I get asked this question quite often: "If you were starting over today, knowing everything you know now, what would you do differently?"

It's a fair question. I've been in this business long enough to have made most of the mistakes worth making, learned most of the lessons worth learning, and accumulated enough scar tissue to know what works and what doesn't—at least for me.

So here's my answer. Not as a prescription for everyone, but as an honest reflection of what I would do if I could rewind the clock and start fresh with the knowledge I have now and the personality I'm stuck with.

I'd flip three houses, then buy one rental property—preferably a duplex or small multifamily. Then I'd repeat that cycle. Flip three more, buy another rental. Keep doing that until I had ten rental properties generating consistent cash flow.

Once I had that foundation, I'd use the experience and financial leverage to start buying small apartment buildings, small office buildings, or light industrial space. The goal wouldn't be massive scale. It would be sustainable income from quality assets that don't require constant attention.

I would buy properties and seller-finance them as often as possible. I'd rather be the bank than the landlord. There's something deeply satisfying about receiving a check every month from someone who's building equity in a property you no longer have to manage, maintain, or worry about. The returns are solid, the tax treatment is favorable, and the headaches are minimal.

But I'd still be a landlord often enough to keep realizing the tax benefits that come with property ownership. Depreciation is a beautiful thing when you're actually holding assets. You just can't get those advantages as a pure note holder.

Now, here's where I need to be clear about something: this strategy reflects my interests, skills, and personality. It's not a judgment on other asset classes or other people's choices.

I would not rule out short-term rentals, but hospitality management isn't my thing. I know people who absolutely crush it with Airbnb and VRBO properties. They enjoy the guest interaction, they're good at creating experiences, and they don't mind the constant turnover and detailed management. That's not me. I have neither the temperament nor the desire to manage that level of detail repetitively.

For the same reason, I'd probably stay out of trailer parks and self-storage facilities. Both can be extremely profitable asset classes with excellent returns. I know investors who've built substantial wealth in both sectors. But the level of hands-on management they require doesn't match my skill set or my interests. That's a statement about self-knowledge, not a criticism of those investments.

Understanding what you're good at and what you actually enjoy is as important as understanding what makes money. You can force yourself to do almost anything if the returns are high enough, but sustainable success usually comes from aligning your business model with your natural inclinations.

Which brings me to the two things I would absolutely, unequivocally change if I could do it over again.

I would have bought rental properties only in solid, stable areas with good schools and diverse employment opportunities in landlord-friendly suburbs.

Instead, I bought some properties in areas where the numbers worked but the people didn’t. The properties seemed affordable but I didn’t consider whether they were actually desirable. These were places where I thought I was getting a deal without asking whether there was a reason the prices were so low.

Good schools matter. Even if your tenants don't have school-age children, good schools signal stable property values and attract better tenants. Diverse employment opportunities matter because when the dominant employer lays off workers or leaves town, your rental market evaporates overnight. Landlord-friendly laws matter because fighting an eviction for nine months in a tenant-friendly jurisdiction will teach you that lesson the expensive way.

Location isn't everything, but it's close. A mediocre property in a great location will outperform a great property in a mediocre location almost every time.

I would have been much more selective in my hiring choices. I would have insisted on demonstrable skills, not just hired friends who had done pretty well in a lesser role.

This one hurts to admit because it means acknowledging that loyalty sometimes clouded my judgment. I hired people I liked instead of people who could actually do the job at the level I needed it done. I promoted based on potential rather than proven ability. I convinced myself that someone who was good at Task A would naturally be good at Task B, even when those tasks required completely different skill sets.

Sometimes it worked out. Often, it didn't. And when it didn't work out, I waited too long to make the change because I didn't want to hurt feelings or admit I'd made a mistake.

I gave people too many chances. I tolerated mediocre performance too long. I let relationships interfere with business decisions that should have been straightforward.

If I could do it over, I'd hire slower and fire faster. I'd value demonstrated competence over personal connection. I'd remember that being a good person doesn't automatically make someone good at a job, and keeping someone in a role they can't handle doesn't help them or you.

Those two errors—location choices and hiring decisions—cost me more than I care to discuss in detail. I pray you will learn from my expensive mistakes so you don't have to pay for your own version of them.

But here's the thing that might surprise you: eliminating those two big mistakes are the only thing I’d change.

After establishing that rental property foundation and building some financial stability, I'd launch a podcast. I'd interview lots of people in the industry. I'd quickly figure out that apartment syndicators really want to be on podcasts, and over time, I'd identify the few I actually trust enough to invest with.

Then I'd start sharing my knowledge and experience with others. Partly for the income, because teaching and consulting pay the bills. But mostly for the joy that comes from helping people realize their dreams and avoid the mistakes I made.

That's what I'd do. And except for those couple of expensive detours, that's what I have done.

Real estate investing isn't a path to easy money. It's not passive income that requires no work. It's not a get-rich-quick scheme or a shortcut to wealth. It's a business that rewards knowledge, discipline, good judgment, and the ability to learn from mistakes—yours and other people's.

But it's also one of the most reliable ways to build wealth over time if you're willing to do the work, make smart decisions more often than stupid ones, and keep going when things get hard.

Would I do it all again? In a heartbeat.

Would I make the same mistakes? I hope not. But I'd probably make different ones, because that's what happens when you're actually in the arena instead of watching from the stands.

The question isn't whether you'll make mistakes. You will. The question is whether you'll learn from them, adjust your approach, and keep moving forward.

That's what I did. That's what I'm still doing. And that's what I'd recommend to anyone asking me where to start.

Begin with what you can do now. Build systematically. Learn continuously. Be honest about your strengths and limitations. Make better decisions than I made about location and hiring. And when you inevitably make mistakes anyway, own them, learn from them, and keep going.

It's not a perfect path. But it's a real one. And after all these years, I still believe it's worth walking.

Keep asking - wisdom is on its way.

Roger

p.s. It’s not specifically career-related, but I would find Dianna sooner if I could, and marry her as quickly as she would say “yes.”