“Chaos Costs You: Why Buyers Devalue Poorly Planned Businesses”
Business Valuation Isn’t Just About Revenue.
Over the years, I’ve worked with plenty of business owners who’ve been shocked by what their business valuation is — and not in a good way.
They assume that if their turnover looks healthy and the profit margin is decent, then they’re sitting on a goldmine. But when they start talking to buyers, investors, or brokers, the reality hits: business valuation isn’t just about the numbers — it’s about how well your business is structured, how clearly it can grow, and how easily someone else can run it.
One client of mine — let’s call him Dave — ran a service business that was bringing in solid six-figure revenue. Good team, loyal clients, good brand. But when he approached a buyer, the deal fell apart during due diligence. Why? There was no clear business plan. No documented systems. No formal strategy beyond, “We’ve always done it this way.” The buyer saw risk, not value.
Contrast that with another business I worked with — a smaller operation, actually. But they used a structured 365/90 planning process. Every quarter, they set clear goals, tracked performance, documented decisions, and refined their systems. When a buyer came to the table, they didn’t just see numbers — they saw a business with direction, predictability, and transferability. That deal closed quickly and at a premium.
Here’s the truth: a strong business plan tells buyers, “This business knows where it’s going, and it doesn’t rely on guesswork or gut feel.”
It doesn’t matter whether you’re looking to sell now or five years from now. The time to start strengthening your valuation is today, and your business plan is one of the most powerful tools you’ve got.
In this blog, I’ll show you exactly how a structured planning system — like 365/90 — can increase the perceived and actual value of your business. We’ll dig into what buyers are really looking for, why planning reduces their risk, and how the right plan can make your business easier to run, grow, and ultimately sell.
Because your business isn’t just a job. Done right, it’s an asset — and assets are worth more when they’re built on structure, not chaos.
1: What Buyers Are Really Looking For.
Let’s get one thing straight — buyers aren’t just buying your revenue. They’re buying confidence.
When someone considers purchasing your business, they’re not just doing the math. They’re weighing up risk, control, and future potential. And here’s what separates businesses that get a strong valuation from those that don’t: structure.
Buyers want to know:
- Is this business stable?
- Can it grow beyond where it is now?
- Can I run it without the founder being involved in everything?
- Are the operations repeatable — or does it all live inside one person’s head?
This is where most small business owners fall short.
I’ve seen businesses with decent cash flow get undervalued simply because they couldn’t prove they knew what they were doing quarter by quarter. No strategy. No performance reviews. No documented targets. It’s like trying to sell a car without a dashboard — the buyer sees potential crashes ahead.
Now contrast that with a business that runs on a system like 365/90, where every 90 days, there’s a documented sprint of goals, metrics, and review points. Buyers walk in and immediately see:
- Clear evidence of past performance.
- A roadmap for future growth.
- A team aligned around regular planning and accountability.
That’s when trust kicks in.
Buyers don’t want to rebuild your business after they buy it. They want to step into something that’s already functioning like a machine. The more you can show that your business has momentum and structure, the more valuable it becomes.
A client of mine recently had two offers for their business. One buyer offered a standard multiple based on EBITDA. The other, who had seen their documented 365/90 plans and systems, offered 20% more because they believed the business was plug-and-play.
That’s what structure does. It doesn’t just make your business easier to run — it makes it more attractive and more valuable.
2: A Plan De-Risks the Business for the Buyer.
When a buyer looks at your business, they’re not dreaming about your product, your logo, or how passionate you are. They’re asking themselves one simple question:
“What could go wrong if I take this over?”
That’s risk, and risk kills deals or drives your valuation down fast.
Most small business owners unknowingly build high-risk businesses. Everything revolves around them — their decisions, their relationships, their hustle. The problem is that kind of business can’t be transferred. The minute you leave, the engine stops running. Buyers see that and back away — or use it to justify a lower price.
This is where a clear, consistent business planning system becomes one of your biggest assets.
When you’re working with a system like 365/90, you’re not just reacting to problems — you’re anticipating them. You’re reviewing performance every 90 days. You’ve got plans in place. You’re documenting processes, correcting mistakes, and tracking outcomes.
That gives a buyer massive peace of mind.
Imagine walking into a business that has:
- A clear one-year strategic roadmap.
- Quarterly objectives and KPIs in place.
- Evidence of consistent reviews and improvements.
- Standard operating procedures (SOPs) that are written and in use.
- A rhythm of execution, not chaos.
Suddenly, the risk starts to disappear. And with less risk comes higher value.
I worked with a client in professional services who had no formal planning when we first spoke. Everything was reactive — projects landed because they were well-connected, but there was no repeatable engine underneath it. We implemented 365/90 planning, and within 12 months, they had predictable revenue, clear targets, and a documented delivery system.
When it came time to sell, the buyer saw a stable, growing, low-risk business, and they paid accordingly.
Bottom line? The less reliant your business is on you, the lower the perceived risk… and the higher your business will be valued. A strong plan isn’t just smart — it’s money in the bank.
3: Growth Potential Is Easier to Trust with a Clear Roadmap.
Every buyer wants growth. But they don’t just want to hope it’s there — they want to see the path clearly laid out.
The most valuable businesses aren’t just the ones that are doing well now. They’re the ones that show credible, structured growth potential. That’s where a proper business planning system — like 365/90 — becomes a huge differentiator.
Let me be blunt: vague statements like “We’re planning to expand next year” don’t impress buyers. What does impress buyers is a clearly defined growth plan broken into achievable 90-day goals, supported by data, with regular reviews and adjustments.
Here’s what that looks like in real terms:
- A strategic roadmap outlining how you’ll acquire new customers.
- Documented marketing campaigns tied to KPIs.
- Plans for product expansion or service upgrades.
- Hiring plans matched to growth phases.
- Sales targets that are broken down into weekly and monthly metrics.
It shows that growth isn’t a guess — it’s being deliberately engineered.
I had one client in ecommerce who was generating decent sales but couldn’t convince investors to come in. The problem? No one could see how it would scale beyond the founder’s current effort. We applied the 365/90 system to create a detailed 12-month roadmap, including advertising targets, email campaign plans, conversion optimisations, and inventory scaling.
When we put that in front of the next investor, they didn’t just nod — they wrote a cheque, because the plan de-risked the uncertainty around growth.
The point is this: growth is only valuable if it’s believable. A 365/90 planning system gives buyers and investors hard evidence that you’re not just winging it — you’re building on something repeatable, trackable, and scalable.
And that kind of clarity? It turns into cash when you’re negotiating valuation.
4: Transferability and Owner Independence.
Here’s a hard truth that catches many founders off guard:
“If your business can’t run without you, it’s not really a business — it’s a job.”
And buyers don’t pay top dollar for jobs.
The more your business depends on your personal involvement — your decisions, your client relationships, your daily firefighting — the harder it is to sell. Or, if it does sell, the price gets dragged down because the buyer knows they’re inheriting a people-risk problem.
That’s why transferability is such a key factor in business valuation — and it’s exactly where a structured planning process like 365/90 comes in.
When your business runs on a 365/90 system, you’re embedding clarity and accountability into the business itself, not just into you. Here’s what that looks like:
- Roles and responsibilities are documented and distributed.
- Each 90-day sprint defines who is doing what, and by when.
- Systems and SOPs are updated as part of quarterly reviews.
- Progress is reviewed regularly without you needing to micromanage.
That level of operational maturity shows a buyer they’re not just buying you — they’re buying a functioning system with people and processes that know how to execute.
I worked with a consultancy where the founder was in every client meeting, made every decision, and signed off on every piece of work. They were burning out and couldn’t grow. We introduced 365/90, began delegating based on clear quarterly outcomes, and built a rhythm of performance management into the team.
Twelve months later, the founder was only involved in strategic decisions, and when they received an unsolicited acquisition offer, the buyer made it clear:
“The business runs itself. That’s what we’re paying for.”
So if you’re serious about building a business with real value — not just income — you have to reduce founder dependence. Planning isn’t just about growth. It’s about building a machine that can survive — and thrive — without you in the middle of it.
And that’s what buyers want.
5: Planning and Perception — Business Valuation Is Part Psychology.
Here’s something most business owners overlook: valuation isn’t just numbers — it’s perception.
You might have a solid business, decent profit, loyal customers… but if it looks messy, unstructured, or reactive, buyers get nervous. Why? Because they start to imagine what could go wrong. And when risk creeps into their minds, value comes down.
This is where planning plays a powerful — and underappreciated — psychological role.
When a buyer sees clear, consistent documentation — annual goals, 90-day plans, performance reviews, progress tracking — they don’t just think, “This owner is organised.” They think:
“This business is stable. It’s being led with discipline. It’s less likely to surprise me.”
That’s how you shift from being perceived as a high-risk investment to a strategic acquisition.
Think about it. If you walked into two businesses doing identical numbers — same turnover, same margins — but one has a chaotic desk covered in sticky notes and half-baked ideas, and the other has a dashboard of metrics, updated action plans, and a team that knows the quarterly objectives… which one do you trust more?
Planning builds that trust.
It’s the same reason well-written CVs win job interviews. It’s not just about what you’ve done — it’s how clearly you can show it, explain it, and build on it. The appearance of clarity creates confidence.
And that confidence has a value attached to it.
I’ve seen businesses increase their valuation by 10–30% simply by improving how they present and prove their systems through planning documentation. No magic. Just structure, discipline, and evidence.
That’s what the 365/90 planning system gives you — not just operational results, but a psychological edge in any negotiation. Because buyers don’t just buy potential, they buy certainty. And structured planning makes certainty visible.
Why Some Buyers Look for Chaotic Businesses.
Here’s a twist that most business owners don’t expect: Some of the smartest buyers actually go looking for messy, unstructured businesses.
Why? Because they know that chaos creates opportunity — and profit.
These buyers are experienced operators, not first-timers. They’re not scared off by a lack of systems or planning. In fact, they’re counting on it. Because they know if a business is generating decent revenue despite the chaos, there’s massive upside once structure is applied.
They see the gaps — and know exactly how to close them.
- No documented processes? They’ll build SOPs.
- No consistent sales system? They’ll install one.
- No 90-day goals, no metrics, no rhythm of accountability? Easy fixes — and fast wins.
They often use planning systems like 365/90 themselves. So they know that implementing a structured planning process can rapidly increase efficiency, profitability, and ultimately, resale value.
To them, buying a chaotic business is like buying a house that needs a renovation — the bones are there, the location is good, and the price is lower than it should be. With the right improvements, the return can be huge.
I’ve seen this play out firsthand. A client of mine sold a marketing agency with great clients but no internal planning. A buyer came in, applied a 365/90 system, cleaned up the operations, doubled EBITDA in 18 months, and flipped it for 3x what they paid.
So if you’re a seller, understand this:
“Chaos might attract a buyer, but it will cost you control over the price.”
The more structured your business is, the less someone can justify discounting it. The less structured it is, the more likely they’ll see your mess as their margin.
Final Word: A Better Plan Builds a Better Price.
At the end of the day, your business valuation is based on more than just revenue or profit. It’ll be judged on how predictable, transferable, and scalable it is — and a solid planning system is the backbone of all three.
If you want to sell for top dollar, your buyer needs to believe they’re stepping into a business that runs smoothly without you. One with a clear path for future growth. One where the risk has been reduced because the thinking has already been done — and documented.
That’s exactly what the 365/90 Planning System delivers.
It turns your business into a strategic machine, with clear goals every 90 days, regular performance reviews, and a structured approach to execution. It doesn’t just help you grow — it shows future buyers how you grow. And that makes them far more confident to invest.
Yes, some buyers will sniff around looking for chaos they can exploit. But if you want control, leverage, and a better price, you need to make your business look like a low-risk, high-opportunity asset. Because value is perception, and perception is shaped by planning.
If you’re serious about increasing the value of your business, whether you’re selling now or five years from now, it starts with how you plan today.
Your Next Step: Ready to Build a Business That’s Worth More?
If you want to increase your business valuation — whether you’re preparing to sell or just want to build a better, more scalable company — the first step is simple:
Get your planning system in place.
That’s exactly what the 365/90 Game Plan Accelerator is designed to do. You’ll create a clear, actionable 12-month roadmap, broken into 90-day sprints with focused goals, measurable KPIs, and review systems that actually drive progress.
And best of all — it’s built for real-world small business owners, not corporate nonsense.
If you’re ready to get serious about building a business that works with or without you — and commands a higher valuation when the time comes, then let’s talk.
👉 Click here to book a free 1-2-1 with me and see if the 365/90 Accelerator is right for you.