Making Cents of It All
Podcast that makes sense of the things people do to make cents...
Making Cents of It All with Jesse Stakes gives the spotlight to the small businesses that make America run. We look to share the "why" behind why people choose what they do professionally and showcase their expertise in their chosen profession for the benefit of our audience.
We also dive into the services that support those small businesses and provide information on the technology and services that allow them to do what they do each and every day effectively and more efficiently.
Making Cents of It All with Jesse Stakes looks to help businesses succeed financially and give them the spotlight while doing so!
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Making Cents of It All
The Exit - The Ultimate Guide to Exit Planning: Deal Structure, Valuation & Life After the Sale
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Making Cents of It All with Jesse Stakes welcomes Jeffrey Condren, CFP®, Senior Vice President at Mesirow Wealth Advisors, for a powerful, insight‑packed conversation on one of the most misunderstood financial milestones a business owner will ever face: the exit.
Drawing from years of advising founders, entrepreneurs, and multi‑generation business owners, Jeffrey breaks down the real drivers of a successful sale — the operational, financial, emotional, and personal factors that determine whether an exit becomes a wealth‑building event or a missed opportunity.
🔍 What We Cover in This Episode
1. Setting the Stage: When Owners Should Start Thinking About an Exit
Jeffrey explains the earliest signals that it’s time to prepare, the mindset shifts that separate successful sellers from those who struggle, and why the emotional side of letting go often catches founders off guard.
2. Preparing the Business for Sale
We dig into the operational and financial blind spots owners commonly discover, the ideal preparation timeline, and the metrics buyers scrutinize most. Jeffrey also highlights why leadership succession planning is one of the most underrated value drivers.
3. Building the Right Advisory Team
Jeffrey outlines the essential advisors every owner needs, the risks of relying solely on internal teams, and how a strong advisory bench protects value during negotiations.
4. Understanding Valuation & Deal Structure
We unpack the biggest misconceptions around valuation, how to think beyond the headline number, and the long‑term impact of earn‑outs, rollover equity, and seller financing.
5. The Wealth Event: Preparing for Life After the Sale
Jeffrey shares how he helps clients prepare for the sudden shift in wealth, avoid common post‑liquidity mistakes, and build a long‑term plan that integrates tax strategy, investments, and stewardship.
6. Emotional & Personal Transitions
We explore the identity challenges founders face once the business is no longer theirs, how to prepare family members for the impact of a liquidity event, and what a healthy transition truly looks like.
7. Lessons Learned & Real‑World Stories
Jeffrey shares examples of owners who prepared exceptionally well — and those who didn’t — and the lessons every business owner can apply today.
Rapid‑Fire Takeaways
- Biggest value‑killer
- Most underrated value‑driver
- One thing owners should stop doing
- One thing they should start doing
- The question owners never ask but should
This episode is a must‑listen for any founder, entrepreneur, or family‑owned business preparing for the next chapter.
