A brief introduction to buying online businesses

Source: Stencil

There’s a lot of buzz around building an online business. Everyone tells you to start a blog. Launch a newsletter. Sell a course. Learn to code so you can launch the next unicorn SaaS company. Starting a business from scratch seems to be the topic of every other article or course I see online.

But is it overrated? What if, instead of enduring the grind of the first two years of business, you just purchased an already-cash-flowing business from another entrepreneur?

I recently sat down with several entrepreneurs and asked them about what it takes to buy and sell online…


It starts with realizing these things aren’t mutually exclusive.

Source: Stencil

The internet is polarized about how young people should spend the first several years of their careers. There’s one side that insists you should spend your twenties traveling the world, living your dreams, and postponing any big responsibilities and career moves until you’re closer to 30. You’re only young once, after all. Don’t settle down before you have to.

The other side says to put your head down. Find a career. Start investing. Make big professional moves while you’re young so that time and compounding can work their magic. …


Spoiler alert: Freelancing gets better with time.

A watch in front of lights
A watch in front of lights
Source: Stencil

In March 2021, I crossed the five-year mark as a full-time freelance copywriter. In many ways, the career has been about what you’d expect. I’ve endured the scary volatility of living project to project. I know what it’s like to own my calendar and have choice about who I work with. I make a good living — but I have had multiple clients ghost me without payment. I lived as a digital nomad, earning money through my laptop as I explored the world.

And recently, I had to learn the hard way that no one hands you a congratulatory plaque…


How two companies used opposite tactics in branding to achieve wild success

Monster can in grass
Monster can in grass
Source: Stencil

Both women took a turn with the knife.

One at a time they stabbed the side of their Monster can.

Sleeves rolled up on their arms, the women gave one another a nod, popped open their tabs in unison, and the race was on. They put their mouths against the puncture holes, threw their heads back, and chugged.

The winner raised her hands in triumph a moment later.

This was Vans Warped Tour 2015. And no, these staffers weren’t shotgunning energy drinks — they were drinking water.

Appearances Go a Long Way


Make freelancing more secure than a full-time job

Source: Stencil

It’s risky business giving up a 9–5 job to work for yourself as a freelancer. Instead of relying on a biweekly paycheck, you accept a career that ebbs and flows without a predictable pattern. One moment you’re juggling more work than you can handle and the next you’re staring at an empty calendar — and a draining savings account.

I almost gave up freelancing several times in my first year. One month I had to tell my landlord that rent would be late. Another, I had to borrow money from my brother. Multiple times I had to expense essential bills…


Here’s the strategy I’ve settled on so far.

Source: Stencil

I swore I’d never be an active trader.

I’ve invested regularly and aggressively in the stock market since 2018, always under the same strategy: buy index funds that I plan to hold for decades. If someone told me they actively traded and tried to time the market, I’d silently judge them, thinking about all the stats I’ve read about how rare it is to consistently beat the market.

The truth is, I still swear by index fund investing — and it still makes up almost all of my investing portfolio. But lately, I’ve also decided to try something new. …


Four ways people get paid to promote their own books, blogs, and writing businesses

Source: Stencil

Years ago I freelanced as a live event logistics hand, staffing conferences, concerts, and festivals across North America. I formed many good memories during those years. I watched performances from The Cure and Drake respectively from backstage, interviewed filmmakers between showings at a film festival, and got to see world-class motivational speakers in their prime.

One week I helped put on a two-stop business tour in Ontario, Canada. The speaker was Jordan Belfort, the man behind the business memoir that became the movie, The Wolf of Wall Street. The tour took place about a year after his film came out…


Before Charles Schwab Corporation was an established name in the field of personal investing, it was a scrappy startup from San Francisco

Source: Stencil

In the late 1970s, before Charles Schwab Corporation was a household name in investing and banking, founder Charles Schwab was introduced to a well-known syndicated financial columnist named Dan Dorfman.

They shared a corner table at the Four Seasons in New York City, where Schwab explained to Dorfman about his new company. At the time, high broker fees were standard within the industry of stock market investing. But Schwab saw an opportunity to significantly cut costs: His company would eliminate the expensive research and advisory side of investing to provide a discount brokerage firm.

Let customers do their own investing…


Source: Stencil

Five years ago I resigned from my last 9–5 job to become a full-time freelance copywriter and ghostwriter, turning my lifelong love for writing into a creative career.

The first year was rough to say the least. I barely earned the minimum wage, had to take on a couple side hustles to cover bills, and didn’t know the first thing about running a business.

But my knowledge and situation steadily improved. I learned a lot through books, articles, and just the daily trial and error of running a business. Writing became sustainable.

Less than a year after starting the business…


If I had to start a writing side hustle from scratch today — with no writing samples or marketing training — here’s where I’d begin

Source: Stencil

I was only a year out of high school the first time someone asked me to write professionally. A local nonprofit needed a blogger and one of my childhood friends was generous enough to recommend me for the gig.

Months later, a freelance designer saw the work I’d completed for the nonprofit. He asked if I could help him with a few projects as well: a mix of business brochures, website copy, and technical writing. One day I found a writing gig on Craigslist. Friends started referring me to other businesses. …

Alexander Lewis

Freelance SaaS copywriter and ghostwriter. Access weekly tips about the craft and business of writing: lewiscommercialwriting.com/subscribe.

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