How to Start Your 2025 Real Estate Investing Journey on the Right Foot
The real estate investment landscape has changed dramatically over the past decade or so, and to this day is evolving faster than ever. Today there are a ton of ways to get exposure to real estate, presenting exciting new opportunities for both novice and seasoned investors. Whether you’re looking to generate passive income, build wealth, or secure your financial future, this quick guide will provide you with essential steps and insights to kickstart your real estate journey in 2025.
Narrow Down Your Focus, You Can’t (and Shouldn’t) Do it All
Before you start any type of real estate investing it’s important to understand that there are dozens if not hundreds of ways to accomplish this broad goal of being a real estate “investor.” That doesn’t mean you should try all of them, or even more than one for that matter. To accomplish this task, I often encourage people to think through the following list of self-reflecting questions:
Is there a sector of real estate that I am passionate or excited about?
Do I have a competitive advantage in one particular area of real estate?
Am I handy, good with numbers, or already a real estate professional in some way?
How much effort do I want to put in?
How much money do I want to put in?
What experience level do I have?
What is my risk tolerance?
Does my spouse want me doing this, or know I am doing this for that matter?
What market do I want to operate in? Is there a location where I have a strong network, intimate knowledge of the neighborhoods, or just a part of town that I really like?
After refining some of these answers, you can explore the wide range of investment opportunities available today. Some might include multi-family apartment investing, short-term rentals (think airbnb), house hacking (living in one unit and renting out the others in a multifamily primary residence), house flipping, self storage, limited partner syndication investing, or simply investing in a Real Estate Investment Trust (REIT) through a brokerage account. Each of these areas will offer a distinct level of risk, engagement, and minimum investment required.
Do Your Homework (But Not Too Much)
Once you’ve narrowed down the type of investing you want to do – now it’s time to do some homework. Countless websites, blog posts, books, and podcasts are available to help you learn everything — theoretically — about real estate investing. These are solid paths to explore to get a basic understanding of any particular segment of real estate investing you want to go into. My go-to list of resources for diving into real estate investing includes:
BiggerPockets – A comprehensive platform covering virtually every aspect of real estate.
Military to Millionaire – Tailored for the veteran and active-duty military community.
Living Off Rentals – Focused specifically on short-term rental insights.
Straight Up Chicago Investor – A podcast dedicated to Chicago-specific investment strategies.
When I mention not doing too much homework, what I mean is to focus more on action than on “book learning”. Avoid falling into the proverbial trap of "analysis paralysis," where overthinking and overanalyzing prevent you from taking action. I have learned more from the attempts that I took and failed at than any book has ever taught me. I love the quote, “If reading was all you needed to do then everyone would have a 6-pack.” While I have been lucky enough to bounce back from failures and setbacks, they are still some of the better teachers and will show you more than any book or podcast ever will.
Side note – there are a TON of “gurus” out there trying to sell you their course on how to get rich in real estate overnight. Be careful going down this path. Most people do not need to pay for or take a course; there is more than enough content on YouTube and across the podcast realm that will provide you with a free education. (I pay for courses that get me deeper on topics I want to explore, so not saying all are bad).
Build the Right Team
Real estate is a team sport and requires a large supporting cast to get the job done no matter what part of the industry you are operating in. In order to get the ball rolling, start developing your “A-Team” with at least the following professionals:
Realtor – Choose an agent who has been in the endzone before, particularly the endzone that you want to be in. Many agents claim to be experts in multifamily or investment properties to secure clients, but chances are they neither own investment properties nor have experience selling them.
Lender – Choose a lender who can help navigate the particulars of the types of deals you want to do. Most lenders cannot do loans for short term rentals. Most lenders cannot do loans for fix-and-flip projects. Finding the right fit here matters.
Attorney – You can never protect your backside enough when it comes to real estate. Make sure you have an experienced pro on your side to make sure that when you fail, you fail small. You should have a real estate attorney to guide you through the buying and selling process, as well as one specializing in tax appeals (they can be the same person, and that’s perfectly fine).
Insurance Advisors – Paying for insurance sucks, but we have to do it. Work with someone who knows how to properly protect you and your assets.
Investor Mentor – Find someone who is at least 5 years ahead of you in their particular real estate journey. Learn from them, especially their mistakes, to accelerate your progress and achieve greater success faster while minimizing risk.
Property Manager – There are a lot of property managers out there and a lot of them are terrible (just read their reviews online…). Interview several and choose the one that best aligns with your goals and objectives.
Contractors and Inspectors – You don’t need representation from every trade, but it’s wise to network with reliable general contractors (GCs) and inspectors, as their services will undoubtedly be needed in the future.
Accountant – You may not need the bean counters right away, but you will eventually. Having a good CPA on your side will help you tremendously when leveraging real estate as the great tax advantage that it is.
Prepare Yourself to Be a Good and Ready Investor
I tell my clients quite often that they should work on being a “good buyer.” What I mean by this is that they should have their financial house in order and get in the right mindset to be able to execute quickly when the right opportunity presents itself. Here are a few tips to help understand the importance of this step and ways to become that “good buyer”:
Have your money ready. If you are looking to buy an investment property and need roughly $100k, then make sure that money is accessible, liquid, and ready to rock and roll. Having your money ready a few months in advance will also help “season” it, meaning a lender can look back at a few statements and see that the money was in the account for at least 60 days. Be careful here though — sometimes you do not have to liquidate everything right away, and be extra careful around triggering tax events or violating any rules with retirement accounts.
Get all lender required documents and statements in their hands so they can move quickly when you do decide to get under contract. Make sure you fix any credit related issues, pay off any lingering credit card debt, and get your credit score as clean and as high as possible in advance.
Set your criteria and know what you are looking for. The more specific you can get here, the more likely you will know when the right investment property presents itself. Knowing what metrics are important to you is critical so you can quickly determine if a property is the right one for you.
Don’t do anything stupid like buy a fancy car or open a new Kohl’s credit card right before starting the process (or during, for that matter) of getting into real estate. This will create red flags during underwriting that could be problematic.
Get the team warmed up. Keeping everyone informed about your plans to make a purchase not only ensures they’re in the loop but also enlists additional eyes and ears to help you find the perfect investment.
I wouldn’t necessarily suggest getting any LLCs formed prior to buying; you can do those things fairly quickly once under contract. In fact, we only set these up once we know we are moving forward with a deal so as to not waste time and money. What is important here is to know what you are going to do. Most people, if they are not buying in their personal name, will set up an LLC through their state's Secretary of State website. Depending on backlog and what state you are in, this can take anywhere from a couple of days to a few weeks. It’s not extremely difficult (in most cases) but it’s always good to understand the requirements before you are scrambling to get it done.
Now Just Go Out and Do It!
Action is the best teacher, as we have said before. Although I’ve made mistakes in real estate, there are very few purchases I look back on years later and think, “That was a bad decision.” They say the best time to buy real estate was yesterday, and the second best time is today. We all know that going from zero to one is the hardest, so my advice to you is to do whatever it takes to nail down that first pin and start the ball rolling.
I firmly believe that once you’ve followed the steps above and assembled the right team of guides, you’ll be ready to dive into the world of real estate investing and secure your first (or even your 20th) property!
