The Content Cup Newsletter

Hi, Friend! It honestly feels like yesterday. I was dressed in a suit, holding a portfolio full of printed resumes, walking through a large ballroom at Bowling Green State University, going table to table, and introducing myself to potential employers. Throwback photo to 2016 & our MBA cohort reunion at BG! There’s no way around it…I was uncomfortable. At the time, I had a mentor named Wilbur. Yes, that was actually his first name. He had built a successful career in banking and genuinely...

Hey, friend, Last week wrapped up my very first 6-week group coaching program: How to Win on LinkedIn. And the conversation around getting clients continues to stand out to me, even as I write this now. One of the women in the program is a fractional marketing leader. Extremely smart. Experienced. More than capable of helping companies. But she admitted something I think a LOT of people consistently struggle with on the platform. That she had been spending hours creating content....

Hello, my friend, How are things going? Does it feel like you wish you had more consistency when it comes to generating leads for your business? I find that’s the case for about 99% of those I talk to. But you know what I’m finding? The fractional leaders and consultants I typically work with don’t actually have a lead problem (even though it can feel like they do). What they really have is a visibility gap inside their own network. And maybe this is really your issue as well. Because I’m...

“I hate most of the posts I read on LinkedIn.” That’s what a full-time sales director said to me recently in a DM exchange on LinkedIn. She explained that what frustrates her most is the gap between what people post and how they actually show up in real life. And honestly? I sat there thinking…you know what…I can see her point. And unfortunately…I think that’s what turns a lot of people off in building a personal brand. There’s a group of professionals I know who are experienced and...

One of my clients said something this week that I think many struggle with, Reader. In her email, she said, “One of our challenges is that we’re not great at highlighting our accomplishments or strengths — the 'inability to brag' problem.” Have you felt this, too? Or maybe you’ve hesitated to talk about what you do because it feels a little cringe. This client is a cofounder of a healthcare company with an engineering background. Talking about what she does, or even the company’s successes,...

Hi, Reader, So, in complete transparency, I had a different newsletter planned for this week… But after digging into a recent report from LinkedIn’s AI and product engineering team, I couldn’t hold off. Because it confirmed what many of us have been feeling, and you can read the entire report for yourself if you're up for it. But in the interest of time, I'll break it down for you... The LinkedIn feed is getting smarter and more unpredictable for those of us who have been on it for years....

Hi, Reader, When people ask me how to grow on LinkedIn, they usually expect to hear about strategy, consistency, and planning. And yes…don't get me wrong...those things matter. But recently, I looked back at my analytics over the past 90 days and noticed something interesting. Two of my top three posts weren’t planned at all. They were what I’d call in-the-moment posts. Real moments. Real thoughts. No content calendar involved. And honestly? That’s exactly why they worked. The Saturday...

Hi, Reader, First, I want to welcome the new subscribers who joined after I spoke to nearly 100 founders at Innovate New Albany last week. I’m really glad you’re here! Hitting the 700+ subscriber mark with this newsletter feels pretty special, so thank you for choosing to spend a few minutes here with me every other week. At the event, we had a really thoughtful conversation about how to win on LinkedIn in 2026. And when I say win, I mean grow. Grow your business by attracting new clients....

It's been brought to my attention that my readers are trying to share my newsletter, but can't find the subscribe link to send to their friends. Oops! So please, share away. (And thank you!) Sign up for free here. Hey, Reader, A founder asked me this in the DMs recently… “How do I DM people on LinkedIn without feeling salesy?” And if you’ve ever hesitated before hitting send…you’re not alone. Many of us can relate. Isn’t this the fear? Sounding pushy and transactional... Sounding like THAT...