Business Mistakes Most Entrepreneurs Make (and How Coaching Helps You Avoid Them)

Creating cash flow forecasts will show you exactly how much money you’ll have each month for the next year. A coach teaches you which warning signs to watch for and how to negotiate payment terms that actually work for your business. In addition, they help you set up what we call “cash flow buffers”—money set aside specifically for times when payments come in late or unexpected expenses pop up.Starting your own business is exciting, isn’t it? You have big dreams, great ideas, and the drive to make them happen. But here’s something that might surprise you: about 20% of new businesses don’t make it past their first year. Nearly half fail within five years. Those numbers sound scary, but here’s the good news—most business mistakes that kill companies are totally preventable. 

After working with business owners across Palm Beach, Martin Counties, and all over the United States for years, we’ve seen the same problems pop up again and again. More importantly, we know how to help you avoid them.

Think of it this way: you wouldn’t drive across the country without a GPS, right? Running a business without guidance is just as risky. Let’s talk about the biggest mistakes that trip up entrepreneurs and how having a business coach is like having that GPS for your company.

Why You Need to Know About These Mistakes Right Now

Running a business in 2025 is harder than ever before. You’re dealing with new technology, changing customer expectations, and economic uncertainty. The decisions you make today could make or break your business tomorrow.

Here’s something that’ll blow your mind: 80% of business process failures happen because of human error. That means most problems aren’t caused by bad luck or economic downturns—they’re caused by mistakes that someone could have prevented.

Common small business mistakes tend to snowball. One small problem leads to another, and before you know it, your business is in serious trouble. But when you have someone helping you spot these issues early, you can fix them before they become disasters.

The Money Mistakes That Kill Businesses

Money problems destroy more businesses than anything else. Money problems destroy more businesses than anything else. In fact, there are 10 specific reasons why businesses fail, and poor financial management tops the list.

It’s not always about making sales—it’s about managing the money you do have. Let’s dig deep into the financial mistakes that can sink your business and how to avoid them.

Running Out of Cash (Even When You’re Making Sales)

This one kills 82% of small businesses. You might be thinking, “Wait, if I’m making sales, how can I run out of money?” Great question, and it happens way more often than you’d expect.

Here’s the thing about cash flow: it’s not about how much money you’re making on paper. It’s about having actual cash in your bank account when you need to pay bills. You can have $100,000 in sales this month but still not be able to make payroll if that money isn’t in your account yet.

The most common cash flow traps:

• Waiting 30-90 days to send invoices after completing work
• Customers taking 60+ days to actually pay you
• Spending projected income before it arrives
• Not tracking when money is supposed to come in
• Mixing personal and business bank accounts
• Not keeping any money aside for emergencies
• Taking on expenses that grow faster than your income

Let me paint you a picture. You run a marketing agency and land a huge contract worth $80,000. You’re excited, so you hire two new employees, lease better office space, and upgrade your equipment. The problem? Your contract says the client pays in three installments over six months.

Meanwhile, your new expenses start immediately. Two employees need paychecks every two weeks. The office lease is due monthly. The equipment loan payment hits your account automatically. Before you know it, you’re spending $15,000 a month but only getting paid every two months. Even though you’re profitable on paper, you’re broke in real life.

What business owners ask us about cash flow:

“How much cash should I keep in reserve?”

Most experts recommend three to six months of operating expenses. If it costs you $20,000 a month to run your business, you should have $60,000 to $120,000 set aside for emergencies.

“Should I offer payment plans to customers?”

Payment plans can help you win more business, but make sure you can afford to wait for the money. Never offer terms you can’t live with.

“What if a big customer doesn’t pay on time?”

This is exactly why you need that cash reserve. One late payment from a major customer can create a domino effect if you’re not prepared.

“How do I speed up payments from customers?”

Try these tactics: require deposits upfront, offer small discounts for early payment, send invoices immediately after work is done, follow up on overdue accounts weekly, and consider factoring or invoice financing for big accounts.

How a Coach Helps with Cash Flow: A business coach sets up systems that let you see cash problems coming from miles away. Creating cash flow forecasts will show you exactly how much money you’ll have each month for the next year. A coach teaches you which warning signs to watch for and how to negotiate payment terms that actually work for your business. In addition, they help you set up what we call “cash flow buffers”—money set aside specifically for times when payments come in late or unexpected expenses pop up. Think of it as insurance for your business bank account.

Charging Too Little for What You Do

This mistake makes our hearts hurt every time we see it. Undercharging is probably the most dangerous business mistake you can make, and it’s everywhere. We’ve talked to hundreds of business owners over the years, and maybe five of them were actually charging enough.

Here’s what happens when you undercharge: you work harder, stress more, and make less money. Your customers get frustrated because you can’t deliver great service. Your employees leave because you can’t pay them well. You can’t invest in growing your business. It’s a downward spiral that kills companies.

Why business owners undercharge:

• They’re scared customers will say no to higher prices
• They don’t know what their real costs are
• They think being the cheapest option will win more business
• They don’t value their own time and expertise
• They’re competing on price instead of value
• They haven’t researched what competitors actually charge
• They’re afraid to have pricing conversations with customers

Let’s talk about real costs for a minute. Say you’re a web designer who charges $2,000 for a website that takes you 40 hours to complete. That’s $50 an hour, which sounds pretty good, right? But wait—you also spend 10 hours on sales calls, 5 hours on revisions, and 5 hours on project management. Now you’re at 60 hours total, which means you’re really making $33 an hour.

But you’re not done yet. You have to pay for your health insurance, your computer, your software, your office space, and your taxes. By the time you factor in all your business expenses, you might be making $20 an hour. Would you take a job that paid $20 an hour? Probably not, but that’s exactly what many business owners are doing to themselves.

The hidden costs of undercharging:

• You attract customers who only care about cheap prices
• These customers usually demand the most and complain the most
• You can’t afford good employees or quality materials
• You’re always stressed about money
• You can’t invest in marketing or business development
• You have no money for emergencies or slow periods
• Your business becomes a trap instead of a dream

Questions we get about pricing:

“What if customers think I’m too expensive?”

The right customers won’t think you’re too expensive if you’re solving a real problem for them. If price is their only concern, they’re probably not your ideal customer anyway.

“How do I know what to charge?”

Start by figuring out your true costs, including your time. Then research what competitors charge. Look at the value you provide to customers—how much money do you save them or make them? Price based on value, not just costs.

“Should I match my competitor’s lower prices?”

Only if you want to go out of business. There’s always someone willing to work for less. Instead of competing on price, compete on the results you deliver.

“What if I raise prices and lose customers?”

You’ll probably lose some customers, but you’ll make more money from the ones who stay. It’s better to have 10 customers paying $5,000 each than 50 customers paying $500 each.

“How do I raise prices with existing customers?”

Be honest and direct. Explain that your costs have gone up or that you’re adding more value. Give them plenty of notice. Most good customers will understand.

How a Coach Helps with Pricing: A coach will help you do real market research to see what your competitors actually charge (not what they advertise, but what they really get paid). They’ll help you calculate your true costs, including all the hidden stuff you might forget about.

More importantly, they’ll help you understand the value you provide to customers. When you can clearly explain how you save customers money or help them make money, pricing conversations become much easier. A good coach will also help you practice these conversations so you feel confident when customers ask about your prices.

Starting Without a Real Plan (And Why 42% of Businesses Fail)

Here’s a stat that should wake you up: 42% of businesses fail because there’s no market need for what they’re selling. Think about that for a second. Almost half of all failed businesses die because they’re trying to sell something nobody wants to buy.

This happens when entrepreneurs fall in love with their idea without checking if customers actually want it. They spend months or years building something, only to discover that people aren’t willing to pay for it.

The planning mistakes that kill businesses:

• Building a product before talking to potential customers
• Assuming you know what customers want without asking them
• Copying what works in other cities or industries without checking your local market
• Expanding too fast without testing new markets first
• Starting a business just because you’re good at something (instead of because people need it)
• Ignoring warning signs that customers aren’t interested
• Not researching the competition thoroughly
• Planning based on best-case scenarios instead of realistic ones

Let me tell you about Sarah, a baker who made amazing cupcakes. Everyone at parties raved about them, so she decided to open a cupcake shop. She found a great location, signed a lease, bought equipment, and opened her doors. Six months later, she was closing down.

What went wrong? Sarah never asked the hard questions. Yes, people loved her cupcakes at parties, but would they drive across town to buy them? Would they pay $4 each? How often would they buy them? Were there already three other cupcake shops in town? Sarah learned these answers too late, after she’d already spent her life savings.

Market research questions every business owner should answer:

• Who exactly is your ideal customer?
• How many of these people live or work in your area?
• What problem are you solving for them?
• How are they solving this problem right now?
• How much are they willing to pay for a solution?
• Where do they usually look for services like yours?
• What would make them choose you over your competitors?
• How often will they need your product or service?

Common questions about market research:

“How do I find people to talk to about my business idea?”

Start with friends and family, but don’t stop there. Go to places where your potential customers hang out. Join online groups. Post surveys on social media. Offer small incentives for feedback.

“What if people steal my idea?”

Ideas are everywhere. Execution is what matters. It’s better to validate your idea early than to build something nobody wants.

“How many people should I talk to?”

Start with at least 20-30 potential customers. Look for patterns in their responses. If most people say they wouldn’t pay for your service, you need to adjust your plan.

“What if the research shows people don’t want my idea?”

That’s actually good news! It’s much better to learn this before you spend money than after. Use what you learned to adjust your idea or come up with a better one.

“Should I research my competitors?”

Absolutely. Visit their locations, check their websites, read their reviews, and see what customers say about them. This isn’t spying—it’s smart business.

The expansion trap that gets 9% of businesses: Many business owners get excited about early success and try to expand too quickly. They open new locations, launch new products, or target new markets without doing proper research first. Each new market is different, and what works in one place might flop in another.

How a Coach Helps with Planning: Before you invest serious money in your business idea, a coach will help you test it properly. They’ll show you how to do quick, cheap tests to see if people actually want what you’re selling.

A coach will also help you create realistic financial projections based on actual market research instead of wishful thinking. They’ll show you how to identify red flags early and adjust your plans before problems become disasters.

The People Problems That Slow You Down

Trying to Do Everything Yourself

When your business starts growing, you hit a wall. You can’t keep doing everything yourself, but letting go is scary. What if someone messes up? What if they don’t care as much as you do?

Here’s where many business owners get stuck:

• They don’t trust anyone else to do the work
• They don’t have clear ways to train people
• They don’t have systems for people to follow
• Their team doesn’t know how to make decisions without them

How a Coach Helps: A coach helps you figure out which tasks only you can do and which ones you can teach someone else. They’ll help you create simple systems that let your team succeed without you having to micromanage everything.

Not Keeping Up with Technology

Technology changes fast, and it’s confusing. Some business owners go crazy buying every new gadget, while others ignore technology completely. Both approaches can hurt your business.

Common small business mistakes with technology:

• Buying expensive software you don’t actually need
• Using outdated systems that waste time
• Not protecting your business from hackers
• Making your team use tools they don’t understand

How a Coach Helps: A coach looks at your business goals first, then helps you pick technology that actually helps you reach those goals. No more buying stuff just because it looks cool or ignoring updates because change is hard.

Ignoring Your Money Numbers

Many business owners avoid looking at their financial reports. Maybe numbers aren’t your thing, or maybe you’re afraid of what you’ll find. But ignoring your finances is like driving with your eyes closed.

Money management problems include:

• Not knowing if you’re actually making a profit
• Having no idea where your money goes each month
• Not planning for taxes (ouch!)
• Not tracking which parts of your business make the most money

How a Coach Helps: Don’t worry—you don’t need to become an accountant. A coach will help you set up simple systems to track the numbers that matter most. They’ll teach you to read the story your numbers are telling you about your business.

Marketing Mistakes That Waste Your Time and Money

Trying Every Marketing Trick Without a Plan

Social media, email marketing, paid ads, networking events—there are so many ways to market your business! The problem is, many business owners try everything at once instead of focusing on what actually works for their customers.

Marketing mistakes that drain your budget:

• Posting randomly on social media without strategy
• Trying to be everywhere instead of being great somewhere
• Not tracking which marketing actually brings in customers
• Spending money on ads without knowing if they work

How a Coach Helps: A coach helps you figure out where your ideal customers spend their time, then focuses your efforts there. Instead of spreading yourself thin everywhere, you’ll go deep on the channels that actually bring you business.

Not Having a Real Sales Process

Even if you have the best product or service in the world, you still need to know how to sell it. Many business owners wing it when talking to potential customers, which means they miss out on sales they should have won.

Sales problems that cost you money:

• Not knowing what to say when someone asks about your prices
• Talking about features instead of benefits
• Not following up with people who seem interested
• Not asking for the sale (this happens more than you think!)

How a Coach Helps: Sales coaching can increase your revenue by up to 16.7%. A coach will help you create a simple process for turning interested people into paying customers. No high-pressure tactics—just honest conversations that help people understand how you can help them.

How Business Coaching Keeps You Out of Trouble

Getting a Fresh Perspective on Your Business

When you’re in your business every day, it’s hard to see problems clearly. It’s like trying to read the label on the bottle you’re inside of. 80% of people who work with coaches report feeling more confident, and 70% see improvements in their work performance and relationships.

What a coach brings to the table:

• They’ve seen your problems before and know how to fix them
• They ask questions you never thought to ask
• They help you see opportunities you’re missing
• They keep you accountable for making changes

However, success depends on working with the right person, so it’s important to know what to look for when choosing a business coach before you commit.

Learning from Other People’s Mistakes

Here’s something cool about working with an experienced business coach: they’ve worked with hundreds of other businesses. That means they’ve seen every mistake in the book, and they can help you avoid the ones that trip up most entrepreneurs.

One in six entrepreneurs works with a coach to improve their performance. Even more interesting: 33% of founders who get mentored by successful entrepreneurs become top performers themselves. Only 22% of entrepreneurs have mentors when they start their businesses, which might explain why so many struggle.

Getting Proven Systems Instead of Making It Up

Successful businesses aren’t built on luck—they’re built on systems that work. A coach doesn’t just give you advice; they help you build processes that make your business run smoothly even when you’re not there.

Questions Every Business Owner Should Ask Themselves

Take a minute to honestly answer these questions. If you say “no” to any of them, you might be setting yourself up for some of those business mistakes we’ve been talking about:

• Do you have enough money saved to pay your bills for six months if sales slow down?
• Can you explain what makes your business special in one simple sentence?
• Do you look at your financial reports every month and actually understand them?
• Have you talked to customers to make sure they really want what you’re selling?
• Are your prices based on your actual costs plus a healthy profit?

If some of these made you uncomfortable, don’t worry. Most business owners struggle with at least a few of these areas. The important thing is recognizing where you need help.

Building Your Business the Right Way

The difference between businesses that thrive and those that become another failure statistic often comes down to having help when you need it. Think about it: every professional athlete has a coach, even though they’re already great at what they do. Why? Because coaches help them see things they can’t see themselves and push them to get even better.

Your business deserves the same kind of support. Here’s what good business coaching helps you build:

Money Management Systems:

• Simple ways to track your cash flow
• Monthly check-ins to review your numbers
• Planning ahead for busy and slow seasons
• Knowing which parts of your business make the most money

Understanding proven strategies for business success is what separates thriving businesses from those that struggle.
Day-to-Day Operations:

• Clear procedures so your team knows what to do
• Ways to make sure your customers get great service every time
• Systems that work even when you’re not there
• Plans for growing without losing quality

Long-Term Planning:

• Regular strategy sessions to plan your next moves
• Keeping an eye on your competition and industry changes
• Setting goals that actually mean something
• Preparing for problems before they happen

Don’t Let These Mistakes Derail Your Dreams

Here’s the bottom line: running a successful business is hard, but it doesn’t have to be lonely. The business mistakes that destroy most companies are predictable and preventable. You just need someone in your corner who’s been there before and knows how to help.

At AMB Performance Group, we’ve helped business owners across Palm Beach, Martin Counties, and throughout the United States avoid these common small business mistakes and build companies that actually work for them, not against them.

We don’t just point out problems—we roll up our sleeves and work with you to fix them. Whether you need help with money management, team building, marketing, or planning for growth, we’ve got systems that work.

The statistics are clear: businesses with proper coaching and guidance do way better than those trying to figure it out alone. Don’t gamble with your dreams when help is available.

Ready to stop making costly mistakes and start building the business you’ve always wanted? Contact AMB Performance Group today. Let’s have a conversation about where you want your business to go and how we can help you get there safely. Your future self will thank you for making this call.