The Ryan Bakke Show

Ready to save $10k-$50k in taxes this year? https://taxstrategy365.com/yt-appIn this video, I’ll walk you through the exact tax traps most investors miss when selling an STR—and how to avoid them.You’ll learn:* The tax math no one talks about (spoiler: your loan balance doesn’t matter)* Why timing your sale matters just as much as your purchase* How equity before vs. after taxes works* The 4 different taxes you’ll face—and how to reduce or avoid them* Whether a 1031 exchange is worth the stress (and when a lazy 1031 is better)* The simple mistake that could make your entire tax deferral strategy pointlessI’ll even show you the one IRS form to check before you make a single decision.Whether you’re upgrading, offloading, or reallocating, this guide will show you how to exit without getting slammed by the IRS—and keep your momentum going with smart reinvestment strategies.Timestamps00:00 - Why investors lose money when they sell00:53 - Your loan balance doesn’t matter01:32 - This is your real starting number02:10 - The 4 taxes you’ll owe when you sell02:38 - Depreciation recapture03:28 - Capital gains tax03:46 - Net investment income tax04:00 - State income tax04:23 - Why most investors miss this04:51 - When to use a 1031 exchange05:24 - The “lazy” 1031 exchange06:16 - This IRS form changes everything07:05 - What to do before you sellLet's connect!► Instagram: https://www.instagram.com/ryanbakkecpa/► LinkedIn: https://www.linkedin.com/in/learnlikeacpa/► Twitter: https://x.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? https://taxstrategy365.com/yt-appIs it time to sell your underperforming short-term rental? Or should you keep holding?Most investors only look at cash-on-cash return. But return on equity? That’s where the real money is made. In this video, I’ll show you exactly how to calculate it — and how to decide whether to sell, refinance, or hold your STR for long-term growth.Watch until the end if you want to:✅ Understand the #1 mistake investors make when holding too long✅ Learn why an 8-year breakeven is your tipping point✅ See how to triple your portfolio with strategic exits✅ Get my personal framework for deciding when to redeploy your capital✅ Avoid the momentum-killing trap most investors fall into when they sellWhether you’re investing for cash flow or appreciation, this one decision can change the entire trajectory of your real estate portfolio. Run the numbers — then move with confidence.Timestamps:00:00 Why this one metric can change your entire investing strategy01:00 Cash-on-cash return explained (and when it fails you)02:00 The problem with rising equity and flat cash flow03:30 Return on equity math breakdown04:30 Why some properties lose money but make millionaires06:00 Cash flow investor vs appreciation investor08:00 When it’s time to sell — and when it’s a huge mistake09:00 How to exit without losing momentum10:00 Should you sell an underperforming STR?Let's connect!► Instagram: https://www.instagram.com/ryanbakkecpa/► LinkedIn: https://www.linkedin.com/in/learnlikeacpa/► Twitter: https://x.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.

Discover the journey of acquiring a $2.5 million accounting firm in Los Angeles. Explore the contrast between organic growth and the faster, scalable benefits of acquisition. Hear how the speaker shifted mindsets on firm ownership and the true challenges of growing a business. Learn about the costs of hiring versus the advantages of established teams. Plus, gain insights into the valuation uplift from acquisitions and the dynamics of trust and culture in business.

Ready to save $10k-$50k in taxes this year? Book a call here:► https://taxstrategy365.com/pod-appIn this episode, I break down how I analyze real estate deals using patterns, historical percentages, and what I call “return on hassle.” I share a story about a 16-unit property I almost bought to retire my mom and how a mentor helped me realize it wouldn’t work—just by looking at the percentages. I go deep into operating expense ratios, debt service thresholds, and how to factor in time and risk. I also touch on contracts, financing contingencies, and why I only move on deals that match my strike zone.Timestamps:00:00:00 Intro – why percentages never lie00:00:50 The 16-unit deal I almost bought to retire my mom00:02:15 Bringing in a mentor to review the numbers00:03:28 Learning to read patterns in properties and people00:04:11 Scarface quote and the power of percentages00:05:46 Ted Williams and only swinging at your pitch00:08:13 Applying the strike zone concept to investing00:09:14 Long-term rental analysis: revenue, OPEX, debt00:11:45 Utility setups and checking meters on multifamily00:13:54 Margin of error and padding your projections00:14:42 Short-term rental rules and the 15% revenue test00:16:16 Sneaky data hacks: talking to local co-hosts00:18:29 Evaluating money down vs. ROI on interest savings00:20:50 Guaranteed returns and the “return on hassle” concept00:23:00 FHA vs. conventional loan and PMI traps00:27:54 Why you must revisit the numbers at month 1600:29:04 Diagnosing why a deal is underperforming00:31:08 Pattern recognition and IRS fraud flags00:33:40 What’s included in operating expenses?00:36:28 Community, status, and why people never downgrade00:39:53 Appreciation markets vs. cash flow plays00:41:33 Writing contracts with flexibility: “and/or assign”00:44:05 Laying out all the skunks as a seller00:46:02 Contingencies: inspection, appraisal, financing, permits00:51:04 Buying the LLC to preserve STR permits00:54:20 DSCR strategy and using interest rate leverage00:56:05 Only swing at your pitch and know your advantage00:58:16 Speed, trust, and recognizing patterns in people01:00:32 Final thoughts and the value of knowing your safety netWant 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, 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.