123. Building Value Before the Exit: The Human Side of Transition Planning with Hannah Chalker

Exit planning is often talked about in terms of numbers, valuation, and deal structure, but what happens when the real work starts with people, emotions, and a clear sense of what comes next?

In this episode, Matt Di Francesco sits down with Hannah Chalker, a Certified Exit Planning Advisor and Certified Growth Value Advisor, to explore what truly drives successful business transitions. Hannah shares how her journey into the Exit Planning space began, why the discovery process is the foundation of every strong plan, and how she learned to see transition planning as both a strategic and deeply human process.

Matt and Hannah also talk about:

(04:13) Why increasing business value is a long-term process, not a short-term decision

(05:06) How documenting SOPs ahead of time protects value in any transition

(06:43) Why exit planning becomes emotional and requires a true leap of faith

(09:43) How acting as a trusted partner helps owners gain confidence in their transition

(11:00) Why helping owners grow value over time is the most rewarding part of the work

Connect With Hannah Chalker

LinkedIn; https://www.linkedin.com/in/hannah-chalker/

Connect With Matt DiFrancesco:

matt@highliftfin.com

(814)201-5855

LinkedIn: Matt DiFrancesco

LinkedIn: High Lift Financial

Facebook: High Lift Financial 

Instagram: @high_lift_financial

YouTube: @highliftfinancial

About the guest:

Hannah Chalker helps business owners build stronger, more valuable companies through strategic financial and exit planning. As Director of Business Development and an Exit Planning Advisor at HighLift Financial, she works alongside Matt DiFrancesco to guide owners through value growth, transition planning, and long-term decision making. A Certified Exit Planning Advisor (CEPA) and Certified Value Growth Advisor (CVGA), Hannah brings clarity, structure, and a steady hand to every stage of the journey, helping owners protect their legacy and confidently plan what comes next.

Disclaimer:

All information is obtained from sources deemed reliable, but not guaranteed. No tax or legal advice is given nor intended. Content provided herein or on our website should not be construed as an offer for investment advice or for securities, insurance, or other investment products. Investments involve the risk of loss and are not guaranteed. Consult a qualified legal, tax, accounting, or financial professional before implementing any investments or strategy discussed here.

High Lift Financial is a DBA for DiFrancesco Financial Concierge, LLC.  Investment advisory services are provided through Cornerstone Planning Group, LLC, an independent advisory firm registered with the Securities and Exchange Commission.