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Artwork for Dollars to Dreams: Planning with Purpose

Dollars to Dreams: Planning with Purpose | Penobscot Financial Advisors

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We break down the complex world of financial planning into real, relatable conversations. Hosted by Tyler Hafford and the team at Penobscot Financial Advisors, we explore how thoughtful planning can help you take control of your finances—so your money can support the life you're living today while building the future you've always imagined. To view our disclaimers and privacy policy: penob... more

PublishesTwice weeklyEpisodes58Founded6 years ago
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BusinessInvesting

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Artwork for Dollars to Dreams: Planning with Purpose

Latest Episodes

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 ... more

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: ... more

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 Inves... more

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 ... more

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Recent Guests

Tucker Grinnell
Client Service Associate, PFA
Penobscot Financial Advisors
Episode: PFA Celebrates the Holidays! (Sam Chaplin and Tucker Grinnell)
Yelsh Gebreselassie
Portfolio administrator at Penobscot Financial Advisors
Penobscot Financial Advisors
Episode: PFA Celebrates the Holidays! (Yelsh Gebreselassie)
Jim Bradley
Senior advisor looking back at traditions and 2025 reflections
Penobscot Financial Advisors
Episode: PFA Celebrates the Holidays! (Julie Willette and Jim Bradley)
Julie Willette
Team member sharing family traditions and holiday memories
Penobscot Financial Advisors
Episode: PFA Celebrates the Holidays! (Julie Willette and Jim Bradley)
Craig Joncas
Advisor at Penobscot Financial Advisors
Penobscot Financial Advisors
Episode: PFA Celebrates the Holidays! (Craig Joncas and Jessie Dolmage)
Jessie Dolmage
Advisor at Penobscot Financial Advisors
Penobscot Financial Advisors
Episode: PFA Celebrates the Holidays! (Craig Joncas and Jessie Dolmage)
Sam Chaplin
Chief Investment Officer, Penobscot Financial Advisors
Penobscot Financial Advisors
Episode: AI V.S. DOT COM
Hannah Tackett
PFA's Chief Operations and Chief Compliance Officer
Penobscot Financial Advisors
Episode: Social Security Updates for 2025

Hosts

Tyler Hafford
Host of Dollars to Dreams, Penobscot Financial Advisors
Sam Chaplin
Chief Investment Officer, Penobscot Financial Advisors

Reviews

3.7 out of 5 stars from 6 ratings
  • Well worth the subscribe

    Great advice from a great team! Love you guys

    Apple Podcasts
    5
    hinman4373
    United States6 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Well produced with clear practical takeaways.
Content balances technical detail with accessible storytelling.
Warm, approachable host style with solid financial guidance.
Guests bring diverse expertise and real-world context.

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Talking Points

Recent interactions between the hosts and their guests.

PFA Celebrates the Holidays! (Craig Joncas and Jessie Dolmage)
Q: Jessie, what was your high, low of 2025 and what's on the docket for 2026?
Her high was trying new things, including surfing and exploring new activities; a low was having a family visit canceled due to illness and a chaotic travel episode; looking ahead, she plans to continue surfing and explore knitting and reading more in 2026.
PFA Celebrates the Holidays! (Craig Joncas and Jessie Dolmage)
Q: Jessie, can you tell me about your favorite childhood memory around the holidays?
Jessie shares a memory of waking up before dawn on Christmas Day, waiting for the moment to discover Santa's gifts, a ritual described as torturous yet magical in hindsight, capturing the excitement and family traditions of holidays.
AI V.S. DOT COM
Q: Is current AI enthusiasm a bubble similar to the dot-com era?
The hosts acknowledge hype and the potential for overestimation in the near term, but argue the AI space has stronger fundamentals today with durable, cash-flow-rich leaders, higher barriers to entry, and ongoing data advantages that differ from the dot-com dynamics.
Social Security Updates for 2025
Q: Can you tell me a little bit about what's happening with Social Security in 2025?
The 2025 COLA is 2.5%, signaling inflation cooling and a return toward normal price increases, with notable implications for both average and maximum-benefit recipients. Earnings limits and Medicare adjustments also shift, affecting how much retirees can earn before benefits are reduced and how much premiums might rise, depending on income. Overall, planning should focus on understanding your expected benefits, coordinating with a partner, and modeling different claiming ages to optimize your retirement income.

Audience Metrics

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Frequently Asked Questions About Dollars to Dreams: Planning with Purpose

What is Dollars to Dreams: Planning with Purpose about and what kind of topics does it cover?

This show breaks down financial planning through relatable, practical conversations led by a team of financial professionals. Episodes cover core investing principles, the evolving role of technology (including AI) in planning, and real-world planning strategies for long-term goals like retirement, risk management, and tax efficiency. The format often blends expert insight with human-centered storytelling, guest perspectives from inside a financial advisory firm, and holiday or topical themes that connect planning with everyday life. It's probably especially valuable for listeners who want straightforward guidance, concrete takeaways, and a thoughtful view on balancing technology with personalized planning. A notable strength is how the hos... more

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Dollars to Dreams: Planning with Purpose launched 6 years ago and published 58 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Dollars to Dreams: Planning with Purpose?

Recent guests on Dollars to Dreams: Planning with Purpose include:

1. Tucker Grinnell
2. Yelsh Gebreselassie
3. Jim Bradley
4. Julie Willette
5. Craig Joncas
6. Jessie Dolmage
7. Sam Chaplin
8. Hannah Tackett

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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