Alright – so today we’ve got the honor of introducing you to Matthew Tortoriello. We think you’ll enjoy our conversation, we’ve shared it below.
Alright, Matthew thanks for taking the time to share your stories and insights with us today. So, let’s imagine that you were advising someone who wanted to start something similar to you and they asked you what you would do differently in the startup-process knowing what you know now. How would you respond?
The first thing is understanding the importance of picking the right partner. One of the biggest things that happened early on was that we chose a couple different partners that were problematic for different reasons. Structuring and understanding partnerships and the value that is added in the right context would have helped a lot. Putting controls in place would have made a big difference for us. For instance, we had one partner that was stealing money out of the account. They said they owned multiple rentals but it turns out they didn’t. We also had another partner who wanted to have full control and was slowing all of our processes down. Now I feel like we have removed those hinderances. If we hadn’t had these partnership issues early on it would have allowed us to grow much faster.

Matthew , before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
My name is Matthew Tortoriello. I am a real estate investor. I’ve been in this business close to 30 years now. I started investing in real estate when I was 16 years old. I’m sure you’ve all heard this story before but, I got into this business after reading the book, “Rich Dad Poor Dad”. I got super excited about it and tried to find my first rental property with my Dad. I found a two family house in Pittsfield, MA, purchased it and quickly realized the book didn’t COMPLETELY teach me everything I needed to know. I quickly thought to myself, “how the hell am I going to do this?!” Luckily, I figured it out as I went along. I ended up selling that two family home and made a little bit of profit. Many years later, we have gone from owning single family homes to, two, three unit complexes to larger apartment complexes, owning shopping centers, self storage facilities, car washes and industrial buildings. We’ve owned a lot of different types of real estate assets. We have diversified ourselves to protect us from the downsides of one market. We also put together our own property management company. We are always looking to find assets to add to our portfolio.

Can you tell us the story behind how you met your business partner?
I met my business partner, Kevin Shippee back in college. He was teaching a tae kwon do class and I decided to check it out! He was definitely an interesting instructor. After some time, we started to hit off and became friends. He was a communications major and I was a biology major with a minor in Chinese. We might not have had any classes together but we definitely found plenty in common (especially gaming). I started sharing my GREAT ideas with him about how we could make all of this money from real estate investing and how the concept of a partnership could be beneficial. Years later our real estate business also started to transform into becoming social media influencers!

We’d love to hear the story of how you built up your social media audience?
We got started on social media during the COVID era. Kevin and I were bored one day and started to watch other real estate influencers online like Ryan Pineda who had a large following. We saw how well he was doing on social media and thought, “hey this could be another way to capitalize and share our knowledge”! Especially since we were already having so many people coming to us and asking for opinions on how they could get into real estate. We were always happy to share our experience and knowledge with others so we decided to make our first YouTube video! Let’s just say our early videos were CRINGY and low quality. We kept the ball rolling with TikTok videos and tried our best to keep up with the latest trending sounds and that is when we really started to take off. If you’re looking to get started on social media. my advice would be to pick a niche in your lane. Don’t try to be broad. Niche down and focus on adding value. If you add value within your niche market, the followers and subscribers will come!
Contact Info:
- Instagram: https://www.instagram.com/twoguystakeonrealestate?igsh=MXB1a3djaWV2cXlsNg%3D%3D&utm_source=qr
- Twitter: https://x.com/2guystake?s=21&t=Fo56aVf_dUN3tiXOI4ZB-Q
- Youtube: https://youtube.com/@twoguystakeonrealestate?si=IkMA4_ZIlf9IY9Dx
- Other: Our book Foreclosures Unlocked:
Audio Book Version:
https://www.amazon.com/Foreclosures-Unlocked-Success-Estate-Investing/dp/B0DTBFSK8T



