What started as chest pains during a yoga class led to emergency open-heart surgery and a year-long recovery that nearly derailed Matthew Grishman's financial planning practice and personal health. As a successful wealth manager and co-owner of Gebhardt Group, Inc., he thought he had comprehensive planning covered—until he faced one of the "5 D's" that can devastate any business: Diagnosis.

Despite having built a thriving wealth management firm with his business partner Jim Gebhardt, they found themselves scrambling at the 11th hour to protect their practice and financial security. The grueling 12-month recovery from surgical complications gave Matthew firsthand experience of just how vulnerable even financial professionals can be when life throws a curveball.

They were fortunate—their practice survived and their clients continued to receive exceptional service. But statistics show that nearly 50% of business owners will face one of the 5 D's (Death, Diagnosis, Divorce, Disagreement, or Distress), and many won't be as lucky as they were.

This experience completely transformed Matthew's professional mission. As a wealth manager who lived through this crisis, he now brings a unique perspective to helping fellow business owners and professionals prepare for life's inevitable transitions before they become emergencies. That unexpected medical event didn't just save his life—it reinforced the critical importance of comprehensive business protection and succession planning that goes beyond traditional financial planning.

Today, Matthew and Jim are dedicated to helping entrepreneurs and business owners safeguard their financial assets and ensure their legacy survives whatever life throws their way—because sometimes even the experts need protecting too.

 Why do some of the most wealthy individuals have Captive Insurance? Get a write-off, reduce taxes, make a loan are just some of the things that make Captive Insurance an attractive strategy for business owners. 

The June 2024 US Supreme Court Connelly decision has had a large impact on using entity purchase plans, particularly those funded with life insurance.  The Connelly court ruled that the estate tax value of a company – and hence, the value of the deceased owner’s interest as well – is not reduced by the company’s obligation to redeem a deceased owner’s interest. This presentation discusses Connelly, its implications (including for those who are well below the estate tax exemption), and some potential workarounds.

Dan Finn is a 1994 graduate of the University of Wisconsin law school. He has over 25 years of experience helping clients and their advisors in the realms of business, estate, and retirement planning. Since late 2023, Dan has been a Director in Principal’s Business and Advanced Solutions division, where he assists financial professionals and their clients with buy-sell agreements, nonqualified deferred compensation plans, and related business topics. Before joining Principal, Dan had spent 25 years with Northwestern Mutual, where as a senior director in the advanced planning area, he consulted with advisors, delivered presentations, and wrote multiple articles (including for national publications “CPA Journal” and “Estate Planning” magazine). He was also the director of NM’s trust services department for 3 years. In addition to his law degree, Dan holds a CLU and CFP designation. He is married and has 2 daughters.

Just as there are many types of advisors (from multiple disciplines) that help business owners with different parts of the business succession process, there are also many ways to engage owners in the conversation. Depending on the owner’s current “pain” and state of mind, they may be more driven by the prospect of reducing taxes, increasing the value of the business, or resolving an internal conflict. Join Shelley for this dynamic conversation about how to take owners as they come, identify their true issues, and then engage for the conversation that will drive the entire planning opportunity for you and your collaborative team.

Learning Objectives:

• Help owners gain more clarity and identify their true problem

• Engage for the part of business succession you want to do and partner in the rest

• Explain “The Missing Math” owners need to hear

With nearly 40 years of experience in financial and legal services, Shelley Lightfoot is a respected leader in advanced planning, exit strategy design, and advisor collaboration. Her work with The Southern California Institute, Strazzeri Mancini LLP, and The Founders Group has helped countless professionals deliver more comprehensive solutions to successful families and business owners. Read Shelley's full bio here.