The Billion Dollar Lifestyle Business Paradox

For many budding entrepreneurs, the idea of starting a “lifestyle business” is highly attractive. Earning a few thousand—or even just a few hundred—extra dollars a month can be life-changing. And of course, that allure is real — it definitely was for me, as I chose to escape the corporate grind.

But there are some deeper, contradictory psychological implications of pursuing a lifestyle business that are worth unpacking.

I want to talk about a few things in my psychological journey of building businesses. But the crux of it is reflecting on the questions: When and under what conditions is ok to aspire for modesty, or wealth?

The Trade-Offs of Aspiring for “Just Enough”

When I started building my first business that took off—Disco Media—I had similar aspirations. I wasn’t aiming for world domination or a billion-dollar valuation. Instead, I wanted freedom from the constraints of the traditional workforce.

At the time, I had seen the trade-offs required to build large, scalable companies like those in Silicon Valley, where I had previously worked (last at Lyft). Scaling would have meant raising money, hiring employees, managing offices, and participating in endless meetings. It often meant sacrificing personal freedom for the sake of growth.

I wanted none of that. My framework became simple: grow as much as I reasonably could without being hamstrung by employees, physical offices, or heavy managerial burdens.

Covering the Basics

When I launched Disco Media, my initial goal was modest, and almost fantastical: pay for travel. And, if you travel on a budget, that’s easily achievable. For as little as $100 a day, you can enjoy comfortable accommodations (even on Airbnb), decent food, and cover transport between countries.

We hit that target relatively quickly (though not as quickly as I had hoped). But as the business grew, so did my ambitions.

I started to see the potential of our model—writing SEO-optimized content. It was rewarding, not just financially, but personally. I loved writing, and the feedback from our readers was deeply fulfilling. At its height, Disco Media had over 10,000 unique daily visitors, many of whom left comments or wrote to express their appreciation.

For me, this was the pinnacle of a lifestyle business. It wasn’t just funding my life; it was my life. I was writing about what I loved—language learning, motorcycles, and other passions.

When Empires Crumble

But even the best-laid plans hit snags. In recent years, significant changes in the online world have disrupted businesses like mine.

The biggest game-changer? AI.

Suddenly, my competition wasn’t just other writers—it was armies of bots churning out endless content. Whether high-quality or not, these bots siphoned traffic from my site, making it harder to maintain our audience.

It was so much that I eventually threw in the towel. “If you can’t beat ’em,” I reasones, “join ’em”. That’s why these days I hardly write, and am spending most of my time building AI-powered software.

The second challenge was more existential: the paradox of modest aspirations. By aiming for “just enough,” you often achieve… exactly that. While it’s fine to aim for stability, small ambitions rarely grow into something extraordinary.

The 10x Rule

This reminds me of a principle I heard early in my entrepreneurial journey: the 10x rule. It was in one of those self-help books that spends too long explaining the same concept. Luckily, I didn’t read it!

The idea is this: If you have a goal, magnify it 10 times. Don’t aim for 10K/month — aim for 100K. Worst case, you’ll land somewhere in between. Best case, you’ll start approaching that goal and can continue to magnify it further. The idea is that by thinking bigger, you don’t hamstring yourself psychologically into not achieving it.

There is a lot of research on the effect of goals on the mind. People often talk about how racers tend to slow down when they see the finish line, for example. Professional racers train this tendency out of themselves as early as possible by aiming for beyond the finish — setting a larger goal than the one they actually have.

However, the approach of magnifying goals comes with its own set of problems. Trying to 10x everything—or build billion-dollar businesses—can take the fun out of your work.

For instance, I love writing about motorcycles and language learning. But these topics can realistically only generate $5,000–$10,000 a month without significant investment. Even if I scaled to a small media empire making $50,000–$100,000 monthly, I’d face constant competition and the overhead of managing writers and editors.

So, I have to make a tradeoff in choosing what I focus on, not just how.

The problem is that as I face the complexities of growing a business, or when I’m hit with challenges, I start to 0.1x my previous 10x. “I wanted 100k,” I’d think, “but really, all I need is 10K.” This a hint of the psychological challenges underneath.

False Modesty

I’ve often wondered whether we opt for lifestyle businesses because of limitations we’re afraid to admit to ourselves. Do we do it because we don’t believe we’re capable of achieving something greater? Or that we don’t deserve something more?

There’s nothing inherently wrong with aiming for a modest, happy life. But it’s crucial to recognize whether you’re choosing that path out of contentment or because you’re afraid of striving for more.

I grew up with a skepticism of wealth. Many people with religious backgrounds do — wealth and virtue don’t go hand in hand. To this day, I question whether there can be a truly “good” billionaire. I struggle to imagine what I’d do (for myself) with more than around $50M (which is a lot, I know; but many have much more.)

But this has been confused with societal pressure to not talk about aspiring for greatness. In Australian culture there’s a strong sense of tall poppy syndrome — it’s much less accepted in Australia to outwardly say things like “I want to be the best in the world” or “I’m going to be a billionaire”. People cut you down constantly. In places like America — especially the big cities — it’s easy to find supporters. But not so in Australia.

This is despite the fact that I see virtually hanging on my wall a sign that says:

It’s honestly what I see. Some people may find it alienating, and that’s fine. Others may say “Why ‘future’? Why not imagine it being right now?” The answer to that is simply that to me it’s the same thing — the only thing differentiating me from future me is the passage of time.

So here’s the heart of the paradox: If you aspire to modesty, you’re likely to achieve modest results through self-imposed constraints. This is ok. But don’t do it out of a falsely socially imposed sense of modesty; it’s ok to aspire for greatness.

The Takeaway

Great wealth doesn’t necessarily equate to happiness, nor is it a guarantee of doing good in the world. But it’s okay to aspire for greatness if your foundation is sound.

Similarly, it’s perfectly fine to choose modesty—if it comes from a place of self-satisfaction and belief in your abilities. What’s not okay is letting fear, self-doubt, or societal judgments about ambition hold you back from what you’re truly capable of.

The real challenge is deciding whether you want to build a life of simplicity or reach for the stars—and being honest about why.