I love the What Went Wrong conversations because they remind me that even when things look like they’re working, there’s usually a crack or two hiding under the surface.

In this episode, we dig into one of those uncomfortable moments every business owner faces. Growth slows, the numbers get fuzzy, and suddenly the team you built so carefully starts to feel… expensive.

I sat down with Matt Levenhagen, founder of Unified Web Design and host of the Builder Podcast, to talk about what happens when you hold on just a little too long.

Here’s what really stuck with me:

• Hope is not a hiring strategy Matt kept his team based on where revenue had been, not where it actually was. When projects stalled, he filled time with “busy work” instead of facing the numbers. That gap between reality and optimism gets expensive fast.

• The warning signs are usually obvious, we just ignore them Delayed projects, slow client responses, and scrambling to keep people busy. Those were all signals. The lesson? If you’re getting creative just to justify payroll, it’s time to pause and reassess.

• Flexibility beats the “perfect team” Matt realized he didn’t need a full bench all the time. Now he’s building a more flexible structure with a mix of core team members tied to revenue and others brought in as needed. It’s not about loyalty, it’s about sustainability.

• Invest in sales before you need it This one hit home. When things were good, he didn’t push marketing or sales hard enough. By the time revenue slowed, it was too late to quickly replace that pipeline.

Yes, you want to invest in growth. But when the business shifts, you have to shift with it. Because holding on too long doesn’t just cost money. It costs momentum.

When I moved from Texas to Indiana one of the things I loved best was the color of the seasons. Spring brings bright pastels which morph into the rich greens of summer. Then comes fall with the bring oranges, yellows and a few shades of brown.

The only exception is winter filled with dreary colorless days which seem bland bland when compared to the vibrancy of colors throughout the rest of the year. I think that is why I appreciate evergreen trees and the bright spot of colors they bring all year long. Just as these wonderful trees bring consistent color to my yard, evergreen content brings spots of color to a marketing calendar.

What is Evergreen Content?

Evergreen content, unlike seasonal content or breaking news, this information is always relevant to your readers.

Frequently asked questions, simple how-to blog posts, or product reviews make great evergreen content. These posts can be researched and written well in advance and be ready whenever you need some fresh content

Start with the questions customers ask

Look in your email folder for those long answers you have already written. This is a great starting point for a blog post. If one customer has the question, others will as well. And these posts tend to index well on Google, as prospective customers search for answers.

Include Key Words

Brainstorm a list of keywords you want to rank for. Use a keyword tool such as Google Trends or Google Search Console to find alternatives and ideas.

Look for niche words and phrases. which will have a better shot at rising to the top because there will be less competition

Quality over Quantity

If you want your post to stand the test of time, you can’t just slap up a 500 word article and call it a day. If you do, another article will come along pretty quickly and knock you down.

Take extra time when you write evergreen content. Research the topic, add unique examples, and your perspective. Create an article which isn’t just another “5 Ways to Do This….”.

Update Your Evergreen Content

I know, I said this would be the kind of blog post that would stand the test of time, it wouldn’t age and it would live on forever.

All of that is true, but if it is a great traffic draw for your website, go back occasionally and add new content, a different image, and maybe a new CTA to keep it fresh.

Sometimes the best way to explain marketing is with a good story.

In this episode, I chatted with Ryan Ross, head of marketing at BrokersBloc and author of the novel Benefits with Friends. The book follows a very unlikely hero, Al Dente, a pasta manufacturer who suddenly inherits his father’s benefits brokerage. As Al tries to figure out how to grow the business, he learns some very real marketing lessons along the way.

Ryan wrapped those lessons in humor, food puns, and a cast of memorable characters, but the marketing advice is solid and surprisingly practical.

Here are a few ideas that really stuck with me.

• Pick a niche before you pick a tactic Al starts with nearly a hundred clients but no clear direction. His mentor pushes him to choose a specific audience instead of trying to serve everyone. Because of his background, he understands manufacturing. Once he focuses there, everything else becomes easier. The message is clearer, the prospects make sense, and the marketing finally has direction.

• Borrow credibility while you build it Al is still learning the benefits business, so he builds authority by creating content and connecting with experts. Speaking at industry events, hosting conversations, and sharing what he learns helps him build visibility faster than waiting until he feels like an expert. Teaching and learning at the same time can be a powerful combination.

• Turn education into a marketing tool One of the smartest strategies Ryan shared was creating continuing education content for licensed professionals. If your audience needs CE credits to keep their license, offering approved educational sessions can dramatically increase participation. Even better, those sessions position you as a trusted resource while you help your audience solve a real problem.

At the heart of Ryan’s story is a simple reminder. Marketing works best when you know who you want to help, show up where they gather, and share something useful.

Turns out the recipe for good marketing is not that different from good pasta. Start with the right ingredients and keep it simple.

About Ryan

Ryan Ross has is head of marketing at BrokersBloc, a GA for independent benefits brokers. He is the author of Benefits with Friends, a fictional book about a benefits broker, Al Dente, as he navigates reviving his father's benefits brokerage. Ryan spent 10 years in marketing and sales at Dow Jones, the Financial Times, and BrightTALK. He has completed 3 Ironman triathlons.

Pre-order the book

This week thousands of podcasters around the world take part in Podcastathon, a global effort that shines a spotlight on nonprofit organizations doing meaningful work in their communities. For one week, hosts swap their usual topics for stories about causes they care about and invite their listeners to learn more, get involved, or lend support.

This episode is my contribution to that global event, and it gave me the perfect excuse to talk about one of my favorite nonprofits.

Sometimes the hardest part of marketing isn’t getting attention. It’s helping people feel comfortable enough to try something new. That is exactly the challenge when you run a Fringe theater festival.

In this episode, I chatted with Paul Daly, Executive Director of the IF Theatre in Indianapolis. IF Theatre is the home of the Indy Fringe Festival, one of the largest fringe festivals in the world, bringing dozens of performers and hundreds of shows to Mass Ave every summer.

The festival celebrates creativity, experimentation, and the kind of performances you will not see anywhere else. But that same freedom can make newcomers hesitate. When audiences are not quite sure what they are getting into, they may stay home.

Paul shared a simple marketing approach designed to make the experience easier to say yes to.

Takeaways

Give people a path into the experience Fringe festivals can feel overwhelming. With so many shows and styles, first timers do not always know where to start. This year IF Theatre plans to introduce curated show lists. Want a day of comedy? There is a list for that. Prefer serious drama or an eclectic mix? There are paths for those too. Instead of asking people to sort through dozens of options, the festival gives them a starting point.

• Help people understand what to expect Younger audiences especially want clarity before they commit. What will this experience feel like? Is it funny, thought provoking, weird, or a little bit of everything? Clear descriptions and curated experiences remove uncertainty and make it easier for someone to buy that first ticket.

• Tell the bigger story behind the brand Many people know Indy Fringe as a ten day festival. What they may not know is that IF Theatre runs year round programs, classes, and performances. One key message they continue to repeat is simple. IF Theatre is the organization. Indy Fringe is its biggest event.

The lesson here is straightforward. When people feel unsure, they hesitate. When you guide them, they step forward.

And sometimes all it takes is showing them where to start.

We all love a good story. But here is the twist. If you are the hero, you are doing it wrong.

In this conversation, I chatted with John Elbing, creator of the Story Building Method and author of a new book on the topic. We dug into the difference between storytelling and story building. It is not a play on words. It is a shift in perspective that can change how your marketing connects.

John believes storytelling has turned into a coat of paint. Hooks. Tricks. Presentation tips. All fine. But before you polish the story, you need to decide which story you are telling.

And here is the big idea. It is not your story. It is your customer’s.

A few takeaways you can use right away:

• Recognition comes first Before someone cares what you do, they need to see themselves in your message. In your words. In your images. In the problems you describe. When they think, “That’s me,” you have their attention. Skip this step and they scroll right past you.

• Perception shapes your value People want to quickly understand what you do and where you fit. If they cannot put you in a category, they get confused. And confused people do nothing. Be clear about what makes you different and why that difference matters.

• Projection closes the gap Help them imagine life after they work with you. What changes? What feels easier? What problem goes away? When they can picture that future, they are already moving toward a yes.

One of my favorite examples John shared was about lawn care. You can say, “I mow lawns.” Or you can talk about the exhausted homeowner who wants to feel proud of her yard again. Same service. Completely different story.

That is the shift.

When you build your story around your customer’s aspirations, struggles, and trigger moments, your marketing feels less like a pitch and more like a conversation.

And that is when people lean in.

If your message is not landing, maybe it is time to stop being the hero and start being the guide.

I am going to be honest right from the start. This is a rant. A friendly one. But still a rant.

I’m a geek at heart. I love shiny tools, clever plugins, little bits of tech that make my marketing life easier. But lately it feels like some of my favorites have decided to test me. Really test me.

It started with my email marketing platform quietly turning off a third-party API I relied on. Their decision, fine. But maybe a heads up would have been nice. Instead, I spent four months wondering why new subscribers were suspiciously quiet. Turns out, the connection was dead. And I only discovered it while building a completely unrelated page on my website. When I reached out to support, they casually mentioned they don’t use that interface anymore. Terrific.

Then my chatbot decided to hallucinate. I asked it to summarize an interview and create a teaser. Simple request. Except it thanked a guest who wasn’t even in the conversation. Not even close. I have no idea where it found that name. Apparently, creativity is a little too free these days.

And just when I thought I had hit my quota for weird tech behavior, the tool I use to make reels took a detour. This is the tool I trust to pull clean little snippets and generate accurate captions. Instead, it rewrote my perfectly articulate guest into something that sounded like bro speak. She deserved better. I deserved better. The whole episode deserved better.

So yes, this is a rant. But it is also a reminder. No matter how good a tool is, no matter how long you have trusted it, you still need to double check. Tools change without warning. Interfaces break. Technology goes off the rails. And if you are not paying attention, your marketing can end up in a ditch you did not see coming.

Takeaways

• Check your tools regularly. Even the ones you think are rock solid. A quick test can save months of missing data or embarrassing surprises. • Never hand over your voice completely. AI is helpful, but it is not infallible. Review everything before it goes into the world with your name on it.

Because in marketing, the only thing worse than tech that fails is not noticing it failed.

More than a Few Words - Marketing Conversation

A bite-sized marketing podcast that cuts through the noise and delivers actionable ideas, with no fluff and no jargon.

If smarter marketing really worked the way the tools promise, we would all be done by lunch. Instead, most days feel like standing in the cereal aisle staring at fifty boxes that all swear they are the healthiest choice.

That is why I sat down with Lisa Raehsler to talk about what to skip when everyone is promising smarter marketing. Lisa is a PPC strategist with more than twenty years in the trenches and the founder of Big Click Co. She spends her days helping businesses sort out what actually works from what just looks shiny.

Paid ads are not plug and play. Between Google, Meta, LinkedIn, Pinterest, and the parade of AI tools promising instant results, it is easy to feel behind before you even start. Lisa reminded me that the problem is not a lack of tools. It is too many tools pretending they know your business better than you do.

• Skip the “easy button” marketing. Every platform now offers a button that says “generate headlines” or “create images.” Lisa’s advice was simple. Use those ideas as a starting point, then step away. The platforms do not know your goals, your customers, or what makes you different. If you use what they hand you, you will look like everyone else.

• Start with your basics, not the platform. Before worrying about ad sizes or image specs, get clear on what you are selling, who it is for, and why it matters. Once that foundation is solid, you can adapt the message to fit how people behave on each platform without losing your brand voice.

• Real beats perfect every time. AI images and stock photos can feel polished, but they often trigger that subtle “something is off” reaction. Lisa shared that real photos from your business, even lightly enhanced, build more trust than flawless AI faces that look like they belong on a romance novel cover