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
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.