Wealthspire - Business Owner Bootcamp

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

Sandy Wiggins, CFP®, AIF® — Mon, 01 Jun 2026 09:00:00 GMT

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.

Buy-Sell Agreements - The Plan Your Business Can’t Skip

Mike Delgass — Wed, 18 Mar 2026 09:00:00 GMT

In this episode of 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.

Investment Planning Before a Liquidity Event - A Conversation with Chris Maxey

Sandy Wiggins, CFP®, AIF® — Wed, 04 Mar 2026 10:00:00 GMT

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.

Building Your Business' Bench Strength - Strategies for Attracting and Retaining Top Talent

Sandy Wiggins, CFP®, AIF® — Fri, 05 Dec 2025 10:00:00 GMT

Welcome to Business Owner Bootcamp, the Wealthspire Advisors 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.

Join Business Owner Bootcamp co-host Sandy Wiggins and guest Kurt Snyder 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.

Beyond the Sale - Redefining Identity and Purpose for Business Owners

Mike Delgass — Fri, 14 Nov 2025 10:00:00 GMT

In this episode, 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.

Beyond the Numbers - Emotional and Strategic Exit Planning for Business Owners

Mike Delgass — Fri, 26 Sep 2025 09:00:00 GMT

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.

Together, Mike and Ramsey discuss practical insights on preparing for a sale, building the right advisory team, understanding valuation, mitigating risk, and defining success beyond just the dollar amount. Tune in to hear more from Mike and Ramsey.

Employee Stock Ownership Plans Unpacked - Smart Strategies for Business Owners

Sandy Wiggins, CFP®, AIF® — Mon, 08 Sep 2025 09:00:00 GMT

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.

Planning Before the Sale of Your Business - Timing, Tools, and Tax Strategies

Mike Delgass — Tue, 02 Sep 2025 09:00:00 GMT

In this special episode, Mike Delgass and Sandy Wiggins are joined by Liz Summers, Director of Wealth Strategy for Wealthspire's Family Wealth practice, as they discuss the critical planning steps business owners should consider before selling their company. This episode covers timing considerations, valuation strategies, the role of family offices post-sale, and wealth transfer techniques, including gifting, irrevocable trusts, and charitable contributions.

Key Strategies to Think About When Selling Your Business

Sandy Wiggins, CFP®, AIF® — Mon, 18 Aug 2025 09:00:00 GMT

In this episode, Sandy Wiggins, financial advisor and Managing Director at Wealthspire Advisors, is joined by Conrad Garcia, Partner and Tax Attorney at Williams Mullen, to explore critical tax planning strategies for business owners preparing for a sale, along with the importance of assembling a transaction team, entity structure considerations, personal goodwill, QSBS opportunities, and estate planning techniques. Whether you're selling a C Corp, S Corp, or LLC, this episode offers valuable guidance to help you plan ahead and avoid costly mistakes.

Advanced Tax Strategies for Business Owners - Unlocking QSBS

Mike Delgass — Fri, 25 Jul 2025 09:00:00 GMT

In this episode, co-host Michael Delgass and Advisor Kevin Brady, Senior Vice President at Wealthspire Advisors, dive into the powerful tax planning tool known as Qualified Small Business Stock (QSBS). They explore recent legislative updates, including increased exclusions and shortened holding periods, and unpack strategies like stacking and trust structuring to maximize tax benefits. Whether you're a founder, investor, or advisor, this conversation offers valuable insights into how QSBS can help business owners reduce capital gains taxes and enhance estate planning.