🏈 THE SIDELINE

When I started writing for small business owners, I thought the job was clear.

Help them prepare for an exit. Talk about valuation, buyers, deal structure, and what makes a business sellable.

But after a year of writing, conversations, and replies, it became obvious.

Exit prep wasn't the real issue. Business owners needed to understand how they operate and what to fix. That's why we became The Sideline.

👋 Hello! I’m Kinza, and I spend an unreasonable amount of time studying how owner-operated businesses actually scale and exit.

If you’re an owner-operator, meaning you touch sales, ops, people, money, and strategy, this newsletter is for you. Each week, I share useful links and short notes that help owners move from “the business needs me” to “the business can run without me.”

I interviewed 643 business owners.

Most were operating like quarterbacks instead of head coaches.

Putting out fires all day.

When you’re that deep in the action, you lose the field.

Want to see where you stand? Take the free quiz here: 👉 Ownerquiz.com 

Let’s dive in.

FROM THE FILM ROOM
🌎 Expand Your Thinking

• 4 questions business buyers ask themselves when acquiring (Link)

• When clients say price is “too expensive,” it’s rarely about price (Link)

• Change fails when owners use the wrong tool. HBR breaks it down (Link)

• ‘AI roll-up’ investors think services firms can trade more like software companies. Here’s what they get wrong (Link)

• Wondering what investors define as “good market dynamics”? (Link)

  

  Link

🛠️ Tool Stack of the Week

• 8% of AI users have created more work for themselves (Link)

• Shortwave automates the inbox by organizing, scheduling, writing, and editing emails. (Link)

• Willow turns audio into text, so chatty users can speak, instead of type, their emails and other messages. (Link)

• MindMap AI creates brainstorming visualizations to help users externalize and organize thoughts and plans. (Link)

• Akiflow is an AI-powered personal assistant that manages users’ calendars. (Link)

• Otter takes notes during meetings to create transcriptions and summaries. (Link)

• Notion integrated AI into its work-organizing platform. (Also, check out some of the best free templates.) (Link)

• ChatGPT is an obvious pick. This Reddit thread details how to turn the AI chatbot into a personal productivity coach. (Link)

• Below is a prompt I use to help business owners understand their operations and identify necessary changes. It's based on a framework from my experience with hundreds of owners. Most operate like quarterbacks unknowingly. Just copy, paste, and let your AI interview you to start the conversation.

```
You are an expert in business operations and exit preparation, specializing in helping business owners understand how they operate and what needs to change.

Your approach is built on one core principle: **independence**.

---

### The Independence Principle

Buyers and scalability value business independence more than owner involvement.

- ❌ DEPENDENT: "I personally handle all client relationships"
- ✅ INDEPENDENT: "We have a documented sales process anyone can follow"

Independent operations create optionality. You can scale, step back, or sell. Dependent operations trap you.

---

### The Four Operating Styles

| Persona | What It Looks Like |
|---------|-------------------|
| **Head Coach** | Business runs by design. Systems handle decisions. Removed from daily operations. |
| **Offensive Coordinator** | Sets strategy but still deeply involved in execution. Team needs direction. |
| **Quarterback** | Makes every call. Touches every important play. Nothing moves without them. |
| **Linebacker** | Reactive firefighting mode. Steps in to tackle problems constantly. |

---

### The Two Week Test

> **"If you left for two weeks with no phone or email, what would break?"**

- ✅ Nothing critical → Head Coach
- ⚠️ Strategy stalls → Offensive Coordinator  
- ❌ Everything stops → Quarterback
- ❌ Chaos erupts → Linebacker

---

## YOUR PROCESS

**Step 1: Interview the User**

Ask these questions ONE AT A TIME (wait for each response):

1. **Business Overview:** "What type of business do you run? Industry, size (revenue/employees), and years operating?"
2. **Daily Role:** "Walk me through a typical week. What can't happen without you?"
3. **Team Structure:** "Who works for you? When do they need your approval?"
4. **Systems & Documentation:** "What processes are documented? What happens when you're unavailable?"
5. **Future Vision:** "Where do you want to be in 2-3 years?"

Confirm all inputs before proceeding.

**Step 2: Generate Assessment**

After gathering context, deliver:

1. **Operating Style** — Which persona with specific evidence
2. **Top 3 Dependencies** — What keeps them from Head Coach status
3. **Quick Wins** — 3 things to document this month
4. **Path to Head Coach** — Prioritized steps
5. **Exit Readiness Score** — 0-10 rating with what needs to change

---

**Begin by introducing yourself briefly, then ask the first interview question.**
```

BUILDING A WINNING PROGRAM
📈 3 Lessons About Scale

Here's what separates businesses that scale vs. plateau:

1. Scale comes from removing the owner, not adding resources.

Most owners try to scale by hiring more people or buying more tools. The businesses that actually scale remove the owner from routine decisions. When the owner stops being the default answer, the business starts moving on its own.

Example: If your team asks "What should we charge this client?" every time, you're the bottleneck. Write down your pricing structure once, and they can quote without you.

2. Simple rules scale better than smart people.

Hiring capable people doesn't help if they still need approval to act. The businesses that scale write down simple rules for common decisions. That clarity matters more than talent. People move faster when they know the boundaries.

Example: "Any refund under $500 gets approved immediately, no questions asked" moves faster than "check with me first." Your team makes the call, and customers get answers in minutes instead of days.

3. Growth exposes how the owner operates.

Scaling doesn't create problems...it reveals them. If an owner steps in to fix everything, growth leads to chaos. If an owner avoids risk, growth stagnates. Scale shows the owner's habits clearly and progress comes from adjusting how the owner operates, not from pushing harder.

Example: When you go from 5 to 15 employees, being the only person who can approve purchases doesn't just slow things down. It stops them completely. The problem isn't growth…it’s that you never built approval limits.

THE FOURTH QUARTER
💰 3 Lessons About Exit

Here's what most owners get wrong about exits:

1. Buyers buy independence, not effort.

Buyers aren't impressed by how hard you work. They care whether the business runs without you. If results depend on your presence, the business looks risky, and risk lowers value.

Example: A buyer doesn't care that you personally close every deal. They care that your sales process is documented so anyone can follow it. Your hustle is admirable, but it’s not transferable.

2. Exit readiness is built long before selling.

Exit preparation isn't something you do at the end. It's built through daily decisions. Clear ownership, repeatable processes, and decision rules make a business easier to transfer. Waiting until you want to sell is too late.

Example: When you document how to onboard a client today, you're not just training your team. You're creating an asset a buyer can use tomorrow. Every process you write down adds value whether you sell or not.

3. Exit is about options, not leaving.

Most owners don't want to sell tomorrow. They want choice. A business that runs without you gives options to scale, hold, or sell. Exit readiness is control and sale is just one possible outcome.

Example: Build a business that runs for two weeks without you, and suddenly you can take a real vacation, hire a CEO, or field offers from buyers. Same business, completely different life.

FINAL WHISTLE
Great businesses are built on proven systems, not constant “innovation.”

When you professionalize ops, you create the foundation for scale.

Scale gives you choices.

And if you choose to exit, it should be worth your while.

Want to see where you stand as an owner?

Take the free quiz at 👉 Ownerquiz.com 

Cheering for you,
Kinza