*BIG* Career Changes & A Personal AMA | Jesse Cramer - E150

*BIG* Career Changes & A Personal AMA | Jesse Cramer - E150

Author: Jesse Cramer September 2, 2026 Duration: 1:04:13

Jesse shares an exciting new career update. And to celebrate 150 episodes, we're doing a unique AMA episode.

Looking for a financial planner?  → PlanWithJesse.com

First, Jesse shares an exciting new career update. He has joined a new financial planning firm - as an advisor and an owner. The new firm, Rialto, is focused on serving people JUST like those who read *The Best Interest* and listen to Personal Finance for Long-Term Investors. 

Justin Peters takes the microphone around and asks Jesse the questions listeners have been sending in for months—the ones that don't quite fit into a traditional personal finance show. From career changes and family life to engineering, hiking, favorite books, pizza toppings, and what's next for the podcast, you'll get to know the person behind Personal Finance for Long-Term Investors. Along the way, Jesse also shares lessons from leaving aerospace engineering to become a financial planner, why he chose advising over becoming a full-time content creator, how he thinks about risk in his own life, and why long-term thinking extends far beyond investing.

Key Takeaways:
• The biggest piece of financial advice he would give differently today.
• Growing up in rural New York and why Rochester still feels like home.
• How the University of Rochester shaped Jesse's confidence and career.
• Why Jesse chose financial planning over becoming a full-time content creator.
• Favorite travel destinations, books, movies, and hiking adventures.
• A preview of a potential new podcast format featuring real listener financial case studies.

Key Timestamps:
(01:34) – Jesse's New Chapter
(04:43) – Leading with Financial Planning
(07:58) – Who Are Jesse's Ideal Clients?
(10:29) – Celebrating 150 Episodes
(12:23) – Who's on Your Team?
(13:50) – What Are Jesse's Frivolous Purchases?
(15:06) – When Will Jesse Be Financially Independent?
(18:06) – What's the Worst Financial Advice Jesse's Given?
(20:29) – Would Jesse Ever Leave Rochester?
(22:35) – What's Jesse's Family Situation?
(27:24) – University, Squash, and Effort
(32:32) – Space Telescopes, Engineering, and Results
(37:28) – Starting The Best Interest Blog and Becoming a Financial Planner
(43:03) – Why Not Just Be a Content Creator?
(45:33) – Making a Career Change
(50:43) – Travel
(53:14) – Books and Movies
(56:55) – 46 Peaks
(59:00) – Jesse's Pizza Philosophy
(01:00:36) – What's Next for the Podcast?

Key Topics Discussed:
The Best Interest, Jesse Cramer, Wealth Management Rochester NY, Financial Planning for Families, Fiduciary Financial Advisor, Comprehensive Financial Planning, Retirement Planning Advice, Tax-Efficient Investing, Risk Management for Investors, Generational Wealth Transfer Planning, Financial Strategies for High Earners, Personal Finance for Entrepreneurs, Behavioral Finance Insights, Asset Allocation Strategies, Advanced Estate Planning Techniques

Mentions:
Website: https://rialtowealth.com/
LinkedIn: https://www.linkedin.com/in/jesse-cramer-11b58155/
Mentions:
Deep Work: Rules for Focused Success in a Distracted World by Cal Newport
A Random Walk Down Wall Street: The Best Investment Guide That Money Can Buy by Burton G. Malkiel
https://libbyapp.com/
https://www.harpercollins.com/blogs/authors/chris-crutcher
https://bestinterest.blog/e123/
https://finconexpo.com/ 

More of The Best Interest:
Check out the Best Interest Blog at https://bestinterest.blog/
Contact me at jesse@bestinterest.blog
Need a financial planner?  → PlanWithJesse.com 

The Best Interest Podcast is a personal podcast meant for education and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.


Navigating the world of money can feel overwhelming, with a constant stream of conflicting tips and trendy, quick-fix schemes. Personal Finance for Long-Term Investors-The Best Interest cuts through that noise. Host Jesse Cramer brings a unique perspective to the conversation, transitioning from his background as an aerospace engineer to his work as a fiduciary financial advisor. This podcast is built on the principle that genuine wealth isn't built overnight through speculation, but through consistent, well-reasoned decisions made over decades. Each episode delves into the mechanics and mindset required for that journey, exploring topics like retirement planning, intelligent investing, and the behavioral aspects of managing money. You'll find discussions that go beyond surface-level advice, examining the "why" behind proven strategies and how to apply them to your own life. The tone is conversational and grounded, avoiding financial jargon in favor of clear explanations. It’s a resource for anyone tired of the hype and seeking a sustainable path forward. By focusing on evidence-based ideas and patient execution, this podcast aims to provide listeners with the tools and confidence to build a secure financial future on their own terms. Tune in for a thoughtful, long-term approach to personal finance that prioritizes your best interest.
Author: Language: English Episodes: 50

Personal Finance for Long-Term Investors
Podcast Episodes
Less Wealth, More Certainty: Why Annuities Are Rarely Worth It (E131) [not-audio_url] [/not-audio_url]

Duration: 53:03
In this expansive and deliberately contrarian episode, Jesse takes on annuities—not with a sales pitch or a blanket dismissal, but by putting them under a rigorous planning lens rooted in risk, probability, and real reti…
Don't Let a Scary Economy Cause Bad Retirement Decisions (E130) [not-audio_url] [/not-audio_url]

Duration: 51:36
Jesse is joined by Cullen Roche—financial writer, macro thinker, and founder of Discipline Funds—for a clear-eyed conversation about how money actually works, why so much financial commentary gets it wrong, and how inves…
"Isn't My Portfolio the Same as My Financial Plan??"  (AMA, E129) [not-audio_url] [/not-audio_url]

Duration: 41:18
On Jesse's 13th AMA episode, he steps back from tactics and returns to first principles, answering listener questions that cut to the core of what financial planning actually is—and what it is not. He begins by dismantli…
11 "Bad" Financial Moves...That Are Actually Fine (E128) [not-audio_url] [/not-audio_url]

Duration: 41:28
In this candid solo episode, Jesse walks through a series of financial decisions that look "wrong" on paper but make complete sense when viewed through the lens of real life, values, and tradeoffs. Using personal example…
"The Most Important Number" in Your Retirement?! (E127) [not-audio_url] [/not-audio_url]

Duration: 53:37
Jesse is joined by Jeremy Keil—Certified Financial Planner, Chartered Financial Analyst, author of Retire Today, and host of the Retirement Revealed podcast—for a wide-ranging conversation that reframes how people should…
Will You Retire in 2026?? (AMA, E126) [not-audio_url] [/not-audio_url]

Duration: 50:46
On Jesse's 12th "Ask Me Anything" episode, he opens the year by tackling the questions that tend to surface when calendars turn and retirement feels closer than ever. He begins with a thoughtful exploration of whether "t…
My Ghosts of Financial Past, Present, and Future (E125) [not-audio_url] [/not-audio_url]

Duration: 51:11
In this Christmas episode, Jesse steps back from year-end checklists and market noise to tell a more personal story—one shaped by the "ghosts" of his financial past, present, and future. He begins with the early experien…
The Scenario When HSA's Are a *BAD* Account (AMA, E124) [not-audio_url] [/not-audio_url]

Duration: 50:11
On Jesse's 11th "Ask Me Anything" episode, he unpacks four questions that sit at the center of real-life financial decision-making. He starts with a grounded look at the 15-year vs. 30-year mortgage debate, cutting throu…
Should "Coast FI" Be the *Real* Goal? (E123) [not-audio_url] [/not-audio_url]

Duration: 38:53
Jesse sits down with Andy Hill—personal finance educator, podcast host, and creator of Marriage, Kids, and Money—for a candid conversation about building wealth while building a life you actually enjoy. Andy shares how a…
Why Retirees Struggle with Health Over the Holidays (E122) [not-audio_url] [/not-audio_url]

Duration: 47:44
Today, Jesse is joined by Dr. Phil Pearlman—psychologist, behavioral finance veteran, and founder of the Pearl Institute—for a conversation about how long-term health and long-term wealth are two sides of the same coin.…