Jeremy Dubow is Prosperity Partners’ Chief Executive Officer. He manages the company and is responsible for its strategic direction, growth initiatives, and talent development. 

Mentioned on the Show:

• Find Jeremy Dubow on LinkedIn: https://www.linkedin.com/in/jeremydubow/
• Jeremy Dubow’s profile on the Prosperity Partners website: https://www.prosperityllc.com/personnel/jeremy-dubow/
• Listen to the People Business episode with John Block, CEO of Unity Partners: https://peoplebusinesspodcast.com/johnblock/

Timestamps

(00:00:00) – Introducing Jeremy Dubow on People Business

(00:03:13) – What is Prosperity Partners and what have you been through in the last 12-18 months?

(00:05:40) – How did you want to conduct your business that differed from the traditional “Big Four”?

(00:10:13) – Entrepreneur mindset: What’s the biggest surprise about running a business? 

(00:12:22) – How do you deal with hardships and setbacks in business?

(00:17:17) – What is it really like to be in business with a private equity firm?

(00:22:57) – What is your current strategy for recruiting and attracting talent? How does your business model work with today’s professionals? 

(00:28:42) – Culture and fit: what are the processes and challenges of integrating acquisitions?

(00:38:20) – How are effective teams created in these conditions? 

(00:44:47) – What role does offshoring play in your strategy and how does that impact company culture? 

(00:48:50) – What is the purpose of business?

Chuck Wisner has spent 30 years as a trusted advisor, coach, and teacher in communication, human dynamics, and leadership excellence. He has worked with leaders and their teams in Fortune 200 companies. He also trained in mediation and worked as a senior mediator affiliated with the Harvard Mediation Program at the Harvard Law School, and later, was associated with MIT’s Center for Organizational Learning. His book, The Art of Conscious Conversations – Transforming How We Talk, Listen, and Interact, explores how to heighten our awareness and become more conscious in our conversations.

Mentioned on the Show

• Learn more at Chuck Wisner’s website: https://www.chuckwisner.com/
• Get Chuck’s book, The Art of Conscious Conversations: https://a.co/d/hfPRSmK
• Connect with Chuck on LinkedIn: https://www.linkedin.com/in/chuck-wisner
• Listen to the People Business interview with Charles Feltman, author of The Thin Book of Trust: https://peoplebusinesspodcast.com/charlesfeltman/

Timestamps
(02:53) - What is the ‘ontology of language’?

(06:02) – The impact of worldview on the language we use. What is a ‘master story’?

(09:33) – How can we let go of worldviews or change a master story?

(13:15) – How can we contend with negative views of ourselves?

(15:54) – Opinion vs fact: What questions can we ask ourselves about the stories we tell?

(21:34) – How can we break negative patterns and form healthy, positive new patterns?

(24:47) - The four questions: how to explore our thinking during our reactions

(34:27) - Collaboration and collaborative conversations: What makes for good collaborators?

(43:18) - "Conversations are the one human universal tool that we share."

As founder of Lapin International, David Lapin advises executives worldwide on how to align business strategy with character and corporate culture with purpose. He is the author of Lead by Greatness and a practicing Rabbi. Raised in apartheid-era South Africa, David helped draft one of the world’s first formal corporate ethics codes. He now lives in Israel and travels frequently to the U.S. for client engagements.

Mentioned on the Show

• David Lapin’s company, Lapin International: https://www.lapininternational.com
• Learn more about the Lapin Leadership Fingerprint: https://lapininternational.com/lapin-leadership-fingerprint-lp/
• David’s book: Lead by Greatness – https://amzn.to/4kxb7gU 
• Connect with Rabbi Lapin on LinkedIn: https://www.linkedin.com/in/davidlapin
• Lapin International on LinkedIn: www.linkedin.com/company/lapin-international/ 

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• Connect with O’Brien McMahon on LinkedIn: https://www.linkedin.com/in/obrienmcmahon/
• Learn more about O’Brien: https://obrienmcmahon.com/

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Timestamps

(00:00) – Welcome to People Business

(02:14) – What’s it like being a Rabbi and working in the business world?

(06:00) – What kind of role does a Rabbi have outside of a temple? 

(10:36) – How does your expanded cultural perspective shape your work as a Rabbi?

(24:16) – What does Judaism say about business?

(28:07) – How does business build a healthy community?

(37:29) – How can we best be of service to others?

(41:38) – Purpose: Is finding our purpose a worthy pursuit or a distraction?

(51:32) – Do “better people” enjoy more success? What does it mean to be a better person?

(56:28) – What qualitative improvements can be expected when people are working ethically and aligned with purpose?

(58:08) – Final thoughts and how to contact David Lapin and Lapin International.

Kassi Kincaid is a leading expert in creative leadership. She is a speaker, trainer, and author committed to helping people leverage their creativity to lead with greater impact and innovation. As the visionary behind Book Days — an international children’s literacy initiative — Kassi has seen how creative thinking can turn small ideas into global movements. Her journey from building a grassroots literacy project to inspiring professionals across industries fuels her mission: to equip leaders and teams with practical creativity frameworks that spark innovation, increase engagement, and drive meaningful change. 

Mentioned on the Show

• Kassi Kincaid’s website: https://www.kassikincaid.com/
• Learn more about Book Days: https://www.bookdays.org/
• Connect with Kassi on LinkedIn: https://www.linkedin.com/in/kassi-kincaid-speaker
• The Edge of Creativity by Kassi Kincaid: https://a.co/d/hSVLMqN
• Listen to Kassi’s podcast: https://pod.link/1714322040

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• Connect with O’Brien McMahon on LinkedIn: https://www.linkedin.com/in/obrienmcmahon/
• Learn more about O’Brien: https://obrienmcmahon.com/

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Timestamps

(00:00) Welcome to People Business.

(00:19) Meet Kassi Kincaid: Creative Leadership Expert

(05:06) How do you define creativity?

(10:15) How did the Book Days initiative come about?

(14:55) Creativity in kids vs. adults.

(19:06) Intrinsic vs. extrinsic motivation.

(27:05) What role does rest play with creativity?

(35:24) How do we bring creativity into our workplaces? 

(42:50) Is creativity something that can be learned?

(52:55) How can creativity improve our work success?

(55:05) Contacting Kassi and final thoughts on creativity.

Internal communication strategist Alejandra Ramirez is a veteran culture builder with nearly two decades of experience helping organizations align message with meaning. She founded ReadyCultures to help leaders communicate in ways their teams can hear, trust, and act on. 

Mentioned on the Show

• Connect with Alejandra Ramirez on LinkedIn: https://www.linkedin.com/in/malejandraramirez
• Learn more about Alejandra’s internal communications firm, Ready Cultures: https://www.readycultures.com/
• Get Alejandra’s worksheet explaining her Head, Heart, Hands approach: https://www.readycultures.com/3h-framework
• Tim Ferris’ interview with Walter O’Brien (inspiration for the show, Scorpion): https://www.youtube.com/watch?v=BQ6IcUoXpzU

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• Connect with O’Brien McMahon on LinkedIn: https://www.linkedin.com/in/obrienmcmahon/
• Learn more about O’Brien: https://obrienmcmahon.com/

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Timestamps

(00:00) Welcome to People Business.

(02:44) Meet Alejandra Ramirez of Ready Cultures.

(04:30) What is a “third culture” and what communication challenges does that bring?

(08:01) Are there best practices in internal communications?

(17:52) What do managers need to know about delivering bad news?

(20:48) How can companies uphold a communication strategy and be transparent?

(25:50) How can companies have effective communications?

(28:33) Why is social connection so important?

(29:05) Why is it important to know our ‘why’?

(29:37) The importance of “EQ” at work.

(33:30) How do leaders get coached in communications?

(36:59) What does good preparation look like?

(40:25) Who delivers the news, especially bad news?

(51:38) How can company culture be created?

(54:38) How to contact Alejandra Ramirez and Ready Cultures.

George Watts is Chairman of Top Line Talent and a nationally recognized author, behavioral scientist, and senior executive. He coaches CEOs on how to build and lead formidable C-Suite teams and is the author of several books, including Becoming Your Own Business Coach and Becoming a Strategic Leader. His passion is inspiring people to mature their natural personality strengths.

Laurie Blazek is President and CEO of Top Line Talent and is coauthor of Becoming a Strategic leader and cocreator of the online Top Line Talent leadership development program. Her passion is to help people specifically define who they are when they’re at their best.

Mentioned on the Show

• The book, Becoming a Strategic Leader: Capitalize on the Power of Your Personality: https://a.co/d/09u6VTy
• Connect with George Watts on LinkedIn: https://www.linkedin.com/in/george-watts-1b8923181
• Connect with Laurie Blazek on LinkedIn: https://www.linkedin.com/in/laurie-blazek-4b7a592
• Learn more about TLT Coaching: https://www.tltcoaching.com/

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• Connect with O’Brien McMahon on LinkedIn: https://www.linkedin.com/in/obrienmcmahon/
• Learn more about O’Brien: https://obrienmcmahon.com/

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Timestamps

(0:00) Meet George Watts and Laurie Blazek.

(02:37) What are some of the limitations of leadership coaching?

(11:51) How do we avoid unhealthy comparisons?

(13:52) How can we understand our weaknesses and our "shadow"?

(17:26) The Big Five Personality Traits.

(28:21) How do we apply insights about our personality in our everyday lives?

(37:38) How do I bring these personality insights to my workplace?

(42:54) What are the differences between intrinsic and extrinsic motivations?

(44:59) How does the "shadow self" derail personal growth?

(46:49) How can the "shadow" help during performance reviews? 

(48:56) How can we use these personality insights in other personal areas of our lives?

(58:22) Where to learn more and get the book, Becoming a Strategic Leader

Julie Jones is a business protocol and etiquette expert, sought-after public speaker, corporate trainer, and educator. She is certified by the Protocol School of Washington. 

Mentioned on the Show

• Learn more about Julie’s work on her website, Today’s Professionals: https://www.todaysprofessionals.com/
• Julie’s profile on LinkedIn: https://www.linkedin.com/in/therealjulieajones
• Follow Julie on Instagram: https://www.instagram.com/therealjulieajones/

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• Connect with O’Brien McMahon on LinkedIn: https://www.linkedin.com/in/obrienmcmahon/
• Learn more about O’Brien: https://obrienmcmahon.com/

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Timestamps

(00:00) Introduction to Julie Jones.

(01:55) What is protocol and business etiquette?

(04:50) What's the difference between extroversion and connecting with others?

(06:34) What is involved in modern etiquette?

(11:00) Why do first impressions matter?

(19:53) What is your reaction to the idea of bringing your whole self to work?

(25:22) "Act as pretty as you look."

(28:28) Image vs. brand: what's the difference?

(35:34) How do you align your personal brand with the company brand?

(43:39) Values: show up for others; align with the company; seek what's best.

(44:41) How do we help others get what they want out of life?

(46:52) Where can people contact Julie Jones?

Dave Moore is a partner at Laner Muchin and the firm’s Employment Litigation Department Co-Chair. While Dave spends much of his time defending employers in employment litigation of all shapes and sizes, he has focused much of his 20+ years as an employer lawyer on keeping employers out of the courtroom. Dave has been recognized among Illinois Super Lawyers and Leading Lawyers in 2024 and 2025. Dave was also recognized by the National Law Journal as an Elite Trailblazer in 2022 for work with employers during the COVID-19 pandemic.

Mentioned on the Show

• Connect with Dave Moore on LinkedIn: https://www.linkedin.com/in/dave-moore-5b2b58a
• Dave’s profile at the Laner Muchin firm: https://www.lanermuchin.com/attorneys-david-moore
• Listen to the People Business episode with Cash Nickerson: https://peoplebusinesspodcast.com/cashnickerson/

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• Connect with O’Brien McMahon on LinkedIn: https://www.linkedin.com/in/obrienmcmahon/
• Learn more about O’Brien: https://obrienmcmahon.com/

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Timestamps

(00:00) – Welcome to People Business

(00:17) – Introducing Dave Moore, employment attorney

(04:37) – What are the most common employment legal issues? 

(08:59) – What are documentation best practices?

(15:22) – How do employers navigate Americans with Disabilities Act (ADA) accommodations? 

(21:11) – How do mental health ADA accommodations work?

(25:41) – What risks are associated with terminating an employee and what are best practices for termination?

(30:01) – When should a workplace contact their attorney?

(32:43) – Role-playing difficult conversations with clients?

(34:19) – Navigating remote and hybrid work policies

(38:12) – Addressing employee relocation and “secondary” jobs

(43:53) – Unionization: hearing whispers or is a campaign underway?

(52:14) – Are governmental changes impacting employment law? What trends are ahead?

(01:00:29) – Practical advice and closing thoughts

Amber Pandya loves to help people and businesses thrive. She proves this every day in her role as Senior Director of Employee Experience at G2, where she helps employees reach their PEAK. 

Mentioned on the Show

• Connect with Amber Pandya on LinkedIn: https://www.linkedin.com/in/amberpandya
• Amber’s profile on G2: https://learn.g2.com/author/amber-pandya
• PEAK—Performance; Entrepreneurship; Authenticity; Kindness. Learn more about G2 and their PEAK culture: https://company.g2.com/about

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• Connect with O’Brien McMahon on LinkedIn: https://www.linkedin.com/in/obrienmcmahon/
• Learn more about O’Brien: https://obrienmcmahon.com/

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Timestamps

(00:00) – Welcome to People Business

(02:23) – What do you do at G2?    

(03:34) – What is G2?  

(08:17) – What are the key differences and similarities between working in-house versus consulting?  

(12:55) – Please explain G2’s "PEAK" values?  

(19:16) – What organizational factors does Amber see as blockers to employee performance, either at G2 or in other companies?  

(24:34) – How easy or difficult is it to remove a process once it has been implemented at G2?  

(27:54) – How does G2 balance its Kindness value with a Performance-Driven culture?  

(33:03) – What does authenticity mean at G2? How do you think about bringing your "whole self" to work?  

(37:00) – How does G2 personalize and maintain its culture as it scales to a larger organization?  

(41:11) – What is an INPS (Inclusion Net Promoter Score), and how does G2 use it alongside other data?  

(43:36) – Why is the Net Promoter Score (NPS) considered valuable?  

(47:39) – Who creates the actionable steps in the Voice of the Employee report? How do they assist leaders in improving performance and experience?  

(48:41) – What AI system does G2 use to synthesize employee data?

(52:09) – Mic drop: What impact can HR have on business performance? 

Michael Cupps is a productivity expert who has been in technology sales and marketing for over thirty years. He learned the importance of productivity from an early age due to his upbringing on a farm in Texas, which taught him the value of hard work, prioritization, and managing time wisely. Michael applies these lessons to his work helping individuals and teams to make the most of their time and priorities. He is also the host of The Habit Architect podcast and founder of the Time Bandit. Michael’s book and mobile app, Time Bandit, is the ultimate guide for those looking to leave behind chaotic and unmanageable to-do lists and ultimately reclaim their time to live a more balanced and productive life.

Mentioned on the Show

• Learn more about Michael Cupps and his Time Bandit system, including the app, book, and his podcast. Website: https://www.timebandit.io/index
• Connect with Michael Cupps on LinkedIn: https://www.linkedin.com/in/michaelcupps
• Learn how to make GPT prompts work for you! Jeff Su and his video on making prompts: https://youtu.be/jC4v5AS4RIM?si=3eX0vE3_YvA_bLOs | Jodie Cook shares prompts for small business: https://www.jodiecook.com/chatgpt-prompts-for-entrepreneurs/
• Tricia Sanders on the People Business podcast: https://peoplebusinesspodcast.com/triciasanders/
• The Checklist Manifesto book: https://a.co/d/3W40pZB
• Addiction help at SMART Recovery: https://smartrecovery.org/

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• Connect with O’Brien McMahon on LinkedIn: https://www.linkedin.com/in/obrienmcmahon/
• Learn more about O’Brien: https://obrienmcmahon.com/

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Timestamps

(00:00) – Welcome to People Business

(02:04) – How did you become a time management expert?

(04:59) – What commonalities do you see in time management that doesn’t work? 

(06:59) – The Eisenhower Matrix explained.

(12:20) – Leveraging AI for productivity.

(17:01) – What advice can you give people on establishing habits? 

(25:56) – The value of accountability partnerships.

(34:49) – How the Eisenhower Matrix works in practice.

(38:15) – How can managers and staff have productive conversations about priorities? 

(43:52) – How can teams adopt effective habits?

(46:26) – Breaking addictive habits.

(51:17) – Contact Michael Cupps and final thoughts on habit building.