Boomer Think Thank: Late Entrepreneurship

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On our second Boomer Think Tank, we focused on late entrepreneurship, and specifically on the risks and rewards that Boomers encounter when joining or creating their own business. The Recession had a huge impact on every generation; with Boomers it may have been one of the catalysts for late entrepreneurship.

In the study “The Coming Entrepreneurship Boom,” the Ewing Marion Kauffman Foundation reports that from 1996 to 2007, Americans between the ages 55 and 64 had a significantly higher rate of entrepreneurial activity than those ages 20 to 34. While the majority of start up investors are Boomers, it is interesting to see the number of entrepreneurs who are also Boomers.

This week our panel included:

  • Jewel Fryer – business owner and property investor
  • Bev Lesnick – coffee house owner, investee, and secondary entrepreneur
  • Mark Babbitt – has been involved in three start ups, most recently UTurn &
  • Bhupesh Shah – has his own start up, Ethnicomm Inc.

You can view the hangout in its entirety here, or read on for a recap:

Each of our panelists have started their own businesses, and each has experience in working in the corporate sector. When asked what made them try the start up world, the group agreed with Mark’s sentiments:

I guess I’m an addict now. I tried the corporate world as an engineer for eight years, and threw my hands up one day and said, “this pretty much sucks” and didn’t want to live like this anymore.

Consideration of risk

Each of our participants were incredible aware of the risks they took starting from the ground up. Creating a start up later in life wasn’t just about their own entrepreneurial spirit or being the master of their own destinies; it’s about your partner, family, reputation, personal brand, and how you are perceived in the world.

Severity of Failure

Bev was quite clear on where she stood on failure:

We talk about how failure is the best teacher, but failure freaking sucks.

Having the extra considerations that come with age changes the level of severity of failure. Both Bev and Jewel talked about having a shorter amount of time to succeed and how they both did not want to start over.  And while Mark doesn’t believe that Boomers have less time to succeed, he cautions himself in the most pragmatic way possible: what are the opportunity costs and am I becoming the person I left the corporate world to avoid?

Responses by Family and Friends

Each of our participants described how their family and friends responded to their decision to start their own businesses.  Bhupesh said he is now this expected to prove your genius.  Bev said all of her friends thought she was insane. Mark’s father does not “get” what Mark does and does not want to get it; it is baffling to Mark’s father why someone wouldn’t want the 40/40/40 (40 years at the same company, 40 hours a week, with a 40% discount on your pension) plan.  Jewel put it best:

My mother is still hoping that I get a job that has a good pension and no one understands what I do. It’s very isolating and everyone expects you to do things as they used to be done, and instead you are doing what the young kids are doing. It’s weird and uncomfortable for them [the silent generation].

Industry Networks

The panelists all endured questionable responses from friends and family, which served to highlight the necessity of having a web of people who get and understand their journeys in the start up world.  Bhupesh initially created a community out of former corporate contacts, but over time the Internet became his greatest resource for support.  For him, Facebook groups are the best places to get information or bounce ideas off of other people. He adds,

I wouldn’t go to the Chambers of Commerce to ask questions, but I have no problem doing this online.

Jewel agrees that the groups have been huge lifelines and have created meaningful relationships with other late entrepreneurs.  She goes on to say

Since we’re all isolated, it’s great that we have these groups of people to connect with and talk about our journeys.

Mark summed it up best:

I learn so much from the social environment, and when you go to the conferences and events, and you already know people because it’s like you’ve known them your whole life because you met them online! We’re all supporting each other even though we’ve never met face-to-face.


  • The idea of a calm, lazy retirement was not something any of our Boomers wanted or expected.
  • Entrepreneurship is NOT the domain of they young; our Boomers were willing to take great risks too.
  • Having a network of other Entrepreneurs is essential, because most of our Boomers’ real life networks didn’t really understand the journey they embarked on.
  • Failure sucks at any age, and it is the risk of every entrepreneur. It isn’t stopping Boomers from trying.

Join us on March 11th, 2015 at 8:00 pm EST for our next BTT on Ethical and Social Responsibility.

photo credit: The merits of failing faster via photopin (license)

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