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Diving into “Over Ask,” the Award-Winning Podcast by The Agency’s Matt Lionetti

by | Sep 12, 2022

Between delivering not one but two featured speeches at Inman’s latest Connect Conference and being crowned the winner for Best Podcast of the Year by the Inman Innovator Awards, The Agency’s Matt Lionetti is showing no signs of slowing down. Based in Toronto, Canada, Matt has built his brand on funny, clever and sometimes polarizing content that demands attention, whether you like it or not. After his success with several viral videos—which fetched millions of organic views on social media—Matt turned to podcasting alongside friend and founder/owner of Broke Agent Media, Eric Simon. 

Eric and Matt’s podcast, Over Ask, dives headfirst into the world of real estate and features industry gurus as guest speakers covering topics ranging from how to go viral on Instagram to how to sell a $100 million home on a time crunch. The Agency sat down with Matt to talk about the success of the podcast, advice for agents finding their niche and what lies ahead. Here’s what he had to say. 


Q: What inspired you to start a podcast? 

Eric Simon and I had been collaborating on content together for over two years before we decided to take our partnership to the next level. We had both seen success on social media through short-form videos and had built organic followings, but we wanted to show our audience that we can be more than just the “funny guys.” This podcast was a chance for us to share more of our market expertise and personality with our audiences. From the time we came up with the idea for Over Ask to the time the first episode aired was maybe four weeks total. We hit the ground running and we did it all by ourselves. When we landed Jordan Cohen, the number one RE/MAX agent in the world for our first episode, and then Ryan Serhant, founder and CEO of SERHANT, we were able to leverage that momentum to propel the rest of the show forward. I don’t think either of us has looked back since. 


Q: Tell us about your relationship with podcast co-host Eric Simon. How did you two meet and how did the idea to start a podcast together come about? 

Eric Simon is the OG of real estate humor. He’s based out of L.A. and I always admired his content and social media presence. Soon after I started producing short-form videos on social media, I reached out to Eric. We became fast friends. It wasn’t long before we were bouncing ideas off one another and discussing new ways to further our careers and stand out. It was always really easy working with Eric—I think we share a similar mindset surrounding social strategy and content creation, and we’re often on the same page. 


Q: Did any particular podcasts give you inspiration for your own? What are some of your favorite podcasts right now?

Eric and I are both really into podcasts and love listening to them. I felt that when it came to real estate podcasts, however, there was a major lack of personality. They tended to be analytical, dry and statistics-driven. I wanted our podcast to bring value to our listeners, but I also wanted it to entertain. We call it “edu-tainment;” the sweet spot between education and entertainment, and that’s exactly where “Over Ask” lives. When we started, I didn’t want to compare ourselves to other agents because I didn’t want to be the best in real estate, I wanted to be the best period. Right now I’m listening to 2 Bears 1 Cave with Tom Segura & Bert Kreischer, The Joe Rogan Experience and King and the Sting and the Wing


Q: You’ve released a lot of “Over Ask” episodes with topics that range from “going viral” on social media to advice for selling luxury real estate. What’s been your favorite podcast topic and why? 

Early on in the podcast we did an episode with Managing Partner of The Agency’s British Columbia offices, Jason Binab. He brought an entirely unique point of view to the real estate business as he spoke on mindset, love languages, human interaction and the law of attraction. I’m very much a believer that what you give into the world you’ll get back and hearing Jason’s thoughts on this topic was really interesting. 


Q: You were recently the winner of Inman’s 2022 Innovator Awards for Top Video/Podcast. Kudos! How has “Over Ask” impacted your real estate career? 

When I started Over Ask, I didn’t know what to expect, I just wanted to create something new, but the reaction to the podcast and the impact it’s had on my career has been extremely rewarding. It got my name out there and allowed me to showcase the knowledge I have in the space. After the first few episodes, I got a direct sales lead for a $1,300,000 house! I’m grateful that the podcast has added another layer to my business and that listeners now know me as more than just the funny, meme guy. 


Q: You and Eric just released your 90th episode—congrats! Looking back on your journey, is there anything you wish you had known before you started? What advice would you give to an agent looking to start their own podcast? 

Podcasts are a ton of work! Both Eric and I had pretty big social platforms to start but you still have to earn followers on a new platform. For people trying to start a podcast, my advice would be to focus on content and know that it’s never going to be perfect. You can have the best technology out there but if the content isn’t quality, then no one is going to listen. You also need a certain willingness to take risks. Over Ask has progressed over time as a result of the risks we’ve taken and we’re a lot better than we used to be at holding conversations and being purposeful about how we navigate the conversation. It’s also made me a better negotiator; the skills I use in real estate on a daily basis have greatly improved as a result of this project, which is an outcome I never imagined. 


Q: Have any advice for agents looking to find their niche? 

My best piece of advice is that it has to work for you. You can try all different kinds of things to promote your business but people will see right through it if it’s not true to who you are. Find a niche that suits you and double down on that. The second I niched down on marketing and humorous videos was the moment my career opened up. 


Q: Rumor has it you have a new show in the works. Can you give us a sneak peek of what it’s about? 

I’m very excited to be debuting a new show coming out this Fall called Cold Calls with The Agency Toronto’s Paul Greenberg. It’s essentially a real estate-style Loveline where people call in and share their real estate horror stories with us. Paul and I are really looking forward to sharing this when it’s ready. It’s interactive, easy to digest and relatable to agents and clients alike. 


Listen to the latest Over Ask episodes (and catch new ones, released weekly) on YouTube, Spotify and Apple Music

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