WordPress, agency life, and entrepreneur observations
Excerpts from The Friday Chaser
Sales call process
As cringy as it’s been, I’ve started rewatching my sales call recordings. I started recording them earlier this year (and no, no one has ever had a problem with it 🤷), so I have a…
Oct 16, 2026
Don’t say no for them
I still remember making my first website sale. I couldn’t believe that someone was going to pay me $500 to build a website. It honestly felt like winning the lottery. I’ve been thinking about that…
Oct 9, 2026
A good enough excuse
I’ve always been a competitive person. When there’s something I need to do, but I can’t find the motivation to get it done, I will often “gamify” it. It’s a cheap trick to play on…
Oct 2, 2026
Between thinking and doing
It’s funny how one tiny thing can make or break an entire day. An email from a client telling you how much they love their new website and thanking you for all your hard work…
Sep 25, 2026
The juice isn’t worth the squeeze
It’s one of my all-time favorite sayings: “The juice isn’t worth the squeeze”. In case that’s an American or southern thing, all it means is that the reward isn’t worth the effort. Or, in business…
Sep 18, 2026
What’s in your way?
When I get stuck on something, I have this bad habit of thinking that I can just keep doing more and pushing harder to brute force my way through it. It’s the kind of “solution”…
Sep 11, 2026
Why all your leads are referrals
There are two big used car dealerships in town. The first one is just 5-minutes down the road. A nice facility, and they have a few cars you’re interested in. The second one is a…
Sep 4, 2026
One business development task a day
It’s been years now since I first heard this advice, but it’s one of the few that stuck with me since the moment it left Pete Everitt’s lips. One business development task a day. I…
Aug 28, 2026
Your tribe is good for your soul
Attendance was noticeably down at WordCamp US this year. That was especially evident at the vendor hall, where my usual haul of swag yielded just one free shirt! And, everyone was right… Phoenix in August…
Aug 21, 2026
Are you a gatekeeper?
This week I’ve spent 5 hours looking at 40 agency owners’ books. That’s Board Meeting week inside our TABLE groups where we drop the normal agenda so everyone can report on how things went in…
Aug 14, 2026
Be-Back Bus
I knew when the “developer” who was going to take over my client’s site 2 years ago didn’t know how to migrate a website or point DNS that it would eventually end in disaster. Honestly,…
Aug 7, 2026
Try failing more
I remember back when I started my business, I had a lot of wacky ideas. I printed flyers and slipped them under the door of the downtown businesses. I set up a system to help…
Jul 31, 2026
Maybe this time will be different
This week I had the opportunity to be interviewed on The Melapress Show. It was a fun conversation where we talked about qualifying clients, the sales process, and paid discovery. But afterward, it was the…
Jul 24, 2026
Confidence is the byproduct of the routine
Twelve minutes into a sales call this week, I insulted the prospect’s entire business model. Not on purpose… It just… fell out. The entire call, I couldn’t find my words. I bounced back and forth…
Jul 17, 2026
The tide going out
Summer is in full effect (at least for those of us up here in the northern half of the globe). While our industry isn’t as seasonal as something like a ski resort, there are patterns….
Jul 10, 2026
The opportunity telescope
This week we closed out a month, a quarter, and officially crossed the half-way mark on the year. How’s it going for you, {name}? More importantly, how are you measuring things? Since very few of…
Jul 3, 2026
It never pencils out
I had a conversation this week with some other agency owners about their “favorite clients”. You probably have a client or two that comes to mind instantly. They let you do your thing. They pay…
Jun 26, 2026
Someone else will
There’s a concern I hear a lot when agency owners talk about going back to existing clients and pitching new work. People are worried that if they suggest accessibility fixes or SEO improvements their clients…
Jun 19, 2026
What happens next
I try not to do a lot of content on AI. Not that I’m not thinking about it, simultaneously impressed and disgusted by it, and using it… It just seems like you’re probably already getting…
Jun 12, 2026
After you get a nibble
As we wrap up this mini-series on the most underrated agency assets, we’re going to take a slight detour away from “marketing” in the traditional sense. In the past 4 issues, we’ve talked a lot…
Jun 5, 2026
