How This Agent Went From NOTHING to Selling Real Estate Properties

Anna Oliver joins Matt Lionetti and The Broke Agent to discuss how to be consistent in selling luxury real estate, changing markets during a recession, the mentors that shaped her as an agent, an unedited video that went viral, and why she and Matt decided to team up.
Businesswoman in a black top smiles on a pale yellow banner with the bold headline 'SELLING LUXURY FROM NOTHING'.
Businesswoman in a black top smiles on a pale yellow banner with the bold headline 'SELLING LUXURY FROM NOTHING'.
BAM Fest 2026

Join Sharran Srivatsaa, Chris Smith, Selene Hanna and a huge Mystery Guest for a live breakdown of the AI and content strategies driving more closings right now. Completely virtual and 100% free. Click HERE to reserve your free spot today.

FREE VIRTUAL EVENT
BAM Fest 2026

Join Sharran Srivatsaa, Chris Smith, Selene Hanna and a huge Mystery Guest for a live breakdown of the AI and content strategies driving more closings right now. Completely virtual and 100% free. Click HERE to reserve your free spot today.

This week on the Over Ask Podcast, Anna Oliver joins Matt Lionetti and The Broke Agent to discuss how (and why) she moved to Toronto after building a successful real estate business in Halifax—and what led to her having to start all over during a recession. 

From there, she talks about what she did in Toronto to learn the market and build her client base, experiences she had with other real estate teams before she joined The Agency, how she and Matt Lionetti met, and how they decided to team up and collaborate on listings. 

Stay tuned to the end to hear about an unlisted video that went viral, what she learned from the fallout, and how she and Matt are carving a new space in the luxury real estate market. 

Click on any of the timestamps below to watch: 

00:0000:34 Intro

00:34 Meet Anna Oliver

13:44 How she built her client base in Halifax

16:14 Why she moved from Halifax to Toronto

18:51 Working on demolition crews while learning the market

21:20 Walking/driving Toronto neighborhoods & getting dumped from a team

23:52 “Was there one deal or client that changed everything for you in Toronto?”

27:20 How Anna and Matt connected and decided to team up

34:14 Carving a new space in the luxury market

38:03 The mentors that shaped her as an agent

42:37 Agent reputation and an unedited video that went viral

55:00 What agents can learn from Matt & Anna’s real estate partnership

Click here to watch the full episode.

This week’s Over Ask Podcast is brought to you by BoomTown. Click here to learn more.

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Real estate may be all about location, location, location, but we know that content is king! That's why we have an army of talented writers behind the scenes, crafting posts like this one to help you navigate the ins and outs of the industry.

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