Jesse Cramer
138 episodes listed below
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[Top 1% Personal Finance, Retirement, and Investing Podcast] Why is personal finance so complicated? The internet is flooded with personal finance "experts" sharing short-sighted, error-prone advice. But long-term financial success requires thoughtful, patient, and well-researched strategies. Hosted by Jesse Cramer, a former aerospace engineer turned fiduciary financial advisor in Rochester, NY, "Personal Finance for Long-Term Investors" simplifies complex financial planning topics. With relatable stories, in-depth research, and practical tips, Jesse helps you master personal finance planning for families, make smart decisions about tax-efficient investing, and build strategies for retiremen…
Based on 6 episodes we listened to · June 2026
Jesse Kramer turns retirement, tax, and investing questions into patient planning lessons for listeners playing the long game.
Personal Finance for Long-Term Investors - The Best Interest is a practical Business & Finance pick for listeners who want planning work explained slowly enough to follow.
You want the Roth-conversion math before future-you starts yelling from a tax form.
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Short reviews from the PlayNext desk, based on the episodes we processed.
Retirement looks like a date until the real triggers start to matter.
The episode treats retirement as a decision shaped by trade-offs, not a neat finish line. Jesse and Jeremy Kyle walk through how the timing can shift from what people first expect, with 59.5 and 62 standing out as key trigger points.
A practical framework for retirement withdrawal decisions and tax tradeoffs.
Jesse Kramer frames retirement withdrawal planning as a practical sequence of decisions, moving from a straightforward indexing question into decumulation, the order of operations, and sensible ways to sell investments to fund retirement.
A calm reset for listeners who value discipline over market noise.
Peter Lazaroff and Jesse Kramer keep the episode grounded in what investing feels like when markets turn, rather than in guessing where they are headed.
A practical money episode built around a personal, process-first framework.
Jesse Kramer uses episode 125 to move through personal finance in a way that feels anchored in one household rather than a glossy theory of money.
A plainspoken AMA on tax planning, cash drag, and why waiting on the market can cost more than it feels like.
Jesse Kramer uses his 14th Ask Me Anything to work through a few corners of financial planning that people often talk past one another on, especially the line between legal tax planning and anything that starts to drift toward gray illegality.
Jesse makes a clear case against market timing, then broadens it with Bill Yount's late-starter perspective.
Jesse argues against market timing by using one clean April 2021 example: an investor waits for a dip, the S&P 500 moves up first, and the later pullback still leaves the entry above where it began. That keeps the point concrete without getting lost in theory.
A practical checklist for judging whether an advisor deserves trust.
This episode treats advisor selection as a check on process, not presentation. Jesse Kramer walks through Jason Zweig's 19 questions and adds two more of his own: succession planning and the cadence a client should expect.
Risk feels different once investing has left scar tissue.
Jesse Kramer spends the hour on a plain but uneasy question: why the same risk can feel manageable to one investor and threatening to another.
Paul Haavardsrud unpacks Canadian money stories, from ski-hill VIP pricing to French butter tariffs.
Real-estate freedom, taught in plain numbers.
Jesse Kramer opens episode 120 of Personal Finance for Long-Term Investors by saying "I am weak, so are you," then uses YouTube, social media, sugar, and food marketing to show how designed systems exploit attention and appetite.
Jesse Kramer opens with a listener review and gets into money psychology with Hannah Horvath.
Roth is not an automatic yes.
Jesse frames retirement as a moving target.
Jesse Kramer’s episode 109 of Personal Finance for Long-Term Investors collects spending stories from Joe Salcihai, Justin Peters, Jordan Grumet, and other financial creators.
Jesse Kramer frames episode 125 as a Christmas reflection on money.
Jesse Kramer’s episode 133 brings on Ruben Miller, founder and chief investment officer of Peltoma Capital Partners, to explain why great investing decisions can look wrong for years.
Jesse Kramer, host of Personal Finance for Long-Term Investors and a fiduciary wealth manager, uses episode 119 to explain special needs planning for parents and grandparents.
Jesse Kramer, host of Personal Finance for Long-Term Investors, lists “dumb” money moves he is personally willing to accept, starting with a 5% to 10% sandbox account for stock picks, Berkshire Hathaway, and crypto ETFs.
Jesse Kramer uses episode 131 of Personal Finance for Long-Term Investors to argue that annuities usually trade away too much return for too little certainty.
Jesse Kramer records a bonus episode on April 10, 2025 to answer 15 tariff questions while the S&P 500 is down about 14% from its February highs and about 7% from the April 2 "Liberation Day" level.
Jesse opens with a listener review and a nod to the show’s education first mission.
Jesse Kramer of Personal Finance for Long-Term Investors reviews Jason Zweig's seminal Wall Street Journal article 'The 19 Questions to Ask Your Financial Advisor.' Jesse methodically walks through the 19 questions, explaining Zweig's proposed ideal answers and adding his own commentary from his experience as a fee-only fiduciary advisor at Cobblestone Financial Firm in Rochester, New York.
15-year mortgage costs half the interest but nearly $1000 more per month
Time, not timing, is the investor's greatest ally.
You'll regret not spending time with people you love far more than you'll regret not having money.
Jesse Kramer opens with a review of the week, then moves into his ninth AMA.
Jesse Kramer welcomes Peter Lazaroff back to talk about staying disciplined when markets feel unsettled.
Jesse Kramer frames retirement around two ideas: change is the only constant, and a retiree's finances can be organized like a 10-event decathlon.
Jesse Kramer uses episode 121 of Personal Finance for Long-Term Investors to answer an AMA question about direct indexing, a retirement timing question from Kevin, and a decumulation question from Isaac.
Jesse Kramer keeps the episode measured.
Jesse Kramer frames episode 132 as his fourteenth Ask Me Anything.
Jesse Kramer opens with Benjamin Franklin's line about knowledge paying the best interest.
The first year of retirement carries more sequence risk than any decade before it—bad markets in early years damage your long-term retirement success far more.
Episode 129 of Personal Finance for Long-Term Investors (Best Interest podcast), an AMA episode hosted by Jesse Kramer.
This episode analyzes a 2023 retirement survey comparing pre-retiree expectations with post-retiree realities, revealing key disconnects in areas like home satisfaction, social connections, health, and identity.
Jesse Kramer uses this bonus episode to unpack where tax strategy can go sideways.
Jesse Kramer spends this episode pointing out where investors, planners, and DIY people tend to get tripped up.
The host replays an interview with Fritz Gilbert about the non-financial aspects of retirement, emphasizing life problems beyond the math.
This episode explains Monte Carlo analysis as a stress-testing tool for investment portfolios, clarifying its uses and limitations.
Host Jesse Kramer answers listener questions on financial planning, investment management, and retirement planning, including a question about financial implications of the California wildfires.
Host Jesse Cramer interviews Morningstar's Christine Benz about retirement planning insights from her book.
Host Jesse Kramer introduces a discussion on positivity and mental health in personal finance, beginning with a philosophical detour on ancient Cyreniac hedonism.
Jesse Cramer discusses the importance of having financial conversations with aging parents, tailored to their age and stage of life.
This episode introduces the FIRE movement, defining financial independence and how to achieve it through saving and investing, with an upcoming interview with Brad Barrett from Choose FI.
Jesse Kramer explains common tax mistakes and the intersection of taxes and investing for long-term financial success.
Host Jesse Kramer and CFP Rob Bradley discuss Warren Buffett's 2023 annual letter to Berkshire Hathaway shareholders, extracting key investing and life lessons.