Episodes

Sept. 2, 2025

#262 - Risk Management with Scott Heinila, CEO of Optimized Insurance

Risk Management with Scott Heinila, CEO of Optimized Insurance Hosts Brad Wright and Michael Connaughton are joined by Optimized Insurance CEO, Scott Heinila. After graduating from California State University Long Beach (CSUL...
Aug. 26, 2025

#261 - Angel Investing with Stephen Schweich

Stephen Schweich Host Michael Connaughton is joined by Stephen Schweich. Stephen is Chairman of the Cherrystone Angel Group and held a 30 year career in Investment Banking. Stephen has been an active investor in venture capit...
Aug. 19, 2025

#260 - Paw-sitive Planning: Estate Planning for Your Pets – with Liza Connelly

Paw-sitive Planning: Estate Planning for Your Pets – with Liza Connelly Kathleen speaks with Liza Connelly, director of trust and estate services for CIBC Private Wealth. Liza has more than 25 years of trust, estate and fiduc...
Aug. 12, 2025

#259 - From Confused to Confident: Helping Families Navigate Aging with Parker Polidor

From Confused to Confident: Helping Families Navigate Aging with Parker Polidor Kathleen and Kevin speak with Parker Polidor, co-founder of CareAlly. CareAlly is a turnkey software solution that financial advisors can use to ...
Aug. 5, 2025

Wallets and Waistlines with Reyna Gobel

Kathleen and Brad speak with freelance journalist, keynote speaker, and nutrition educator Reyna Gobel. Reyna is a nationally recognized expert in college funding, student loans, and financial wellness who brings a unique bac...
July 29, 2025

#257 - 5 to 9 Things You Don’t Know About 529 Plans with Chris Stack

5 to 9 Things You Don’t Know About 529 Plans with Chris Stack Hosts Brad Wright and Kevin Williams are joined by attorney and consultant, Chris Stack. -Chris is managing consultant, Savingforcollege.com, is a nationally recog...
July 22, 2025

#256 - Breaking Money Silence with Kathleen Burns Kingsbury

Breaking Money Silence with Kathleen Burns Kingsbury Kathleen and Kevin speak with money psychology expert Kathleen Burns Kingsbury. Kathleen is the founder of KBK Wealth Connection and a leading voice on women and money and ...
July 16, 2025

#255 - Navigating Egos and Emotions During the College Planning Process – With Jack Wang

Navigating Egos and Emotions During the College Planning Process – With Jack Wang Hosts Kathleen Kenealy and Michael Connaughton speak with Jack Wang, a nationally recognized college funding expert who helps families answer t...
July 11, 2025

#254 - The Human Side of Wealth: Navigating Family Dynamics – with Emily Bouchard

The Human Side of Wealth: Navigating Family Dynamics – with Emily Bouchard Kathleen and Brad speak with Emily Bouchard, founder of Bouchard Bespoke Consulting. Emily is a Chief Learning Officer and Family Dynamics Advisor for...
July 2, 2025

#253 - Bringing the Human Element Back to Human Resources – with Angela Sarver

Bringing the Human Element Back to Human Resources – with Angela Sarver Hosts Kathleen Kenealy and Kevin Williams are joined by Angela Sarver, founder of EllieBlu HR Consulting. Angela is a human resources expert who speciali...
June 24, 2025

#252 - FIRE for Dummies Author Jackie Cummings Koski on Financial Independence

Host Brad Wright is joined by Jackie Cummings Koski. Jackie is the author of FIRE for Dummies and co-host of the Catching Up to FI podcast, focused on financial independence for late starters. She serves as Chapter President ...
June 18, 2025

#251 - Paul Gaudio-President NexGen FPA-Client guidance and network expansion opportunities.

Paul Gaudio Host Michael Connaughton is joined by Paul Gaudio. Paul is a CFP® and Client Advisor at Crestwood Advisors with 8 years of experience helping individuals and families make smart choices with their money. Paul is p...
June 12, 2025

#250 - Dan Galli & Dennis Moore- Catching up with FPA Leadership

Catching up with FPA Leadership - with Dan Galli & Dennis Moore On this episode Kathleen and Kevin are joined by FPA national president-elect Dan Galli as well as long-time member, supporter and now acting CEO of FPA National...
June 3, 2025

#249 - What you need to know about Reverse Mortgages with Stephen Pepe

On this episode of the Wicked Pissah Podcast , we are joined by Stephen Pepe of Longbridge Financial, L LC, where he is a top producing Loan Officer , Reverse Mortgage Consultant and industry expert in r everse m ortgages. St...
May 27, 2025

#248 - Reassuring Clients About Social Security – with Marcia Mantell

Reassuring Clients About Social Security – with Marcia Mantell On this episode, Kathleen and Kevin speak with Social Security and retirement planning expert Marcia Mantell to talk about how clients’ anxiety about Social Secur...
May 20, 2025

#247 - Federal Employee Retirement Benefits Explained: Insights from Micah Shilanski, CFP®

If you’ve seen the news this year, you know why we wanted to talk about this topic. Whether DOGE layoffs or early retirements or concerns about future job security, Federal employees may be looking to financial advisors for ...
May 13, 2025

#246 - Jordan Jackson, J.P. Morgan Global Market Strategist: Tariffs, Trade and Taxes… Oh My!

Jordan Jackson, J.P. Morgan Global Market Strategist: Tariffs, Trade and Taxes… Oh My! Hosts Kathleen Kenealy and Kevin Williams are joined by JP Morgan Global Market Strategist, Jordan Jackson. Jordan is an Executive Directo...
April 30, 2025

#245 - Jeff Johnson, Appleton, and Fixed Income Markets

Jeff Johnson Hosts Michael Connaughton and Brad Wright are joined by Jeff Johnson, Senior Vice President of Appleton Partners. Jeff is a member of Appleton’s Fixed Income Investment Committee and is responsible for business development and managing...
April 22, 2025

#244 - John Finney - Overvue and how it creates client and advisor efficiency

John Finney Host Michael Connaughton is joined by John Finney Co-Founder Overvue. John Finney is the co-founder of Overvue, a software company that helps financial advisors streamline their client onboarding. Before starting Overvue, John spent over...
April 15, 2025

# 243 - Andy Ives– Navigating Net Unrealized Appreciation (NUA) Strategies

Andy Ives, CFP®, AIF® – Navigating Net Unrealized Appreciation (NUA) Strategies Host Chris Boyd is joined by Andy Ives, CFP®, AIF®, an IRA Analyst at Ed Slott and Company, LLC, to delve into the intricacies of Net Unrealized Appreciation (NUA)...
April 1, 2025

#242 - Joy Slabaugh; The Financial Conflict Resolution Institute

Hosts Michael Connaughton and Kathleen Keneally are joined by Joy Slabaugh founder of The Financial Conflict Resolution Institute. Joy is a CFP® professional with 20 years financial of planning experience that includes providing advice to...
March 25, 2025

#241 - Keith Garte talks Personal Risk Management and answers advisors questions

Keith Garte Hosts Michael Connaughton and Kathleen Keneally are joined by Keith Garte, Personal Risk Management Advisor with Assured Partners. Keith Garte is a Personal Risk Management Advisor with Assured Partners working out of their Natick...
March 18, 2025

#240 - Advisor Tech with Jump Advisor AI CEO Parker Ence

Advisor Tech with Jump Advisor AI CEO Parker Ence Hosts Brad Wright and Kevin Williams are joined by Parker Ence, CEO and cofounder of Jump Advisor AI. Parker is an entrepreneur and operator with 12 years CEO/cofounder experience across advisor tech,...
March 11, 2025

#239 - From Office to Anywhere: Erica Feldblum of LPL

Have you thought about making your business fully remote?  Or perhaps it is and you’ve wanted to relocate?  That’s the story of today’s guest, Erica Feldblum, and LPL advisor, on this week’s episode of the WPP.  Listen in has...