Jesse Cramer: Smart Planning Beats Smart Investing
Jesse Cramer is the founder and voice behind The Best Interest Blog and the Personal Finance for Long-Term Investors Podcast, where he educates over 25,000 DIY investors and financial advisors every month. With a background in mechanical and aerospace engineering, Jesse has a gift for making complex financial topics surprisingly simple. Today, he brings that same clarity and precision to his work as a fiduciary, fee-only advisor at a wealth management firm in Rochester, New York.
In this episode, Leonard and Jesse discuss:
Journey from aerospace engineer to personal finance educator
Why understanding your real spending habits is critical to retirement planning
How the engineering mindset helps break down complex financial systems
The most common financial mistakes people make—and how to prevent them
How podcasting and financial education can empower individuals at all life stages
Key Takeaways:
Many individuals drastically underestimate their actual monthly spending, leading to flawed financial plans that feel solid—until the numbers don't add up.
Financial planning mirrors a spider web: every financial decision pulls on another thread, revealing an intricate system where nothing exists in isolation.
While investments often take center stage, the true value lies in holistic planning—blending tax strategies, risk protection, and long-term income coordination.
Clarity begins with humility: assuming no prior knowledge, effective educators break down complex topics to their first principles, avoiding industry jargon.
When people truly understand both their risk exposure and spending habits, they gain the confidence to make intentional, informed financial choices.
“ It's the idea that I don't want to say investing is table stakes in our industry because it's probably not, but I think investing can be the easier part of our job... I just like learning all the cool stuff in the planning world that I didn't know before.”
-Jesse Cramer
Connect with Jesse Cramer:
Website: https://bestinterest.blog/
LinkedIn: https://www.linkedin.com/in/jesse-cramer-11b58155/
Connect with Leonard Raskin:
Website: https://www.raskinglobal.com/
LinkedIn: https://www.linkedin.com/in/leonardraskin/
Facebook: https://www.facebook.com/RaskinGlobal
Email: lraskin@raskinglobal.com
Leonard’s BOOK: FiduciWho?: What a Real Fiduciary Will Tell You about How to Protect, Grow, Enjoy, and Transfer Your Wealth
Show notes by Podcastologist: Angelo Paul Tagama
Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.