25+ years of finance experience in less than 5 minutes

Eighteen minutes. That’s how much I missed seeing the New Year’s Eve ball drop by.

I walked into our daughter’s room, told her goodnight, marched into our bedroom, and promptly fell asleep.

I have mixed feelings about treating each new year as a special event. On one hand, I do see it as a perfect time of year to evaluate everything and set goals, not resolutions, for how I will attack the year. I even have a file in my Notion dashboard called “2024 Operating Model” where I establish rules of engagement for the year.

For example, one rule, that I started last year, is that I try to do something creative or active if I’m anxious or frustrated. Doing one of those two things will almost always calm me down. Give it a whirl.


Writing is one of my creative outlets. Over the past week or so I’ve put down 11,197 words towards my next book, Stress-Free Finances.

In the book I am sharing everything I’ve learned in over 25+ years in the finance industry. That’s a lot of time and I’m fortunate to have picked up a lot of lessons along the way. Still, there are always opportunities to learn more.

For example, just last week I was working on a $1.6M loan for the purchase of a liquor store. The deal fell through and I would have caught it earlier had I done a better job analyzing the asking price compared to the value the business was demonstrating on its books.

Other times, my experience pays off when working on something finance-related. Like when I made my annual IRA contribution. Every year, if we have excess cash, I invest the maximum, this year it’s $6,500, into my and my wife’s IRAs. One reason I have a mental trigger to do that at the end of the year is that investment is tax deductible. This year I decided to put my full contribution into an S&P 500 fund. I knew it was performing well and my experience told me I’d get an immediate lift. Sure enough, I’m up 8% in about one month.

Those types of financial decisions are second nature to me. But, you don’t need 25+ years in finance to make smart financial decisions. Pareto’s Principle, commonly known as the 80/20 rule, does apply to finance.

So, today, I’m going to distill those 25+ years of experience into a quick 5-minute read.


The 20% of finance knowledge that matters

Here are the few things that matter when it comes to succeeding in finance. Get these down and you will be ahead of most people. With one caveat. You can’t just understand them, you have to act upon them.

Personal Finance

  1. Spending money = investing - As often as possible, when you are spending money, try to think of it in terms of whether that expense improves your financial picture or hinders it.
  2. Assets > income = As long as your basic income needs are met, you should be putting your money into growth assets. Preferably assets that produce money as passively as possible. Good examples - real estate, index funds. Bad example - 99% of cars.
  3. 50/30/20 when in doubt = 50% of your money should go to needs, 30% to wants, and 20% saved. i.e. budget.
  4. Total cost of ownership - when you buy something like a car or home, it’s important to think about the total cost of ownership. Most people only think about the loan payment. That’s a mistake. For example, having a home comes with utilities, internet, TV, gas, water, waste, yard maintenance, repairs, furniture, and all kinds of other expenses.
  5. Control your emotions - most of the financial mistakes people make are centered around bad decisions driven by their emotions, especially their egos. No one needs their house to look like it was decorated by Joanna Gaines. You want it, you don’t need it. How often are people coming to your house anyway?

Business Finance

  1. Understand basic financial statements - Profit/Loss statement = revenue and expenses; Balance Sheet = assets and liabilities; Cash Flow = sources and uses of cash. Your P/L does not equate to how much money you have made!
  2. Debt vs. equity capital = Debt comes from lenders. Lenders expect to get paid back, principal and interest, repeatedly, often monthly. Equity comes from investors. Investors expect to get paid back from an acquisition, or public stock offering. Lenders give you money based on past financial performance. Investors give you money based on expected financial performance. Investors don’t invest in ideas. Ideas are a dime a dozen. They invest in people with a track record of proven execution.
  3. Marketing/Sales are the key skills - I had a mentor once who said, “There is no problem that five new customers won’t fix.” It doesn’t matter how talented you are at your profession. If you can’t find and close deals then you don’t have a business, you have a hobby.

But, Jonathan, how do I pick the right stock investments?

How are cap rates calculated for commercial real estate?

Which cryptocurrency is going to spike next?

That’s the problem. All those fancy finance tips you are trying to follow, they don’t mean a damn thing if your foundation isn’t strong. Do you want to get better a picking individual stocks? Learn how to analyze the financial statements of those companies.

If you want to boil down all of this advice, and everything else I know about finance, into only one actionable step, focus on #5 above - controlling your emotions.

While I can’t help you there, I do have a bunch of resources to help with your personal and business finance questions.

Thank you for subscribing!
Please check your inbox for a link to confirm your email address.

Read past issues

May 05
This isn't 2008. But, it's not that much better
Apr 20
Market Whisperer: Knowing Your Customer Better Than Investors
Apr 14
Energized > Rested
Apr 07
Numb the pain, silence the teacher
Mar 31
The Myth of the Big Exit
Mar 23
Growth Gears: Equity vs. Debt - Fueling a Startup’s Journey
Mar 16
A candid conversation about fear
Mar 09
The Technical Product Managers Guide to Go-to-Market
Mar 03
My goal was 100 financial plans. I did 10x that goal.
Feb 25
Poor MVP, no one likes you
Feb 24
Beyond Bytes: Why Interpersonal Skills are the New Power Tools for Success
Feb 17
This one question changed how I looked at contingency plans
Feb 10
From $100k -> $75M - this week's fundraising lessons
Jan 27
The next big finance opportunity
Jan 20
This is how long a startup funding round lasts
Jan 09
How I'd market a loan broker business
Jan 02
25+ years of finance experience in less than 5 minutes
Dec 28
How to have a stress-free relationship with money
Dec 17
How to buy a business with little money down
Dec 12
Want to 10x your business? Try the strategy that most people fear.
Dec 05
Why being loan-specific as a loan broker is best
Nov 28
The Power of Micro Markets
Nov 19
Defining success criteria helps remove analysis paralysis
Nov 12
Lessons from acquisitions
Nov 07
My business plan cheat code
Oct 28
Everyone is missing the real point about being overworked
Oct 22
Why you should have a "How to work with me" manual
Oct 18
Selling eggs - my quiet ambition
Oct 13
Breaking Free from 'Meh': The Hidden Impact of a 7 Rating in Life
Sep 24
From Software Engineer to Commercial Loan Broker
Sep 23
A personal message about the importance of your health
Sep 16
Is the SBA 8(a) program going away?
Aug 21
What is a search fund?
Aug 14
My guidelines for speaking engagements
Aug 07
The Ultimate Guide to Picking the Perfect Lender for Your Business
Aug 05
Built to sell - pricing strategies that work
Jul 22
My framework for building impervious value propositions
Jul 12
How to force tradeoff decisions
Jul 09
How I'd Start a Freelance Business Today
Jul 05
The Bookends of Product Management
Jun 28
From the C-suite to Product; How I got here and what you can learn from that
Jun 17
My Digital Detox Experience
Jun 10
AI copywriters wrote this blog post
Jun 03
The SBA Just Made Business Acquisitions Easier
May 27
The power of index investing funds
May 20
The most important skill for entrepreneurs
May 06
I churned out 46,000 words in 90 days using this writing process
Apr 29
⏰ NOW is the time to turn your finance career into entrepreneurship!
Apr 22
How to build your own financial plan in under 1 hour
Apr 15
Define your audience first, then design your product
Apr 08
Getting a business loan just got harder
Mar 25
This one question is jet fuel for productivity
Mar 24
Are the rate hikes over?
Mar 18
This tool removes decision fatigue
Mar 11
The one stat keeping us out of a recession
Mar 05
One key reason raising startup funding is so hard right now
Mar 04
My framework for quickly launching profitable products
Feb 16
What’s the average business loan interest rates?
Feb 13
Everything you need to know about business loan rates
Feb 10
This one tool made me a better entrepreneur
Jan 25
This one-pager is perfect for brainstorming business ideas
Jan 18
Stop making this mistake with your startup’s target market
Jan 11
Powerful tools for researching competitors
Jan 08
User persona template demo
Jan 04
They should take my Marketing degree away
Jan 01
How to confidently charge your worth
Oct 02
Building wealth with Restricted Stock Units (RSUs)
Sep 11
What I’ve learned as a startup analyst for an angel investing syndicate
Jun 24
My favorite economic analysis tools
May 29
Which SBA Loan Has the Lowest Down Payment?
May 01
The Power of a Decision Matrix
Apr 24
Things to consider when buying a business
Apr 17
Buy a Business vs. Start One
Mar 31
How do Micro SBA Loans work?
Mar 03
Common Investor Term Sheet Components
Feb 15
3 Step Process for Generating Business Ideas
Feb 06
Thoughts on <my first Angel Investment>
Jan 11
Lessons from writing over 1,000 words per day
Jan 06
There Are Two Main Types of Business Plans
Dec 09
The Best Pitch Deck Templates