iiinova — where your digital self keeps evolving

AJ Ayers @ajayers.bsky.social · 09/08/2026

Extremely tickled to say that my first book, Creative Money: New Financial Rules for Artists, Innovators, and Misfits, comes out this fall from Penguin Randomhouse. Get your copy wherever books are sold. www.penguinrandomhouse.com/books/808718...

penguinrandomhouse.com

Creative Money by AJ Ayers: 9798217180462 | PenguinRandomHouse.com: Books

An essential guide to managing your money for artists, freelancers, tech workers, influencers, and innovators, from an irreverent financial advisor There’s a good reason why so many people feel...

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AJ Ayers @ajayers.bsky.social · 20/03/2026

How empty is too empty when it comes to savings before a move? Questions like these are more about safety than anything else.

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AJ Ayers @ajayers.bsky.social · 18/03/2026

When people say they’re afraid of being house poor, they’re usually talking about more than just the monthly payment. They’re talking about the feeling that the house consumes all available resources: cash, flexibility, attention, and emotional bandwidth.

moneychangeseverything.substack.com

Can I Afford to Move #2: Is Draining Our Savings to Buy a Home a Bad Idea?

Key Takeaways

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AJ Ayers @ajayers.bsky.social · 17/03/2026

• What “house poor” actually means (and why people feel it immediately) • When putting less down and keeping cash can actually be the better move Buying a home can feel like progress, until your bank account hits zero.

moneychangeseverything.substack.com

Can I Afford to Move #2: Is Draining Our Savings to Buy a Home a Bad Idea?

Key Takeaways

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AJ Ayers @ajayers.bsky.social · 17/03/2026

This week on my Substack, Money Changes Everything, I break down one of the most common (and misunderstood) homebuying questions: should you empty your savings for a down payment? We cover: • Why draining your savings increases risk • The difference between liquidity and wealth

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AJ Ayers @ajayers.bsky.social · 17/03/2026

Most people aren’t deciding between “buy” and “don’t buy” a home. They’re deciding how much risk they’re willing to take on without realizing it.

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AJ Ayers @ajayers.bsky.social · 13/03/2026

Understanding how, when, and where step-up and basis works matters because sometimes people try to be smart, and sometimes outsmart themselves.

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AJ Ayers @ajayers.bsky.social · 11/03/2026

Step-up in basis is a tax rule, not an estate plan. It doesn’t decide who gets the house, who controls the brokerage account, or whether your kid, your spouse, or your estranged cousin ends up owning the thing in the first place. That’s why wills and trusts matter.

moneychangeseverything.substack.com

Please Kill Me: The Step Up in Basis at Death

Key takeaways:

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AJ Ayers @ajayers.bsky.social · 10/03/2026

• Why gifting assets before death can accidentally create a huge tax bill • Which assets qualify • The appraisal step many families skip (and regret) The difference between understanding this rule and missing it is often six figures. If your family owns appreciated assets, this one matters.

moneychangeseverything.substack.com

Please Kill Me: The Step Up in Basis at Death

Key takeaways:

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AJ Ayers @ajayers.bsky.social · 10/03/2026

It’s the reason heirs can inherit appreciated assets — real estate, stocks, even business interests — and sometimes owe zero capital gains tax on decades of growth. We cover: • What “basis” actually means • How the step-up wipes out lifetime capital gains

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AJ Ayers @ajayers.bsky.social · 10/03/2026

When you die, so do your capital gains. This week on my Substack, Money Changes Everything, I’m breaking down one of the most misunderstood (and surprisingly generous) rules in the tax code: step-up in basis.

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AJ Ayers @ajayers.bsky.social · 06/03/2026

The key takeaway: both setups can be LLCs. The LLC gives you liability protection. The tax structure determines the complexity. If you’re just starting out or staying solo, you’re likely in the first camp. If your business grows, you can opt into the second.

moneychangeseverything.substack.com

How to Set Up a Business the Right Way

Don't worry, you can change your mind later!

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AJ Ayers @ajayers.bsky.social · 06/03/2026

There are really only two ways small business income gets taxed: Option 1: Sole Proprietor Option 2: Entity (S-corp or Partnership)

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AJ Ayers @ajayers.bsky.social · 04/03/2026

I’ve seen people bring in six figures through their business and still feel broke because they never set up the basic systems and processes for running their own business and therefore have no idea how much money is actually available to them to spend or expect to pay in taxes.

moneychangeseverything.substack.com

How to Set Up a Business the Right Way

Don't worry, you can change your mind later!

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AJ Ayers @ajayers.bsky.social · 03/03/2026

We cover: • LLC vs how you’re taxed (not the same thing) • Sole prop vs S-Corp — when each makes sense • Why bookkeeping isn’t optional • The 30% / 50% tax rule • A clean first-year roadmap If you’re in Year 1, make these moves before admin starts running you.

moneychangeseverything.substack.com

How to Set Up a Business the Right Way

Don't worry, you can change your mind later!

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AJ Ayers @ajayers.bsky.social · 03/03/2026

Most people don’t start a business. They just start getting paid. One client turns into three. Income grows. Structure doesn’t. This week on my Substack, Money Changes Everything, I break down how to set up a business before the chaos sets in.

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AJ Ayers @ajayers.bsky.social · 02/03/2026

The general rule of thumb is to allocate 2–3% of your revenue to finance, accounting, bookkeeping, tax prep, and strategic help. So if your revenue is $100,000, 3% is $3,000 — which should cover tax return prep, but not bookkeeping.

moneychangeseverything.substack.com

Should I Fire My Accountant?

Answer: probably not.

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AJ Ayers @ajayers.bsky.social · 02/03/2026

How much should accounting actually cost? Accounting is an expense and it should be proportional to your needs. If you’re a business owner with straightforward income and standard expenses, your monthly accounting shouldn’t break the bank. A few hundred dollars a month is typical.

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AJ Ayers @ajayers.bsky.social · 27/02/2026

The accountant–taxpayer relationship is broken. It’s too rushed, too narrow, and often disconnected from the rest of your financial life. Especially if you’re a business owner or someone with RSUs (Restricted Stock Units), stock options, maybe even a future exit.

moneychangeseverything.substack.com

Should I Fire My Accountant?

Answer: probably not.

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AJ Ayers @ajayers.bsky.social · 25/02/2026

No, you should absolutely not fire your accountant under any circumstances. Okay, maybe there are a few circumstances where it makes sense, like fraud.

moneychangeseverything.substack.com

Should I Fire My Accountant?

Answer: probably not.

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AJ Ayers @ajayers.bsky.social · 24/02/2026

The tax code isn’t getting simpler. The profession is shrinking. And most people are trying to treat a year-round system like a customer service line. Before you send the breakup email, make sure you understand the relationship you’re in.

moneychangeseverything.substack.com

Should I Fire My Accountant?

Answer: probably not.

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AJ Ayers @ajayers.bsky.social · 24/02/2026

• The difference between tax filing and real tax planning • What you’re actually paying for when you hire a CPA • Why good accountants are harder to find right now • What “normal” pricing looks like for people with real income • How to find someone good before you’re desperate in March

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AJ Ayers @ajayers.bsky.social · 24/02/2026

This week on my Substack, Money Changes Everything, I break down when you should actually fire your CPA — and when you’re about to make a reactive (and expensive) decision. Here’s what we cover:

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AJ Ayers @ajayers.bsky.social · 24/02/2026

Every spring, someone decides their accountant is the problem. They didn’t respond fast enough. They said no to a deduction. The tax bill was higher than expected. Sometimes that’s incompetence. More often, it’s misaligned expectations.

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AJ Ayers @ajayers.bsky.social · 20/02/2026

If you have freelance or business income in the rough range of $20,000 to $150,000 net, the SEP IRA is usually the right answer. Above that, other options like a solo 401(k) can make sense. Below that, it still works, but cash flow might be the bigger constraint.

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AJ Ayers @ajayers.bsky.social · 18/02/2026

Call it something like SEP IRA BANANA STAND throughout the year. That way, you can just move the money in that account over to your actual SEP IRA account at the end of the year.

moneychangeseverything.substack.com

Ode to the SEP IRA

Of all the retirement accounts, it’s the easiest to work with

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AJ Ayers @ajayers.bsky.social · 18/02/2026

The SEP IRA is a response to income you’ve already earned, not a guess at future income you might earn. And if you really want to do it right, starting NOW, you should save 20% of every single dollar you make in a high-yield savings account.

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AJ Ayers @ajayers.bsky.social · 17/02/2026

If you’re self-employed and your income shows up on a 1099, this framework will likely simplify more than you expect — and reduce your tax bill in the process.

moneychangeseverything.substack.com

Ode to the SEP IRA

Of all the retirement accounts, it’s the easiest to work with

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AJ Ayers @ajayers.bsky.social · 17/02/2026

• Why the real contribution rate is closer to 20% than 25% • When a solo 401(k) actually earns its added complexity • Who should absolutely avoid using a SEP IRA

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AJ Ayers @ajayers.bsky.social · 17/02/2026

This week on my Substack, Money Changes Everything, I break down why the SEP IRA is often the cleanest move for self-employed income. Here’s what we cover: • Why the SEP IRA works so well for lumpy, unpredictable income • The feature that makes it elite • How it lowers your tax bill

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AJ Ayers @ajayers.bsky.social · 17/02/2026

For freelancers and business owners, retirement advice gets complicated fast — solo 401(k)s, backdoor strategies, optimization stacked on optimization. Meanwhile, the SEP IRA is sitting there quietly doing exactly what most people need it to do.

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AJ Ayers @ajayers.bsky.social · 14/02/2026

If you're waiting to buy the dip, you don't have an investment strategy.

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AJ Ayers @ajayers.bsky.social · 11/02/2026

The phrase “wait for the market to go on sale” gets thrown around like somebody knows something you don’t. It’s really just vague market timing with a consumer mindset. There’s no sale price for the S&P 500. The market doesn’t send out a discount code in an email when it’s ready for you to re-enter.

moneychangeseverything.substack.com

Buying the Dip is for Losers

You’re not a contrarian genius, you just got lucky.

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AJ Ayers @ajayers.bsky.social · 10/02/2026

• How sitting in cash can undermine long-term wealth • What to do instead if your goal is sustainable, repeatable growth If your investing plan depends on catching the bottom, you don’t have a plan — you have anxiety with a spreadsheet.

moneychangeseverything.substack.com

Buying the Dip is for Losers

You’re not a contrarian genius, you just got lucky.

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AJ Ayers @ajayers.bsky.social · 10/02/2026

• Why buying the dip requires being right twice • What “waiting for the market to go on sale” is really betting on • Why the best investing days tend to come right after the worst ones

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AJ Ayers @ajayers.bsky.social · 10/02/2026

This week on my Substack, Money Changes Everything, I break down why buying the dip can quietly cost people real returhttps://moneychangeseverything.substack.com/p/buying-the-dip-is-for-losers ns over time. Here’s what we cover:

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AJ Ayers @ajayers.bsky.social · 10/02/2026

What people usually mean when they say they’re “waiting to buy the dip” is that they’re holding cash, watching the market, and hoping they’ll feel confident at the exact moment things look the worst.

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AJ Ayers @ajayers.bsky.social · 10/02/2026

Buying the dip can work, but that’s the problem. When it works, it looks like skill. Most of the time, it’s just luck.

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AJ Ayers @ajayers.bsky.social · 06/02/2026

The IRS doesn’t care if you need more time. They want their money on time.

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AJ Ayers @ajayers.bsky.social · 05/02/2026

I'm writing a book! It's called "Creative Money: New Financial Rules for Artists, Innovators, and Misfits," and it's coming out this November. This week's update comes to you from a conference in Puerto Rico. I'm in the final stretch of finishing the manuscript, still trying to cut some words.

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AJ Ayers @ajayers.bsky.social · 04/02/2026

Filing an extension is not a failure. It’s a flex. The IRS doesn’t care if you need more time. They want their money on time. File Form 4868 by April 15, pay what you think you owe, and finalize later.

moneychangeseverything.substack.com

Stop Thinking About Taxes As an April Problem

You’re not behind. You’re just thinking about taxes like a civilian.

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AJ Ayers @ajayers.bsky.social · 03/02/2026

Good tax planning is boring. When it’s working, April 15th is just a warm spring day. If tax season reliably feels heavier than it should, this post is designed to make the entire process clearer and more manageable.

moneychangeseverything.substack.com

Stop Thinking About Taxes As an April Problem

You’re not behind. You’re just thinking about taxes like a civilian.

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AJ Ayers @ajayers.bsky.social · 03/02/2026

Here’s what we cover: • How tax projections in July and October change the entire experience • When filing an extension is a smart, strategic move • How to save for taxes so the money is there when you need it • Why paying for real advice is often cheaper than fixing avoidable mistakes

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AJ Ayers @ajayers.bsky.social · 03/02/2026

Most people think about taxes once a year. Usually in March, almost always with a sense of mild dread. This week on my Substack, Money Changes Everything, I break down what it actually looks like to plan for taxes the way professionals do.

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AJ Ayers @ajayers.bsky.social · 30/01/2026

If you really love animals, love them enough to wait until your life is stable enough to afford it.

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AJ Ayers @ajayers.bsky.social · 28/01/2026

If you’re thinking of getting a pet, don’t start at the shelter or browse the breeder’s website that has a new litter of puppies named after famous scientists because a little Aussie named Einstein may send you to the state-funded old folks home if you’re not up for some financial planning first.

moneychangeseverything.substack.com

Your Pet Is Making You Poor

How to Prepare Financially for a New Family Member

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AJ Ayers @ajayers.bsky.social · 27/01/2026

• What a healthy pet actually costs year over year • How to tell if the timing is right—or if waiting is the more responsible choice If you love animals, you should want to care for them without undermining your own financial stability. This post makes the tradeoffs clear before they get expensive.

moneychangeseverything.substack.com

Your Pet Is Making You Poor

How to Prepare Financially for a New Family Member

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AJ Ayers @ajayers.bsky.social · 27/01/2026

• Why pets are financial dependents, not lifestyle upgrades • Why vet emergencies are inevitable, not unlucky • What pet insurance protects you from (and what it doesn’t)

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AJ Ayers @ajayers.bsky.social · 27/01/2026

I’m all for a four-legged companion, so long as it doesn’t eat away at your savings. This week on my Substack, Money Changes Everything, I break down the real cost of pet ownership, including:

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AJ Ayers @ajayers.bsky.social · 27/01/2026

I’ve watched people adopt pets purely out of emotion, without fully understanding the long-term cost. The financial impact of a pet is rarely factored into the initial decision to own one, and the consequences usually show up later in the form of emergency vet bills and lifestyle changes.

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