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The 15 Most Expensive Mistakes I Made Building an 8-Figure Business and How You Can Avoid Them
December 2025
Read time: 7 minutes and 45 seconds
O ver the past 15 years, I’ve made millions of dollars in mistakes. Some cost me clients. Some cost me sleep. A few almost cost me the business. But here’s the thing about expensive lessons: You only have to learn them once if you’re paying attention. And you don’t have to learn them at all if someone who’s already been through it is willing to share. On Jan. 25, 2026, Newsletter Pro turns 15. We’ve grown from a one-person operation called “Solution Marketers” to an eight-figure company with 50-plus employees, serving hundreds of clients across four countries. Along the way, I’ve learned what works, what doesn’t, and, more importantly, why most businesses struggle with the one thing that matters most and adds the most value to their business: retaining the customers they already have.
What follows are 15 lessons I wish I’d known in 2011. Some will save you money. Some will save you time. And if you’re like most business owners I work with, at least one will completely change how you think about growing your company. 1. Existing customers are your real growth engine. Like most entrepreneurs, I used to get more excited about new leads than current customers. New leads feel like progress. They’re visible. They’re easy to brag about. However, upon closer examination of the numbers, the pattern was clear: Most businesses generate 80% or more of their revenue from repeat customers, while acquiring new customers costs 5–25 times more (depending on industry) than retaining an existing one. Repeat customers spend, on average, 67% more than new customers. A study on subscription businesses found that a 5% increase in retention grew profits by 60% by the fifth year. Meanwhile, customers acquired through referrals are worth 16% more over their lifetime and stay 37% longer. If you’re always chasing new opportunities and ignoring current ones, you’re leaving the easiest money on the table. The lesson: Your highest-ROI growth lever isn’t acquisition; it’s keeping the customers you already have engaged, referring, and spending. It is just a little more difficult to track, and you see the benefits over time, which is what holds people back from pulling this lever. 2. The bottleneck is you. Not long ago, I agreed to review all the pricing on a campaign. Simple task. But travel and other work kept piling up, and the project sat on my desk for five days. Here’s the kicker: I wasn’t the only person who could do it. I just jumped in and said I’d take care of it.
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3. Stop solving problems you don’t have yet. Early on, we’d get one or two similar but minor complaints, and we would add a double-check for every customer going forward. Sometimes, it was a training issue or customer preference. Sometimes, it was just a one-off problem we’d never see again, but all of a sudden, those issues turned into a permanent process change. Then another. Then another. Eventually, we had this ballooning checklist of never- ending double-checks for issues that were rarely or never repeated. We were building elaborate systems for one-off problems while sometimes ignoring the issues hitting us in the face every day. Not our best for sure. Real problems show up screaming multiple people affected, consistent patterns, and measurable impact. One- off problems whisper. When we finally focused on solving the pain we could actually measure, rather than hypothetical scenarios, the business drastically improved. The lesson: Focus ruthlessly on urgent problems, schedule time for important but not urgent issues, not catastrophes that exist only in someone’s head. 4. 68% leave because they feel forgotten. Here’s a stat that should scare you: A study by the Rockefeller Corporation found that 68% of customers who leave a business do so because they feel the company doesn’t care about them. Not price. Not product. They just felt forgotten. Early on, before I started Newsletter Pro, I made the same mistake most business owners make. I’d close a deal, deliver solid work, then immediately chase the next sale. I figured good customers would stick around and remember me when they needed us again. Wrong. The brutal reality is this: If you’re not consistently in front of your customers, they forget you exist. And when they forget you, they’re
Those five days brought the entire project to a standstill. My team was ready to move. But because I inserted myself into a decision I didn’t need to own, I became the problem. Teams with high autonomy are 26% more productive than those with low autonomy, but I’d still convince myself I needed to be involved. The shift happened when I started asking one question before touching anything: “Am I the only person who can do this?” If the answer is no, I step back. I set clear outcomes, let my team own the “how,” and only check in at agreed milestones. When I stopped being involved in every decision, the company grew faster with far less stress.
The lesson: If you’re in every decision, you’re also in the way.
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“I told my assistant that if we ever have to cut costs, Newsletter Pro should be the last thing to go. People love the newsletter so much that we would have an outright rebellion on our hands
if we stopped sending it.” –Geneva P, Promise Law
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wide open to whoever IS showing up, even if that competitor charges more and delivers less. Out of sight means out of mind, and out of mind means out of business. Here’s the kicker: Most business owners think they’re communicating when they’re really just talking about themselves. Every message is about their new service, their latest promotion, or what they need from the customer. They forget that customers don’t care about your business — they care about their problems and whether you can solve them. The lesson: Consistent communication isn’t a nice-to-have; it’s the difference between customers who stick around and customers who silently walk away. You can’t retain people who feel forgotten. 5. Always plan time to work on the business. Shortly before I hired my first assistant, I’d come home every night and complain that I felt like I didn’t accomplish anything. And I was right. I’d spent my whole day putting out fires and working on low-level tasks anyone could have done. The problem wasn’t that I was working hard. The problem was that I was working on the wrong things. Research shows micromanagers spend 78% of their day reviewing others’ work instead of engaging in strategic planning. That’s a life sentence of busy work disguised as leadership. When I finally started asking, “Is this something only I can do?” before saying yes to anything, my calendar and our growth curve changed. The shift from “in the business” to “on the business” is the difference between working hard and building something with real value. The lesson: If you want millionaire- or billionaire-level results, you can’t operate like an overworked assistant. 6. Focus on your lane, not the economy. I started Newsletter Pro during the recovery from the housing crisis. Everyone said the sky was falling. The doom-and-gloom narrative was everywhere, and I bought into it. One day, I wasn’t feeling motivated; actually, I was a little depressed about the state of things. My team emailed me the previous month’s revenue and sales numbers, and it hit me like a ton of bricks: We were growing. Despite all my worrying about the economy and the future, we were actually growing. I realized I would always be able to outwork, outthink, and out- hustle any issue. Once I focused on what was true in my world, rather than what was happening around the world, we doubled our revenue in about four months. I stopped obsessing over headlines and started obsessing over my reality. Now, I plan for the worst and expect the best. This positions me to win regardless.
The lesson: Worry less about the headlines. Worry more about the experience your customers are having with you right now. 7. You’re not bothering anyone unless you’re boring. One objection I hear from clients on the email side of our business, more frequently than on the print side, but I’ve received it in both places, is “I don’t want to bother my customers by reaching out too often.” This drives me crazy because it’s based on a false assumption.
You’re not bothering anyone unless your content is boring. Research shows 61% of people actually want to hear from businesses weekly, and when asked about email frequency, 48% said they don’t want fewer emails; they want better content. The problem isn’t too much communication. It’s that most communication sucks. Sporadic contact is worse than frequent contact. When you only reach out every few months, customers forget who you are, why they hired you, and what problem you solved. Your brand recognition drops. You become just another name in a crowded inbox and less crowded mailbox, instead of a trusted advisor they think of first. Here’s what actually bothers people: irrelevant content, sales pitches disguised as value, and companies that disappear for six months then suddenly need something. Consistent, valuable communication? That builds trust and keeps you top of mind when they’re ready to buy or refer.
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For example, if you bend over backward for customers but burn out your team, you’ll have employee turnover problems that get expensive fast. If you only optimize for profit, customers feel squeezed, and you get churn. If you never reinvest in the business, it becomes stale, and with how fast the world is changing, that is the last thing you want. If you ignore ownership, the business doesn’t turn a profit, or at least not a good one, and it will either be sold or closed down. I use this mental checklist all the time: “Which master is this decision serving? Which one haven’t we served in a while? How close to a win-win can we get?” The lesson: Sustainable business success requires balance across all four stakeholders, not optimization for one. Next month, I’ll share lessons 9–15, including the three mistakes that cost me the most money and the one system that generates more ROI than everything else combined. If any of these first eight lessons hit home, email me at Shaun.Buck@newsletterpro.com and let me know which one. I read every response.
The lesson: Stay consistently in front of your customers, at a minimum of once a month. They won’t think you’re annoying; they’ll think you care. And customers who feel cared for tend not to leave. 8. Every business has 4 masters. Over the years, I’ve learned that every decision in business really answers to four “masters”: your customers, your employees, the business itself, and the ownership. The catch? You can’t please all four equally with every decision. But if you consistently sacrifice one of them, that relationship will eventually fail.
–Shaun
P.S. You’re likely getting this around Christmas or the New Year, so from my family to yours, Merry Christmas and Happy New Year! And if you want to make 2026 your best year for customer retention and revenue growth, let’s talk. Reply to this email or call (208) 297-5700 to schedule a time.
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