How to Get Started in Real Estate Investment in 2026

When we first launched our podcast several years ago, our goal was to share our collective insight with fellow investors, and especially offer wisdom for total beginners. Since then, we’ve told plenty of stories from when we first started out and shared everything from our early wins to the moments we thought we’d have to give up on real estate altogether. We do this because we know it’s useful to hear where other people have been, but having begun our careers pre-Covid (or even, ahem, pre-2008 financial crisis), we appreciate that the landscape of 2026 looks different to when we were whippersnappers. 

That’s why, in honor of new years and fresh starts, we recently took to the studio to ask ourselves this simple question: if we got started in real estate today, how would we do it?

Our conversation revealed a lot about what has changed, but it revealed even more about what hasn’t. In this post, we break down what we would do if we were just starting out today. Read on to find out why we would prioritize our safety nets, how we would go about learning and gaining experience, and why we’ve come to the conclusion that the ability to think years into the future will always matter more than the year you get started.

We Would Set Ourselves Up For Success Financially

When we first started out in real estate, our focus was mainly on strategy and, luckily, things worked out. However, experience has taught us that luck isn’t something you should count on and, although strategy is important, the answer to the question of which one is right for you is secondary to the really important question: “how do I get started in this business without blowing myself up financially?” 

Now, we understand that risk is an inherent part of investing. We also know that the definition of “blowing up” looks different for everyone. Someone who is 20, single, and living at home, for instance, will have a different calculus than someone who is 33 with a spouse, kids, and mortgage. But whatever your safety net and obligations look like, you need to account for them before you do anything else. 

Why? Because if your first deal goes bust you want it to be a learning opportunity, and if you’re still able to keep food on the table and a roof over your head, it will be. On the other hand, if failure means the bank will foreclose on your house and your wife will leave you, you’re probably going to have a very short real estate career no matter how much your mistakes may teach you. 

If we were starting today from scratch, the first thing we would figure out is a contingency plan. Maybe it would be a year’s worth of savings, a side hustle, or a steady job. Then we would think about strategy. 

Speaking of strategy…

We Would Still Start With Wholesaling 

Despite the bad rap wholesaling sometimes gets nowadays, it’s still our go-to beginner strategy. We’ve talked before about its many advantages. It’s fairly low-risk, there’s little barrier to entry, it pays quickly, and, most importantly, it teaches you about deals. 

Wholesaling is a first class, hands-on education in sourcing deals, negotiating deals, and recognizing what is and isn’t a deal. It immerses you in your local market and gets you talking to experienced investors, which helps you learn more about neighborhood values, repair costs, buy boxes, and the important questions you need to ask. It will hone your judgement and give you valuable insight that you can implement with different strategies like flips or long-term holds in the future. 

That said, we would only wholesale locally.

One of the biggest problems in today’s market is out-of-state wholesalers selling deals they don’t understand to buyers who trust bad numbers. Too many people lose $50K on their first deal and walk away from real estate forever because of it.

That’s why we’d make sure to take the kind of steps that both maximize the chances of success and teach you the most. We’d walk the properties, learn the neighborhoods, talk to local investors, and ask where every number was coming from. 

We Wouldn’t Quit Our Jobs Right Away

Well, Adam might.

But in all seriousness, we wouldn’t go from a couple of successful wholesales into full-time investing. The reason why is not that nowadays the market is different and success is harder to come by. Real estate is as powerful a tool for wealth creation as it’s ever been. The real reasons are actually a lot more timeless. They basically boil down to these:

• Rookie mistakes are expensive
  
• Learning curves are real
  
• Stress clouds decision-making
  

As we’ve already said, having a cushion to fall back on is often crucial to early success. Plus, we wouldn’t just think of keeping a W-2 job as a means of staying on firm financial footing. Ideally, we’d use it as an opportunity to work inside the real estate industry. 

We’d work for a property manager, investor-friendly brokerage, in construction or renovations, or alongside a seasoned local investor. That way we’d be able to gain hands-on experience with deals, repairs, tenants, and operations and shorten our learning curves without risking financial ruin. 

We Would Learn Pricing Before Scaling

We’ve learned that one of the most dangerous things a new investor can do is scale before they understand pricing. It’s easy to recover from a missed opportunity, but it’s hard to recover from a bad deal. 

When beginners make bad deals, it’s usually because they’ve rushed in and trusted numbers that they didn’t fully understand. That’s why we’d pump the brakes spend serious time learning things like:

• How to estimate rehab costs
  
  
• The difference between rental rehabs and flip rehabs
  
  
• How location affects value

And so on. 

This isn’t the type of knowledge you can gain just from looking at spreadsheets, and few people have gotten rich by believing things that sound too good to be true. That’s why early on we would say no more than yes and focus on things like walking properties, talking to contractors, comparing estimates, and watching experienced investors evaluate deals.  

That’s not to say we wouldn’t shift our focus to scaling eventually, but before we started to risk too much of our money, we’d make sure we had a good understanding of what seasoned pros are willing to bet on with their money. 

We Wouldn’t Try to Do Everything at Once

Just as it’s important to understand numbers before diving in, it’s important to understand your strategy. Real estate has dozens of strategies, but they only tend to be effective if you focus on learning one at a time.

If we were starting over, we’d pick one path and commit to it until we understood it deeply. We’d learn everything we could about deals from wholesaling before moving on to flipping, then we’d learn everything we could about renovations, budgets, and timelines from flipping. We’d learn about property management from investing in single-family rentals before acquiring multifamily properties. You get the idea. 

There are a million ways to make a million dollars in real estate, but trying to learn all of them at once is a great way to make zero.

We Would Keep Our Long-Term Goals in Mind

We all know that cash flow is essential for a growing business, but we’ve seen many an investor get dazzled by big paychecks and fall into the grind of simply living from one to the next. 

Making a decent living from deal-to-deal income is fine, but there are plenty of 9-5 jobs that can provide the same money (and a lot more security). What sets real estate apart is its potential for wealth creation, and that is a different thing to income entirely. 

Wealth creation isn’t about short-term cash flow. It’s about holding assets that increase in value over time, gaining equity, and maximizing potential. It offers little in terms of instant gratification, but it offers everything when it comes to financial freedom. Experience has taught us that what distinguishes truly great investors from merely good investors is the ability to keep this in mind and think long-term. 

That’s why if we were to start over today, our top priority would be to focus on the big picture. 

Instead of getting hooked on big paydays, we would think of our early deals as stepping stones to building a portfolio that pays for life. Once we’d built up enough capital, we’d focus on acquiring rental properties as long-term holds in order to build wealth. Then we’d use infusions of cash from flips and wholesales for scaling and short-term sustainability. 

The Bottom Line

Real estate has changed a lot since 2018, and it’s changed even more since 2003. The regulations, interest rates, and price points of today are very different to what they were when we were just getting our feet wet. However, the principles of investment haven’t changed at all. 

If we had to start over in 2026 with no capital, connections, or any advantages apart from the wisdom we’ve gained along the way, we’d still have an easier time than when houses cost half what they do now and banks would give anyone a mortgage.

So, if you’re just starting out and you want to make things easy for yourself, do what we would do:

• Keep income while learning
  
• Work inside the industry if possible
  
• Learn how to price deals correctly
  
• Start locally
  
• Use short-term strategies to fund long-term ownership
  
• Stay patient and play the long game
  

If you’re serious about getting started and want help understanding your local market, deal numbers, or next steps, connect with a local Evernest Investor-Friendly Agent. Having someone in your corner who actually knows the terrain can make all the difference.