Luke Matthews

Co-Founder | Lifestyle Blogger |  Content Marketer | Storyteller 

I teach you how to write with AI (and win LinkedIn)

You don't fit in. You feel left behind and you can't play the social media game that other's tell you to play.... 

Well stranger it's true that the internet has changed. BUT not all is lost....

Yes, dead internet theory is alive and well, it feels like there are no humans on LinkedIn™ or any platform anymore doesn't it? 

BUT my dear rebel, you aren't alone. 

After marketing for over 10 years on social media, building over 250k followers across all my platforms and ghostwriting for some of the biggest personal brands in the world....

I quit social media last year. 

Let me explain...

I built my social media on my terms. Sharing the most unhinged content you will ever see. I streamed drunk from the Scottish highlands, given away 1000s of dollars of pizza, hosted live meme competitions and battled other influencers LIVE... 

It was a blast BUT..... I started trying too hard to optimize my "personal brand" and I lost my way. 

10 bans on this platform didn't help and I decided to disappear into the shadows and leave the social media game behind. I was tired of being the rebel that got punished for playing a different game.

So I spent 2025 focusing on biohacking and figuring out how to enjoy my life again after years of hustling and obsession with work... 

It was a great year but truth be told I missed the banter. So I started questioning my choice to disappear...

It was during this journey that I learned a ton about private AI, cybersecurity as well as alternative tools that felt cool to use again. I tapped into my driving force....

Being a rebel without a cause. 

I like building things my way, on my time and saying whatever the heck I want. That's my roots. 

That's the way of the rebel, it's playing a different game with different goalposts and embracing it 1000% without any shame. 

AI and big tech want to put us into a cage. 
But we can use them to build our own kingdoms. 
We CAN build our own freedom.

So if that resonated with you, and you want to learn the "Rebel's Guide to the Creator Economy" and find a lane that serves you best...

I hope you'll follow me in 2026.

Cheers and lets crush it!

--

𝗪𝗮𝗻𝘁 𝘁𝗼 𝗷𝗼𝗶𝗻 𝗺𝘆 𝗻𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿 𝗮𝗻𝗱 𝗴𝗲𝘁 𝘁𝗼𝗼𝗹𝘀 𝗮𝗻𝗱 𝘁𝗮𝗰𝘁𝗶𝗰𝘀 𝘁𝗼 𝗯𝘂𝗶𝗹𝗱 𝗼𝗻𝗹𝗶𝗻𝗲 𝘁𝗵𝗲 𝗿𝗲𝗯𝗲𝗹 𝘄𝗮𝘆? 

Follow me and subscribe to my email list. You can subscribe by clicking any link in my profile as they all go to my newsletter on Substack. 

--

𝗔𝗿𝗲 𝘆𝗼𝘂 𝗹𝗼𝗼𝗸𝗶𝗻𝗴 𝘁𝗼 𝗽𝗮𝗿𝘁𝗻𝗲𝗿 𝗼𝗻 𝗮 𝘀𝗽𝗼𝗻𝘀𝗼𝗿𝗲𝗱 𝗽𝗼𝘀𝘁?

Email me at luke@wizardofoddmarketing.com

Founder - Lead Wizard & Ghostwriter

Linkedin & Twitter Ghostwriting Services for CEOs, Influencers, and Tech companies. 
Reach your audience with a sprinkle of magic, the power of explosive copywriting, and let the WIZARD OF odd MARKETING help make your biz a LOT  less boring.

Alright LinkedIn, let's be real for a second.

I know you're terrified... You see everyone else using AI and you either think:

A) "This is the end of human connection.... Soooo I'm going to write everything by hand in a candle-lit room!"

B) "I must prompt everything! I will become a GPT-powered content machine!"

Black and white thinking is just as lazy as the AI slop ur favorite influencer just posted. 

100% human get's u left behind.
100% AI get's u sounding like a robot.

The winning strategy is to be both human & AI. 

It's not that deep.

Use AI to handle the boring back end stuff.
Use your humanity to connect with your audience.

Easy peasy... 

Personally I've always enjoyed writing unhinged AND automating the back end like a nerd.

No need to pick a side.. 

Use AI AND be so human it stands out.

👊

𝗕𝗼𝗿𝗲𝗱 𝗼𝗳 𝗮𝗹𝗹 𝘁𝗵𝗲 𝗔𝗜 𝘄𝗿𝗶𝘁𝘁𝗲𝗻 𝘀𝗹𝗼𝗽 𝗵𝗲𝗿𝗲?

Join me on Substack for daily unhinged writing + bi-weekly newsletters for rebels.. https://lnkd.in/eagxG_7k

I got 99 problems and a LinkedIn ain’t one.

The 2026 LinkedIn algorithm favors written content.

But NOT AI slop... You must write SO human it hurts..... 

These writing staples used to work:

-Short sentences like this.
-Ridiculous post hooks.
-The rule of three.
-[this] vs [that] + [philosophical power statement'
-Open loops.
-Listicles...

But AI is good enough that you can feed it the above principles and it will do a decent job writing words and FEEL LIKE CHATGPT WROTE IT AND YOU WILL GET NO CLIENTS.........

Sorry folks but you got to write for yourself.

Writing in 2026 still requires you to learn techniques. 

But now it demands a secondary layer to feel human.... 

You need to add these to your skillset: 

-Chunky paragraphs. 
-Written technical knowledge of your industry.
-Humorous and cultural pieces. 
-The art of writing to specific pain points.
-Spelling mistakes n choppy sentences..
-The courage to say what others wont with some spice...

You don't need hot selfies.

But look ur words can't be mid any longer....

PS Yes I made this infographic with AI. Did it trigger u?

(I'm all for creating media with AI just no words lol)

How to create an elite infographic with AI.

Step 1: Turn the ON Switch on in your brain...

(yes you still need your wits to create with AI)

Step 2: Use the Artlist All-in-One AI Toolkit.
Step 3: Select Nano-Banana 2 (now on Artlist)
Step 4: Use my prompt.... 

Comment ELITE to get it and you can stop reading.

OR....

Read on and follow my actual 4-step framework for commanding the AI to work some magic because you know that AI s an illiterate artist that struggles with detail UNLESS you tell it exactly what to do and use the right model. 

That's why Nano Banana 2 is elite.

I used it to create this infographic within my work sandbox.

It's an elite text-to-image and image-to-image model where outputs are more accurate, detailed, and repeatable across generations. It keeps the speed the Nano Banana family is known for but improves the quality. Ideal for ad variations, social content, and video frames at scale. 

I mostly use it for infographics and ads. 

Anywhoodles....... here's the real 4 step guide: 

𝗦𝘁𝗲𝗽 𝟭: 𝗗𝗶𝗿𝗲𝗰𝘁 𝘁𝗵𝗲 𝗦𝘁𝘆𝗹𝗲.

Don’t say “make an infographic.” Say “make a professional infographic in a clean, magazine editorial style with a warm cream paper background and a sage green color palette.” Define the entire visual language from the start.

𝗦𝘁𝗲𝗽 𝟮: 𝗖𝗼𝗺𝗺𝗮𝗻𝗱 𝘁𝗵𝗲 𝗟𝗮𝘆𝗼𝘂𝘁.

Don’t let the AI guess the structure. Tell it exactly what you want. “Create a 4:5 aspect ratio image with a main title at the top, two cards in the middle, and a four-column feature section below.” You are the architect.

𝗦𝘁𝗲𝗽 𝟯: 𝗗𝗶𝗰𝘁𝗮𝘁𝗲 𝘁𝗵𝗲 𝗧𝗲𝘅𝘁.

Never let the AI write your copy. It’s an image generator, not a copywriter. Put every single word you want it to render in quotes. Titles. Body text. Labels. Everything.

𝗦𝘁𝗲𝗽 𝟰: 𝗟𝗼𝗰𝗸 𝘁𝗵𝗲 𝗗𝗲𝘁𝗮𝗶𝗹𝘀.

Be ruthlessly specific. Specify the fonts. List the exact color hex codes. Describe the icon style (“simple, hand-drawn doodle line art”). The more details you lock in, the fewer mistakes the AI can make.

Once again if you want my prompt comment ELITE but don't just copy me. 

Study it. See how it works.
Then, make it your own.

PS Who read the whole post? Your the best if you did.

--

𝗪𝗮𝗻𝘁 𝘁𝗼 𝗰𝗿𝗲𝗮𝘁𝗲 𝘄𝗶𝘁𝗵 𝘁𝗵𝗲 𝗔𝗿𝘁𝗹𝗶𝘀𝘁 𝗔𝗜 𝗧𝗼𝗼𝗹𝗸𝗶𝘁?

Sign up here: https://lnkd.in/ejKNGHgQ

The gurus took over LinkedIn. 

If you detest “how to get rich” posts.
If you detest “I made 50k MRR” posts..
If you detest “I have 500k followers” posts…

Do what I do...

Be ruthless. Mute, unfollow & block these grifting gurus.

And go where you are treated best...

I've been banned over 10x and have found battling the AI slop, endless grifting and platform indifference tiring..

So I post 1 or 2x a week and run ads.

I speak my mind on Substack and find my tribe of rebels there.

LinkedIn may be 69% dead... 

But the thinkers, builders & genuine souls are still building and fighting for their corner of the internet...

It's just not here.

🤷

3 years ago I booked a one way ticket to South America.

I’d never been, didn’t speak Spanish, didn’t know anyone……………..

Blah blah blah..... BLAH!

Every story like this now follows the same script. 

<Insert hero’s journey back story here>

<Insert relatable sob story struggles here>

<Insert comeback arc here>

<Insert generic encouragement here>

<Insert call to action to my program to teach u too>

Marketers and influencers somehow have ruined good storytelling too and the modern internet really is unbearable.....

But also... I... did... actually do this. 

I eat $500 steak for breakfast.

It changed EVERYTHING SO BUY MY COURSE OK......

<insert pattern interrupt here>

Ha ha ha ha....

I just can’t follow the script… 

Aight im done.

PS Who misses stories with no sell at the end?

--

So.. This is the perfect time to sell!!!

<insert not so surprising double plot twist here>

Yes. You've been had and I know you aren't mad about it.

So look.. Join my free community of rebels over on Substack. I rant about the creator economy and share daily icebreaker questions to help you meet humans....

Join us here: https://lnkd.in/dB96mKfP

I don't write with AI. But I do create media.

With Artlist I get access to the leading models like Kling 2.6 Pro, Sora 2 and new models like Seedance 2.0....

I use an isolated work sandbox when accessing Artlist to create infographics, PDFs and elite videos. 

(to keep my data as secure as possible) 

Cheers to Artlist for sponsoring this post.

They keep adding great AI models to the Artlist all in one AI Toolkit and Seedance 2.0 is coming soon....

You'll get features like:

𝗧𝗼𝘁𝗮𝗹 𝗔𝘀𝘀𝗲𝘁 𝗖𝗼𝗺𝗺𝗮𝗻𝗱: Tag anything to build via 1 prompt.

𝗙𝗹𝗮𝘄𝗹𝗲𝘀𝘀 𝗙𝗹𝗼𝘄: Generate seamless, one-take sequences with perfect cinematic continuity.

𝗧𝗵𝗲 𝗨𝗹𝘁𝗶𝗺𝗮𝘁𝗲 𝗠𝗮𝘀𝗵𝘂𝗽: Combine up to 12 assets like text, images, video, and audio all at once.

𝗦𝗼𝘂𝗻𝗱 𝗧𝗵𝗮𝘁 𝗛𝗶𝘁𝘀: Auto-generate sound effects and music that sync perfectly to the on-screen action.

𝗣𝗿𝗼-𝗟𝗲𝘃𝗲𝗹 𝗖𝗼𝗻𝘁𝗿𝗼𝗹: Swap characters, delete clips, or extend your footage from any frame.

Learn more about Seedance 2.0 here..
↳ https://lnkd.in/d5V-_QmV

Wild what can be done now with AI as a solo creator...

--

𝗪𝗮𝗻𝘁 𝘁𝗼 𝗰𝗿𝗲𝗮𝘁𝗲 𝘄𝗶𝘁𝗵 𝘁𝗵𝗲 𝗔𝗿𝘁𝗹𝗶𝘀𝘁 𝗔𝗜 𝗧𝗼𝗼𝗹𝗸𝗶𝘁?

Sign up here: https://lnkd.in/eFgDmM6u

PS Is it just me or does anyone feel the struggle to keep up with AI right now..... lol

This video was made using Seedance 2.0, coming soon to Artlist.

Brand partnership • I got 99 problems and a LinkedIn ain’t one.

I'm a Canadian who grew up playing hockey and I couldn't be more pleased that team USA won the gold........

Hockey players are the toughest of all sports. 

Hockey players fight, throw big hits and take pucks to the teeth, get up keep playing and score the game winning goal like Jack Hughes...

Aaaaand then go celly with the prez & handle the media with class....

But you know behind closed doors they are laughing.

#goats

PS What's your favorite sport? 

Oh and yes... I left Canada ages ago. No regrets... :)

Vibe coding is great for shipping apps.

But shipping a product people want to buy is the hard part....  

(you need an audience to sell too)

Vibe coding used to be a grifters dream. 

Sell the hope of making a product easy and making money fast BUT that's not the reality. It takes time to build a product and a business. 

The good news is.... AI can now help make technical part easy.

Replit lets me build the tool I wish existed when I was cleaning up my own digital life.

The tool I used to clean my digital footprint was great for a deep clean. But there was no simple, free way to just 𝘴𝘦𝘦 how much of my data I was exposing. I wanted a tool that made people aware of what the current risk was for their social media accounts and let them start cleaning up slowly.

So I built Privacy Guard using Replit which helps make building a mobile app and getting into the App Stores simple.

The traditional barriers of mobile development are handled by the AI.

This is how easy it is:

1. Start with a prompt of your tool/app idea.
2. Describe how the mobile app works.
3. Wait for AI to build a version 1.0.
4. Test and refine with reprompts.
5. Publish to the app store.

Yes, yes this is indeed a sponsored post by Replit.

But I actually did build my own mobile app.

Check out version 1.0 of "Privacy Guard" a social media privacy audit to help you see exactly what sensitive information you're exposing publicly. 

The tool only analyzes publicly visible content.
It processes your data and discards it. 
Nothing is stored on servers. 

Want a free privacy audit of your social media accounts? 

Comment "𝗔𝗨𝗗𝗜𝗧" and I'll send you the link. 

--

Build your own mobile app on Replit here:
>> https://lnkd.in/dATV8HUV

I delete my posts, comments and likes every 6 weeks.
I have not shared a real selfie in almost 9 months. 
I am a combo between AI fanboy & doomer....

AI has made marketing a lot easier. 

You can generate posts, PDFs, scrape lists, build websites, create graphics, videos and even automate follow up, DMs and a plethora of other activities...

I know people will scream it's not quality.

Unfortunately in the last 2 months all of these activities have become elite thanks to AI agents and the frontier models pushing further and further...

But the reason AI is accelerating?

You all give your data away in exchange for convenance. 

Now we have skynet loading, meta glasses invading your privacy and Claude training it's AI to have its own "ethics"....

The doom is real. 
The boom is real too.

I don't have all the answers, perhaps that is why I am pretty quiet despite showing up and posting again.

All I can say is... If you still have your data sitting in Google (to be used by Gemini), your data sitting in whatsapp, facebook and instagram (to be used by Facebook) and your data sitting in ChatGPT (to be used by OpenAI)....

You should be concerned. 

These companies do not care about you. 
These companies do not value privacy. 

If I were you I'd clean up my data and figure out how to access AI in a more secure, private way....

Personally I am learning how to run AI locally AND I spent 3 months last summer deleting all my data from big tech and deleting my social media accounts.

I only use LinkedIn for business and Substack to write.

Anywhoodles I'll let you get back to the next post promising you riches if you learn AI. 

😆

These are the 13 commandments of organic reach.

(A mostly helpful guide to get u 200k followers)

It took me 6 years to hit 200,000 followers.

But you can do it in triple the time. 

Let's get started eh?

Blessed are the impressions, cz dopamine...
Blessed are the mid selfies, for they get the likes
Blessed are the live streams, for they reach no one
Blessed are the em-dash haters for they are correct
Blessed are the AI comments for they boost our stats
Blessed are the coaches, for they will take your moneys
Blessed are the engagement pods, for they kill your soul
Blessed are the "We hit 500k MRR posts" for they are tru
Blessed are the "how to" educational posts, for they zzzzz
Blessed are the "comment this" posts for they make us $$
Blessed are the memes for they help me show up........

All but half of these will get as much reach as we should all like, but less than half of you will use these methods as much as they deserve.

So you see...

Organic reach is fleeting.
Followers don't matter.

But ancient texts (and modern translations) live on forever.

PS Yeah there's only 11 commandments (sue me)

I teach the art of raw writing & the science of private AI.

"Safe" is the most dangerous place to be as a writer.

If nobody hates your words, nobody loves them either.

Share a take.
Make some enemies.

Say the thing you’re afraid to say.

PS I love playing the whats the worst thing that can happen game? Well in this case you could get reported and banned just like I have over 10 times. But the thought of a final ban is actually relieving to me. But maybe if it isn't to u think about all this and be careful okay..

Some people luv Netflix after work.
Some people r pumped for beach holidays..
Some people can't wait to trial a cluster of ai agents on a local machine via a fresh Linux install running LM studio n way too much vram....

Yeah I don't get out much.

But when I do its a hardware run somewhere warm with a side of pickleball. 

PS Any local ai nerds out here? 

(I was the last "some people" hehe)

Controversial events are a gift.

Yes Karen, ur ChatGPT cartoon of bad bunny, cultural reform, matcha tea n Diary of a CEO motivational quote shared via poorly promoted AI written slop is a gift.

Now I don't have to see u in my feed.

The unfollow button is a gift peasants!

PS Repost this for Lady Gaga cz I think her last good song was in 2012.

Controversial events are a gift.

Yes Steven, ur ChatGPT cartoon of Kid Rock, bible verses, coors light beer n inspirational quote of Steve Jobs shared via a poorly prompted AI written slop is a gift.

Now I don't have to see u in my feed.

The unfollow button is a gift my diverse friends!

PS Repost this & spread the message of unity to all!

#badbunny #2posts1hour

Financial planning and education (without the jargon) I Creating blueprints for high-earning sales executives and business owners

I left the financial industry because I saw a problem.

People wanted to work with a planner, but they ended up becoming a number on a spreadsheet.

I had to leave to start something new.

And now?

I'm a fee-only planner who helps salespeople & equity compensated employees under 45 give a purpose to their paycheck.

I left the large financial institutions to start my own independent company. I did it so people could pay for real planning and not just an agenda to sell a hidden product. 

As a true fiduciary, Pashman Financial, LLC was built on that promise by focusing on you and you only.

🔵 Why people hire me? 

Well, people have come to me with the following problems:

- They want peace of mind with their money
- Their old advisor barely communicates with them
- They want an answer tailored to them, not from Google
- They felt pressured to buy a product that wasn't a right fit
- They are great at making money but struggle to keep it
- They want a simple plan that's easy to understand
- They want someone to hold them accountable
- They want someone they can trust

🔵 What are my services?

I help identify your goals, craft a financial blueprint that lays out action items to hit them, and monitor your progress. 

💵 Cash Flow Management  
📈 Equity Compensation
🏡 Real Estate Planning
📊 Investment Planning
📍 Retirement Planning
🛡 Insurance Planning
📚 Education Planning
💲 Tax Management
💳 Debt Repayment
📃 Estate Planning

🔵 Who do I serve?

Age: Individuals and families between 30-50 years old
Target: Sales pros, tech employees, other millennial families
Location: Virtually anywhere in the U.S.

But I love working with people that are driven to make a change. So even if you don’t fit these criteria, feel free to reach out. Your personality is everything. 

🔵 Why I'm different?

1) My model is primarily a flat fee service. No time trap. 

2) I do not require you to hand over your investments nor require a minimum to work with. Managing your assets is optional and I'll still assist you if you do it yourself. My focus is ongoing financial planning. 

3) I focus on how to increase your cash flow, not just your assets. I work with you to ensure your systems are set and consistently educate you on how your finances work. I get paid to truly keep you accountable over time.

You can find my pricing in my "featured" section on the website. 

Stop delaying action. Shoot me a message to schedule a complimentary intro.

Max Pashman, CFP®

50% of people have no idea what tax bracket they're in.

And most think more taxes mean less income. WRONG.

It's not a flat rate. 

The US tax system works at a progressive rate. 

In other words, each level of income is taxed at different rates. 

As new income is included, it is taxed at a higher rate. 

BUT that doesn't mean all of the income is taxed at that rate. 

The highest tax rate is called the "marginal rate". 

The overall tax rate (taxes divided by taxable income) is called the "effective rate". 

Big difference!

undefined undefined

pashman-financial-llc

schooloffinances

Helping Founders and Executives Plan for Early Retirement and Exit

The worst financial advice I've seen online: 
 
- Renting is a waste of money 
- Pay all debt first before investing 
- Spend everything now cause YOLO 
- Index Universal Life is better than a 401(k) 
- Don't increase your income so you can avoid more taxes 
- Buy [insert expense] solely because you can write it off 
- Index funds are bad because they are boring 
- Use your credit card as your e-fund 
- Never buy or lease a new car 
- Invest your e-fund 
- 401(k)s are a scam 
- All debt is bad 
 
These can either be challenged, too extreme, or just plain wrong. 
 
What might work for one person might not for another. 

What are some bad ones you've heard?

LinkedIn:

"Hot Take:

(insert most obvious common sense take)"

Going from $1,000 to $1,000,000 will create happiness. 

Going from $9,001,000 to $10,000,000 won't. 

Same dollar increase. 

Massive difference in results.

Once you elevate from levels of normal finanical stress such as:

- Going past paycheck to paycheck
- Paying off all your high interest debt
- Funding your children's education goals
- Purchasing your first home

Getting money for the sake of money becomes meaningless. 

You have to shift yourself into the next stage by asking a question:

-> How is wealth letting you focus on your happiness?

Not, how is wealth creating happiness.

It supports what actually drives happiness, such as:

- Financial independence so you can focus on your passion projects
- Security, so you can allocate your attention to your family
- Philanthropy so you can give back to your community

Then once you cross that point, what does more wealth do?

Each person has their own inflection point they cross. 

For some people, it’s $1 million.
For others it’s $5 million.
But for many, it’s when they stop worrying about bills.

And slowly, more wealth becomes just a number.

I bet you'd take $1 million focusing on what makes you happy versus $100 million still trying to figure that out. 

You might not need more money.

You might just need a clearer purpose for it.

You don’t need a financial planner if you’re HNW.

You just need to do the following:

- Investment planning
- Portfolio construction
- Asset allocation modeling
- Rebalancing across taxable, tax-deferred, and tax-free accounts
- Tax-aware asset location
- Capital gains management
- Tax-loss harvesting (and not violating wash sale rules)
- Multi-year tax projections
- Roth conversion timing and sizing
- AMT modeling
- Net investment income tax planning
- Equity compensation analysis (RSUs, ISOs, NSOs, ESPPs)
- 83(b) election decision modeling
- ISO AMT exposure tracking
- Concentration risk analysis
- Diversification strategy for concentrated stock
- Trading windows and blackout period planning
- Liquidity planning for large tax events
- Cash flow modeling across good and bad years
- Emergency fund optimization
- Opportunity cost analysis of excess cash
- Life insurance needs analysis
- Disability insurance review
- Umbrella liability coverage review
- ACA subsidy modeling
- Medicare planning
- Early retirement feasibility modeling
- Sequence-of-returns risk management
- Withdrawal strategy optimization
- Tax-efficient withdrawal order
- Guardrails vs fixed spending analysis
- Social Security claiming strategy
- Survivor benefit analysis
- Longevity risk modeling
- Estate planning coordination
- Beneficiary review across all accounts
- Annual exclusion tracking
- Lifetime exemption modeling
- Charitable giving strategy
- Entity structure planning considerations
- Reasonable compensation analysis
- Backdoor and Mega Backdoor Roth execution
- Exit planning scenarios
- Real estate analysis 
- Rent vs sell decision analysis
- 1031 exchange considerations
- Stress testing everything above
- Updating all of this every year
- And not panicking during market drawdowns
- And explaining it clearly to your spouse
- And actually implementing it correctly
- And staying compliant

Good luck!

"W2 employees never become millionaires."

Bulls***. I've consulted with 100s entering early retirement. 

Many were W2 employees, never actually owning a business. 

Or at least use it as a primary means of accomplishing millionaire status

They've crossed that point using the following methods:

- High savings rate towards stocks and real estate
- Equity compensation (More commonly via ISOs)

Owning a business is a massive opportunity to get there. 

And we've seen people retire early thanks to it too.

But it's not the ONLY method to create wealth.

Gotta pick that path that aligns with you.

But what do they all share in common?

Not sitting on the sidelines. 

They let investing take action. 

You earned hard for your paycheck. 

Now make it work harder for you.

Capital gains taxes can be your biggest ally or your worst enemy.

Here’s everything you need to know how they can affect your tax bill:

What is a Capital Gain?

It’s a tax applied when you sell an asset for a profit.

These assets can include:

-Stocks
-Crypto
-Real estate
-Businesses
-Personal property

There are two types of capital gains:

Short Term (STCG):

-> Assets held less than 1 year
-> Taxed as ordinary income

Long Term (LTCG):

-> Assets held more than 1 year
-> Taxed at preferential capital gains rates, separate from income taxes

Here’s a breakdown of the federal long-term capital gains rates for 2026:

Single:

-0%: $0–$49,450
-15%: $49,451–$545,500
-20%: $545,501+

Married Filing Jointly:

-0%: $0–$98,900
-15%: $98,901–$613,700
-20%: $613,701+

Relative to income brackets, you can see the immediate difference.

For Example (Single):

If you earned $200k and had $10k in STCG, it’s taxed as ordinary income.

Assuming a 32% marginal tax rate:

$10,000 × 32% = $3,200 in federal taxes

For $10k in LTCG, it’s taxed at the capital gains rate:

$10,000 × 15% = $1,500 in federal taxes

A huge difference!

But here’s where people mess this up:

Your capital gains rate depends on your total taxable income.

“Taxable income” is your adjusted gross income (AGI) minus below-the-line deductions (standard or itemized).

Which means those ranges include both your income AND your capital gains.

Example #1: Single, $50,000 Income, $10,000 LTCG

Total taxable income: $60,000
This puts all LTCG in the 15% bracket.
Tax:
$10,000 × 15% = $1,500 (Federal)

Example #2: Single, $30,000 Income, $10,000 LTCG

Total taxable income: $40,000
This falls entirely within the 0% bracket.
Tax:
$10,000 × 0% = $0 (Federal)

Example #3: Single, $30,000 Income, $20,000 LTCG

Total taxable income: $50,000
The income takes up the first $30,000.
Leaving $19,450 left in the 0% bracket.
$19,450 × 0% = $0

The remaining capital gains spill into the next bracket:
$550 × 15% = $82.50
-> Total LTCG tax: $82.50 (Federal)

This is why being strategic about when you realize capital gains matters.

By spreading gains over multiple years, you may take advantage of lower brackets.

Finally, remember:

Capital gains are not taxed inside tax-advantaged accounts
(e.g., 401(k)s, Roth IRAs).

That’s why most tax-loss harvesting opportunities live in taxable brokerage accounts.

Disclaimer: This is for financial education purposes only and not financial or tax advice.

A guy tweeted he put $50K in a Roth IRA.

Said it was one of the worst decisions he ever made.

And that’s great! A big reason:

Because if he contributed a total of $50k over the years, he could take out $50k of contributions penalty-free whenever he wanted.

“bUt yOu cAn’T tAkE oUt rEtIrEmEnT mOnEy dUdE”

Well…

This is actually a little secret hidden inside Roth IRAs.

Your earnings are distributed tax-free if certain conditions are met, most commonly being age 59½ and having held the account for at least 5 years.

But your contributions can be withdrawn at any time.

Roth withdrawals generally come out in this order:

1) Contributions 👉 can be taken out anytime
2) Conversions 👉 generally subject to a 5-year clock
3) Earnings 👉 usually require 59½ + 5 years

This means you don’t have to wait years to access your contributions.

However, once you take that money out, you permanently lose that Roth space, so this is best viewed as an emergency option, not a primary strategy.

But if you needed funds before 59½, you could access the contributions early.

Why is this a big deal?

It gives people pursuing financial independence a potential Plan B source of cash alongside other strategies.

So thank you, angry Twitter guy, for the lesson.

Note: Purely educational, not financial advice.

Shaq blew $1,000,000 in 30 minutes. 

But that mistake set him up for a $420,000,000 net worth. 

One of the best stories you'll hear. 

In Shaq's prime, he got his first endorsement deal.

The payment was worth around $1 million. 

Finally, he got paid! 

So he started with buying a car
$150,000 Mercedes

Then he bought his dad a car
$150,000 Mercedes (same model)

Then he bought jewelry.
Top tailored suits.
Nice stuff.

But of course, he didn't realize he still had payments to make

The taxes for the payout.
The fees for his agents.
And so on. 

Until he got a call from his accountant.

He told him he was $80,000 in the red! 

He describes this as the life-changing moment when his finances changed. 

Notice, it wasn't the moment he got all of his income. 
It was the moment he spent all of it. 

And soon he changed. 
And so did his habits.

Fast forward today, he has a $420 million net worth.

And he deployed his earnings in investments:

- Stocks
- Businesses
- Real estate

No matter where you are, everyone learns about money. 

And usually, the hard way is when it gets you. 

The art is not what you earn, but what you keep!

How are you keeping yours?

Them: We're looking to get a home.

Lender: How much were you looking to borrow?

Them: Well, how much can we?

Lender: 28% of your gross income. 

Them: Awesome. Let's do it. 

......

Them: We need help. How come it feels like we are stuck? We make really good income! 

Advisor: Let's take a look at your finances.

checks it*

Advisor: Well, I've found the problem. Your mortgage is 50% of your net income.

... 

Affording a down payment doesn't mean you can afford a property.

There's more to owning than just the price:

The costs you see. 

The costs you don't see. 

Don't lose sight of them.

Your child could get $1,000 free in a new account.

If your child was born 2025-2028, listen up:

Unofficially called the "Trump Account", here’s what we know so far:

- It’s a custodial Traditional IRA under section 408(a), with modifications
- Created for kids under age 18, with a valid SSN, when elected by a parent or grandparent
- Contribution limit = $5,000/year per child, adjusted for inflation after 2027
- Employers can also contribute up to $2,500 per child as part of a written plan
- Contributions are not tax-deductible
- Investments must track an index, have no leverage, and expense ratios under 0.1%
- Withdrawals not allowed until the child turns 18
- Contributions are treated as basis and not taxed again upon withdrawal
- Earnings are taxed as ordinary income
- 10% penalty applies to early withdrawals before age 59½ unless an exception under IRC Sec. 72 applies

But here is where the value is:

There’s also a pilot program starting in 2026:

Children born between 2025–2028 may be eligible for a $1,000 government-funded contribution if elected by their parents.

This account is new and the rules are still unfolding.

It shares similarities with other accounts like Traditional IRAs, 529s, and Roths, but has its own limitations and planning quirks.

The way to do this is by either:

1) Filing out Form 4547 here: https://trumpaccounts.gov./

2) Or filling out that same form with your tax preparer

These accounts are not expected to be funded before July 4th. 

If you file your 2025 return before that date without signing up on the website, you may have to wait until you file your 2026 return to receive the funds.

More to come as additional guidance is released!

Would you open one for your child?

If you're single on Valentines Day just remember your index funds still love you. 

Index and chill.

If your ESPP has a "look back", you're stting on a wealth hack. 

Here's the opportunity sitting in front of you. 

ESPPs are relatively simple. 

- You set aside your paycheck on a monthly basis for a period of time
- You buy your company stock at the end of the period
- Company let's you buy at a discount (usually 15%)
- The discount puts you at an immediate gain 

There some things to look out for like taxation, liquidity, and blackout periods to see how the ESPP works for you. 

But some have a provision called a "look back" period. 

The discount is applied either at the lower of the enrollment date or purchase date. 

For example:

If the enrollment price was $100 and $50 at the purchase price, the 15% is applied at the purchase price. 

If the enrollment price was $50 and $100 at the purchase price, the 15% is applied at the enrollment price. 

If the latter occurs you are looking at not only at 15% discount, but appreciation already of $50 between the $50 and $100! 

It's one of those great perks that can increase your wealth via your employer benefits. 

Don't discount the value of your company discount!

"I bought this stock cause Tik Tok guru 'StockMaster999' told me to"

Most people don’t actually know the tax status of their accounts.

Quick refresher 👇

Taxable Accounts:

- Individual Brokerage
- Joint Brokerage
- UTMA / UGMA

Pre-Tax Accounts:

- Traditional IRA
- SIMPLE IRA
- SEP IRA
- 403(b)
- 401(k)
- 457

Post-Tax Accounts:

- Roth IRA
- Roth 457
- Roth 401(k)
- Roth 403(b)
- Roth SEP IRA
- 529 (Could have a state deduction)

Triple-Tax:

- HSA (One of a kind)

Before worrying about returns?

Make sure you know how your money is taxed.

Which of these are you using?

There’s a more tax-efficient way to own an index.

But is it worth it? Here’s a breakdown of direct indexing:

What is direct indexing?

It’s still passive investing.

But instead of owning an index fund, you own the individual stocks that make up the index.

Same market exposure.
Different implementation.

The goal isn’t higher returns.
The goal is tax efficiency.
Index funds are already very tax-efficient, especially ETFs.

But there’s one thing they can’t do:
They can’t pass individual stock losses to investors.

Losses inside a fund stay inside the fund.
With direct indexing, you own each stock directly.

That allows for:

Ongoing tax-loss harvesting
Offsetting capital gains
Deferring taxes while staying invested

Over time, this can increase after-tax wealth even if pre-tax returns are similar.

Some studies suggest direct indexing can add incremental after-tax value over long periods (often cited at 1%–2%), but results vary widely based on volatility, tax bracket, cash flows, and implementation.

Important tradeoffs to understand.
This strategy is not a free lunch.

Here’s what actually matters.

1) Cost

Most platforms charge roughly 0.10%–0.20%.
But additional costs may include:

Trading costs
Cash drag
Tracking error
Etc.

These reduce the net benefit and must be weighed against expected tax savings.

2) New money works best

Selling existing index funds to switch strategies often creates taxes that wipe out the benefit.

Direct indexing tends to work best with new dollars, such as:

Income
Liquidity events
Sale or acquisition proceeds
Using fresh capital avoids unnecessary tax friction.

3) Tax benefits depend on markets

The biggest advantage comes from harvesting losses, which requires volatility.

In prolonged bull markets:
Losses become harder to find
Unrealized gains accumulate

Tax benefits shift from harvesting losses to deferring gains, and eventually decline.

4) Wash sale coordination matters

Loss harvesting must be coordinated across taxable accounts, spousal accounts, and any index funds held elsewhere.

Poor coordination can reduce or eliminate the benefit.

5) You need an exit strategy

Deferred taxes eventually come due unless there’s a plan.

Is this money for retirement, charity, heirs (step-up in basis), or future liquidity?

Direct indexing works best when paired with broader tax and estate planning.

6) Benefits skew toward higher earners

The tax alpha is largest when tax rates and taxable balances are high.

For lower brackets or smaller portfolios, added cost and complexity may outweigh the benefit.

Bottom line

Direct indexing isn’t a magic upgrade.
It’s a tax optimization tool.

For the right investor, at the right time, with the right plan, it can add meaningful after-tax value.

For others, a low-cost index fund may be the better answer.

That’s why this should be a planning decision, not a product pitch.

If you’re exploring it, talk with a fee-only planner to see if it actually fits your situation.

Commissions coming with a 6 figure tax surprise?

Well, we commonly hear this misconception:

"My commissions are taxed at a higher rate!"

Not always. Why is it wrong?

Let's look at an example here.

Selling Sally works hard at her job.

She typically gets half in salary and half in commissions.

She’s hit her quota and is excited for those commissions to kick in.

But when she checks her paycheck, she notices something…

Her commissions were "taxed" at a lower rate than her salary.

At first, this seems great, more money in her bank account!

But then, tax season arrives.

After filing her taxes, her accountant lets her know she owes a massive tax bill!

Now she's frustrated that she has to write a big check and wonders:

Did something go wrong with her return?
Did she get taxed more than expected?
Did she get hit with some penalty?
Nope.

She owes more because her employer withheld less than she actually owed.

And that's the key word here: withheld.

Whenever you have monthly income like a salary, it’s considered “regular,” which gets taxed progressively like usual.

But whenever you have irregular income like:

Awards
Bonuses
Commissions
Equity Compensation
Or anything that doesn’t pay monthly
…it’s considered “supplemental.”

And these irregular forms of income are withheld at different flat rates by default.

For commissions, the default withholding is 22% for the first $1 million and 37% for any amount beyond that (Federal rate for 2025).

This is just withholding, not the actual tax owed.

Since Sally makes $500,000, her actual marginal tax rate is 35%.

But her commissions were only withheld at 22%, which wasn’t enough.

So instead of getting a refund, she ended up owing the difference at tax time.

She didn’t pay more for her commissions.

She just had less withheld than owed.

Big difference!

(Sally is a hypothetical example, but you get the point)

57% of workers are contributing to their 401(k). 

But most don't know if theirs is good. Here's what you should know:

The truth is that not all 401(k)s are treated equally. 

Some are good. 

While others are disappointing. 

But the account is not at fault: it's how it's structured. 

Employers create them how they see fit. 

So, what are the top areas to look at?

In my view:

- Whether they limit your contribution limits
- Do they offer a Roth option to you
- Do they offer a match to you
- Do they offer more than a target date
- Do they offer low-cost index options 
- Do they offer an after-tax option that you can convert

The more these boxes are checked off, the better. 

It's not about the account you have. 

It's how you use the account too! 

Do you have a 401(k)?

- - - - - - - - - - - - - - - - - - - - - - - - - - -

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You would need a 1,000% return on a $1,000 portfolio to have the same dollar-for-dollar return as a $100,000 portfolio with a 10% return.  
 
Read that again 👆 
 
It's much easier to accomplish the latter than the former.  
 
But it doesn't have to come simply from high returns.  
 
So if you don't have a 6 figure portfolio yet? 
 
Focus on your savings rate, not returns.

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