Charlie Hutchinson: Co-Founder & President of Houseworks Collective
Over A Pint Marketing Podcast · Over A Pint Presents
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Show Notes
#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: [email protected]
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This podcast is sponsored by Ascedia. A web development and digital strategy agency helping clients win in the digital space.