Business Owner Bootcamp

Wealthspire Advisors
  • 5.0 (1)
  • Entrepreneurship

Welcome to Business Owner Bootcamp, the Wealthspire podcast designed to help business owners and entrepreneurs take control of their finances. Hosts and financial advisors Michael Delgass and Sandy Wiggins break down key topics like tax strategies, exit planning, business valuations, and real-world experiences with expert guests. 

  1. Jun 1

    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.

    35 min

  2. Mar 17

    Business Owner Bootcamp Episode 12: Buy-Sell Agreements - The Plan Your Business Can’t Skip

    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.

    49 min

  3. Mar 4

    Business Owner Bootcamp Episode 11: Investment Planning Before a Liquidity Event - A Conversation with Chris Maxey

    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.

    37 min

  4. 12/08/2025

    Business Owner Bootcamp Episode 10: Building Your Business' Bench Strength - Strategies for Attracting and Retaining Top Talent

    Join Business Owner Bootcamp co-host Sandy Wiggins and guest Kurt Snyder,  SVP of Business Development for Executive Benefits, for a dynamic conversation blending the grit of ultra marathon running with the art of building resilient businesses. Discover how non-qualified plans, personalized executive benefits, and strategic risk management can help business owners attract, retain, and reward top talent, all while preparing for successful transitions and maximizing enterprise value.  Whether you’re a business owner, executive, or advisor, this episode offers actionable insights for navigating today’s evolving workforce. 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.

    34 min

  5. 11/17/2025

    Business Owner Bootcamp Episode 9: Beyond the Sale - Redefining Identity and Purpose for Business Owners

    In this episode of the Business Owner Bootcamp Podcast, host Michael Delgass sits down with transition expert Elizabeth Parsons from Zelinka Parsons, a consulting firm that guides business owners and attorneys through retirement, succession, and professional transition with clarity. Tune in as we explore the psychological and emotional challenges business owners face when selling their companies. Discover why identity and life structure are so deeply tied to entrepreneurship, and learn actionable strategies for designing a fulfilling post-sale life. Whether you’re planning a sale or supporting someone who is, this conversation offers a roadmap for personal reinvention and lasting fulfillment. 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.

    39 min

  6. 09/28/2025

    Business Owner Bootcamp Episode 8: Beyond the Numbers - Emotional and Strategic Exit Planning for Business Owners

    In this special episode, Mike Delgass sits down with Ramsey Goodrich, Managing Partner and investment banker at Carter Moore & Goodrich to explore the emotional and strategic journey of selling a closely held business. Ramsey brings more than 25 years of experience advising owners and executives of family held and founder led middle market companies on strategies to maximize shareholder value through M&A and capital transactions. 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.

    39 min

  7. 09/10/2025

    Business Owner Bootcamp Episode 7: Employee Stock Ownership Plans Unpacked - Smart Strategies for Business Owners

    In this episode, Sandy Wiggins, financial advisor and Managing Director at Wealthspire Advisors is joined by John Nelson, Managing Director at NFP Retirement, to discuss the ins and outs of ESOPs (Employee Stock Ownership Plans). They explore how ESOPs can be a powerful tool for succession planning, tax efficiency, and employee engagement, and highlight the benefits and considerations of implementing an ESOP. 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.

    40 min

  8. 09/03/2025

    Business Owner Bootcamp Episode 6: Planning Before the Sale of Your Business - Timing, Tools, and Tax Strategies

    In this special episode, Mike Delgass and Sandy Wiggins, financial advisors at Wealthspire Advisors, are joined by their colleague Liz Summers. Liz serves as Director of Wealth Strategy for Wealthspire's Family Wealth practice and joins the podcast to discuss the critical planning steps business owners should consider before selling their company. This episodes covers timing considerations, valuation strategies, the role of family offices post-sale, and wealth transfer techniques, including gifting, irrevocable trusts, and charitable contributions. Tune in to hear more about the importance of starting early, coordinating with advisors, and aligning planning with personal goals and values. 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.

    34 min
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About

Welcome to Business Owner Bootcamp, the Wealthspire podcast designed to help business owners and entrepreneurs take control of their finances. Hosts and financial advisors Michael Delgass and Sandy Wiggins break down key topics like tax strategies, exit planning, business valuations, and real-world experiences with expert guests. 

Information

  • Creator
    Wealthspire Advisors
  • Years Active
    2025 - 2026
  • Episodes
    13
  • Rating
    Clean
  • Copyright
    © 2026 Business Owner Bootcamp
  • Show Website
    Business Owner Bootcamp