From Hospitality To Over $1 BILLION In Real Estate Sales

Aspen real estate agent Heather Sinclair joins Matt Lionetti and The Broke Agent to talk about switching from hospitality to real estate, working with ultra-luxury clientele, and how to become the sheriff in your market.
Promo image with the headline 'Over $1 Billion in Sales' beside a smiling woman in a blue plaid shirt and black cowboy hat.
Promo image with the headline 'Over $1 Billion in Sales' beside a smiling woman in a blue plaid shirt and black cowboy hat.
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.

Heather Sinclair joins Matt Lionetti and The Broke Agent to talk about how she transitioned from hospitality to real estate—and how she became one of the top agents selling ultra-luxury homes in Aspen, Colorado. 

They also cover how she reaches potential clients living outside Aspen, what she’s done for her clients to protect their privacy, and how important agent-to-agent referrals are to her business. 

Heather has been in the business for over 20 years now and has over $1 billion in sales to her name. She shares some stories of experiences with high-profile clients (who shall remain nameless), why they simply call her on her cell phone, and what she does to go the extra mile for them. 

Stay to the end to hear about a particularly memorable horseback ride she took with a celebrity and her friends. 

Click on any of the timestamps below to watch: 

00:0000:57 Intro 

00:57 Meet Heather Sinclair

03:13 How she transitioned from hospitality to real estate 

05:11 How she became the agent everyone in Aspen knows

06:46 How she reaches potential clients outside Aspen 

13:23 Is the Aspen market seasonal—or is it great throughout the year? 

16:15 How hard was it to establish yourself as one of the top agents in the market? 

17:26 You were doing all this while raising twins? 

18:19 Do you have to know skiing to be a successful Aspen Realtor? 

22:00 What’s your lowest listing right now? 

26:30 How important are agent-to-agent referrals to your business? 

29:33 Do you ever get nervous or dress differently around celebrities? 

31:52 Horseback riding with celebrities 

35:31 Do celebrities ever use fake names—and, if so, how does that work?

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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