Insights

Indexed by the situation you are in.

Articles and podcast episodes in one place, sorted by what is actually happening to you rather than by date.

A man in an apron wipes down the counter of an empty cafe, looking out of the window.

1 Oct 2026

Unused knowledge is worthless

Money needs time the way concrete needs time to cure. Waiting for the right lump sum is the most expensive habit there is.

A woman sits behind a desk holding her glasses, listening to someone standing in front of her.

Article

29 Sep 2026

You cannot be too nice in business

It is rarely a bad quarter that drains a business. It is the owner who was too nice to hold a line.

A man leans against a workbench with his arms crossed, talking to someone out of frame.

Article

24 Sep 2026

Nobody is buying your features

Two one-star reviews, a thousand happy clients, and nobody could see it.

A young man stands in an open garage workshop, looking at a half-finished build on the bench.

Article

22 Sep 2026

Build the plane while you are flying it

The people who struggle with money are rarely the people who lack information.

A woman unlocks the front door of her salon, an Abierto sign hanging in the glass.

Article

12 Sep 2026

The deduction most owners miss in their first profitable year

It is not obscure and it is not aggressive. It is just timing, and most people find out in April.

Episode art

Podcast

Episode 39 · 31 min

Your first year over $500K

What changes the moment the number crosses, and what should have changed before it did.

A man in a work jacket stands in a brick doorway, one hand on the frame, looking down an empty street.

Article

4 Sep 2026

What a cost segregation study actually does to your return

Plain numbers on a real property, and the point where it stops being worth doing.

A woman in a grey cardigan stands in a hallway holding an opened letter and a small pile of mail.

Article

28 Aug 2026

Reading an IRS notice without panicking

Most of them are not what people think. How to tell which kind you have.

Episode art

Podcast

Episode 41 · 34 min

Selling a business without handing half to the IRS

The moves that shrink the bill, and the deadline each one is tied to.

A man stands at a kitchen island with a coffee press, a laptop and an unopened envelope.

Article

21 Aug 2026

Equity vesting in a year you cannot control

Nothing was sold and nothing was received, and the income is there anyway. The bill arrives before the cash does.

An older woman locks the glass door of her shop at dusk in a narrow lane.

Article

19 Aug 2026

Asset sale or stock sale, and why the buyer cares

The structure is negotiated long before closing, and it is worth real money to get right.

Episode art

Podcast

Episode 40 · 28 min

When an S-corp election actually pays for itself

The income level where it starts to make sense, and the payroll obligation that comes with it.

A man sits on a staircase holding an opened letter, looking away from it.

Article

14 Aug 2026

What actually triggers a second look

Not the deduction you are afraid of. Mismatches, and figures that sit out of proportion to everything around them.

A woman in a blazer sits alone at a long boardroom table with a notepad and pen.

Article

12 Aug 2026

The planning window on a business sale closes earlier than you think

By the time there is a letter of intent, most of the moves that change the outcome have already closed.

A young woman in an apron sets down a stack of trays while an older man in an apron talks to her across a cafe counter.

Article

11 Aug 2026

Hiring your children, the version that holds up

Contracts, labour logs, payroll, and the year-end filings. Half-doing this is the expensive outcome.

A woman stands at an open filing drawer, lifting out a worn folder.

Article

7 Aug 2026

The documentation that turns a strategy into a position

Receipts are not documentation. A position you can defend looks different from one you are hoping nobody asks about.

A man in a blue shirt stands alone in an empty workshop, looking towards the window.

Article

5 Aug 2026

Installment sales, and trading certainty for tax

Taking the money over time can keep the gain out of one crowded year. It also leaves you holding the buyer's risk.

A man in a light blue shirt stands at a standing desk, frowning at a printed page.

Article

4 Aug 2026

What a reasonable salary actually means, and who decides

There is no percentage rule. There is a facts and circumstances test, and a position you can either defend or not.

A man in a beanie sits at a cluttered desk in a warehouse, reading a slip of paper.

Article

31 Jul 2026

Amending a prior year, and how far back you can reach

Filed is not the same as settled. The window is limited, and one year falls off the end for every year you wait.

An older man and a young woman lean over an open folder together behind a shop counter.

Article

29 Jul 2026

Selling to your children without a surprise

A family sale is held to a standard, and a price nobody can defend can be treated as partly a gift.

A woman in a flour-dusted apron sits on a low bench in a bakery store room, hands clasped, papers beside her.

Article

28 Jul 2026

When an S corp costs more than it saves

The saving scales with profit. The cost does not. Below a certain point the administration eats the whole thing.

A woman sits at a kitchen table with an older woman, papers and a calculator between them.

Article

24 Jul 2026

Why your last CPA missed it

Usually not incompetence. An accurate return is a report of a year, and reporting a year is not the same as managing one.

Two women sit at a table covered in paperwork, one talking with her hands, the other taking notes.

Article

21 Jul 2026

One entity, two entities, or too many

Entities are containers. What matters is the order money moves between them, and whether the paperwork agrees.

A woman in a work polo stands at the open back doors of a service van, holding a clipboard.

Article

14 Jul 2026

The LLC does almost nothing for your taxes

Liability and taxation are separate questions. Forming the company answers only one of them.

A man sits in the cab of an old pickup truck, holding a cup and a folded receipt at the wheel.

Article

7 Jul 2026

The accountable plan, and why your reimbursements are not deductible yet

You already spent the money. What is missing is the written plan that makes the reimbursement work.

A barber with a towel over his shoulder leans on the back of his chair, looking towards the window.

Article

30 Jun 2026

Electing out, changing your mind, and what it costs

The structure that fitted three years ago may not fit now. Undoing it is slower than doing it was.

A man sits on the open tailgate of a truck in a sunlit yard, a flask beside him, taking a break.

Article

23 Jun 2026

Draws are not income, until they are

You are taxed on what the business earned, not on what you moved to your personal account.

A woman in scrubs stands in a clinic doorway with one hand on the frame, looking down the corridor.

Article

16 Jun 2026

Salary and distribution, and the line between them

Two payments leave the same account and are taxed nothing alike. Where you put the line is the strategy.

A woman on a step ladder in front of full bookshelves turns to look over her shoulder.

Article

16 Jun 2026

My money non-negotiables

Twenty minutes deciding on a $40 subscription, ten seconds on a five figure purchase. That is not a maths problem.

A man and a woman sit at a dining table with notebooks and coffee, mid conversation.

Article

9 Jun 2026

The Augusta Rule, and the part everybody leaves out

A real rule with real conditions. The people who get burned are the ones who skipped the second half.

An older woman sits at her office desk with a notepad, looking towards the window.

Article

9 Jun 2026

The tax code wants you to win

It is a rulebook, not a threat. Congress writes it to get people to behave a certain way, and the behaviour is rewarded on purpose.

A woman trims plants at a bench in a plant shop while a man walks in carrying a watering can.

Article

2 Jun 2026

Putting your spouse on payroll, and when it backfires

Sometimes it unlocks retirement and benefits. Sometimes it just adds payroll tax. Run the comparison first.

A man sits on the front steps of a house at dusk holding a cup, a child's bike behind him.

Article

2 Jun 2026

Debt by itself is not the problem

Not tracking it is. The question was never whether you have debt. It is what the debt is doing for you.

A woman in a cream sweater leans against a desk by a window, reading a single sheet of paper.

Article

2 Jun 2026

Your first year over $500K changes more than your bracket

The rate is the part everyone watches. The phase-outs are the part that actually moves the bill.

A woman sits in an armchair by a window with a mug, a small writing desk behind her.

Article

26 May 2026

The home office deduction is not the trap people think

The audit-magnet reputation is decades out of date. The exclusive use test is the part that still bites.

A woman sits back in an armchair by a window surrounded by plants, hands folded.

Article

26 May 2026

The retirement plan you have is probably not the one you need

You chose it when the business was smaller. The business changed. The plan did not.

A woman sits at a kitchen table at night with a laptop, a ledger and loose receipts, her hand at her forehead.

Article

26 May 2026

Bad books cost you twice

Once in the cleanup, and again in every strategy that turns out to be unprovable when it matters.

Four colleagues stand talking around a workbench in a sunlit workshop.

Article

19 May 2026

Defined benefit plans, the option most owners never hear about

They are not only for large employers. They are for income that is high, stable and expected to stay that way.

A woman leans on a kitchen counter covered in shoeboxes, receipts and printouts.

Article

19 May 2026

The December list, and why most of it should have happened in June

By the time the scramble starts, most of what people are trying to change closed months earlier.

A man in a work jacket stands with a hand on his hip in an empty lot beside a low brick building.

Article

12 May 2026

The property size where cost seg stops paying

The study cost barely moves. The benefit scales with basis. Somewhere between them is a line.

A woman in a blazer sits on a sofa listening to someone across from her, hand at her chin.

Article

12 May 2026

Charitable giving that is structured rather than generous

The same total given in a different shape can produce a very different result on the return.

A young man on a ladder hands a box down to an older man in a hardware store stockroom.

Article

12 May 2026

1099 or W-2, and why getting it wrong is expensive

It is not a preference the two of you agree on. It is a test about control, applied after the fact.

A woman stands with arms folded in front of a wall covered in handwritten notes.

Article

5 May 2026

Buying property in a year you already had a big gain

The two events interact, and whether one can reach the other depends on what kind of income you have.

A woman laughs while handing a stapled document to a man standing in her office.

Article

5 May 2026

Quarterly estimates, and the penalty that is really interest

You paid in full and on time and still got charged. That charge is not a fine. It is rent on money that was not yours.

A woman stands at a whiteboard explaining something to two people seated in front of her.

Article

5 May 2026

What planning actually costs, and what it should return

The honest arithmetic of a fee against what it identifies, including the cases where the answer is to do nothing.

A woman in a winter coat stands in an empty room holding a set of keys, looking up at the ceiling.

Article

28 Apr 2026

Real estate professional status, and who actually qualifies

It is an hours test measured against everything else you do, and most people who claim it would not survive it.

A man carries folded towels in one arm while straightening a sofa in a bedroom.

Article

21 Apr 2026

The short-term rental route, and its own set of rules

Average stay length can move a property out of the standard rental category, which changes the test you have to meet.

An older man sits at a diner counter with a coffee and a folded note, looking down.

Article

14 Apr 2026

Depreciation recapture, the bill nobody budgets for

The deductions were a loan against the sale. Here is how to know the number before you agree a price.

An older couple stand together on the back porch of a house, one of them holding a folder.

Article

7 Apr 2026

1031 exchanges and the clock you cannot stop

The intermediary has to be in place before closing, and the windows run from the sale date whether you are ready or not.

Episode art

Podcast

Episode 37 · 29 min

Buying property in a year you already had a big gain

How the two events interact, and why the order you do them in changes the number.

Any of this sound like your year?

Two minutes will tell you which of these applies to you specifically.

Start the Snapshot

Indexed by the situation you are in.

Unused knowledge is worthless

You cannot be too nice in business

Nobody is buying your features

Build the plane while you are flying it

The deduction most owners miss in their first profitable year

Your first year over $500K

What a cost segregation study actually does to your return

Reading an IRS notice without panicking

Selling a business without handing half to the IRS

Equity vesting in a year you cannot control

Asset sale or stock sale, and why the buyer cares

When an S-corp election actually pays for itself

What actually triggers a second look

The planning window on a business sale closes earlier than you think

Hiring your children, the version that holds up

The documentation that turns a strategy into a position

Installment sales, and trading certainty for tax

What a reasonable salary actually means, and who decides

Amending a prior year, and how far back you can reach

Selling to your children without a surprise

When an S corp costs more than it saves

Why your last CPA missed it

One entity, two entities, or too many

The LLC does almost nothing for your taxes

The accountable plan, and why your reimbursements are not deductible yet

Electing out, changing your mind, and what it costs

Draws are not income, until they are

Salary and distribution, and the line between them

My money non-negotiables

The Augusta Rule, and the part everybody leaves out

The tax code wants you to win

Putting your spouse on payroll, and when it backfires

Debt by itself is not the problem

Your first year over $500K changes more than your bracket

The home office deduction is not the trap people think

The retirement plan you have is probably not the one you need

Bad books cost you twice

Defined benefit plans, the option most owners never hear about

The December list, and why most of it should have happened in June

The property size where cost seg stops paying

Charitable giving that is structured rather than generous

1099 or W-2, and why getting it wrong is expensive

Buying property in a year you already had a big gain

Quarterly estimates, and the penalty that is really interest

What planning actually costs, and what it should return

Real estate professional status, and who actually qualifies

The short-term rental route, and its own set of rules

Depreciation recapture, the bill nobody budgets for

1031 exchanges and the clock you cannot stop

Buying property in a year you already had a big gain

Any of this sound like your year?

Occasional notes on planning ahead.