My Big Stupid Financial Failures

Lest you think I am some kind of financial god or something, let me set you straight.

The only reason I feel that I know anything about finance is because of all the mistakes I’ve made. And, when I say I’ve made mistakes, I mean massive botches.

  • Starting a business with a con artist selling snake oil (I didn’t know at the time, but I should have seen the signs), which cost me thousands of dollars and could have put me behind bars (he, fortunately, did go to jail).
  • Dumping potentially millions of dollars because I wanted to believe things like making cold calls, doing social media marketing, and talking my way into a sale were profitable strategies.
  • Going $50,000 in debt the second I turned 18 and could qualify for a credit card.
  • Investing in high risk stocks and stock options (I have friends who STILL do this…buying stock options and losing their shirts, but they won’t give it up).
  • Failing in at least 10 different industries before finally figuring out why (I’m a slow learner).
  • Getting a traditional merchant account and getting r@ped on fees.
  • Taking it up the @ss by banks giving me a “deal” on their business checking accounts – did you know you don’t have to pay any of the fees they tell you that you have to pay?
  • Getting taken advantage of by at least 9 different lawyers.
  • Not bothering to check the USPTO before naming my business or products (an epic way to get sued into the ground and buried forever in paperwork and fines)
  • Screwing up my taxes for years and having the IRS come at me with both barrels.
  • Threatened with lawsuits because I said something I probably shouldn’t have.


Recntly, yours truly was chatting with a friend who use to work for someone else, but who know owns her own business…she was telling me about her old boss who spent freely on things like office furniture and who knows what else.

Money just sorta seemed to slip through her hands. Problem was she didn’t really know where it all went. She didn’t have a good cash flow plan. She didn’t really have a solid idea about what to buy or why she was even spending money on all this stuff…

…other than she thought she needed it to look professional.

Racked up a lot of debt. Even though she seemed profitable, it sounded like she was just spinning her wheels. Here’s what I mean:

If you make $1 but spend $2, you’re in trouble Obvious, right? But, what if you save $1, but pay $2 in interest on debt…but spend that $2 over time…but still only make $1 for every $2 you pay out in interest.

A little more complicated but still a losing proposition isn’t it? This was what this business owner was doing.

This is actually the norm tho.

Most people have some debt. They’re paying interest on that debt. Even if they’re saving money, they’re backsliding.

How dost thou get out of this mess? Well, you create a solid cash flow plan. Lots of ways to do this. I wrote a short eBook (available on Amazon) that lays it all out for you (including a fill-in-the-blank template). That’s one way, but not the only way (although, call me biased, I do think my way is the SIMPLEST way).

Next, you start redirecting interest you’re paying to banks and credit card companies back into your own pocket. So, instead of paying $2 in interest to your credit card company, you do a u-turn and shuffle it back into your savings.

In other words, you eliminate your dependence on banks, credit card companies, and pretty much every other type of financing. And, when you’re borrowing $1, and $2 is being put back into your savings, you’re effectively earning the interest and profits a bank would have made off you.

That will solve the problem very, very, quickly.

If you want to know how to do this, get on my email list and let’s rock and roll.


David Lewis, AKA The Rogue Agent, has been a life insurance agent since 2004, and has worked with some of the oldest and most respected mutual life insurance companies in the U.S. during that time. To learn more about him and his business, go here.