Session 6.2 · The Email Newsletter

Stay top of mind, at scale

Of every touch on your stay-in-touch calendar, the newsletter is the workhorse, because it is the one that reaches everyone at once for almost no effort per person. Most advisors hear newsletter and picture a chore, a glossy thing they have to design and dread. Let go of that picture completely. A newsletter is simply the easiest, lowest-pressure way on earth to stay in front of your whole list, so that when a trip finally comes up in someone's life, you are the name already sitting in their head. That is what this session builds: a letter you will actually keep sending.

Out of sight is out of business

People do not leave you because they got angry. They leave because they forgot. A client books a wonderful trip, loves you, fully intends to use you again, and then eighteen quiet months go by and a coworker mentions an advisor, and they book with that person, not because they liked them more, but because that person was simply in front of them at the right moment. That is the leak: not a complaint, just a fade. A newsletter plugs it, gently and at scale. It keeps you in front of everyone at once, so when the someday trip finally becomes a real one, your name is the one already in their head.

A simple, repeatable format

The reason most advisor newsletters die after issue two is that they were too ambitious. A glossy magazine you dread building is a newsletter you stop sending. So keep it dead simple and the same every time: a warm personal note from you, one genuinely useful idea or destination, and one gentle invitation to reach out. That is it. A format you can fill in your sleep is a format you will still be sending a year from now. Boring and consistent beats brilliant and abandoned, every single time.

Be a person, not a brochure

What do you actually write about? Be a person, not a brochure. Write about a trip you genuinely loved, a destination that is having a moment, a real travel tip, a behind-the-scenes story, a quick where-to-next idea. Things that are useful or human. What you do not do is fill it with a wall of sales pitches and generic supplier copy anyone could send, because promotional noise gets ignored and unsubscribed, while the personal, useful note gets read and keeps you welcome in the inbox. Give them something worth opening, and they keep opening.

A cadence you can keep

Once a month is plenty. Once a quarter still works. What matters is not frequency, it is that you actually keep it, because a newsletter that shows up reliably builds trust, and one that vanishes for a year and reappears feels like a stranger. Pick a cadence you can sustain on your worst, busiest month, then protect it. And here is where it stops being a burden: your Second Mate can turn a few bullet points into a finished, warm newsletter in minutes. You bring the idea and the personal note, it does the heavy lifting of the writing. That is how the dread disappears and the rhythm survives.

Put your Second Mate to work

Real jobs: it drafts the whole newsletter from bullets, suggests a month of topics, and writes subject lines. Copy-paste prompts in the library.

The newsletter is where your Second Mate earns its keep, because writing is exactly the friction that kills the habit. Hand it a few rough bullet points and it writes the whole warm newsletter in your voice. Stuck on what to even send? Ask it for a month of newsletter ideas tied to your niche. And do not skip the subject line, ask it to write one worth opening, because a great letter nobody opens did no good. You bring the idea; it removes the blank page.

Set up the system, pick your sender

The point: stand up a repeatable system, not a someday. Draft it, pick one sender, set it to send on a fixed day each month.

Here is how you make this run on its own, so you are never staring at a blank page on the first of the month. Three moves. One, let your Second Mate draft it: hand it your recent trips and notes and it writes the letter, then you add the human warmth on top. Two, pick the system that actually sends it. That is either your CRM's built-in email, or a dedicated email platform, and the three I would point you to are Constant Contact, Wix, or Kit, which is kit.com, the one that used to be called ConvertKit. Pick one, just one, and import your list into it. Three, set it to send: build one simple template you reuse every time, let your Second Mate draft the issue, you warm it up, then schedule it for a set day each month. That is the whole system. Once it is standing, the newsletter stops being a decision you dread and becomes a rhythm that runs itself.

Your first brick: build your newsletter

Here is your work, and we do it together. One, lock your format, your three simple parts: a note from you, one useful idea, one gentle invitation. Two, pick your cadence, the rhythm you can keep on your busiest month. Three, draft issue one, hand a few bullets to your Second Mate and actually ship your first newsletter. Do not wait until it is perfect. A sent newsletter beats a perfect draft sitting in your head.

Want a hand with this part?

And if you have been meaning to start a newsletter for years, or you started one and it fizzled, or you just freeze every time at the blank page, this is exactly what we are here for. Three doors. Bring your idea to Professor Hours and we will shape your first issue. Book a one-on-one and we will set up your platform and your format together. Or hire us and we will build it with you. The hardest part is starting; we start it with you.

Into 6.3, the personal touchpoints

The newsletter speaks to everyone at once, and that is its power. But some moments deserve a message meant for one person only. The next route is the warmest, most personal touch of all: the anniversary and the birthday, the days that make a single client feel remembered all year. Let us go build those.