After 45 years of running his Massachusetts collision shop, Tom Ricci knew it was time to start planning the next chapter, but like many long-time owners, he wasn’t sure how to step back without losing himself or the business.

In this episode, Matt DiFrancesco talks with Tom about the real-life journey of transitioning out of a decades-old shop, the surprising discovery that he was still needed in the business 42% of the time, and how that realization shaped his exit strategy. Tom shares how he found Matt, why he chose to sell rather than become a “missing in action” owner, and how assembling the right team gave him structure and direction throughout the process.

Tom also reflects on life after the sale, the importance of building a post-business identity, and why owners should never wait until burnout to start planning. His story is a practical, candid roadmap for any shop owner thinking about their future, their lifestyle, and their legacy.

Matt and Tom also talk about:

(06:38) Why identifying the real results of exit planning changes your transition

(07:43) How evaluating lifestyle needs and business value shapes your long-term vision

(10:37) Why most owners regret selling, and how defining post-shop identity prevents it

(13:49) How planning before burnout protects your leverage and your future options

(16:17) Why exit planning is an ongoing journey and why having a Plan B matters

If Tom’s story resonates with listeners and they’d like to discuss their own situation, they can schedule a call with Matt at https://highliftfinancial.com/. He offers a complimentary 30-minute conversation to understand where they are, where they want to go, and whether working together might be a good fit. And even if it isn’t, Matt always ensures they’re pointed in the right direction for their next steps.

Connect With Matt DiFrancesco:

[email protected]

(814)201-5855

LinkedIn: Matt DiFrancesco

LinkedIn: High Lift Financial

Facebook: High Lift Financial

Instagram: @high_lift_financial

YouTube: @highliftfinancial

About the guest:

Tom Ricci is a former collision shop owner from Massachusetts who successfully ran his family-owned business for 45 years before transitioning into retirement. With decades of hands-on leadership and industry experience, Tom brings a candid, real-world perspective on what it truly takes to step back from a long-standing business. After selling his shop to a third party, he now explores opportunities to stay connected to the industry, potentially through consulting, while redefining his next chapter beyond ownership.

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.