I just answered this question somewhere else and found it interesting to think back on my own false beliefs and misconceptions.  Thought it would deserve it's own post for new investors to get a look behind the curtain and see how people who are investing 10+ years got started.

15 years ago I bought my first rental property. Many more followed, but I did not know that at the time; my goal was to buy one.

Like for so many, it all started with reading RichDad: I felt like I discovered a whole new universe in it was filled with shiny objects everywhere, I was hooked. Then I read pretty much every book I could find, bought every CD course to listen to and finally signed up for a year of one-on-one coaching with Rich Dad Education. It was basically a home study course and had to complete weekly assignments, do home work and then present to my "coach" who was a girl in a call center. She was very good at making me feel that they all owned real estate and had great success with it, while skillfully evading all of my specific questions.

After all that I still did not feel ready.

Eventually, I turned to my real estate agent, who was a sweet lady in her mid 70s named Alice, who did not own a computer or a cell phone and did not know much about basement issues or cash flow. But I was hell bent on getting a really good deal and made that poor woman write an offer on a short sale. I thought if its a short sale or a foreclosure, that would make it a good deal - lol. It took half a year to get the deal through with the seller's lender, my poor agent finally got paid a few grand for all of that.

I was beyond concerned at closing: what if I can't find a renter? What if there are no renters in that area? What if the roof needs replacing? What if I have to admit to my family that my big dream of becoming a real estate investor ended up being a complete disaster?

Next step was to fix the place up, best I know at the time. And get it rented. I basically stumbled through that process, some hooked me up with a good local lease form (Wisconsin Legal Blank - we still use them) and somehow got it done. I will never forget the day when I walked to my mailbox and found my first rent check! Holey cow!! This was actually working!!

Looking back: it is funny how concerned I was about knowing enough and "getting ready". I basically wasted 2 years of probably the best real estate market in my life time. One big mistake I made was that I really wanted a good deal. Getting a good deal was somehow more important to me than getting a good property. Duh. In fact, I was looking at a duplex across the street, same age, same brick exterior, but about 50% more living space per unit. It was about 20% more expensive and I thought that was too risky, I should buy the smaller one. That was probably my biggest mistake at the time, because rents for 750 sqft units are limited - even years later after a complete remodel with new kitchens and bathrooms, the rent was capped by the size of the units.

I was way to concerned about learning and "getting ready". All that stuff you think you have to do like starting an LLC and having a logo and a business card. In hindsight I find that almost laughable about myself, but I see it today when people on BP are asking the very same questions I had. And they don't want to hear the advice, because they somehow feel it can't be that easy.

But it actually is. Real estate investing is totally common sense. You will learn a lot, but that starts after you bought your first deal. You can't learn swimming from a book. There are a few principles I try to share with new investors. You don't need to make all your money on your first deal. Buying a good property is 10x more important than buying a good deal. You can test that by searching BP and looking for what people regret: nobody every complains about buying a good property in a good neighborhood. But many crash and burn over a hood property they are not equipped to handle. The longer I do this the more I migrate to higher price points and higher quality.

7 years later I quit my corporate job and became a full time landlord: I thought I had achieved the dream and got out of the rat race. My passive income had exceeded my active income. It still felt like jumping off a bridge. But I am also glad I stuck it out with corporate as long as I did. I was compensated very well and it allowed me to grow, fund more deals and continue to get financing. What I also learned is that being retired and sitting at home was not for me, I got bored pretty quickly and decided to get licensed. I was never quite happy with any of the agents I worked with, so it seemed like a good step. I hung my license with Keller Williams and the first thing I realized is how little I knew. I thought I was going to kick a** with my investor experience; - boy, did I have to eat some humble pie. I fell flat on my face. I joined a team, which was a good decision and accelerated my learning curve. Eventually I got to doing about 40 deals per year, started my own team, started a YouTube channel about Milwaukee - it became a whole thing and I don't regret that part. But the first two years after getting licensed where the weakest as an investor. I just did not have the investor mindset anymore and my attention was with clients. Eventually I was able to get buying rents back on pace, but it took me a while. That's the reason why I am telling investors on BP that I don't think it's worth getting licensed. You know nothing and you should not hire yourself.

Which brings me to another point. A good agent is the key to EVERYTHING. Investor friendly agent means an agent who owns and operates rental properties. Most new investors get that wrong, they think someone who is willing to run around a lot for little money is what makes an agent investor friendly. IMO a good investor agent has walked the path; they own properties. They can tell you from their own experience what to buy and what not to buy. They know market rents, they know rehab, they can hook you up with the right lender. And with good leases, give you the basics on landlord-tenant law, how to do a background check and everything else. I used to work with investors when I got started as an agent. I don't do that anymore, partially because I focus on luxury and relocation business, partially because I gave so much knowledge away for free and it was generally not appreciated - especially when I see in comparison what people get for a 30k guru course, and value that generic advice over my first hand field experience. What really killed me was when a new investor called me about buying a hood property and I tried to give them some advice about that, I often got: "Thank you for your time, we are not a good fit, I am looking for an investor friendly agent. Click." - WTF??

Here is another common mistake new investors make and they don't understand it at the time. Finding the good investor agent is harder than you think and requires effort, but it makes everything else so much easier. I see it with one of my agents, who was actually an investor client of mine a long time ago: he just had a listing that had some bad issues that needed fixing before the property was ready to market, he diagnosed the issues, set up a SoW designed for ROI, managed the whole construction process, provided the contractors he know who work for a really good price: he did a lot more than 99% of agents I know could have done.

After my first deal I realized that my agent Alice was really a fish out of water with rental properties. When it was time to look for my second property I decided I wanted to work with a different agent. The problem was that every single one of them told me they were basically experts for investment properties. I could not tell the difference right away and it was incredibly frustrating, because being an engineer I would realize eventually how little they knew about construction issues - and pretty much every property I looked at at the time needed work.

All of this is to say: your first project is to find a good agent and that means someone who owns properties - and not someone who just works with investors. I have some internal investor training at my brokerage, because I think every agent should buy rental properties to at least supplement their retirement. What I found doing these classes, is that everyone wants to, but almost zero agents ever do. They just want to learn a little investor lingo, so they can pick up rinse and repeat clients. I am sharing all this because I think it can help you understand whats happening behind the curtain at brokerages. Bottom line, you have to be systematic to find the right agent. It is not going happen casually along the way while you are looking for a deal.

One of my favorite business books is called the The ONE Thing. The guiding principle is: What is the ONE thing that I can do today that will make everything else easier or unnecessary? When you start asking that question on a daily basis, small things start to compound over time. Most investors I have worked with over the years have never grown beyond one or two properties. Only two of them got to about 20 - 30 over the course of maybe 7 or 8 years. And one guy made it to 5000+ doors. I have great respect for him. He used to be a corporate manager at Target and relentlessly applied a corporate approach to building his business. When you look at the deals he has bought, none of them were "great deals", but they were good properties. What makes him really stand out is he is an exceptional operator. To give just one example: his service and repair staff is trained (and financially incentivised!) to get 5 star reviews by the tenants on Google for the company. He has Tenant Experience Managers. I have seen some of his rent projections for acquisition projects and remember thinking good luck with getting that much! They will show up with 5 trucks and 30 people at the property the day of closing (not the next day!) and within a week they have the entire landscaping and exterior done. They turn over units in 5 days including kitchens and bathrooms. The velocity and quality of execution are insane.

Last point: The 2010s were an incredible opportunity to get started in REI. With the market conditions it was a great time to grow using the BRRRR approach. But a lot has changed: real estate prices are much higher, real estate investing has gone main stream and mortgage rates don't help either. You won't be able to find the same level of deals today anymore. I have never taken money out of my REI and always reinvested everything into property upgrades. So living off cash flow never happened for me, even though I could have. But today it's impossible, at least for the fist 7-8 years.

The opportunity that exists today if you get started is to put AI to work. You can basically set up a project in Claude (or Chat) and create your own real estate coach. Provide all the information about your local market and about you, it get can the rest from online sources and even research BP. The second advantage is that you can use AI to create a cash flowing business that can fund your real estate investing. That combination of small biz + REI is incredibly powerful. A small biz is by design a cash flow machine. RE is not good in cash flow: it does a little, but it's real power is growing equity - NOT cashflow. AI can help create an online biz or help you find a real world side hustle biz that makes sense for your skillset.