Engagement Doesn't Pay the Bills: A Conversation with Wendy Jacobson

Everyone is creating content. Every founder is posting on LinkedIn, every company has a blog, every marketer has an AI tool. And somehow trust feels harder to earn than ever.

That's exactly why I wanted Wendy Jacobson on the show. For nearly two decades she's run Incredible Content, helping B2B companies, entrepreneurs, and professional service firms turn what they actually know into content people care about. Not through hacks or viral gimmicks, but through credible, consistent stories. Because at the end of the day, content isn't really about content. It's about whether people believe you.

Going viral is not the goal

Wendy has actually gone viral, so she can speak from the other side of it. A post about a road trip with her father did around 7 million views on LinkedIn, 70,000 reactions, 3,500 comments, and hundreds of messages. She got featured in LinkedIn News. The dopamine was constant, and it was genuinely fun.

And then she counted the cost. It was a ton of work to capitalize on, she picked up a couple of short-term clients who weren't her target audience, and she was left asking whether it was the best use of her time. Her verdict: going viral hits a wave of people who don't know you, don't care who you are, and will never buy what you offer. Two or three reactions from people in your actual target audience can be worth more than 2,000 from strangers, because engagement doesn't pay the bills. Qualified prospects who become clients do. One eyeball that will buy beats a thousand that scroll past.

Content is a slow burn

If content is so clearly valuable, why do most companies still treat it as an afterthought? Wendy's answer is that it's brutally hard to measure, and we live in an immediate-gratification world. Content is a slow burn. A drip, drip, drip. You meet people where they are, usually long before they're ready, sometimes before they even know they need you, and they zigzag through a buying journey for weeks, months, or years before they act.

Her proof is a phone call she got the week before we spoke. A woman she'd never heard of, who had attended one of Wendy's webinars a year earlier, joined her email list, quietly read her emails for a year, and finally picked up the phone to talk about working together. Wendy had no idea she existed, but the drip had been reaching her the whole time. Those stories happen every day, and none of them show up cleanly in a return-on-investment dashboard. That measurement gap is exactly why content gets deprioritized, and exactly why the companies that stick with it win.

AI made content easy, and identical

Content has never been easier to produce. Feed a writer you admire into your favorite LLM and it'll spit out something in that voice. Wendy's caution is that credibility and authenticity are the two pieces that machine can't fake. Train it however you like, it's still grabbing from the same source material as everyone else, so if all your competitors are using the same tools, you're all going to sound the same.

She likens AI content to the keyword-stuffed blogs of ten years ago. Everyone knew it was a game, everyone did it to get found, and it did nothing to help you stand out. AI-generated content is the same move in a new outfit. She's not anti-AI, and she thinks it's great for a first draft. Her one hard rule is not to publish that draft into the world as your finished thinking. With this much content flooding every feed, the only way to stop the scroll is to add your own stories, your own perspective, your own opinions, the things an LLM cannot pull from the internet because they only exist in you.

Start with why

The biggest change in Wendy's business over 18 years is the question she leads with. Back then, if a client said "we need a blog," she'd say "great, let's write a blog." Today she says "let's take a step back. Why do you need a blog? Because it's Monday and you haven't published in two weeks? That's the wrong answer."

The job now is helping clients connect content to an actual business goal: what do you want the audience to do, and how does that action help you hit your objectives. Not posting for the sake of posting, but posting with a purpose. As she pointed out, the answers are often revealing, because a lot of people genuinely don't know why beyond "everyone else is doing it." Which, she'd gently ask, is that really the best reason.

The case study everyone gets wrong

Wendy is obsessed with case studies, and she got that way by reading a lot of bad ones. Most of what companies publish as case studies are really project overviews, or a business beating its own chest about how great it is.

A real case study, in her definition, is a story told from the client's perspective. Company X isn't narrating Company Y's story. Company Y is telling their own: their pain points, why they went looking for a solution, what Company X did, and the results they're now living. The hero isn't the company. The hero is the client. That flip is what makes it work, because it's relatable to other buyers in the same position and far more credible. It's not you telling people how awesome you are. It's your client telling them. As for getting a reluctant customer to say yes, she plants the seed early: mention during the proposal that if this goes well, you may ask for a case study. Some people even write it into the contract. And if the client won't use their name, "a regional financial services provider" still carries enough clout to tell the story.

The reps, and knowing when to zig

Fractional and solo work is having a moment, so I asked what she's learned that takes most people years. Her answer was refreshingly unglamorous: it's not a quick-win thing. You have to do the reps. You'll have bad days, you'll hit burnout, and you have to actually manage your mental health, notice the signs, and give yourself permission to close the laptop and go take a walk. It's also lonely, especially now, with everyone flexing on LinkedIn. Her guardrail there is simple: don't compare yourself to others, because everyone shares the good stuff and very few people share the bad.

She also preaches listening to the market, and she's lived it. She once built an online magazine, Minneapolis Happening, up to nearly 40,000 monthly readers, and shelved it because the ad-based revenue model was never going to feed her kids. The market was telling her something, and she listened. That non-linear path, media, PR, sales, is a feature, not a bug. Boxing yourself into one idea of who you are, she says, is confining and leaves no room to grow. She got into real estate in the first place because she saw a realtor's name on a bus bench and thought, my name could be on a bus bench too. Opportunities show up in strange places if you stay open to them.

What makes a great writer

Since Wendy helps people find their voice for a living, I asked what makes a great writer. Someone who doesn't censor themselves, she said. Someone who lets what they feel onto the page. You're writing for an audience, but you're also writing for yourself.

She worries that writing is an art getting quietly squashed by AI, and she thinks everyone should learn it anyway, whether they enjoy it or not. Her own love of it goes back to a fifth-grade neighborhood newsletter called Paperclip, which was, fittingly, stapled. The written word, done with real feeling, can move people to act. No LLM in the room. Just a person deciding to say the true thing, and saying it well.

Key takeaways

A few things worth holding onto.

Judge content by the right eyeballs. Two or three reactions from your target audience beat thousands from strangers. Engagement is not revenue.

Content compounds slowly. It's a drip, and the buyer's journey is long and non-linear. Companies quit right before it works because the payoff is hard to measure.

AI makes everyone sound the same. The differentiator is the stuff a model can't source from the internet: your stories, your perspective, your opinions.

Ask why before you create. Content tied to a real business goal beats content posted because it's Monday.

Make the client the hero. The most credible case study is your customer telling their own story, not you praising yourself.

Frameworks worth stealing

The one-eyeball test

Stop grading content on likes and comments. Ask instead: did this reach anyone in my actual target audience? Two or three of the right people beat two thousand of the wrong ones, because one eyeball that will eventually buy is worth more than a thousand that scroll past. Vanity metrics feel good and don't pay the bills.

Start with why

Before writing the blog, the post, or the email, answer why. What business goal does it serve, what do you want the reader to do, and how does that action move you toward your objectives? "Because everyone else is doing it" and "because we haven't posted in two weeks" are the wrong answers. Post with a purpose or don't post.

The client-as-hero case study

Write the case study from your customer's point of view, not your own. They narrate their pain, why they went looking, what you did, and the results. You're the sponsor, they're the star. It reads as credible because it's them praising you instead of you praising you. Plant the seed early, ideally at proposal stage, so the ask is never a surprise.

Do the reps

An independent business is not a quick win. Keep showing up, protect your mental and emotional health, step away when you need to, and never measure your behind-the-scenes against everyone else's highlight reel.

Quotes worth keeping

The lines I wrote down.

Engagement doesn't pay the bills. Qualified prospects who become clients pay the bills.

Content is a slow burn. It's a drip, drip, drip.

If all your competitors are using the same tools, everyone's going to sound the same.

The hero isn't the company. The hero is the company's client.

And the one that reframes every testimonial you'll ever write.

It's not me telling you how awesome I am. It's my client telling you how awesome I am.

Rapid fire round

Same questions every guest. No prep, no warning. Here's how Wendy handled it.

Best advice you've ever received? Don't go to law school. From her dad, who was an attorney.

Advice you wish you'd listened to? Go to journalism school. Also from her father. She said nope at the time.

What would you tell your younger self? Don't color your hair. Everyone will love it.

Ongoing challenge that keeps you up at night? Honestly, time management. She's the first to admit she's awful at it and wishes she were better.

Favorite spot? The Minneapolis food scene, which surprises people. Ama Sushi, an Argentine pizza place called Beludo, and a genuinely hot craft-brewery and taproom scene.

Tool you can't live without? Wordle, and now Strands too. She can't start her day without it, and she wanted to give an answer nobody else would.

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Wendy Jacobson is the founder of Incredible Content, where she's spent 18 years helping B2B companies and professional service firms turn expertise into content that builds credibility. Find her on LinkedIn.