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5 contributions to 🏠 Lower Taxes w/ Ryan
W9/1099 - What's the risk?
I run a real estate company and we pay a lot of contractors for all types of things, work related to flips, inspections, running errands for us, surveys, etc. It's my understanding that any person/LLC we pay (Cash, Zelle/Quickpay, Check) over $600 that IS NOT an S/C Corp, should get a 1099. We've never done this. We still write those costs off as expenses (because they are), but we've never collected W9s from people we work with, or created a 1099. What's the risk here? It's my understanding that the risk here is that we can get penalized for this, but from a tax perspective, we can still write off those expenses and it doesn't affect anything there, is that right? From my understanding we'd have to issue 1099s to the following folks: General contractor Sub contractors Survey company Inspector Cleaner Anyone that gets over $600. Before we pay them, we should be asking for them to fill out a W9, right? Am I missing anything? I watched the video about this.
W9/1099 - What's the risk?
S Corp at Holding company level or can it be at LLC Level??
Have a question on LLC business structure, is an S-Corp supposed to be at the holding company level or individual LLC Level? I have two options here, I've confused myself - is one better than the other? I'd prefer to just have one holding company, ideally, but I'm not sure that's best and any tax implications, etc. surrounding that? My concern is that having mutliple S Corps would be a huge burden with payroll, etc. It would prob be easier to have all my active LLCs under one holding company that is an S Corp, and then all my passive LLCs that own properties, under another holding company that is passive. What's the right answer here? Whatever it is, would you mind explaining why one is better than the other?
S Corp at Holding company level or can it be at LLC Level??
0 likes • Mar 9
Thanks. So my holding company would then run payroll, and not the individual LLCs under the S Corp? There's 4 companies under Cerulean, it's a SMLLC. SSRC - 50K in profit Cash for Chicago Houses(partnership) - 600K in profit Windy City Construction (partnership) - 100K profit SFLP - 400K profit In this case, my S Corp would run payroll for a reasonable salary given these amounts. 800K in profit. I'd take a salary of 150K subject to 15.3%. The remaining 650K wouldn't be taxed for self employment taxes. Am I understanding that correctly? One other question, I'd get bank accounts for each LLC. To pay myself from the subsidiaries, the money would flow up through the LLC structure. So they'd transfer over to the operating account for Cerulean, and then out to me.
New member ~ Let's connect!
Hey Guys, Just joined. How do I know I'm old? On a Friday not, I'm on a website that teaches you how to lower your taxes ; ). In all seriousness, excited to be able to lower my tax liability. - Why do you want to save money on taxes? Not just “to save money” — but what does that money mean for your life? Saved money is investible money, and my goal is to be able to recycle money and plant those money trees that will allow my family to be taken care of forever. - Where are you right now in your journey? Just starting out? Own rentals? Flipping or doing STRs? I own a real estate wholesaling company, and I'm starting to do more flips this year. Hoping to do 10 flips personally and 8 flips through my company, which I own with a partner. I own 2 short term rentals and double digit units. - What’s your #1 challenge right now — your “big domino”? The one thing that would make everything else easier? - The #1 challenge is growing and scaling the wholesaling business. I've hired an employee and training her to take my spot so I can focus on bigger picture things within the business. - Thanks!
1 like • Jan 25
@Wendi Schneider Thanks Wendi - excited to get started
LLC, MMLLC, S Corp Setup
We often get asked the "how to" instructions for setting up entities. I filmed this short video to help with the process. Please comment any questions you might have.
LLC, MMLLC, S Corp Setup
0 likes • Jan 24
@Ryan Bakke, CPA Very helpful- have more questions on this. Would this be the correct way to set up an entity? This is how I'm thinking of setting up my business. I have a wholesaling company with a partner CFCH, but I'd also have wholesales in my own name (Anything named "B"). I'd have a flipping business, and a rental business, as would the business ("CFCH"). My understanding is that the wholesaling and flipping are active, and rentals are passive. I'd also like to wholesale to myself, and need those owned by different holding companies so hard money lenders don't flag it when I assign deals to myself for a profit. Would this be the most optimized way to set this up?
0 likes • Jan 25
Right so in the example above, HC1 and HC2 are S corps. HC3 wouldn't be an S corp since it's passive. Correct, on the partnership. So HC1 owns both my personal flipping business 100%, and then owns 50% ownership of our business with my partner. Same thing with HC2 which if wholesaling. The way it's set up currently would cover the HML. Everything would flow through one of the two wholesaling business, either the SMLLC or the business wholesaling company with I have 50% ownership of. Everything there is correct, right? @Ryan Bakke, CPA
HAPPY NEW YEAR 🎊🎈🎆
Thank you for your continued support and trust in our CPA firms.
0 likes • Jan 24
Happy New year!
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Brendan McElhaney
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11points to level up
@brendan-mcelhaney-9198
Brendan McElhaney | House Flipper | Wholesaler | Documenting my journey

Active 2d ago
Joined Jan 24, 2026
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