Happy Sunday, Everyone! Last week, I had a long meeting with a Founder/CEO of a mid-sized regional services business. He’s incredibly well-known in his specific niche (read: he’s a mini-celebrity among those who share his speciality). His business is substantial and growing, and like any good CEO, he’s always looking for opportunities to improve. That, of course, led us to AI. But not automations or apps or vibe-coded tools to support his business. He was fundamentally bored by those...
17 days ago • 18 min read
Happy Sunday, Everyone! I spent a great deal of time over the past few weeks talking to investors + bankers, most in the senior living and age-tech spaces. One of the most illuminating conversations - and the one I’d argue is most applicable to everyone here - centered on their underwriting. I know, I know - that’s one topic just about everyone (including bankers) dreads - but the implications of it are massive. Hence, today’s newsletter. Yes, the example will center on senior living, but the...
24 days ago • 11 min read
Happy Sunday, Everyone! I hope you all had a fantastic week! I spent most of mine in sunny Las Vegas at the Senior Care Marketing & Sales Summit (SMASH). This was my 7th year at the event, and each time, the team puts on a truly fantastic show. While there, I had a long conversation with two long-time readers of this newsletter, both of whom were curious about my thoughts on content marketing - where’s going, where it fits in the AI world + what agencies/brands should be doing. Well, never...
about 1 month ago • 17 min read
Happy Sunday, Everyone! And happy Q4…I genuinely don’t know where 2026 went - but somehow, we’re in the home stretch of the year. Tomorrow I'm heading out to SMASH, the Senior Care Marketing & Sales Summit, for 3 days with some of the best operators, sales leaders & marketers in senior living. If you'll be there, drop me a note (just reply to this email) if you’d like to get together. It’s fitting, then, that the idea behind this issue began with a senior living focus conversation. A few days...
about 1 month ago • 13 min read
Happy Sunday, Everyone! It’s almost October. If you work in paid media, that means t-minus 6 weeks until your Meta CPMs take their annual pilgrimage to Mt. Everest (aka spike around Black Friday / Cyber Monday), with your CPAs following them on their meteoric rise. And, like clockwork, there will be a few thousand X posts about “creative fatigue”, while client/agency Slack channels are filled with some variant of: "The creative is fatiguing” or (worse) “We need some FRESH creative.” It's the...
about 1 month ago • 12 min read
Happy Sunday, Everyone! I hope you’re all doing well, enjoying the start of Fall and excited for 2026’s home stretch. Conference season is officially back in session for me - I spent most of last week at HeroConf in San Diego. While the event itself was OK, the people were fantastic - in fact, one of the conversations I had there was the genesis of this very issue. In a conversation with an old friend, I made the comment that there is only 1 input your marketing team/agency/organization can’t...
about 2 months ago • 8 min read
Happy Sunday, Everyone! I hope you’re all enjoying the first weekend of (unofficial) fall! If your week was anything like mine, it was jam-packed with 2027 planning meetings, BFCM and a few last minute, we-have-a-problem-that-needs-solved-in-2026 client requests. Plus some back-to-school drama (because why not?) and the (glorious) return of football. One of those many meetings was with a senior living operator spending $180k-$200k/yr on creative production, yet wildly frustrated with ad...
about 2 months ago • 16 min read
Happy Sunday, Everyone! The (unofficial) end of summer is finally upon us: Labor Day weekend. I hope these last few months have been fun, relaxing, rejuvenating and full of wonderful memories with friends, family and loved ones. I’ve always thought of summer as the best time of the year – the warm, late sunsets, the slightly slower pace, the kids playing in the neighborhood. It’s a magical time of year. But that’s the nature of time: all seasons come and go. And while the next summer may feel...
2 months ago • 17 min read
Happy Sunday, Everyone! Over the last few weeks, I’ve been part of a half-dozen (ish) 2027 planning meetings – which is to be expected in August. The post-Labor Day mad-dash-to-year-end hasn’t kicked off, everyone’s calendars don’t look like the 405 at rush hour, budgets aren’t committed yet. One thing I’ve noticed from those meetings is there is almost always a focus on two numbers: (1) a growth target and (2) an efficiency goal. The meeting I had on Friday morning was a canonical example:...
2 months ago • 17 min read