Advizmo
@advizmo.bsky.social
Founder @Advizmo | Automating wealth-building
Ex-JP Morgan | Finance education
First app: auto cash management + investing
advizmo.com
Ex-JP Morgan | Finance education
First app: auto cash management + investing
advizmo.com
Taking a career break? You could pay $0 in capital gains tax. Most people miss this window and pay thousands later. Check out Advizmo for tax optimized auto-investing. advizmo.com
February 11, 2026 at 5:08 AM
Taking a career break? You could pay $0 in capital gains tax. Most people miss this window and pay thousands later. Check out Advizmo for tax optimized auto-investing. advizmo.com
Planning a low income year? You could pay 0% capital gains tax. Sell your stocks, immediately rebuy, reset your cost basis, tax free.
The 0% rate applies under $49,450 in taxable income. That's after the standard deduction.
advizmo.com for tax optimized investing
advizmo.substack.com/p/pay-0-capi...
The 0% rate applies under $49,450 in taxable income. That's after the standard deduction.
advizmo.com for tax optimized investing
advizmo.substack.com/p/pay-0-capi...
Pay 0% Capital Gains Tax During Your Low Income Year
If you're planning a sabbatical, career break, or gap year, you could erase thousands in future taxes. Here's how.
advizmo.substack.com
February 10, 2026 at 3:37 AM
Planning a low income year? You could pay 0% capital gains tax. Sell your stocks, immediately rebuy, reset your cost basis, tax free.
The 0% rate applies under $49,450 in taxable income. That's after the standard deduction.
advizmo.com for tax optimized investing
advizmo.substack.com/p/pay-0-capi...
The 0% rate applies under $49,450 in taxable income. That's after the standard deduction.
advizmo.com for tax optimized investing
advizmo.substack.com/p/pay-0-capi...
Using your brokerage defaults when selling stocks could be costing 1-2% per year in after-tax returns
Tax-optimized selling + tax-loss harvesting fixes this Many investors don't use either & are missing thousands in returns
Advizmo automates both.
advizmo.substack.com/p/add-1-2-to...
Tax-optimized selling + tax-loss harvesting fixes this Many investors don't use either & are missing thousands in returns
Advizmo automates both.
advizmo.substack.com/p/add-1-2-to...
Add 1-2% To Your Annual After Tax Returns With Tax Harvesting and Tax Optimized Selling
Many investors are reducing their overall returns when they sell stocks. Here's how tax-optimized selling and tax-loss harvesting work together to boost your after-tax returns by 1-2% per year.
advizmo.substack.com
February 7, 2026 at 7:12 PM
Using your brokerage defaults when selling stocks could be costing 1-2% per year in after-tax returns
Tax-optimized selling + tax-loss harvesting fixes this Many investors don't use either & are missing thousands in returns
Advizmo automates both.
advizmo.substack.com/p/add-1-2-to...
Tax-optimized selling + tax-loss harvesting fixes this Many investors don't use either & are missing thousands in returns
Advizmo automates both.
advizmo.substack.com/p/add-1-2-to...
When to pay capital gains now including the 0% capital gains tax in low income years.
4 situations to SELL and pay taxes NOW:
1 You're in the 0% bracket ($49k single/$99k married)
2 Low earner now, high earner later
3 Tax rates rising
4 Moving states
advizmo.substack.com/p/4-situtati...
4 situations to SELL and pay taxes NOW:
1 You're in the 0% bracket ($49k single/$99k married)
2 Low earner now, high earner later
3 Tax rates rising
4 Moving states
advizmo.substack.com/p/4-situtati...
4 Situtations When You Should Pay Capital Gains Taxes NOW (Including 0% Tax in Low Income Years)
Almost always defer taxes as long as possible. But here are 4 situations where that advice costs you money, and what to do instead.
advizmo.substack.com
February 2, 2026 at 8:34 PM
When to pay capital gains now including the 0% capital gains tax in low income years.
4 situations to SELL and pay taxes NOW:
1 You're in the 0% bracket ($49k single/$99k married)
2 Low earner now, high earner later
3 Tax rates rising
4 Moving states
advizmo.substack.com/p/4-situtati...
4 situations to SELL and pay taxes NOW:
1 You're in the 0% bracket ($49k single/$99k married)
2 Low earner now, high earner later
3 Tax rates rising
4 Moving states
advizmo.substack.com/p/4-situtati...
What is tax optimized selling of stocks? You may be overpaying taxes every time you sell stock.
Here's why: Every purchase creates a "tax lot" with its own cost basis. Selling the wrong shares = unnecessary tax bill.
advizmo.substack.com/p/what-is-ta...
Here's why: Every purchase creates a "tax lot" with its own cost basis. Selling the wrong shares = unnecessary tax bill.
advizmo.substack.com/p/what-is-ta...
What Is Tax Optimized Selling Of Stocks and Why Is It Important?
How tax-optimized selling can prevent thousands in unnecessary taxes
advizmo.substack.com
January 31, 2026 at 8:50 PM
What is tax optimized selling of stocks? You may be overpaying taxes every time you sell stock.
Here's why: Every purchase creates a "tax lot" with its own cost basis. Selling the wrong shares = unnecessary tax bill.
advizmo.substack.com/p/what-is-ta...
Here's why: Every purchase creates a "tax lot" with its own cost basis. Selling the wrong shares = unnecessary tax bill.
advizmo.substack.com/p/what-is-ta...
When investments are down, losing money twice: once on the investment, again by not harvesting tax benefits
Tax loss harvesting gives 3 benefits
1 Deduct $3k from income yearly
2 Offset ALL gains dollar-for-dollar
3 Carry losses forward
Automatic w/ advizmo.com
advizmo.substack.com/p/tax-loss-h...
Tax loss harvesting gives 3 benefits
1 Deduct $3k from income yearly
2 Offset ALL gains dollar-for-dollar
3 Carry losses forward
Automatic w/ advizmo.com
advizmo.substack.com/p/tax-loss-h...
Tax Loss Harvesting: Your Investment Losses Are Worth Money. Here's How to Use Them.
Smart investors turn losses into tax savings that compound over time. Here's the strategy most people know, but many time do not execute.
advizmo.substack.com
January 28, 2026 at 10:31 PM
When investments are down, losing money twice: once on the investment, again by not harvesting tax benefits
Tax loss harvesting gives 3 benefits
1 Deduct $3k from income yearly
2 Offset ALL gains dollar-for-dollar
3 Carry losses forward
Automatic w/ advizmo.com
advizmo.substack.com/p/tax-loss-h...
Tax loss harvesting gives 3 benefits
1 Deduct $3k from income yearly
2 Offset ALL gains dollar-for-dollar
3 Carry losses forward
Automatic w/ advizmo.com
advizmo.substack.com/p/tax-loss-h...
3 Things To Do With Excess Cash In Checking.
Leaving $10K in 0% checking = losing $700/year
That's $28K over 20 years you'll never get back
3 better options:
1 High-yield savings
2 Money market funds
3 Index funds
Check out Advizmo to automate all this! advizmo.substack.com/p/3-things-t...
Leaving $10K in 0% checking = losing $700/year
That's $28K over 20 years you'll never get back
3 better options:
1 High-yield savings
2 Money market funds
3 Index funds
Check out Advizmo to automate all this! advizmo.substack.com/p/3-things-t...
3 Things To Do With Your Excess Cash In Checking
How much cash do you have sitting in your checking account right now?
advizmo.substack.com
January 27, 2026 at 4:14 AM
3 Things To Do With Excess Cash In Checking.
Leaving $10K in 0% checking = losing $700/year
That's $28K over 20 years you'll never get back
3 better options:
1 High-yield savings
2 Money market funds
3 Index funds
Check out Advizmo to automate all this! advizmo.substack.com/p/3-things-t...
Leaving $10K in 0% checking = losing $700/year
That's $28K over 20 years you'll never get back
3 better options:
1 High-yield savings
2 Money market funds
3 Index funds
Check out Advizmo to automate all this! advizmo.substack.com/p/3-things-t...
Tax Lots Explained And Why Important When Selling Stocks
Every time you buy stocks = new tax lot
When you sell = which lots you choose = your tax bill
FIFO vs LIFO on the same sale? $1,000+ difference.
Advizmo automates this optimization for everyone. advizmo.substack.com/p/tax-lots-e...
Every time you buy stocks = new tax lot
When you sell = which lots you choose = your tax bill
FIFO vs LIFO on the same sale? $1,000+ difference.
Advizmo automates this optimization for everyone. advizmo.substack.com/p/tax-lots-e...
Tax Lots Explained: What Is A Tax Lot and Why Is It Important When Selling Your Stocks?
Every time you sell stocks, you choose which "tax lots" to sell. Choose wrong, and the IRS gets thousands more than necessary.
advizmo.substack.com
January 25, 2026 at 6:54 PM
Tax Lots Explained And Why Important When Selling Stocks
Every time you buy stocks = new tax lot
When you sell = which lots you choose = your tax bill
FIFO vs LIFO on the same sale? $1,000+ difference.
Advizmo automates this optimization for everyone. advizmo.substack.com/p/tax-lots-e...
Every time you buy stocks = new tax lot
When you sell = which lots you choose = your tax bill
FIFO vs LIFO on the same sale? $1,000+ difference.
Advizmo automates this optimization for everyone. advizmo.substack.com/p/tax-lots-e...
7 financial moves in January to take action on:
1 Max IRA by April 15th, but sooner the better
2 Harvest tax losses
3 Increase 401k contributions
4 Review last year spending find the leaks fix them
5 Plan big purchases & emergency fund
6 Automate w/ Advizmo
advizmo.substack.com/p/7-personal...
1 Max IRA by April 15th, but sooner the better
2 Harvest tax losses
3 Increase 401k contributions
4 Review last year spending find the leaks fix them
5 Plan big purchases & emergency fund
6 Automate w/ Advizmo
advizmo.substack.com/p/7-personal...
7 Personal Finance Moves to Make in January
Start the year right with these essential money moves that will set you up for financial success in 2025
advizmo.substack.com
January 23, 2026 at 8:01 PM
7 financial moves in January to take action on:
1 Max IRA by April 15th, but sooner the better
2 Harvest tax losses
3 Increase 401k contributions
4 Review last year spending find the leaks fix them
5 Plan big purchases & emergency fund
6 Automate w/ Advizmo
advizmo.substack.com/p/7-personal...
1 Max IRA by April 15th, but sooner the better
2 Harvest tax losses
3 Increase 401k contributions
4 Review last year spending find the leaks fix them
5 Plan big purchases & emergency fund
6 Automate w/ Advizmo
advizmo.substack.com/p/7-personal...
Will investing short-term increase taxes?
Actually creates tax loss harvesting opptys
Here's why to invest even if need money in few weeks
Paying taxes means you MADE money
Don't sell what you just bought. Sell tax-efficient positions=tax loss harvesting all year
advizmo.substack.com/p/wont-inves...
Actually creates tax loss harvesting opptys
Here's why to invest even if need money in few weeks
Paying taxes means you MADE money
Don't sell what you just bought. Sell tax-efficient positions=tax loss harvesting all year
advizmo.substack.com/p/wont-inves...
"Won't Investing Short-Term Increase My Taxes?" Actually It Creates Natural Tax Loss Harvesting Opportunities
Why investing even short-term funds is a win-win: you earn returns on idle cash, and regular withdrawals naturally harvest tax losses throughout the year.
advizmo.substack.com
January 23, 2026 at 7:59 PM
Will investing short-term increase taxes?
Actually creates tax loss harvesting opptys
Here's why to invest even if need money in few weeks
Paying taxes means you MADE money
Don't sell what you just bought. Sell tax-efficient positions=tax loss harvesting all year
advizmo.substack.com/p/wont-inves...
Actually creates tax loss harvesting opptys
Here's why to invest even if need money in few weeks
Paying taxes means you MADE money
Don't sell what you just bought. Sell tax-efficient positions=tax loss harvesting all year
advizmo.substack.com/p/wont-inves...
Taxes can hurt or boost investments
8 concepts
1 Tax loss harvesting
2 Long vs short-term gains-15% vs 37%
3 Wash sales(30-day rule)
4 Asset location
5 Time gains
6 NIIT-extra 3.8% for high earners
7 Tax-efficient funds
8 State taxes
We automate this at Advizmo advizmo.substack.com/p/how-import...
8 concepts
1 Tax loss harvesting
2 Long vs short-term gains-15% vs 37%
3 Wash sales(30-day rule)
4 Asset location
5 Time gains
6 NIIT-extra 3.8% for high earners
7 Tax-efficient funds
8 State taxes
We automate this at Advizmo advizmo.substack.com/p/how-import...
Advizmo
advizmo.com
December 19, 2025 at 5:21 AM
Taxes can hurt or boost investments
8 concepts
1 Tax loss harvesting
2 Long vs short-term gains-15% vs 37%
3 Wash sales(30-day rule)
4 Asset location
5 Time gains
6 NIIT-extra 3.8% for high earners
7 Tax-efficient funds
8 State taxes
We automate this at Advizmo advizmo.substack.com/p/how-import...
8 concepts
1 Tax loss harvesting
2 Long vs short-term gains-15% vs 37%
3 Wash sales(30-day rule)
4 Asset location
5 Time gains
6 NIIT-extra 3.8% for high earners
7 Tax-efficient funds
8 State taxes
We automate this at Advizmo advizmo.substack.com/p/how-import...
Need to sell/rebalance your portfolio right away? Taxes matter.
The order you sell can save thousands.
Tax-smart sequence:
1 Harvest losses
2 Add new money to underweight positions
3 Rebalance in IRA (tax-free)
4 Sell strategically in taxable accounts
advizmo.substack.com/p/need-to-se...
The order you sell can save thousands.
Tax-smart sequence:
1 Harvest losses
2 Add new money to underweight positions
3 Rebalance in IRA (tax-free)
4 Sell strategically in taxable accounts
advizmo.substack.com/p/need-to-se...
Need to Sell or Rebalance Right Away? The Order You Sell Matters
A tax-smart rebalancing sequence that you should consider, especially when you're in a hurry
advizmo.substack.com
December 11, 2025 at 4:38 PM
Need to sell/rebalance your portfolio right away? Taxes matter.
The order you sell can save thousands.
Tax-smart sequence:
1 Harvest losses
2 Add new money to underweight positions
3 Rebalance in IRA (tax-free)
4 Sell strategically in taxable accounts
advizmo.substack.com/p/need-to-se...
The order you sell can save thousands.
Tax-smart sequence:
1 Harvest losses
2 Add new money to underweight positions
3 Rebalance in IRA (tax-free)
4 Sell strategically in taxable accounts
advizmo.substack.com/p/need-to-se...
Should you rebalance your portfolio all at once or over time? Mistake: Selling everything at once.
The fix: Rebalance over 6-12 months.
Example: $50K rebalanced instantly = $10K tax. Same rebalance over 6 months with tax-loss harvesting = less tax.
Be patient. advizmo.substack.com/p/should-you...
The fix: Rebalance over 6-12 months.
Example: $50K rebalanced instantly = $10K tax. Same rebalance over 6 months with tax-loss harvesting = less tax.
Be patient. advizmo.substack.com/p/should-you...
Should You Rebalance Your Portfolio All At Once or Over Time?
Many investors get this wrong and pay thousands in unnecessary taxes. Here's a smarter approach.
advizmo.substack.com
December 5, 2025 at 7:55 PM
Should you rebalance your portfolio all at once or over time? Mistake: Selling everything at once.
The fix: Rebalance over 6-12 months.
Example: $50K rebalanced instantly = $10K tax. Same rebalance over 6 months with tax-loss harvesting = less tax.
Be patient. advizmo.substack.com/p/should-you...
The fix: Rebalance over 6-12 months.
Example: $50K rebalanced instantly = $10K tax. Same rebalance over 6 months with tax-loss harvesting = less tax.
Be patient. advizmo.substack.com/p/should-you...
When should I time tax loss harvesting? Once per year or more often? Tax loss harvest more frequently especially during volatile markets. Why? Volatility = opportunity.
Even when S&P is up 20%, individual stocks could be down. Those are tax-saving opportunities.
advizmo.substack.com/p/when-shoul...
Even when S&P is up 20%, individual stocks could be down. Those are tax-saving opportunities.
advizmo.substack.com/p/when-shoul...
When Should I Time Tax Loss Harvesting? Once Per Year or More Often?
The more frequently you check your portfolio to tax loss harvest, the more opportunities you will find. Especially during volatile markets.
advizmo.substack.com
November 29, 2025 at 5:09 AM
When should I time tax loss harvesting? Once per year or more often? Tax loss harvest more frequently especially during volatile markets. Why? Volatility = opportunity.
Even when S&P is up 20%, individual stocks could be down. Those are tax-saving opportunities.
advizmo.substack.com/p/when-shoul...
Even when S&P is up 20%, individual stocks could be down. Those are tax-saving opportunities.
advizmo.substack.com/p/when-shoul...
When's the best time to sell your gains?
Answer: When you have losses to offset them.
Tax-loss harvesting lets you:
-Offset gains
-Deduct $3K/year from income
-Carry forward losses
You can't control the market. You have more control over your taxes.
www.tiktok.com/@advizmo/pho...
Answer: When you have losses to offset them.
Tax-loss harvesting lets you:
-Offset gains
-Deduct $3K/year from income
-Carry forward losses
You can't control the market. You have more control over your taxes.
www.tiktok.com/@advizmo/pho...
TikTok - Make Your Day
www.tiktok.com
November 24, 2025 at 4:57 PM
When's the best time to sell your gains?
Answer: When you have losses to offset them.
Tax-loss harvesting lets you:
-Offset gains
-Deduct $3K/year from income
-Carry forward losses
You can't control the market. You have more control over your taxes.
www.tiktok.com/@advizmo/pho...
Answer: When you have losses to offset them.
Tax-loss harvesting lets you:
-Offset gains
-Deduct $3K/year from income
-Carry forward losses
You can't control the market. You have more control over your taxes.
www.tiktok.com/@advizmo/pho...
Strategically Sell Your Gains (Tax-Smart Approach)
The Problem: When you sell gains in your taxable brokerage account, you trigger capital gains taxes
The Solution: Proactive tax-loss harvesting combined with patience.
Try not to be in a rush to sell.
advizmo.substack.com/p/strategica...
The Problem: When you sell gains in your taxable brokerage account, you trigger capital gains taxes
The Solution: Proactive tax-loss harvesting combined with patience.
Try not to be in a rush to sell.
advizmo.substack.com/p/strategica...
Strategically Sell Your Gains: A Tax-Smart Perspective
Proactive tax-loss harvesting and patience are key
advizmo.substack.com
November 22, 2025 at 6:48 AM
Strategically Sell Your Gains (Tax-Smart Approach)
The Problem: When you sell gains in your taxable brokerage account, you trigger capital gains taxes
The Solution: Proactive tax-loss harvesting combined with patience.
Try not to be in a rush to sell.
advizmo.substack.com/p/strategica...
The Problem: When you sell gains in your taxable brokerage account, you trigger capital gains taxes
The Solution: Proactive tax-loss harvesting combined with patience.
Try not to be in a rush to sell.
advizmo.substack.com/p/strategica...
When should you SELL your stocks?
Many sell for the wrong reasons
8 LEGITIMATE reasons:
1 Rebalancing
2 Age-based adjustments
3 Strategic shifts
4 Tax-loss harvesting
5 Life events
6 Reduce concentrated positions
7 Investment thesis changed
8 Retirement income
advizmo.substack.com/p/when-is-it...
Many sell for the wrong reasons
8 LEGITIMATE reasons:
1 Rebalancing
2 Age-based adjustments
3 Strategic shifts
4 Tax-loss harvesting
5 Life events
6 Reduce concentrated positions
7 Investment thesis changed
8 Retirement income
advizmo.substack.com/p/when-is-it...
When Is It Smart To Sell Your Stocks? 8 Legitimate Reasons
Many investors sell for the wrong reasons. Here's when selling is actually smart, strategic, and part of a disciplined investment approach.
advizmo.substack.com
November 18, 2025 at 7:14 PM
When should you SELL your stocks?
Many sell for the wrong reasons
8 LEGITIMATE reasons:
1 Rebalancing
2 Age-based adjustments
3 Strategic shifts
4 Tax-loss harvesting
5 Life events
6 Reduce concentrated positions
7 Investment thesis changed
8 Retirement income
advizmo.substack.com/p/when-is-it...
Many sell for the wrong reasons
8 LEGITIMATE reasons:
1 Rebalancing
2 Age-based adjustments
3 Strategic shifts
4 Tax-loss harvesting
5 Life events
6 Reduce concentrated positions
7 Investment thesis changed
8 Retirement income
advizmo.substack.com/p/when-is-it...
When should you ACTUALLY sell your stocks?
8 legitimate reasons to sell:
1 Rebalancing
2 Age-based adjustments
3 Strategy changes
4 Tax-loss harvesting
5 Life events needing cash
6 Reducing concentrated positions
7 Investment thesis changed
8 Retirement income
advizmo.substack.com/p/when-shoul...
8 legitimate reasons to sell:
1 Rebalancing
2 Age-based adjustments
3 Strategy changes
4 Tax-loss harvesting
5 Life events needing cash
6 Reducing concentrated positions
7 Investment thesis changed
8 Retirement income
advizmo.substack.com/p/when-shoul...
When Should You Actually Sell Your Stocks?
Eight legitimate reasons to sell. And why timing the market isn't one of them
advizmo.substack.com
November 17, 2025 at 8:47 PM
When should you ACTUALLY sell your stocks?
8 legitimate reasons to sell:
1 Rebalancing
2 Age-based adjustments
3 Strategy changes
4 Tax-loss harvesting
5 Life events needing cash
6 Reducing concentrated positions
7 Investment thesis changed
8 Retirement income
advizmo.substack.com/p/when-shoul...
8 legitimate reasons to sell:
1 Rebalancing
2 Age-based adjustments
3 Strategy changes
4 Tax-loss harvesting
5 Life events needing cash
6 Reducing concentrated positions
7 Investment thesis changed
8 Retirement income
advizmo.substack.com/p/when-shoul...
Should you sell stocks in your IRA or 401(k) to time the market?
Even without capital gains taxes, the answer is still no. You need to be right TWICE, when to sell AND when to buy back in.
Market timing is hard with or without taxes. Stay disciplined and patient.
advizmo.substack.com/p/should-i-s...
Even without capital gains taxes, the answer is still no. You need to be right TWICE, when to sell AND when to buy back in.
Market timing is hard with or without taxes. Stay disciplined and patient.
advizmo.substack.com/p/should-i-s...
Should I Sell Stocks in My IRA or 401(k) to Time the Market?
Tax-free trading sounds tempting, but market timing is still a losing game—even in retirement accounts.
advizmo.substack.com
November 14, 2025 at 4:57 PM
Should you sell stocks in your IRA or 401(k) to time the market?
Even without capital gains taxes, the answer is still no. You need to be right TWICE, when to sell AND when to buy back in.
Market timing is hard with or without taxes. Stay disciplined and patient.
advizmo.substack.com/p/should-i-s...
Even without capital gains taxes, the answer is still no. You need to be right TWICE, when to sell AND when to buy back in.
Market timing is hard with or without taxes. Stay disciplined and patient.
advizmo.substack.com/p/should-i-s...
Should I try to time the market in my IRA since there are no capital gains taxes?
Short answer: not recommended
The fundamental problem. You need to be right TWICE: 1) when to sell and 2) when to buy back in
Miss either one & you underperform buy & hold
advizmo.substack.com/p/should-i-s...
Short answer: not recommended
The fundamental problem. You need to be right TWICE: 1) when to sell and 2) when to buy back in
Miss either one & you underperform buy & hold
advizmo.substack.com/p/should-i-s...
Should I Sell Stocks In My IRA If I Am Worried About the Market Going Down? (No Capital Gains Taxes)
No capital gains taxes doesn't mean market timing works. You still need to time the market correctly twice, which is extremely difficult.
advizmo.substack.com
November 13, 2025 at 6:17 AM
Should I try to time the market in my IRA since there are no capital gains taxes?
Short answer: not recommended
The fundamental problem. You need to be right TWICE: 1) when to sell and 2) when to buy back in
Miss either one & you underperform buy & hold
advizmo.substack.com/p/should-i-s...
Short answer: not recommended
The fundamental problem. You need to be right TWICE: 1) when to sell and 2) when to buy back in
Miss either one & you underperform buy & hold
advizmo.substack.com/p/should-i-s...
Be careful selling gains to time the market ⚠️
When you sell stocks with gains, you pay tax immediately. The market must drop MORE than your tax hit just to break even.
Example: 20% tax on a 100% gain = market must drop 10%
Your winners are most expensive to sell. advizmo.substack.com/p/considerin...
When you sell stocks with gains, you pay tax immediately. The market must drop MORE than your tax hit just to break even.
Example: 20% tax on a 100% gain = market must drop 10%
Your winners are most expensive to sell. advizmo.substack.com/p/considerin...
Considering Selling Gains To Time The Market? Be Careful. The Tax Math On Why Timing the Market Almost Never Works
When you sell stocks with gains to avoid a downturn, the market needs to drop by more than the tax you pay to break even.
advizmo.substack.com
November 9, 2025 at 5:56 PM
Be careful selling gains to time the market ⚠️
When you sell stocks with gains, you pay tax immediately. The market must drop MORE than your tax hit just to break even.
Example: 20% tax on a 100% gain = market must drop 10%
Your winners are most expensive to sell. advizmo.substack.com/p/considerin...
When you sell stocks with gains, you pay tax immediately. The market must drop MORE than your tax hit just to break even.
Example: 20% tax on a 100% gain = market must drop 10%
Your winners are most expensive to sell. advizmo.substack.com/p/considerin...
Be careful selling stocks with gains to time the market. The math proves why this almost never works.
Capital gains taxes mean the market needs to drop 5%-13%+ just for you to break even. And you still need to perfectly time buying back in.
advizmo.substack.com/p/be-careful...
Capital gains taxes mean the market needs to drop 5%-13%+ just for you to break even. And you still need to perfectly time buying back in.
advizmo.substack.com/p/be-careful...
Be careful selling stocks to time the market. The math proves why this is difficult to do and make money
Capital gains taxes mean the market needs to drop 6-13%+ just for you to break even. And you still need to perfectly time buying back in.
advizmo.substack.com
November 7, 2025 at 9:32 PM
Be careful selling stocks with gains to time the market. The math proves why this almost never works.
Capital gains taxes mean the market needs to drop 5%-13%+ just for you to break even. And you still need to perfectly time buying back in.
advizmo.substack.com/p/be-careful...
Capital gains taxes mean the market needs to drop 5%-13%+ just for you to break even. And you still need to perfectly time buying back in.
advizmo.substack.com/p/be-careful...
Rebalancing your portfolio? Don't trigger unnecessary taxes.
Golden Rules:
1. Sell losses first, avoid gains
2. If you must sell gains, sell long-term before short-term
Why?
Long-term gains: 0-20% tax
Short-term gains: 22-37% tax
Tax planning saves thousands
advizmo.substack.com/p/what-to-se...
Golden Rules:
1. Sell losses first, avoid gains
2. If you must sell gains, sell long-term before short-term
Why?
Long-term gains: 0-20% tax
Short-term gains: 22-37% tax
Tax planning saves thousands
advizmo.substack.com/p/what-to-se...
What To Sell When Rebalancing Your Portfolio: The Tax-Smart Approach
Why selling the wrong positions when rebalancing can cost you thousands in unnecessary taxes and how to avoid these expensive mistakes
advizmo.substack.com
November 1, 2025 at 7:24 PM
Rebalancing your portfolio? Don't trigger unnecessary taxes.
Golden Rules:
1. Sell losses first, avoid gains
2. If you must sell gains, sell long-term before short-term
Why?
Long-term gains: 0-20% tax
Short-term gains: 22-37% tax
Tax planning saves thousands
advizmo.substack.com/p/what-to-se...
Golden Rules:
1. Sell losses first, avoid gains
2. If you must sell gains, sell long-term before short-term
Why?
Long-term gains: 0-20% tax
Short-term gains: 22-37% tax
Tax planning saves thousands
advizmo.substack.com/p/what-to-se...
Worried the market might drop?
Rebalance, don't rush to sell based on headlines.
Rebalancing = strategic repositioning based on YOUR goals
⚠️ Timing the market almost never works
Be thoughtful about WHICH stocks to sell and in WHAT order)
advizmo.substack.com/p/worried-ab...
Rebalance, don't rush to sell based on headlines.
Rebalancing = strategic repositioning based on YOUR goals
⚠️ Timing the market almost never works
Be thoughtful about WHICH stocks to sell and in WHAT order)
advizmo.substack.com/p/worried-ab...
Worried About a Market Drop? It's Time to Rebalance
How to strategically adjust your portfolio when market concerns arise—without trying to time the market
advizmo.substack.com
October 30, 2025 at 12:33 AM
Worried the market might drop?
Rebalance, don't rush to sell based on headlines.
Rebalancing = strategic repositioning based on YOUR goals
⚠️ Timing the market almost never works
Be thoughtful about WHICH stocks to sell and in WHAT order)
advizmo.substack.com/p/worried-ab...
Rebalance, don't rush to sell based on headlines.
Rebalancing = strategic repositioning based on YOUR goals
⚠️ Timing the market almost never works
Be thoughtful about WHICH stocks to sell and in WHAT order)
advizmo.substack.com/p/worried-ab...
Year-end tax guide before Dec 31st:
✅ Max 401k ($23.5K) & IRA ($7K)
✅ Harvest tax losses
✅ RMDs for 73+ (25% penalty!)
✅ FSA/HSA
✅ Strategic gifts ($18K)
✅ Quarterly taxes
Could save you $5K+ Which are you doing? 👇
advizmo.substack.com/p/year-end-t...
✅ Max 401k ($23.5K) & IRA ($7K)
✅ Harvest tax losses
✅ RMDs for 73+ (25% penalty!)
✅ FSA/HSA
✅ Strategic gifts ($18K)
✅ Quarterly taxes
Could save you $5K+ Which are you doing? 👇
advizmo.substack.com/p/year-end-t...
Year-End Tax Planning Guide To Save $3,000-$10,000 Before December 31st
A comprehensive guide to retirement contributions, tax-loss harvesting, RMDs, and other critical year-end financial moves.
advizmo.substack.com
October 28, 2025 at 5:45 AM
Year-end tax guide before Dec 31st:
✅ Max 401k ($23.5K) & IRA ($7K)
✅ Harvest tax losses
✅ RMDs for 73+ (25% penalty!)
✅ FSA/HSA
✅ Strategic gifts ($18K)
✅ Quarterly taxes
Could save you $5K+ Which are you doing? 👇
advizmo.substack.com/p/year-end-t...
✅ Max 401k ($23.5K) & IRA ($7K)
✅ Harvest tax losses
✅ RMDs for 73+ (25% penalty!)
✅ FSA/HSA
✅ Strategic gifts ($18K)
✅ Quarterly taxes
Could save you $5K+ Which are you doing? 👇
advizmo.substack.com/p/year-end-t...