The Story of My History in Business – Part 8 – Failures and Stress - Caleb Jones

This is the next installment in an ongoing series where I talk about my history in business starting all the way back when I was a child to now my mid-forties. Feel free to read parts zero, one, two, three, four, five, six, and seven if you haven’t yet to get some context. 

We last left off when I had just barely reached the point in my own full-time business where I was paying my own bills. Sort of… 

Summer 1997 

I felt poor.  

I was self-employed and making enough (though barely) to pay all of my taxes, minimal bills and living expenses, which I knew was an accomplishment and something most human beings never experience. But I didn’t feel successful. I felt a combination of excitement, pressure, stress, and frustration, all at the same time. I didn’t like that I felt poor, since I had already felt that when I was a small child. At the same time, I was optimistic for the near future. I knew that if I could get my income up to the point of paying my bills within about a year, I could certainly get to the “big money” in another year or perhaps even less.  

I knew that if I keep hitting it hard, I could reach my 10-year goal of making $100,000 a year by the time I was 28 years old. It was a goal I had set for myself back when I was 18 and leaving high school. 

The momentum in my business was pretty good. I could feel it and see it in my income every month. I was slowly picking up more clients. Existing clients were using me more often and for bigger jobs. 

I also contacted several other computer guys in the area, including many contacts I made while working with Ted. One of them was a guy named Ken who ran a small computer hardware company. Ken loved working on workstations and servers but hated going out on-site to deal with clients. I also liked working on computer hardware but knew that the real money and opportunity was working on-site with clients.  

As a test run, Ken started sending me out to some of his clients on a subcontractor basis. I was paid per hour at a lower rate, but it was free business that I really wanted (and needed!) so I didn’t complain. I made several other deals like this with other computer companies including two tech firms who were developing software for this new cool thing called “the internet” that I had just started using the year prior. 

More clients (though at a discounted rate), more business, more referrals. Things were looking good. 

I then proceeded to make one of the biggest mistakes of my life. I started dating an older woman named Lacy and married her later that year. I describe that story as in installment of my woman history here 

Dating her, falling in love with her, moving her into my house (along with her son who I later adopted as my own), marrying her, getting her pregnant then having a child with her later the following year pretty much destroyed my growth momentum in my new business at the exactly the wrong time. 

I was able to maintain the income, but growing it became extremely difficult. When I turned 25 in April of 1997, I was single, flexible, active, and free. By age 26 and a half at the end of 1998, I was a family man saddled a wife and two kids.  

My income had gone up a little, but not nearly as fast as I wanted or needed. After the baby came, Lacy quit her job and became a full-time mom. I was now a very young man with a new, growing but fragile business, and supporting a family of four all on my own. I was very stupid. 

Late 1997 and much of 1998 was hard financially. My personal expenses exploded. I started falling behind on my house payments. I started racking up debt. I started missing my quarterly tax payments.  

Terrified, I started working longer hours, really busting my ass, but with a family to support I wasn’t as focused as I was before. I loved my wife and kids, but their presence in my life was like an anchor I had to drag behind me. 

I finally visited a bankruptcy attorney. She said I was a “good candidate.” I didn’t like the sound of that. I decided not to file bankruptcy, since the concept of borrowing a bunch of money and just not paying it back seemed immoral to me. I just kept working harder and harder. 

I moved my downtown office to an office right down the street from my house in order to save money on gas and to be closer to the family. I tried several new marketing techniques. I started to do more formalized joint ventures with other consultants and computer professionals. This worked, and I made a good chunk of money.  

I also started dabbling in marketing with direct mail for the first time, following guys like Dan Kennedy who said that direct mail often worked best in industries where no one else was doing it. No other computer consultants in the Portland area were doing direct mail, so I gave it shot.  

My first mailing failed. I lost about $1,200, which was a mountain of money to me back then. I still remember how much that hurt. 

But I tried again, and this time I made a little money, netting two new (but small) clients. I knew that if it worked, even somewhat, then I could improve and do it again and again with better results. So, I started regular mailings.  

I listened to business and success cassettes in my car voraciously, and kept reading business books, always taking careful notes. I heard that learning how to be a good public speaker helped with your sales skills, so I joined Toastmasters and started attending regular meetings.  

To my surprise (since I’m an introvert and always have been) I found that I really loved public speaking. I actually started looking forward to my weekly Toastmasters meeting, especially if I was going to do a speech that day. It planted the seed for things to come in the future. 

Driven by both the negative (the fear of my tight financial position and supporting my new family) and the positive (my goals, of which I always reminded myself), I kept grinding. As stressed as I was, I knew the big money was just around the corner if I just kept at it.  

And I was right. 

To be continued 

5 Comments on “The Story of My History in Business – Part 8 – Failures and Stress

  1. Reading this makes me glad to be 23 and single. I can fuck whatever girl I want while working on my side business. I have lots of dumb guy friends in my age range that “are in love” with their girlfriends and can’t wait to tie the knot. These same people shit on me for being single, while they’re stuck having sex with only one woman. Once my idiot friends get married, they’re in for a lifetime of financial and emotional hardships.

  2. Reading this makes me glad to be 23 and single. I can fuck whatever girl I want while working on my side business. I have lots of dumb guy friends in my age range that “are in love” with their girlfriends and can’t wait to tie the knot. These same people shit on me for being single, while they’re stuck having sex with only one woman. Once my idiot friends get married, they’re in for a lifetime of financial and emotional hardships.

    You can be in love or have a girlfriend and still fuck other girls, it’s not mutually exclusive. And you also don’t need to tie a knot if you have those things. You are talking about mindset and external conditions those are separate things.

  3. You can be in love or have a girlfriend and still fuck other girls, it’s not mutually exclusive. And you also don’t need to tie a knot if you have those things. You are talking about mindset and external conditions those are separate things.

    I am aware of that, you are describing MLTRs, FBs, or OLTRs. Should have provided more context in my last post: my friends are shitting on me for not being in a monogamous relationships like they are in.

  4. I am aware of that, you are describing MLTRs, FBs, or OLTRs. Should have provided more context in my last post: my friends are shitting on me for not being in a monogamous relationships like they are in.

    Who cares about what they think, or if you do, you just can be shitting on them for not being able to fuck other girls. There are literally only 3 responses from other men when you say you have multiple girls: 1) they laugh and don’t believe you and then change the topic in a good mood, 2) they wow you and think you are some super cool awesome guy and and since they you are they’re bro and they tell others about you, 3) they give you an awkward look are silent for a moment and then change the topic.

    A different response like moralizing or saying it wouldn’t work or why I do that etc I literally only got from women or family. So if they respond that way you can follow up with a don draper facial expression and say are you a girl / my father? and then gulp your whisky and change the topic.

  5. Reading this makes me glad to be 23 and single. I can fuck whatever girl I want while working on my side business. I have lots of dumb guy friends in my age range that “are in love” with their girlfriends and can’t wait to tie the knot. These same people shit on me for being single, while they’re stuck having sex with only one woman.

    Yep! That’s how it works!

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