Bootstraps
Bootstraps
Podcast Description
Welcome to the podcast for navigating this wild, apocalyptic rollercoaster ride we're all on! And no, I'm not being dramatic — the actual definition of apocalypse means "to uncover." And whew, haven't we all been uncovering a lot lately? Old wounds, new anxieties…But here's the good news ~ the magic is in the mess.
This podcast was inspired by the “McDago” tribe of Irish-Italian, tough, tender, funny-as-hell FAMIGLIA who taught me: “Fall down? Fine. But come back swingin' - with fire, laughter, grace, and maybe a meatball in each hand!”
My Italian Nonna’s motto? “Pull up your bootstraps.” She lost her mother young, was raised by her Italian immigrant father (a Chicago chef), but still showed up swinging! She worked with passion til age 85, & lived to 97 with sass and incredible stamina. My own parents are also vibrantly bootstrappin’ through their 80’s…Proving strength & grit don't retire. Now I'm here to share that spirit with you! I'm a Mom, therapist, yoga instructor, sound healer, & musician (who dabbles in stand-up comedy).
The Italian chef gene skipped me, but I do serve up healing—spiced with humor, creativity, and a dash of sass. Welcome to the FAMIGLIA!
Pull up those bootstraps…
Let’s do this!
All episodes produced by Lisa Whittingham and Brad Dickert
Edited and mixed by Brad Dickert
We want to hear from YOU!!
Do you have an inspirational “Bootstraps” story you’d like to share? Or are you struggling with an issue / need advice / tools from Lisa?
Write to us at:
[email protected] or
DM Lisa on IG :@sita_whitt
Podcast Insights
Content Themes
Explores themes of resilience, personal growth, and navigating life's challenges, with episodes delving into topics like overcoming adversity, the importance of humor in tough times, and spiritual growth. For example, a recent episode examines 'apocalyptic times' through an uplifting conversation with an intuitive guide.

Welcome to the podcast for navigating this wild, apocalyptic rollercoaster ride we’re all on! And no, I’m not being dramatic — the actual definition of apocalypse means “to uncover.” And whew, haven’t we all been uncovering a lot lately? Old wounds, new anxieties…But here’s the good news ~ the magic is in the mess.
This podcast was inspired by the “McDago” tribe of Irish-Italian, tough, tender, funny-as-hell FAMIGLIA who taught me: “Fall down? Fine. But come back swingin’ – with fire, laughter, grace, and maybe a meatball in each hand!”
My Italian Nonna’s motto? “Pull up your bootstraps.” She lost her mother young, was raised by her Italian immigrant father (a Chicago chef), but still showed up swinging! She worked with passion til age 85, & lived to 97 with sass and incredible stamina. My own parents are also vibrantly bootstrappin’ through their 80’s…Proving strength & grit don’t retire. Now I’m here to share that spirit with you! I’m a Mom, therapist, yoga instructor, sound healer, & musician (who dabbles in stand-up comedy).
The Italian chef gene skipped me, but I do serve up healing—spiced with humor, creativity, and a dash of sass. Welcome to the FAMIGLIA!
Pull up those bootstraps…
Let’s do this!
All episodes produced by Lisa Whittingham and Brad Dickert
Edited and mixed by Brad Dickert
We want to hear from YOU!!
Write to us at:
DM Lisa on IG: @sita_whitt
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.

Disclaimer
This podcast’s information is provided for general reference and was obtained from publicly accessible sources. The Podcast Collaborative neither produces nor verifies the content, accuracy, or suitability of this podcast. Views and opinions belong solely to the podcast creators and guests.
For a complete disclaimer, please see our Full Disclaimer on the archive page. The Podcast Collaborative bears no responsibility for the podcast’s themes, language, or overall content. Listener discretion is advised. Read our Terms of Use and Privacy Policy for more details.