What really happens after you sell your business?

In this episode of Business Owner Boot Camp, Sandy Wiggins sits down with Matt Reynolds, Chief Growth Officer of Newport Private Wealth, a Wealthspire company, to talk through what business owners often don’t see coming. Drawing on a survey of former business owners, they share honest insights on how the sale process actually unfolds and what people wish they had done differently.

The conversation goes beyond taxes and deal mechanics to cover the personal side of a liquidity event. That includes how identity shifts after a sale, why relationships can change, and how easy it is to feel pressure to make quick decisions with newfound cash.

If you’re planning to sell your business, or even just starting to think about it, this is a straightforward look at what to expect and how to approach it more thoughtfully.

Newport Private Wealth, Business Seller Survey Report (2008).

Wealthspire Advisors LLC and certain of its affiliates are separately registered investment advisers. This presentation is for general information and educational purposes only. It should not be construed as personalized investment, legal, tax, or accounting advice, or a guarantee that you will experience a certain level of results if Wealthspire is engaged, or continues to be engaged, to provide services. While the information is considered to be reliable, Wealthspire cannot guarantee its accuracy, completeness, or suitability for any purpose, and makes no warranties with regard its use. Different types of investments involve varying degrees of risk, and it should not be assumed that any investment, investment strategy, or non-investment related or planning services will be profitable, be suitable for your portfolio or individual situation, or prove successful. A copy of Wealthspire’s current written disclosure Brochure discussing our services and fees is available upon request or at www.wealthspire.com.

In this episode of Wealthspire’s Business Owner Bootcamp, Michael Delgass is joined by Ben Kronish, of Financial Architects Partners for a practical conversation on buy-sell agreements, why closely held businesses need them, and what can go wrong when there’s no plan (or no funding) in place. They unpack the real-world fallout of “figure it out later,” including disrupted operations, cash-flow strain, and the risk of ending up with unintended partners or disputes.

They also cover the essentials of how buy-sells work: key triggering events (death, disability, retirement, divorce), cross-purchase vs. redemption structures, and how insurance is commonly used to fund the agreement. Tune in to hear more of their conversation.

Wealthspire Advisors LLC and certain of its affiliates are separately registered investment advisers. This presentation is for general information and educational purposes only. It should not be construed as personalized investment, legal, tax, or accounting advice, or a guarantee that you will experience a certain level of results if Wealthspire is engaged, or continues to be engaged, to provide services. While the information is considered to be reliable, Wealthspire cannot guarantee its accuracy, completeness, or suitability for any purpose, and makes no warranties with regard its use. Different types of investments involve varying degrees of risk, and it should not be assumed that any investment, investment strategy, or non-investment related or planning services will be profitable, be suitable for your portfolio or individual situation, or prove successful. A copy of Wealthspire’s current written disclosure Brochure discussing our services and fees is available upon request or at www.wealthspire.com.

In this episode of Business Owner Boot Camp, host Sandy Wiggins sits down with Chris Maxey, Chief Market Strategist at Wealthspire, for a focused conversation on how business owners should approach investment strategy and tax planning before, during, and after a liquidity event.

Tune in as they break down why personal financial planning can’t wait until after the deal closes, how direct indexing and tax‑loss harvesting can help offset capital gains, and how evolving tools like long–short direct indexing create even greater tax efficiency.

A must‑listen for business owners preparing for a sale or transition who want to optimize their investment approach, minimize taxes, and preserve long‑term family wealth.

Wealthspire Advisors LLC and certain of its affiliates are separately registered investment advisers. This presentation is for general information and educational purposes only. It should not be construed as personalized investment, legal, tax, or accounting advice, or a guarantee that you will experience a certain level of results if Wealthspire is engaged, or continues to be engaged, to provide services. While the information is considered to be reliable, Wealthspire cannot guarantee its accuracy, completeness, or suitability for any purpose, and makes no warranties with regard its use. Different types of investments involve varying degrees of risk, and it should not be assumed that any investment, investment strategy, or non-investment related or planning services will be profitable, be suitable for your portfolio or individual situation, or prove successful. A copy of Wealthspire’s current written disclosure Brochure discussing our services and fees is available upon request or at www.wealthspire.com.