The Ryan Bakke Show

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.

Ready to save $10k-$50k in taxes this year? Book a call here:► https://taxstrategy365.com/pod-appIn this episode, I talk with Chelsea Cutrer—former tech executive turned short-term rental queen—about her incredible journey from W2 to full-time real estate entrepreneur. Chelsea shares how she leveraged her design eye, sales background, and business instincts to build a growing STR portfolio in the competitive 30A market. We dive into the systems she uses to manage her own properties and her 20+ management clients, her take on revenue strategy, and how she’s already changing her family tree.Timestamps:00:00:00 – Intro and Transitioning from W2 tech job to full-time STR investor00:01:08 – Education, career at Dell, and early interest in real estate00:04:14 – How Chelsea’s mom inspired her real estate journey00:05:38 – Buying the first STR during COVID and the tax motivation behind it00:08:40 – What makes her listings outperform in 30A00:10:10 – The power of private beach access and listing clarity00:14:45 – What her current STR portfolio looks like00:16:26 – Markets she’s exploring next (like Cape San Blas)00:19:04 – From co-hosting to full management and revenue strategy00:20:21 – The biggest mistakes property managers make00:22:36 – How she prices for the off-season and fills gaps00:24:40 – Teaching her kids real estate and building generational wealth00:26:40 – Growth plans, S Corp planning, and how she found Ryan00:28:54 – Her top advice for anyone thinking about leaving their W2Want me to answer your questions live? 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 Client Success Spotlight episode, I sit down with Tanya and Arjun Bhasin to talk about how they built a top-performing short-term rental business while still working demanding tech jobs. From closing over $100k in bookings in their first month to building standout properties in competitive markets like Hot Springs, Arkansas and Newry, Maine — they share the systems, hospitality strategies, and risk-taking mindset that helped them scale fast. You’ll hear how they split responsibilities, fund their deals, and plan to keep building unique stays that land in the top 1%.Timestamps:00:00:00 – Intro + early investing background00:01:54 – Why they shifted from stocks to real estate00:04:09 – Tanya and Arjun’s complementary roles in their STR business00:05:38 – How they built a standout property in Hot Springs, AR00:07:27 – $100k in bookings in their first month live00:08:03 – Why hospitality and thoughtful touches drive repeat business00:09:28 – The mindset shift from tech careers to real estate freedom00:11:06 – Buying their first condo and discovering long-term wealth00:13:25 – Comparing Hot Springs and Newry, Maine markets00:14:33 – How they plan and build for top 1% performance00:15:46 – Markets they’re watching and planning to invest in next00:17:43 – How they financed their deals using second home loans00:20:45 – Why real estate gives you more control than stocks00:21:01 – Do they believe they’re changing their family tree?00:23:37 – Future plansWant me to answer your questions live? 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 explore the best strategies to save for your kids' college education, breaking down the pros and cons of 529 plans, Roth IRAs, and taxable brokerage accounts. From understanding state-specific tax advantages to leveraging the flexibility of brokerage accounts, I explain how to balance tax benefits, investment control, and flexibility. Whether you’re planning for scholarships, trade school, or a traditional college education, this episode provides actionable insights to build a smart, tax-efficient plan for your child's future.Timestamps:00:00:00 Intro: Why saving for kids' education is critical00:01:07 529 plans: State-specific options, pros, and cons00:03:49 Limitations of 529 plans and how to roll over unused funds to a Roth IRA00:06:41 Roth IRA for kids: Flexibility, benefits, and income requirements00:09:24 Why Roth IRAs are a powerful wealth-building tool for education and beyond00:10:19 Taxable brokerage accounts: The overlooked education savings option00:12:31 How gifting stocks to kids in low tax brackets can eliminate taxes00:13:25 Combining strategies: Creating a comprehensive savings plan00:14:05 Key factors: Tax benefits, flexibility, and control over investments00:15:00 Closing thoughts: How to align education savings with your financial goalsWant me to answer your questions live? 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/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? Book a call here:► https://taxstrategy365.com/pod-appIn this Client Success Spotlight episode, I talk with Carole Anderson—a former corporate accountant turned real estate investor—about how she built a thriving short-term rental portfolio after the sudden loss of her husband. Carole shares how she went from managing one Airbnb in her basement to running nine STRs, including owned properties, arbitrage units, and co-hosting arrangements. We also discuss the importance of clean books, building great systems, and how she’s turning her cost centers into profit centers by launching complementary businesses like cleaning and bookkeeping services. This is an inspiring story of resilience, resourcefulness, and long-term vision.Timestamps:00:00:00 – Carole’s first impression of Ryan’s boot camp00:00:44 – Carole’s education and accounting background00:01:54 – Leaving corporate America to pursue real estate full-time00:02:35 – How accounting skills helped her succeed in STRs00:04:50 – The story behind her very first Airbnb00:06:14 – Why her target guest isn’t who you’d expect00:08:28 – Carole’s current portfolio: 9 properties with diverse strategies00:09:34 – Funding her first STRs with life insurance after a family tragedy00:11:36 – How she scaled through smart investing and timing00:13:31 – Selling a non-compliant STR and reinvesting profits00:15:10 – Why she loves arbitrage (and how she pitches landlords)00:16:56 – Why she’s focused on her local Utah market00:18:38 – Turning her cleaning costs into a scalable business opportunity00:20:31 – How she found Ryan through YouTube and joined the boot camp00:23:39 – Why she’s switching from her local CPA to Ryan’s team00:26:18 – “Are you the one changing your family tree?” Carole’s powerful answer00:28:27 – Launching her direct booking site and plans to scale even furtherWant me to answer your questions live? 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 sit down with Kenny Bedwell from STR Insights to discuss actionable strategies for evaluating and acquiring profitable short-term rental properties. We dive deep into the importance of understanding market trends, creating a buy box for investments, and balancing risk with reward. From analyzing net income to navigating legislation risks and diversifying your portfolio, this conversation is packed with insights to help you grow your real estate investments. Whether you’re new to short-term rentals or looking to refine your strategy, this episode has valuable takeaways for everyone.Timestamps:00:00:00 Intro00:01:00 Kenny’s Background and Journey from W2 to Real Estate00:06:00 The Importance of Creating a Buy Box for Investments00:12:30 Breaking Down Risk: How Much Net Worth to Invest00:20:00 Diversification Strategies for Short-Term Rentals00:28:00 Avoiding Common Mistakes: Knowing What You Don’t Know00:36:00 Legislation Risks and How to Protect Your Portfolio00:44:00 Less Is More: Scaling with Quality Over Quantity00:52:00 Closing ThoughtsWant me to answer your questions live? Come to my next Ask Me Anything Q&A:► https://taxstrategy365.com/pod-amaLet's connect!► Instagram: ⁠https://www.instagram.com/learnlikeacpa/⁠► LinkedIn: ⁠https://www.linkedin.com/in/learnlikeacpa/⁠► Twitter: ⁠https://x.com/LearnLikeaCPA⁠► Facebook: ⁠https://www.facebook.com/learnlikeacpa⁠► Tiktok: ⁠https://www.tiktok.com/@learnlikeacpa⁠*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 sat down with Harrison Goldblatt, a real estate investor who has scaled to 60 units in just a few years. Harrison shares his journey from house-hacking his first property in Los Angeles to building a cash-flowing portfolio in Cleveland, Ohio. Along the way, he dives deep into the BRRRR method, leveraging value-add opportunities, and overcoming challenges in property management. Whether you're just starting out or looking to scale your portfolio, this conversation is packed with actionable strategies and valuable insights.Timestamps:00:00:00 – Intro00:01:00 – How Harrison Started in Real Estate: House Hacking in California00:05:47 – First Property Numbers and Lessons Learned00:09:09 – Scaling to 60 Units: Transitioning to Out-of-State Investing00:14:03 – Using the BRRRR Method to Lower Investment Barriers00:17:31 – Challenges with Refinancing and Avoiding Common Mistakes00:20:22 – Lessons Learned from a Bad Deal in Detroit00:24:13 – Importance of Mentors and Learning from Experienced Investors00:29:27 – Tax Strategies: Cash-Out Refinancing and Depreciation00:34:31 – Challenges of 1031 Exchanges and Managing Equity00:39:04 – Beginner’s Luck and the Risks of Overconfidence in Investing00:42:20 – Property Management Pitfalls and Avoiding Scams00:44:45 – Building a Community for Real Estate InvestorsWant me to answer your questions live? 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/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.