Check out our January newsletter!
15 YEARS, 15 LESSONS: PART 2 The Mistakes That Cost Me the Most (and the Systems That Fixed Everything)
January 2026
Read time: 9 minutes, 15 seconds
L ast month, I shared the first nine lessons from 15 years of building Newsletter Pro. Based on the emails I got back, three hit hardest: realizing you’re the bottleneck (#2), the fact that 68% of customers leave because they feel forgotten (#4), and understanding that you’re not bothering customers unless you’re boring them (#7). If those lessons resonated with you, the final six are going to hit even harder. These last lessons cover the mistakes that cost me the most money, the systems that generate the highest ROI, and the one thing every successful business does that unsuccessful ones skip. By the end, you’ll know exactly where you’re leaving money on the table and how to fix it. 9. Walk before you run. In the early days, I set insane goals with unrealistic timelines because that’s what hustlers are supposed to do, right? All gas, no brakes. In reality, it led to half-finished initiatives, tons of stress and self-doubt, and a stressed-out team. We’d launch too many things at once and execute none of them well. That’s not productivity; that’s chaos. What actually worked was boring by comparison: clearly defining point A (where we were), point B (where we wanted to be in 12 months), and then ruthlessly committing to small, consistent steps. To come up with those steps, we started from the end goal and asked what needed to be true to reach that goal. Once we had that info, we worked backward, getting more and more granular as we got closer to the first few weeks and months of our goal’s start time. Progress compounds a lot faster when you don’t have to keep rebuilding what you rushed the first time. The lesson: Progress compounds more reliably through consistency and clearly defined goals. It works even better with a clearly defined “why” attached to the goal.
10. Most salespeople stop right before the sale. Here’s a staggering stat: 48% of salespeople never make a single follow-up attempt after initial contact, and 44% give up after just one try. Meanwhile, 80% of sales require five or more follow-ups to close. Think about that disconnect. Most sales occur after the fifth contact, but most salespeople quit after the first or second attempt. The same pattern plays out in almost every business. You spend money generating leads, thousands of dollars on ads, events, referrals, and then watch those leads go cold after 30–60 days because nobody followed up. It’s like paying for groceries, then leaving them in the parking lot to rot. I don’t think about leads as “hot” or “cold.” I think about them as future customers on different timelines. Research shows that at any given moment, only 3% of your market is actively buying. Another 40% are poised to begin, while 56% are not yet ready. If you only talk to the 3%, you’re ignoring 97% of potential revenue.
The math is simple. Following up with a prospect for a year might cost you $12 for monthly newsletters, or pennies per person for weekly emails, to provide value and stay top of mind long after all your
competitors stop communicating. It is not smart to spend all your money and energy on expensive lead generation and give up on the cheap part, which is nurturing those leads. The lesson: Leads are expensive to generate but cheap to nurture. Build a system that follows up relentlessly, not with desperate sales pitches, but with value that keeps you top of mind. The fortune really is in the follow-up. Continued on Page 2 ...
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The lesson: Own your results, not your excuses. When something doesn’t work, look at what you can change: your approach, your process, your strategy. The only thing you can’t do is blame the tools. 12. Businesses, like people, get stuck unless you level up. There’s a dangerous zone most businesses hit somewhere between $2–$5 million in revenue. I’ve watched multiple clients hit this ceiling and stay there — or worse, start declining. The problem isn’t their product, their market, or their team. The problem is that the owner refuses to evolve. When I started Newsletter Pro, the business revolved around me. I could have my hand in every pot, and that works when you’re small. But there came a point where I had to decide: Did I want to stay a small-business owner running a small operation, or did I want to become a CEO building something bigger? The transition sucked. I had to let go of being involved in everything. I had to trust systems instead of my own eyes on every project. I had to stop being the star player and become the coach. Many entrepreneurs I know can’t make this shift, or won’t. They’d rather stay comfortable at less than $1 million to maybe $3 million doing everything themselves than scale to $10 million by stepping back. Here’s what I realized: If you don’t level up your skills, you cap your business at your current skill level. The company can only grow as much as the leader is willing to grow. I had to invest in learning how to be a CEO, not just a scrappy entrepreneur. That meant different books, different mentors, different habits, and, honestly, becoming a different version of myself. The lesson: Your business will hit a ceiling that matches your current capabilities. The only way to break through is to level yourself up first.
11. Own your results, not your excuses. Years ago, I was talking with a prospect who told me marketing never works for him. Then he asked me to sign him up for newsletters. I told him that was a mistake. He was confused. Why wouldn’t I want his business? I explained that if all marketing fails for him, newsletters would fail, too, because the problem wasn’t the marketing. Something was wrong with his methods or his business. He insisted on signing up anyway. After about a year, the same customer called and told me that the newsletter doesn’t work. I wasn’t shocked at all to get this call. I reminded him of our conversation when he signed up and told him, “You need to take a hard look at yourself, your services, and/or your employees, because it wasn’t the marketing that wasn’t working correctly.” I bring this up because there’s a flip side to the “launch before you’re ready” mentality that nobody talks about. When I started my company, we weren’t even called Newsletter Pro; we were Solution Marketers, a lead generation marketing agency that also did newsletters. It wasn’t the perfect name. It wasn’t the perfect positioning. The business model wasn’t dialed in. But I launched anyway because I knew waiting for perfect meant never starting. Here’s the difference between me and that prospect: When something didn’t work, I changed my approach. I adjusted the business model, tested different positioning strategies, and ultimately rebranded the company entirely. He looked for someone else to blame.
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Building Relationships to Help Small Businesses Succeed.
208.297.5700
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13. The platform you don’t control can kill your business overnight. Many years ago, I was banned from both Meta and Google Ads for another business I was running. No warning. No appeal that mattered. Just gone. Within six months, that ban killed an entire info business I had in the dry-cleaning niche. Years of work, gone, because I didn’t control the platform. Here’s the hard truth: Email deliverability keeps dropping. Meta and Google can and will ban you from their platforms. Facebook’s organic reach averaged just 1.4% in 2024. Instagram sits at 3.5%–4%. Even email typically only reaches 20%–30% of your list, depending on your industry. If email or social is your only connection to customers, you’ve already lost access to 70%–98% of your ability to reach them. That’s why I push clients to collect real, multichannel contact information: name, email, mailing address, and phone at a minimum. Print, email, social, and text together give you resilience. If one channel gets shut down or stops working, the others keep you connected. The lesson: Build your contact list across multiple channels. The platform you bet everything on today might ban you tomorrow.
ad. They spent seven weeks using artificial intelligence (AI) to create a “clever” commercial showing people slipping on ice, burning cookies, getting tangled in lights — then suggesting they hide from their families at McDonald’s until January. Technically proficient. Strategically terrible. They pulled it after massive backlash. One viewer nailed it: “No artistry. No wit. No charm. No warmth. No humanity. You can tell it’s AI from a million miles away.” Coca-Cola made the same mistake twice with AI Christmas ads that consumers called “creepy” and “soulless.” Be real. Share genuine stories. Let your values show. Don’t share your darkest secrets, political views, or every controversial opinion to be authentic, unless that is part of your brand. Our best-performing content at Newsletter Pro, for both clients and ourselves, has always been when we told real, personal stories. Not polished. Not written by AI. Just human. The lesson: Authenticity can’t be faked, but it also isn’t permission to be unfiltered. Be genuine. Be thoughtful. Be human. 15. Story compresses years of learning into minutes. Every business is sitting on a gold mine of content — it’s just waiting to be tapped. The biggest resource for a company to market, in many cases, is the owner. Yet most business owners are stuck in the grind instead of working on what matters. Time and again, I’ve seen the same pattern: Facts and features bounce off people while stories stick. You can tell someone, “Retention matters,” and they’ll nod and forget. Or you can tell them about the client who almost left, how a relationship
Progress compounds a lot faster when you don't have to keep rebuilding what you rushed the first time.
14. Authenticity is your competitive advantage, but it has guardrails. Being authentic doesn’t mean sharing every dark thought or controversial opinion with your customers. There’s a line between genuine and reckless. Abercrombie & Fitch CEO Michael Jeffries crossed it when he said, “Only cool, good-looking people should shop here.” That authentic but offensive comment tanked the company, resulting in a $60 million sales drop. However, there’s a flip side: You can’t fake authenticity either. McDonald’s learned this the hard way with their 2025 Christmas
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Building Relationships to Help Small Businesses Succeed.
208.297.5700
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touchpoint pulled them back, and what that was worth over five years. One, they’re more likely to remember at least how the story made them feel, and the other, they won’t remember it at all. Research shows that 88% of people trust recommendations from friends and family more than any other form of advertising. Why? Because those recommendations come wrapped in real experiences, real stories, and from real people. Story makes the abstract concrete. It keeps existing customers engaged, builds a connection with them, gives them something worth sharing with others, and helps prospects see themselves working with you. Generic content may as well be invisible. But personal stories are what people want. That’s exactly why we weave ghostwritten personal stories and other content into the newsletters we create for clients and ourselves. Our best-performing content at Newsletter Pro has always been real, personal stories. Customers won’t remember the bullet points from your brochure, but they will remember how you handled a tough situation, helped someone like them, how you made them feel, or bounced back from a mistake. The lesson: Story is the shortcut to trust. And trust is everything in business today.
Here’s what I want you to do:
Call us at (208) 297-5700 or email me directly at Shaun.Buck@newsletterpro.com and tell us which of these 15 lessons hit home for you. We’ll schedule a 30-minute call to look at your business, identify where you’re losing customers (or revenue), and map out exactly what it would take to fix it. No pressure. No hard sell. Just a conversation about whether what we do can help you keep more of the customers you work so hard to get.
Be real. Share genuine stories. Let your values show.
Sound fair?
Here’s What These 15 Lessons Taught Me Over 15 years, I’ve learned that the most expensive mistake businesses make isn’t failing to get new customers. It’s failing to keep the ones they already have. You can have the best product, the strongest team, and a brilliant strategy, but if customers forget you exist between purchases, none of it matters. That’s exactly why Newsletter Pro exists. We solve the problem almost every business has but most don’t realize: consistent, valuable communication that keeps you top of mind without requiring you to do the work. If you’re reading this and thinking, “I’m making one or more of these mistakes right now,” you probably are. The good news? They’re all fixable. The better news? You don’t have to figure it out alone.
If you’re serious about making 2026 your best year for retention, referrals, and revenue growth, let’s talk. We’ve been doing this for 15 years. We know what works. And we’d love to help you implement it.
–Shaun
P.S. If you made it through all 15 lessons, you're already ahead of most business owners. The question is: What are you going to do about it? Book a call. Let's figure it out together.
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NewsletterPro.com
Building Relationships to Help Small Businesses Succeed.
208.297.5700
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