Essays, aphorisms, and humor about life, technology, and success.

I’m not a guru and by my writing style you will see that I’m not an academic. In fact, by many standards, you are reading the story of a serial failure that has probably pissed through more money than you may have seen in your lifetime.

I decided to start this blog on as one of my resolutions for 2010. I took down all of the old posts and wanted to take this into a new direction. This blog is now for me, and anyone traveling a similar path in life.

This will be my personal journal to chronicle some of my experiences. I’m not trying to impress you as much as I am trying to hold myself accountable and vet out the things that are on my mind.

You probably don’t know me as I’m not a famous internet celebrity or guru. I’m just another guy trying to make a living. You may have seen me commenting on blogs, and even trying to figure stuff out in the tech forums. Aside from that, I’ve kept my life very private. And despite building a six-figure income online in the a little over a year, I feel that my accomplishments to date in the new media world have been quite trivial. There’s so much more to be done.

Many of you will find this boring and will not be able to relate. Either you are too young to have failed, too smart to make a mistake, or still pretending you’re a hitter. But I’m hoping that if you are the one person who reads this and has failed numerous times, and is still looking for a reason to pursue your dreams – this blog might inspire you to persevere.

I also write this knowing there will be critics and trolls quick to pounce upon my many mistakes and flaws that I will share with you. I’m not impressed by that, and can honestly say that I sleep good at night knowing that I create the kinds of publications and programs that my mom would be proud of, and that I have always given more than I ask in return.

I hope you enjoy reading about my adventures and subscribe to the RSS or email, but more importantly just take a second to say hey on twitter or introduce yourself at a conference. I’d love to here your story.

A Kid From Cleveland

My first money making venture was at age 9 pretending to be my 10 year old brother to become a newspaper carrier on the east side of Cleveland. I picked up routes for 2 papers and took on over 300 subscribers in the neighboring apartment complexes near my house.

I made pretty good money for a kid, even playing the big shot at the local York steakhouse in the mall with my buddies. I also quickly realized how much people depended on their content, even getting crazy when the paper showed up a few hours late because me and my wagon were stuck on the snowy sidewalks.

I got the computer bug around 1984 when a neighbor friend of mine got an Apple IIe and haven’t looked back since. Although my life has taken me through many detours including several career changes. I started my first real business was while I was in college which was a chimney cleaning and window washing business.

I put together a small crew of college kids that I supplied business to and spent all of my free time trying to drum up business. That was a great part-time business that taught me how to market and organize a team a very young age. I even dropped out of college to work the business full-time thinking I had found my calling.

Unfortunately, due to the seasonality (a lesson I won’t soon forget) I ended up having to get a job working at a local employment agency in sales. This turned out to be a blessing in disguise.

After a couple of years in the employment business (which I found fascinating in that I could make money for every hour that someone else worked) the concept of residual income took hold of my mind. At the age of 23 with my first mortgage payment staring me in the face and our first baby on the way, I quit my job and started my own employment agency with my tax return check (about $1,200) and one machinist on payroll.

I specialized in technical and manufacturing positions and I opened a few offices around Cleveland and was quickly making more money than I had ever imagined. The risk had paid off.

By 1994 at the age of 24 had my first $1 million dollar year with the agency. The secret to my success was that I got online and was one of the first employment job boards of that era. Coupled with the fact that I put every penny I didn’t eat back into payroll and grew the business. I was also very active in sales and customer relations which branded me and gave me great relationships with my clients. No employee every stole a single account after leaving my company.

Austin, TX – The 90’s DOT.com Legend

I spent most of the 1990’s in the employment business and toward the end of the decade I got lured in by the DOT.com bug after meeting a brilliant young tech guy from IBM that was launching his own employment related startup. Within months I got rid of my temp agency and moved to Austin for what was going to become a 7-figure internet bubble poster child of a business.

We hired staff, ate sushi every day for lunch, got a killer office with state-of-the art equipment, and cool trendy furniture. After one year and a shit load of money: 1) one of the co-founders was caught embezzling from us, 2) we couldn’t so much as get a website up let alone a working product to market, and 3) the last straw was that the bubble was bursting in early 2000 along with any hope of a concrete business plan for our company. It was over.

Back to Cleveland – The DUI That Made Me Rich

Humbled by the huge failure of my DOT.com I decided to regroup and take some classes. I hated having to rely on other people to innovate and wanted to have a better understanding of how everything worked.

Now living off of savings and with our third baby on the way. I had to find work so I approached a friend of mine about joining his family’s shopping center business. I was once again intrigued by a new world of possibility and massive wealth. Since my dad was a landlord while I was growing up I already had a basic knowledge of the business from hearing him talk about it. But my big break didn’t happen until the owner of the company I was working for got his 3rd DUI.

For most a DUI is a problem, but I saw an opportunity. I told my boss that I would drive him anywhere he wanted to go while his license was suspended and he fought his legal battle – he took me up on it since no one else wanted the job.

Over the next 9 months I learned more about the shopping center business from a self-made multimillionaire developer than I could in any MBA program. I even became a key player in the organization, built my first 100,000 sf shopping center, and was given a couple points in ownership upon completion. The real estate bubble was just starting to build in 2003, my youngest son (#4) arrived, and I was having a blast.

I also got the company online and learned that I could drive huge commission paying deals from leads on the internet.

Things were good for a while but I wanted MORE.

Sunshine and Shopping Centers

I ended up leaving the company in 2004 to participate in the real estate boom in South Florida. Shopping center owners pay upwards of $5 per foot to brokers for commission (ex: 10,000-sf store x $5 = $50,000 commission) and I was leasing over 100,000-sf per year. This was like shooting fish in a barrel. Plus, the fact that even to this day there are still very few commercial landlords know how to get leads from the internet. But I knew how to use this new medium for offline profits.

During this time I met up with a publicly owned REIT that had shopping centers all over North America. I used my internet marketing skills and salesmanship to help the company raise over $40 million dollars and take the company private. I even carved out some nice equity for myself along the way and then in 2007 the bottom started to fallout. Suddenly, money was harder to come by and I started putting my own cash into deals to keep going. This was a huge mistake.

In the last two years I’ve seen all of my hard earned equity in real estate evaporate before my eyes. And it’s not over. I had to make a move, fast. Shopping centers owners are getting creamed right now and fresh cash is still years off on the horizon.

Lucky during all of this I held onto a a little side business where I was trading domain names and developing digital communities. The internet once again had come to my rescue.

The New Media Mogul

The funny thing about my story is that any of the real money and success I’ve had in my life (regardless of the industry I was in) has been thanks in large part to my love and use of technology and the internet to solve common business problems combined with some real world skills. You see, most people will create a technology and try to find a use for it. My success and failure have shown me that you must first identify the business problem, then find or create the technical solution if possible. Many have this concept backwards and quickly fail.

Now my new business (which I will not promote here as it’s not the purpose of this blog) is focused on finding problems with everyday businesses and consumers and using new media and technology to deliver the solutions. After a slow start and an ongoing learning curve we have built a small media business with a six-figure income this year and look forward to scaling that up to seven figures in the next year or two.

I’m not the richest guy out here, in fact, I’m up to my eyeballs in debt and putting everything I can back into my business that isn’t nailed down – so my “net worth” these days is far from what it once was. But I see good stuff ahead. I will be discussing things I come across in my daily life that are helping me position for what I believe is the next gold-rush that has already started taking shape.

One of my strongest beliefs is that old market forces are subject to disruption. The coming decade will be the battle for Main Street and local business owners will have an advantage over global brands. If you are looking for some direction, here are a few areas that you should be looking at now:

• Local is the new global (look for more Glocal joint ventures)
• Brand = Reputation (not just a logo, living brands will be the standard consumers come to trust and expect)
• Entrepreneur Boom (you will see more startups than ever before as the people create their own jobs)
• Innovation Economy (a world with so many problems will reward those that start solving them – think eco-energy, medical, and education for starters)
• Instant Celebrity (each one of us now has the ability and the tools needed to become well know overnight in our field, but few are taking action)

I will also be sharing mostly personal insights on mindset and economic developments, as well as, trying to identify trends that may help small business owners position themselves for profits.

Thanks for reading my story. I hope you check back for more essays and videos again soon. I’m hoping to post a new essay at least once a month, but I will create sections for random things I find interesting in between and you can also find me on twitter @dennysugar.