In this edition of What Went Wrong, I got a chance to explore mistakes, missteps, and the humbling reality that even seasoned pros can land flat on their face with repeat guest Robin Waite. This time, he didn’t come with a polished pitch or a shiny success story. He brought a cautionary tale about Facebook ads, cold leads, and a £9,000 lesson in what happens when you trust the algorithm more than your instincts.

Even Experts Trip Up Robin isn’t new to marketing—he ran an agency for 12 years. But when it came to Facebook ads for his own coaching business, he got caught in the allure of automation and scale. What started strong eventually crashed, all because the warm audience he’d been nurturing for years dried up.

Your Audience Isn’t Infinite Facebook ads worked—until they didn’t. The moment his familiar, friendly audience was exhausted, the leads stopped flowing. Robin kept the campaign running for three more months, hoping it would fix itself. It didn’t. Turns out, if you don’t refill your marketing funnel, it doesn’t matter how clever your copy or shiny your creative.

Know Enough to Stay Dangerous Robin outsourced the nitty-gritty to so-called ad experts, trusting they’d fix the problem. But no one could explain what was going wrong. That blind spot cost him. The lesson? You don’t need to be the expert, but you need to know enough to ask the right questions.

When in Doubt, Go Back to What Works With his budget blown and confidence shaken, Robin went back to basics—his podcast, speaking gigs, and book. Instead of chasing cold leads, he rebuilt slowly by focusing on brand-building and trust, knowing that meaningful connections take time.

Marketing is Just One Big Science Fair Like any good experiment, sometimes things blow up. And that’s okay. Robin reminded us that failure is part of the formula—especially in marketing. The trick is not to avoid mistakes, but to make better ones next time.

Takeaways for Business Owners

• Warm audiences are wonderful—but they won’t last forever. Always be adding new people to the top of your funnel.
• Facebook ads can be powerful—but only if you understand the mechanics. Don’t hand over your entire budget without oversight.
• Track what’s working, and don’t be afraid to pivot. If your gut says something’s off, it probably is.
• When the fancy stuff fails, go back to your roots. Relationships, conversations, and trust still matter most.

And maybe most important of all: Marketing isn’t magic. It’s messy, imperfect, and beautifully human—just like us.

Robin is the founder of Fearless Business, a Business Accelerator for Coaches, Consultants and Freelancers.

Having spent 12 year’s running a digital marketing business, Robin pivoted in 2016 to focus on the part of his business he liked the best; training business owners how to be better in business. In 2016 Robin founded Fearless Business, a unique Business Growth Accelerator for Coaches, Consultants and Freelancers so help free them from the sales cycle of doom!

LEARN MORE ABOUT ROBIN

And be sure to look for Robin's new book THE FEARLESS BUSINESS OWNER'S BLUEPRINT

You know, I’ve always believed marketing should feel more like a warm hug than a high-pressure sales pitch. So when Alesia Galati and I got to chatting about social media burnout (oh yes, that nagging, energy-draining beast), it was like she reached into my cluttered content calendar and whispered, “There’s a better way.” We laughed, we nodded, and somewhere between SEO tips and podcast rants, I found myself ready to trade reels for real conversations. If you’re teetering on the edge of social media fatigue, wondering if there’s an off-ramp that doesn’t lead to oblivion—good news. There is. And Alicia’s got the roadmap.

Main Points from the Conversation:

1. Podcasting as a Stress-Free, Strategic Alternative to Social Media Alicia hit a nerve with so many of us—social media can feel like a hamster wheel with no off switch. Podcasting, by contrast, offers a calmer, more intentional way to share content, connect with your audience, and still build your brand without dancing in front of your phone.

2. Guest Appearances as Powerful SEO and Exposure Tools You don’t have to do it all yourself. By guesting on other people’s shows, you tap into new audiences who already trust the host—and just might trust you too. Bonus? Those appearances show up on Google, helping your digital footprint grow without a single trending hashtag.

3. The Magic of Names and Smart SEO Practices Don’t underestimate the power of your own name in a podcast title. Whether it’s your show or a guest spot, making your name searchable helps you get found. Retitling old episodes or refreshing descriptions is like giving your content a second wind—and Google loves it when you freshen things up.

4. Newsletter Love and Thoughtful Repurposing Alicia and I both agreed: newsletters are the unsung heroes of content marketing. Sharing new and old episodes, linking to guest features, and curating themes gives your audience a reason to stick around—and gives your podcast episodes a longer shelf life.

5. Pick Your Lane, and Stay There (Happily) You don’t need to be everywhere. Really. Pick one platform you like (mine’s LinkedIn), build a cozy corner on your website, and focus on podcasting and newsletters to draw people in. When you stop chasing the algorithm and start owning your message, marketing becomes a whole lot more enjoyable

When a Great Idea Doesn’t Get a Second Chance

This is another one of my What Went Wrong? conversations, and I love these because we all have ideas that don’t turn out the way we hoped. Sometimes, they’re just bad ideas. Other times, we give up too soon. That’s exactly what happened to Nina Froriep, who had a smart, scalable concept for video production—but abandoned it after a rough first attempt. Years later, she watched someone else build a thriving business using the same model.

What Happened

Nina came up with the idea of a video assembly—a streamlined production process where multiple business owners could shoot professional videos in a single session, saving time and costs. It seemed like a brilliant, efficient approach. She lined up her first participants, booked a location, and prepped everything. Then reality hit. Clients showed up late, skipped the pre-work, or ignored the schedules entirely. The result? Chaos. A few usable videos, a ton of frustration, and an idea that never got a second chance.

Key Takeaways from Our Conversation:

Preparation Sets the Stage for Success – Nina assumed experienced business owners would come prepared, but they didn’t. In hindsight, she realized they needed more structured guidance before the shoot, including clear deadlines and rehearsals.

Investment Creates Commitment – The low-cost nature of the offer meant clients weren’t as invested. If they had paid more—or had to complete the required pre-work—they might have taken it more seriously.

Persistence Matters – Nina scrapped the idea after one frustrating attempt, only to realize later that it could have worked with some adjustments. Success often comes from iteration, not perfection on the first try.

Timing Can Be Everything – Sometimes, an idea is solid, but the execution or the market isn’t quite ready. A little patience and a few tweaks can make all the difference.

Learn From the First Failure—Then Try Again – Instead of assuming the concept was doomed, Nina could have analyzed what went wrong, adjusted, and given it another shot. Many great ideas need a few failed attempts before they take off.

The Bottom Line: Just because something doesn’t work the first time doesn’t mean it won’t work at all. The real trick is knowing when to refine and try again versus when to walk away.

Yes, we’re talking about AI again because, let’s be honest, it’s everywhere, everyone is using it and most people are using it wrong. It’s easy to feel like you’re just throwing AI at problems without a real plan. That’s why I was excited to talk to Melissa Reeve, an expert in agile marketing, about her TRISS framework—a simple way to decide where AI can make the biggest impact in your business.

If you’ve ever caught yourself bouncing from one AI tool to another, hoping something sticks, Melissa calls that “random acts of AI.” And just like random acts of marketing, they rarely lead to success. Instead, the TRISS framework (Time, Repetition, Importance, Satisfaction, and Standardization) gives business owners a way to filter through the hype and focus on AI applications that actually save time and improve efficiency.

Here are the key takeaways from our conversation:

1. Time Matters – If a task doesn’t take much time, it’s probably not worth automating. But if something eats up hours of your week, AI might be the perfect solution. Before jumping in, do a quick cost-benefit analysis.
2. Repetition is Key – AI works best for tasks you do over and over again. Think about activities like writing social media posts or summarizing documents. The more predictable the process, the better AI can handle it.
3. Importance and Risk – Not every task is created equal. If something is high-stakes (like legal or financial summaries), you may want to keep AI in the background and add a human review step. But for low-risk tasks, AI can be a huge time-saver.
4. Satisfaction Counts – We all have those tedious tasks we dread. If something drains your energy, it’s a great candidate for automation. But if it’s a task you love and excel at, AI might not add much value.
5. Standardization Simplifies Everything – AI thrives on consistency. If your process follows a clear set of steps, it’s easier to automate. The more standardized your workflow, the better AI can support your business.

Melissa’s advice is clear: AI isn’t about jumping on the latest trend—it’s about making smart choices that help you work more efficiently. If you start by evaluating your tasks with the TRUST framework, you’ll avoid random acts of AI and focus on real improvements that free up time for what truly matters.

Want to learn more? Check out Melissa’s free five-day email course on identifying high-impact AI use cases and follow her on LinkedIn for even more insights.

Most small business owners dream of growing our small businesses into something bigger. But scaling comes with challenges—hiring, infrastructure, and managing processes without losing control.

I sat down with Anthony Franco, a serial entrepreneur who has launched, scaled, and sold multiple businesses. He’s also the host of How the Founder, a podcast where he and his co-host dive deep into the challenges business owners face. In this conversation he shares his insights on scaling the right way.

1. Ask Yourself: Do You Really Want to Scale? – Growth isn’t for everyone. Some businesses thrive at 5-10 employees, and scaling beyond that requires a different mindset and willingness to delegate.

2. Systems and Processes Are Essential – Once you decide to grow, you need to document how things are done. A business can’t scale if key processes exist only in the founder’s head.

3. Communication and Organization Matter – As teams grow, structured communication through tools like Slack, Teams, and shared knowledge bases ensures everyone stays aligned.

4. Founders Must Learn to Let Go – The biggest roadblock to scaling is often the founder. Delegation is crucial, and tasks don’t have to be done exactly how you would do them—just well enough to keep things moving.

5. Hire for Culture and Performance – Bringing in the right people is vital. Prioritizing A-players and being quick to remove underperformers keeps your business strong.

My guest today is Iris Goldfeder, founder of Gas Stove Creative. Iris and I are two out-of-sync New Yorkers who somehow ended up in Indiana, crossing paths in the small business community for years. But today, instead of swapping stories about pizza and city life, we’re talking about something every business owner faces at some point: the growing pains of change.

Iris recently had a lightbulb moment—she’d evolved her business, but she’d forgotten to tell people! So while she had moved on to working with established companies, her network was still sending her the startups she used to serve. This realization kicked off a strategic shift, one that every business owner can learn from. How do you reposition yourself without alienating past clients? How do you make sure people know what you do now? And how do you avoid pricing conversations that make you want to bang your head against the wall?

1. Communicate Changes Early & Often: Don’t assume people know your business has evolved. Proactively update referral partners, past clients, and your online audience.

2. Use Video & Social Media: A simple video post explaining your shift can go a long way in reshaping how people think of your brand.

3. Create Structured Packages: Offering clear service levels makes it easier for clients and referral sources to understand where they fit.

4. Be Confident in Your Value: If a potential client balks at your pricing, they may not be the right fit. Stick to your worth and don’t be afraid to refer out.

5. Learn From Every Experience: If you learn something, it’s not a mistake—it’s a lesson. And next time you shift, you’ll know to start the conversation sooner!

We’ve all done it—Googled ourselves or our businesses, only to find something outdated, inaccurate, or just plain wrong. And the scary part? Most people believe whatever Google tells them. If Google says you’re permanently closed (even when your business is booming), potential customers won’t bother double-checking. They’ll just move on. That’s why it’s so important to take control of what Google says about you. I sat down with Andrew Laws founder of Yeseo, to talk about how business owners can make sure Google gets it right—because if we don’t do it, who will?

So how do you do that? Andrew Suggested:

1. Google Isn't Always Right – While we rely on Google for information, even Google admits its results aren’t always accurate. This means businesses need to take control of their own online presence.

2. Claiming & Maintaining Your Google Business Profile Matters – Business owners can significantly improve how their company appears online by ensuring their Google Business Profile is up-to-date and consistent across all platforms.

3. Consistency Is Key – Small variations in how your business name, address, and phone number (NAP) appear online can confuse Google’s algorithm, making it harder for customers to find you.

4. Engagement Builds Trust – Regularly updating your profile, responding to reviews (good and bad), and keeping business details accurate helps Google and potential customers see you as a reliable business.

5. Respond to Reviews – Whether they’re glowing or grumpy, replying to reviews signals to both Google and potential customers that you’re engaged and trustworthy.
6. Download the Google Business App – It makes updating your profile easy, plus Google will prompt you to keep your information fresh.
7. Audit Your Online Presence Regularly – Don’t assume Google will always get it right. If something looks off, fix it before it costs you business.

Marketing is all about connections, but too often, we skip over the most important piece—people. Sure, we love talking about product, price, place, and promotion, but what about the humans behind the strategy? That’s why I brought back Dave Dave Charest, Director of Small Business Success at Constant Contact, for a lively chat about the Four P’s of People—peers, pros, patrons, and promoters. Spoiler: your next marketing breakthrough might come from focusing less on what you’re posting and more on who you’re talking to.

Peers Are Your Marketing Wingmen Think of your peers as your brainstorming buddies—the business owners and marketers walking the same path. Sure, they might be in your industry, but they’re not your competition. Instead, they’re allies who can share insights, lessons learned, and even a little encouragement. As Dave put it, peers can help you grow by sharing their own roadmaps to success.

Pros: Your Marketing Role Models These are the businesses that make you say, “I want to do that someday.” Dave suggested following pros for inspiration—whether it’s how they craft campaigns or how they interact with their audience. Even better, engaging with their content can lead to new connections with like-minded people. Think of pros as your north star for what’s possible.

Patrons Keep the Lights On Your customers are your patrons, the folks who not only pay the bills but also provide a goldmine of feedback. Whether you’re creating posts to entertain, educate, or answer their questions, keeping this group engaged can spark deeper loyalty. And when they engage with your content, their networks notice, bringing you closer to your next batch of clients.

Promoters Are Your Secret Weapon Promoters are the people who sing your praises, often loudly and without being asked. They may not even be customers themselves, but they believe in what you’re doing and love sharing it with their communities. Dave reminded me that it’s worth nurturing those relationships—comment on their posts, cheer them on, and show them the love they show you.

Remember, success isn’t about shouting your message into the void. It’s about listening, building relationships, and connecting with the people who matter most to your business.

Dave Charest is the Director of Small Business Success at Constant Contact, the online marketing leader trusted by millions of small businesses. In his role, Dave acts as an educator and an advocate for small business leaders, marketing professionals, and nonprofits by providing practical marketing advice to help them achieve their goals.

He is a dynamic leader, speaker, creator, and award-winning marketer who strives to inspire small businesses by simplifying the complex world of online marketing. Dave also hosts the Be a Marketer podcast, a 2024 Webby Awards Honoree.