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3 lessons learned from my first three years in business

Today’s my three-year anniversary of starting my business — again, at the time of writing, not necessarily at the time you’re reading. I got you trapped in my autoresponder, cully, slowly feeding your addiction each day. Muahahahaha.


I remember my first day not working for anyone like it was yesterday. Before I started my business, I worked remotely for a popular graphic design company on the marketing team. Even though I worked remotely, I frequently worked 10, 11, or 12 hour days.

Nothing gives me more joy than thinking about how Friday, October 4th 2019 was my last day at said company. I spent that weekend doing some work, but the real shock hit me when I sat down at my computer the following Monday.

I had no Slack channels to open. Nobody to respond to. Nothing I “had” to work on (besides, yanno, finding my first client because I quit my job before landing my first client). I could do anything I want. The freedom I felt, as corny as it may sound, must be similar to the freedom the Founding Fathers yearned for.

I can still smell the fresh, autumn air from this time. In fact, every time autumn comes around, my brain sends me on a journey to my first days as a business owner, with nobody to work for but my damn self.

I can still picture the backlash I got from my family when I told them I was quitting my cushy job for mayhap the riskiest decision I ever did make in my life (and I decided to drop out of college years before I graduated).

I remember the “back against the wall” feeling I had that I had no plan B if’n my business idea didn’t pan out. And, yes, of course I remember doubling my income within my first 3 months of starting my business.

But it wasn’t all unicorns and rainbows:

My first ever sales call happened around this time with a JACKED keto influencer. I embarrassed myself so badly on said sales call, that he offered me unsolicited advice. I used his advice, and landed my first client (who I still work with to this day) a few weeks later.

I remember the high I got after closing my first sales call. How hope coursed through my veins. And how it hit me that I may never have to work another job again.

I hope you get to experience this feeling if you’re thinking about starting a business.

Anywho, I could keep rambling on about my first few days as a brand-new business owner. But I won’t. Instead, I’ll do the corny thing and give you three lessons I’ve learned from my first three years of running my business.

While these lessons apply specifically to my freelance copywriting business, they will help your business too — no matter what you sell.

Enough buildup, let’s dive in:

Lesson #1 — Never stop generating leads

As I said, within my first three months of starting my business, I doubled my salary from my job. Within my first 6 months, I was making good money. Real good.

But then I made a massive mistake which tanked my income:

As I started getting more and more clients, I spent less and less time on generating leads. Back when I started, I had no fancy software, systems, or help with generating leads.

My process included spending hours searching through every Google and Amazon search result for my niche. Then, making 10 accounts to poach mfs emails. Then, loading them up into Streak—a free cold email software which integrated directly into Gmail—and sending them my cold emails.

None of this was automated. I spent 10-20 (or more) hours per week doing this. And as soon as I got busy, I stopped, which resulted in an empty pipeline a few months later.

Which leads me into my next lesson:

Lesson #2 — Who, Not How

Dan Sullivan teaches this. And it’s powerful advice for every single business that ever did exist.

The basic point of Who, Not How is this:

When you have a business problem, obstacle, or opportunity, you should ask yourself who can solve it, not how you can solve it. This is how you go from an enslaved business owner who works for a psychopath (i.e. you) to a business owner who has the freedom to take entire weeks or months off without your business skipping a beat.

When it came to lead gen, this first meant buying lists from Fiverr instead of Googling and Amazoning until my hands bled. Then, it meant buying a software like Mailshake that could automate my cold outreach instead of relying on Streak, which was free but more expensive than Mailshake because of the time it required of me.

This alone saved me at least 10+ hours of work per week.

Fast-forward some years, and then this evolved into outsourcing my lead gen to an agency. (If you’d like a referral, let me know. They ain’t cheap, but they are good and worth every penny.)

Now, I don’t have to set up or keep track of my cold email outreach. I don’t have to reply to replies from my cold emails. Nor do I have to buy lists (or even pay for my cold email software).

Who, not how.

In the coming months, I’ll be launching another new strategy to land clients. And I’m working on systems which will allow me to handle a much bigger client load (without sacrificing my results).

Lesson #3 — Creating no-brainer offers

This is my recent change to my business model. When I first started, I’d do any kind of copy work for any kind of client.

I wrote emails, blogs, product descriptions, fake reviews (as I told you yesterday, which I’m still not proud of), landing pages, the list goes on.

I served all sorts of different clients — from coaches to ecom to biz opp and more.

And, I didn’t have a solid offer. Sure, I could land clients who desperately needed help, but I had a bigger client list than I do today and made less money.


I didn’t have good offers.

This year, I changed my offers. I made it easier to scale up with me and scale down with me. Not only does this mean more moolah in my pockets, but it also means better results for my clients too. I either had to fire my cheapest clients, or transform them into my highest paying clients.

It’s still a work in progress, yes. But methinks had I spent more time creating no-brainer offers, I would’ve skyrocketed my income much quicker than I have.

And here’s a bonus lesson for reading this far:

Lesson #4 — Have fun with it and practice your freedom as much as possible

When I first started, I worked chaotic hours. I spent at least 10 hours each day during the week on my business. Then I worked at least 4—and more like 8—hours each and every weekend.

I did nothing “fun” when I started my business.

The only two things I did was work on my computer and hit the gym.

But this wasn’t sustainable.

As I grew, and practiced lesson #2 (who, not how), I realized I had much more freedom than the average person. So I took advantage of said freedom as often as I could.

Peanut and I started dating in 2020, and we have traveled the world since.

We’ve been to Florida, Chicago, Denver, Mexico, Michigan, Myrtle Beach, Austin, Vegas, and more places I’m forgetting. I worked on some of these vacations, and I didn’t work on others.

Sometime this year, I had a weird realization:

Every time I traveled somewhere, I came back to a bigger business.

And I didn’t just practice freedom by traveling more, I also practiced freedom in an ordinary day:

I quit working whenever I want. If I’m not feeling creative anymore, I’ll hang up my keyboard, and give my brain a break. (This is easier said than done.)

When Peanut and I went to Austin, I worked a normal workweek with one big, fat exception:

We went out to get lunch, shop, or hang out whenever we wanted.

When I had covid, I slept most of the week because writing copy for 30 minutes required a 2-hour nap.

Speaking of naps, I take naps in the middle of my day if I need to recharge my brain.

I practice freedom as much as I can, and you should too.


Because it’s like a muscle:

The more you flex it, the easier it gets.

And freedom, at the end of the day, is the sole reason any entrepreneur starts a business.

Yes, we want to make money. Yes, we want growth. Yes, we want to leave a legacy.

But we also crave freedom. Too many business owners enslave themselves in their business, and create a dream (er, nightmare) life they despise.

Not me.

And not you, if you heed my advice.

Three years ago, I would’ve predicted that I would still be in business today. But it’s nice knowing I am, three years later. I only have a lifetime to go.

Anyway, I’ve rambled enough:

If you wanna experience the sweet, savory zest of freedom while experiencing 2X, 10X, or mayhap 2,348.44X growth in your business with email…

But I must warn you:

You must have a proven offer, an email list, and a desire to take advantage of the freedom your business created for you.


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