Spotlight on Josh Winkelstein

Young Life

I was born in Buffalo New York in 1958 and lived there until the tender age of 10 when I was ripped away from my friends and school and transported with my family to Oakland California.  There I completed grade and junior high school before open enrollment allowed me to attend Berkeley High School in, well, Berkeley.  The BHS mascot was the Yellowjacket and like we always said: “take the High out of BHS and all you have left is …well, you get the picture.

Josh with IPDD Stefan Jenssen, his motorcycle, relaxing after retiring from I.T., and showing off his very large lizard.
Work and Volunteering

Recently I retired from 25 years in I.T. and now keep myself busy with Toastmasters and the American Brotherhood Aiming Towards Education (A.B.A.T.E.), a motorcyclist’s rights organization. For Toastmasters, my volunteer work includes W Division Director as well as Area 2 and Area 20 Director. For A.B.A.T.E. I am Region 8 Treasurer and Area Coordinator. As you can see, if it is volunteer labor I am wildly successful at it. Nevertheless, I work hard to ensure the members get what they pay for.


I play the guitar, like to tinker with anything with moving parts and wonder how I ever found time to work with all these clubs and hobbies. My wife and I have 2 cats and one very large lizard.

Biggest Challenge

The biggest challenge I have faced as W Division Director recently is getting volunteers from the clubs to fill spots in our COTs and speech contests.  It seems to me that most of the time it is the “Usual Suspects” who volunteer.  They tend to be experienced Toastmasters who have filled the roles before so they bring a lot of knowledge with them.  That’s a good thing but I’d still like to see new faces filling these important leadership roles.  What we need is a mix of newer and more experienced members so we can share the work together while learning new skills. Then more people will benefit and continue to share their knowledge. The more involved you get with Toastmasters, the more you get out of it.

Life Changing

Toastmasters has given me the opportunity to try out leadership roles that I neither sought nor experienced in my work career.  In the last 25 years I was primarily a “rube in a cube staring at a tube” which is the real life of a Software Developer. The job lead to a healthy dislike for meetings and I found that it was easier to do the work myself as opposed to trying to get help from others. Toastmasters taught me leadership skills and then given me the opportunity to develop those skills. I now really enjoy mentoring individual Toastmasters and working with clubs and even attending meetings!

Author: Anna Donahue, DTM

I joined Toastmasters in February, 2016 because I wanted to learn how to feel comfortable speaking in public and talking about my new art business called Since then I have given speeches to large and small groups, recorded webinars for online distribution and held workshops for artists who are interested in learning what I know about the "business of art." Toastmasters has helped me to become comfortable in any environment and to take on leadership positions with success. I had no idea how far Toastmasters would take me and was pleasantly surprised at how easy it was to learn and grow with the encouragment of fellow professionals. For the Toastmaster year of 2019-2020, I was awarded Toastmaster of the Year after taking on many leadership roles at the district level. 

Leave a Reply


Join Our Mailing List


First Name

Last Name