My guest, Steven Lewis, broke one my big rules. It is ok, to make mistakes, you just don't want to make the same mistake twice. And he did.

Yep, Steven started not one, but two businesses that were—how shall I say this?—a bit too far ahead of their time. And in this candid chat, we unpack what he learned, how it shaped the work he does today, and what you, as a business owner, can take away without having to make the same mistakes.

Timing is Everything (But Not Everything) Steven launched a web business in 1994 and a social media agency in 2004—both solid ideas, just way too early. He found himself selling websites before people knew what the internet was, and social media services before anyone knew what a tweet was. The market wasn't ready, and he learned the hard way that even the best ideas need the right audience at the right time.

Sell the Symptom, Not the Cure Like a podiatrist treating knee pain, Steven learned that people don’t buy solutions to problems they don’t know they have. If your audience thinks they have a sore knee, don’t talk about fixing their feet. Speak to the symptoms they’re experiencing, not the root cause you see. Then gently guide them to the solution.

Your Cool Idea Isn’t Enough Steven built those early businesses around what he thought was cool—websites, podcasting, blogging—but he wasn’t solving a problem his audience recognized. Today, he’s flipped the script and focuses first on his audience’s pain points. It’s not about what you can do—it’s about what your audience needs right now.

Use Tools That Think Like You—Or Smarter Now Steven helps clients build their own AI-powered CMO, trained on their business to give them advice they can actually use. Essentially, he created the strategic brain he wished he had back then—and now he shares it with others.

Have you ever had that one brilliant idea—the one you were sure would be a game-changer—only to watch it sputter out despite all your careful planning? Oh, friend, you’re not alone.

I sat down with Whitney Bateson, a passionate entrepreneur who helps wellness professionals build their online credibility. But this time, we weren’t talking about wins, we were unpacking a launch that landed with a thud. Whitney shared the story of her well-intentioned (and very elaborate) launch strategy that missed the mark. And just like that favorite casserole recipe that looked amazing on Pinterest but turned into a burnt mess—there were lessons everywhere.

So pull up a chair and let’s dive into the real, raw, and ridiculously relatable side of launching, failing, and getting back up.

Key Takeaways:

Keep It Simple Whitney’s biggest lesson? Simplicity wins. She over-engineered her launch with a multi-day video series that drained her energy and diluted her message. The complexity confused her audience and fractured their attention.

Don’t Lose Sight of the Goal In trying to “warm up” her audience, Whitney accidentally shifted her focus from conversion to education. The result? A lot of content, but few clients. She learned the hard way not to let interim steps distract from the end game.

Be Present, Not Perfect Whitney was so consumed with building funnels, scripting videos, and creating new assets that she lost the bandwidth to show up authentically during her launch. She wasn’t fully present—and that absence showed.

All Leads Aren’t Equal Offering free value is great—but it doesn’t always lead to paid conversions. A freebie-seeking audience may not convert unless you intentionally cultivate a buying relationship from the beginning.

Failures Are Fertile Ground Whitney’s failed launch wasn’t the end of the story. It was a field trip into what doesn’t work—and a reminder that everything you build (even the flops) can be repurposed or refined.

Whitney is a dietitian first—but also a passionate advocate for design and technology. Throughout her career, she has seen time and again the transformative power of good design. A strong message, service, or training can fall flat if it’s not visually compelling or user-friendly. Whitney believes those details matter deeply—and she’s built her business around helping others bring their work to life through thoughtful, intentional design.

Driven by a belief that the right message, delivered at the right time, in the right way, can empower people to live healthier, fuller lives, Whitney works to bridge the gap between nutrition expertise and effective communication. She sees untapped potential in how nutrition and health professionals engage with their audiences and is passionate about helping them truly connect, demonstrate their value, and create meaningful change.

Her goal is simple: to help health professionals show up in the best light, so they can reach the people who need them most.

“Yes, the world feels like a hot mess right now. But what if the real power lies not in fixing the chaos ‘out there,’ but in finding our footing ‘in here’?”

That was the heart of my recent conversation on More Than a Few Words with the always wise and wonderfully grounded Deborah Sunderland. We didn’t talk strategy or spreadsheets this time—we talked soul. How we, as women business owners, can navigate the storms of our external world by coming back to the steady center within ourselves.

Because let’s be honest: things are weird out there. Between the economy, politics, and everything in between, it’s easy to feel like we’re being tossed around in a storm we didn’t sign up for. But as Deborah gently reminded me—and now, I’ll remind you—we’ve been through a lot, and we’re still standing. That resilience? It’s no small thing.

Key Takeaways for Women Business Owners:

You’ve already weathered storms. Recognize your resilience. The past few years have tested everyone, and you’ve made it through. That alone deserves a moment of appreciation.

Your mindset is your power tool. Our brains are sneaky little things—they’ll default to fear and scarcity unless we redirect them. When you catch yourself spiraling, pause and ask: “What thought is driving this feeling?” and then: “How might this actually be for me?”

Emotions aren’t the enemy—resistance is. Don’t stuff it down. Feel it fully. Most emotions pass in 90 seconds if we stop wrestling with them. Anger, fear, frustration—they're signals, not stop signs.

Shift the conversation with yourself. The most important conversations aren’t in the boardroom—they're in your own mind. Be kinder, more curious, and less judgmental toward yourself. And hey, extend that grace to others too (yes, even the annoying customer service rep).

Your breath is free medicine. Use it. Three deep breaths can shift your entire nervous system. It’s not woo—it’s biology. Take those moments of calm and reclaim your focus.

Try This Today:

• Grab a notebook and write down: “How am I OK right now?” List at least 5 things. (Yes, “I’m breathing” counts!)
• Close your eyes and take 3 slow, deep breaths. Let your body know: “I am safe right now.”
• Before reacting to someone, ask: “How might they be doing their best?” It’ll change the tone—and the outcome—of your conversation.

About Debra

Debra’s genius is creating a clear vision for CEO’s and their teams – making that vision a reality. With decades of C-level executive and team coaching, Debra challenges leaders by inviting them to create a collaborative, vibrant, responsible, and joy-filled culture, which fosters highly desirable results. Her practice is shared in a diverse range of industries: hi-tech, wealth management, engineering, healthcare, marketing and more.

Debra specializes in awakening leaders to transformatively solve their upper limiting beliefs, sabotaging behaviors, and unconscious biases, moving them into sustainable excellence and self-awareness. She coaches through the tough and uncomfortable work of removing the blockages preventing leaders from fully living their genius, equipping them with the thoughts and skills to bring their goals to fruition. She challenges leaders to own their results in all areas of life, to be present in the here and now, stepping out of leading with reactivity and into conscious leadership. The CEO’s chief purpose is to raise up their teams to practice radical responsibility and curiosity. Organizations achieve their optimal outcomes when they shift out of drama and create win-for-all solutions.

Debra graduated from Miami University, holds a degree in Psychology and is certified in The 15 Commitments of Conscious Leadership, the Integrative9 Enneagram, Corporate Goal Coaching, and CTI Co-Active training. Debra’s work has been featured on Fox National/Local News, Crain’s Chicago Business, the Chicago Tribune, Chicago Sun- Times, and 190 N Television. As a continual learner, Debra is a graduate of the Inner MBA – Mindful NYU program. Her base is Nashville and Chicago.

Andrew Laws has back in my guest chair (if you missed our first conversation, find it here) it, you’ll find the link in the show notes). This time we shifted away from SEO tips and took a different route—down a bumpy road lined with good intentions, disastrous mistakes, and a hacker with way too much free time.

Andrew’s story is packed with humor, hard-earned lessons, and a healthy reminder that if a business idea sounds too easy, it probably isn't really

Andrew thought starting a web hosting company would be a simple, hands-off business. Instead, he discovered that businesses built on the idea of “set it and forget it” rarely turn out to be easy—or hands-off.

The Danger of Blurring Business Boundaries: Hosting friends’ and acquaintances’ websites felt natural at first, but quickly became overwhelming. When you don’t set clear expectations with clients, small favors snowball into major responsibilities.

When Things Go Really, Really Wrong: A hacker infiltrated Andrew’s server, and when Andrew instinctively shut the server down, it triggered a full-blown meltdown. What followed was a two-year criminal investigation and a front-row seat to the importance of cybersecurity.

The Impact of Reputation Damage: Even though the hack wasn’t his fault, Andrew’s relationships with clients suffered. He learned that when you run a business, you’re not just managing services—you’re managing trust.

Life Lessons Beyond Business: After everything collapsed, Andrew realized he didn’t want a business that consumed his entire life. The experience shaped how he approaches work and parenthood today, favoring businesses that align with the life he actually wants to live.

Andrew’s story is a master class in why there are no shortcuts in business. If it sounds too easy, it probably hides a pile of trouble just waiting to unravel.

Set clear expectations with clients early and often, especially about what you will—and won't—support.

Understand the real risks behind your business model, and protect not just your income, but your reputation.

Most of all, build a business that supports your life, not one that devours it.

If you've been around here for a while, you already know—I’m an email marketing geek. Not the kind of geek who builds robots in her basement, but the kind who gets excited about subject lines and open rates the way some folks get excited about the first tulips of the season. That’s why chatting with Ellen McDowell Strauss felt like talking to an old friend who also happens to alphabetize her spice rack. Ellen and I first connected over our mutual affection for email, but our latest conversation had a more urgent tone—thanks to Microsoft’s recent announcement that could throw a wrench in the way we all send emails. If email is your small business’s secret weapon, it’s time to sharpen it.

Main Points from the Conversation:

1. Microsoft’s Email Policy Changes Microsoft has announced stricter deliverability rules—emails that don’t get opened or clicked may not make it into inboxes at all, even if the sender is marked safe. This shift will force marketers to pay more attention to engagement metrics like never before.

2. List Hygiene is No Longer Optional Holding onto disengaged subscribers could hurt your deliverability. Cleaning out your list—removing folks who haven’t opened or clicked in 6–12 months—isn’t just good housekeeping, it’s mission critical.

3. Quality Over Quantity Big lists are out, and meaningful lists are in. A smaller, engaged audience is far more valuable than a bloated list of people who aren’t paying attention.

4. Smaller Campaigns, Better Results Ellen suggests sending smaller, staggered campaigns to improve sender reputation. Large blasts might raise red flags, even if your content is solid.

5. Strategic Email for Every Stage Email can’t be one-size-fits-all anymore. You need tailored messages for prospects, new clients, and past clients—each stage should feel intentional and personal, not like you're just checking a box.

Actionable Takeaways:

• Audit Your List: Check who’s been opening and clicking. If someone’s been snoozing for over 6–9 months, it may be time to let them go—or offer a re-engagement path.

• Segment Your Sends: Break your list into smaller groups and stagger your email sends to improve visibility and avoid being flagged.

• Lean on Third-Party Tools: Ditch BCC blasts. Use trusted email marketing platforms (like Constant Contact, Mailchimp, or Robly) that work hand-in-hand with email providers to boost deliverability.

• Craft Content with a Purpose: Make every email part of a bigger story. Whether it’s educating, engaging, or asking for a review, know your audience and meet them where they are.

• Rethink “Set It and Forget It”: Email marketing isn’t a crockpot dinner. It’s more like sourdough—needs regular attention, care, and a little love.

You know, I’ve spent years telling business owners to get laser-focused. Find your niche, talk to your niche, sell to your niche. It’s like that old saying: “You can’t please everyone, so pick your people.” But every once in a while, someone comes along and flips my perfectly organized marketing world on its head.

That someone was Matt Diamante, founder of Hey Tony, a marketing agency that helps small business owners tackle SEO and social media in ways that actually work. When Matt pitched me the idea of going broad to find your niche, I raised an eyebrow — and then I leaned in. Because sometimes, you have to plant wildflower seeds everywhere before you find out which patch of soil will let your business bloom.

Start Broad to Get Noticed Matt shared how narrowing his content too quickly meant missing out on visibility. Early SEO how-to videos flopped because algorithms didn’t know where to send them. By widening his content to appeal to a broader audience, he started generating massive reach — and, surprisingly, attracting the exact people he wanted.

Make Social Content Personal and Entertaining The trick isn’t just broad topics, it’s how you deliver them. Matt started adding humor, behind-the-scenes moments with his wife, and simple SEO tips framed like secret hacks. This authentic, entertaining style helped his videos go viral while quietly establishing his expertise.

Convert Viral Attention with Consistent, Niche-Focused Follow-Ups Even though viral videos brought millions of eyeballs, the real strategy was in publishing one to three pieces of content daily, mixing broad appeal with posts targeted to DIY business owners. Those niche posts turned casual viewers into inquiries and, eventually, paying clients.

Work Within Your Capacity, But Stay Consistent Matt emphasized that your content output depends on your business goals and available time. When he had more time, he posted several times a day. But the real advice is to do as much as you realistically can, because marketing is often the first thing people drop — and the last thing they should.

People Buy from People, Not Logos Matt’s final nugget: don’t outsource your social media presence. Especially for small businesses, people want to see the face behind the brand. A good example? Judy’s Family Cafe, where the owner turned goofy viral clips into personal invitations to her restaurant. It’s proof that personality-powered content connects.

Try These Simple Steps to Launch Your Go Broad Campaign

Test wide topics to see what gets attention, even if it feels unrelated to your core niche at first.

Infuse humor, personal moments, and relatable scenarios into your content. People want to connect with people, not textbook tutorials.

Balance broad reach with targeted follow-up posts aimed at your ideal customer. Viral reach brings them in — niche content converts.

Commit to a realistic, consistent posting schedule. If you can manage a post a day, great. If it’s twice a week, start there. Just don’t disappear.

Own your presence. Your followers want you, not a generic brand. Show up, be seen, and let them get to know the person behind the business.

We've all had those “seemed like a good idea at the time” moments. Hers involved a Voxer coaching program, and in the spirit of learning from those detours, we unpacked what happened, what she learned, and how there might still be life in that idea yet.

Main Points:

1. Great ideas don’t always land the way you expect. Danielle created a Voxer-based coaching program for personal brand support between sessions. Despite promotions and enthusiasm from peers, it never gained traction with clients.

2. Sometimes it’s not the audience — it’s the offer. Danielle realized her clients come to her for hands-on, real-time messaging work, not asynchronous voice messages. There was a disconnect between what she offered and what her brand promised.

3. Experimentation is always valuable, even when it “fails.” Danielle isn’t sad she tried it. Every experiment, whether it works or not, is a chance to learn, adjust, and discover what truly fits your business and community.

4. Ideas can evolve. Lorraine suggested reframing the Voxer access not as a standalone product but as an add-on to existing branding packages — a “bonus touchpoint” for clients craving extra access and faster feedback.

5. Never give up on a good idea too soon. Danielle’s takeaway was that an idea that flops in one format might thrive in another. It’s all about the packaging, pricing, and timing.

Actionable Takeaways:

• If a new offer isn’t resonating, ask yourself whether it aligns with how clients see you and your core strengths.

• Surround yourself with a trusted business circle — fresh eyes can spot opportunities and blind spots you’ll miss.

• When something doesn’t work, don’t toss it immediately. Consider whether it belongs as part of something else, or if a tweak in messaging or positioning could turn it around.

• Remember: there’s no such thing as a wasted experiment. Every trial leaves breadcrumbs for your next big win.

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