I want to talk about upselling, and when it actually works against you.

Most smart companies have a core product and a menu of add-ons. The really smart ones know not to throw every extra at a customer the minute they say yes. You listen first. You find out what they need. Then you decide which add-ons make sense.

The other day, I stopped at Hardee's and ordered a hamburger. No cheese. What followed felt like an interrogation.

Did I want a combo? A drink? A pastry? Was it a number one? A number seven? Meanwhile, I kept repeating the same thing: "I just want a hamburger." By the end of the conversation, I wasn't hungry. I was annoyed.

And that got me thinking. Are you doing the same thing to your customers? Are you so focused on selling the extras that you stop listening to what they actually came to buy?

Don't get me wrong. Add-ons are a great way to increase revenue. But only when they're relevant. Offering everything to everyone isn't a sales strategy. It's the business equivalent of that drive-thru speaker that won't stop talking.

Before you pitch the upgrade, ask yourself a few questions.

• Does this solve a problem the customer has already mentioned?
• Have I explained why this add-on matters?
• Am I offering it at the right point in the conversation?

And here's one more thing to consider. Are customers asking for services or features you don't currently offer? Sometimes the biggest opportunity isn't another upsell. It's paying attention to what people are trying to buy.

The goal isn't to sell more stuff. The goal is to help customers get more value

Ever feel like your marketing plan is the rope in a tug-of-war match?

The sales team is pulling one way. The owner is pulling another. Someone's daughter took a marketing class in college and has opinions. And the person who's actually responsible for the campaign is standing in the middle, trying not to get dragged through the mud.

That's why my conversation with Beth Trejo really struck a chord with me.

Beth is the CEO and co-founder of Chatterkick, and she works with franchise organizations, multi-location businesses, and other companies where marketing decisions rarely come from just one person. While her examples came from large organizations, I couldn't help thinking about all the small businesses I've worked with over the years. Sometimes a "multi-layer brand" is just a family business with three generations around the conference table.

A few things stood out from our conversation:

• Marketing isn't just about customers. Sometimes you need to market your ideas internally. Beth pointed out that marketers spend a lot of time building buy-in inside the organization. If stakeholders don't feel included, they'll grab the rope and start pulling in their own direction.
• Not everyone has to participate the same way. Some people love being front and center. Others would rather hide behind the camera. Beth's advice was simple: meet people where they are and help them contribute in ways that feel natural.
• Stop arguing and start testing. This might have been my favorite part of the conversation because it brought back memories of my corporate days. When someone insisted my idea would never work, I'd ask for a small test. Data has a wonderful way of settling arguments without bruising anyone's ego.
• Local voices make brands stronger and easier to find. For franchise and multi-location businesses, there needs to be consistency. But there also needs to be room for local personality. That's good for customer relationships and good for SEO. Search engines, just like customers, want signals that you're connected to the community you serve.
• Remember that you are not the customer. This sounds obvious, but it's amazing how often we forget it. The things we like, dislike, click on, or ignore may have nothing to do with what our customers want. The strongest marketing teams stay curious and let customer behavior guide the decisions.

Ultimately, it isn't about winningt the game of tug-of-war, it is about .getting everyone to pull in the same direction, the customer's direction!

I’ve watched a lot of entrepreneurs build amazing communities, only to discover that applause doesn’t always pay the bills. In this conversation with , we talked about the moment she realized her thriving podcast community needed more than goodwill and good vibes to become a sustainable business.

Angel has always been brilliant at bringing people together. Her podcast networking platform created real relationships, real collaborations, and real opportunities. But somewhere along the way, she realized she was creating enormous value without building a business model around it.

That’s a lesson a lot of women business owners know all too well.

What made this conversation especially interesting was how intentionally she shifted from “free for everyone” to a tiered community with clear value, stronger positioning, and protected intellectual property.

• Free can open the door, but it shouldn’t be the whole house. Angel discovered that even a small monthly fee changes the quality of participation. The people willing to invest, even modestly, are usually the ones serious about growth.

• Your intellectual property has value. Treat it that way. One of my favorite moments in the conversation was our discussion about trademarks, ownership, and protecting the assets you create. Too many business owners build incredible frameworks and never stop to realize they actually own something valuable.

• Visibility works best as an ecosystem. Angel shared her “Apples” framework for building visibility through articles, podcasts, press, live events, and evergreen content. I loved this because it’s a reminder that marketing rarely works as a one-and-done tactic. The magic happens when all the pieces support each other.

• Start messy. Just start. We also laughed about early podcast recordings that sounded like they were captured inside a tile bathroom. But the point was important. Waiting for perfect usually means never starting at all.

This episode is a great reminder that building a business takes more than creating value. You also need structure, intention, and the confidence to ask people to invest in what you’ve built.

Because “free forever” is not a marketing plan. It’s a hobby.