“Regrets, I have a few.. but then again, too few to mention.” Maybe Ol’ Blue Eyes said it best, and as I start to write this post, I am thinking of just a few past experiences that leave blemishes on my life. Granted, I’m not even 40 and plan to live until at last 80, so I may revisit this over time if websites are still a thing by then.

One of the biggest regrets that I have revolves around work. I know that it’s romantic to watch movies and get choked up when the actor or actress says something along the lines of “you’re not going to look back on your life and wish you had worked harder… you will wish you spent more time with your family/friends…” This is probably not a marketing message, but unless you’re a wealthy family that can simply earn all the cash flow you need (and then some) from dividends, then work, sacrifice, and investing should be priority number one. As a society, we focus too much on gossip anyway, which is why the Kardashians are producing the level of money they do – it’s valuable to this society.

NOTE: I am not criticizing their family at all. Good for them for taking advantage of public opinion and exploiting it for massive gains. I think it’s awesome that they’ve played the cards dealt with precision.

I wish I would have worked more. I wish I would have focused on what matters when you work more. I haven’t had a normal job since 2001, mostly relying on my own abilities to add value to clients in return for payments. Sometimes those were split with employers or employees or partners or affiliates. In all cases, it was a commission only sink or swim model. I’ve spent too much time focused on learning and analysis (mostly because that was my value add) and too little time asking others to buy from me.

I wish I would have invested more. I owned Apple at a split-adjusted price of $1.95. I had Checkpoint Software at $14. I owned Bank of America at $5. So on and so on… but not enough money was put into them and I never held long enough.


My father died in August 2008, shortly after paying off his debts and starting a new business. Unfortunately, he had no life insurance, very little assets, and an 11 year old daughter. I was 28 at the time. Thankfully, he did have a small amount of social security that went to help my sister.

What he and my mother never figured out was how to sacrifice – aka save and invest. It was a trait that they passed down and one that stuck with me for far too long. I guess FDR’s administration had foreseen this potentiality in the 1930’s and wanted to avoid total calamity.

A few months after his death, my mom began collecting social security checks, directly deposited into the bank. At the time, the economy was in free fall with oil rising and stocks falling. However, I knew that the time to buy was when everything had crashed. I also knew that the S&P 500 was an easy investment to make on a monthly basis for most people.

The US Government was paying my mom $1,800 a month for the next 7 years, until my sister became an adult. It was a no brainer. So what’d she do? Start investing that monthly benefit into the SPY or VOO index fund. 7 years later in 2015, it was worth more than $264,000. Then, she held it and let it continue to grow to more than $391,000.


She used that money to consume, continue to live above her means, against the good advice she received. It’s a sad story and while wish that she had followed my advice back then, it’s usually in hindsight that people start to learn; however, life is about living.

I love my mom. I forgive her for not doing the right things with money because she was always a great person and fantastic mom. I also do not believe that children should take care of their parents. In fact, it should be the other way around and the parents should instill values and virtues in their young to be self-sufficient and use what they receive to increase it.

I went through a lot of self-imposed problems in my 20’s, have answered for it in my 30’s, and now as I’m looking at 40 square in the face, I’ve finally started to learn about sacrifice, regrets, and manhood.

Hedge Fund Challenge

Considering that the S&P index funds have proven to beat the majority of professional money managers including those elusive hedge funds, it’s baffling that there hasn’t been a greater shift to these automated accounts. The Warren Buffett bet didn’t help their cause at all. Plus, with new machine based money managers like Acorns, Betterment, and Wealthfront driving costs lower and lower, it will only get harder for new funds to raise capital.

Here’s my challenge to fund managers. Set the S&P 500 as the hurdle rate. Make it a moving target that you have to outpace every year. Charge a rate between SPY (0.09%) and VOO (0.04%) and split the profits above that rate in any year the SPY or VOO is positive. Or, to be really beneficial, make the hurdle rate the S&P 500 total return or 5% whichever is greater.

This way the investor is paying the same rate he or she would to have Vanguard or SPDR manage the money, with the added incentive of the 5% hurdle in down years, and half of the upside above the S&P 500 in good years. I’d like to see money manages begin to gravitate, at least those that are value oriented and deal mainly with individual equities.


With so many more people working past the government prescribed retirement age, I think about successful business people who are like titans that only get stronger and better with age. Maybe you’ve seen the following E*Trade commercial. While it’s hilarious on one sense, it’s a powerful point about why you should invest better.

No one actually wants to retire. They want to stop doing what they don’t want to do in order to pay the bills and pay for stuff they want, and start doing whatever it is they want to do. The only way to do that is to get enough capital working for you or be young enough that you have few if any attachments. This way you can work your ass off to build a business or career that generates the kind of income to invest.

In the end, without enough investments, you will never be free. I think that’s why so many people talk about capitalism as if it’s evil because they see business leaders who have sacrificed (generally speaking) to create the life they want.

That’s why retirement is a fake concept. It’s great to sell social security or IRA/401K plans, but very few attain freedom through those vehicles. That’s not to say you shouldn’t use them. Each has their place in society as we live it. It’s just that if you’re working to get to retirement, and you don’t enjoy your work, then it would be infinitely better to do something you love, even if that means not being able to have the things you do now.

Most people, including myself, have a lot more than we really need anyways. Of course, if you can do what you love and have all that you want, TWO THUMBS UP for you – nothing wrong with that either. It’s possibly the worst trait when people judge others by their own standards. What mattes is that if you’re 65 heading into retirement and don’t have enough, it’s time to get busy. Chopping wood in the winter sucks, but if you fail to do it (or to chop enough) in the fall, you have to get it done.

And, if you’re already in a job or business you love, why would you want to retire? Even if you want to do other things, keep doing what you love. Now, I get it. If you’re in a job that you are good at, don’t love, and it pays well, then screw it. Keep going, but please please please put money aside into investment vehicles that can outpace inflation – aka stocks, real estate, gold.

Any questions or comments? Get in touch… 


If you’re happy with 8% a year, then you should buy into an index fund like VOO, SPY, or FUSVX. Putting your money into a fund like this over regularly scheduled intervals will likely outpace 90% of investors during your lifetime. My job is to do 10% better each year for you.

To do your own homework, this book by Joel Greenblatt is a great starting point. Or, if you can handle more complex reading, Ben Graham’s Intelligent Investor or Warren Buffett’s collection of shareholder letters are the absolute best. Each of these money managers produced market beating results for decades.

My goal has always been to model and refine their strategies to produce similar or better results. Regardless of what asset type you’re purchasing, here are three questions that can lead to better investment decisions.

#1 – What is the future value of the asset?

This involves looking at historical data to analyze financial metrics, growth rates, and price multiples estimating value based on past performance, current comps, and future potential. As with most assets, the more unique the more valuable and use a different set of core tenets to estimate value to price for each opportunity. Value is determined in a variety of ways depending on asset class, but with most investments we simplify it to the amount of cash that can be produced over the remaining life of the investment, then judge that figure against the price paid today.

#2 – Can the asset’s value grow faster than the S&P 500?

With dividends the Standard and Poor’s index of 500 large publicly traded companies has produced an average of 10% a year for nearly five decades. An investment to us is one that beats inflation first, the market second. It’s rather easy for investors to buy an index fund and simply plug money in anytime he or she would like. Doing this will outperform the majority of their peers and the professionals.

#3 – What is the time frame for your investment?

For short-term trades like options, arbitrage, business/real estate flips, it’s important to know the time horizon. A 5% gain every 45 days turns into a 47% pre-tax return. For long-term investments, there might be months or years of flat to negative growth before seeing a massive return. What matters is that your money out brings back at least 1.15x money in every year, judged over a 3 to 5 year period. Even though the broad market may have periods of higher than average gains, normalized returns tend to be right under double digits for the stock market. And, as economies mature, count on lower returns.