Webinars from Oak Street Funding

Upcoming Webinars

Doing Deals: M&A Essentials for Buyers and Sellers

In this webinar we will introduce buyers and sellers to essential elements of doing a deal. Specifically we will discuss the types of practice sales and deal structures, the process for buying/selling a practice, key legal, tax, and financing considerations. We will also cover support options that are available for both buyers and sellers. A live Q&A session will follow.

August 14th, 2025

2:30 P.M. EST

Online

Agency Growth Through M&A with Oak Street Funding

Jason Gaskell, VP of Strategic Markets for Oak Street Funding, will share how Oak Street Funding can help insurance agency owners like you secure financing for M&A growth.

August 27th, 2025

1:00 P.M. EST

Online

Webinar Recordings

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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.

Inside Insurance M&A: Exploring the Process

Chris Hughes, Managing Director of Insurance Distribution at M&A Services, joins Jason Gaskell, VP of Strategic Markets at Oak Street Funding, for the first of a three-part webinar series on mergers and acquisitions. In this first webinar, they walk through the various stages of the M&A process, timeline, and what buyers and sellers can anticipate.

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.

Insurance Growth Into 2025: M&A and Deal Structures

Join Jason Gaskell, VP of Strategic Markets at Oak Street Funding, and Chris Hughes, Managing Director of Insurance Distribution at M&A Services, for a webinar on the current M&A market.

Cybersecurity: Conquering Compliance

AERIFY.io joins Oak Street Funding to discuss accounting and investment advisor cybersecurity trends and talk about conquering compliance with the FTC Safeguard guidelines and WISP.

Doing Deals: M&A Essentials for Buyers and Sellers

Join M&A experts from Advisor Legacy and lending partner Oak Street Funding as we introduce prospective buyers and sellers to essential elements of doing a deal. We will also cover deal support options that are available for both buyers and sellers.

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.