Making The Jump Into Small Business Ownership


My interview today is with Jeff Levy. Jeff is an author, coach and speaker. He mentors individuals who are interested in exploring self employment with an emphasis in franchising. His experience includes participation in new technology companies, leveraged buyouts, management buyouts, raising investment capital and coach to hundreds of startup ventures.  Jeff has coached over 160+ individuals who have become franchisees and has co-authored the book “Making the Jump – Into Small Business Ownership” which I highly recommend especially if you are wondering whether you are ready for entrepreneurship or not.

If you would like to contact Jeff you may reach him via email on or phone at 206-914-1107. You can also check him out online here Don't forget to buy his book here

Tayo Rockson: What is your story? How did you get to where you are today?

Jeff Levy: I like to consider my story in three chapters, the last still being written and hopefully the longest.  The first third was growing up in Brooklyn, NY mostly raised by a single mom, and for a time living with an aunt and uncle. There was family love but not much money or examples of achievement.  After an academically lackluster high school experience, I just barely got into a community college, that realization was a turning point; I needed to commit to working harder and making something of myself.  That led to graduating the community college with honors and going on to Fordham.  I learned I had a capacity for hustling and passion to learn. I consider my formal education the end of chapter one.  After Fordham, I began working for a company where the CEO was an amazing entrepreneur.  I marveled at his leadership and his lifestyle. He lived at the Mayflower hotel and drove a big Cadillac.  I met my first mentor working at that company.  From there I fashioned myself as someone who would never give up and I was always on the lookout for opportunities. That led to a job for a west coast company that was soon acquired by a mega company, American Hospital Supply. My loyalty and achievements were rewarded as I was made a general manager, running the NY office.  I had various management positions with increasing responsibilities and I was learning all the time primarily from entrepreneurs.  I could see a pattern emerging and I was ready to take risks for the potential of bigger rewards. Chapter three began in my thirties when my wife, children and I sold all our possessions and moved to Seattle to participate in a startup.  I never looked back.  Since that time I have participated in tech startups, management and leveraged buyouts, mergers, acquisitions, significant raising of capital and franchising.   In this third chapter, I have evolved my interests along the lines of coaching, authorship and teaching.  Life is good and the best is yet to come.  Today, I coach individuals interested in self-employment, shamelessly promote my book, teach and do a fair bit of guest speaking.

TR: What was your lemonade stand moment? When did you realize you wanted to get involved with business?

JL: I have had several lemonade stand moments and I love this question.   From my best recollection, here are the comments made that caused me to think entrepreneurially and who said them to me:

  1. It is now time for you to be a mentor, My wife, circa 2002
  2. You really need to be in your own business, Board member 2002
  3. The first time I realized that I was not happy with politics and I always felt that I could do a better job if left to my own goals and strategies, Circa 1976
  4. When I realized the relationship between “risk and reward” and the difference between an “expense and an investment.” Circa 1985
  5. When I realized I was a hard core optimist and what others may see as lemons, I saw as lemonade.  Most of my adult life.

TR: When you hear the word entrepreneurship, what do you think of?

JL: I think of freedom to be the best I can be and the means to get the best return for my time and resources invested. It is not only economic return, but living a life that others regard as special and would admire. In my presentations I always quote this anonymous definition of entrepreneurship and believe it completely:  “Entrepreneurship is living a few years of your life like most people won’t, so you can spend the rest of your life like most people can’t.” ~ Anonymous

TR: With your journey as an entrepreneur, what are the essential skills you have found crucial to know? 

JL: In order of importance: Working harder than most are willing to do; strong interpersonal skills,  effective forecasting and plan development, being intentional and knowing where I will get the best ROI for my time, realizing that money is a bi-product and I need to be passionate about the work and most important,  knowing my limitations. Never give up if you believe in the idea.

TR: When did giving back become part of your story?

JL: I believe the seeds of giving back, were originally planted during my time at Fordham.  Even though I worked and went to school, I joined the Maroon Key Society that was a community service organization at the school. I was saddened to know it no longer exists.  At 53 years old, about ten years ago, a career challenge had me choosing between values and money.  I chose values and began an introspective journey that resulted in developing my personal goals, needs and objectives that I use every day to guide my decisions.  I consider giving back as a core value.  I am the third most senior mentor at the Seattle U business school (serving 18 years)  and I would need several pages to list my volunteer activities and memberships.  Amongst the many, many organizations I serve, I am very proud to be a “Fellow of the Fordham Consortium on Business.”

TR: Why do you think it is important to give back?

JL: I am a big believer in legacy. I believe that we hold the power to create heaven or hell on earth, depending on what we do. I chose to use what I have learned and my guiding principles to try and make this world a better place.

TR: What advice do you have for entrepreneurs out there?

JL: My best advice to you entrepreneurs is to create an objective mindset that can evaluate if you are ready. Many things need to be in place to be capable and prepared to launch your own venture. Life is a long journey and you will have several bites at the apple.  Make sure you have developed basic business competencies in forecasting, human capital management, finance, technology, customer identification, acquisition and service.  If you don’t have these strengths, identify people for your team that do.  Once you are ready, make sure you have family support. And in the words of Winston Churchill, “Never, never, ever give up.”  And of course, read my book!!


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Tayo Rockson

Tayo Rockson is a storyteller, cultural translator, and brand strategist for change-makers on a mission to use his difference to make a difference.  He is a 4x TEDx speaker, the CEO of UYD Management, and the host of the As Told by Nomads podcast. In addition to that, he's been named a "Top 40 Millennial Influencer" by New Theory magazine. His book Use Your Difference To Make A Difference is based on how to connect and communicate in a cross-cultural world.

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