Long-form · Vol. I
Essays on email for
one reader, many domains.
A small shelf of long pieces — written to work as standalone essays, not as lead-gen posts. The through-line is the same category we argue everywhere else on this site: that the inbox for one person running many businesses is a real, under-served product category, distinct from the single-self mail client that has dominated since 2006.
Email for the portfolio entrepreneur
Why one reader with five businesses is not five readers with one — and why the inbox has been built for the wrong person for fifteen years.
Read the essay →Google Workspace is priced per user.
Workspace's $7/user/month is correctly priced for what it is. It is also the wrong unit for a portfolio entrepreneur, and the arithmetic adds up faster than most solo operators expect.
Read the essay →SPF, DKIM, and DMARC for solo founders.
The three DNS records that keep your email out of spam folders — written for founders who'd rather ship a product than read an RFC. A plain-English field guide.
Read the essay →One person, five brands — a sending-identity playbook.
A custom-domain email and sending-identity playbook for solo operators: when to bind a new domain, when an alias is enough, and when the two-domain shortcut costs more than it saves.
Read the essay →What the 'via' line in Gmail really means.
That small grey "via amazonses.com" next to a sender's name is telling you something specific about DKIM alignment. Here's what, why it hurts open rates, and how per-domain DKIM fixes it.
Read the essay →Gmail aliases vs. true multi-domain email.
Gmail's 'Send as' is a useful vanity setting for a single self who occasionally needs a second address. It is structurally the wrong abstraction for an operator running more than one business. Here's where it breaks — specifically.
Read the essay →How to set up email for multiple LLCs — one operator, separate entities.
Running several LLCs from one desk means each entity’s email should stay legally and reputationally separate — its own domain, its own DKIM key, its own reply-From — while one person still reads everything in one place. You have three building blocks: a separate domain per entity, an alias on an existing domain, or a subdomain. This is the decision tree for which to use, and what each one costs.
Read the essay →Why Apple Mail stopped syncing your Microsoft 365 account.
Microsoft has started retiring Exchange Web Services, the connection the Mac’s built-in Mail, Calendar, Contacts, Notes and Reminders still use for work and school accounts. Your iPhone is fine. Here is how to tell if this is your problem, the admin fix, the stopgaps, and what Apple says is coming.
Read the essay →
Sources
New pieces, quarterly-ish.
Folio publishes long-form writing about email and multi-identity operation on a slow cadence. If you'd like to be notified when a new piece lands, the fastest subscription is to start a trial and add writing@wm.emcognito.com to your contacts — new pieces are mailed there first.