Never Crush a Little Dream

How pursuing a little dream can result in unexpectedly big things

I handed the CEO my resignation letter.

“What will you do now?” he asked coldly.

I replied that I had some options. It was just time for me to move on.

“Oh,” he stated sarcastically, “are you going to work on that little newsletter thing of yours?”

I didn’t know that he was aware of my side hustle, but I resented the belittling tone.

“Well,” I replied sarcastically, “that LITTLE company makes more money than you pay me.”

His jaw dropped open. “Are you kidding me?”

Dreaming Small Can Achieve Big Things

About a year before I crafted that resignation letter, I stood at my workbench gazing out the window. My mind was far from the woodworking tools and home projects laid out in front of me.

I was thinking about this little idea, my little dream for a little company.

I owned a small mortgage brokerage, and each week, I wrote a newsletter designed to send to my referral sources, such as realtors, attorneys, and others in the real estate world. A friend who owned another mortgage company asked if I could do the same newsletter for him. Since he’d helped me get started in the industry, I was happy to give back.

If he wanted one, perhaps others wanted one too? Would they pay me for it?

Ignorance can sometimes be better than knowledge.

I know that the way that I started that little company is far afield from what experts advise today. I didn’t create a business plan, build a lean canvas, research competitors, or honestly put much forethought into it at all.

I had an idea, and I wanted to know if people would buy it.

Fortunately, I had an inactive second LLC that had a merchant account. So, I had everything that I needed to launch.

I posted a little description of the product with a sample newsletter, plus a signup form in Yahoo Groups. A few days later, the fax machine buzzed, and my first customer signed up. Yes, fax machine, this was 2003, after all!

I was ecstatic! Someone was paying me to do what I was already doing.

Over the next two weeks, two more loan officers signed up. I confirmed that my idea was something people would buy. It was only three people, but it was a start.

I stood there at my workbench, thinking through the potential.

“What if I could get two loan officers in each state?”

At the time, I couldn’t even think of my product becoming more popular than that. I did the math.

Two loan officers times fifty states times $20 per month (2 X 50 X $20)

“Holy crap! That’s two grand a month!”

The thought of just a little more work than I was already doing and pocketing an extra $2,000 a month was awesome!

Then the proverbial shit hit the fan. I’d invested a significant amount of time and effort with a homebuilder who I discovered had no issues with mortgage fraud. I escaped the relationship before anything legally tied my mortgage company or me with them, but the damage to my company and, more importantly, to my spirit was too much.

I shuttered the mortgage company.

$60 Is Better Than $0

As the day approached to write, produce, and publish the next newsletter, I mulled over a difficult decision. My referral sources knew that I closed my mortgage company, as did my friend. No one expected a newsletter except three people who’d paid me a total of $60.

Would I be willing to keep pressing forward with only three customers paying $20 per month each?

I’d already put my resume together and was job hunting.

I decided that I would continue the newsletter, and I charged the credit cards again the following month. I didn’t have a job, and $60 was $60 after all.

Within a few weeks, I landed a crappy job, so the decision to keep the newsletter going was relatively easy, plus my monthly run rate had doubled. I committed to the hiring manager at the crappy job that I would stay for six months.

They were the most miserable six months of my professional career.

During that time, I raised the price of the newsletter and grew my monthly run rate to well over $2,000 per month. It was awesome, but not enough.

I landed another job, and I loved it.

I considered closing down the newsletter company, but that side hustle had turned into a side addiction. It was fun growing this little company. I enjoyed producing the newsletter, and it felt good to have this little emergency fallback.

You Never Know Unless You Leap

A few months into the new job, I realized that the CEO and I were not on the same page. Strategic and tactical misalignment was what I told myself as my good job became more and more frustrating. I tried my best to make the most of the situation, but nothing was going to get any better.

My newsletter company continued to grow, and then one day, its revenues passed my salary. The direction I needed to go became clear. I wanted to keep pursuing my little dream. So, I wrote that resignation letter.

I never looked back.

Twenty+ years later, I still write that weekly newsletter, but the mortgage industry has radically changed. Someday, I’ll close it down and end that chapter of my entrepreneurial journey. It’s been an amazing experience and taught me many lessons.

As I work with people starting their own businesses or changing their lives, I always keep in mind the feeling that I had when heard the words “that little newsletter thing.”

Many people have shared their “little dreams” with me. Whether it’s a desire to start a business or become a freelancer, a writer, or a digital nomad, I never underestimate the value of a little dream.

For me, my little business from my little idea enabled me to be a stay-at-home dad and build irreplaceable relationships with my sons. When my sister got cancer, I was able to take turns with our mom sleeping in the hospital. I hike and climb mountains during the week when others suffocate in their cubicles. I get to do so many little things that I can’t keep track of them all.

And of course, that little dream put well over a million dollars in my pocket.


Originally published on, in the publication, The Bigger Picture.