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A few people have mentioned the "step-up in basis" at death, and that's honestly the most important part of this whole strategy for the ultra-wealthy. Here's a simple example: Imagine a founder with $100 million in stock with a cost basis of $1 million. Option 1: Sell stock, pay ~24% capital gains tax (~$24 million), invest remaining $76 million Option 2: Borrow against stock at 4-5% interest, invest the borrowed money, never sell the stock In option 2, when they die, their heirs receive the stock with a stepped-up basis to current market value. They can sell immediately and pay ZERO capital gains tax on all that appreciation. This is why it's called "Buy, Borrow, Die" - the tax bill literally disappears at death!
This might be a dumb question, but what about estate taxes? Doesn't that just replace the capital gains tax problem when they die?
Great question! You're right that estate taxes can be significant, but there are key differences. First, the federal estate tax exemption is currently $13.6 million per person (so $27.2 million for married couples), meaning most people won't owe estate tax at all. Second, even for those who do owe estate tax, the rate applies to the entire estate value, but the heirs still get the stepped-up basis benefit on individual assets. So they might pay estate tax on the overall wealth, but they avoid capital gains tax on the appreciation when they eventually sell assets. For the ultra-wealthy, there are also sophisticated estate planning techniques (trusts, charitable strategies, etc.) that can minimize estate taxes while preserving the step-up benefit. The math usually still works out better than paying capital gains during their lifetime.
This whole discussion is fascinating but I think there's one crucial aspect we haven't fully addressed - the psychological and behavioral benefits of this strategy beyond just the math. When wealthy individuals use the "buy, borrow, die" approach, they're essentially forcing themselves to maintain a long-term investment mindset. If you know you can access liquidity through borrowing rather than selling, you're much less likely to panic-sell during market downturns or make emotional investment decisions. Think about it - how many regular investors sell their winners too early because they need cash? Or sell at the worst possible time during a market crash because they need liquidity? This strategy eliminates that temptation entirely. Plus, there's a compounding effect beyond just the tax savings. When you maintain your full position in appreciating assets while still having access to capital, you benefit from the full upside of market growth. Over decades, this behavioral advantage might be just as valuable as the tax optimization itself. It's not just a tax strategy - it's essentially a forced discipline mechanism that keeps you invested during both good times and bad.
That's a really insightful point about the behavioral aspect! I never thought about how this strategy basically removes the emotional decision-making from investing. As someone who's definitely been guilty of selling stocks when I needed cash (even when I knew it wasn't the optimal time), this makes a lot of sense. It's like having a forced "set it and forget it" approach, but with the flexibility to still access capital when needed. No more agonizing over whether to sell this stock or that one, or timing the market poorly because you need money for something. I'm curious though - for those of us without millions in assets, are there smaller-scale ways to implement this mindset? Maybe using something like a HELOC against home equity instead of selling investments for major purchases? The principle seems like it could apply even if the scale is different.
As someone who's been freelancing for about 4 years now, I want to emphasize something that really helped me early on: open a separate business checking account and savings account specifically for your freelance work. When that $3,800 payment comes in, immediately transfer about 30-35% to your tax savings account and don't touch it until tax time. I also recommend getting a business credit card for all your freelance expenses - makes tracking deductions so much easier at year end. And definitely keep digital copies of all receipts! I use my phone to snap photos of paper receipts and store them in a dedicated folder in Google Drive organized by month. One last tip: consider making your first estimated tax payment even if you're not sure you'll owe $1,000+ for the year. It's better to overpay slightly and get a refund than to underpay and face penalties. The IRS is much more forgiving if you overpay than if you underpay!
This is such solid advice! I wish someone had told me about the separate accounts when I started. I made the mistake of mixing everything together and it was a nightmare trying to figure out what was business vs personal when tax time came. One thing I'd add - when you set up that business checking account, see if your bank offers automatic transfers. I have mine set to automatically move 30% of any deposit over $500 into my tax savings account. Takes the willpower out of the equation because it happens before I even see the money in my main account. Has saved me from so many "oh I'll just borrow from my tax money this once" moments that never end well! The business credit card tip is gold too. Makes expense tracking almost automatic if you use it for everything work-related.
Great advice everyone! As someone who just went through my first year as a freelancer, I want to add one more thing that really helped me - keep a simple monthly income tracker. I created a basic spreadsheet where I log each payment as it comes in, what percentage I moved to taxes, and any major expenses for that month. This helped me in two ways: first, it made it super easy to calculate my quarterly estimated payments because I could see exactly how much I'd earned each quarter. Second, it helped me spot patterns in my income so I could better plan for slow months (which definitely happen in freelancing!). For your $3,800 project, I'd recommend setting aside $1,200-1,300 for taxes right when you get paid. It might seem like a lot, but trust me - you'll be so grateful you did when tax season rolls around. And if you end up overpaying, getting a refund is way better than owing money you don't have! Also, don't be afraid to ask other freelancers in your field about their tax strategies. Most of us have been where you are and are happy to share what we've learned. The freelancing community is generally pretty supportive once you get connected with the right people.
This is incredibly helpful, thank you! I love the idea of a monthly income tracker - that sounds way more manageable than trying to figure everything out all at once. Quick question: when you say set aside $1,200-1,300 for the $3,800, is that covering both federal and state taxes? I'm in Colorado so I know I'll have state taxes too. Also, did you find it better to make estimated payments right away or wait to see if you hit that $1,000 threshold first? I'm worried about overpaying but also don't want to get hit with penalties if I mess up the timing.
I'm dealing with a somewhat similar situation and wanted to share a perspective that might help with the mortgage aspect. When I went through underwriting last year after taking Section 179 depreciation, my loan officer suggested providing what she called a "business income normalization worksheet." This document showed my average business income over 3-5 years, then explained how the depreciation and recapture were timing differences that didn't reflect my actual earning capacity. We included the depreciation benefit I received in 2022 and the recapture I'd pay in 2023, essentially showing the net effect was much smaller than either number alone suggested. What really helped was demonstrating that my business cash flow remained strong throughout - the depreciation was a tax strategy, not a reflection of business performance. I provided bank statements showing consistent business deposits and highlighted that the vehicle sale actually improved our cash position. The underwriter appreciated seeing that we understood the tax implications upfront rather than being surprised by them. They ultimately approved the loan using an average income calculation that smoothed out the depreciation timing difference. One thing I'd recommend is getting pre-qualified with multiple lenders before you find a house. This gives you time to explain your situation without the pressure of a purchase contract deadline, and you can see which lenders are most comfortable with your scenario before you're committed to working with them.
This "business income normalization worksheet" approach sounds incredibly helpful! I'm new to dealing with depreciation recapture situations and the mortgage implications, but this thread has been so educational. Your point about demonstrating cash flow stability separate from the tax timing effects makes a lot of sense. I imagine lenders care more about your actual ability to make payments than the specific way depreciation moves numbers around on tax returns. The idea of getting pre-qualified with multiple lenders before house hunting is brilliant - it takes the pressure off and lets you find lenders who actually understand business tax strategies. Did you find that certain types of lenders (like portfolio lenders or community banks) were more willing to work with the normalization approach, or were most lenders pretty understanding once you explained it properly? Also, I'm curious about the timeframe - how far in advance did you start the pre-qualification process? I want to make sure I give myself enough time to find the right lender and get all the documentation together.
I'm in a very similar situation and this thread has been incredibly helpful! I took Section 179 depreciation on business equipment in 2022 and am now facing the recapture consequences after selling in 2023. One thing I learned from my tax attorney that might be relevant - if you're married filing jointly, the recapture income gets added to your combined income, which could potentially push you into a higher tax bracket than you were expecting. Make sure to run the numbers on your total household income when calculating the tax impact. Also, for the mortgage situation, I found that providing a simple one-page summary helped a lot. It showed: (1) Normal business income 2020-2021, (2) 2022 income with depreciation benefit, (3) 2023 projected income with recapture, and (4) 2024+ projected normalized income. This timeline format made it really clear to lenders that this was a temporary timing issue, not a fundamental change in our earning capacity. The key is being proactive about the narrative rather than letting lenders draw their own conclusions from the numbers alone.
Just want to add my experience as an S-Corp owner for 5+ years. What's worked for me is picking a consistent, reasonable monthly salary and sticking with it year-round, then taking quarterly distributions based on profitability. This makes everything cleaner for accounting and looks better to the IRS. For your situation this year, a one-time payment will work, but I'd strongly recommend getting on a regular schedule starting January. It's so much easier to manage cash flow when your owner compensation follows a predictable pattern. Also, the whole "reasonable salary" thing isn't as scary as it sounds. It doesn't mean you have to pay yourself market rate if your business can't afford it. It just means you can't take $1 in salary and $100K in distributions to avoid payroll taxes. As long as you're making a good faith effort to pay yourself fairly for your actual work, you'll be fine.
Thanks for this real-world advice! Would you recommend I go ahead with the lump sum now in December or just start fresh in January? My business has been profitable this year and I've been taking money out, just not as official salary. Trying to figure out the less risky approach.
Given that you've been taking money out and the business has been profitable, I'd definitely recommend doing the lump sum salary payment in December rather than waiting until January. Here's why: The IRS could potentially reclassify those distributions you've been taking as salary subject to payroll taxes if they determine you should have been paying yourself wages all along. By making a reasonable salary payment now, you're showing good faith effort to comply with S-Corp requirements. Calculate a reasonable annual salary based on what you'd pay someone else to do your job, then subtract any amounts you might have already run through payroll (sounds like zero in your case). Pay yourself that amount as salary in December with proper withholdings. Starting January, set up that regular monthly or bi-weekly schedule. The combination of addressing this year properly plus establishing a clean pattern going forward puts you in a much stronger position if there's ever any scrutiny. Your accountant can help you determine the right amount, but don't let perfect be the enemy of good - a documented, reasonable salary payment now is far better than nothing.
I'd definitely echo what others have said about making that lump sum payment in December rather than waiting. As someone who's dealt with similar timing issues, the IRS is generally more understanding about irregular payments in your first partial year as an S-Corp, especially if you document your reasoning well. One practical tip - when you calculate your reasonable salary amount, keep records of how you arrived at that number (industry research, comparable positions, etc.). I learned this the hard way when my accountant asked me to justify my salary decision later. Also, don't stress too much about the exact percentage split between salary and distributions. The key is that your salary reflects the value of services you actually perform for the business. If you're doing the work of a $60K employee in your industry, then that's a defensible salary regardless of what your total business income is. For next year, I'd suggest setting up automatic monthly salary payments through your payroll service. It makes everything so much cleaner and takes the guesswork out of compliance. You can always adjust the amount quarterly if your business performance changes significantly.
This is really helpful advice, especially about keeping documentation! I'm curious - when you say "industry research," what specific sources did you use to justify your salary decision? I'm in a pretty niche field and I'm worried I won't be able to find good comparable data to support whatever amount I choose. Did you use Bureau of Labor Statistics data, or something else? Also, how detailed does that documentation need to be - just a one-page summary or something more comprehensive?
Amun-Ra Azra
Ive seen this happen alot lately. The IRS is backed up worse than ever this year smh
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Brian Downey
That message is totally normal! It just means your return has moved from the initial received stage into actual processing. The bars on WMR often disappear when this happens - it's not a sign of any problems. Processing times can vary a lot this year, but most returns are getting processed within 21 days. Just keep checking periodically and you should see it update to approved soon!
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Emma Davis
•Thanks for the reassurance @Brian Downey! That's really helpful to know it's normal. I was starting to panic when the bars disappeared. Good to hear most are still processing within 21 days despite all the delays people are talking about 🤞
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