260 Rentals and 850 Flip and Wholesale Deals with Andrew Holmes

For this episode, I welcome fellow real estate investor, Andrew Holmes. Andrew built the #1 flipping team in Chicago and completed over 850 deals in the Chicago market. He owns over 250 rentals and more than 2 million in assets. He started the Chicago Real Estate Investors Association which has become the #1 Real Estate Association in the US. Andrew has worked with over 450 investors in the Chicagoland area helping them develop a rental portfolio of more than 2800 rentals. Andrew and I started investing in real estate around the same time - he absolutely killed it and I am absolutely thrilled to learn about just how he did it in today’s interview.

Andrew first shares his background story and how he got his real estate license back in college with money designated to pay for his studies. He shares further along in the interview how this is something he has never even told his parents about!

We then moved on to discussing how Andrew got started seriously investing at the age of 32. We discuss his first year in business where he completed an astonishing 10 flips. Having done two flips myself in the same year, I was extremely interested to learn about just HOW he did it without burning out. Andrew then explains how he made the first investment himself, before securing further financial investment from two business contacts. The growth just continued exponentially after that.

Together we then dive into discussing the sheer operational challenges of rehabbing this number of properties at the same time and Andrew shares how he got started with a less-than-perfect Jack-of-all-trades contractor - and how he slowly transitioned out of moonlighting and into working with proper contractors. Lucky for him he realized that the stress of working all night just wasn’t worth it after about the third flip. Andrew then shares that as the number of flips he completed grew, the profits started to fall.

We discussed how his parents have influenced his outlook on life. Having both been hard-working, well-qualified surgeons, Andrew’s parents saw themselves as true professionals and they expected nothing less than that from Andrew himself. Andrew however saw two people who worked extremely hard and didn’t have all that much to show for it. Andrew made it his goal to show his parents that he will also be successful but in his own way. He describes how as a child he has always had big dreams and has more often than not been considered crazy for even talking about it.

Eventually we discuss how the constant pressure of keeping up and the lack of security was making Andrew feel less than safe and his focus shifted to buying wholesale. Andrew shares the super simple formula he used for transitioning to owning rental properties - the 2-5-7 formula. Listen to the episode to get all the details on how it works. He told me how he started with just a handful of properties and then scaled it up from there.

We then move on to the topic of choosing the right properties to invest in. Again, Andrew shares some gold nuggets here about the exact criteria he uses to assess whether or not a property is worth investing in or not. That’s the exact system that got him from 3k a month cash flow to 100k a month cash flow.

We talked about the logistics of managing 260 rental properties. Andrew manages the properties in-house with just full-time managers, 1.5 rent collectors, and a team of contractors. He gives us an important reminder to never buy individual properties outside of your area, as this adds unnecessary workload.

Lastly, we discuss the importance of networking. Andrew shares how just studying the information just isn’t enough and how important surrounding yourself with people that are actually DOING IT has been for him - and as always I absolutely agree with his assessment. Don’t miss this episode of Just Start Real Estate that is filled with practical and incredibly actionable advice from uber-investor, Andrew Holmes!

Notable Quotes:

“I was born in the US but most of my life I’ve grown up in India. You don’t learn DIY in India.”

Andrew Holmes

“From a small fire, I jumped into a forest fire doing that many flips.”

Andrew Holmes

“My family found out I was flipping houses because I did it so long and had some success that I was being interviewed and my family read about me in the paper.”

Mike Simmons

“I didn’t tell my wife that I was doing this - I just didn’t want to fail.”

Andrew Holmes

“When my parents didn’t have an answer I got a whack on the head ‘Go Study.’”

Andrew Holmes

“I felt scared. Even though I made good money. I always felt scared. If I went on vacation I felt guilty and I was sick and tired of this feeling. I wanted some security in life.”

Andrew Holmes

“I tried being poor and I didn’t like it.”

Andrew Holmes

“I thought I was investing, but in fact I was just trading properties.”

Andrew Holmes

“My goal always was that one day I’m gonna make my parents proud. And I’m going to buy them something that’s going to blow their mind.”

Andrew Holmes

“I don’t have to worry about how much it costs or what it is. It’s just a small part of what real estate has helped me do.”

Andrew Holmes

“I didn’t drink, I didn’t party. I was just focused.”

Andrew Holmes

“We do what’s called 2-5-7 and that’s what I try to convince everyone to do. Cashflow for life. I tend to be very fanatical about those numbers.”

Andrew Holmes

“I keep things very simple. I’m not a very educated human being. I can understand basic things and I stick to basic things.”

Andrew Holmes

“If you take care of real estate for the first five years, real estate will take care of you for the rest of your life.”

Andrew Holmes

“I was always looking for answers. While my friends were partying, I was reading books. Reading books, all it does is give you insomnia. Because you’re excited and you don’t know what the hell to do.”

Andrew Holmes

“The more I give away, the more I get to learn.”

Andrew Holmes

“Everyone talked a good game, but no one was doing anything.”

Mike Simmons

“If you think surrounding yourself with people who are actually doing the business at a high level, that you won’t be able to exponentially increase your learning, your growth and your business - if you don’t think that’s going to happen. You’re dead wrong.”