Bankers, Techies, And Doctors: You’ll Never Get Rich Working For Someone Else

Although I estimate an entrepreneur needs to make at least 35% more to replicate his or her day job income to run in place, I’m truly beginning to realize after two and a half years how much more upside there is to entrepreneurship than to working for someone else.

I came from the world of banking where 23 year old graduates with one year of experience can clear $100,000 no problem. Despite ascending from Financial Analyst, to Associate, to VP, to Director within 10 years, and earning Director level compensation for three years before leaving, I still wasn’t able to earn and save enough money to buy my dream home in Kahala, Oahu.

Dream House In Kahala, Oahu, Hawaii

Contemplating on never being able to afford my dream home

The above is a picture of me sitting on a lanai, looking down the southeast coast of Oahu towards Koko Head. The home is on Blackpoint Road in the exclusive Kahala/Diamond Head neighborhood. Since I was a kid, I’ve always dreamed about living here one day. But I’ve come to realize my childhood dream will likely never come true.

The asking price for this 6,000 sqft Kahala home with 4 bedrooms and 4 bathrooms is $3.5 million ($583/sqft). The lower level is a 1,800 sqft rental apartment that is going for a below market rate rent of $2,500 a month. The main house is therefore not that huge. $3.5 million is actually great value given the view and the size of the house. Other houses in Kahala are easily asking for $900/sqft or more.

If I had $4 million cash, I would buy this house in a heartbeat. It needs at least $300,000 in renovations given it is quite dated. But the lanai and the spectacular view are priceless. All I think about when I’m looking for my dream home is being able to sit outside in 72-85 degree weather with an ice cold beer and write about various adventures. 

Should I Buy A Fixer-Upper Property?

Home Remodeling Gut Job

Breathe in fresh sawdust air

“Forget money. Remodeling is the number one cause for divorce.” – Anonymous

Before my current house, I had never bought a fixer-upper before. The most I did in the past was build a new bathroom out of a closet, put up a wall to create an en-suite bathroom, and remodel my ground floor by adding a shower and blowing out a center divider so one could fit a bed. Oh, I also changed all of my windows, which wasn’t so bad.

After my remodeling activities, I swore never to do another remodel project again because it kinda feels like hell on earth. But that was almost 10 years ago.

After getting ferociously outbid on a particular piece of property ($1.2 million ask, went for $1.8 million), I decided to look away from nicely done properties. There seems to be a massive embedded premium for new or recently remodeled properties that I wasn’t willing to pay. All I really wanted was a view, gosh darnit it. The property itself almost seemed secondary!

The Best Place To Rent A Vacation Property In Lake Tahoe – The Resort At Squaw Creek

Lake Tahoe Summer At The Resort At Squaw CreekWinter is coming and I’ve just renewed my season pass at Squaw Valley, Lake Tahoe! One of my favorite activities in the world is writing for a couple hours in front of a fireplace in the early morning, hitting the slopes for four hours in the middle of the day, and then relaxing in an outdoor hot tub with a couple cold beers. One for me, one for you.

Lake Tahoe, California is one of my favorite places in America. The other two favorites are San Francisco and anywhere in Hawaii. Lake Tahoe is situated roughly 205 miles away from San Francisco and it’s a place I’ve been going to for amazing skiing/snowboarding during the winter and golfing, hiking, swimming, biking, and fishing during the summer since 2001.

Most people think of Lake Tahoe as a winter destination given the 1960 Winter Olympics were hosted in Squaw Valley USA. Squaw is one of the largest mountains with a 2,850 foot vertical; a top elevation of 9,050; 4,000 acres of skiable area and 270 trails after joining forces with Alpine Meadows in 2012. The mountain is so big that even during peak holiday weekends, there’s hardly ever a wait for the lifts when they are all open. Squaw is great for beginners and advanced skiers alike.

But if you’re a summer lover, summer in Lake Tahoe is even more beautiful! Every year I spend 4-5 weeks up at my place during the summer and fall for a writing retreat. I love to hike and there are scenic trails all around. 

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!

Why Home Remodeling Always Takes Longer And Costs More Than Expected

Amazing, Expensive, KitchenMy general contractor, who is also my tennis teammate, was making fun of me for spending $6,000 for replacing my 40 year old gravity furnace that was lined with asbestos. I needed to replace all my ducts and vacuum seal my house for a day to prevent any asbestos from escaping as part of the replacement and permit process.

“I could have done it for $2,000!” he said as he tried to make me feel bad about my decision.

So when my general contractor came back to me with a bid of $9,000 to paint the interior of my house, patch, tape, and sand all holes in the walls, I almost threw up in amazement. My house has some nice crown moldings and standard baseboards, but everything else is pretty normal. “$9,000 is a great price,” he said with a serious face.

Because I thought $9,000 was ludicrously expensive, I declined his bid and found another fella I worked with in the past for $7,000. After he discovered I was going with another fella, my general contractor then came back to me and said I was wasting my money because these new guys he knows can paint my interior for only $5,800!

What the HELL! How is it possible that he honestly thought $9,000 was a good initial price when he now says he can do it for $3,200 less (36%) after I found someone else? Once again, he’s trying to make me feel bad for spending more than I should. He was hoping I’d take his bait at $9,000, and was gambling that I had no other resources. Little did he know that I’m the most resourceful person ever. If I am wronged, I will go to any length to fix the situation.

Everything began to unravel after this incident.