To understand the answers, I think it is necessary to know the business type. These answers are for a small town retail business I purchased several years ago.

I found the business by word of mouth. The owner was ready to retire as he ran this store for 49 years. Not one computer in the place. Only adding machines and paper ledgers. It was not something that I was looking for. But the numbers were good and there was a lot of low hanging fruit in the way of improvements.

I still own the business. I did not purchase it to flip it. Although I have improved the business significantly, I don't think it is a candidate for flipping as a small town retail store has a limited ceiling. IMO, a technology or manufacturing business is a better candidate for flipping as the upside is an easier sell to a potential buyer.

Self employment is a lot of work. So, it helps if you have a background/interest in the business you are buying. Everyone hears about the big payouts when a business is sold. But running a business is a grind and burnout is possible. And that big payout may never come. If you can find joy in running the business and satisfying your customers, then success can be measured by that. I found joy in digitizing and improving the business.

Purchased a CPA practice from an aging practitioner. Went to work for him for a year and a half to be sure I knew about his firm's quality of work, about his clientele, and about his pricing structure and then did the deal.

Bought an RV park that had been at about 15% to 25% occupancy for a few years. Owner hardly ever mowed the place, no longer had internet availability, no laundry on site, and other areas of neglect. I knew of two pretty huge expansions that were going to take place in the area so we bought it for less than what it would have cost to put in just the roads on a 6 acre tract where I was looking to build a park.

Whatever you do or decide to do, don't get in a hurry. Do your due diligence and be prepared to walk away when something no longer meets your criteria that you set going in. No deal is better than a bad deal.

I can offer some different thoughts from the perspective of someone that has participated in hundreds of transactions ...

How did you find the business?

Most buyers self-source deals these days, and what I mean by that is that they do not engage a broker or intermediary to locate a deal for them. I would strongly suggest setting yourself up a profile on BizBuySell, and depending on the size of business you're looking for, Axial is a good tool for larger deals. I would also suggest reaching out to as many M&A firms/business brokers as you can to ask to be put on their distribution lists. Some of them will have more sophisticated systems than others that are capable of sending you details on businesses that fit your specific criteria only if you'd like that.

Was a it a hobby/passion that you wanted to pursue or something unexpected you kind of fell into?

In my experience, the passion most business buyers want to pursue is their passion and desire to be their own boss. It can be dangerous to limit your scope too much and try to identify something you have a passion for. I always recommend to my clients to have an ope. mind to opportunities - as long as they fit the geography and financial scope you need, you never know what you'll find out there. You can always decide not to pursue it, but to not even look at it might cause you to miss a great deal. I represented a buyer once who was adamant about buying a landscaping services business - he had a corporate background, but loved working in his yard and wanted to make that his second career. Long story short, he ended up acquiring a magazine publishing company that he has grown substantially and still owns 10 years later.

Did you purchase to flip or hold long term?

Unless your actual business is flipping business acquisitions, then you should purchase to hold and operate. That's not to say you should buy a business without an exit strategy in mind, but your goal should be to buy, hold, grow and then exit when it makes sense for you. There are "serial entrepreneurs" out there that look specifically for deal they can immediately turn around and flip, but again, that's actually their business. They are not buying businesses with any plan to cash flow them - they are buying them to shine them up and sell them again.

What was a surprise challenge that you may have experienced?

Not exactly an answer to your question, but I can tell you the most common comment I hear from buyers about what surprised them the most is the fact that they are typically working longer and harder hours as a business owner that they did before, but at the same time they feel more fulfilled and satisfied in their lives. It's an interesting dynamic, but it's incredible how many times I've had this said to me over the years.