Boosting A One-Person Business Beyond 100K/year Annually: My Story

Looking back on ten years of running

I’ll never forget the day I went from employee to one-person business owner.

It was July 3, 2013. It was a shocking start to a 4th of July weekend. My wife and kids were at home prepping the camper for our annual camping trip.

Just before noon, the human resource lady showed up at my desk, instructed me to pack up my belongings, and then escorted me out the door.

It was the last day I’d be showing up to work for a company, I had worked for 17 years up to that point.

Heck of a way to start a vacation (a very loooong vacation, as it turns out).

Today I’m going to show you what I did to push past the $100k mark and tell you what has been more important than the money.

But first, a disclaimer…


If you’re here looking for a fast way to make $100k or more, this is not it.

There are many out there who can show you how to make a lot more, a lot faster than I have.

My story is mainly about a long and windy transition from an employee mindset to a business owner mindset.

Hell, it may not even be about money, to tell you the truth.

100k may not be a lot for some people, but it has been a lot for me and my family. It gives us a better life than most. and on my own terms.

My favorite part of the last 10 years, and the thing I love sharing the most, is the amount of freedom and autonomy I’ve had.

Sure I could be making a lot more than $100k/year. But it is three times what I was making as an employee, and it is enough to maintain a lifestyle that I have control over.

Knowing that no matter how much I make and how I go about making it is 100% on me. I don’t have to worry about a manager or boss who answers to another boss having the final say on my one source of income.

That freedom and responsibility is what I set out to achieve and what I accomplished.

Here’s how…

A Bumpy Road

My journey hasn't been all roses and rainbows.

Between 2015 and 2017, I had to take a few part-time jobs, including a marketing and sales position at a Boat And RV dealership.

It was here that I learned two invaluable lessons: the power of consistent effort and the art of answering objections.

Consistent Effort: The Key to Sustainable Business

One of the best salesmen took me aside one day and said something along these lines;

“You know what separated me from all these young guys? Why it is that I’m making sales in the winter when it’s slow? I pick up the phone and call prospects 50 or more times a day no matter the season. No matter how much I’m making at the time.”

The failure to do this up to this point is one of biggest the reasons I had to take part-time jobs. I wasn’t making enough calls, and I wasn’t making them because I thought I had enough clients.

When I lost two big clients, it wiped out over 50% of my revenue. Had I been consistently marketing myself, making calls, and networking, aka keeping my lead pipeline full, I might not have had to take those jobs.

Mastering the Art of Answering Objections

Before spending time listening in on dozens of sales conversations weekly, and to a lot of Grant Cardone podcasts on my 50-minute commute, I didn’t understand the importance of answering objections.

Here’s an example of a conversion I’d have with a prospective client before I understood this.

For example…

Client: “Yeah, Google Ads doesn’t really work for me and it’s kind of a scam.”

Me: “Oh, ok. Sounds like we’re not a good fit then. Sorry.”


I never even gave myself a chance. Now I knew I needed to push back.

Client: “Yeah, Google Ads doesn’t really work for me, and it’s kind of a scam.”

Me: “What makes you say that?”

Client: “Oh my cousin Billy ran some ads for me. He $5000 and I only had one sale.’

Me: “How long has Billy been running ads?”

Client: “Oh, he’s really good with computers and needed a project for his High School business class.”

Me: “Well, there’s your problem…. etc., etc.” You get the point.”

There are entire courses on this so I won’t go into detail but I gave myself more than a fighting chance and was able to close many more deals.

Eventually, I figured, if these principles can help me selling campers and boats, which I knew very little about, I sure as hell could sell digital marketing I had been geeking out for almost ten years at that point.

And that’s what I did.

A Fresh Start with Renewed Strategies

So I quit the sales gig and began putting my new skills into action.

One of the primary resources I used was UpWork I knew that had a ton of people looking for help.

“…more than 10,000 freelance jobs are posted on Upwork daily, giving you more opportunities to find the right job that matches your skills and goals.”

That kind of volume was enough for me to develop a consistent effort of prospective clients. I applied for 5-10 jobs per day. I did anything I could talk to 2 or more prospects on the phone every.

At first, I wasn’t as picky on types of work either. Even though Google Ads was my jam, I still applied for other projects related to the market, like landing page building, business naming, website creation, and more.

I even leveraged other experiences, skills, and interests I had. I did a few music-and engineering-related projects (I have a degree in drafting and design).

Creating a Constant Pipeline

UpWork was instrumental in bringing in clients and boosting my confidence. This newfound confidence helped me excel in offline prospecting too.

I attended local networking events, joined local networking groups, and the Chamber of Commerce. I even started running ads and doing my own inbound marketing.

Keeping the pipeline full was essential, but to cross the $100k threshold, I needed to focus on long-term and higher-value projects.

Recurring Revenue Rule

Google Ads became the backbone of my business. Unlike smaller, one-off projects, Google Ads campaigns require continuous management, making them long-term and high-value.

Securing long-term, high-value clients who pay me a monthly retainer meant I didn't need to prospect as much, freeing up time for skill development, additional work for current clients, and creating additional revenue streams, like this very blog.

(You’ll be hearing about recurring revenue, and what the OG internet marketers call “Mailbox Money” if you read my stuff so stay tuned). 

The Big Lesson

Over these past ten years, I've learned that success is not solely defined by the amount you earn but also by the amount of freedom and control you gain over your life.

Transitioning from a steady 9-5 job to a one-person business is far from easy, but it's an expedition filled with incredible growth and self-discovery.

Every crap sandwich I had to eat, every part-time job I took, every call I made, and every objection I overcame led me to where I am today, earning three times more than my last 9-5 job and running a successful business that I built from scratch.

And while hitting the $100k/year mark may not be a big deal for some, for me, it signifies much more than a number. It's a symbol of my resilience, determination, and the entrepreneurial spirit that I embraced.

My journey continues, and while I hope that this story of mine inspires you to chase your entrepreneurial dreams, remember that your journey will be uniquely yours, filled with its own challenges and victories.

Change The World

A few years before I became self-employed, I wrote and recorded a song called “Change The World.”

It was a reminder to myself and others that if you don’t like the situation your’re in, it’s up to you to change it.

This tune felt like a great compliment to the story I just told you.

Here’s a updated version of that song.

There you go, want to change your world? Don’t stand by.

Go get ‘em.

As always, thank you for taking the time to read this. I know you’re busy, and I really appreciate it.

Have a good one,


P.S. I have my UpWork playbook available in my Premium Business Builder Toolbox. I’ve had friends and clients of mine have success using these methods in a few other niches besides marketing, like; bookkeeping, graphic design, social media, and engineering. There’s also a bunch of resources if you are looking to learn some skills you could offer on sites like UpWork. Click here to learn more. 

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