Winter Email Templates for Past Clients
Builds guide sites for a livingPublished July 22, 2026Last updated July 26, 202634 min read
- 26 CFR 1.162-20(a)(2) treats advertising that keeps the taxpayer's name before the public as deductible where it relates to patronage the taxpayer might reasonably expect in the future.
- Apply that future-patronage test to the list every November: a two-hundred-name list usually cuts to about sixty, and the sixty open at a rate the two hundred never did.
- Send the season in pictures before Thanksgiving asking for nothing, because the November reply is what the January booking conversation is built on.
- Name which weeks book first in the January email, since it is true, unavailable elsewhere, and creates a deadline you did not have to invent.
- The late-February knowledge email must be usable by somebody who never books again, which is the test that keeps it honest and the reason it gets forwarded.
- Personalise the March email to the weeks each client has actually fished, which the trip records already tell you.
The Treasury regulations recognise a category of business spending whose entire purpose is keeping the taxpayer's name before the public, and they make it deductible only where the spending is related to the patronage the taxpayer might reasonably expect in the future.
That second clause is the best editorial test available for a winter email. Not whether it is charming, not whether anybody replies, but whether the people receiving it are people whose future business you could reasonably expect. Run four winters of email through that filter and most of what usually gets sent falls out. What follows is the calendar, the four things worth sending, and the reasoning behind each. Nothing here is tax advice; the regulation is used as a standard of judgment, not a deduction strategy. The rest of the retention material is indexed on the running the business hub.
| When | What it is | What it asks for |
|---|---|---|
| Late November | The season in review, with photographs | Nothing |
| Early January | Next year's calendar, with the dates that go first | A date |
| Late February | One piece of water knowledge, useful on its own | Nothing |
| Late March | What is left, stated plainly | A date |
What does the regulation actually recognise?
Advertising that sells nothing, as a legitimate category.
Paragraph (a)(2) of section 1.162-20 of the income tax regulations addresses institutional or good will advertising, and says expenditures for advertising which keeps the taxpayer's name before the public are generally deductible as ordinary and necessary business expenses, provided they are related to the patronage the taxpayer might reasonably expect in the future.
The examples it gives are striking, being advertising that encourages contributions to organisations such as the Red Cross, or the purchase of United States Savings Bonds, or participation in similar causes.
None of which sells the advertiser's product, and all of which the regulation treats as ordinary business spending anyway.
What makes them deductible is not the presence of an offer but the presence of an audience whose future custom is a reasonable expectation.
Section 1.162-20 is carried on the eCFR.
The list this gets sent to is built in the client database piece.
Why does the future-patronage clause matter here?
Because it separates a mailing list from an audience.
Everybody who has ever given you an email address is a list; the people whose future business you could reasonably expect are something smaller and more valuable.
A one-off client from a corporate group four states away, who fished because a colleague organised it, is on the list and is not in the second category.
Sending them four emails a winter is not retention, it is volume, and it is the reason most guide mailing lists quietly stop being opened.
Applying the test properly usually cuts a two-hundred-name list to about sixty, and those sixty open at a rate the two hundred never did.
The discipline is annual: before the November send, go down the list and ask of each name whether their future business is a reasonable expectation.
Where the answer is plainly no, they come off, and nothing bad happens.
How the list gets pruned mechanically is dealt with by the spreadsheet CRM piece.
Why four emails and not twelve. Sixty names, four sends, is 240 emails a winter, each of which takes zero marginal minutes once written. The constraint is not cost, it is attention: a list that hears from you monthly stops reading, and a list that hears from you twice a winter has forgotten you by March. Four sends, spaced roughly six weeks, is the shape that fits a season with two booking peaks in it. If two of the four ask for nothing, the two that do ask arrive from somebody who has not spent the winter selling. Those numbers are a judgment about spacing, not a measured result.
What goes in the November email?
The season, in pictures, asking for nothing.
This is the clearest case of the good-will category: it keeps your name in front of people, it sells nothing, and its value is entirely in the future.
The content is the year, honestly told, meaning the water that fished well, the water that did not, and eight or ten photographs of clients with fish.
The photographs are the email; the writing is a caption service around them, and three hundred words is plenty.
What matters is that people appear in it, because a past client scanning for themselves or somebody they know is the entire mechanism by which this email gets read twice.
It closes with thanks and a note that next year's dates open in January, which is information rather than an ask.
Sending it before Thanksgiving rather than after puts it in a quieter inbox than December's.
What else the season's end has to close out is listed in the fall wrap-up piece.
This is not tax advice. Section 1.162-20 is quoted as a standard of editorial judgment, not as guidance on what a guiding business may deduct. Whether any particular expenditure is deductible depends on facts this page knows nothing about. Speak to a tax professional about your own return. Commercial email is separately regulated at federal and state level, including requirements about sender identification, subject lines and a working unsubscribe mechanism; none of that is analysed here and it does carry real consequences.
What goes in the January email?
The calendar, and which dates disappear first.
January is the one send of the four that is straightforwardly commercial, and it works because November's was not.
The structure is short: the season opens on a date, these are the weeks that book first, and here is how to take one.
Naming which weeks go first is the substance, because it is true, it is information the client cannot get anywhere else, and it converts a vague intention into a decision with a deadline attached that you did not have to invent.
Whatever you write here has to be accurate, since a claim that the first two weeks of June always go first is checkable against what you tell somebody in March.
Past clients get this email before it goes anywhere else, and saying so is both true and worth saying.
One reply-to address, no booking link buried in an image, and a note that answering this email is a fine way to book.
What the booking page has to do once they click is set out in the booking page piece.
What goes in the February email?
Something genuinely useful, unconnected to booking.
The late-winter email is the hardest of the four to write and the one that does the most work, because it is the only one that gives the reader something they keep.
A knot, a fly, a rigging change, a read on how the winter's snowpack shapes the spring, or a plain explanation of why one stretch fishes better at a particular flow.
It should be usable by somebody who never books with you again, which is the test that keeps it honest, and it should be specific enough that a competent angler learns something.
This is the email that gets forwarded, and forwarding is the only organic growth a guide's list ever gets.
It closes with nothing, or at most a line noting how the calendar is filling, and it must not turn into a pretext at the last paragraph.
The regulation's own examples are the model: content that sells nothing, sent because the audience is one whose future business is a reasonable expectation.
How the same material works as public writing is examined in the blogging piece.
What goes in the March email?
What is actually left, with no decoration.
By late March the season is close enough that the people who intended to book and did not are reachable with plain information.
The message is a list: these dates are gone, these are left, here is what is open in the weeks you have fished before.
Personalising that last clause is the whole trick, and it is possible because the trip records say when each person fished.
A client who has fished the second week of June three times does not need a general calendar; they need to know whether that week is still available.
Which turns a broadcast into something that reads as individual, without any of the pretence that usually accompanies that effect.
It is the shortest of the four, it asks directly, and it is the last email until November.
Saying so plainly, that this is the last one until the season ends, is worth a line.
The numbers that tell you whether any of it worked are assembled in the repeat rate piece.
What should the subject lines look like?
Descriptive, boring, and true.
A subject line that describes the contents is opened by the people who want the contents, which is the only opening rate that matters.
The 2026 season in pictures, or Next year's dates open Monday, or Why the lower river fishes better at 900 cfs.
What underperforms in practice and overperforms in tests is the curiosity line, meaning any subject engineered to be opened without disclosing what is inside.
It raises opens and lowers everything downstream, because the reader who opened without wanting the contents closes immediately and learns to distrust the sender.
Across four sends a winter to sixty people who know you personally, that trade is plainly bad.
Your own name in the from field does more than any subject line, which is an argument for sending from a personal address rather than a business one.
The same principle applied to text messaging is set out in the text scripts piece.
Should these be plain text or designed?
Plain, except November.
Three of the four emails are somebody you know writing to you, and a template with a header banner and a coloured button announces that they are not.
Plain text, sent from your own address, with a normal signature, is read as correspondence, and correspondence gets replies where marketing gets archived.
November is the exception because it is a photograph email, and photographs need a layout, so a simple one-column image list is right there.
Even then, the writing around the images stays in the same voice, and nothing about it should look like it came out of a template gallery.
The practical benefit is deliverability, since plain personal mail from a personal address is less likely to be filed as promotional than a designed template.
The practical cost is that you cannot measure opens reliably, which is a real loss and a smaller one than being archived unread.
What to measure instead is worked through in the numbers piece.
Who should be removed from the list?
Anyone the future-patronage test cannot honestly cover.
The corporate one-off who did not organise the trip and lives four states away.
The client who told you a bad day was your fault, whether or not it was, because a winter email to them is not a retention act.
Anybody who has not opened four consecutive sends, since the list is now costing you sender reputation for nothing.
And anybody who asked to come off, immediately and permanently, which is both a legal matter and the easiest possible way to damage a reputation in a small trade.
Removal is not a loss; the list is an asset measured by who reads it, not by how long it is.
A sixty-name list where fifty read every send is worth more than a four-hundred-name list where forty do.
Where the removals get recorded is dealt with by the spreadsheet CRM piece.
How should the list be split?
Two groups, and the split is by year rather than by value.
People who fished in the last twelve months, and people who did not, because those two groups need different March emails and identical November ones.
The recent group already knows what your season looks like and needs only the dates; the older group needs a sentence reminding them who you are before anything else lands.
Splitting by spend instead is the instinct and it is usually wrong, since the highest-spending client in a guiding business is often a corporate one-off with no future in them at all.
Two groups is also the practical ceiling for something done by hand, and the moment it becomes five, the whole programme stops happening in February.
Where a third split earns its keep is by water, for an operation that runs two genuinely different fisheries, because the February knowledge email is only useful to one of them.
Beyond that the returns collapse fast and the effort does not.
How the segments are stored is covered by the segmenting piece.
What about the people who reply?
They get answered by hand, same day, and that is the actual product.
A winter email programme that generates eleven replies and answers them in a batch on Sunday has thrown away most of what it earned.
The reply to a November email is usually not a booking enquiry at all; it is somebody saying that was a good day, which is an opening rather than a transaction.
What that reply deserves is two or three sentences about their specific day, which you can write because the trip record says what happened, and no ask attached.
The booking conversation follows in January from somebody who has now had a real exchange with you, and it converts at a rate no cold sequence approaches.
Which is the whole reason the November email asks for nothing: it is buying the reply, not the booking.
Treating those replies as an inbox chore rather than as the return on the send is the commonest way this programme quietly fails while appearing to run.
What does a good February email look like in practice?
One narrow subject, explained properly, with a number in it.
Not five tips, not a roundup, and not anything with a listicle shape, because those read as filler regardless of how good the content is.
One question, asked and answered: why the lower stretch turns on at a particular flow, what the winter's snowpack means for the runoff window, or how to rig for a specific condition that catches people out every spring.
A real number in it does more than anything else, because a number is checkable and it signals that the writer is looking at data rather than reminiscing.
Four hundred to six hundred words is the shape, which is long enough to say something and short enough to be read on a phone at a kitchen table.
If it took you twenty minutes to write, it is probably not specific enough; the good ones come from something you actually noticed last season and had to think about.
The test at the end is simple: would a competent angler who never books with you still be glad they read it.
What is the honest limit of this?
It retains; it does not acquire.
Four emails a winter to sixty past clients will fill some days that would otherwise have gone empty, and it will do nothing whatever about a calendar that is half empty because not enough people know you exist.
The regulation's own framing makes this plain: good-will advertising is deductible because it relates to patronage reasonably expected, and patronage from people who have never met you is not reasonably expected from an email they never signed up for.
Which is worth saying because the winter email programme is the thing guides reach for when bookings are soft, and it is the wrong instrument for that problem.
It is the right instrument for a different one, being the slow erosion of a client base that would otherwise lose a fifth of itself a year to nothing but forgetting.
Run both, and expect this half to hold the floor rather than raise the ceiling.
The acquisition half of the problem is examined in the first clients piece.
Where does a winter programme usually fail?
Five ways, and the list is the first.
Sending to everybody who ever gave an address, so the future-patronage test is never applied and the open rate decays until nobody sees anything.
Making all four emails commercial, which turns the programme into a quarterly sales campaign and gets it filed accordingly.
Designing them, so three emails that should read as correspondence announce themselves as marketing before a word is read.
Writing curiosity subject lines, which buys opens with trust and is a bad trade on a list of sixty people who know you.
And skipping February, which is the send that costs the most effort, returns nothing measurable, and is the only one that earns the other three.
The equivalent failure in the reactivation sequence is examined in the win-back piece.
What is the working programme?
Four sends, two asks, one honest list.
Prune the list every November against the question of whether that person's future business is a reasonable expectation, and accept that it gets shorter.
Send the season in pictures before Thanksgiving, asking for nothing.
Send the calendar in early January, naming which weeks go first, and let past clients have it before anybody else.
Send one genuinely useful piece of water knowledge in late February, usable by somebody who never books again.
Send what is left in late March, personalised to the weeks each person has actually fished, and then stop until November.
The statutory basis for deducting ordinary and necessary business expenses is 26 U.S.C. 162, with the regulation mirrored on govinfo.
What to do with the people who never respond to any of it is dealt with by the win-back piece.
How this was checked. The treatment of institutional or good will advertising comes from 26 CFR 1.162-20(a)(2), which provides that expenditures for institutional or good will advertising which keeps the taxpayer's name before the public are generally deductible as ordinary and necessary business expenses provided the expenditures are related to the patronage the taxpayer might reasonably expect in the future, and which offers as examples advertising that keeps the taxpayer's name before the public in connection with encouraging contributions to such organizations as the Red Cross, the purchase of United States Savings Bonds, or participation in similar causes. The same paragraph adds that expenditures for advertising presenting views on economic, financial, social or other subjects of a general nature are deductible if they otherwise meet the requirements of the regulations under section 162, provided they do not involve the lobbying and political-campaign activities dealt with elsewhere in the section. Paragraph (a)(1) sets out the scope of the section, which principally governs the deductibility of lobbying, legislative and political campaign expenditures. Section 1.162-20 was read on the Electronic Code of Federal Regulations on 26 July 2026. It is quoted here as a standard of editorial judgment about who a communication is for, not as guidance on what any business may deduct, and nothing on this page is tax advice. Federal and state law separately regulates commercial electronic mail, including sender identification, subject line accuracy and unsubscribe requirements; no part of that body of law was analysed for this page. No open rate, click rate or conversion benchmark for guide email is asserted, because no consulted source publishes one for this trade; the send counts and list sizes used above are stated illustrative assumptions and judgments about spacing.
If your booking calendar has more open weeks than you’d like, I’ll build you a free preview of your booking site before you pay a cent.
Get a free website previewWhat goes in each of the four sends, who comes off the list, and why three of them should be plain text
What does the regulation recognise?
26 CFR 1.162-20(a)(2) addresses institutional or good will advertising and provides that expenditures for advertising which keeps the taxpayer's name before the public are generally deductible as ordinary and necessary business expenses provided they are related to the patronage the taxpayer might reasonably expect in the future. Its examples include advertising encouraging contributions to organisations such as the Red Cross or the purchase of United States Savings Bonds, none of which sells the advertiser's product. It is quoted here as a standard of judgment, not as tax advice.
Who should be on the list?
People whose future business is a reasonable expectation, which is a smaller group than everybody who ever gave you an address. The corporate one-off four states away who fished because a colleague organised it is on the list and does not pass the test. Applying it properly usually cuts a two-hundred-name list to around sixty, and nothing bad happens when the rest come off.
What goes in the November email?
The season, in photographs, asking for nothing. Eight or ten pictures of clients with fish, three hundred words of honest account covering the water that fished and the water that did not, thanks, and a note that next year's dates open in January. People appearing in it is the mechanism: a past client scanning for themselves or somebody they know is why it gets read twice. Send it before Thanksgiving, into a quieter inbox than December's.
What makes the January email work?
Naming which weeks book first. It is true, it is information the client cannot get anywhere else, and it converts a vague intention into a decision with a real deadline attached rather than a manufactured one. Past clients get it before anybody else, which is worth saying because it is the case. One reply-to address, and a note that answering the email is a fine way to book.
Why send a February email that sells nothing?
Because it is the only one that gives the reader something they keep, and it is the send that earns the other three. One narrow subject explained properly, with a real number in it, usable by somebody who never books with you again. That last constraint is the test that keeps it honest. It is also the only email that ever gets forwarded, which is the only organic growth a guide's list gets.
Plain text or a designed template?
Plain for three of the four, sent from your own address with a normal signature, because correspondence gets replies where marketing gets archived. November is the exception, since it is a photograph email and photographs need a layout. The cost of plain text is that open tracking becomes unreliable, which is a smaller loss than being filed as promotional and never read.
Will this fill a half-empty calendar?
No, and it is the wrong instrument for that. Four emails to sixty past clients will fill days that would otherwise have gone empty and will do nothing about not enough people knowing you exist. The regulation's own framing makes the limit clear: patronage from people who have never met you is not reasonably expected. Run this to hold the floor and run acquisition to raise the ceiling.
Sources & methods
- 26 CFR 1.162-20 on the Electronic Code of Federal Regulations, read for paragraph (a)(2) on institutional or good will advertising, which provides that expenditures for institutional or good will advertising which keeps the taxpayer's name before the public are generally deductible as ordinary and necessary business expenses provided the expenditures are related to the patronage the taxpayer might reasonably expect in the future, and which gives as examples advertising that keeps the taxpayer's name before the public in connection with encouraging contributions to such organizations as the Red Cross, the purchase of United States Savings Bonds, or participation in similar causes; and for the further statement that expenditures for advertising presenting views on economic, financial, social or other subjects of a general nature are deductible if they otherwise meet the requirements of the regulations under section 162. Paragraph (a)(1) was read for the scope of the section, which principally governs lobbying, legislative and political campaign expenditures. Nothing on this page is tax advice and no conclusion about the deductibility of any expenditure is offered.
- 26 U.S.C. 162 at the Office of the Law Revision Counsel, cited as the statutory basis for the deduction of ordinary and necessary business expenses that the regulation above interprets. The section was consulted only for that relationship.
- The 2024 annual edition of 26 CFR 1.162-20 published on govinfo, used as an independent copy of the regulation quoted above. Federal and state law separately regulates commercial electronic mail, including sender identification, subject line accuracy and unsubscribe requirements; no part of that body of law was analysed for this page. No open rate, click rate or conversion benchmark for guide email is asserted because no consulted source publishes one for this trade.
Every figure here is traced to a named public source and checked against it. Licensing, tax, and fee rules change. Verify your state’s current rules with the agency directly before you count on any number here.
Evan Knox
I build booking websites and run the ads and search for owner-run fishing guides, one operation per stretch of water. My first guide client, Bowman Fly Fishing, grew its revenue 4x in a year from that work. Field Notes is where I put the straight numbers on the business of guiding.
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Email holds the floor. It does not raise the ceiling.
I'm Evan. Winter email keeps the clients you have. I build guides the booking site and run the ads that find the ones you don't. Free preview before you pay a cent.