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As a Long-Time Real Estate Investor, Here’s What I’d Do Differently If I Was Just Starting Out…

M. Ian Colville
3 min read
As a Long-Time Real Estate Investor, Here’s What I’d Do Differently If I Was Just Starting Out…

Seasoned investors: If you could do it all over again, what would you do differently?

As someone who has been in the real estate investing industry for more years than I’d like to think about, I often get asked that question. Wouldn’t it be great to have the opportunity? The chance to do it again with the knowledge and experience I have today?

Of course, I can’t do it all over again—but I can provide suggestions for those just starting out.

So, what would I do differently, and on the flip side, what things did I get right and wouldn’t change?

What Would I Recommend to New Investors?

First, let me start with a few tried, true, and timeless investing pearls of wisdom. These are things I think most investors would say they wish they had done differently. These pointers stand the test of time, regardless of the market conditions when you start your real estate investing.

1. Start investing earlier.

This is the most obvious one— just about everyone I know wishes they had started earlier. Time is on the real estate investor’s side. We all know the market has its ups and downs, but the sooner you get in, the easier it will be to ride out the bumps.

I feel like I got in at a good time, but I would have been able to buy properties even cheaper if I had started earlier.

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2. Use debt more aggressively.

This one dovetails with starting earlier. If you start early, you likely don’t have a ton of cash. So, you need to leverage other people’s money.

And when you start earlier, you can take on more risk. If some of the deals don’t work out, you’ll have time on your side in terms of recovering.

3. Take more risks early.

This one also ties into starting sooner. As mentioned, if you start early, you can take more risks because you have time on your side.

What Would I Have Done Differently?

Next are things I specifically would have done differently.

1. Limit the geography of properties.

We own properties in five states. I would put more money into fewer markets if I had to do it all over again.

It has been a lot of work to manage properties in so many locations. We have made money for our investors in the process, but we probably could have grown faster if we hadn’t been as stretched by managing this number of locations.

2. Delegate sooner.

I have built a team over the years, but we probably could have grown faster if I had done this sooner.

Related: 5 Smart Tips for Outsourcing & Delegating Work in Your Real Estate Business

3. Expand into commercial buildings (from single family homes) quicker.

Our commercial projects have done very well. I wish I had started this expansion sooner, as there is less competition from buyers in the commercial space.

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4. Leverage technology better.

Especially today, technology can be a fantastic tool for investors. But getting the right technology and knowing how to use it and leverage it to its fullest can be a challenge.

We started out using Propertyware and found it too complicated. So, we switched to Buildium for a while and soon found it too simplistic—and ended up switching back to Propertyware.

This switching was painful. I wish I had taken the time to learn Propertyware better from day one to avoid this pain.

What Wouldn’t I Change About My Investing Journey?

Finally, here are a few things to help you get it right from the start, most of which I had the good sense to do and wouldn’t change.

1. Just start.

This can be one of the biggest hurdles for many. You just need to start. And the sooner you do the better.

Related: Hesitant to Invest? Hack Your Way Out of Analysis Paralysis

2. Get educated.

No need to reinvent the wheel here. There are many educational opportunities to take advantage of.  And with so much technology available today, it is easier than ever to educate yourself.

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There are webinars, podcasts, investment groups, and more. Of course, many “educational” programs are ultimately trying to sell you something. But even so, much can be learned with little to no cash outlay.

3. Get a mentor.

A mentor can be an invaluable asset. Believe it or not, there are people out there who are willing to share their expertise—just out of the goodness of their being—without wanting anything in return.

If you can find one, stick with them and learn as much as you can. Especially if you are on your own, having someone to bounce ideas off can be a tremendous asset.

4. Stay focused.

I attribute at least some of my success to focus. I had a plan and stayed true to that plan in terms of the type of properties I wanted to invest in and my investment strategy.

It can be easy to get side-tracked as opportunities come along. So I would say, be clear about your goals and objectives, set your strategy, and then stay the course.


Real estate investing is a great business to get into, and I’ve been fortunate. Looking in the rearview mirror, there isn’t too much that I would do differently if I had to do it all over again.

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Any tips you’d add to this list? Questions for me? 

Let’s talk in the comment section below.

Note By BiggerPockets: These are opinions written by the author and do not necessarily represent the opinions of BiggerPockets.