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

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

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

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

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

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

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

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

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

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

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

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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AJ Ayers @ajayers.bsky.social · 24/01/2026

Who’s the best candidate for Roth IRA contributions? Your kids. Here’s how you can start investing in a Roth for them as early as possible.

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AJ Ayers @ajayers.bsky.social · 21/01/2026

America is full of broken systems, but the Roth IRA is one of the few that actually works.

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AJ Ayers @ajayers.bsky.social · 20/01/2026

I knew Roth IRAs were important long before I understood how they actually worked. I didn’t really grasp them until my late 20s.

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AJ Ayers @ajayers.bsky.social · 16/01/2026

A real money goal has to answer these 3 questions: What exactly are you trying to change, by how much, and by when?

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AJ Ayers @ajayers.bsky.social · 15/01/2026

I'm publishing a book! It's called "Creative Money: New Financial Rules for Artists, Innovators, and Misfits" and it's coming out in November of this year. I haven't done a book update in a while, so I wanted to drop in here today and share the latest. We're fast approaching the finish line!

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AJ Ayers @ajayers.bsky.social · 14/01/2026

Without a documented plan, consequences, rewards, and measurable outcomes, goals are just added stress. Without a system, your goals are just clean, wrinkled t-shirts on the floor. You don’t accomplish them. You just move them around.

moneychangeseverything.substack.com

Why Most Money Goals Fail and How to Fix That

Key Takeaways

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AJ Ayers @ajayers.bsky.social · 13/01/2026

Most money advice focuses on motivation. This week on my Substack, Money Changes Everything, I’m looking at money goals as a system instead. Most people don’t fail because they’re bad with money. They stall because their goals are vague, endless, and impossible to finish.

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AJ Ayers @ajayers.bsky.social · 07/01/2026

Right-sized homes retain their value beautifully because they’re accessible to more buyers, more ages, more stages of life. While my California home is a strain on my budget today, my hope is that if I hold onto it for decades, my costs to live there when I’m old and frail will be minimal.

moneychangeseverything.substack.com

At 32, I Bought the House I Plan to Die In

Forgive the clickbait headline.

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AJ Ayers @ajayers.bsky.social · 06/01/2026

Most housing advice focuses on upgrading. This week on my Substack, Money Changes Everything, I’m looking at housing as a long-term financial system instead. At 32, I bought the house I expect to live in for the rest of my life.

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AJ Ayers @ajayers.bsky.social · 05/01/2026

One of the things I'm most proud of from 2025 is the sheer amount of words I wrote. 52 Substack essays with an average length of 2,000 words, plus a big old non-fiction book. By my estimates, I wrote more than 250,000 words this year (!).

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AJ Ayers @ajayers.bsky.social · 02/01/2026

Last year (yes, 2025), I wrote about the things I wish I’d done earlier in my career, and one of them is a “brag sheet.” “I wish I’d started keeping a record of my achievements: promotions, raises, freelance pitches...

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AJ Ayers @ajayers.bsky.social · 31/12/2025

Goals For 2026: • Spend more time in libraries and bookstores • Less playing golf, more practicing golf • Reach 10,000 Substack followers • See Creative Money on the NYT Bestseller list Wishing you a happy, healthy, and wealthy 2026. Join me in January for some down-to-earth goal-setting!

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AJ Ayers @ajayers.bsky.social · 30/12/2025

This week on my Substack, Money Changes Everything, I’m reflecting on 2025. It's less a highlight reel, more a case study in what holds when life gets messy.

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AJ Ayers @ajayers.bsky.social · 26/12/2025

What I recommend to clients who want to invest ethically—particularly those concerned about exposure to industries like weapons manufacturing—is to separate investing from impact.

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AJ Ayers @ajayers.bsky.social · 25/12/2025

So-called socially responsible portfolios are built on arbitrary scoring systems, not moral clarity. Take a widely marketed ESG fund like the Vanguard ESG U.S. Stock ETF (ESGV). On the surface, it sounds exactly like what a values-driven investor would want:

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AJ Ayers @ajayers.bsky.social · 24/12/2025

This week on my Substack, Money Changes Everything, I’m writing about ethical investing — and why it so often feels meaningful without actually being effective.

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AJ Ayers @ajayers.bsky.social · 19/12/2025

There are only two ways to make money. You can work for it, or you can let your money do the work. When you work, you pay some of the highest tax rates in the system. When your money works, you pay less. That’s the not-so-secret reason everyone is obsessed with capital gains.

moneychangeseverything.substack.com

Hail Mary Tax Planning Moves to Make Before the End of the Year

Capital Gains, Charity, and Roth Conversions

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AJ Ayers @ajayers.bsky.social · 17/12/2025

Make tax moves while you still can. In the world of tax planning, laziness is very expensive.

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AJ Ayers @ajayers.bsky.social · 11/12/2025

Just because someone on the internet says it's true (including me), it doesn't mean that it applies to you. Starting a little series called, "Can I Afford to Move?" where I take real people's questions and break them down based on their situation.

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AJ Ayers @ajayers.bsky.social · 10/12/2025

Here’s some “common wisdom” that could use a little more scrutiny: Renting is throwing money away.

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AJ Ayers @ajayers.bsky.social · 09/12/2025

This week on my Substack, Money Changes Everything, I tackled one of the most common questions I hear from couples planning their next move: Should we pay off our mortgage before we buy our next home?

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AJ Ayers @ajayers.bsky.social · 05/12/2025

If I were to design a practical money class for life after college, it would be a six-part series for emerging adults. These would be the classes: Class 1: What You Earn and What You Keep Class 2: Budgeting and the Real Cost of Moving Out

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AJ Ayers @ajayers.bsky.social · 04/12/2025

An S-Corp can save you money on self-employment taxes. Instead of paying 15.3% on all your profits (that’s just the payroll tax that every business pays), you pay it only on a “reasonable salary” you set for yourself.

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