Zen and the Art of Real Estate Investing with Jonathan Greene

The Backstage Guide to Real Estate Investing with Matt Picheny


One common theme among real estate investors is that they stay working at their job until they’re able to do real estate full-time. You obviously need capital to do the investment. But aside from that, there are a couple of other things you have to consider to ensure your success in the real estate investing space before fully diving in.


Matt Picheny, a real estate investor, Tony Award winner, and author of the best-selling book, Backstage Guide to Real Estate, shares these insights into real estate investing, especially as a new investor.


Identifying What You’re Good At – and Not

Identify what you’re good at in the investing field and what you know you’re not good at. The longer you spend trying to do this stuff that you’re bad at, the worse decisions you’re going to make, and the more frustrated you’re going to be. And so, see if there’s somebody else who can do it for you – even if it’s 80% as good as you so you can then do something else. 


Your Best First List

Make a list of all the family and friends that you like and every place that you’ve ever lived. And then compare those two markets that are maybe potentially gentrifying. There will be some that touch all those bases because you did exactly what you do. For instance, Cleveland doesn’t have to be the best market but the prices are great. Maybe you had someone check up on the property or maybe you know the area yourself. This gives you a more comfortable feel than just picking it randomly just because somebody told you it’s a great place to invest. But you don’t know anyone there and you don’t know any contractors. 


Look for properties that you could do a value-add on and it has to be in a good area. You don’t want to buy property in an area where the population is declining. Because then no matter how much value you add, there’s not going to be any demand. Hence, look for an area where there is demand and where there is market growth because employment growth leads to population growth. 


Building Your Group of Investors 

Relationships are an important part of this journey so be able to build authentic relationships. Send useful updates on a monthly basis, investor tips and knowledge, and all kinds of cool stuff. Be clear about your role in the deal, whether you’re a limited partner or a general partner. Get as much exposure as you can so investors can see you and what you’re doing. Be a guest on a podcast, publish a book, get featured in an article, or speak at conferences. Not only are you getting yourself out there, you continue to grow as an investor too.

If you want to learn more about the Backstage Guide to Real Estate Investing with Matt Picheny, check out

Leave a Reply

Your email address will not be published. Required fields are marked *