are subject to change and may have ended since this video was published — please verify the current terms on the issuer's official website before applying. Terms apply, and all cards are subject to credit approval. Any comments below are from individual users and are not provided, reviewed, approved, or endorsed by any issuer.

If you've spent any time shopping for overlanding gear, you've probably noticed something: add the word "overland" to almost any product, and the price seems to jump overnight. In this episode, I'm diving into what I like to call the **Overlanding Tax**—where it shows up, why it exists, and whether it's ever actually worth paying.I'll break down some of the biggest offenders, from rooftop tents and shovels, to vehicles and other things that can quietly drain your budget. More importantly, I'll share where I think spending extra really does get you better quality and where you might be paying more for branding than performance.Whether you're just getting into overlanding or you've been building your rig for years, this episode is all about helping you make smarter buying decisions, avoid unnecessary expenses, and focus your budget on the upgrades that truly improve your adventures.What do you think is the biggest example of the Overlanding Tax? Let me know in the comments—I'd love to hear where you think the industry gets it right... and where it gets a little carried away.Here are some of the budget priced options I talked about in the episode:Here's a link to the Alibaba page for this camper (use code ALLTHINGSOVERLANDING147 to get 2 items free, worth up to $170 or mention All Things Overlanding to your rep): https://www.alibaba.com/product-detail/Truck-Camper-Custom-Hard-Shell-Rooftop_1601727228413.html?spm=a2747.product_manager.0.0.380971d2UHgNseBudget Shovel: https://amzn.to/3Qhh3B3Setpower Fridge: https://amzn.to/3QSspvsHest Mattress: https://amzn.to/4faagCyWhite Duck Sleeping Bag: https://whiteduckoutdoors.sjv.io/c/2836542/1823262/21733?iratid=41039&u=https%3A%2F%2Fwhiteduckoutdoors.com%2Fcollections%2Fsleeping-bag%2Fproducts%2Fsleeping-bag-0-f

If you own an LLC, this episode could save you thousands of dollars. Learn the right way to pay yourself, when owner's draws make sense, and when an S-corp election may reduce your taxes. Tiffany explains these rules in plain English so you can avoid expensive mistakes and make smarter tax planning decisions. You'll also learn how tax strategies, business finance, and tax savings work together to help you keep more of what you earn. Whether you're just starting your business or already making six figures, this episode will help you build a better financial plan. Listen now before another tax year passes with money left on the table. Next Steps:

This episode explains one of the biggest tax strategies available to real estate investors: cost segregation. Learn how one investor increased a $25,000 deduction to more than $221,000 in the first year and why that created nearly $47,000 in tax savings. Tiffany also explains who benefits most, how tax planning changes the outcome, and why passive activity rules matter before moving forward. You'll hear when a study makes sense, how catch-up depreciation works for older properties, and what changed with 100% bonus depreciation. If you own investment property or plan to buy one, this episode could change how you think about business finance forever. Listen now before making your next real estate decision. Next Steps:

Discover all of the podcasts in our network, search for specific episodes, get the Optimal Living Daily workbook, and learn more at: OLDPodcast.com. Episode 3612: Jeff Rose explains practical steps for gaining control of debt by creating a realistic budget, tracking income and expenses, and identifying true disposable income. He also shows how cutting unnecessary spending and using extra cash to make debt overpayments can help reduce debt faster and lower overall interest costs. Read along with the original article(s) here: https://www.goodfinancialcents.com/simple-ways-to-improve-your-debt-management-skills/ Quotes to ponder: "Budgeting is about knowing how your finances work and controlling what you do with your money, in other words, not letting your money control you!" "Your disposable income is essentially the amount you have left on a monthly basis to pay towards your non-priority debts and, if you have any spare after doing this, to save and to spend on non-essential goods/services." "Overpaying your debts can be an excellent way to improve your debt management skills." Wealthfront's high-yield Cash Account: ⁠⁠https://wealthfront.com/OFD⁠⁠ This experience may not be representative of other Wealthfront clients, and there is no guarantee of future performance or success. Experiences will vary. The Optimal Finance Daily Podcast, Diana Merriam (collectively "Media Partner") are not clients of Wealthfront. The Media Partner receives cash compensation from Wealthfront Brokerage for this paid endorsement placed in their video, creating a conflict of interest. More details available via the referral link. The Direct Deposit Plus Investing Program from Wealthfront Advisers LLC and Wealthfront Brokerage LLC provides eligible clients a 0.25% APY increase above the base APY on eligible Cash Account balances (up to an overall boosted rate of 4.30% for a limited time when including the 0.75% APY boost for new clients) when you direct deposit $1,000 a month, plus open, fund, and maintain an investing account. Wealthfront may change or end the program at any time and determine eligibility at its discretion. Terms apply. Full details at ⁠⁠wealthfront.com/promo-terms⁠⁠.  The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC ("Wealthfront Brokerage"), Member FINRA/SIPC. Wealthfront Brokerage is not a bank. The Annual Percentage Yield ("APY") on cash deposits as of January 30, 2026, is representative, requires no minimum, and may change at any time. References to the APY for the Wealthfront Cash Account, including any APY increase, are to the APY paid by insured depository institutions that participate in our cash sweep program (the "Program Banks”).. Wealthfront Brokerage sweeps cash balances to Program Banks, where they earn the variable APY. Investing involves risk, including the possible loss of principal. Securities investments are not bank deposits, bank-guaranteed or FDIC-insured, and may lose value. Investment advisory services are provided by Wealthfront Advisers LLC, an SEC-registered investment adviser. Learn more about your ad choices. Visit megaphone.fm/adchoices

Most business owners hear about when to elect S-Corp status—but almost nobody talks about when it becomes an expensive mistake. In this episode, Tiffany Phillips explains when an S-Corp election can actually cost you more in taxes, penalties, payroll, and compliance than it saves. Learn how tax planning, tax strategies, and the right compensation plan can protect your business from costly IRS mistakes. You'll also discover the truth about reasonable compensation, QBI deductions, state tax traps, and common filing errors that trigger audits. If you've already elected S-Corp status—or you're thinking about it—this episode could save you thousands. Listen now before your next tax decision costs more than you realize. Next Steps:

Think your business travel isn't fully deductible? Think again. In this episode, Tiffany Phillips, CPA, explains the tax strategies behind business travel that many accountants overlook. Learn how to maximize tax savings with meals, mileage, per diem rates, international travel rules, spouse travel, and proper documentation. Tiffany breaks down the IRS rules in plain English and shares real examples of business owners who missed thousands in legal deductions because their CPA didn't ask the right questions. If you travel for conferences, client meetings, property tours, or supplier visits, this episode will help you keep more of what you earn while staying compliant. You'll also discover simple systems that make your deductions audit-ready. Don't leave money on the table—listen now and start making every business trip work harder for your business.

 In this episode, I break down the real difference between a compliance CPA and a tax strategist, and why that gap could be costing your business six figures a year. We cover three real case studies of business owners who lost tens of thousands of dollars because their CPA did the bare minimum, the three pillars that separate a preparer from a strategist, and the exact questions you should ask to find out if you're getting strategy or just compliance. If you're a business owner or real estate investor who's tired of vague tax advice, this one's for you. Next Steps:

This episode explains how business owners can legally hire their children to create tax savings while teaching valuable financial skills. Tiffany breaks down IRS rules, payroll requirements, entity structure considerations, and how a Roth IRA can help turn today's tax strategy into long-term family wealth. Next Steps: ➡️ Overpaying your CPA and the IRS? Learn how to stop it in this free training: https://go.phillipsbusinessgroup.com/registration

On this episode, we're talking about something that affects millions of fertility patients—but that almost nobody talks about until the bill shows up: reproductive tissue storage.If you have embryos, eggs, or sperm in storage, you know the drill. Every year, another invoice arrives. Maybe it's $600. Maybe it's $800. Maybe it's over $1,000. Most people just pay it because they assume that's the cost. But what if it isn't? Ali's guest today is Charlie Boyer, CEO and Co-Founder of Generations CryoVault, and he's on a mission to shake up an industry that he believes has gotten way too comfortable charging fertility patients more and more for storage. Charlie's background is actually in financial services and cord blood storage, but after taking a closer look at reproductive tissue storage, he started asking some uncomfortable questions: Why are prices so high? Why don't patients know they have options? And why are so many clinics owned by private equity firms without patients even realizing it? In this conversation, Ali and Charlie talk about transparency, private equity, patient choice, and Generation CryoVault's new Pricing Promise, which aims to dramatically lower the cost of long-term embryo, egg, and sperm storage. They also discuss whoownsyourcare.org, how to find out who actually stores your tissue, and what questions every fertility patient should be asking their clinic. Whether you have embryos in storage right now, you're considering fertility treatment, or you're just curious about where all those fertility dollars are going, this is a fascinating conversation about an often-overlooked part of the family-building journey.For more info, go to https://gencryo.com/IG: @generationscryovaultEPISODE SPONSORS: THE WORK OF ART BOOK SERIESAli's Children's Book Series about IVF, IUI and Family Building Through Assisted Reproductive Technology https://www.infertileafgroup.com/booksThe 3-book bundle is now just $49 (normally $79)!The latest book in the Work of ART series, “You Are a Work of ART," is for every kiddo born through ART -- and the people who love them.PHERDALIG: @pherdal_sciencePherDal is the world's first and only FDA-cleared, sterile, at-home insemination kit designed to help people build their families in the comfort of home. Created by parents who've been there, PherDal is safe, simple, and affordable—putting more options in your hands as you grow your family. Explore at PherDal.com.Go to PherDal.com today and use code INFERTILEAF for $10 off.CARAWAYCaraway cookware is beautiful, first of all — like, actually gorgeous sitting on your stove — but it also makes cooking feel easier and less stressful.Visit carawayhome.com to take an additional 10% off your next purchase using code INFERTILEAF at checkout.Advertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy

The tax rules changed, and many business owners still don't know how it affects them. In this episode, Tiffany Phillips breaks down four major tax strategies from the One Big Beautiful Bill that could create significant tax savings in 2026. This isn't theory. It's practical CPA advice with real numbers and real examples that can help you keep more of what you earn. If you're a business owner or real estate investor, these are decisions that need attention before year-end. Don't wait until tax season. Listen now and discover the moves that could save you thousands. Next Steps: ➡️ Overpaying your CPA and the IRS? Learn how to stop it in this free training: https://go.phillipsbusinessgroup.com/registration