Ally Jane Ayers, CFP®

Ally Jane Ayers is Co-Founder of the financial planning firm @Brooklyn_FI. Newsletter: Money Changes Everything. Book: “Creative Money,” out November 2026.

[Ally Jane Ayers, CFP® @aallyjane]

A very boring essay about renters insurance you probably shouldn't read. https://t.co/5yRD9pLWl6

[hrdk @hrdktwt]

Someone on Reddit built a game where you ride a dirt bike on top of any company's stock chart.

[Ally Jane Ayers, CFP® @aallyjane]

How empty is too empty when it comes to savings before a move?

Questions like these are more about safety than anything else.

[Ally Jane Ayers, CFP® @aallyjane]

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.
https://t.co/z5tqSQ2oc7

[Ally Jane Ayers, CFP® @aallyjane]

• 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.

https://t.co/z5tqSQ2oc7

[Ally Jane Ayers, CFP® @aallyjane]

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.

[Ally Jane Ayers, CFP® @aallyjane]

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

[Ally Jane Ayers, CFP® @aallyjane]

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

[Ally Jane Ayers, CFP® @aallyjane]

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. That’s why wills and trusts matter.

https://t.co/nKAr1kKTCF

[Ally Jane Ayers, CFP® @aallyjane]

The difference between understanding this rule and missing it is often six figures.

If your family owns appreciated assets, this one matters.

https://t.co/nKAr1kKTCF

[Ally Jane Ayers, CFP® @aallyjane]

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.

[Ally Jane Ayers, CFP® @aallyjane]

We cover:
• What “basis” actually means
• How the step-up wipes out lifetime capital gains
• Why gifting assets before death can accidentally create a huge tax bill
• Which assets qualify — and which don’t
• The appraisal step many families skip (and regret)

[Ally Jane Ayers, CFP® @aallyjane]

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

https://t.co/tux2O9J9CV

[Ally Jane Ayers, CFP® @aallyjane]

There are really only two ways small business income gets taxed:

Option 1: Sole Proprietor
Option 2: Entity (S-corp or Partnership)

[Ally Jane Ayers, CFP® @aallyjane]

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 have no idea how much money is available to them.

https://t.co/tux2O9J9CV

[Ally Jane Ayers, CFP® @aallyjane]

• LLC vs how you’re taxed
• 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.

https://t.co/tux2O9J9CV

[Ally Jane Ayers, CFP® @aallyjane]

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.

We cover:

[Ally Jane Ayers, CFP® @aallyjane]

So if your revenue is $100,000, 3% is $3,000 — which should cover tax return prep, but not bookkeeping.

https://t.co/k6atMiRhoP

[Ally Jane Ayers, CFP® @aallyjane]

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.

[Ally Jane Ayers, CFP® @aallyjane]

You probably need a bookkeeper who is supervised by a tax accountant. The general rule of thumb is to allocate 2–3% of your revenue to finance, accounting, bookkeeping, tax prep, and strategic help.