Guest: Brandon Smith, Independent Financial Planner, Milestone Financial Solutions
Host: Alex Mejias, Founder & Managing Attorney, James River Law

If you’re a closely held or family business (1–4 owners, ~10–15 employees), this episode is your practical guide to business continuation and succession planning. Alex and Brandon break down buy-sell agreements, valuation methods (handshake, informal, and formal valuations), funding options (loans, sinking funds, term & permanent life insurance), and when to use cross-purchase vs. entity/stock-redemption structures. They also dig into key person insurance, disability coverage, tax considerations for S-corps vs. C-corps, and what actually happens when planning is ignored—or done well.

What you’ll learn

• The two must-haves in any buy-sell: valuation method & funding method
• Cross-purchase vs. entity redemption: when each structure fits
• Why term life is often the most affordable funding—and when permanent/VUL can make sense
• How key person and disability insurance keep the lights on
• S-Corp dividend vs. payroll treatment, and why you don’t deduct life insurance premiums
• Sector tips: restaurants, trades (plumbing/HVAC), professional services, creatives & athletes
• Real stories of success and failure that show the stakes

Resources & links

• Milestone Financial Solutions: milestonefinancialsolutions.com
• James River Law (buy-sell agreements & estate planning): jamesriverlaw.com

Want help drafting or updating a buy-sell? Book a consult at jamesriverlaw.com.

Need funding/coverage options? Talk with Brandon at milestonefinancialsolutions.com.

Disclaimer
This episode is for informational purposes only and is not legal, tax, or financial advice. Consult your attorney, CPA, and licensed advisor for guidance specific to you.

Connect with Us:

• Website: jamesriverlaw.com
• Instagram: @jamesriverlaw
• LinkedIn: JamesRiverLaw
• Contact: hello@jamesriverlaw.com
• Book a Call: jamesriverlaw.com/book-a-call

👉 Like, subscribe, and share to stay tuned as we explore the full journey of entrepreneurship — from start to legacy.

What happens to your business when you step away — or can’t return? In this episode of The Mark You Leave, the legal team at James River Law explains everything entrepreneurs and small business owners need to know about succession planning and preserving their business legacy.

🎯 Learn the fundamentals of:

· What succession planning is and why it matters

· Buy-sell agreements (cross-purchase vs. redemption)

· Valuation methods for business exit

· How succession planning fits into your estate plan

· Real-world consequences of poor planning

Whether you're in a single-member LLC or a multi-partner corporation, this episode breaks down the tools, strategies, and common pitfalls business owners face when planning for the future.

📞 Need help with your succession plan? Schedule a consult at www.jamesriverlaw.com
💌 Submit questions: podcast@jamesriverlaw.com

#successionplanning #smallbusinesslaw #businesslegacy #buyandsellagreement #estateplanning #virginialaw #businessowners #entrepreneurlawyer

Connect with Us:

• Website: jamesriverlaw.com
• Instagram: @jamesriverlaw
• LinkedIn: JamesRiverLaw
• Contact: hello@jamesriverlaw.com
• Book a Call: jamesriverlaw.com/book-a-call

👉 Like, subscribe, and share to stay tuned as we explore the full journey of entrepreneurship — from start to legacy.

Episode Summary:
In this episode of The Mark You Leave, Alex Mejias of James River Law, along with co-hosts Tariq and Bri, breaks down the big decision every business owner must make -- how to choose the right legal entity structure.

From the simplicity (and risk!) of sole proprietorships to the flexibility of LLCs, the team uses real-life examples (yes, Beyoncé and Destiny’s Child included) to walk through partnerships, C corps, S corps, and PLLCs. Plus, they discuss how to actually protect yourself from liability — because filing the paperwork is just the beginning.

Whether you’re launching your side hustle or scaling your startup, this episode is a must-listen.

What You’ll Learn in This Episode:

• The real risks of sole proprietorships and partnerships
• Why LLCs are a flexible, popular choice for entrepreneurs
• How corporations are structured and taxed (C Corps vs. S Corps)
• When and why a PLLC is required
• The truth about “piercing the corporate veil” — and how to avoid it
• How creatives and public figures can protect their identity using an EIN
• Why business formation is more than just paperwork

Connect with Us:

• Website: jamesriverlaw.com
• Instagram: @jamesriverlaw
• LinkedIn: JamesRiverLaw
• Contact: hello@jamesriverlaw.com
• Book a Call: jamesriverlaw.com/book-a-call

👉 Like, subscribe, and share to stay tuned as we explore the full journey of entrepreneurship — from start to legacy.