The Biggest Expense You’ll Have in Retirement Isn’t What You Think

The Classes Your Kid Picks This Spring Will Follow Them to Every College Application

The classes your kid picks this spring — right now — will shape which colleges say yes senior year. College counselor Rhett Rybarczyk returns to reveal what actually moves the needle on a transcript, why “just take all the APs” can backfire, and the one document (the school profile) that quietly frames how colleges read your child’s entire record.

The Number One, Single Most Important Thing to Know as a Parent

Teaser Episode: To lead us into Friday's episode, Matt talks about one of the most important skills every parent needs: communicating effectively with your children. Returning guest, Rhett Rybarczyk, continues the conversation later this week with a focus on the high-stakes years leading up to college.

Raise Financially Confident Kids, without Raising Entitled Ones

In a world of instant gratification, how do you raise children who are both financially confident and genuinely responsible? In this episode, Matt is joined by guest Lynette Khalfani-Cox to explore the delicate balance between empowering your kids with financial literacy while avoiding an entitlement mindset that can derail their future.

Tips and Tricks to Help Your Child Learn About Money

Teaser Episode: Your kids won't inherit your spreadsheets; they'll inherit your habits. Matt leads us into Friday's episode, with guest Lynette Khalfani-Cox, discussing key steps in modeling your financial values to your children.

The AMT Trap: How One Stock Option Exercise Can Blow Up Your Tax Return

You exercise your incentive stock options. You don't sell a single share. No cash ever hits your account — and then your accountant calls with a six-figure tax bill on a "gain" that exists entirely on paper. That's the Alternative Minimum Tax, and for anyone holding ISOs it's the most expensive surprise in equity compensation. In this episode, Matthew Daugherty sits down with AJ Ayers — partner at Brooklyn FI and one of the sharpest minds working in incentive stock options — to break down how AMT gets triggered, why the spread between your strike price and fair market value becomes a tax bomb, and the planning moves most people miss: early exercise, the AMT "gap," QSBS, and the credit you may be able to claw back later. The difference between a tax-free windfall and years of installment payments usually comes down to decisions made before you exercise — not after. If you hold ISOs, or you're leaving a public company for a startup convinced it's your big payday, hear this first. Creative Money by AJ Ayers: 9798217180462 | PenguinRandomHouse.com: Books [https://www.penguinrandomhouse.com/books/808718/creative-money-by-aj-ayers/]