loader from loading.io

What’s New in Tax Planning?

Dollars to Dreams: Planning with Purpose | Penobscot Financial Advisors

Release Date: 06/11/2025

PFA Celebrates the Holidays! (Tyler Hafford and Reilly Dwight) show art PFA Celebrates the Holidays! (Tyler Hafford and Reilly Dwight)

Dollars to Dreams: Planning with Purpose | Penobscot Financial Advisors

Happy New Year from Penobscot Financial Advisors! Hannah Tackett welcomes Tyler Hafford, and Reilly Dwight to share holiday memories, favorite foods, plus a special look back at 2025 and a look forward to 2026!

info_outline PFA Celebrates the Holidays! (Sam Chaplin and Tucker Grinnell) show art PFA Celebrates the Holidays! (Sam Chaplin and Tucker Grinnell)

Dollars to Dreams: Planning with Purpose | Penobscot Financial Advisors

Happy Holidays from Penobscot Financial Advisors! Hannah Tackett welcomes Sam Chaplin, and Tucker Grinnell to share holiday memories, favorite foods, plus a special look back at 2025 and a look forward to 2026!

info_outline PFA Celebrates the Holidays! (Yelsh Gebreselassie) show art PFA Celebrates the Holidays! (Yelsh Gebreselassie)

Dollars to Dreams: Planning with Purpose | Penobscot Financial Advisors

Happy Holidays from Penobscot Financial Advisors! Hannah Tackett welcomes Yelsh Gebreselassie to share holiday memories, favorite foods, plus a special look back at 2025 and a look forward to 2026!

info_outline PFA Celebrates the Holidays! (Libby McKay and Rebecca Schuman) show art PFA Celebrates the Holidays! (Libby McKay and Rebecca Schuman)

Dollars to Dreams: Planning with Purpose | Penobscot Financial Advisors

Happy Holidays from Penobscot Financial Advisors! Hannah Tackett welcomes Libby McKay, and Rebecca Schuman to share holiday memories, favorite foods, plus a special look back at 2025 and a look forward to 2026!  

info_outline PFA Celebrates the Holidays! (Julie Willette and Jim Bradley) show art PFA Celebrates the Holidays! (Julie Willette and Jim Bradley)

Dollars to Dreams: Planning with Purpose | Penobscot Financial Advisors

Happy Holidays from Penobscot Financial Advisors! Hannah Tackett welcomes Julie Willette, and Jim Bradley to share holiday memories, favorite foods, plus a special look back at 2025 and a look forward to 2026!

info_outline PFA Celebrates the Holidays! (Craig Joncas and Jessie Dolmage) show art PFA Celebrates the Holidays! (Craig Joncas and Jessie Dolmage)

Dollars to Dreams: Planning with Purpose | Penobscot Financial Advisors

Happy Holidays from Penobscot Financial Advisors! Hannah Tackett welcomes Craig Joncas, and Jessie Dolmage to share holiday memories, favorite foods, plus a special look back at 2025 and a look forward to 2026!

info_outline Sam's Insights Into Digital Assets show art Sam's Insights Into Digital Assets

Dollars to Dreams: Planning with Purpose | Penobscot Financial Advisors

These days, a coin can hold as much value as code, and a dollar can be digital by design. It's a burgeoning financial world out there, and there aren't many maps for this marketplace. Tyler Hafford and PFA’s Chief Investment Officer, Sam Chaplin, sit down and discuss Digital Assets, the intriguing pros, the concerning cons, and the curious comparisons to the regular economy. Despite many long years, money now always acts like money then: what might make the change is the people who are holding it. YOU’LL LEARN: How digital assets differ from physical analogues How assets like...

info_outline When Trust Turns To Terror: Extortion From Afar show art When Trust Turns To Terror: Extortion From Afar

Dollars to Dreams: Planning with Purpose | Penobscot Financial Advisors

In this episode of Dollars to Dreams, host Tyler Hafford is joined by Penobscot Financial Advisors’ Chief Operations and Compliance Officer, Hannah Tackett, for another installment in a new series on cyber scams. Today, they talk about "Ted," a victim who was tricked by a scammer into a devastating blackmail scheme, and what happened when the money ran out. Tyler and Hannah break down his story and the tactics scammers use to prey on connection, trust, and online connections, and they offer invaluable tips on how you can protect yourself from falling victim to these increasingly...

info_outline AI V.S. DOT COM show art AI V.S. DOT COM

Dollars to Dreams: Planning with Purpose | Penobscot Financial Advisors

Programming note: This episode is a quick interruption to our 5-part Cyber Scam Mini-Series—we’ll jump right back into it next week. Is today’s AI boom just dot-com all over again—or something entirely different? Tyler Hafford and PFA’s Chief Investment Officer, Sam Chaplin, dig into what’s hype, what’s real, and what long-term investors should watch: Piece by piece, they compare the details of the rise of artificial intelligence agents to the investment bubble of the 1990s known as the Dot Com Boom. Tyler and Sam go over the similarities and many differences between the two...

info_outline Carol’s Customer Service Scam show art Carol’s Customer Service Scam

Dollars to Dreams: Planning with Purpose | Penobscot Financial Advisors

In this episode of Dollars to Dreams, host Tyler Hafford is joined by Penobscot Financial Advisors’ Chief Operations and Compliance Officer, Hannah Tackett, for another installment in a new series on cyber scams. They dive into the alarming aspects of two successive scams, and share the story of “Carol”, a victim who lost more than she bargained for with a customer service scam. Tyler and Hannah break down the tactics scammers use to prey on reputations and receipts, and they offer invaluable tips on how you can protect yourself from falling victim to these increasingly sophisticated...

info_outline
 
More Episodes

Tyler Hafford and Hannah Tackett break down key updates every investor should know—from Secure Act 2.0’s game-changing provisions like Roth 401(k) matches and 529-to-Roth transfers, to the fast-approaching 2025 expiration of current tax laws. With timely insights and practical examples, they show how to leverage today’s rules to minimize future taxes and why proactive planning now could pay off big later.

You’ll learn:  

  1. Secure Act 2.0 Updates – What’s changed with RMDs, Roth employer contributions, and 529 plans.

  2. 529 Plans Reimagined – Why these accounts are now more flexible and powerful than ever for family financial planning.

  3. 2025 Tax Law Expiration – What may change, what to watch for, and how to plan proactively before tax rates increase.

Takeaways:  

  • [03:05] – “The RMD age has increased again—now 73, and heading to 75 by 2033.” – A longer runway for tax planning.

  • [06:12] – 529 to Roth IRA rollovers explained – After 15 years, unused 529 funds can support retirement savings for your child.

  • [09:50] – “That bank account’s not keeping up with inflation—especially college inflation.” – Hannah unpacks missed opportunities in common college savings approaches.

  • [17:35] – 2025 Tax Sunset overview – Brackets may rise, deductions may shrink, and estate tax exemptions could be halved if Congress doesn’t act.

  • [20:48] – “2024 and 2025 are your years for Roth conversions and gifting strategies.” – Use the current low-tax environment to your advantage.

Got questions? We can answer them with clear, actionable strategies. Contact us at PenobscotFA.com