Best Businesses to Start Over 50

When we were around 50, we knew we wanted to start a business, but didn’t have any idea what kind to business to start.  

The best businesses to start over 50 are businesses that will help you reach your life and financial goals whether that includes building wealth, creating new income sources before retirement or both. 

After seriously considering buying a local business over 15 years ago, and deciding to start several  online businesses, instead, that ended up supporting us into early retirement, I’ll share what we learned about the best businesses to start later in life.   

Options for Businesses to Start after 50 

Every business expert promotes what they know. Here’s what I mean.  

Ask a real estate expert the best business to start after 50 and you will unequivocally hear the best business to start is real estate business 

Ask a small business franchise consultant the best business to start over 50 and you will unequivocally hear the best business to start is a franchise.  

Ask an online business consultant the best business to start after age 50 and you will unequivocally hear the best business to start is an online business. 

And the list goes on and on. The truth is that the best businesses for you to start over 50 are the ones that meet your needs and desires, period.  

So start with your lifestyle and financial goals, and then find the expert or consultant to help you implement the steps to start your business.  

We spent a couple of years just deciding what kind of business to start because of the convincing information that is out there based on who is promoting whatAnd we followed one guru down the wrong trail that set us back.  

In that process, we learned a lot, however, about the best kind businesses to meet our specific life and financial goals. The best starting place, we later realizedwas defining those goals from within the context of our own overall wealth plan.  

In this post, I’ll touch on the types of businesses we considered, why we ruled each business model or pursued it, and, most importantly, what really did and did not work. 

Some small businesses we pursued were outright failures. Others were successful. I remember how hard it was to decide on the best business to start after 50 because you have reached the age where financial mistakes are hard to overcome.   

The types of businesses we researched and considered were: 

  • An existing local movie eatery business 
  • A local retail liquidation business with a national infrastructure 
  • franchise based business 
  • Angel investing in several businesses (which we did) 
  • Various types of online businesses (which we did) 
  • Real estate rental business (which we did) 
  • Options trading (which we do) 
  • Consulting business (which we did on a limited basis, more below) 

So as you can see, we’ve been immersed in various types of very small businesses for years. I still remember how confused we were starting out, though.  

Factors for the Best Businesses After 50 

Here are the things to consider with each business.  

Business Financial Goals 

The financial goals for your business are one of the most important factors, if not the most important factor. There can be several financial goals for your business, and the various goals can overlap.  

In general, small business owners tend to think too small as far as financial results.  


Extra income is the goal for most people who start businesses after age 50. After age 50 in particular, small business income can allow someone to put aside extra retirement savings or provide money for lifestyle indulgences previously forgone for the sake of saving more.  

Once retired, a small business that generates $2,000 income a month is like having an additional $600,000 of savings for a retiree using the 4% retirement withdrawal rule for retirement “income” 

For a couple, this is only an extra $1,000 a month income.  

Similarly, income of $3,350 a month is like having over a million dollars extra in retirement savings.  

Granted, you may not want to continue having a small business in your 70’s or 80’s, but you may. 

And think of the impact generating extra income like this can have on your overall financial retirement plan given these numbers!   

Capital Gains from Small Businesses 

A capital gain occurs when you sell an asset at a higher price than the cost to buy it or build it.  

Capital gains are associated with building wealth since you get a large amount of money at once vs the steady flow of an income stream 

Many businesses can be sold for capital gains, especially when they are built with this in mind 

Assets That Generate No Income 

Many small businesses focus only on capital gains while forgoing income along the way. An example is a content based website with the plan to run ads once traffic gets to 100,000 page views a month. It will probably have little or no income for the first six to eighteen months or so (unless ads are purchased).  

Income Generating Assets 

Some businesses generate income during the asset building phase.  

An example would be to add a revenue generating aspect to the website. This could be a service, such as consulting or website building, for example.  

Income could also come from selling a digital product, like a course, or revenue could come from selling physical products (such as pillows), or being an affiliate for any of these.  

The best place to start assessing the best business to start after age 50 is with your financial goals, more than ever. Add a clear time frame after you define whether you want to generate income, build wealth from capital gains or both.  

Begin with the end in mind to expedite the journey to success in your business plan.  

Capital Needed to Start a Business 

The next financial factor to assess the best business to start for you personally will be your capital. In fact, capital, and income vs wealth building, are close contenders for first place.  

Some businesses cost hundreds of thousands to build while others cost less than $25.  

Buying a franchise can easily cost a million dollars or more. Starting an online business that reaches a global market can cost $10 for website hosting 

The question, then, is how much money do you want to allocate to your new business? Knowing this will quickly eliminate many business models that don’t fit into your capital decision.  

For example, we wanted to buy a local business after Larry, my husband, first entered early retirement. After seeing that the amount of capital that we would need to commit to obtain financing, we dropped to the next level of capital intensity, real estate rentals.  

A few years later, we decided to start online businesses since there was no capital requirement and the model appealed to our lifestyle desires.  


The older we get, the less risk we want to take. I think this makes sense for everyone since you have less time to recover from mistakes.  

Financial Risk 

Risk is intertwined with the capital you need to use to start a business, or the capital that is at risk if you fail.  

For example, the financing required to buy the two local small businesses we seriously considered buying 15 years ago demanded our entire savings be used as collateral.  

This meant if we failed at the business, we would loose everything. I was in my 40’s and Larry was in his 50’s. We had two sons in their early teens. There was no way we wanted this risk 

This knowledge made it easy to quickly move on to our next income generating idea of real estate rentals. The purchase price was smaller, and we could leverage with partial financing while structuring positive cash flow.  

So, it generated income while it was also a wealth building asset since we bought below market value and it had other opportunities to increase in value which played out in the years since then.  

Businesses That Are Capital Intensive 

Many people over 50, like us, consider local businesses first since we didn’t grow up with as much technology as the younger generations.  

Examples of businesses that require very high capital are: 

  • Franchises 
  • Local existing businesses 
  • Brick and mortar stores and businesses, such as restaurants and boutiques 

Businesses That Require Little Capital 

Fortunately, there are more small businesses than ever before in time that require little or no capital to start. These include: 

  • Consulting Businesses 
  • Life Coaching 
  • Executive Coaching 
  • Website Content Businesses 
  • Many Service Based Businesses 

Time Risk  

Like financial risk, time risk becomes more important as we get older. One thing I have learned that few entrepreneurs admit is that most small business owners fail several times before succeeding.  

For this reason, it’s important to be able to test a business idea quickly while at the same time sticking with it long enough to give it a fair trial 


Taxes are the last financial consideration. Fortunately, when handled correctly, most small businesses have tax benefits. This is because tax rules were established to support and promote small business development.  

Having a profitable small business with tax benefits helps both sides of the cash flow equation; the expense side and the income side. This can have a dynamic impact on building wealth.   


What lifestyle do you want to have in relation to your business? Are you adding work to full employment, wanting part time work, or passive income as much as possible so you can play more golf? 

There’s no right or wrong. Just define what you want and go from there.  

Blogs and similar online businesses have become so common that there is an entire category of businesses called “lifestyle business”. A lifestyle business enables the owner to work when, where and how they want.  

While “startups” and more experienced entrepreneurs would disagree, I think the lines are blurred between a lifestyle business and other small business models simply because with the internet, many businesses allow the owners to work when and how they want.  

Not only this, but other income sources can stem from lifestyle businesses should you choose. For example, a nutrition blogger can add in affiliate sales or online training. 

Substantiating my standpoint is JoAnna Gaines’ blog which grew to a multi-faceted empire.  

This is just one example of a website among thousands that began as a lifestyle business that went on become a multi million dollar business.     

Work Hours 

Like many who start a small business, do you want to be able to work ten hours or less in it because you are employed elsewhere full time? Or are you retired and you know you want to work about 30 hours a week from anywhere because you have other obligations? 

Or are you available to work 50 hours a week and enjoy working as long as you can set your own hours? 

Or maybe you’re still married to an 8 to 5 routine Monday through Friday at an office location? 

You get to pick this time around. So define the lifestyle you want. Make it a priority.   


The ability to travel while keeping your business running is an important lifestyle factor for assessing the best business to start later in life. Given the enthusiasm of grand-parenting, the ability to travel as a business owner is an important factor for many people over 50.  

Many people also now have more than one home in different locations, often renting out one while living at the other for half the year. 

And many people are ready to travel more after family obligations lessen later in life.   

If any of these locale factors apply to you, the ability to travel will help you assess the best type of business to start later in life since not all businesses can be easily run from afar.   

Work Required 

When assessing the best business to start many people forget to think about the actual work they will be doing on a day to day basis.  

Will you be: 

  • Managing multiple clients? 
  • Doing service based work? 
  • Managing a team?  
  • Doing technology? 

The list is endless so I’ll stop here but the main thing to clarify is what you will need to do in the business, and if this is something you enjoy 

Work Location 

Whether a business demands you work at a certain or multiple locations vs home or from anywhere you want is a huge lifestyle factor.  

For example if you do executive coaching for multiple clients in many cities or even countries, you will probably need to work from their offices. On the other hand, many types of businesses can be run virtually, such as online businesses or remote services.  

If you like to work in your pj’s some days, like me, you’ll probably want work location flexibility.   

Ability to Delegate 

Most people starting a small business aren’t aware of the need and ability to delegate tasks. Again, some models demand that you do almost everything, as in the executive coaching business.  

On the other hand, something like a content or publishing based website can be almost completely delegated.  This ties back to the amount of capital you’re planning to put into the business since delegation costs money.  


Enjoyment of the work or industry is a particularly important factor in assessing the best business to start over 50. Perhaps this is because many of us have waited almost a lifetime to do what we want to do. The thought of delaying doing something we enjoy becomes less tolerable as we age, unless we have lost touch with our dreams.  

Leveraging with Correlation 

Some businesses relate to other businesses. When this happens, you can leverage time and money. This is something you can plan to do.  

Aligns with Other Businesses 

For example, our real estate rental business has little to do with our online businesses. But our three online businesses require related skills, software, technology and outsourcing.   

When you have more than one business that requires the same elements, you can leverage time, products and outsourcing. This increases efficiencies.  

Aligns with Hobbies  

Some businesses can leverage what you are already doing. For example, I am a woman over 50 and have been for many years now. I have knowledge about the lifestyle of a woman over 50 

Similarly, I invest, and I write about investing a 

My husband, Larry, was a professional options trader, so he teaches people how to trade options at 

These are things we are already doing or have done for years, allowing us to leverage what we know in both our lives and our businesses.  

And since these businesses are all online, we use the same technology, team and skills to run them.      

Best Businesses to Start Over 50 Summary 

Only you can decide the best business for you to start later in life based on what you want. Grab your journal and address each of these important factors to clarify what type of business is best for you.  

Leave a Comment

Your email address will not be published. Required fields are marked *