An Inside Look Into The Business You're Considering

How to Get Expert Information for the Exact Business You’re Thinking of Starting

If you’re thinking about starting a business, there’s one thing that can save you a lot of money, stress, and wasted time:

Real, unfiltered information from people who are already running that exact type of business.

In this guide, you’ll see how to get insider details about a business before you jump in. You’ll learn how to speak with owners who have their businesses for sale, how to reach out to non-competing owners, and how to get advice from professionals and mentors online.

This approach is not sneaky or deceptive. You’re honest about what you’re doing. You keep an open mind. And you may even discover that buying an existing business is better than starting from scratch. For more on that idea, see Buy a Business or Build One From Scratch?

Let’s walk through the steps.

The Key to This Technique

The key to this technique is simple:

Keep an open mind.
Be honest about what you’re looking for.
Respect people’s time and experience.

You’re going to contact business owners who:

Have their business listed for sale, and/or
Own a similar business in another area and won’t see you as direct competition.

You’ll ask questions about their operation, the industry, their customers, their challenges, and their numbers. You are not trying to trick anyone. You’re trying to learn whether this kind of business is truly right for you.

Is This Approach Ethical?

Some people worry that talking to owners of businesses for sale just to “learn” might be unethical. It doesn’t have to be.

Be honest: Let them know you’re exploring whether to buy a business or start one from scratch.
Be open-minded: If the business is a good fit, you may seriously consider buying it.
Respect boundaries: Don’t push for confidential details they’re not comfortable sharing.
Respect their time: Come prepared with questions and keep the conversation focused.

Handled this way, you’re not misleading anyone. You’re simply doing your homework and giving owners a chance to share their experience—sometimes with the bonus that you might become their buyer.

Step 1: Get Clear on What You Want to Learn

Before you contact any owner, get clear on what you actually want to know. For example, you might want insight into:

What a typical day looks like.
How many hours the owner really works.
The kind of customers the business depends on.
The biggest challenges and risks.
The skills and personality needed to succeed.
Rough ranges of revenue, expenses, and profit.
Seasonality and slow periods.

Make a simple list of the topics that matter most to you. That way, when you talk to owners, you’re not just making small talk—you’re gathering useful information you can use later.

Step 2: Build Your Question List

Next, turn those topics into questions. Write them down so you don’t forget anything and so you can ask the same core questions to multiple owners and compare answers.

You can adjust the questions below to fit the industry you’re looking at, but this list will give you a strong starting point.

Questions About the Owner and History

Question 1:

Did you start this business or buy it?

If they bought the business, your next question is how long they’ve had it. If it’s only been a short time, this might be a business purchased to flip for a quick profit. In that case, they may not have the long-term experience you’re hoping to learn from.

Question 2:

How long have you had this business?

This helps you understand how much experience the owner has in this business and this industry.

Question 3:

Why are you selling the business?

There are many possible reasons. A few common ones are:

a) The owner lost interest.

This may mean the business has not been taken care of. It might be run down or have a poor reputation. Now that you’re aware of this, look for signs of neglect and decline.

b) They don’t have the help they need.

If they can’t keep staff, you’ll want to know why. Is it because no one wants that type of job? Is the pay too low? Is the work environment difficult? This could be a sign of deeper problems.

c) The owner has a problem with the business.

Maybe the business depends on long hours, stressful deadlines, or difficult customers. If you can solve or manage those issues, this could still be a good opportunity for you.

d) They want to retire or have other life changes.

This can be a great situation for you. A retiring owner often has years of experience and may be willing to share a lot of what they’ve learned.

Question 4:

Would you ever consider opening a similar business again?

This question can reveal how they truly feel about the business and whether they see long-term potential in the industry.

Questions About Customers and Marketing

Question 5:

How do you get customers, and what types of advertising and marketing do you use?

The answer shows how active they are in marketing and where their customers come from. It can also reveal missed opportunities or advertising channels they haven’t tried.

Question 6:

What are your advertising costs, and how do you measure the return on investment?

This helps you see how aggressive their advertising is and whether they track results. If they say they don’t know the return on investment (ROI), then they may be advertising blindly with no tracking. If the business is doing well despite weak advertising, you might be able to grow profits with better marketing.

Question 7:

Are your customers repeat buyers or mostly one-time customers?

It’s often more expensive to gain a new customer than to keep an existing one. A business built on repeat customers can be more stable and easier to grow.

Question 8:

Are there busy and slow seasons in this business?

Ask when the busy periods are, when things slow down, and how they handle cash flow during slow times. Seasonality can affect everything from staffing to marketing to your own income.

Questions About Operations and Staff

Question 9:

How long has your staff been with you?

Long-term staff can be a good sign. High turnover can point to problems with the job, management, the work environment, or the pay. Ask why employees tend to leave and consider whether you could fix those issues if you took over.

Question 10:

What are the biggest challenges involved in running this business day to day?

This reveals problem areas and opportunities for improvement. Whether you buy the business or start your own, you’ll want to understand these challenges and think about how you would handle them.

Question 11:

What tools, systems, or software do you rely on every day?

This helps you understand how organized the business is. Ask about point-of-sale systems, scheduling tools, accounting software, and anything else that keeps operations running.

Questions About Money and Risk

Question 12:

How much revenue came in over the past six months, and what does a typical month look like?

Revenue is vital to survival, but it’s only part of the picture. Ask how much of that revenue is profit and what the major expenses are. A lot of revenue with very little profit can be a warning sign. So can high profit on very low revenue. Ideally, you want a healthy flow of revenue with a reasonable profit margin.

Question 13:

Are there any lawsuits, legal issues, or regulatory problems I should know about?

If there are legal or regulatory issues, get the basic details. Even if you decide not to buy, you can learn from what went wrong. If you are considering buying, this is an area where you’ll want professional legal advice.

Question 14:

If someone were buying this business, would there be an option to finance part of the purchase through you?

Some owners are willing to accept a down payment and monthly payments with interest instead of full cash up front. Others may not want that responsibility. If the business has debt, one option can be to pay the owner their share and assume the existing debt, if the lender allows it. Any financing arrangement should be reviewed with legal and financial professionals.

I had a friend who couldn’t sell his business. I asked him why he wanted to sell. He said he wanted to start a new business and mainly needed to pay off the business’s debt. I suggested he sell the business with a low down payment and have the buyer assume the debt, with the lender’s approval. He sold it within a week to one of his employees. It turned into a win-win for both sides.

Questions About Fit and Lessons Learned

Question 15:

What do you like the most about this business?

This shows you the rewarding side of the business and the parts the owner enjoys.

Question 16:

If you had to start from scratch, what would you do differently?

This question reveals regrets, missed opportunities, and hard lessons. Take notes. Their mistakes can become your checklist of what to avoid.

Question 17:

What kind of person do you think does well in this business?

Ask about skills, habits, and personality. Then compare their answer to your own strengths and weaknesses. This helps you decide if you’re truly a good match for this line of work.

Question 18:

If you had an extra $10,000 to invest in this business, where would you put it?

This question points directly to opportunities. The answer often reveals where the owner sees the greatest potential for growth or improvement.

Step 3: Find Businesses and Owners to Talk To

Once you have your question list, it’s time to find people to speak with.

Option A: Businesses for Sale

Start by looking for businesses that are already listed for sale. You can:

Check your local newspaper or community publications.
Talk to business brokers and real estate agents who handle commercial listings.
Search online business-for-sale marketplaces.
Ask around in your network. Many sales start with word of mouth.

Make a list of businesses that match or are close to the type of business you want to start. Include basic details such as name, location, contact information, and a few notes.

Option B: Non-Competing Owners

You can also learn a lot from owners who are not selling and won’t see you as a threat. For example:

Owners in other cities or regions.
Owners in a slightly different niche that still serves similar customers.
Owners you meet through industry associations or local business groups.

Because you’re not direct competition, they may be more relaxed and open to sharing their experience.

Step 4: Make Contact the Right Way

When you reach out, being clear and honest goes a long way. Whether you call, email, or meet them in person, your message can be simple:

Tell them you’re thinking about starting or buying a similar business.
Explain that you’re trying to understand whether it’s the right fit for you.
Let them know you have some questions and would appreciate any insight they’re comfortable sharing.
Be upfront if you’re early in the process and not ready to make an offer yet.

You can also offer something in return for their time, such as:

A consulting fee for a focused advice session.
Help in an area where you’re strong (for example, online marketing or technology).
Sharing your own lessons later once you’re up and running.

Not everyone will say yes. That’s normal. Some owners are too busy or just not interested in talking. Expect to hear a few “no” responses on your way to the right people.

Step 5: Conduct the Interview

When you sit down with an owner—whether in person, on a video call, or on the phone—come prepared:

Bring your question list.
Have a notebook or device ready for notes.
Be on time and stay focused.
Let them talk and don’t argue with their opinions.

As they answer, pay attention not just to the words, but also to how they say them. Notice where they:

Light up and get excited.
Sound tired or frustrated.
Become vague or uncomfortable.

Those reactions can tell you as much as the facts. Ask follow-up questions like “Can you give me an example?” or “What happened when you tried that?”

Remember, at this stage you are gathering information. Formal verification of numbers comes later, during due diligence, with the help of professionals.

Step 6: Get Expert Advice Online

You’re not limited to local owners. The internet gives you access to business professionals in almost any industry.

You can search for:

Industry consultants and coaches.
Accountants who specialize in your type of business.
Business owners active on professional networks or in industry forums.
Industry associations and groups that support business owners.

When you contact them:

Be clear about what kind of business you’re looking at.
Explain that you’re in the research stage.
Have specific questions ready so you don’t waste their time.
Offer to pay a reasonable consulting fee when appropriate.

A good conversation with the right professional can save you from making expensive mistakes. In some cases, you may even end up with a mentor who can guide you as you move forward.

Step 7: Look at Franchise Opportunities

Another way to get inside information is to look at franchise opportunities in the industry you’re considering.

Franchise companies often provide:

Details about typical startup costs.
Information on training and support.
Guidelines for marketing and operations.
General information about performance across locations.

Even if you decide not to buy a franchise, the information they provide can help you understand how the business works and what it takes to succeed.

Step 8: Compare What You’ve Learned

After you’ve talked to several owners and professionals, step back and compare your notes. Look for patterns:

What challenges do most owners mention?
What do successful owners seem to have in common?
Where do struggling owners seem to get stuck?
What surprised you the most?

It can help to create a simple table or spreadsheet with columns such as:

Business name
Location
Pros
Cons
Key numbers (only what they were willing to share)
Your overall gut feeling

You’re not just collecting random comments. You’re looking for themes that will help you make a smarter decision.

Step 9: Decide Whether to Buy, Start from Scratch, or Walk Away

By this point, one of three things will usually happen:

You find a business that looks like a good fit and worth pursuing.
You decide you still want to start your own business from scratch—but now with much better information.
You realize this type of business is not right for you, and you walk away before committing time and money.

Any of these outcomes is a win. The goal is not to force yourself into a business. The goal is to find out the truth before you jump in.

Step 10: Perform Proper Due Diligence Before Buying

If you find a business you’re seriously considering buying, the next step is proper due diligence. This is where you:

Review financial statements and tax returns.
Look at leases, contracts, and key agreements.
Check for legal, regulatory, or licensing issues.
Review any significant debts or obligations.
Work with qualified professionals such as accountants and lawyers.

This step is too important to rush. It’s where you verify what you’ve been told and see the full picture. For more on this topic, see Tips for Performing Due Diligence When Buying a Business.

Closing Thoughts

Starting or buying a business is a big decision. It’s easy to fall in love with the idea and ignore the reality. By talking directly to owners, asking smart questions, and listening carefully, you give yourself a major advantage.

You may discover a great business you can take over and grow. Or you may confirm that starting from scratch is better for you. Either way, you’ll have real-world information you wouldn’t have had if you skipped this process.

Your Next Step

Here’s a simple way to move forward:

Make your own question list based on the ideas above.
Pick three to five businesses or owners to contact.
Schedule your first call or visit.

Every conversation you have brings you closer to the truth about the business you’re considering—and helps you decide if it’s the right move for you.