From Stand up Comedy to Selling Ultra Luxury Real Estate with Zach Goldsmith

The Broke Agent and Matt Lionetti sit down with Zach Goldsmith, a 20-year luxury real estate veteran. They discuss how Zach prepares for multi-million dollar listing presentations, learning from Jeff Hyland, and his recent switch to Mauricio Umansky’s The Agency.
Promotional banner: a man in a dark sweater beside bold text reading '$10 MILLION LISTING' on a pale yellow patterned background.
Promotional banner: a man in a dark sweater beside bold text reading '$10 MILLION LISTING' on a pale yellow patterned background.
BAM BBQ 2026

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FREE VIRTUAL EVENT
BAM BBQ 2026

If you're still treating AI like a search engine, this is for you. BAM BBQ is two and a half hours of real instruction on AI for real estate, from conversations to content to systems. It’s free, virtual, and loaded with plays you can run the same week. Save your spot →

Join hosts The Broke Agent and Matt Lionetti as they sit down with Zach Goldsmith, a 20-year veteran of the industry with a wealth of knowledge and experience to share.

From his early days in stand-up comedy to his current role as a top luxury real estate agent, Zach shares his journey and the lessons he’s learned along the way. Discover how he prepares for $65 million listing presentations, how he handles deals that don’t go as planned, and how he won back a client on a recent deal.

But that’s not all – Zach shares how Jeff Hyland’s mentorship has shaped his career and helped him become one of the most successful agents in the business. Plus, how his superpower as a chameleon helps him connect with clients and why he recently made the move to join Mauricio Umansky’s The Agency.

Don’t miss this engaging and informative conversation:

Click on any of the timestamps below to watch: 

00:00 04:10 Intro

04:55 How Zach went from stand-up comedy to real estate

10:00 Why Zach doesn’t make calls

13:37 Being a chameleon is a superpower

17:17 Zach’s move to the Agency (and being jealous of Matt)

26:31 How Zach navigated his sphere to enter the world of ultra-luxury real estate

29:45 Prepping for a $65M listing

37:35 Winning (and losing) based on your personality

38:50 What Zach learned from Jeff Hyland

42:50 A listing presentation that bombed

48:12 Winning back a client through optimism 

53:34 What Zach does on the days he doesn’t feel like getting out of bed

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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