Entrepreneurs over 50: Start with an idea

Entrepreneurs over age 50 are the most likely to succeed with their new business.  Years of experience, combined with more savings, give the midlife business owner an advantage over the twenty-somethings who get most of the media exposure.  It makes sense to create a side hustle to supplement your day job to protect against sudden job loss and the need for more income after retirement.


According to the 2019 Guidant Financial State of Small Business report, baby boomers control 57 percent of America’s small businesses.  The reasons cited for opening a business:

  1. Be my own boss (more men)

  2. Pursue my passion (more women)

  3. Opportunity available

  4. Dissatisfaction with the corporate world

  5. Not ready to retire

Older adults are a growing segment of the US entrepreneurial population.  Individuals ages 55 to 64 have gone from making up 14.8% of new entrepreneurs in 1996 to 25.5% of all new entrepreneurs in 2016. – 2017 Kauffman Index of Startup Activity, Ewing Marion Kauffman Foundation.

The e-commerce platform, Shopify, highlighted nine customers who were over 50 on its blog in 2017.  From food and pet products to luggage tags and adventure lighting, the entrepreneurs set out to solve a problem. “Find a niche that you are really passionate about and don’t be afraid to go after it,” advised Rebecca Wilson.


At 65, Viv Poole started Silver Startups in the United Kingdom to help people in her age group start new businesses.  Her MBA and experience as a business consultant gave her the credentials she needed to be accepted as an expert.  She has an informative blog website with ideas that could also work for people in other countries.


Our primary finding is that successful entrepreneurs are middle-aged, not young… We find no evidence to suggest that founders in their 20s are especially likely to succeed.  Rather, all evidence points to founders being especially successful when starting businesses in middle age or beyond, while young founders appear to be disadvantaged. – Age and High-Growth Entrepreneurship

Where do you look for information and ideas?


Next Avenue

One of my favorite websites, Next Avenue, from Twin Cities PBS, is a primary national resource for information about aging. Its Work and Business section has current articles about starting a business with how-tos and success stories.


Chris Guillebeau

I’ve written about Chris Guillebeau’s podcast, Side Hustle School, several times.  Every day, there’s another interesting story about someone’s business.  His newest book is filled with 100 side hustle stories with full-color photos and links (not necessarily people over 50).

Three stories from Chris Guillebeau’s 100 Side Hustles:

A survivor of an abusive marriage, Teresa Greenway was a caregiver to her disabled son, had several part-time jobs and survived on food stamps when she learned about the online learning platform, Udemy.  Having taught herself to bake sourdough bread years earlier, she knew she had a skill that could be taught online.  Teresa recorded her videos in a garage and prepared an online course, Northwest Sourdough, in four months.  After her first month brought in $1000 in sales, she generated $178,000 in sales the first two years of her business.


James Ashenhurst created a blog about organic chemistry for college students.  He tutored students individually until he was able to figure out what they needed the most and how to deliver it to more students.  He wrote an e-book called The Reagent Guide and was surprised by how well it sold.  This led to other products, and his website is now ranked tenth in online chemistry sites with 60 million page views since 2010.  He now has an annual six-figure income from his business.


A carpenter in Canada couldn’t find quality souvenir patches to bring back from his travels, so he found a designer and a manufacturer to create his own.  He wanted a 1920s steamer trunk vibe, according to his website.  With a $1500 investment, he now has an online store, Vagabond Heart, offering patches, stickers, mugs and beach towels celebrating destinations all over the world.  There is also a collection for national parks.


Chris Guillebeau offers advice throughout the book with action plans based on that entrepreneur’s story and critical factors in their successes.  He describes a side hustle as something you have control over, different than your day job, that becomes an asset you build.  It is not a second job, hobby, or energy/money drain.


Pat Flynn 

Pat Flynn, podcaster and course creator, wrote a book called Will It Fly?: How to Test Your Next Business Idea, So You Don’t Waste Time and Money to help people evaluate ideas for new businesses and products.  He suggests asking yourself, “What is my unfair advantage?” then emailing ten friends/colleagues to get their opinions on your superpower.


Mindmeister (or Freemind or Mindly.)

Pat interviewed entrepreneur John Saddington, who advised writing down your idea and tell lots of people about it to get their reaction.  Pat wondered if they would copy the idea.  “But here’s the difference between you and the next person on the street who has a great idea – if you’re committed and you love the idea, you will actually see it to completion.  Most people never execute on their ideas because they just never execute.”



What’s your big idea?

Brainstorm ideas by observing people’s behaviors, identify a problem and solution and consider the five W’s (who, what, when, where, and why) of your ideal customer’s spending.  The most important thing to consider is what you already know and how you can use that to start a side hustle.  You don’t need to make a million dollars to change your life.  Start with something small that hopefully doesn’t need a substantial investment but that you enjoy doing.

#entrepreneurship #over50 #sidehustle

Fixed Purpose

Contact:  diane@fixedpurpose.com

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