5 Podcasts for 40-and-Older Entrepreneurs

Photo by Matt Botsford on Unsplash

Looking for a different perspective, a dose of inspiration or new ideas you can apply to your business?  Give a listen to one or all of these five podcasts:

Business Schooled — Alexis Ohanian, co-founder of Initialized Capital and Reddit, travels to eight U.S. cities to interview boomer and Gen-X entrepreneurs and learn how they got their businesses off the ground.

How I Built This – Hosted NPR’s Guy Raz, How I Built This weaves a narrative journey about innovators, entrepreneurs and idealists – and the movements they built.  Some of the episodes feature late bloomers like John Foley, who founded the fitness company Peloton in his 40s.

Your Next AvenueA podcast about working after 50.  Host Richard Eisenberg, the managing editor of nextavenue.org, explores topics that range from “how entrepreneurs can find their target audience” to “making a career pivot after 50.”

Not Impossible – This podcast asks the question, “What if nothing in life is impossible?” Host Mick Ebeling, the founder of Not Impossible Labs, presents uplifting stories about people who have created technology for the sake of humanity.

Your Next Chapter Podcast – Angela Raspass is the host of this podcast especially for 40-and-older women who are current or aspiring business owners. The episodes feature interviews with women from around the world who are creating Next Chapter businesses and lives that are both personally and professionally fulfilling.

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How a 60-Year-Old Entrepreneur Crushed His First Gravel Bike Race

By Lynne Beverly Strang

A bit of weirdness during the DK 200. Jim posed for this pic around the 170-mile mark. Chaise and photo courtesy of Salsa Cycles.

Since this blog began in 2010, I have profiled all kinds of entrepreneurs — but I’ve seldom featured a family member. Happily, I get to write about one for this post.

Earlier this month, I traveled to Emporia, Kansas to watch the Dirty Kanza, an annual gravel road cycling event with several distance options. Among this year’s 2,700 registrants was my husband, Jim, who owns six bicycle stores throughout Northern Virginia. At age 60, Jim was a first-time rider in the DK200, a self-supported, 200-mile endurance challenge.

With gravel grinding, cyclists usually ride on gravel, rocks and/or packed dirt. Typical routes are trails and backroads with little or no traffic – one of the reasons this type of cycling is becoming more popular.

Although I’m a long-distance cyclist myself, I couldn’t helping wondering what my spouse had gotten himself into when he set out to race 200 miles in one day. The dusty, hilly DK200 has just two checkpoints and goes through Kansas’ remote, rugged Flint Hills, described here as “the largest expanse of tall grass prairie existing anywhere in the world.”

A glimpse of the Flint Hills in Kansas.

Thanks to meticulous preparation and a disciplined training regime, Jim did great. He finished in under 16 hours and placed ninth in his age category. Not bad for a sexagenarian rookie.

While gravel riding and entrepreneurship may seem unrelated, they have much in common. For one thing, the sport tends to appeal to hard-working businesses people like Jim, who relish the opportunity to escape for a few hours of outdoor exercise in a quiet, peaceful setting.

In addition, endurance athletes and entrepreneurs share certain characteristics, including a desire to push themselves. As a spectator of the Dirty Kanza, I came away with these reminders about success:

Preparation is key. Fulfillment of a goal requires research, careful planning and a timetable. You usually don’t get the outcome you want if you wing it

Perseverance is critical. Some want to traverse 200 miles of gnarly gravel roads on a bike. And some aspire to navigate the pitfalls, setbacks and tough times that come with starting and operating a business. In both cases, you need a will to succeed.

You can’t do it alone. Your odds for success improve greatly when you join a supportive group of fellow athletes or business owners who share tips and ideas. You also need family members who encourage you to pursue your dream.

Age changes your perspective. As you get older, success becomes more about the journey than the destination. It may take longer than it did 10 or 15 years ago to crest a hill or cross the finish line. But each scenic view, each high five, is sweeter.

Congratulations, Jim. And congratulations to all of this year’s Dirty Kanza riders who took on a challenge bigger than themselves. You rock, literally and physically.

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A Second Act That’s a Real Hoot

By Lynne Beverly Strang

“Humor is so important,” says Donna Cavanagh of HumorOutcasts.com. “If we don’t have humor, we don’t have a life.”

What if you could create an online community that brings together some of the funniest people on the planet?  That lets writers, stand-up comics, cartoonists and other humorists publish their work, push the envelope and spread their creative wings?

For Donna Cavanagh, that “what if” became a reality eight years ago, when she started HumorOutcasts.com in her late 40s. In its “About” section, HumorOutcasts.com describes itself as “THE place to take a humor break.” Visit this site and you’ll find funny stories, drawings and musings about everything under the sun, from pancake house waitresses to Kim Kardashian’s new baby nursery.

At an earlier age, the Philadelphia, PA-based writer never envisioned founding a website for people who needed a chuckle.  Her entry into humor was “sort of accidental,” says Cavanagh in a podcast interview with BizStarters’ Jeff Williams.

An Unexpected Career Pivot

She started out as a night-shift newspaper reporter covering Montgomery County, PA. As explained in this article for Chestnut Hill Local, her career took an unexpected turn when she “lightly skewered her boss in a piece circulated at an office party.”

Cavanagh was understandably nervous when the boss called her into his office the next morning. But instead of handing her a pink slip, he complimented the holiday piece and asked her to start writing humor. And so a humorist was born.

Eventually, Cavanagh left the paper and spent several years writing syndicated humor columns for Pennsylvania and national publications. Then the big online sites began slashing humor, leaving few opportunities for her content. Rather than lamenting about the situation, Cavanagh decided to do something about it.

A Hobby Turns Into Something Bigger

With technical help from her computer engineer husband, she set up a website in 2011 as “a hobby sort of thing.” She chose the name HumorOutcasts.com because it described how she and her fellow humorists felt in the Internet writing world.

From there, things “sort of took off,” says Cavanagh. Today, HumorOutcasts.com showcases the talents of more than 100 writers, from newbies to award-winning television writers and producers. The site gets between 2,500 and 20,000 hits per day.

The website’s success has led Cavanagh to form a publishing house that now has more than 60 titles. Her company publishes books under three labels: HumorOutcasts Press for humor; Shorehouse Books for other genres; and Corner Office Books for professional, business and legal books.

Cavanagh herself is the author of several books, including How to Write and Share Humor: Techniques to Tickle Funny Bones and Win Fans. While she enjoys showcasing the work of funny writers, there’s a serious side to what she does.

“Humor is so important,” she says. “If we don’t have humor, we don’t have a life.”

“Nothing Happens Overnight”

Her advice for 40-and-older entrepreneurs? Learn about technology. Take classes, be up to date and have fun with it. If you don’t want to handle social media yourself, hire someone who knows what they’re doing.

“Getting discouraged is part of the game, so don’t let it drag you down and don’t be afraid to learn,” she says.

She also points out the need for patience.

“It’s a wonderful time to do what you want, but nothing happens overnight,” says Cavanagh. “Each day is a challenge but each day is the opportunity to do what you love.”

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How a 45-Year-Old Doll Maker Began Changing Children’s Lives

As a pediatric oncology social worker, Amy Jandrisevits used dolls in play therapy to help children express themselves. Then one day, a revelation struck.

“I realized that the dolls’ thick hair and perfect health were doing the kids I was working with a disservice as they were often faced with a wide variety of physical challenges,” she explains here.

Her research found no places that produced dolls with prostheses or missing limbs. So Jandrisevits, a mother of three who lives in New Berlin, Wisconsin, decided to take action.

In 2014, she started A Doll Like Me, which provides custom-made dolls for children with physical disabilities. Along the way, the 45-year-old has found a way to combine her long-time hobby of doll making with her passion for social work.

One of her first dolls was for a little girl who just had a leg amputated. Since then, Jandrisevits has made dolls for children with a wide range of medical circumstances. Each doll mirrors the owner’s gender, ethnicity, interests and body type – so the child can look into the doll’s face and see his or her own.

“Whatever it costs, whatever I have to do, I’m going to get a doll in the hands of these children. This isn’t just a business. It’s the right thing to do.” — Amy Jandrisevits, A Doll Like Me

“In an ideal world, limb difference, body type, medical condition, birthmarks and hand differences would be as accepted as all of the other things that make us unique,” says Jandrisevits on A Doll Like Me’s Facebook page. “Until then, kids might need a little extra coaching…and something that will help them feel proud of who they are.”

Jandrisevits, who has made over 300 dolls in the past four years, has many names on her waiting list. She started a GoFundMe campaign to raise funds to pay for the dolls when parents or caregivers can’t afford them (each handmade doll costs around $100 with shipping).

“Whatever it costs, whatever I have to do, I’m going to get a doll in the hands of these children,” says Jandrisevits. “This isn’t just a business. It’s the right thing to do.”

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Finding Your Business Idea

For 40-and-older entrepreneurs, the number one reason for starting a business isn’t necessarily to make big bucks.  It’s more about doing something that’s enjoyable and gives you a sense of fulfillment.

In this video post, I describe a very simple method I used a few years ago to assess what I wanted — and didn’t want — in my next business opportunity.  Maybe this technique can help you as well if you’re an aspiring entrepreneur who’s evaluating what product or service to offer.

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A Retired Admiral Becomes an Entrepreneur – And Finds a New Way to Serve Others

Robert O. Wray, Jr.

As a two-star nuclear-trained admiral in the U.S. Navy, Robert O. Wray, Jr. inspected ships, submarines and carriers while reporting to Congress on their status. Now he’s found a new calling: creating technology to help seniors.

What led him to this business idea?  Two things.

One, he wanted to do something to help his aging parents and in-laws.

And two, he saw a void in the marketplace for technology that assists seniors, the fastest growing segment of the American population

In 2013, Wray founded BlueStar SeniorTech when he was in his mid-50s. The Rockville, Maryland-based business offers technology-based products and services to help seniors, veterans and their family members age safely within the comfort of their homes.

“As a proud member of the Naval Academy and product of a family who has multiple generations of veterans who have served our country including my own dad and father-in-law, I feel it is our duty to provide this service,” said Wray in this announcement.

Among BlueStar’s suite of products are wearable medical alerts and health monitoring devices. There’s also a controller that turns off the heat of a stove when left unattended, and a smart pillbox that helps people remember to take their medications at the right times.

BlueStar serves all seniors but hires vets, donates to veterans causes and offers special pricing to vets and their families. Not surprisingly, the company gets its name from the military (a Blue Star family consists of the immediate family members of someone who currently serves in the Armed Forces).

Wray’s former life as a Navy officer is very different than his current one as a business owner.  But these two occupations have at least one thing in common.

As a recent story on local television station put it, “In uniform, he served to protect.  As a civilian, his mission remains the same.”

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A Late Bloomer Tries Her Hand at Video Blogging

After eight years of written posts, it’s time to change things up.  So here’s my first video post for Late-Blooming Entrepreneurs.

The topic is – what else? – video blogging for entrepreneurs.  If you’re thinking about video blogging (or vlogging), I encourage you to give it a try.  Sometimes the hardest part is getting started — especially if you aren’t used to seeing yourself on camera.

At the end, I offer my thoughts on the biggest marketing advantage that video blogging provides for business owners.

I hope you enjoy the post.  As always, thanks for stopping by.


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