Webinars from Oak Street Funding

Upcoming Webinars

Cybersecurity Trends and Risks in 2025 with KSM and Reveal Risk

Join Ben Phillips, director and IT risk advisor at KSM, and Cody Rivers, managing director at Reveal Risk, as they join David Christman, Chief Information Officer at Oak Street Funding, to discuss the current state of cybersecurity, key trends to watch out for, the FTC Safeguards Rule, and the risks businesses face without strong protections in place. They’ll also share practical steps companies can take to strengthen their defenses and prepare for what’s ahead.

October 3rd, 2025

12:00 P.M. EST

Online

Webinar Recordings

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Inside Insurance M&A: Valuation & Deal Structure

Join host, Matt Staninger, Market Research Analyst at Oak Street Funding, and Chris Hughes, Managing Director at M&A Services, as they discuss valuation methodology, maximizing value in deal structures, leverage, and tax considerations. They also cover their insights on the current market environment and give an overview over Pro Forma Income Statements.

Doing Deals: M&A Essentials for Buyers and Sellers

In this webinar we introduce buyers and sellers to essential elements of doing a deal. Specifically, they discussed: the types of practice sales and deal structures, the process for buying/selling a practice, key legal, tax, and financing considerations. They also covered support options that are available for both buyers and sellers.

Leaving Your Legacy: Building an Exit Strategy

Dennis Leininger, Founder and Principal Consultant at Business Transition Solutions, joins Keara Bradley, VP of Strategic Markets at Oak Street Funding, to discuss the succession process, tips on overcoming obstacles, what to look for in a successor, and more.

Responding to Uncertainty: Mid-Year Outlook

Rick Dennen, Founder and CEO of Oak Street Funding, and Alicia Chandler, President of Oak Street Funding, join Matt Staninger, Market Research Analyst at Oak Street Funding, for a mid-year review and outlook for the remainder of 2025. Our experts will cover their market outlooks, strategic acquisitions, and lending trends to equip you to thrive in today’s dynamic landscape.

2025 Outlook: What to Expect in the Year Ahead

Join Rick Dennen, Founder and CEO of Oak Street Funding, as he provides insights into the year ahead. Rick answers your questions regarding potential disruptive forces, utilizing technology and AI, and more.

Election Special: Tax & Market Update

Steve Blake, Managing Director at CBIZ, and Marc Chandler, Chief Market Strategist at Bannockburn Global Forex, are back for a discussion led by Oak Street Funding Market Research Analyst, Matt Staninger.

Making a Succession Plan: Our Story

In 2021, Rick assumed the position of Chief Corporate Banking Officer at First Financial Bank, which created an opportunity for someone to fill the role of president at Oak Street Funding. Alicia Chandler was promoted from Chief Legal Counsel to President of Oak Street Funding in July of 2022. In this webinar, Rick and Alicia will share succession and transition insights from their own experiences with helpful tips for our audience.

Beyond Underwriting: Strategy and Insights

Join Oak Street Funding's Director of Underwriting, Rob Roach, and VP of Sales, Adam Farag, as they delve into the world of underwriting and provide valuable insights on market trends and their impact on company strategy and underwriting decisions.

Uncover M&A Possibilities: Bridge Loans and Deal Creativity

Join Adam Farag, VP of Sales at Oak Street Funding, and Rob Madore, VP of Financial Advisory at MarshBerry, as they discuss the current market environment and its impact on sellers and buyers, bridge loans, dividend recapitalizations, and deal makeup.

Business Agility: Thriving in Changing Markets

In this webinar, Rick Dennen, Founder and CEO of Oak Street Funding, and Paul Lally, Principal at Wipfli, discuss how you can navigate changing markets to grow and strategize by leveraging technology to improve your talent management, employee retention and recruitment, and operating agility.

How to Grow Your Financial Advisory Firm in Turbulent Times

Watch Alicia Chandler, President of Oak Street Funding, and Taylor Adkins, Chief Product & Marketing Officer at UPTIQ, as they discuss growth during difficult seasons and maintaining that growth mindset throughout the years.

Building Your Wealth Advisory Firm's Acquisition Strategy

Join Oak Street Funding's Adam Farag, VP Strategic Markets Sales, and MarshBerry's Vice President, Rob Madore, as they discuss evolving market conditions, creating a robust acquisition strategy that includes your financial preparedness, and considerations for completing the transaction.

Panel Discussion with Bristal Lane

Susie McEuen, Consultant with Oak Street Funding, brought Bristal Lane, a business consulting firm, to speak on a panel. The panelists discuss current trends, growth strategies, and how to stay compliant focusing on what advisors can do to maintain growth.