One of the most common questions I get from aspiring internet entrepreneurs is some version of this: should I tell my employer about my side hustle? I addressed this topic back in Episode 17 of the podcast, recorded while literally driving to the airport for a business trip, and the advice holds up well in 2026.
The Core Tension
Here is the situation most part-time entrepreneurs find themselves in. You have a good day job. You like it, maybe even love it. But you also have ambitions to build something on the side. The question is whether telling your employer about your internet business is smart, risky, or somewhere in between.
I have lived this tension myself. I genuinely enjoy my day job. I never want to send the signal that I am disengaged or looking for the exit. At the same time, I have been building internet businesses since 2007 and podcasting since 2009. These are not secrets I could easily hide even if I wanted to.
My Framework for the Decision
There is no universal right answer here, but I have developed a framework that works for most people.
1. Check Your Employment Agreement
Before anything else, read the fine print. Some employment contracts contain non-compete clauses, intellectual property assignments, or moonlighting restrictions. In 2026, these are more common than ever, especially in tech. If your contract explicitly prohibits outside business activities, you need to address that directly, possibly with a lawyer, before proceeding.
2. Assess the Overlap
If your side business competes directly with your employer, that is a problem regardless of what your contract says. Promoting a competing product using knowledge gained from your day job is an ethical and legal minefield. If there is zero overlap, the conversation becomes much simpler.
3. The Need-to-Know Principle
My general advice is this: your employer does not necessarily need to know about your side business, especially if there is no conflict of interest and you are not doing it on company time or with company resources. That said, transparency tends to serve you better in the long run than secrecy.
If your boss discovers your side project through a Google search or a colleague's mention, and you never brought it up, that can create trust issues. Compare that to proactively saying, “I build small websites as a hobby on evenings and weekends. It has nothing to do with what we do here, and it will never affect my performance.” That kind of openness usually goes over well.
4. Never Use Company Resources
This is non-negotiable. Do not use your work laptop, work email, work internet connection, or work hours for your side business. Ever. This is the fastest way to create a legitimate grievance. Keep everything completely separate.
5. Performance Is Your Shield
The best protection for your side hustle is being excellent at your day job. If you are a top performer, most employers will not care what you do on your own time. If your performance slips and your employer knows you are running a business on the side, they will draw a direct line between the two, whether or not it is actually the cause.
The Identity Question
A related question that comes up frequently is whether to use your real name online. A listener named Chris once asked me this exact question. He had a blog where he was writing about building passive income, but he was worried about his employer finding it.
My advice then, and now, is rooted in transparency. It is perfectly acceptable to use a pseudonym online. Plenty of successful creators operate under pen names. The key is to be honest about the fact that you are doing it. On your About page, explain that you use a different name to maintain separation between your professional and personal lives. Most readers will understand and respect that.
What you should never do is fabricate a false identity with the intent to deceive. There is a clear line between privacy and dishonesty. A pseudonym with an honest explanation is privacy. A fake persona with a stock photo and an invented backstory is deception.
Recording from Anywhere: The Freedom of Internet Business
That episode was partly recorded from a car driving to the airport and included a clip I had recorded on the streets of Seoul, South Korea during a work trip. The point I was making then still resonates: one of the most remarkable things about internet business is that you can do it from anywhere. With a laptop and a wifi connection, you can write content, manage affiliate links, handle customer service, and even record a podcast.
In 2026, this is even more true. Remote work tools have matured enormously. The barriers to running a location-independent business have never been lower. If anything, the pandemic era normalized the idea that productive work happens everywhere, not just in an office.
The Cliff Ravenscraft Lesson
That episode also featured part two of my interview with Cliff Ravenscraft, the Podcast Answer Man. Cliff's story is one of the most inspiring in podcasting. He left a successful insurance career to pursue podcasting full-time, eventually building a business that let him help thousands of people launch their own shows.
The relevant lesson from Cliff's story for the employer question is this: Cliff did not quit his insurance job on a whim. He built his podcasting business on the side, methodically, until the income and the calling were both strong enough to justify the leap. He and his wife paid off nearly $100,000 in debt before he made the transition. That is how you do it responsibly.
You do not need to quit your job to be a real entrepreneur. Build at night. Build on weekends. Build during your lunch break if that is what it takes. But do not sacrifice a good career prematurely, and do not burn bridges with an employer who is paying your bills while you build your dream.
Bottom Line
The relationship between your side hustle and your employer does not have to be adversarial. Be ethical. Be transparent when appropriate. Keep your performance high. Use your own resources and your own time. And build something you are proud of, one night at a time.
