Most investing advice sounds like it was written by robots in suits who’ve never actually struggled with money. But every once in a while, you meet someone who gets it. Someone who speaks human. That’s Jesse Cramer.
I recently sat down with Jesse on the podcast, and what started as a casual chat about investing turned into one of those conversations where you actually learn something useful. Jesse runs the Best Interest blog, hosts the Personal Finance for Long-Term Investors podcast, and helps families build what he calls “behavior-proof” financial plans at Cobblestone Capital Advisors.
But here’s what makes Jesse different: he wasn’t always a money guy. He used to design space telescopes. Yeah, you read that right. The dude went from focusing light from distant galaxies to helping people focus on their financial future. And honestly? That transition taught him more about money than any finance degree ever could.
From Space Telescopes to Portfolio Building
I had to ask Jesse about this wild career shift because, let’s be real, going from aerospace engineer to financial advisor isn’t exactly a typical path. Turns out, there’s a pretty cool story behind it.
Jesse spent seven years working for one of the largest telescope manufacturers in the country, a company that used to be part of Kodak in Rochester, New York. His specialty? Something called optomechanics, which is basically the mechanical design of lenses and the structures that hold them in place. Think about it, when you’re trying to capture images from incredibly far away, the way you hold those lenses matters. A lot.
While he was crushing it in the aerospace world and making decent money, Jesse realized something. He had no clue what to do with that money. His dad gave him some basic pointers about getting the 401k match (solid advice, by the way), but beyond that? He was flying blind.
That Ah-ha Money Moment
Then came that moment we’ve all had. You check your retirement account and suddenly see a number that makes you go, “Whoa, I’ve got some real skin in the game here. I better figure out what this is all about.”
For Jesse, that number was big enough to make him start digging deep into personal finance. He became a full-on nerd for Mr. Money Mustache, John Bogle, and all the classic personal finance books and blogs. Pretty soon, he was the go-to finance guy at his engineering firm. Younger employees would hit him up with questions, and he’d write these detailed email responses.
Smart move? He turned those emails into blog posts. The blog led to a podcast. And eventually, Jesse realized something important. He actually enjoyed helping people with their money more than he enjoyed his 9-to-5 engineering gig. Four years ago, he made the jump to financial planning full-time.
Engineering Principles That Actually Apply to Your Finances
Here’s where it gets interesting. I asked Jesse if any of his engineering background actually helps with his client work today. His answer? A hundred percent yes.
Engineers are trained to think in systems. They understand feedback loops, tolerances, and what happens when things fail. Jesse brought up a perfect example. So, in engineering, when you’re designing something, you build in margins of safety. You don’t design a bridge to hold exactly the weight it needs to hold. You design it to hold way more than that because you account for unexpected stresses.
The same principle applies to money. You don’t build a retirement plan that works perfectly only if everything goes exactly as planned. You build in cushion. You account for market crashes, unexpected expenses, and life throwing you curveballs.
Jesse also mentioned something that really stuck with me. In engineering, when something fails, you don’t just throw your hands up and quit. You analyze what went wrong, adjust your design, and try again. But with money? Most people make one mistake and either give up completely or keep making the same mistake over and over.
The engineering mindset of iterative improvement and learning from failure is exactly what people need when managing their finances. But weirdly, most folks don’t apply it.
The Real Secret to Long-Term Investing
I know people want the magic pill. The secret stock pick. Or the insider strategy that’ll make you rich overnight. But here’s what Jesse and his team of eight Certified Financial Planners have figured out after working with hundreds of families:
“The foundation of every successful financial plan is knowing the money coming in and the money going out.”
That’s it. That’s the tweet.
Jesse put it perfectly: “If you don’t know that, there’s nothing that any expert in the world can do for you that’ll be precise enough to help you sleep at night.”
It sounds simple because it is simple. But if you’re not doing it, you’re missing out on the most foundational aspect of your financial plan. You can have the fanciest investment strategy in the world, but if you don’t know your cash flow, you’re just guessing.
And look, I get it. Tracking your spending isn’t sexy. It’s not fun. But neither is waking up at 3am wondering if you’ll ever be able to retire. One of those problems is way easier to solve than the other.
Why Most People Trip on the Psychology, Not the Numbers
Here’s something Jesse said that really hit home: most people eventually learn the numbers. They figure out what a 401k is, what index funds do, how compound interest works. The math isn’t the hard part.
The psychology? That’s where people stumble.
We talked about the value of meeting other people on the same financial journey, whether that’s at in-person meetups, conferences like FinCon, or through online communities. There’s something powerful about hearing real success stories and real struggles from actual humans, not just reading statistics in a book.
Jesse mentioned listening to Choose FI and hearing about events like Camp FI and Chautauqua, where people at different stages of their financial journey come together. Some are ahead of you on the path. Some are behind. But everyone’s navigating the same psychological challenges.
Because at the end of the day, the hardest part about money isn’t understanding the S&P 500. It’s convincing yourself not to panic sell when the market tanks. It’s resisting lifestyle inflation when you get a raise. It’s staying disciplined when everyone around you is financing new cars and taking fancy vacations they can’t afford.
The psychology remains the struggle.
The Overlap Between Financial Planning and Giving Back
One topic we dove into that I wasn’t expecting? Philanthropy. And not in a preachy, “you should donate more” kind of way. More like, “hey, if giving is important to you, there are some really smart ways to do it.”
Jesse’s been learning a lot about the overlap between financial planning and charitable giving, and honestly, I had no idea how many options existed. We’re not just talking about writing a check to your favorite charity (though that’s great too).
For example, if you donate appreciated stock directly to a nonprofit, you get a double win. The charity receives the full benefit of your donation without having to pay capital gains taxes. You get the stock off your balance sheet without paying capital gains yourself. And you get to deduct the full value of the donation on your taxes. Everybody wins.
Leaving a Legacy
There are also creative options with estate planning, like setting up trusts that provide you income while you’re alive and then leave the remainder to charity after you pass away. If you’re worried about longevity risk (not knowing how long you’ll live), these structures let you be generous without risking running out of money.
Jesse mentioned having a conversation with a local Choose FI listener who’s really philanthropic. The guy made an interesting observation: the financial independence movement might have a bit of a giving problem. Everyone’s so focused on being frugal and hitting their FI number that some people living off the 2.5% rule are staying up at night worried about running out of money when they could comfortably be cutting multi-thousand dollar checks to their favorite causes.
Now, it’s their money. They can do whatever they want with it. But if you’ve reached financial independence, you’re living in pretty amazing circumstances. Taking just one-tenth of one percent of your 4% rule and giving it back? That’s 2.5% of your annual spending going to causes you care about. Not a bad place to start.
I actually want to plug something here. Check out Yield and Spread if you haven’t heard of it. It’s geared toward the FI community and helps people make pledges to donate to causes important to them. The platform and community is not about keeping you accountable in some guilt-trippy way. It’s just a tool to help close that gap and make giving a normal part of your financial plan.
What Does Behavior-Proof Investing Mean?
Throughout our conversation, Jesse kept coming back to this idea of “behavior-proof” investing. So what does that actually mean?
It means building a financial plan that works even when you’re emotional. Even when the market’s crashing and in a decline, and your neighbor just bought a new boat and you’re feeling FOMO. Even when you’re scared or excited or confused.
Traditional finance assumes people are rational. But we’re not. We’re emotional creatures who make decisions based on fear, greed, and what our friends are doing. A behavior-proof plan acknowledges that reality and builds systems to keep you on track anyway.
That might mean automatic contributions to your retirement accounts so you’re investing before you even see the money. It might mean setting up your portfolio in a way that’s diversified enough to weather market storms without you feeling the need to make panic moves. It might mean working with an advisor who can talk you off the ledge when you want to sell everything because the news is scary.
The best investment strategy isn’t the one with the highest theoretical returns. It’s the one you’ll actually stick with for 30 years.
The Real Magic Pill (That Isn’t Actually Magic)
At the end of our conversation, I asked Jesse what his one takeaway would be for listeners at any stage of their journey. Whether they’re just starting out, well on their way, or feeling discouraged about ever retiring.
His answer was perfect, even though it’s not what people want to hear.
People want a magic pill. They want the super secret information they haven’t heard before. But after working with a team of eight CFPs doing comprehensive financial planning, Jesse’s seen the pattern. The foundation always comes back to the same thing:
Know the money coming in and the money going out.
Track it monthly. Track it quarterly. However works for you. But track it. Because without that foundation, no expert in the world can build you a precise enough plan to help you sleep at night.
It’s simple. But simple doesn’t mean easy. And if you’re not doing it, you’re building your financial house on sand.
Engineering Your Financial Freedom
What I love about Jesse’s story is how it proves that financial expertise doesn’t always require some crazy fancy finance degree. Sometimes the best money advice comes from people who approached the subject from completely different angles.
Jesse brought his engineering mindset to personal finance and discovered that the same principles that help you build reliable telescopes help you build reliable financial plans. Margins of safety. Iterative improvement. Learning from failures. System thinking.
But most importantly, he learned that the numbers are the easy part. The psychology is where the real work happens. And the best plans are the ones that account for human nature instead of pretending we’re all rational calculating machines.
If you want to learn more from Jesse, check out his podcast, Personal Finance for Long-Term Investors. You can find it on any podcast player. He also sends out a weekly newsletter with his new content plus top links he finds around the internet. Sign up at bestinterest.blog.
And remember, long-term investing that actually works isn’t about finding the secret strategy. It’s about building simple, behavior-proof systems and sticking with them even when it’s boring. Especially when it’s boring.
Remember, boring is what gets you to financial freedom.
Stay focused, stay disciplined, and keep your horns up and eyes on the long game.
This is a wonderful write up. Thank you, Chris!!