5 Mistakes Most Boomer Business Owners Don’t Realize They’re Making

The following guest post was written by Ryan Levesque.


There’s a lot of business advice out there. And somehow, boomer business owners are still making these 5 mistakes. Here are the lessons it took me 72 months to realize…and the one thing that will change the way you look at your business.


No matter how old you are when you start your first business, whether it’s 25 or 75 or anywhere in between, you’re going to make some mistakes. Let’s face it, mistakes are a part of life. In fact, sometimes they’re one of the best parts, because they allow us to learn and improve, and they give us the experience that’s so valuable.

In my previous life as a corporate wage slave (working for AIG), it took me a while to realize that what I really wanted was to be an entrepreneur, building my own business, not someone else’s, and leaving a legacy that would make a difference in people’s lives.

It took me a few years and a lot of setbacks along the way, including a near-death experience that changed my life. When my son was born, I found myself exhausted all the time, and losing weight. I chalked it up to being a new dad and a busy business owner, but when I applied for life insurance and it came back DENIED, I went in to see the doctor.

The doctor took a look at my blood tests and said, “You need to go to the emergency room, NOW.”

From there, things spiraled into my spending a week in the ICU, with my organs shutting down, getting pumped full of all kinds of drugs and fluids. It turns out I had undiagnosed Type 1 Juvenile diabetes, and the doctors said if I had waited another 24 hours, it’s possible I could have died.

One thing I took away from that health crisis (which I talk about more in my book, Ask), is that life is short. If you’re working for someone else and there’s something else you’d rather be doing…go for it.

If you’re just starting your business, good for you. That shows that you’ve thought long and hard about what you really want to be doing, and you’re going after it. That takes guts.

But as I said before, part of the process of starting a business is making mistakes. I’ve made lots of them. And from each mistake, I learned an incredibly valuable lesson that helped take my business from $500 a month to $5 million a year.

And while every mistake is an opportunity to change, to innovate, and to improve, they can be costly for you and your business. So I can understand if you’d rather not make them in the first place.

I’m sharing this with you in the hopes that you’ll find something valuable that will help you right now.

Ready? Let’s dive in.


1) Forgetting to solve a PROBLEM

The Mistake: People buy a product not because of the product, but because it helps them solve a PROBLEM. You could have the greatest product since sliced bread, but if it doesn’t solve an urgent problem that people are having, they won’t buy.

The Fix: Start with the problem first, and then develop your product to solve that problem.

So how do you know if your product solves a problem? How do you know if that problem is URGENT for a big enough market?

Well, one of the first markets we entered was teaching people how to make Scrabble Tile jewelry.  We entered the market because my wife struggled to figure out how to make the jewelry, and we we found many other people online had the same problem. So we created a tutorial that taught people how to make the jewelry, and we grew that business from $0 to about $9,000 a month within 9 months. Because this was one of the first markets we tried, we made the mistake of choosing something that wasn’t evergreen. Scrabble Tile jewelry, like all passing fads, soon became passe.

The problem may have been urgent, but it was temporary. You want to look for a problem that people are always going to have. This experience led me to make sure that “evergreen potential” was at the top of the list for any future markets I chose to enter.


2) Looking at the WRONG Answers (Focusing on the wrong data)

Once you identify the problem that you want to solve, the next step is to ASK people what their single biggest challenge or frustration is related to that problem. This will give you insight and feedback on just how urgent this problem is for people, in other words, how responsive the market is.

A great way to discover problems in your market is to do what I call a Deep Dive Survey. This is the first survey I talk about in my book Ask. It’s based on asking people not what they want, but rather what they don’t want. For example, a common question I like to use in this survey is “What’s the biggest obstacle/challenge you’re having right now with X.”

The Mistake: If people give you short simple answers, it’s unlikely to be a problem they’ll spend money to solve. Pay too much attention to these responses, or give them too much weight, and you may end up entering a market that’s not responsive enough.

The Fix: If they give you long, detailed passionate answers then there’s a good chance they WILL spend money.  When you do a Deep Dive Survey, you want to look at the percentage of people that provide long, detailed, passionate answers. We call those the hyper-responsives, and those are the people whose answers you care about. They are desperate to find solutions to their problems, and therefore will be more likely to buy a product that offers them that solution. So your first step is to survey your market and pay close attention to the responses. I talk about the full process for how to do this “Deep Dive Survey” in my book.

The results look something like this. You can see the columns on the right give each response a score based in part on how long the responses are, and then I use a specific formula to calculate if this prospect is a hyper-responsive or not.  

Once you have your results, and you know the problems your market is having, how do you respond to them?

Many business owners make the following mistake:


3) Taking a One-Size-Fits-All Approach

The Mistake: Do you really know who your market is? Are they men or women? What’s the average age? What is their biggest challenge? What’s the most painful thing for them? What do they respond to?

The biggest mistake people tend to make here is thinking that they know who their market is without having the data to back it up.

The Fix: Once you complete a Deep Dive Survey, you have the answers to these questions right in front of you. As you read through the responses, take note of the 3-5 most common CATEGORIES or “buckets’ of responses.  Instead of taking a “one-size fits all” approach, focus on addressing each of these buckets differently.  

For example, another market we’re in is home water filters.  People filter their drinking water for different reasons.  Some people care about taste, some about purity, and some people do it to save money. So we identify what BUCKET someone falls into by asking, and address their unique needs. And we were able to do this based on the data from the Deep Dive Survey.


4) Lacking Feedback Early and Often

The Mistake: Many business owners see disappointing sales and they have no idea what went wrong. Was it the offer? The price point? The product itself? It can seem overwhelming to try to fix something when you’re not sure where the problem lies. That’s because they are missing golden opportunities to ask for feedback from people who didn’t buy.

The Fix: You want to know WHY they haven’t bought, so that you can see what you’re missing and answer these objections. For example, in one of our markets we teach people how to improve their memory.  We originally developed a series of online courses but by ASKing people why they didn’t buy, people told us being online was too distracting.  So we converted the courses into physical workbooks, told people about it, and sales went through the roof.


5) Failing to Course Correct (Until You Find the Answers)

The Mistake: Sometimes, it can be tempting to wait for something to be perfect before putting it out there. And as a business owner, to say, “I need to learn more before I really start something.” This kind of thinking can paralyze you and keep you from taking action.

The Fix: Just DO It and tweak later. In the Scrabble tile market, the water filter market, the memory market – and the 23 markets we’ve entered, we’ve always had to tweak. It’s not about getting it perfect, it’s about getting it going.  And the good news is, anybody can follow the ASK formula I reveal in the book to start and grow their business.  When it comes to starting, there’s no better time to start, than today.

And if you’re wondering why I talk so much about ASKING your prospects and customers, it’s because I built my business on perfecting this model of customized marketing for online businesses.

This is all part of the formula that I reveal in detail in my #1 National Best-Selling book, Ask. The book describes the 4 surveys that I use, each with a different purpose, and it also describes the amazing results this process has had.

If you’d like to learn more about the Ask Formula, you can click here to get a free copy (just pay $4.95 shipping and handling.)

This post was written by Ryan Levesque, the #1 National Best-Selling author of the book, Ask.  The Ask Formula has been used in multi-million dollar businesses in 23 industries to generate $100 million in sales. He and his team offer training, consulting, and implementation services for entrepreneurs and businesses at all levels.

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  • http://www.ryanlevesque.net Ryan Levesque

    Thanks so much for the opportunity, Charlie 🙂

    • Charlie Poznek

      Many thanks to you for your great work, Ryan!

  • ajaykjhaa

    As usual, a post worth reading.

    Loved to read it till end and came to learn a lot from this.

    Thanks for sharing such a great info.

    Lots of ideas.Thanks for increasing our knowledge.


    Keep sharing. – Brahma Kumaris Songs