The Ryan Bakke Show

Ready to save $10k-$50k in taxes this year? Book a call here:► https://taxstrategy365.com/pod-appIn this episode, after leaving Deloitte at 23, I set out to help people who were the first in their families to build wealth. Three years later, I’m running two CPA firms with nearly 800 clients and reflecting on how much can change in just one trip around the sun. In this episode, I talk about the lessons that made me feel ten years wiser—lessons I picked up from mentors, clients, and experiences that pushed me to grow. I get into why urgency, focus, and being able to see both sides of an argument have been game changers for me.Timestamps:00:00:00 Intro and why I left Deloitte at 2300:00:32 From quitting corporate to owning two CPA firms00:01:25 Why I feel 10 years wiser in one year00:01:58 The meaning of “standing on the shoulders of giants”00:03:20 Investing in mentors and what it’s really worth00:04:24 Henry Ford, Thomas Edison, and learning from the top 0.3%00:06:32 Why in-person learning beats Zoom00:07:26 Joining Perry Belcher’s mastermind and doubling my business00:08:10 Acquiring a Beverly Hills CPA firm00:09:07 Traits of high-net-worth individuals00:10:43 The power of urgency and Parkinson’s Law00:12:16 Doing one thing exceptionally well00:13:32 The value of seeing both sides of an argument00:17:47 Overpriced vs. overkill: a pricing misconception00:20:38 What I learned from Robert Greene about storytelling00:23:32 Final reflection on growing wiser year over yearWant me to answer your real estate questions? Come to my next Ask Me Anything Q&A:► https://taxstrategy365.com/pod-amaLet's connect!► Instagram: https://www.instagram.com/ryanbakkecpa/► LinkedIn: https://www.linkedin.com/in/ryanbakkecpa/► Twitter: https://twitter.com/RyanBakkeCPA► Facebook: https://www.facebook.com/ryanbakkecpa► TikTok: https://www.tiktok.com/@ryanbakkecpa⁠*None of this is meant to be specific investment advice, it's for entertainment purposes only.

Ready to save $10k-$50k in taxes this year? Book a call here:► https://taxstrategy365.com/pod-appIn this episode, I dive into some of the most common tax questions I get from my communities, including how to properly report rental days for short-term rentals, the pros and cons of doing a cost segregation study, and how bonus depreciation really works. I also talk about when it makes sense to hire a CPA versus a tax strategist and explain the differences between the two. With examples from real clients and situations I’ve seen firsthand, I break down complex topics into practical insights.Timestamps:00:00:00 Intro 00:00:29 Communities I pull questions from 00:01:00 STR rental days – actual vs. available 00:02:12 Impact on deductions and personal use days 00:03:53 Lending implications of incorrect rental day reporting 00:04:33 Cost segregation vs. not doing it 00:05:36 Bonus depreciation explained 00:06:24 1031 exchange considerations and deadlines 00:07:51 Alternatives to 1031 exchanges 00:08:36 When to hire a CPA vs. a tax strategist 00:09:41 What tax strategists do differently 00:10:41 CPA vs. strategist – two skill sets 00:11:13 Why multiple businesses and properties need strategy 00:12:07 Outro Want me to answer your real estate questions? Come to my next Ask Me Anything Q&A:► https://taxstrategy365.com/pod-amaLet's connect!► Instagram: https://www.instagram.com/ryanbakkecpa/► LinkedIn: https://www.linkedin.com/in/ryanbakkecpa/► Twitter: https://twitter.com/RyanBakkeCPA► Facebook: https://www.facebook.com/ryanbakkecpa► TikTok: https://www.tiktok.com/@ryanbakkecpa⁠*None of this is meant to be specific investment advice, it's for entertainment purposes only.

Ready to save $10k-$50k in taxes this year? Book a call here:► https://taxstrategy365.com/pod-appIn this episode from the ATL Real Estate Conference, I share how I went from failing senior year math to becoming the youngest CPA in Illinois. I walk through the tax strategies I use with real estate investors, like cost segregation, depreciation, and how to take advantage of the short-term rental loophole. I also talk about mindset, making smart investment decisions, and avoiding common tax mistakes. Throughout the session, I share real examples and lessons from my own journey and client experiences.Timestamps:00:00:00 Intro 00:00:30 Writing your own story & becoming a CPA after failing math 00:01:45 Lessons from working at a pizza place 00:03:00 Working at Deloitte & shifting focus to helping everyday investors 00:04:05 First property purchase story and seller concessions 00:05:01 Psychology of loss and walking away from a Deloitte bonus 00:06:32 What you stand to gain vs. lose 00:07:13 Three biggest killers of wealth: taxes, inflation, indecision 00:08:21 Commonly missed tax deductions 00:09:26 Power of depreciation explained 00:10:52 Boosting cash-on-cash returns with cost segregation 00:12:33 Using losses to offset income from other sources 00:13:29 Personal tax return breakdown and tax strategy 00:15:13 Short-term rental loophole & qualifying tests 00:17:33 Real-life client success example 00:20:11 Net worth assessment and investing strategies by stage 00:22:40 Live-in flip and tax-free gains strategy 00:25:03 Rules for converting primary to rental 00:26:24 Cash-out refi vs. selling appreciated properties 00:27:00 Seller financing explained with real examples 00:30:46 Income shifting and Roth IRA strategy for kids 00:32:20 Never hold rentals in a corporation 00:32:50 The "Catch Me If You Can" mentorship analogy 00:33:53 Closing remarks Want me to answer your real estate questions? Come to my next Ask Me Anything Q&A:► https://taxstrategy365.com/pod-amaLet's connect!► Instagram: https://www.instagram.com/ryanbakkecpa/► LinkedIn: https://www.linkedin.com/in/ryanbakkecpa/► Twitter: https://twitter.com/RyanBakkeCPA► Facebook: https://www.facebook.com/ryanbakkecpa► TikTok: https://www.tiktok.com/@ryanbakkecpa⁠*None of this is meant to be specific investment advice, it's for entertainment purposes only.

Ready to save $10k-$50k in taxes this year? Book a call here:► https://taxstrategy365.com/pod-appIn this episode, I break down the differences between filing jointly and filing separately as a married couple. I go through real scenarios where filing separately can actually lead to better outcomes, especially when it comes to student loans, tax credits, and mortgage approvals. I explain how combining income can sometimes push you out of eligibility for certain benefits, and how separating returns might help reduce payments or qualify for better financing. I also touch on the trade-offs like higher tax brackets and added complexity that come with filing separately.Timestamps:00:00:00 Intro 00:00:39 When Filing Separately Saves More 00:01:26 Tax Credits and Deductions Overview 00:02:10 Real Example: Education Credit Eligibility 00:03:11 Using Software to Compare Filing Status 00:04:25 Student Loans and Income-Driven Repayment Plans 00:05:48 How Filing Separately Reduces Student Loan Payments 00:06:28 Mortgage Approval and Debt-to-Income Strategy 00:07:48 Real Estate and Loan Structuring Tips 00:09:00 Downsides of Filing Separately 00:10:00 Decision Framework for Filing Status 00:10:49 Real-World Case: Buying a Home with High Student Debt 00:11:25 Conclusion Want me to answer your real estate questions? Come to my next Ask Me Anything Q&A:► https://taxstrategy365.com/pod-amaLet's connect!► Instagram: https://www.instagram.com/ryanbakkecpa/► LinkedIn: https://www.linkedin.com/in/ryanbakkecpa/► Twitter: https://twitter.com/RyanBakkeCPA► Facebook: https://www.facebook.com/ryanbakkecpa► TikTok: https://www.tiktok.com/@ryanbakkecpa⁠*None of this is meant to be specific investment advice, it's for entertainment purposes only.

Ready to save $10k-$50k in taxes this year? Book a call here:► https://taxstrategy365.com/pod-appIn this episode, I answer real estate and tax questions from members of my RE Tax Prep and Tax Strategy 365 communities. I talk through the differences between DSCR and second home loans, and how they impact your tax situation and future financing options. I also explain how land-to-structure ratios affect depreciation and why location matters for tax benefits. Finally, I go over common mistakes investors make with LLC structuring and why it’s important to get it right from the start.Timestamps:00:00:00 Intro 00:00:40 First STR: DSCR vs. Second Home Loans 00:01:53 Understanding Tax Benefits Regardless of Loan Type 00:03:13 Thinking Two to Three Deals Ahead 00:05:11 Long-Term Strategy and Career Analogy 00:06:09 Why Net Worth Doesn’t Guarantee Loan Approval 00:07:45 Evaluating Depreciation by State and County 00:09:51 Using Assessor Sites to Understand Land vs. Building Value 00:11:19 Tax Benefits of Condos, Townhomes, and Different Markets 00:12:35 Entity Structuring: Single vs. Multi-Member LLCs 00:13:58 Pitfalls of Aggressive Legal Structures 00:15:31 Closing Remarks Want me to answer your real estate questions? Come to my next Ask Me Anything Q&A:► https://taxstrategy365.com/pod-amaLet's connect!► Instagram: https://www.instagram.com/ryanbakkecpa/► LinkedIn: https://www.linkedin.com/in/ryanbakkecpa/► Twitter: https://twitter.com/RyanBakkeCPA► Facebook: https://www.facebook.com/ryanbakkecpa► TikTok: https://www.tiktok.com/@ryanbakkecpa⁠*None of this is meant to be specific investment advice, it's for entertainment purposes only.

Ready to save $10k-$50k in taxes this year? Book a call here:► https://taxstrategy365.com/pod-appIf a real estate contract doesn’t have the right protections, you can end up overpaying, losing your deposit, or getting stuck with costly repairs. In this episode, I walk through the six key clauses I use in every deal to make sure I'm protected—no matter what market I’m in. I cover things like inspection contingencies, appraisal gaps, financing terms, permit and license transfers, and the “and/or assign” clause. I also share a few stories from my own deals where these clauses saved me thousands.Timestamps:00:00:00 Intro 00:00:27 Why contracts can make or break your deal 00:01:11 Understanding buyer vs. seller markets 00:02:13 How market conditions impact your negotiation leverage 00:03:14 Strategy if you're a buyer 00:04:13 Strategy if you're a seller 00:05:26 Inspection contingency explained 00:07:32 Real-world example: tree roots and sewer damage 00:08:01 Appraisal contingency breakdown 00:10:02 What is an appraisal gap and how to handle it 00:10:36 Financing contingency and rising interest rates 00:11:52 DSCR example and renegotiating purchase price 00:13:10 Why financing contingencies are critical 00:13:50 Permit and license transfer contingency 00:15:57 STR regulation example from Hot Springs, AR 00:16:19 Why this matters in regulated or urban markets 00:17:15 Assignment clause and “and/or assign” contracts 00:18:08 Contingency checklist for real estate deals Want me to answer your real estate questions? Come to my next Ask Me Anything Q&A:► https://taxstrategy365.com/pod-amaLet's connect!► Instagram: https://www.instagram.com/ryanbakkecpa/► LinkedIn: https://www.linkedin.com/in/ryanbakkecpa/► Twitter: https://twitter.com/RyanBakkeCPA► Facebook: https://www.facebook.com/ryanbakkecpa► TikTok: https://www.tiktok.com/@ryanbakkecpa⁠*None of this is meant to be specific investment advice, it's for entertainment purposes only.

Join John Bianchi, an Airbnb data guru, and Taylor Jones, an acquisitions specialist, as they delve into the savvy world of real estate tax strategies. They unpack the benefits of short-term rental tax loopholes and material participation, offering listeners invaluable tips to maximize tax savings. The duo shares insights on identifying optimal investment markets and the critical role of cost segregation. They also emphasize the importance of meticulous financial record-keeping to prepare for audits, ensuring your investments are both profitable and defendable.

Ready to save $10k-$50k in taxes this year? Book a call here:► https://taxstrategy365.com/pod-appIn this episode, I walk you through the exact steps to correctly set up an LLC in any state—and avoid the critical mistakes that make over half of DIY LLCs essentially worthless. I cover the full 7-step process, the difference between proper and flimsy asset protection, and the most common compliance missteps investors make. Whether you’re a new real estate investor or an experienced business owner looking to tighten up your asset protection strategy, this episode gives you everything you need to know to get your LLC done right the first time.Timestamps:00:00:00 – Intro: The difference between real asset protection and useless paperwork00:01:22 – Why LLCs offer protection, tax flexibility, and professionalism00:02:17 – Step 1: Name availability and selecting a registered agent00:02:57 – Step 2: Filing articles of organization and creating an operating agreement00:04:39 – Why poorly written operating agreements can cause major legal issues00:05:10 – Step 3: Getting an EIN and common filing mistakes to avoid00:05:47 – Step 4: Opening a business bank account00:06:41 – Step 5: State-specific requirements, annual filings, and fees00:07:39 – High-cost vs. low-cost LLC states: what to expect00:08:08 – Step 6: Common maintenance mistakes that lead to LLC “piercing”00:08:39 – The importance of proper documentation across multiple LLCs00:09:33 – Step 7: Updating records after life or business changes00:10:32 – When to hire a professional vs. DIY00:11:18 – Why professionals like doctors and CPAs often need PLLCs instead00:12:30 – Final thoughts: When to DIY and when to seek expert guidanceWant me to answer your real estate questions? Come to my next Ask Me Anything Q&A:► https://taxstrategy365.com/pod-amaLet's connect!► Instagram: https://www.instagram.com/ryanbakkecpa/► LinkedIn: https://www.linkedin.com/in/ryanbakkecpa/► Twitter: https://twitter.com/RyanBakkeCPA► Facebook: https://www.facebook.com/ryanbakkecpa► TikTok: https://www.tiktok.com/@ryanbakkecpa⁠*None of this is meant to be specific investment advice, it's for entertainment purposes only.

Ready to save $10k-$50k in taxes this year? Book a call here:► https://taxstrategy365.com/pod-appIn this episode, Ryan Bakke breaks down the key differences between LLCs and S Corporations—and why putting your rental real estate in an S Corp could cost you thousands in taxes. While S Corps are great for service-based businesses, Ryan walks through three major tax traps for real estate investors who use them. He also shares his recommended entity structure for those running both passive rental portfolios and active real estate businesses. If you’re a real estate investor or advisor trying to optimize your tax strategy, this episode is essential listening.Timestamps:00:00:00 – Intro: When an LLC beats an S Corp for real estate00:00:37 – Key differences: Tax treatment, liability, and ownership flexibility00:01:44 – Why S Corps are popular for service businesses (and when they work)00:02:29 – How an S Corp can save $9,000/year in self-employment tax00:03:43 – Why those savings don’t translate to real estate investing00:04:12 – S Corp disaster #1: Losing depreciation deductions00:05:40 – S Corp disaster #2: Refinance triggers a taxable event00:07:28 – What happens when you move property from an S Corp to personal name00:08:25 – S Corp disaster #3: Paying self-employment tax on passive income00:09:26 – When S Corps do make sense (flipping, development, active real estate)00:10:08 – Ryan’s recommended entity structure: Active vs. Passive buckets00:10:29 – Benefits of using LLCs for rentals: Depreciation, 1031s, flexibility00:11:11 – Recap: Avoiding tax nightmares with the right structureWant me to answer your real estate questions? Come to my next Ask Me Anything Q&A:► https://taxstrategy365.com/pod-amaLet's connect!► Instagram: https://www.instagram.com/ryanbakkecpa/► LinkedIn: https://www.linkedin.com/in/ryanbakkecpa/► Twitter: https://twitter.com/RyanBakkeCPA► Facebook: https://www.facebook.com/ryanbakkecpa► TikTok: https://www.tiktok.com/@ryanbakkecpa⁠*None of this is meant to be specific investment advice, it's for entertainment purposes only.

Ready to save $10k-$50k in taxes this year? Book a call here:► https://taxstrategy365.com/pod-appIn this episode, I break down one of the most powerful tax strategies available to real estate investors: the short-term rental (STR) tax loophole. I explain how investors who don’t qualify as real estate professionals can still use rental losses to offset W-2 and active business income—if they meet specific IRS requirements. I outline the two major tests you must pass (average stay and material participation), how to document them properly, and the massive tax savings this can unlock. If you want to pay less tax, accelerate your real estate goals, and avoid costly mistakes, this episode is your blueprint.Want me to answer your real estate questions? Come to my next Ask Me Anything Q&A:► https://taxstrategy365.com/pod-amaLet's connect!► Instagram: https://www.instagram.com/ryanbakkecpa/► LinkedIn: https://www.linkedin.com/in/ryanbakkecpa/► Twitter: https://twitter.com/RyanBakkeCPA► Facebook: https://www.facebook.com/ryanbakkecpa► TikTok: https://www.tiktok.com/@ryanbakkecpa⁠*None of this is meant to be specific investment advice, it's for entertainment purposes only.