A "top secret" planning session got me thinking

It's nice to get sound advice

I am a part of a small internet-based entrepreneur’s group that meets once a week. There’s a lot more to talk about on that front, but at a date in the undetermined future.

With a lot of irons in the fire right now, I told the group that for the time being, my primary focus is on writing email newsletters and putting them on Substack. A bunch of other stuff, but the newsletters are what I want to put the bulk of my attention toward.

I explained that it is slightly different than writing an email newsletter because there are other people who read these newsletters now, not just the people that have been on my list.

I now have my own Substack page where the “archives” are now held. Easy access.

If you are reading this and are one of those people NOT on my email list, you’re really the person who I’m trying to reach today.

If you do get these emails on a regular basis, you are still encouraged to read on because there is probably something of value &/or entertainment as you continue on.

Nevertheless, I’d like to invite you to sign up with us if you haven’t already. All you need to do is click the button and enter your email in the opt in form.

As the kids say, “easy peasy [lemon squeezy],” right?

Not so fast.

Most people don’t like to just “give out” their email to any Tom, Dick, or Harry. Personally, giving my address to a Harry would be tough. I don’t care so much about passing on my info to Toms or Dicks.

Tom was the name of my father and Dick was his father’s name. So, I’m comfortable in that department. Heck, my mentor Tom Woods facilitated this entrepreneur’s group that got me to thinking about today’s email.

Ol’ Woods sends me email every day at two different email addresses. I’m good with the Toms, for sure.

But there is a real concern that the wrong people will get a hold of your email and make your life miserable. The fear is that if you give up your email address to any ol’ Harry, you’ll get spammed.

Valid concern.

The nice thing about signing up for email newsletters is that you can try them out. Opting out of email lists has never been easier.

Email filters help immensely. I subscribe to 20 or more email newsletters and most of them come nearly every day.

We’re really in a new age of newsletters as far as I can tell.

“Why do I need to sign up for your Substack?”

You don’t. I think you should, though.

I could prattle on about the benefits, but I won’t. Inevitably, someone will have a something to say for every point.

Ever seen that SNL skit with Nicolas Cage about “Baby Names?” An objection at every turn, no matter how reasonable. Hilarity ensues.

I really don’t want folks to sign up if they are not going to read. What’s the point?

Since signing up for Substack myself—it is really easy and I should have done it years ago—I’ve subscribed to several more newsletters that I now read every day. I usually read them in my email inbox on my computer, but if I’m on my mobile device, I use the Substack app, and that is nice because it collates the list of newsletters you signed up for. Same stuff you get via email. Only newsletters, no other email.

My commitment is that we’ll bring you, the reader, something good to read with each newsletter. Just by being on this platform, it has helped to focus my content.

For a little more Q & A:

“Are you a sportswriter?”

Kinda, but no. Sportswriters as a class of people are loathsome and I’d prefer not to be identified with windbags like [bring out the usual suspects]. There are some good ones out there, but few and far between. The Godfather, Dwight Jaynes is one sportswriter in particular who I grew up reading and whose career I respect.

I write about sports sometimes because I like sports. Most of my life has been consumed by sports.

With any of my emails, if I don’t like what I wrote, the send button never gets clicked. Some workdays end up being totally fruitless.

As far as writing about sports and sports-only, there is a lesson in there to be found in one of my favorite all-time novels, The Sportswriter by Richard Ford. Pretty much a study in why you don’t want to take on “sportswriting” as your day job.

The “blurb” for Ford’s masterpiece:

As a sportswriter, Frank Bascombe makes his living studying people--men, mostly--who live entirely within themselves. This is a condition that Frank himself aspires to. But at thirty-eight, he suffers from incurable dreaminess, occasional pounding of the heart, and the not-too-distant losses of a career, a son, and a marriage. In the course of the Easter week in which Ford's moving novel transpires, Bascombe will end up losing the remnants of his familiar life, though with his spirits soaring.

I prefer flexibility over sportswriting.

This format allows for flexibility.

“Are you a political junkie?”

No, but there are a lot of idiots in this world to skewer and the political arena is a target-rich environment.

“Do you want to write for a newspaper?”

Those days are behind me, but if the right opportunity comes up…

I simply prefer writing to “our people”—sane and thoughtful folk, rather than trying to impress some faceless mob of donkeys who do nothing bray at the outside world after consuming their local fishwrap’s regular pairing of puff-pieces and propaganda.

But…you never know. Stranger things have happened.

“What else do you have in store?”

Lots. But for now, we’re going to still continue with our regular “exclusive content” available only to paid subscribers. I call it “long-form” and these posts/emails will be a few times per month and take the place of short e-books or magazine-type articles that we had planned on doing.

'Tis roughly 14¢ per day out of one’s pocket to help keep the hamster wheel in my brain spinning in concert with my typing fingers.

I can’t promise much other than writing daily emails that are like the ones I like to read.

One thing I can promise, however is that the more subscribers we get, the more premium exclusive content we’ll put out there.

Drop your email into this here box if you haven’t done so already…

Share us around. Go through the archive and pick out your favorite old email and send it to a friend…as an email. Works beautifully.

Brian O'Leary