The Long Game

Year-End Tax Checklist Every Business Owner Needs (2026)

The Most Misunderstood Tool in Executive Comp: Deferred Compensation (with Eric Courage, CFA, CFP, CAIA)

Building Wealth for Your Kids: 529 Plan, Custodial Roth, UTMA, Trump Accounts

How to Give to Charity the Right Way (and Save a Ton in Taxes)

Stop Doing Roth Conversions at the Wrong Time (w/ Ben Lake)

How Much is Enough? (w/ Dr. Julie Gurner)

Leaving Corporate Life? Here's What Nobody Tells You About Money

Transitioning from a corporate W-2 role to independent consulting requires a strategic approach to entity structure and tax management to maximize financial freedom. Establishing a separate business entity, such as an LLC or S-Corp, provides the foundation for tax-efficient operations. High-earning consultants should l...

Financial Regrets of High Net Worth People (w/ Benjamin Lake, CFA®, CFP®)

Home Buying as a Business Owner (w/ Padi Goodspeed)

Health Insurance Options for Small Business Owners (w/ Nick Lease)

How to Have a Successful Early Retirement (w/ Court Carruthers)

How to Maximize Leverage as a Business Owner (w/ Jon Matzner)

Most Controversial Financial Topics (+ Our Thoughts On Each)

Section 1244: Writing Off Losses from Small Business Stock (w/ Bryan Hasling, CFP®)

How Estate Planning Has Changed in 2026 (w/ David Haughton, JD, CPWA®)

The IPO Episode: Here's What Employees Need to Know (w/ Bryan Hasling)

Everything You Need to Know About Revocable Trusts (w/ David Haughton, JD, CPWA®)

Business Partners, Buyouts, & Hard Conversations (with Cody Wittick)

How Smart Founders Structure Their Businesses (w/ Ryan Dolan)

"Should I Turn My Primary Residence into a Rental?"