What is Going On With Boston Real Estate?! | Better Bad Ideas w/Sean OBrien | Ep. 64 @BetterBadIdeas
What is Going On With Boston Real Estate?! | Better Bad Ideas w/Sean OBrien | Ep. 64  @BetterBadIdeas
Uploaded April 2026 | Updated September 2026, 8 hours ago
Sean sits down with super realtor Will Montero to discuss the state of Boston real estate. Special thanks to our Launch Sponsor, Keches Law Group! Visit KechesLaw.com for your legal needs.

This episode is also brought to you by LaborFirst, the leader in healthcare
navigation and advocacy for plan sponsors, union members, and retirees. Visit laborfirst.com for more information.

New episodes of Better Bad Ideas drop every Wednesday! Subscribe and hit the bell to be notified when they go live! Also available where ever you download podcasts!

Chapters
00:00 - Intro
00:20 - Welcome Will Montero
03:13 - How did you get into real estate?
12:51 - The real estate grind
14:45 - Who can actually buy houses these days?
18:03 - What do you think about the commercial market?
22:23 - How will the commercial market impact your business?
23:43 - What are you looking for in leadership in Boston?
25:30 - Rent Control in Boston
31:50 - What is a Broker’s Fee?
36:22 - What will Boston’s Real Estate Market look like in the Future?
39:53 - How to become a first time home buyer
44:48 - Why can’t we create programs to help young people buy homes?
47:45 - How will AI affect real estate agents?
52:08 - The importance of having an agent
55:56 - The new Generation of workers
57:50 - What does your day look like?
59:55 - How does your career affect your personal life?
1:02:10 Where can we find you?
1:04:10 Who would you have lunch with?
1:05:23 Outro

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What is Going On With Boston Real Estate?! | Better Bad Ideas w/Sean O'Brien | Ep. 64

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