Learning from Entrepreneurs Who Have “Been There”

One way to test the waters of entrepreneurship is to talk with people who have started a business. Where better to get advice, technical help or a real-life perspective than from entrepreneurs who have lived through the startup process?

Social media provides plenty of opportunities to find entrepreneurial types who enjoy helping others. This week, I hosted an online interview about my book, Late-Blooming Entrepreneurs: Eight Principles for Starting a Business After Age 40. The interview was for Yabbly, an “Ask Me Anything” site where readers can find interviewees of interest and ask them questions about, well, anything.

While interview hosts come from all walks of life, a large percentage of them are entrepreneurs, career changers or others connected to business. The interviews aren’t in real time but readers who ask questions usually get answers from the hosts within a few hours.

Here are five Yabbly interviews that readers of this blog might find especially interesting:

I started my nursing career at age 46

I had my startup exit & was never more scared for my life

I help people land their dream jobs

From entrepreneurship professor to inventor of consumer product now on Kickstarter

I’ve helped 10 bootstrapped technology businesses sell or raise capital

Other “Yabblers” include the cofounder of the Xbox and a top executive with Bing. They’re are on the site because they’re willing to share what they know. Why not ask them a few questions?

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Why Leaders Get Better With Age

Companies prize young talent. And rightly so. In an era of instant communication, they need young, tech-savvy leaders who can help them to get things done faster.

Still, speed by itself doesn’t equate to business success. Sydney Finkelstein wrote about this in a recent BBC article. In it, he recalls the classic Aesop’s fable about the tortoise and the hare. It’s the plodding tortoise, and not the speedy hare, that crossed the finish line first.

Experience may not bring speed – but it does bring wisdom and other traits/abilities. Among them:

Perspective – Age brings a greater ability to reflect and put into context what is happening around you.

Deeper compassion – This extends to the people in your life, both at work and at home.

A dose of reality – The illusion of perfection has long gone.

Empathy – “Once you’ve live a little, it becomes harder to go about your work without paying closer attention to colleagues and empathizing with those around you,” writes Finkelstein.

An ability to motivate others – That’s because you better understand what makes them tick.

An appreciation for details – Leaders who have been around the block a few times can’t help but see the nuances and subtleties of work that less-experienced managers do not see.

Acceptance of life’s ups and downs – As Finkelstein puts it, “You’ve seen bear markets and not just bull markets.”

Experienced leaders don’t always make the right calls, of course. But they have a lot going for them. Remember that as you plan your entrepreneurial endeavor.  A plodding tortoise isn’t a bad thing.


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Opening a Law Practice at Age 72

When Pennsylvania resident Carolyn Newsom decided to go to law school at age 68, she wasn’t the only one there who was making a midlife career change. A half-dozen women with her at the Widener University School of Law were at least 40 years old. They called themselves the Ladies Justice.

“It was great to have a group of women to be supportive of one another,” said Newsom in this article appearing in The Intelligencer. She passed the Pennsylvania and New Jersey bar exams in 2012.

At age 72, she’s started a law practice that focuses on estate planning. It’s her third business venture.  Previously, she had two consulting practices based upon expertise she cultivated during her earlier careers with IBM and an international consulting firm.

“I sort of reinvent myself every seven to ten years,” said Newsom, who also volunteers Wills for Heroes. The nonprofit, born from the September 11th tragedies, caters to first responders. Newsom was on the 44th floor of the North Tower when the first plane hit it.

By all accounts, Newsom has earned some time to relax. But apparently she has no plans to do so.

“My goal is to never retire,” she said. “I can’t imagine what retirement would be like.”

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Centenarian Cyclist Breaks World Record

Late bloomers of all types often can find inspiration from the world of sports. For living proof that age is just a number, look no further than 102-year-old Robert Marchand. This guy is amazing.

Marchand, who’s from France, broke his own world record in speed cycling a few weeks ago when he rode 26.927 kilometers (16.7 miles) in one hour. That time beats his previous record by more than 2.5 kilometers and keeps him at the top the 100-plus age group.

Marchand set his new record in France’s new national velodrome, whose official inauguration was one day earlier. Spectators gave the cyclist a well-deserved standing ovation when he reached the finish line.

As reported in this New York Daily News article, Marchand — a retired firefighter and logger — also holds the record in the age 100+ category for riding 100 kilometers (62 miles). He did it in four hours, 17 minutes and 27 seconds in 2012.

For a glimpse of Marchand’s latest accomplishment, check out this video.

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Help is Out There for 40-and-Older Entrepreneurs

Looking for third-party support or guidance to launch your startup – but aren’t sure where to turn? Here’s a list of organization, programs and publications that may be useful for aspiring or new business owners. Many of these resources are from Late-Blooming Entrepreneurs: Eight Principles for Starting a Business After Age 40.


AARP – Has an entrepreneurship resource center on its website. www.aarp.org

Center for Productive Longevity – Serves as a bridge between employers seeking needed talent and people age 55 and older who have the capabilities and desire to continue working with employers as well as in entrepreneurial or other activities. www.ctrpl.org

Cycle of Success Institute (COSi) – Educates, coaches and transforms small to mid-sized companies into profitable, innovative, high-growth businesses that fuel job creation and wealth. www.cycleofsuccess.net

Encore.org –This group “is building a movement to make it easier for millions of people to pursue encore careers – second acts for the greater good.” www.encore.org

Ewing Marion Kauffman Foundation – The world’s largest foundation dedicated to entrepreneurship. www.kauffman.org

Franchise Direct – An online portal of franchise opportunities and information. www.franchisedirect.com

National Federation of Independent Business – Includes resources on starting a business, financing and accounting, etc. www.nfib.com

RetiredBrains.com – An independent job and information resource for boomers, retirees and people planning their retirement. www.retiredbrains.com

Senior Entrepreneurship Works – Helps those age 50 and older build sustainable businesses, create jobs and stimulate economic self-reliance. www.seniorentrepreneurshipworks.org

SCORE – Provides free counseling, resources and advice to people who are in business or want to start a business. Website materials include templates for business plans and financial statements. www.score.org

U.S. Chamber of Commerce Small Business Nation – A community that “was founded on the open exchange of information and ideas, while creating the opportunity for small businesses to speak with a unified voice.”  www.uschambersmallbusinessnation.com

U.S. Small Business Administration – Provides loans, loan guarantees, contracts, counseling sessions and other forms of assistance to small businesses. Website materials include templates and step-by-step guides for writing a business plan. www.sba.gov


eProv Studio – A training workshop that combines the methodology of entrepreneurial thought and action and the art of improvisation. http://www.eprovstudio.com/

Kauffman’s FastTrac for the Boomer Entrepreneur – An entrepreneurial course for those age 50 and older.http://fasttrac.org/en/Entrepreneurs/FastTrac-Courses-for-Boomers.aspx


Mature Entrepreneur Planning Guide, NYS Small Business Development Center, The State University of New York.  www.nyssbdc.org/resources/Publications/09_mature_entrepreneur_planning_guide.pdf

BoomerPreneurs – How Baby Boomers Can Start Their Own Business, Make Money and Enjoy Life, M.B. Izard. www.consultach.com/boomerpreneurs

Second Acts – Creating the Life You Really Want, Building the Career You Truly Desire, Stephen M. Pollan and Mark Levine. http://www.amazon.com/Second-Acts-Creating-Really-Building/dp/0060514884


Know about other resources that could be added to this list?  Please leave a comment below.

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Grocery Entrepreneur Seeks to Help Working Families

For 31 years, Doug Rauch helped Trader Joe’s Company grow from a small operation in Southern California to a national chain that has more than 400 stores these days. Now Rauch — who served as Trader Joe’s president for 14 years before retiring in 2008 – has a new grocery store in the works that’s rather unconventional.

The Daily Table, Rauch’s Dorchester, Massachusetts-based store and restaurant, will open its doors in May. When it does, the nonprofit will sell surplus food from supermarkets and growers, including some that is past its “sell by” or “best used by” date.

As Rauch explained in this ajc.com article, he hopes to make food more affordable for poor households in the Dorchester area. “Most families know that they’re not giving their kids the nutrition they need, but they just can’t afford it, they don’t have an option,” Rauch said.

“A lot of food is wasted (because) consumers do not know what all the dates mean,” said The Daily Table’s Fredi Shonkoff in this article. “They’re not standardized or regulated. We need to do a lot of education so that people aren’t tossing perfectly healthy, nutritious food.”

Like other grocery stores, the Daily Table will inspect deliveries and sort out bad product before placing it on the floor. It will also offer prepackaged items that can be turned into a healthy dinner (for example, chopped vegetables with a recipe for stir fry) and prepared meals that can be chilled or frozen for later.

If the Dorchester store does well, the Daily Table will expand to other areas within Massachusetts. Food industry executives in other cities, such as Los Angeles, Chicago and Philadelphia, have expressed interest in having a store in their area.

That reaction seems consistent with Rauch’s long-term vision. “This was always intended to be a large-scale project, if the concept is proven to be effective and sustainable,” he said. “These are large ‘ifs,’ but I believe within the range of being achievable.”

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Ten Steps for Starting a Software Business

Jim Kelly

Jim Kelly

Jim Kelly is a Bethesda, Maryland-based serial entrepreneur whose expertise includes software technology solutions and venture capital. In 1996 — at age 55 — he left his position with BDM to start his first company: SynXis, a hotel reservation management software provider sold to Sabre in 2005. Later that year, Kelly (a former pilot) and his business partner, Bob Wright, launched Flight Explorer, a software and IT solutions provider to the global aviation community that was created from a division within Wright’s company, Dimensions International. Over the next three years, Kelly and Wright used a software product that tracks planes in flight to build Flight Explorer before selling the company to Sabre in 2008.

Kelly also is the founder of Innovectra, a telecommunications software provider acquired by Edison Venture Fund in 2003. His current businesses include a medical startup and a publishing company. He draws upon his own experience to offer the following ten-point plan for aspiring software entrepreneurs.

1. Define your mission. Document it in a written business plan that also spells out your products, services and markets. Make sure everyone in your organization is in full alignment. There should be no “If we build it, they’ll buy it!”

2. Implement a structure. This will require action on several housekeeping items. Are financial records established and up to date?  Do you have an attorney who understands your company and will give knowledgeable advice when you need it?  Are employee contracts fully documented with non-compete clauses and ownership plan references?  Have you reviewed employee backgrounds for any surprises? Is your business insured?

3. Choose your management team. Are the right people in the right seats on the right bus going in the right direction?  If not, make changes quickly. Personnel issues are – by far — the hardest part of management. Few people handle them effectively. 

4. Cultivate your funding sources. Establish banking and shareholder relationships to ensure access to sufficient capital when and where you need it (for example, acquisitions). If you or other owners are not up to contributing additional capital, develop relationships with outside sources of debt and equity. Consider a line of credit as a way to build a credit history and banking relationship. Banks offer $50,000 Small Business Administration (SBA) loans to startups that have been in business for at least two years.

5. Don’t shortchange software development. This is the lifeblood of your company. Is the intellectual property fully in your hands? Is the development process documented?  Even though outside contractors may assist, self-reliant enterprises will carry more weight. Make sure you have a serious process, such as a Product Review Board, in place to match development priorities with market requirements effectively.

6. Invest in a marketing and sales operation. As the marketing and sales team seeks new customers, it needs to stay engaged with existing ones at all times. Be aware that sales personnel compensation plans tend to be more complex in the software world. Management must make a special effort to adjust and readjust the plan to maximize sales productivity. Finally, remember that the enemy has a vote; the sales team always needs to be mindful of real and imagined competition. Many times, a supposedly minor player becomes an industry leader because the competition wasn’t paying attention!

7. Price your products and services carefully. Prices that are too low or too high will result in an early death of the organization. Failure to conduct frequent price reviews will only enable competitors.

8. Build relationships with partners. They can be helpful in verifying need, defining requirements, supporting concept tests, determining the pricing and spreading the good word within their respective communities. They can also be important sources of information about the competition. Product development with partners should be an enterprise rule.

9. Test the delivery. Has someone other than the developers vetted the software? Is the delivered product within the expectations of the customer? Usually, sales or support undertake this function in the initial phase — but as the organization grows, you’ll need to invest in Quality Assurance personnel.

10. Provide complete customer support. If a customer has an issue, are his or her options clear? Does your company have a disaster recovery plan in the event of a catastrophe (software fault or major delivery error)? Everyone in the organization should know his or her battle station when things go really bad, as they are bound to do once in a while. Be ready!


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