EP – 105 Grandpas Starting or growing a Side Business

Our conversation with James Divine

James ‘Papa Jimmy’ Divine is back to discuss his experience creating multiple side businesses while working full-time as a band teacher in a Title 1 school. James talks to us about his journey from transitioning from the U.S. Army to becoming a music teacher and the process it took to earn his Master’s in Music Education while in the Army and raising a family.

We get into an interesting conversation about the mindset of starting side businesses. How grandfathers can find the time to write a book or create a course. We also discuss mentors and coaches we have used to help us to get clarity about what businesses or projects we are involved in. As part of our discussion about mentors, we listen to Dan Miller’s 48 Day’s podcast and Dave Ramsey’s radio program. James and I also went through Chris LoCurto’s Next Level Life event.

James is incredibly open and honest in talking about how he has worked and continues to work on overcoming a negative mindset. The mindset was part naturally occurring and part of the environment that he grew up in. James outlines a great way to overcome or improve your negative mindset. His number one piece of advice is to “keep moving forward.”

After you have listened to this episode, please remember to like and subscribe to the show if you haven’t already. It would also be fantastic if you would share this podcast with a friend. Sharing is the best way to help me spread the word about the importance of grandfathers in the lives of their grandchildren and families.


Here is the link to my previous conversation with James Divine (Episode 13): A Cool Teacher Dedicated to Helping Young People Succeed.

James has generously offered the listeners of this episode an 50% discount on any of the products in his store IF you use the discount code COOL GRANDPA. Click HERE to go directly to James’ store and take advantage of this awesome deal!

Click HERE to visit James’ website and see all his great products and services. You can also connect to James on social media and email by clicking those links on James’ website.

Click HERE to visit Ramsy Solutions, learn more about Dave Ramsey, and listen to his daily radio program.

Ready to check out Make Momentos? Click HERE to be taken to a landing page created just for you.

To Join Dan Miller’s 48 Days Membership group (I am a part of this group), you need to sign up for the waiting list. Dan only opens up the group for short periods. To reserve your spot in the 48-Days community, click HERE.

Click on this link to learn more about Peekabond.

Click on this link to learn and sign up for Readeo.

Affiliate Links

These are links to products and services that I highly recommend AND use. I do get a percentage of the purchases you make.

More than GrandMore Than Grand is an excellent resource for new grandparents AND parents. Listeners of The Cool Grandpa Podcast enjoy 10% off any fantastic products that More Than Grand provides by entering COOLGRANDPA10 at checkout. To visit More Than Grand, click HERE.

Intentional Grandfathering MasterclassGrandfathers have a unique and meaningful role to play in grandchildren’s development, yet they often find themselves behind the scenes, on the sidelines, or less engaged than they’d like to be. This masterclass delivers a playbook for helping grandfathers level up their influence and impact. Listeners to The Cool Grandpa Podcast can receive 40% off this course by using Cool40 at checkout.

Grandparents academyFounded in 2011 by Aaron Larsen as a way to honor his grandparents, GrandparentsAcademy.com is the world’s first and only online academy dedicated to helping grandparents grow meaningful relationships and rich legacies with their loved ones.

My Grandpa’s Grandpa

When it is time for bed, Charlie’s grandpa tucks Charlie in. Charlie asks his grandpa many questions about his grandpa’s grandpa. Charlie’s grandpa shares a magical moment as he introduces Charlie to his great-grandpa through fun memories.


This is my children’s book that was created to entertain and inspire conversations about other family members that the children may not have had the opportunity to have met. – TO CELEBRATE FATHER’S DAY, I AM OFFERING A LIMITED-TIME DISCOUNT OF 20% FOR “MY GRANDPA’S GRANDPA”



If you prefer an eBook, you can download the Kindle version by clicking on this LINK.

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