I think many self-employed people knew from a very early age that they wanted to be their own boss or own their own business. I know that was certainly true for me. But at the same time there is a huge difference between "wanting" to start your own business and actually being willing to take the risks and make the sacraficies necessary to make that desire a reality.

There is definitely an attractive security, albeit often a false security, of having a well-paying regular employment job. For the vast majority of people, even ones who greatly desire to start their own business, a consistent predictable paycheck is a security blanket they could never voluntarily walk away from.

That's where I was a little luckier than some. In 2003, the mortgage lender I was working for as a Branch Manager suddenly went bankrupt. With no warning whatsoever, I showed up for work one morning and found out I no longer had a job. Not only that, but I also discovered I wasn't going to receive my last full month's paycheck or my yearly bonus (combined about $15,000).

That's when I realized the very thing preventing me from starting my own business - the "security" of a regular paycheck - was a complete farse. Something truly did change in me that day. I vowed I would never again put the well-being of myself and my family in someone else's hands. While working at this company I would often talk to the founder and CEO and think to myself "Christ this guy is a total idiot! Not only could I do his job, I could do it a million times better". I'm sure it was just youthful arrogance, but after losing my job and having no other immediate options, there was no question in my mind that I was going to start my own mortgage company.

The next month I had 2 employees, 3 desks, 3 phones, 3 computers, $25,000 charged on my credit cards, and the world's smallest mortgage company. To this day I look back and think to myself "what in the hell were you thinking?". Those first several months I lost a lot of sleep. I quickly discovered I had a lot to learn about running my own business. I made so many stupid mistakes I honestly cannot believe we didn't go bust instantly.

But we didn't and we eventually moved into a bigger office and added more employees. Luckily, my learning curve in owning my own business occurred during the exceptionally strong housing market of 2004-2006. There was enough money to buy my way out of my early mistakes and bad decisions.

Like all companies connected to real estate right now we have seen our share of highs and lows. But I just couldn't imagine ever going back to working a regular job. I just can't. I may not always own a mortgage company but I will always - until my death - be self-employed. I could never go back. Not to sound crass, but the best way I can explain it is like never having had sex without a condom and then one day pulling the condom off. Going back is never the same. :-)

For me, I would rather run my own business that's a failure then have a successful job working for someone else.

Absolutely! For years, Generation-Xer's like myself watched as our parents gulped down the Kool-Aid their corporate employers were selling them. Job security, pensions, 401k's, healthcare, etc. From Kindergarten to 12th grade, I watched my middle-management father suffer through 4 different "no-fault" job terminations. Each time he neither caused, nor could have prevented, being fired. And each time I watched my mother and father suffer through the terror, panic, depression, anxiety, shame, and hopelessness that comes with sudden job loss.    


Although not a "partner" in the traditional sense, I did agree to a venture capital investment once from a private individual. Worst experience of my life. It got so bad I eventually took 90% of my cash and assets so that I could pay him off and get out from underneath the agreement. This was one of those early collosal "bad decisions" I described in the other post. Personally, I would never again get involved with a partner or investor. From what I have heard from other businessowners, successful partnerships seem to be the exception and not the rule.  

Fantastic story Ryan. Congratulations 

You remind me of myself in many ways. Similar attitudes towards self employment, employers, risk, perserverence, self reliance etc. I really enjoyed reading your post.

What you wrote about the security of a pay check is the same thoughts that I had. It does also vary though with the generation and with the way people were brought up.

When I left a job to start my own business, I would get the same lecture from my parents every time I saw them. "You have no security, what if your business fails, where is your work insurances, where is your superannuation" blah blah.

But I always knew, even if I had no revenue or profit from business, I could always work at nights washing dishes, telemarketing etc. I always had a fall back plan. But when you are young and starting your own business, you don't care about security. It is just the adventure and drive that keeps you going.

Like yourself, my first year or so were less than glorious. But you hang in there, and it all works out in the end 

Well thank you. I appreciate that. It doesn't surprise me that we share a lot of the same personality traits. Like I said earlier, I think people are really "born" wanting to be self-employed. There's a certain combination of chacteristics, like you mention above, that all businessowners share - whether they own a billion dollar corporation or a small engine repair shop.


Boy, that's one thing I'm not sure I could have dealt with. It's hard enough dealing with your own self-doubts and insecurities when first venturing out on your own business endeavor - it sure doesn't help hearing them from your family as well.

My own parents were very supportive, so in that way I guess I lucked out again. My dad particularly - I think much like an atheletic father lives vicariously through their son's sports activities, I think my father did - and still does - the same thing on a business level. He always wanted to own his own business, but never had the money, opportunity, and/or "balls" to just do it. I can tell that's something he's always regreted. Now he's getting a second opportunity through me I suppose.

That said, there's always plenty of people (including sometimes close friends) who can't wait to see you fail. Over the years I've noticed a very consistent trend where the more successful you are the more people resent you. To give you an example, when I was 29, my wife and I built our dream home. Its a large home, its very nice, and its in an upscale and desireable neighborhood. For my 30th birthday, my wife and I decided to have a big birthday party at our new house. When I called my lifelong best friend to invite him he said "Sounds more like an excuse to show off your house than a birthday party". He eventually did show up to the party, but he just kept making these snide little comments the entire time and was so obviously enraged with jealously it basically ruined the party for my wife and I. He's been like a brother to me for as long as I can remember. In high school we used to daydream together about owning our own businesses and getting rich. We both did end up starting our own businesses. So far, mine has done better than his and sadly its basically ruined our friendship.

And that's just one of a million examples. A lot of people out there who aren't happy in their jobs or with their lives or who always wanted to own their own businesses too genuinely want people like me to fail and genuinely enjoy it when it happens. It gives them some sort of affirmation that plugging away at their miserable job is the right thing to do and taking a chance to have something better like me is the wrong thing I guess.   



Absolutely. You've got to be willing to do whatever it takes. You know, I tell this to my employees all the time - everyone in the world wants to make a bunch of money, but only a tiny fraction of people are actually willing to do the work to make it. Given the choice between being broke but not having to work very hard, and being wealthy but having to work your ass - a shockingly large number of people would rather be broke.

I'm in the process of a startup business right now. I've tried a few times before but lost interest because I spread myself too thin.

My advice -- get a few people to help with unique knowledge/specialty...that will make things move quicker.

i'm handling the online store, is all I can say at this point.

My parents are really good honest hard working people but ultra ultra conservative and terrified of risk. So the thought of their only child leaving a well paid job, after working for only 6 months, and starting a new business with no collateral behind him was not something they could really relate to. For them it was too risky that it would end in failure. But I took the opposite view, that for me not to try and give it a go, would be a failure. Different philosophies on life, neither wrong nor right.


Thats terrible that you lost friendships because of it. Envy is a terrible thing. I think many people judge themselves on how they compare with others. It is an insecurity thing. They feel happier about themselves if they are better off than someone, and feel jealous if the other person is better off. It is a terrible judgemental thing, that is inaccurate because so many different things make up a persons life, not just material possessions. I am always happy for people who are happy in life, no matter what they do.


I always find that people who are nasty about others or wish others failure, are unhappy with their own life. It is a form of expression of how dissatisfied they are with their life or life choices. Thus, I never take these comments or opinions personally.   



This is so true. The only difference between a person's position now and in 5 years time, is the actions they take. If nothing changes in their life, then their circumstances won't change.This applies to all components of life. I can be a procrastinator at times, but sometimes you just have to push yourself to get out of your comfort zone and take action.It can be hard but the experiences are worthwhile