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Over A Pint Marketing Podcast


May 15, 2025

#161 We love talking to folks in the real estate game. And in this episode, Pat has a sit-down with Charlie Hutchinson, who heads up one of the leading real estate teams in the Milwaukee area. 

Great insights into real estate and marketing. 

 

Here’s what we cover: 

 

0:00:00 – Intro 

 Face-to-face setting, Charlie's background tease, chemistry between host and guest.

0:05:00 – Charlie’s Background & Origin Story
From Spanish class and radio to Nashville, and eventually real estate.

0:12:00 – Early Agent Days & Learning by Doing
Living in grandma’s basement, soaking up knowledge at Shore West, hustling for scraps.

0:18:00 – Starting a Team: The Charlie Group to Houseworks Collective
Ego-driven beginnings, learning he's not a great trainer, and pivoting to scalable support.

0:26:00 – Current Market Conditions & Outlook
Thoughts on buying/selling in today’s market, interest rate impacts, and inventory challenges.

0:33:00 – Building Houseworks Collective: Leverage, Support, and Team Structure
Why leverage matters, team roles, and the biggest learnings as a leader.

0:40:00 – Hiring Philosophy & Culture Fit
Self-awareness, using a second perspective, and the danger of liking people too much.

0:44:00 – Marketing: Buyers, Sellers & Agents
Segmenting the audience, introducing the LLC framework: Leads, Leverage, Culture.

0:52:00 – Pricing Strategy & Listing Approach
The psychology of pricing, market nuance, and how comps are really used.

0:58:00 – Social Media Strategy & Personal Branding
Why video is about you, not the house — building agent brand over listing views.

1:03:00 – Skillset of a Great Agent
Reading people, simplifying the agent's role, cutting out busywork.

1:07:00 – Keller Williams Partnership & Merger Strategy
Merger with the Jay Schmidt team, thinking big, scaling through leverage, and support from Keller Williams.

1:15:00 – AI Usage in Real Estate & Team Enablement
How Charlie uses ChatGPT, the need for a team prompt library, idea-sharing culture.

1:21:00 – Misconceptions About Real Estate Careers
“Money flows” myth, helping vs. selling, the long view on building trust and success.

Connect with Charlie on Instagram @charliehutchinson 

Or https://teamhwc.com/

 

Connect with Pat at: pmcgovern@ascedia.com

 

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This podcast is sponsored by Ascedia. A web development and digital strategy agency helping clients win in the digital space.