Retirement Answer Man

On this episode, we explore the aspect of mindset and explore the question: What are some of the mindset attributes of a successful entrepreneur? Mindset is a huge hurdle for so many entrepreneurs. You need to get into the mindset right before you ever consider entrepreneurship. At this stage in life, you don’t have the time to make up for any mistakes the way that you would if you were in your 20s. This is your one shot at becoming an entrepreneur, so you must make the most of it. If you are considering entrepreneurship in retirement you definitely don’t want to miss this episode to hear how you can adjust your mindset for success.

What are some bad reasons to start a business?

You need to think about whether you are starting a business for the right reasons. Just because you can start a business doesn’t mean that you should. If you are planning to open a business simply because you need a change, then you need to rethink. Starting a business isn’t a great way to run away from a bad job. This mindset won’t set you up for success. Boredom is another bad reason to become an entrepreneur. There are much less expensive ways to fill your time. Are you starting a business simply because you have a good idea? Well, I have bad news for you, ideas are the easiest part of entrepreneurship. Make sure you listen to this episode if you are thinking of starting a business.

Money won’t solve mindset problems

Becoming an entrepreneur in your 50s and 60s is much different than in your 20s. Most people have more money at this time in their lives than they have ever had before. Just because you have the money doesn’t mean you should throw it all at your new business venture. Some people get caught up in looking the ‘right’ part. They spend too much money on all the shiny things that they think they need when just starting out. The truth is you need to bootstrap as much as possible when beginning a new business venture. That way if you fail, you will fail cheaply. Listen to this episode to hear why having more money can actually lead to the wrong money mindset.

What are some mindsets of unsuccessful entrepreneurs?

There are many reasons that most new businesses fail. The biggest reason is the business owner has the wrong mindset. Most new business owners do not have the right mindset to create a successful business. If you are becoming an entrepreneur for the first time in your 50s or 60s then you must step away from the employee mindset and switch gears to that of a successful entrepreneur. Unsuccessful entrepreneurs often get stuck in the same routines. They are unable to pivot when something doesn’t work out. Listen to this episode of Retirement Answer Man to hear what kind of mindset it takes to become a successful entrepreneur.

How do successful entrepreneurs think?

Successful entrepreneurs come from many different walks of life, but successful ones share similar mindsets. A successful entrepreneur is action-oriented. When there is a problem with their business they don’t sit around pondering the situation. They are agile; after taking action a successful entrepreneur can quickly adjust to any situation and pivot as needed. Successful entrepreneurs are overly optimistic, yet always worried about what will happen next. Do you have the mindset needed to become a successful entrepreneur? Listen to this episode of Retirement Answer Man to find out.



  • [3:11] What are some of the bad reasons to start a business?
  • [12:10] What are some bad mindsets for entrepreneurship?
  • [13:43] The curse of capital
  • [14:41] You can stick to your dreams too long


  • [16:57] Mindset attributes of a successful entrepreneurs
  • [18:11] Be an optimist, yet be scared


  • [27:58] Watch The Greatest Snowman movie


Resources Mentioned In This Episode

The Greatest Showman

The Retirement Manifesto Blog

BOOK - EMyth Revisited by Michael E. Gerber

Roger’s YouTube Channel - Roger That

BOOK - Rock Retirement  by Roger Whitney

Ask Roger a question

Work with Roger

3-video Series: 5 Minute Retirement Makeover

Roger’s Retirement Learning Center

The Retirement Answer Man Facebook Page

Intro music by

Direct download: RAM225.mp3
Category:general -- posted at: 6:00am CDT