This week Lisa sits down with someone very close to her heart — her oldest nephew Bobby Whittingham, the 4th generation carrying forward the legacy of Whittingham Meats, a South Side Chicago family business, built from pure hustle and grit.
The story goes way back, to Lisa's grandfather Dixie, who went from working the deli counter at "the Jewel," to buying a refrigerated truck for 100 bucks from a guy at a bar, and literally driving restaurant to restaurant selling meat out of the back. Today, the Whittingham name is part of South Side Chicago history, even appearing on a sign in right field at Chicago White Sox "Comiskey Park."
But long before business and responsibility, Bobby was just a kid playing with toys in his Italian Nonna's "frunchroom", where family stories, traditions, and values quietly took root.
Bobby & Lisa reminisce on stories from the front lines of the "Pandorama" in 2020. When the world shut down, Bobby stepped up with a brilliant pivot: creating the now-legendary "Corona Care Package," helping the family business adapt overnight and continue serving the community during one of the most uncertain moments in modern history. It was a powerful reminder that sometimes leadership shows up not with a title, but with creativity, instinct, and courage.
In this conversation, Bobby also shares:
- Why he's a strong advocate for therapy and self-awareness.
- How becoming a father soon is reshaping the way he thinks about legacy — not just in business, but in life.
Bobby embodies the Bootstraps Boogie mindset — trusting your intuition, adapting when life throws curveballs, and not waiting for the storms to stop, but learning how to dance in the rain.
***
- Visit whittinghammeats.com for any of their seasonal packages, value packages or any of the amazing meat products they offer, and get FREE delivery on orders of $150 or more.
- Follow Bobby on Instagram @Bobwhitts
***
Therapy resources:
https://www.phylliskrystal.com/
If you or a loved one is struggling with traumatic memories/PTSD, this therapy is very effective:
https://www.emdr.com/what-is-emdr/
Lisa is an EMDR-trained Therapist, and a Certified Music & Sound Practitioner::
https://www.lisawhittinghamlcpc.com/
Contact Lisa: DM Lisa on IG: @sita_whitt or email: [email protected]
***
🎶 Bootstrap Boogie Playlist 🎶
https://youtube.com/playlist?list=PL-KL5XY5Cjvo99189zwS-JNuMSKUtw31_&si=CueyFzWUUkcrUfvC
***
We want to hear from YOU!!
Write in with stories of people you admire for their courage, creativity, leadership. [email protected]
or
DM Lisa on IG: @sita_whitt
***
DISCLAIMER:
The Bootstraps podcast is for informational and entertainment purposes only. It is not intended to be a substitute for professional mental health treatment, therapy, diagnosis, or advice. Thecontent presented reflects the personal views and opinions of the host and/or guests and should not be considered clinical or therapeutic guidance. Listening to this podcast does not establish a therapist-client relationship between you and the Host, Lisa Whittingham, LCPC, or any of the guests featured on the show. If you are in need of mental health support, please consult a licensed professional in your area. By listening to this podcast, you agree not to hold the host, guests, or any affiliated parties liable for any psychological, emotional, legal, or physical harm or damages that may arise from the content or discussions shared on the show. If you are experiencing a mental health crisis or emergency, please contact emergency services or a mental health professional immediately.