10 Years In Business

In February 2016, I handed my boss a printed two-week notice. I was 23 with no degree or clear throughline in my career. Money was tight. I didn’t have the next job lined up. All I had was an internal sense that it was time to move on. 

I tightened my resume and finished those last few weeks. As my last paycheck landed and dwindled, I applied to jobs around Austin. I wasn’t sure what I was applying for. Sales. Journalism. Live events. I interviewed at a few places but nothing stuck. 

One evening, I invited my friend Aaron to dinner. 

Aaron was an entrepreneur multiple times over and was a mentor to multiple friends. I told him about the various roles I’d applied for. I was a young man looking for a vocation and higher-paying work. Aaron listened closely.

When I’d exhausted my ideas, Aaron spoke up and suggested just one. “Alex, you live in a tech city, and you’re a good writer. Why don’t you just write for all these tech companies?”

I don’t remember how I responded. But I thought about Aaron’s suggestion the rest of the evening. The next day, I bought a few books on freelance writing. By the beginning of March, I texted friends to break the big news. 

I was open for business. 

Milestone

Wow. Wild to think I’ve been telling that same origin story for ten years. 

Starting this business has been one of the most fulfilling adventures of my life. I feel so lucky. 

I’ve had the pleasure of working with dozens of great clients. This business has allowed me to travel, learn about myself, build wealth, and gain skills I’ll leverage my whole career. 

So, how do you celebrate 10 years in business? 

One way is to launch a book. My forthcoming book, Executive-Led Marketing, will be available for pre-order in the next few weeks. More soon.

Another way to celebrate 10 years is with an article containing lessons learned along the way. I tried to ignore the obvious ideas or platitudes. I also attempted to offer ideas that are applicable across many small businesses, not just writerly ones like mine.

Here’s what 10 years taught me.

You find shortcuts by doing the work

In the early days of my business, I read every article I could find on freelancing and entrepreneurship. The problem with most free advice on the web is that it’s heavily biased toward hacks. Shortcuts are easy to sell. 

What I’ve learned is that shortcuts in business are real. But they’re seldom the sort of shortcuts you read about in how-to articles. The best shortcuts are on the other side of hard work, extending your time horizons for success, and ongoing experimentation. 

In other words, shortcuts are indeed effective, and they’re everywhere. But the best ones are so specific to your business that they don’t translate into advice you can pass to others. 

My first successful marketing tactic was posting about my services on Craigslist. I suspect this only worked because no one told me to do it. I exploited a temporary marketplace inefficiency. More people were looking for writers on Craigslist in 2016 than writers were promoting themselves on the platform. 

Through free Craigslist postings, I found my first Forbes ghostwriting client, my first journalism project, and was introduced to multiple copywriting clients with whom I worked for years. 

Or how about this one: For two years, my main source of leads was algorithm favoritism on Upwork. People would search “SaaS copywriter” on Upwork, find my profile, and then Google my name and reach out directly through my website. 

Most recently, the SEO and publicity work I’ve done for years in my business is now paying off in the form of GEO referrals from Claude, Gemini, and ChatGPT. I never wrote an article with the intent of showing up in AI, so selling this as a hack seems ridiculous. Yet it’s worked for me.

You find shortcuts by doing the work. 

The secret to longevity is financial resiliency

I started Lewis Commercial Writing a year before Sarabeth and I got married. A week before our wedding, Sarabeth quit her job to join me in the business. We’ve both been self-employed for most of our time together. (Today, Sarabeth runs an interior design firm in Austin called Young Southern.) 

If you want to win the long game in business, you must master the basics of personal finance. Working a 9-5 job, you have the luxury of a consistent paycheck, easy taxes, and employer-initiated retirement savings. It’s easy for a bank to issue you a mortgage. 

The self-employed person experiences the opposite. Your paycheck varies considerably from month to month. You must have the discipline to withhold and pay your own taxes. You are responsible for your own retirement contributions.

Fortunately, the best practices of finance can be distilled down to a simple sentence: Live on less than you make, save for a rainy day, invest in long-term assets, and avoid bad debt. 

It’s dangerous trying to outearn bad financial habits when you’re self-employed. You give yourself a massive business advantage by simply saving and investing. I’ll go so far as to say it’s a requirement for being self-employed over the long haul. 

What do I mean when I say invest? 

I am not talking about reinvesting in your own business. Reinvestment can be good but that’s not what I’m talking about here. You must take profits!

The top 1% of earners in the U.S. are entrepreneurs. But most of them don’t look like Mark Zuckerberg or Elon Musk. Tech conglomerates and startups are still statistical outliers in the world of personal finance.

No, the majority of high-earning entrepreneurs run “pass-through” companies. Your business makes a dollar, and that dollar (after taxes and business expenses) is passed straight through to the owner's pocket in the form of distributions. 

It’s the simplest business structure, most commonly used by service providers such as consultants, lawncare companies, independent lawyers, physicians, and creatives. 

What’s my point? The typical online advice to entrepreneurs is to keep reinvesting your profits into your business. This is good if you have obvious ways to grow (like hiring talent or paying for tools that meaningfully increase your earnings). But I also think the reinvestment advice for this class (high-earning, skills- and services-based) is overstated. 

The power of most pass-through businesses is high margins and earnings. The downside is that all your risk is centralized in your personal talent or salesmanship.

As soon as you’re done with the business, your income dries up with nothing else to show for it. 

The best way to turn your high income into real financial freedom is to invest your high profits into real assets that are uncorrelated to your daily work. 

My suggestion (not investment advice): index funds or real estate. 

For me, I think of my business as the cash generator that enables me to buy assets. Those assets grow as I sleep, slowly making my need for high earnings irrelevant over time.

A good income is leverage. A high income that contributes to assets is freedom.

Marketing works in the short term. Reputation is better. 

I recently caught up with a fellow ghostwriter. He’s been in business a few years and is still learning how to promote his services. 

I told him that I see two distinct camps of ghostwriters. The first are the overtly salesy ones. They have websites devoted to ghostwriting. It’s in their bio. They actively promote their writing services on social media, landing pages, and blogs.

The second are just writers publishing great work. These are everyday authors, journalists, and bloggers. You won’t find their ghostwriting services page because they don’t have one. When they’re hired, it’s done on back channels and less formally. 

Someone DMs them on X and says, “I liked your last article. Could you do that for me?” It’s the natural outcome of being someone’s favorite writer. 

What’s worked best for me over the years is finding the middle ground. I make my services clear through regular marketing. But I remind myself that the best clients aren’t hiring me because they need words on a page. They want to tell good stories and share cogent ideas.

They hire me for how I think. Or because my voice resonated with theirs.

In the short term, marketing will help you earn business. Over the long term, what matters more is your reputation. 

Do good work and deliver it on time. Be a pleasure to work with. If you get those things right, you’ll rise over time to the top of any industry.

Maybe Arnold Schwarzenegger (quoting Ted Turner) said it best, “Early to bed, early to rise, work like hell, and advertise.” 

Thanks for walking with me on this 10-year (so far!) journey. I’m excited for what’s next.