Dollars to Dreams: Planning with Purpose | Penobscot Financial Advisors
A financial planning podcast that makes complex money topics accessible through real conversations. Hosted by Tyler Hafford and his team at Penobscot Financial Advisors, it focuses on how thoughtful planning can help listeners take control of their finances. The show aims to support both current living and future goals. Disclaimers and privacy information are available on the Penobscot Financial Advisors website.
Episodes
The Artificial Advisor
Whether you like it or not, AI is coming, and it is coming in fast. We are approaching a major paradigm shift in the world of investing, but what will it look like? On this episode of Dollars To Dreams: Planning with Purpose, Tyler Hafford spells it out plain and simple: AI will be a revolutionary tool to aid the process, but it cannot do the most important part... the artificial advisor can help,
Simple Investing Works
Simple investing works, but it's no simple task. Precise and conscientious moves are what get you through the winding waves of the investment world today, and it's on Tyler Hafford's agenda to show you the moves on this episode of Dollars to Dreams: Planning with Purpose. Simple moves make up all clever plans, and with intentionality behind each action, you'll find that navigating the financial la
The Iranian Conflict
You can only go so far when managing yourself in unprecedented times, but managing your financial future requires keeping both an eye on the news and your mind free from panic. In this episode of Dollars to Dreams, Tyler Hafford and PFA's Chief Investment Officer, Sam Chaplin, discuss the ramifications of the U.S. and Israeli conflict with Iran, and what this means for stocks, for oil, and for eve
Are we going to be o-K?
Nowadays, the economy is either looking extra bright or very grey, and it can feel like a coin flip as to who is seeing which side. Why does it feel like there are two separate lines on this graph? The reality is, there is: and some of us are rising upwards while some of us are sliding down. How did this happen, what will this do to the market, and how can we navigate it now? On this episode of Do
PFA Celebrates the Holidays! (Tyler Hafford and Reilly Dwight)
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!
PFA Celebrates the Holidays! (Sam Chaplin and Tucker Grinnell)
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!
PFA Celebrates the Holidays! (Yelsh Gebreselassie)
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!
PFA Celebrates the Holidays! (Libby McKay and Rebecca Schuman)
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!
PFA Celebrates the Holidays! (Julie Willette and Jim Bradley)
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!
PFA Celebrates the Holidays! (Craig Joncas and Jessie Dolmage)
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!
Sam's Insights Into Digital Assets
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 year
When Trust Turns To Terror: Extortion From Afar
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 an
AI V.S. DOT COM
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 th
Carol's Customer Service Scam
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 b
When Love Becomes Leverage: Stacy's Romance Scam
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 "Stacy", a victim who lost about half of all of her wealth to online romance scams. Tyler and Hannah br
The 2 Million Dollar Investment Scam
In this episode of Dollars to Dreams, host Tyler Hafford is joined by Penobscot Financial Advisors' Chief Operations and Compliance Officer, Hannah Tackett, for the first in a new series on cyber scams. They dive into the disturbing details of the $2 Million Illusion, also known as the Pig Butchering Scam, and share the story of "Fred"—a victim who lost his hard-earned savings to a sophisticated o
Hannah's Perfect Food Day in Portland, Maine
In this special food-themed episode of Dollars to Dreams, host Tyler Hafford is joined by PFA's Chief Operations and Compliance Officer, Hannah Tackett, for a delightful detour from financial talk into the culinary world of Portland, Maine. Hannah, an enthusiastic foodie, shares her ultimate day-long food itinerary through Portland, offering a personal and deliciously detailed take on the city's v
What It Means to be a Fiduciary and Why It Matters
In this episode of Dollars to Dreams, Tyler Hafford and Hannah Tackett tackle a core concept of their practice—and the trust they build with clients: fiduciary duty. Being a fiduciary isn't just a technical term or legal requirement; it's a guiding principle that shapes how Penobscot Financial Advisors engages with every client. Tyler and Hannah explain what it truly means to be a fiduciary, how i
What's New with MainePERS in 2025
In this episode of Dollars to Dreams, Tyler Hafford and Hannah Tackett focus on a system that hits close to home for many of their clients—and themselves: the Maine Public Employees Retirement System (MainePERS). Both Penobscot Financial Advisors' offices in Maine regularly help public sector employees like teachers, municipal workers, and state employees navigate this complex retirement system. T
Social Security Updates for 2025
In this episode of Dollars to Dreams, host Tyler Hafford is joined by Hannah Tackett, Chief Operations and Compliance Officer at Penobscot Financial Advisors, to unpack what's new with Social Security in 2025. Social Security touches almost every American household, and the 2025 updates include headline-making changes and some lesser-known details. The changes include a 2.5% COLA, updates to earni
What is a Recession and Are We Headed Toward One?
Tyler Hafford and Hannah Tackett of Penobscot Financial Advisors break down the real meaning of a recession—how it's defined, how it feels, and what the current economic data is signaling in 2025. The episode offers historical context and practical insight, from reflections on COVID's sharp downturn to today's tariff-fueled uncertainty. It delivers a calm, clear-eyed strategy for navigating potent
What's New in Tax Planning?
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 bi
Tax-Efficient Investing: 3 Smart Strategies to Lower Your Tax Bill
Tyler Hafford and Hannah Tackett break down three powerful tax-efficient investing strategies—Roth conversions, tax-loss harvesting, and asset location—in this year-end planning episode of Dollars to Dreams. With relatable explanations and smart examples, they show how being intentional with your investments and account types can reduce tax drag and boost long-term growth. Whether you're managing
Why Time in the Market Beats Timing the Market
Tyler Hafford and Hannah Tackett dive into the true power of compound interest in this episode of Dollars to Dreams, showing why consistent investing beats trying to time the market. Using simple analogies and real examples, they highlight how starting early—even with small amounts—can lead to massive long-term gains. But even if you're starting later, it's never too late to get on the right path.
Staying the Course: Smart Investing Through Market Volatility
In the premiere episode of Dollars to Dreams, Tyler Hafford and Hannah Tackett break down the emotional and strategic realities of market volatility. They explore why panic-selling can derail your financial goals and why staying invested through downturns is often the smartest move. Using real-world examples and behavioral insights, they offer clear, confident strategies for navigating rocky marke
MainePERS and Social Security
Tyler Hafford CFP® has Craig Joncas CFP® join the show to discuss the Maine State Retirement Benefit. He breaks down how the benefit is calculated and how it will impact your Social Security.
How you know it is time to Retire, interest rates and potential recession?
In this Episode of Financial Discretion Advised, host Tyler Hafford CPF® bring in Jim Bradley CFP® to talk about when someone might know it is time to retire. They dive into some personal experiences and what they commonly see with their clients. Additionally, the two dive into the murky waters of the interest rate environment and if we might tip into recession.
The Dollar and The Market
On this episode of Financial Discretion Advised Tyler Hafford CFP® brings in PFA's Portfolio Manager, Sam Chaplin CFA, to discuss what impact a strong Dollar has on the market. Sam breaks down how an extremely strong Dollar has created additional headwinds on the market in 2022 and what it might mean going into 2023.
Are we in a Recession?
In this episode of Financial Discretion Advised, Tyler Hafford CFP® brings on Lead Advisor Libby Mckay CFP® to discuss the topic of recessions and how it applies to today's environment. The two break down the current situation, how recessions have played out in the past and how it might impact your portfolio. For more information, check out Libby's blog on the topic - https://penobscotfa.com/are-w
To Dollar Cost Average or Not?
On this episode of Financial Discretion Advised, Tyler Hafford CFP® weighs in on a popular investment strategy - Dollar Cost Averaging and why it might NOT be the best way to get your money into the market
Recession right around the corner? Current Market Conditions, Inflation, War and the Fed!
In this episode of Financial Discretion Advised, Tyler brings in PFA's Portfolio Manager, Sam Chaplin, to talk about the current market conditions and if a recession is right around the corner. The two break down the recent action from the fed, inflation and the War in Eastern Europe.
Interest hikes like the 80's?? Power of Tax Deferral and the $400k mistake you may be making
In this episode of Financial Discretion Advised, Tyler Hafford CFP® talks about the rate hikes that are aimed to control inflation and how that compares to strategies used in the 80's. He also breaks down the impact of those hikes on our everyday lives. In the Financial Planning segment, Tyler explains the power of tax deferral as well as the extreme cost to delaying your investing strategy!
Russian War and the Market
"In this "out of schedule" podcast, Tyler Hafford, CFP® breaks down the state of the US stock market and puts the recent drawdown in historical perspective when it comes to Military Action around the world."
Frugal Parenting
Tune in to this Week's #FinancialDiscretionAdvised episode where Hannah shares some everyday parenting hacks to save money and Tyler reviews the financial tools available to parents.
Market Corrections, Fixing Social Security, HSA
In this episode of Financial Discretion Advised Tyler brings Chief Investment Office Jim Bradley back on to discuss the current market slide, the social security system and how we might be able to fix it. Additionally, the two also breakdown how using a health savings account can make a big difference in your financial planning. Try to fix social security yourself, and make sure to leave your sol
Alternative Assets, US Mega Caps, Financial moves for 2022 - Financial Discretion Advised
In this Episode of Financial Discretion Advised, Tyler brings on Sam Chaplin to discuss Alternative Assets, US Mega Caps, and some financial planning moves to set 2022 for success! Listen in as Sam brings his expertise on all these topics and more!
Omicron, Santa Claus Rally, RMD's - Financial Discretion Advised
In this Episode, Tyler had Jim Bradley back on to discuss some of the recent headlines and an important end of year financial planning topic. They explore how the Omicron Variant has impacted the market, and how coronavirus as whole has impacted the market. Jim gives some insight on some of the fads in the market, specifically the Santa Claus Rally. The Financial Planning topic on this episode is
Inflation, Crypto, Backdoor Roth
In this episode Tyler tackles some of the reasons for the recent rise in inflation, and how it can impact your portfolio. He also dives into the world of Crypto and how it is changing the investing landscape. The financial planning strategy on this week's episode is the Backdoor Roth.
Estate Planning
With Halloween coming up and the talk of ghosts, ghouls, skeletons, and death, Abrin and Tyler sit down to talk about estate planning strategies. Sit back relax and enjoy the conversation which also touches on favorite Halloween candies and the headlines about the debt ceiling, a trillion dollar coin, and Facebook being back in the news.
Questions of the Month
Abrin and Tyler discuss a variety of topics while answering common questions the advisors of our firm get all the time. Listen along and maybe grab an answer to a question that has been on your mind then submit your own questions.
In the Headlines
Abrin and Tyler have sifted through the news and picked out a few topics directly and indirectly tied to the markets and the economy for discussion. We've got inflation, we've got used cars, we've got a new jobs report, Robinhood IPOing, and Bezos making it to space all on the docket so tune in!
Fourth of July Special
As we commemorate the Fourth of July and the Declaration of Independence, Abrin and Tyler revisit why independence is important as an advisor and talk about financial independence in the context of the declaration.
Money Tips & Tricks
Abrin and Tyler have some fun with 10 small things anyone can do to help better their financial situation. 1. Pay yourself first 2. Bucket your money 3. Automate savings 4. Avoid investment fads 5. Take free money 6. Avoid the daily latte 7. Create a budget 8. Earn cash back using credit (responsibly) 9. Shop around 10. Buy wholesale/meal prep Plus one bonus tip snuck in there!
The UMaine Plan
With a little distance between them, Tyler in the Bangor office and Abrin in the Podcast room, the two discuss UMaine plan topics specific to a large subset of our firm's clients: University of Maine Employees. Strap in because this episode contains bad jokes and dad jokes - you have been warned.
Investment Account Taxation
Tyler and Abrin tackle the tax implications of withdrawing money from different types of investment accounts and take a deeper look at capital gains for taxable accounts.
Inflation
Tyler is out and Sam is in for this episode on inflation. Come meet another member of the team as Abrin and Sam talk about a pressing concern in today's environment: inflation.
Advisor Compensation w/ Special Guest Craig Joncas
Special Guest Craig Joncas joins Abrin and Tyler to talk how financial advisors get paid.
ESG Investing w/ Special Guest Jim Bradley
Jim Bradley enters the arena to discuss ESG investing with Abrin and Tyler. Join to learn more about how ESG investing has progressed over the years and how it can be incorporated into an investment strategy.
Maine Real Estate
Abrin and Tyler talk about the current state of the Maine Real Estate market, mortgage rates, and more on today's episode of Financial Discretion Advised.
Investment Planning Strategies
Tyler and Abrin are back to banter as they discuss the basic principles, fads, management styles, and transitioning to withdrawing assets in retirement.
Roth Conversions
Craig Joncas joins Abrin and Tyler to talk about Roth Conversions and Roth Conversion Strategies.
New Year, New Financial Planning Resolutions
Hello, hello! We hope everyone had a Happy New Year on this holiday themed episode. We are ringing in the new year with new mics and some tips on how to achieve financially related New Year's resolutions.
Things Your Crazy Uncle Was Wrong About at Thanksgiving
Abrin and Tyler discuss Thanksgiving dinner table financial planning questions and what planning tools they are thankful for this year.
ABCs of End of Year Tax Planning
Roth Conversions, Charitable Contributions, Tax Loss and Gain Harvesting... Oh my!
All Things Social Security
Special Guest Jim Bradley joins Abrin and Tyler to talk about how Social Security benefits are calculated, strategies for taking Social Security benefits, and how the system could be reformed in the future. To view the video with slides that are referenced in this episode, click HERE.
The Financial Planning Process
Join Tyler and Abrin as they lay out the six key steps to the financial planning process and stay until the end for a new friendly competition among hosts.
Teamwork is the PFA Way
Big thanks to all the team members for joining Tyler and Abrin on Episode 2 of Financial Discretion Advised. We had great conversations about the benefits of working as team to support clients - some serious and some not so much. Come get introduced to everyone and their roles within the firm. Enjoy!
What the F???
On this first episode of Financial Discretion Advised we will be talking about what it means to be a fiduciary in the financial advising world and under what circumstances an advisor must act as a fiduciary. Don't worry, audio quality and our performance will only get better from here.
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