How to Become a Gig Entrepreneur

By Lynne Beverly Strang

Jim Glay, Owner of Crash Boom Bam

After Jim Glay abruptly lost his sales manager position at age 59, he spent a year looking for another job. When no prospects materialized, he decided to go another route: turning his life-long passion – playing the drums – into a business.

Today, Glay is the CEO of Crash Boom Bam, where he sells pieces from his expansive collection of vintage 1960s drum sets through an online store. He also brokers sales for other drum collectors and performs as a drummer a few times a week with rock and jazz groups.

Glay was among the “gig entrepreneurs” – i.e., people who earn an income by turning skills and talents into gigs or freelance work — featured at Boomer Boot Camp, a July 2017 workshop sponsored by BoomerWorks and AARP Virginia.

I had never heard of the term “gig entrepreneur” before the workshop. But as a freelance writer and an author, I fit the description. So I joined the mostly 50-and-older professionals who filled a Northern Virginia church meeting room to hear the ins and outs of finding gig work.

Changing demographics, risk-averse employers and a trend toward outsourcing are factors behind the tighter job market for boomers, said Purposeful Hire’s Shira Harrington. As a result, interest in gig entrepreneurship has never been higher, as evident by the strong turnout for the boot camp.

Lanes and Tribe

For those interested in gig work, the first step, said Harrington, is to define your “lanes” (professional skills that can be repurposed into short-term gigs or a long-term business) and “tribe” (the industry, mission or sector where you can solve challenges and have an established network).

Harrington outlined three ways to enter the gig market: FCO or fast-cash options (focus groups, Uber, AirBnB, etc.) for those who need money in a hurry; on-demand gig work (project-based assignments such as freelance writing or event planning); and small business ownership.

Participants in the July ’17 boomer boot camp

How much money can you make from gig work?  It depends upon you and what you’re offering.

Gig entrepreneurs have unlimited earning potential but “you have to get into the frame of mind that says it is possible,” said Harrington.

In addition, an unfulfilled need has to exist no matter which route you choose. “People are only going to hire if you can solve an urgent problem,” she said.

No More Gold Watch

Micro-businesses with five or fewer employees are now among the top providers of employment, noted Angela Heath, founder of TKC Incorporated. “We, as baby boomers, have to think very differently,” she added. “There is no more gold watch.”

“You cannot live to be 45-plus and not have something to offer the economy.” — Angela Heath, founder of TKC Incorporated

Like Harrington, Heath believes the future is bright for gig entrepreneurs. “You cannot live to be 45-plus and not have something to offer the economy,” she said.

From Heath’s experience, people often overlook everyday skills – such as organizing, painting or home decorating – that have value and can be converted into a business. “With technology, the doors are swung wide open,” she said.

Still, first-time gig entrepreneurs may find it challenging to get a foot in the door. “When it comes to gig work, you have to be tightly focused at the beginning,” said Bizstarters’ Jeff Williams, whose clients include Glay of Crash Boom Bam.

Once people know you’re capable, they’re likely to come back to you for other jobs since it’s time consuming to find good help, he added.

Williams pointed to himself as an example. “I have probably picked up one-third of the income I enjoy today from work I never expected to do,” he said.

Getting Started

If gig entrepreneurship appeals to you, note these five things that Heath says you’ll need to get started:

1) Answers for your questions – Reach out to organizations or people who can provide technical information about your industry. Two places to look: Trade associations and LinkedIn.

2) A way to manage fear and doubt – These emotions are inevitable when you start a business. To cope, join a supportive community, do research and product testing, get feedback on your idea and analyze/prepare for worst-case scenarios.

3) Accountability – Line up someone who will keep you focused on your top priorities. A family member, a business partner or a marketing consultant may be candidates for this role.

4) Support – Find others to do the aspects of your gig work that you can’t, or don’t, want to do. Bartering can be a great way to exchange needed services.

5) A willingness to ask, seek and knock – Be prepared to market yourself and make “an ask.” And you can’t ask just one time. As Heath put it, “If you don’t bring it, somebody else will.”

Here are a few resources that might be helpful:

Articles20 Gig Websites; Top 10 Gig Websites.

Books – The Gig Economy by Diane Mulcaly; The Gig Solution: How Boomers Can Earn Executive Fees Doing Project Work by Spunk Burke; What’s Next? Follow Your Passion and Find Your Dream Job by Kerry Hannon.

Coaching – Williams and Heath offer coaching programs especially for older entrepreneurs. BizStarters’ Start Your Business NOW! e-course, normally $199, is $99 for a limited time. Limit-less: Uncover the True You and Profit, TKC Incorporated’s five-session live course, runs July 26-August 23, 2017.

Organizations – BoomerWorks,,, SCORE and the U.S. Small Business Administration offer various types of information – such as research, downloads, webinars and templates – for aspiring and new entrepreneurs.

The bottom line? Gig entrepreneurship can be ideal if you want independence, flexibility and an income without certain responsibilities (such a payroll) associated with other forms of entrepreneurship. Like any business owner, you’ll need focus, tenacity, a plan and a willingness to do without.

But you’ll be working for yourself.  And that’s a great feeling.

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How to Enjoy Summer – And Grow as an Entrepreneur

Summer means barbecues, pool parties, family reunions, beach trips and other vacations. Are any of these activities realistic if you’re an entrepreneur strapped for time?

The answer is yes – with some self-discipline and a focus on big goals. Here are a few ways, big and small, to enjoy the season and position yourself for success at the same time.

Take advantage of summer’s extra daylight. Get going early so you’ll have time later for a drink by the pool.

Read to learn. Put business books and biographies about successful leaders on your summer reading list. Another option: load audio books or podcasts onto your cell phone. Listen to them in your favorite lounge chair during 30-minute breaks.

Visit local businesses in your industry while traveling. If you aren’t in their market, chances are they’ll be open to talking with you about trends as well as what’s worked – and what hasn’t.

Move your office outside. Set up your laptop and phone on your deck or patio to write that marketing proposal.

Help your kids or grandkids start a summer business. A lemonade stand or a dog walking venture can be a bonding experience – plus it might teach you a few things that will help your own entrepreneurial endeavor.

Go to a conference. Choose one that teaches, inspires and provides enough downtime to explore the local city. Bring your family and tack on a couple of days of rest and relaxation.

Volunteer for a summer festival or an outdoor charity event. It’s an ideal way to meet new people and expand your professional network.

Enroll in a summer art class. Learning to draw, paint or take pictures can boost creativity and attention to detail. Artists understand how small design components add to, or detract from, a bigger picture – an important ability in business.

If you’re like most entrepreneurs, one of the reasons you own (or want to own) a business is to have flexibility and control over your schedule. Go ahead and enjoy the summer. Just keep learning and moving forward.

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A Motivational Speaker’s Talk About Roses, Purpose and Self-Fulfillment

After Dana LaMon became blind at age four, he could have wallowed in self-pity and accepted the limitations assumed by others. Instead, he refused to let the loss of sight stand in his way and chose to lead a full, purposeful life.

Dana enrolled at Yale University and earned a Bachelor of Arts degree in math. Then he graduated with a law degree from the University of Southern California, became a member of the California State Bar and had a career as an administrative law judge.

In 1992, he won Toastmasters International’s world championship of public speaking. He’s now the author of four books and a sought-after motivational speaker who travels all over the world.

During a recent district Toastmasters conference held near Washington, D.C., Dana credited the public speaking organization for presenting opportunities that changed the direction of his life. He also had this message: When life hands you a rose, turn it into a bouquet. In other words, leverage each positive experience so it produces even more business success, personal growth and/or enjoyment in life.

How do you turn a rose into a bouquet? Here’s Dana’s roadmap:

R – Relationships. These are the most important assets you can acquire in life. Take the time to cultivate meaningful, long-lasting relationships.

O – Opportunities. The first can lead to another – then another. You can’t wait for opportunities to knock, however. Go and seek them out.

S – Support. Sometimes networking can be shallow and disappointing. Aim to create a support system of people who believe in you.

E – Enrichment. Strive to lead an enriched life – and to help others do the same.

When you combine this approach with perseverance, small victories can turn into bigger ones.  Strive to maximize the value of each win as you build your business and grow as an entrepreneur.  And don’t forget to stop and smell the roses now and then.

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First They Started Businesses. Now They’re Celebrating Milestones.

With Here’s My Story’s Avery Chenoweth (L) and Dominic Sinibaldi

It’s hard enough to start a business after age 40 – or at any age, for that matter. When you can sustain the drive and determination needed to grow the company, create new products and give back to causes, that’s pretty special.

I sometimes wonder about the many late-blooming entrepreneurs featured on this blog.  Where are they now?  Here’s a look at what some of them are up to:

Here’s My Story expects a May 11th release for Time Trekker, the company’s mobile app that uses augmented reality to teach history.  Avery Chenoweth, 61, is the founder of Here’s My Story, which is based in Charlottesville, Virginia. Per the photo above, I had the pleasure of meeting Avery and CEO Dominic Sinibaldi at the app’s beta version testing held at Harpers Ferry National Historical Park last fall.

This year marks the 15th anniversary of Licorice International, the go-to place for licorice lovers all over the world. Elizabeth Erlandson and Ardith Stuertz  were in their 50s when they bought the business from a New York confectioner and move it to Lincoln, Nebraska (their hometown).

Also celebrating a 15th anniversary this year is Drawing Conclusions, a Pittsburgh graphic design firm founded by Donna Herrle after she was laid off from her job two weeks before her 50th birthday.

Len Forkas, who founded Reston, Virginia-based Milestone Communications at age 40, is about to peddle 3,000 miles in the 2017 Race Across America, a California-to-Maryland bike race that’s one of the world’s toughest sporting events. Now 57, Len is racing to raise $1 million for his charity, Hopecam.

Bill McKechnie, who began several Five Guys franchises in Charlottesville and Nashville while in his 40s, has a new restaurant in the works:  Mechum’s Trestle in Crozet, Virginia.

Barbara Cosgrove Lamps has a new addition to its product line:  reproductions of some original paintings created by Barbara Cosgrove herself.  The artwork is a natural extension of the home accents offered by the Kansas City, Missouri company, given that Barbara was an accomplished artist long before she founded her lamp company at age 47.

CS Lewis once said, “You’re never too old to set another goal, or to dream another dream.” Kudos to the entrepreneurs who keep setting goals – and fulfilling them.

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What Entrepreneurs Can Learn From Ellen DeGeneres

You know Ellen DeGeneres as a comedian, daytime television host and an actor.  But did you know she’s also an entrepreneur who’s into designing furniture and pet products?

Ellen has a business called ED Ellen Degeneres, an American lifestyle brand. She was 56 when ED launched in 2015 as a joint partnership with Christopher Burch, the CEO of Burch Creative Capital.

ED’s products range from women’s clothing to home decor.  Among its latest unveilings: a Spring ’17 collection of furniture in partnership with Thomasville, Loloi Rugs and Royal Doulton.  ED also has a line of toys, carriers and other designs for dogs (Ellen and her spouse, Portia de Rossi, own three).

As one of the entertainment industry’s best-known personalities, Ellen has an enormous social media presence, deep financial resources and other advantages that most entrepreneurs don’t have.  These assets enabled ED to grow quickly right from the start.

“ED is an extension of my lifestyle and is inspired by who I am as a person.” — Ellen DeGeneres

Yet her entrepreneurial experience also offers takeaways for any new business owner. One is to stay true to yourself when it comes to designing products that bear your name. “ED is an extension of my lifestyle and is inspired by who I am as a person,” says Ellen on her company’s website.

Another lesson is to choose a business idea that’s a long-term interest. You’re less likely to lose steam when the startup hits a rough patch (which it will).

“I’ve loved home design for as long as I can remember,” Ellen says in this article.  “I know what I like, so designing it made sense for me.”

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How an E-Bike Ride Inspired a Boomer Couple to Launch a New Business

During a California trip to celebrate their 30th wedding anniversary, Scottsdale residents Kathy and Bill Puryear decided to rent electric bicycles to tour some nearby resort towns.  It was a two-wheel adventure that turned into something much bigger.

“We realized that there was nothing like this in Scottsdale, and it could be a really exciting business to pursue,” explains Bill in this post.  They returned home and, six months later, opened Pedego Scottsdale, their own e-bikes store.

Kathy Puryear was among several late-blooming entrepreneurs profiled in this March 2017 Inc. Magazine article about Pedego Electric Bikes, whose products are in a category of bicycles powered by motor-assisted pedaling.  Among the article’s tidbits:

•  Almost all of Pedego’s dealers are in their 50s or older – a demographic that also comprises Pedego’s primary market.

•  Most of these dealers are like Kathy Puryear – i.e., retired or semiretired people who are first-time business owners.  Pedego’s store owners include several former teachers, military personnel and government workers.

•  Pedego has a business model that supports older entrepreneurs and mitigates common skill deficiencies. For example, the company sets up individual stores’ websites and provides social media help since technology has been a challenge for some dealers.

•  Pedego’s co-founders, Don DiCostanzo and Terry Sherry, are serial entrepreneurs who were in their 50s when they started the business in 2008.  Their age helped them design a product that appealed to people like themselves.

DiCostanzo, the company’s CEO, says he and Sherry welcome their latest business challenge.

“I have more energy now than 20 years ago,” he tells Inc. Magazine. “We don’t think of the dealers as old because we don’t think of ourselves as old.”

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Social Entrepreneur Helps Fathers Become Great Dads

By Lynne Strang, Late Blooming Entrepreneurs

Bob Hamrin

Bob Hamrin

As an economist, Bob Hamrin used to spend his days developing policies and analyzing data. One day, he came across a number that knocked his socks off.

“Thirty-six million American children under the age of 18 suffer from father absenteeism that’s physical, emotional or spiritual,” says Hamrin. “It’s a huge problem.”

That disturbing revelation played a big part in the father-of-three’s decision to change course at age 50 and found Great Dads, a Clifton, Virginia-based nonprofit that provides fatherhood training worldwide. The organization’s mission is “to encourage fathers to turn their hearts to their children.”

Over 53,000 men in 45 states and ten countries have taken Great Dads’ training seminar — “The 6 Basics of Being a Great Dad” — which is often held at churches, military bases and prisons. The four-hour training session attracts fathers of all stripes, from 16-year-olds who have yet to finish high school to 66-year-olds who hold executive positions.

Hamrin’s second act as a social entrepreneur is a big change from where he used to be. After earning a Ph.D. in economics from the University of Wisconsin-Madison, he served as an advisor to the Joint Economic Committee of Congress and the Environmental Protection Agency, among other places. Later, he consulted for such organizations as the World Bank and the National Association of Manufacturers and wrote several books.


“Go after what you feel deeply about.  And be willing to take a risk.  If you feel strongly about something, just follow your heart and do it.” — Bob Hamrin, Great Dads


He encountered the startling statistic about absentee fathers while researching a book on fatherhood. Around that time, he and his wife, Carol, heard about several friends experiencing personal difficulties, prompting the couple to become involved with family counseling through their church.

In addition, he had grown weary of working on economic policies that had little effect on people’s everyday lives. It was a perfect storm that compelled him to act.

“I had had a number of entrepreneurial ideas that were intriguing but didn’t tug at my heart,” said Hamrin. “I thought, ‘Either I do this now or I’ll regret it for the rest of my life.”

In December 1996, Hamrin shuttered his consulting practice on a Friday and started Great Dads the following Monday. “I went cold turkey and never looked back,” he laughs.

The nascent group had challenges at the beginning. Bob’s salary was just $6,000 the first year – an especially stressful situation since he and Carol had one child in college and twins who were about to start.

Undaunted, Bob Hamrin pushed forward, making the rounds among churches and submitting applications for financial support. It wasn’t long before he received buy-in from several pastors and won a few small grants. Over time, Great Dads picked up steam, forming partnerships with such groups as Prison Fellowship and Forgiven Ministry.

Great Dads, which just celebrated its 20th anniversary, now gets its funding primarily from individual and church donations as well as training fees (proceeds go back into the organization).  Hamrin has a team of seminar instructors who have been fathers for a while (associates must have at least one child who is age 16 or older).

Hamrin attributes his success to his faith, optimism and entrepreneurial mindset. His future goals include a stronger social media presence for Great Dads and new, creative ways to communicate its message. At age 70, he’d also like to find a successor to take over for him one day.

Meanwhile, he still gets gratification from working on a cause that truly matters. For those considering a life change, he offers this advice:

“Go after what you feel deeply about. And be willing to take a risk. If you feel strongly about something, just follow your heart and do it.”

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