skip to main content
Form CRS Disclosures Client Login
Business Owner Bootcamp
podcast

The Hidden Side of Selling a Business - Identity, Regret, and What Comes Next

June 01, 2026

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.

Podcast Episode Image
Season 1 / Episode 13 / June 01, 2026

Business Owner Bootcamp Episode 13: The Hidden Side of Selling a Business: Identity, Regret, and What Comes Next

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.


Wealthspire Advisors
00:00
00:00

IMPORTANT DISCLOSURE INFORMATION

Wealthspire Advisors LLC, Fiducient Advisors LLC, Wealthspire Retirement, LLC dba Wealthspire Retirement Advisory, and certain other 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.


Related Content

https://www.wealthspire.com/business-owner-bootcamp/episode-13-the-hidden-side-of-selling-a-business-identity-regret-and-what-comes-next/
2026 Copyright | All Right Reserved