Life before Tech Pro & MSP Sites
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Hi friend —

Before Tech Pro… before MSP Sites… before I figured out how to build a real business…

I was just a regular kid growing up in Newton, Massachusetts. A suburb outside of Boston, with good public schools, snow days, and Yankees Suck bumper stickers everywhere.

I was the third kid, and played my role exactly how you’d expect a third kid to play it.

I didn’t push too hard. Didn’t slack off either. I was a straight B student, mostly because B’s kept me off the radar.

Not a screw-up. Not a genius. Just quietly following the crowd.

And that pattern stuck.

I didn’t ask myself what I wanted to do. I just looked around and did what everyone else was doing.

So I went to UMass.

And because picking something I actually cared about didn’t feel like an option, I chose the safest major I could find: Accounting.

Let me pause here and say that as a business owner, I actually like accounting now.

But not when I was 21 and facing a future of corporate audits, windowless offices, and being on the road for 3 weeks out of every month.

Still, I stayed on the path. Because that’s what everyone did.

So I graduated. Got a job in a mid-sized firm. Bought a business casual wardrobe. Rode the T downtown.

And hated it.

And one day I noticed something:

The people around me actually cared about what they were doing.

My coworkers were into it. Like, genuinely into it. They were studying Sarbanex-Oxley and making plans to become a CFO one day.

Meanwhile I was still playing B-student — except now, my manager noticed too.

I got written up.

And one month later, I quit.

No backup plan. Just a voice in my head that said this isn’t it.

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That was the start of what I’d later describe — only half-jokingly — as my wild oats decade.

I spent almost 10 years doing everything but what I was “supposed” to do.

I traveled.

Taught English abroad.

Lived overseas.

Got a master’s in English.

Tried to get my footing.

(Pictured above: me, sowing my wild oats, with some friends)

And then, towards the end of that decade, something changed.

A friend of mine — Simon — came to visit.

Unlike me, Simon had never had a job. Not once.

Everything he did was entrepreneurial.

And that day, in between catching up, he kept glancing at his phone.

Every time he looked, he had made more money.

He explained it was from affiliate commissions — basically, earning a cut every time someone clicks your link and buys a product you recommended online.

Simon had built simple websites that reviewed software and other tools.

People found those sites through Google, read the articles, clicked the links… and he got paid.

That day alone, he made over $1,000 in passive income — just from people reading something he had written days or even years before.

He showed me how it worked. And suddenly the lightbulb turned on.

There’s a way to make a living without doing what everyone else is doing.

It was the first time I saw a different path. And it stuck with me.

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After finishing my degree, I came back to the States and took a job running a small English school. It was a real business — small team, real P&L — and I felt something I hadn’t felt before: ownership.

I eventually bought into the business.

And a few years later, we got the lucky chance to sell it.

After that, I tried following Simon’s lead and going full-time into affiliate marketing.

It was working… kind of.

I was making some money (writing articles about photo recovery software of all things), but not enough to really live off.

So I supplemented my income by helping businesses with their online marketing.

I found my first client on a website called oDesk (now UpWork) — a hypnotist in Australia who needed help getting “quit smoking” clients.

She paid me $500/month, and I was thrilled.

That was the moment I realized:

Helping small businesses succeed could be a business.

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And then, like clockwork, I saw an ad for something called the 10K Bootcamp, run by my now long-time mentor Brent Weaver.

It was a mentorship program for online marketing agency owners, designed to help you land better clients, raise your rates, and finally build a business that could support your life.

At the time, I was juggling affiliate income, Upwork gigs, and crossing my fingers every month that I’d make rent.

I didn’t know it then, but signing up for that program would be the turning point.

Brent taught me what he calls “building a business with intention.”

And for the first time, I truly took ownership.

Looking back, I learned more in those ten weeks than I did in four years of college.

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I’ll stop here for now.

Next time, I’ll tell you about:
→ How I took my Upwork side hustle and built it into an actual business
→ What led me to MSPs
→ And the $32,000 website project that completely changed how I thought about results and ROI

(That story starts with a client asking me a single question — and me realizing I was focused on the wrong thing entirely…)

Much more soon.

– Nate

P.S. It means a lot to have you reading this. If anything in my story resonates with you, reply and say hey — I’d love to know who’s on the other side of the screen.

Nate Freedman
CEO, Tech Pro Marketing
Founder, MSP Sites

Tech Pro Marketing, LLC, 11 NW Psge, Barrington, RI 02806