I've Made More Money Flipping Websites Than Houses

I have a confession: I used to think “real investing” required steel-toed boots, a truck that smells like drywall dust, and at least one emotional support Home Depot run per day. And for over a decade, I lived that life.

I flipped houses. I’ve negotiated with contractors, dealt with costly renovations, had real estate agents act slimy, and of course, dealt with a few bad tenants who caused property damage.

But at the same time, I also flipped websites. In my experience, one outperforms the other, for MANY reasons.

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After doing both for more than ten years… I’ve made more money flipping websites than houses. Not because traditional real estate investing is “bad,” by any means. Not because digital is “easy,” either.

But because digital real estate is a different game with different rules and, for me, way better odds. Watch my video to learn why:

Why I Chose Digital Real Estate Over Houses (After Doing Both)

Picture this: it’s 7:12 AM, five years ago.

I’m wearing jeans I can’t sit down in because they’re full of invisible drywall needles. My phone is buzzing like a trapped wasp.

Contractor: “We opened the wall.”

Me: “Okay…”

Contractor: “It’s… wet.”

There are few words in the English language that can ruin your breakfast faster than “It’s… wet.”

It’s the real estate version of your pilot turning around mid-flight and saying, “So, small vibe shift up here.”

Suddenly, dealing with a surprise ecosystem. And that’s the thing about traditional real estate: the highs are high, but the surprises are… moist.

Now fast forward to today.

It’s 9:46 PM. I’m in sweatpants. No boots. No dust. No one has texted me a photo of mold like it’s a new baby announcement.

I’m relaxed and cozy on the couch as I open my laptop and check a website I bought. Traffic’s up. Revenue’s up. Costs are predictable. No one has “opened a wall” and discovered a swamp.

And when something does go wrong, it’s usually fixable without calling three people and sacrificing your margins to the Renovation Gods.

laptop comunter under the words made more money in digital real estate

Digital Real Estate Vs the Housing Market

Here’s the honest comparison, from someone who’s been in both trenches.

1) The “Surprise Factor” Is Lower with Digital.

House flips come with hidden issues: plumbing nightmares, electrical “creative choices,” foundation cracks that appear the second you close. With websites, you can usually spot problems early:

traffic sources
revenue streams
expenses
SEO trends
content quality conversion rates
You can do due diligence without ripping out a bathtub.

2) Scalability Isn’t a Wrestling Match.

Houses are heavy. Both figuratively and, physically. Each one is a whole project with its own timeline, permits, labor, and chaos. On the other hand, websites scale like this:

Optimize pages > improve conversion > add content > diversify traffic > expand products/affiliates > increase RPM and sales.

Same “property,” better performance. Without needing a dumpster in your driveway.

3) Lower Capital Requirements (Usually)

Real estate often demands bigger chunks of cash, financing, holding costs, and a tolerance for “carrying” a property while it happily eats your budget.

With websites, you can start smaller, reinvest profits, and build a portfolio faster, especially if you’re good at improving operations.

4) Time-to-Resale Can Be Faster

A house flip can take months and one delayed inspection to turn your calendar into a tragedy. A website flip can start improving in weeks.

There are many small changes you can make yourself, without needing any permits or contractors for. Overall its less waiting. More testing.

5) Geographic Freedom Is Real

Houses tie you to a location, market shifts, local contractors, and sometimes the emotional trauma of driving past your flip every day like, “Why are you still like this.”

Websites, however, give you a global audience and global buyers. This allows you to actually work from anywhere.

6) Exit Options Are Cleaner

Selling a house has a whole ecosystem of friction: agents, showings, inspections, appraisals, financing surprises, closing delays. Selling a website is often more straightforward: list it, negotiate, transfer assets, cash out.

Still work, yes. But fewer people peering into your “foundation.”

7) Your Upside Is Often More Under Your Control

This is one of the biggest reasons for me! With houses, appreciation is partly market-driven. You can renovate perfectly and still get hit by rate hikes, inventory spikes, or neighborhood shifts.

With websites, you can influence value by doing things like growing the traffic, adding new products, diversifying the monetization, and creating a stronger brand.

In other words, you can build multiple, not just hope for it.

The Real Reason This Worked for Me

Here’s the quiet part I didn’t understand early on: House flipping is often a battle against variables you can’t control. Website flipping is a game of leverage.

I’m talking:

Leverage of content.
Systems.
Distribution.
Compounding improvements.
Audience trust.
Search intent.
Email lists.
Offers.

A good website can keep paying you while you’re asleep. A house can also do that… but it usually requires tenants, property management, repairs, vacancy risk, and the occasional text that starts with, “So… the toilet has ruptured.”

Digital income isn’t 100% “passive.” But it can be lighter. Cleaner. Faster to iterate. And for me, it’s been more profitable.

“Okay, But Isn’t Website Flipping Risky Too?”

Yes. Anything that makes money involves risk. Websites can lose traffic. Algorithms change. Monetization can dry up. You can buy a lemon.

But the difference is: most digital problems are visible in the data and fixable with strategy.

You don’t usually discover a foundational crack in a website that costs $18,000 and three weeks of therapy.

The Takeaway: Digital Real Estate Is a Different Kind of Wealth Builder

If you’re debating between traditional real estate and digital, here’s the thing to consider: House flipping is a construction project. Website flipping is a business optimization project.

One isn’t morally superior. But one fits certain personalities better.

If you like systems, marketing, leverage, and compounding growth, digital real estate can be an absurdly powerful lane.

Now, if you want the full story (including the mistakes, the wins, and the exact reasons I made the switch), I break it down in my video (top of this page) with real numbers, real examples, and zero pretending I had it all figured out from day one.

👉 Scroll back up and watch my video on “I’ve Made More Money Flipping Websites Than Houses.” It’ll either confirm what you’ve been feeling… or save you from your next “It’s… wet” moment.