The 1958 Lawyer

Gregg Garofalo: Building a Tech-Forward, Human-Centered Estate Practice

Episode Summary

What happens when a probate and estate planning lawyer becomes a tech innovator and special needs advocate? In this episode, you’ll hear how one attorney rebuilt his practice around Microsoft tools, remote work, and deeply personal experience to create a leaner, more sustainable firm that truly serves families. What does it really look like to build a law firm that grows with your life instead of consuming it? How do you balance scaling a practice with staying lean and sustainable? What happens when personal experience shapes your legal niche in a meaningful way? How can technology—especially tools like Microsoft Power Apps—transform the way a firm operates? What role should AI play in modern legal work without compromising ethics or judgment? When does growth become a liability instead of an advantage? How do external market forces unexpectedly reshape a legal practice? What’s the smartest way to invest in marketing early on? How can remote work actually improve both client service and quality of life? What’s one shift that can make running a firm feel lighter and more intentional? That’s all for today! Big thanks to Gregg Garofalo for sharing how he reimagined his practice through technology, personal conviction, and a commitment to serving families with care. From navigating market shifts to building custom tools and embracing remote work, his journey offers a refreshing take on what a sustainable law firm can look like. About Gregg Garofalo: Gregg Garofalo is a legal professional whose practice focuses on probate, estate planning, and real estate, with extensive experience serving as a court-appointed guardian ad litem for the Circuit Court of Cook County across multiple divisions, including probate, domestic relations, and law. He is an active leader within the legal community, having held key roles in both the Illinois State Bar Association and the Chicago Bar Association, where he previously served as Chair of the Probate Practice Committee and now holds Ex-Officio positions. In addition to contributing to the ISBA’s Trusts & Estates Council and mentor program, he is a frequent speaker on probate and estate matters. Beyond his legal work, Gregg is deeply involved in civic and professional organizations, supporting initiatives such as the Children’s Assistance Fund and the Illinois Bar Foundation, and serving in leadership roles with groups including the Justinian Society of Lawyers and the Italian American Political Coalition. Connect with Gregg Garofalo: Website: https://glgfirm.com/ LinkedIn: https://www.linkedin.com/in/gregg-garofalo/ Connect with Ron Bockstahler: Email: ronb@amataoffices.com LinkedIn: https://www.linkedin.com/in/ronbockstahler/ Company website: https://amatacorp.com/ “Don't Lose Your Balance” book: https://www.amazon.com/Dont-Lose-Your-Balance-Business/dp/1964046467 Connect with Rebecca Bockstahler: LinkedIn: https://www.linkedin.com/in/rebecca-bockstahler-aa786b2a6/ Show notes by Team Podcastologist Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.

Episode Notes

What happens when a probate and estate planning lawyer becomes a tech innovator and special needs advocate? In this episode, you’ll hear how one attorney rebuilt his practice around Microsoft tools, remote work, and deeply personal experience to create a leaner, more sustainable firm that truly serves families.
 

That’s all for today! Big thanks to Gregg Garofalo for sharing how he reimagined his practice through technology, personal conviction, and a commitment to serving families with care. From navigating market shifts to building custom tools and embracing remote work, his journey offers a refreshing take on what a sustainable law firm can look like.
 

About Gregg Garofalo: Gregg Garofalo is a legal professional whose practice focuses on probate, estate planning, and real estate, with extensive experience serving as a court-appointed guardian ad litem for the Circuit Court of Cook County across multiple divisions, including probate, domestic relations, and law. He is an active leader within the legal community, having held key roles in both the Illinois State Bar Association and the Chicago Bar Association, where he previously served as Chair of the Probate Practice Committee and now holds Ex-Officio positions. In addition to contributing to the ISBA’s Trusts & Estates Council and mentor program, he is a frequent speaker on probate and estate matters. Beyond his legal work, Gregg is deeply involved in civic and professional organizations, supporting initiatives such as the Children’s Assistance Fund and the Illinois Bar Foundation, and serving in leadership roles with groups including the Justinian Society of Lawyers and the Italian American Political Coalition.
 

Connect with Gregg Garofalo:

Website: https://glgfirm.com/

LinkedIn: https://www.linkedin.com/in/gregg-garofalo/

 

 

Connect with Ron Bockstahler:

Email: ronb@amataoffices.com

LinkedIn: https://www.linkedin.com/in/ronbockstahler/

Company website: https://amatacorp.com/

“Don't Lose Your Balance” book: https://www.amazon.com/Dont-Lose-Your-Balance-Business/dp/1964046467

 

Connect with Rebecca Bockstahler:

LinkedIn: https://www.linkedin.com/in/rebecca-bockstahler-aa786b2a6/


Show notes by Team Podcastologist

Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.