How To Overcome Money Guilt

Couple Gazing In The Fields At Stone HengeMy parents came to visit me for only three short days recently and I miss them already. One of the reasons why I wanted to leave my stressful job in finance was to spend more time with them. I flew back to Hawaii four times in 2012 and three times in 2013 to visit for two-to-five weeks at a time. But our first meeting of 2014 was in September.

Totally my fault. Life seems to always get in the way.

Ever since going to college, I’ve longed to make my parents proud. My goal was to do well in school so I could earn enough money to support myself, a family, and them. They took care of me for the first 22 years, it’s only right I take care of them.

Some children have no problem accepting financial help from their parents as adults. That’s probably because they weren’t bad like me. I got in a lot of trouble as a teenager, and I really feel guilty for giving my mother so much heartache. I wanted to make up for all the money they spent on me by proving they didn’t raise a dead beat, but someone who could be independent as soon as he graduated college.

I also suffer from money guilt because I grew up in developing countries for the first 13 years of my life (Philippines, Zambia, Malaysia, Taiwan), and frequently went to China and India for work. Every time I’m about to buy something I don’t need, I think back to the times when I witnessed destitution. Every time I eat, I try and eat more slowly in order to be mindful of the starving.

Developing countries are full of hope and growth, but the juxtaposition between the haves and the have-nots is very stark. The poor are extremely poor and the rich are obnoxiously rich. You want to help, but after a while of helping, you come to the realization that the poverty is endless – like trying to catch a rain drop moments before a monsoon washes you over.

The Cheapest International City In The World: San Francisco

9,500 sqft for only $8.9 Million in Presidio Heights, SF

Guess the price of this 9,500 sqft, SF home.

I have been everywhere, and it is clear to me that San Francisco is one of the cheapest cities in the world based on its wealth creating potential. So many of my friends who live in New York City or around the country like to say that the median rent and home price in San Francisco are our country’s highest. It’s simply not true. Rent and property prices in Manhattan are the highest AND they only get to enjoy the outside for six months a year! Related: East Coast Living: Is It Really That Horrendous?

If I had to pay $2,500 a square foot for a condo in Greenwich Village, I’d be a little bitter too about equally amazing SF property costing 40% less. Heck, you can even get panoramic ocean view properties in San Francisco for under $800 a square foot. There’s no other city in the world that can boast such value.

The media have a great way of misleading the public because they like to take averages and extrapolate. I am in the trenches, actually visiting open houses in NYC and SF and bidding on places. I’m also a landlord who is very in-tune with market rents and wages for the 22-35 year old crowd. Based on the rents and incomes I’ve seen, San Francisco is affordable if you can land one of the many tech, internet, software, healthcare, consulting, and finance jobs.

I was just in London for Wimbledon, and places in Knightsbridge and Chelsea make Pacific Heights in San Francisco feel like Costco prices!

A Great Way To Save More Money: Visualize Your Broke-Ass Lonely Self

Graffiti Long Island No Money No Honey

5Pointz, Long Island City

Ever since I was in the 4th grade, I’ve had this mild obsession with staying in shape. There was this girl I liked in gym class that I so wanted to impress, but I already had a gut as a nine year old! So imagine my dread when it was swim season and I had to sit down next to her in only my trunks. I couldn’t wait for the teacher to blow her whistle so I could jump into the pool and exhale. I was always so envious of the bony kids who didn’t have to suck in their guts.

I never did get the girl. I blamed genetics and my lack of courage to say, “Wanna get an ice cream sandwich during recess?” All throughout secondary school I decided to get into better shape because I knew I couldn’t be poor and out of shape at the same time. That would be a disaster.

Nowadays, I no longer care as much about being in good shape because I’ve usually got my clothes on. Women don’t seem to care for hunky dory guys anymore. A nice smile, an engaging personality, a job, a car, a stack of Benjies, and a two bedroom condo with a view of jumping dolphins in the horizon will do. Can you really blame single 40-year old guys who are still having the time of their lives?

“Even if I don’t need him to take care of me, I’d like to know he can provide the life I want to lead,” mentioned a couple female friends who are 8’s, but settled for 6’s.

If we men can’t stay fit, then we must be able to at least generate enough wealth to provide. Being unfit in wallet and in wealth leads to loneliness. This is our curse from society, which I’ll discuss more in an upcoming podcast.

“No money, no honey,” as the saying goes. 

What Is Venture Debt? An Investment With Higher Yields And A Lower Risk Profile

Venture Debt vs. Venture Capital Returns

Venture Debt vs. Venture Capital Returns

One of my favorite investment strategies is the barbell strategy where I invest in lower risk companies or indices to hit singles and doubles while concurrently investing in more speculative companies to hit potential home runs. I’ve structured my after-tax investments to be more low-risk through structured notes, and my pre-tax investments in my rollover IRA, SEP IRA, and Solo 401k to be more high risk. Given my pre-tax investments can’t be touched until 59.5 without penalty, I find it easier to take more risks with such funds.

My investments are solely a mixture of equity and fixed income to keep things as simple and straightforward as possible. My main goal is to come up with an appropriate asset allocation for my age and risk-tolerance, and let the investments perform as they may. Spending energy trying to beat the S&P 500 is a fool’s game. I’d much rather be traveling, playing tennis, building my online business, or writing with my spare time.

I’ve recently invested into a new investment vehicle I’m very excited about. It’s called venture debt. For those of you who are accredited investors who like the barbell investment strategy as well, I think you will appreciate learning about venture debt in this article.

The Cause Of Conflict: Money, Entitlement, And Poor Etiquette

Team Photo At The Mission Playground, SF

Team Photo At The Mission Playground, SF

You might have heard about all the Google bus protestors in the Mission District as techies move in and cause rents to rise. Long-time residents are displaced by landlords who want to evict and sell their buildings to buyers who turn around and rent the same units for market prices. Multi-unit buildings are under rent control, which allows for rents to rise by no more than a small percentage a year, usually under 2%.

On the one hand, the landlord should be able to sell their building and maximize profits if they so choose. On the other hand, how do we take care of the residents, especially older and disabled residents who might not have anywhere to go because market rents are double their existing price? It’s a messy, messy situation that is causing a lot of strife.

I’m a landlord, but I’ve never faced this problem before because I’m just buying property to live in. Only after living in the property for many years (10 years as is the case with my latest rental) will I put the property up for rent because I don’t ever want to sell. I would feel terrible buying in an up-and-coming neighborhood with the idea of booting out long-time tenants for profit. Forget that. There are much more harmonious ways to make money than disrupting other people’s lives.

Here’s a video that is causing a lot of uproar in San Francisco that I’d like for you to watch. This altercation is a prime example of what happens when money, entitlement, and poor etiquette come into play. Notice the racial divide as well. Having tact and better communication skills can go a long way to avoiding conflict.