By Roger Goodwin | Into Property Investing

When Daniel Latto bought his first property in 1996 at just 26 years old, he had a clear vision: build enough rental income to escape the 9-to-5 grind and never have to answer to a boss again.

Fast forward nearly three decades, and Daniel has done something most property investors would consider unthinkable he's systematically sold off his UK property portfolio and pivoted almost entirely to digital assets.

But here's the twist: he's not anti property. He's just brutally honest about what property ownership really demands, and whether those demands align with the life you actually want to live.

I recently sat down with Daniel on the Into Property Investing podcast, and his journey from IT specialist to property mogul to digital entrepreneur offers some uncomfortable truths every property investor needs to hear.

The Golden Years: Building a Property Empire

Daniel's property journey started with significant advantages. Working at Dell in the late 90s, he was earning £100,000 a year serious money even today, let alone 25 years ago. That income fueled rapid portfolio growth from 1996 to 2000.

"I always hated working for somebody else," Daniel told me. "And now I've got the worst boss ever because it's me. But I've always hated having another boss."

Property seemed like the perfect vehicle for freedom. And for a while, it was.

Reading Rich Dad Poor Dad reinforced what Daniel already believed: assets that put money in your pocket are the key to financial independence. Property offered both capital growth and rental income the best of both worlds.

By the early 2000s, Daniel had built enough passive income to quit his job, backpack around Europe for a month, and return to… disaster.

The Wake-Up Call: When "Passive" Income Isn't Passive

"When I came back, half of my property portfolio was empty," Daniel recalled. "And I'm like, dude, what's going on? And they just didn't care."

This is the moment most property investors face but rarely talk about: the realisation that your "passive" income stream requires constant active management or trusting someone else who may not care as much as you do.

Daniel's solution? Start a lettings agency.

Using his IT background and web design skills (remember Dreamweaver?), he created a one-page website and began managing his own properties. Then he took on other landlords' properties, learning on the job.

The business exploded. At its peak, the lettings agency was getting 25,000 website visitors per month nearly 1,000 people a day. They dominated the front page of Google for high-value keywords like "Aspect 14" (a Leeds development popular with international students) and "short-term lets Leeds."

They doubled revenue every year. They expanded into furniture packages, snagging services, and property management across multiple cities. They hit around £1 million in revenue.

Then 2008 happened.

"The property crash came. The rug was pulled. Our revenues just dropped,"

 Daniel said. They sold the lettings agency in 2011.

The Spanish Experiment: When Distance Exposes the Truth

After selling the agency, Daniel moved to Spain. And that's when the cracks in the property investment model at least for his lifestyle became impossible to ignore.

"While I lived in England, it was great," he explained. "A thousand miles away managing properties? We don't have a lettings agency anymore. So it was actually more like kryptonite and holding me back."

Here's what Daniel realized about property from 1,000 miles away:

The Good:

●       Capital growth

●       Rental income

●       Tangible assets

The Bad:

●       Tenants calling at midnight because they're locked out (drunk, lost keys)

●       Dog poo smeared on walls when tenants leave

●       Tenants not paying

●       Tenants not leaving

●       Washing machines, boilers, and endless maintenance

●       Dealing with councils, solicitors, and tradesmen

●       Lettings agencies that charge double to tell you what the tenant already told them

"What happens with a lettings agency?" Daniel asked rhetorically. "The tenant phones the lettings agency. They say, let me phone the landlord. They then phone me to tell me that the boiler's broken and charge me double the cost than if a tenant just phoned me. So what's the point in that?"

The Digital Pivot: Assets Without the Headaches

While reducing his property holdings, Daniel started building digital assets online courses, lead magnets, marketing funnels, and information products.

One product in particular changed his perspective forever:

A £27 property sourcing course that has sold one copy every single day for the last five years.

Let that sink in. That's over 1,800 sales. Around £48,600 in revenue from one digital product.

And here's what that digital asset has never done:

❌ Called him at midnight about a broken boiler

❌ Smeared dog poo on walls

❌ Demanded a fridge replacement same-day

❌ Required a lettings agency

❌ Needed insurance, safety certificates, or council approvals

"These digital assets are really cool,"

Daniel said.

 "As we reduced the property and the digital assets increased, it moved us away from having to be on call 24/7 with tenants."

He's now moved from bricks-and-mortar assets to digital assets but the principle remains the same: an asset is something that puts money in your pocket.

The "Sell Shovels" Strategy

Daniel's pivot also reflects a timeless business principle: when there's a gold rush, sell shovels.

During the property boom, his "shovel" was the lettings agency helping other investors manage their properties.

Now, his shovel is helping people create digital content and digital assets themselves through his marketing agency and coaching.

"Now the shovel is helping people create digital content themselves and helping create digital assets themselves," he explained. "So we've moved off bricks and mortar more into the modern age, which is all the digital stuff."

Is Property Dead? Absolutely Not.

Before you panic and list your entire portfolio on Rightmove, let's be clear: Daniel isn't saying property investment is wrong.

He's saying it wasn't right for his specific situation living 1,000 miles away in Spain, at 53 years old, wanting fewer problems and more freedom.

"I'm not saying that property is the wrong thing, it's just not the right thing for me in my situation," Daniel clarified. "Now I'm 53 now, I want less problems, I don't want to speak to people, especially don't want to speak to councils, solicitors, tenants and all the stuff handyman work, tradesmen ripping you off."

If you're UK-based, hands-on, building systems, and genuinely enjoy (or at least tolerate) the operational side of property, it can still be an incredible wealth-building vehicle.

But if you're time-poor, location independent, or simply exhausted by the constant demands, Daniel's story is a wake-up call.

The Uncomfortable Questions Every Property Investor Should Ask

Daniel's journey forces us to confront some hard truths:

1. Are you building a business or a job?

If your property portfolio requires constant firefighting, you've created a job, not passive income.

2. Does your business model serve your lifestyle or trap you?

Daniel's properties were profitable but incompatible with his desired lifestyle in Spain.

3. Are you optimising for growth or freedom?

Sometimes the best business decision is to scale down, not up.

4. What's your exit strategy?

Most property investors never think about this until they're forced to.

5. Could you replicate your income with less operational burden?

Digital products, courses, consulting, and content can generate income without tenants, maintenance, or midnight emergencies.

The Hybrid Model: Best of Both Worlds?

You don't have to choose between property and digital assets. Many successful investors are building hybrid models:

●       Property for capital growth and stable income

●       Digital products for scalable, low-maintenance revenue

●       Content and courses to monetise expertise

●       Coaching and consulting for high-ticket income

Daniel's £27 course proves you don't need to create expensive, complex products. A simple, valuable digital asset can generate consistent income for years with zero ongoing operational burden.

Final Thoughts: Write Your Own Story

"We only get one life," Daniel told me. "And it's like live it. We all have dreams and we all have goals… for some reason we kind of hold back and I don't really understand why we hold back."

His message is clear: don't let your business model trap you in a life you don't want.

Property can be an incredible wealth building tool. But it's not the only tool. And it's certainly not worth sacrificing your health, relationships, or freedom for.

Whether you double down on property, pivot to digital, or build a hybrid model, the key is intentionality.

Design your business around the life you want not the other way around.

As Daniel put it: "Tomorrow doesn't exist. Yesterday doesn't exist. It's literally right now in this moment. And we should be building for a better tomorrow."

Want to hear the full conversation with Daniel Latto?

Listen to the complete podcast episode on Into Property Investing Podcast.

Ready to explore digital income streams alongside your property portfolio? Download our free guide: 5 Digital Assets Every Property Investor Should Build here.