In this episode, I sit down with Jeff Condren, Certified Financial Planner and Senior Vice President at Mesirow Wealth Management, a Barron's Top 100 RIA firm with over $11 billion in assets under management.
Jeff was named a Forbes 2024 Best in State Top Next Gen Wealth Advisor and has spent two decades guiding business owners and families through the most complex and consequential financial decisions of their lives.
If you have ever wondered what to do with your money before, during, and after you sell your business, this episode was made for you.
We cover:
– The single biggest financial mistake business owners make: treating the exit as a transaction instead of a multi-year planning event, and why the best exits need at least 24 to 36 months of preparation, ideally 4 to 5 years.
– What Jeff's pre-sale checklist actually looks like: S-Corp vs. C-Corp structure, small business stock eligibility, trust strategies, pre-sale gifting, estate planning, charitable giving, valuation gap analysis, and whether relocating to a different state before the sale makes financial sense.
– Why separating your identity from the business is the single most important mindset shift a first-generation founder can make, and why it is also the foundation of multi-generational wealth.
– The 1 to 2 percent per year strategy: how to slowly move assets outside the business over a decade or more so your entire net worth is never sitting in one place when something goes wrong.
– The Bucket Strategy for post-exit proceeds: how to divide your liquidity into what you can never risk, what you plan to spend in the near term, and what you want to grow across generations.
– Why lifestyle creep is one of the most dangerous threats to exit wealth, and how trusts create the governance and structure needed to protect the plan from family pressure and reactive decisions.
– How GRATs, charitable trusts, donor-advised funds, and second-to-die life insurance policies can protect and grow family wealth long after the sale closes.
– Jeff's one practical tip for every business owner: pay yourself first by setting up a non-negotiable monthly transfer to an investment account, because consistency in building outside assets will always beat trying to time the market.
Connect with Jeff at mesirow.com or search "Jeff Condren" on LinkedIn.
Ready to grow and plan your exit? Visit www.BizExitGrow.com.