Experts Weigh In: I’m an Entrepreneur in My 50s

Experts Weigh In: I'm an Entrepreneur in My 50sAfter spending three weeks with teen entrepreneurs, twentysomething ‘treps, and entrepreneurs in their 30s and 40s, we’re taking a look at savvy entrepreneurs in their 50s! Our 30 professionals profiled today have plenty of pearls of wisdom that come with being in business including opting for triads over partnerships and that there is no glass ceiling when you work for yourself.

1) “So I’ve done a LOT! I’ve worked for companies, I’ve owned companies. The best part about being an entrepreneur at age 53 is that I’m in control of my destiny. Many of my friends are worried about their retirement accounts, for me, being an entrepreneur is like early retirement with a cash faucet! I can work as much or as little as I want or need. I don’t plan to retire, I do what I love and plan to keep on doing it.”

Karen Yankovch, 53, Owner, Social Media Brand Strategist

2) “The best part of being an entrepreneur in my 50s is that I’ve already made a WHOLE LOT OF mistakes. I also have learned that nothing is quite as good or quite as bad as it seems, so I’m less panicked and more stable in my thinking. I’m also much more focused on working smart not hard, but often still do some of both!

Many people require structure and need to be told what to do and have goals set for them. The biggest challenge with being an entrepreneur is time management and making sure I get the stuff done that I don’t like doing, before I get into the fun stuff. It’s a scheduling thing, but here again, I’ve been doing it for quite a while, so I know when I need to just hunker down and clear off the desk.

One last word of advice for entrepreneurs – think triads, not just partnerships. While partnering with like minded and complementary businesses is great, developing triads is even better. If I can get two people together that can help each other, it’s easy for me to tag along, because if it’s helpful, they both have a reason to include me where appropriate. Win-Win-Win is better than Win-Win.”

John Schaefer, 59, Founder and President, Schaefer Recognition Group

3) “After receiving my MBA in Finance I worked on Wall Street for about 20 years as a fixed income trader and proprietary equity trader before leaving to open up a company that originated commercial mortgage loans and then sold them to banks who turned them into bonds. When Lehman Brothers failed and the market seized I had the opportunity to open a title insurance firm which I jumped on. Six years later and we are doing great.

The best thing about being an entrepreneur at 50+ is the autonomy it provides to do and run things the way that you think best. The issue with being an entrepreneur at 50+ is the fact that if for some unforeseen reason the business does not work out, prospects for getting hired in the conventional job market are dicey. For that reason I just have to make sure that we succeed!”

Mike Haltman, 54, Owner, Hallmark Abstract Service

4) “I started a You Tube channel (kenboydstl) years ago to improve accounting education. That has lead to 3 (soon to be 4) Dummies books on accounting and finance, and a growing business tutoring online and speaking in person. The best part: There’s customer demand for a service I really enjoy providing. I’m passionate about what I do, so each day has real satisfaction.”

Ken Boyd, 51, Owner and Founder, St Louis Test Prep

5) “After reading the 4-Hour Work Week by Tim Ferriss I started looking for a business to start. I discovered that there was a gap in the market. There was no way to compare adventure travel like you might compare flights or hotels. So I created the TripTrist Adventure Travel Search Engine. You can search through 100’s of tour companies and 1000’s of tours all in one place. (And growing!) There are two kinds of experience I brought with me: 1) A calm, control what you can and don’t worry about what you can’t, attitude I learned from 30 years of working. 2) Knowledge and skills in working with people, marketing, sales, and business principles. The best thing about being in my 50s is I have the time, money, experience and most importantly – there is no pressure to do what is expected.

Doreen O’Donovan, 54, Owner, TripTrist Travel Planner

6) “I am a serial entrepreneur/optimist/lawyer. Left the legal profession after three years and started a company with my wife when we moved to Los Angeles in 1990. We now own/operate four companies based in Dallas Texas under the Whitson Wells PMG, LLC banner named after our children (Whitson 19, Wells 14). The best part is the freedom to go to my kid’s events, take vacations or trips on our own time, and  opportunity to pursue other ideas.”

– Robbie Weinberg, 51, Owner, JustFrocket

7) “I launched my business about 5 years ago after spending 30+ years in the corporate world. I call myself a reluctant entrepreneur as owning my own business was not something to which I had previously aspired. I decided to pursue this very different path after the musical chairs of yet another reorganization (8th in about 8 years) left me without a seat. I decided I could either wallow in self-pity of being un-hirable or forge my own destiny, so I chose the latter. My business is a franchise which  provides business support services to individuals, businesses and organizations who want the flexibility of professional support without the hassle of hiring and managing full or part time staff. The best part of being a 50 something entrepreneur is I can take the skills, talents and experiences of working for large corporations and apply them to my company as well as help my clients with real world advice. Another is the freedom. And a third is I am no longer afraid to make mistakes – making mistakes helps us grow and become better for having made them. That is a lesson that comes with being ‘vintage.’”

– Joyce Kane, 58, Owner/President, JPK Virtual Assistant, INC

8) “I stared my business Cooperative Kids back in 1995, helping parents and teachers rebuild their discipline toolboxes. My full time position was an IT Director at a large insurance firm. In 2009, I got laid off with about 1000 other mid and low level managers and I launched my parenting business full time. It grew to become very successful and from that, I wrote several books and launched a television show and radio show on the Clear Channel network.

After speaking at conferences around the country on behavior, small business owners would ask me how I developed such a unique marketing plan around parenting.  So I wrote the book The 2.0 Entrepreneur: 20+ Marketing Strategies for Growing Your Business Off and Online. Now I find myself doing more marketing consulting than parent education counseling.”

Bill Corbett, 55, Cooperative Kids

9) “I am 53 and CEO of Patrol Services International. My firm specializes in integrating former police officers into the private sector. We also provide franchise opportunities which are almost entirely made up of people over 50. The best part of what I do is helping clients find solutions in dealing with the unfortunate side of our society, and thus preventing them from being victims.”

Nick Thompson, 53, CEO, Patrol Services International

10) “I started my career in academia, but two years after getting tenure I gave in to my passion for entrepreneurship. Since then I have been involved with two startups and a consulting/R&D organization. A year ago I became CEO of Infomous, a visual exploration company that helps publishers engage readers and make their content easier to discover. While I admire the drive and energy of entrepreneurs half my age (or younger!), I enjoy being a 50-something entrepreneur. I see patterns that I have built up over decades of work. Also, the grey hair can add credibility in some client and investor meetings. But the best part for me is that over time I have figured out how to work smarter rather than harder, maintaining a better work-life balance.”

Paolo Gaudiano, 51, Founder and CEO, Infomous

11) “I believe being an entrepreneur in your 50s has advantages. Using all the information and experience I have gained through the years has increased my confidence and helped me handle stressful situations. I have also honed my communication, negotiation and presentation skills. I started my career as a Wildlife Artist, part-time, when I was 19. Four years later, I resigned from my conservation law enforcement position and committed myself to my business full time, and have been successful for over 30 years. I create original art, limited edition prints, greeting cards, ornaments, and jewelry. I have an online gallery and work with many collectors, wildlife organizations, corporations and small businesses. At 51, I enjoy the freedom of setting my own hours, choosing my charity work, homeschooling my daughters and training my horses and dogs.”

Nancy Quinn, 51, Owner, Nancy Z. Quinn Wildlife Art

12) “I started my own business two years ago when I realized that after interviewing for 6 months I wasn’t going to be offered a full time position in my field. I now work with a number of small businesses that need public relations but can’t afford to retain a full time agency with the large fees. I provide them individual service at a fraction of the cost. I am not making what I was as a full time in-house publicist but have much more flexibility, can work from home and am nowhere near as stressed out as I once was.”

Lisa Wells, 50s, Owner, Lisa Wells PR

13) “I am 52 years old and running a custom cabinet manufacturing shop that I began 12 years ago. The best thing about doing this and running this business to me is that is showing my three (now adult) children that you can accomplish anything you wish in life.”

– Linda Bishop, 52, LWi Custom Cabinets

14) “I’ve been an entrepreneur for more than 20 years and I’m currently on my 3rd business. Why? Because that’s what being an entrepreneur is all about! Being your own boss gives you permission to follow your hunches, go where you feel motivated to, and open any kind of business you desire. No asking permission, no bending the rules. Your success or failure is completely up to you – and while that can be scary at times – it’s also completely liberating – there is no glass ceiling when you work for yourself.”

Evelyn Cucchiara, 52, Owner, Art Adventures Inc. and Evelyn C. – The Sanity Saver

15) “I am a 53 year old single mother of two and formed my PR agency 12 years ago on a $50 investment. As a woman entrepreneur in a highly male dominated tech industry, I have established a credible business, launched dozens of companies in the consumer and tech sector, and mentored among the way.

I am most inspired by the entrepreneurs I work with daily and launching their dreams from zero to 60 often. My clients are as young as 19 and into their 50s. Having at least 3 decades of business, tech communications gives me a competitive edge and the name ‘The PR She Devil of the Silicon Valley and Beyond.’”

Donna Michaels, 53, Owner, LMGPR

16) “I’m an entrepreneur who started a beauty business after inventing and taking a product to market. I developed a lip enhancing beauty tool and jumped feet first into the beauty industry!  I love being an entrepreneur in my 50s as I have the confidence, experience, and well-developed ideas that I would not have had venturing down this path in my younger years. I additionally have had the pleasure of meeting other baby boomer entrepreneurs, who I have found to be an exceptionally hard working, respectful, and creative group of people!”

Linda Gomez, 58, CEO, Fullips

17) “I left the security of being a partner at a law large firm in Chicago and started my own law firm. I traded security for the excitement and freedom of doing my own thing my own way. A few years later, I then decided to start my own publishing company, Coconut Avenue, Inc.

I used all of my education and experience in technology, have a Ph.D in computer science and was a professional software engineer, and I practice intellectual property law (patents, trademarks, copyrights) to create a new publishing business model and grow my start-up into a successful publishing company. I am 55 years old and really enjoying the ride. I depend on myself for a paycheck and control when and how I work and also control my own view of retirement.”

Stephen Lesavich, PhD, JD, 55, Founder, Attorney, Lesavich High-Tech Law Group, S.C., Coconut Avenue, Inc.

18) “I have a somewhat interesting story of leaving corporate America to be an entrepreneur. Made it big, lost everything, but survived for the last 8 years and I’m rebuilding my professional and personal life. I am currently 51 and starting from ground 0. I reinvented myself as a consultant/mentor/coach to individual real estate owners and companies. The best part of being an entrepreneur in my 50s is that, even though I lost what I had made, there is always the chance to do it again – at any age.”

Gary Klein, 51, Founder, Cornerstone Real Estate Organization

19) “After a 27 year career in Federal law enforcement I decided to retire and start this company. I could have kicked back, collected my government pension and not get too worked up about anything. But there was no challenge in that and I knew I still had a lot of energy and a passion to see if I could make this company work. I see a tremendous potential with small healthcare providers who are unclear about the government requirements. As a former Assistant Inspector General for Investigations at the U.S. Department of Health and Human Services, Office of Inspector General, I want to give back and help healthcare providers understand how to make sense of the Code of Federal Regulation (CFR) that govern HIPAA compliance. It’s kind of different having a seat on the other side of the table.

I find a much different set of challenges facing me each day and totally different from government service. As an entrepreneur and owner, one needs to juggle many unfamiliar hats from business networking, marketing and sales to actually providing the services. Unlike my prior job, there is no option to delegate. The best part for me is that my leadership lessons from government service have prepared me well especially being the face of my company and any opportunities for public speaking. I enjoy writing my blog pieces and providing opinions and interpretations of the CFR as a way to give back. To me, this is a value proposition. A term that was not in my government vocabulary.”

Jay Hodes, 54, President and Founder, Colington Security Consulting

20) “I am an entrepreneur who’s 50 and I love working for myself for several reasons. I have freedom, flexibility, and drive that will be applied to my bottom line. I’m a single mom with three teens at home and I love helping my clients and coaching clients. I also sub-contract to other companies as well!”

Nancy Michaels, 50, Entrepreneur

21) “I started a coaching business to empower women, especially women in transition from being Mommy or Corporate Career Woman into Empty Nester or Passionate Purpose-Driven Entrepreneur. I teach the power of your words, thoughts and actions and how you can create a life you love using the Universal Laws such as Law of Attraction. The most amazing part of this journey is helping other women connect the dots so they can actually see how their thoughts and beliefs affect their lives. When they recognize the power of stepping into their true Goddess energy, they see how they can be a co-creator of their life experiences. Then it’s bye-bye to being a victim of circumstances and hell, yeah! to living a life they love.

I love having the freedom to set my own hours. I prefer to work in the evenings, so it makes it easy to care for my family during the day. I also love that if my grandchildren have dance or school events going on, I can be there to share it with them. I get to have the best of both worlds – working and making a difference in the world with something I’m passionate about, and having the freedom to decide when, where and with whom I want to work.”

Jacquelyn Gioertz, 57, Goddess Guide, Empowered Consciousness LLC

22) “I am a 57-year-old self-taught programmer. My current company is one of the leading property management software products on the market (Tenant File) which I authored by myself. I am constantly seeking other opportunities to develop new business ideas. Creativity is what motivates me, and I am developing other businesses in such diverse fields as real estate home sales, musical instrument sales, children’s videos, and more. In my free time I record and perform rock and country music. I love being an entrepreneur because of the thrill of seeing new ideas get off the ground. Just managing a business is not enough, I need to be a part of the creative process, which is what keeps me excited about the next new adventure.”

Wayne Gathright, 57, President, W G Software, Inc.

23) “I own and operate a small business for children and special events called Reptile Adventure. It is a local business providing fun and educational shows and exhibits with all types of reptiles. I began this business five years ago when I returned to college after my last food service business of 15 years failed due to the economy. Business has more than tripled since its inception, so I now work it full time.”

Donna Turner, 55, Owner, Reptile Adventure

24) “My husband and I are both over 50 and entrepreneurs. Our current business is PickleballCentral, the world’s largest pickleball store. The best part about being older entrepreneurs is having a wealth of experience and confidence. My husband is a serial entrepreneur and started his first business in college, over 30 years ago. Over the last 30 years, David has had varying degrees of success with his many business start ups. David’s successes and most importantly, his business failures have been a great education. David is skilled at seeing opportunities (i.e. baby boomers love pickleball) and evaluating risks (grow slowly, we tried growing quickly during the .com boom).

We’re both more mellow and relaxed due to our age. We live a balanced life, get lots of sleep and truly enjoy our small business and our lifestyle.”

Anna Copley, 52, David Johnson, 50, Owners, PickleballCentral

25) “I started this company about two years ago when my position as a General Manager for an automotive parts distributor was eliminated. I was one month shy of turning 50 and felt this was the best time to start my company as finding a similar job at my age might prove to be difficult. I began making food for my dogs about 4 years ago and always wanted to build a company around it. I truly enjoy the impact my food has on the lives of my customer’s and their dogs. I provide home delivery as an added service and as a way to get first hand feedback. I see in person how the dog’s coats are shinier, eyes are brighter, and teeth are whiter. This accompanied with happy owners keeps me inspired and motivated to continue this journey.”

Lisa Hennessy, 50s, Owner, Your Pet Chef

26) “I opened my business, Zest Business Consulting after working as a Business Coach and Business Development Manager for EMyth. This is my 5th venture into entrepreneurship. As a business consultant I find helping other small business owners create financial freedom and soul-satisfying lives is more rewarding than having success in any of the businesses I have owned and operated. This is pretty
much my dream job.

The best part of being an entrepreneur in my 50s is that I can reinvent the way that I do business at any time. I have the courage to take leaps of faith and I care a lot less than I used to what other people think about my choices. At 51, I am only halfway there. I can wait to see what the next 50 years brings for me and my business!”

Jennifer Martin, 51, Small Business Coach and Owner, Zest Business Consulting

27) “I left corporate as an executive to pursue a full-time teaching line at a great college in New Jersey in the year 2000. Shortly after that, I decided to launch my business. Since that time, I have been an executive, coach, trainer, keynote speaker, motivational speaker, and a host of other capacities. Real success came when I wrote my first book. That book led to my second and then, with the help of my 10 year old daughter, I wrote a children’s book. I enjoy lecturing in the classroom on the subject of management, fly around the country and in some cases, the world, sharing my knowledge of training and development with people that care.

The best thing about being 50 and being an entrepreneur is the capacity to develop the vast knowledge and expertise, something my younger competitors may acquire but for a 50 year-old, comes naturally. Keeping vibrant and young at heart. Having a great deal of energy and using it to help other as light bulbs go off and people become what they are meant to be.”

Michael Provitera, 54 years old, President, Motivational Leadership Training

28) “I started my business Pollen-8, right around the time I turned 50. Unlike many entrepreneurs in their 50s, I still have children (two boys, ages 11 and 15) at home. I love having the flexibility to manage my home life while still continuing to work. Working hard, learning new things every day, being challenged and not thinking of myself in terms of my age is what’s important to me. Having been in business for a long time, I can leverage my experience while learning about and using all the dynamic and exciting new ways to be successful through social media, content curation, inbound marketing and more.”

Lisa Gordon, 53, Partner and CEO, Pollen-8, LLC

29) “I am 58 years old and turned my hobby into a business. It is nice to be able to collectively use knowledge and experience I have accumulated in my life into my business. As a Ph.D biochemist I started off in cancer research. Family life led me to work part time in medical writing and later teaching anatomy & physiology. Herbs have been important to me all my life; I grew them, used them and learned about them. I started Sagescript Institute and do cosmetic formulating, manufacturing and cosmetic microbiology. Seven years ago I started my own line of cosmetics, Colorado Aromatics. Having adult children means less responsibility at home and thus more energy and time I can put into my business.”

Cindy Jones, 58, Owner, Sagescript and Colorado Aromatics

30) “It is wonderful to be an entrepreneur in my 50s because I can help more people and have the freedom in my schedule to pick and choose what I would like to be involved in. Because I was astute with my finances, I do not have some of the financial pressures that younger entrepreneurs often experience starting out.

I am very passionate about my keynotes and workshops and look forward to helping improve the lives of as many people as possible. I was blessed to be part of an inspiring high school basketball game with my team manager Jason (J-Mac) McElwain. J-Mac has autism and has learning disabilities. As a gift to him for his loyalty and commitment to our basketball program, I put him into our final home game. He shocked the world by scoring 20 points including 6 three pointers in the last 4 minutes of the game.

I have been giving keynotes and workshops part-time for last 8 years. I am excited to become a full-time speaker in July of 2014.”

Jim Johnson, 54, Teacher and Coach/ Speaker Workshop Trainer

Join the ranks of these smart and successful entrepreneurs with your own business! MyCorporation is here to help you get your small business off the ground and running. Leave a comment below, or give us a call at 1-877-692-6772!

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Deborah Sweeney

is the CEO of MyCorporation.com. MyCorporation is a leader in online legal filing services for entrepreneurs and businesses, providing start-up bundles that include corporation and LLC formation, registered agent, DBA, and trademark & copyright filing services. MyCorporation does all the work, making the business formation and maintenance quick and painless, so business owners can focus on what they do best.

One thought on “Experts Weigh In: I’m an Entrepreneur in My 50s

  1. I turned fifty in January. I’m one semester away from completing my MA in Liberal Studies. My BA is in the same. I stopped working in 1/08 to return to school in pursuit of the education I didn’t get when I was young. Unfortunately, I’m now in student loan debt of about $150,000, have not found a job and don’t see how in the world my degree is going to help me. However, a friend and I are planning to start and grow a business through Amazon and online selling. My friend has successful eBay experience and we are determined to make it happen. At fifty and having never done any kind of work except unskilled, backbreaking, deadend jobs, I really hope to succeed as an entrepreneur in this and future decades of my life.

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