
Pay Yourself First and 3 Other Money Lessons for Owners
Just because you make millions of dollars a year does not mean you pocket millions of dollars. On paper a job can look like a win. In practice you may be losing money on it and not find out until the bill shows up.
I learned most of what I know about money in business the expensive way, and I recorded the lessons as short solo episodes of The Purpose Chasers in 2022. Here are 4 of them in one place, with the full episodes to listen to. They are short. Listen to them in the truck.
1. Pay Yourself First (Ep. 66)
Everyone repeats cash is king. The truth behind it is that cash flow cannot be a guessing game. There has to be a mathematical equation in place to hit your margins predictably on every job, and that equation has to include the expenses most owners never think about until the invoice arrives, like renting equipment.
The formula I built inside my own companies is simple to say and hard to keep: never spend money you do not have in your pocket, meet the needs of the customer, complete the job, calculate every step accurately, and then pay yourself first. I gamified the financial state of the business so I always knew whether a company was healthy before I touched a dollar.
2. Making a Lot of Money Is Bad Without a Plan (Ep. 55)
A scarcity mindset in business leads to large tax bills. I know because I paid them. Once I got clear on my financial goals, my mindset shifted to how I was going to secure them, and the first move was hiring a real tax planner and bookkeeper.
That is Sarah Jones of Lenwood Hazel Group, who joined me for this episode. With over 15 years of experience, 3 master's degrees, a certificate from Cornell, an Enrolled Agent license and the Certified Tax Coach designation, she turned my finances from a guessing game into monthly reports that show the trends of the business. Tax planning and bookkeeping are the foundation, not the afterthought.
Sarah later became a client too. Here is what she said about that:
What Sarah Said After We Built Her Landing Pages
Sarah Jones had wanted to get her business online for a long time and did not know how to start a landing page. We built two full landing pages and every automation in Go HighLevel, then recorded a walkthrough so she was comfortable running it herself. In her words:
"He did a great job and I'll definitely be using him again."
More real stories on the Happy Check client results page.
3. Just Filing an LLC Is Not Safe (Ep. 56)
I tried to be my own attorney for years. It was a super painful and expensive lesson, and the fix was the same as the tax lesson: stop filling roles you are not equipped to fill. My business attorney, Nick Dupre, is board certified in estate planning and probate and has protected small and midsize businesses for 15 years.
The takeaways from our conversation: separate the work you are doing from the business that owns it, understand that a good contract keeps you out of litigation, know the liabilities that come with acquiring or taking equity in a company, treat a business attorney as an investment instead of an expense, and document everything.
4. Stop Showing Up for the Takers (Ep. 59)
Look at the last month of networking calls, Zoom meetups and get to know you follow ups on your calendar. How many of them moved the needle for you or your business? Lesson number 14 of what entrepreneurship has taught me: stop showing up for the takers, because your calendar opens up to serve the givers.
Most owners are bound to a calendar full of calls they do not want to take, often because they lead with insecurity and over deliver their value to people who will never give back. Set boundaries on your time, give without expectations, and keep your hours for the relationships you actually value.
The Money Lesson Underneath All 4
Every one of these episodes is about the same thing: stop guessing and build a system. The most expensive guessing game in my businesses was marketing, until I replaced ad spend with customer stories and took a company from -$403,276 in the accounts to $6.4 million in revenue on under $5,000 a month. That system is the Social Proof System, and it is the most predictable margin I have ever built.
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Want Marketing With a Predictable Margin?
On The Purpose Chasers I sit down with people who are building something that matters. In my business, The Happy Check, I help coaches, creators and service businesses turn that same kind of real story into video testimonials and content that bring in clients.
If you want to take your marketing to the next level, book an organic marketing audit call with me.
Or start with the free Happy Check book and learn who to ask, when to ask and how to use what they say.
Keep reading: fire your marketing company in 5 steps, how to scale with customer testimonials.

