ABOUT THIS EPISODE
In commercial real estate, it’s all about the deal. But what if relationships are the deciding factor in who gets trusted with the deal in the first place?
In this episode of The Wealthy Entrepreneur, host Bob Gauvreau sits down with Ken Ashley, Executive Director at Cushman & Wakefield, to talk about what three decades in commercial real estate have taught him about trust, discipline, responsiveness, and becoming indispensable to clients.
Ken shares one fascinating story after another: how one breakfast changed the direction of his career, why he took a second job valeting cars when he first entered the industry and how he built a long career in a commission-based business where, in his words, he wakes up “unemployed” every morning.
He also breaks down the 70/30 principle for building client trust, the “digital nod” system for staying responsive and the importance of guarding your time from low-payback activities, including the now unforgettable $500 pork sandwich.
This conversation offers a grounded look at how relationships, preparation, follow-up, and real listening can compound into a career that lasts.
If you want to join the conversation and be a part of the Wealthy Entrepreneur community, let us know here: https://www.wealthyentrepreneur.co/the-wealthy-entrepreneur-podcast-guest-submission. Looking forward to having you on the podcast!
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Highlights:
00:00 Introduction and Meeting Ken Ashley
00:32 The Breakfast That Changed Ken’s Career
02:31 There Is No Shame in Starting Small
03:11 Thirty Years Without a Salary
05:43 What a Tenant Representative Actually Does
06:45 Why Real Estate Decisions Can Become Career-Limiting Moves
07:48 Why Ken Wrote The Prescription
10:00 Why Breaking Into Commercial Real Estate Is So Hard
12:05 The 70/30 Principle for Building Trust
14:32 How to Become Indispensable to Clients
17:41 The Digital Nod and Why Responsiveness Matters
19:30 Why Ken Created the CREI Summit
22:40 Building a Practical Battle Plan for Your Career
24:24 The One Habit That Compounded Ken’s Success
25:35 Tactical Listening and the Law of Familiarity
27:10 The Biggest Mistake People Make Entering Real Estate
28:15 Why a Free Lunch Can Cost You $500
29:03 Final Thoughts
About Ken:
Ken Ashley is an Executive Director at Cushman & Wakefield, where he works as a tenant representative helping companies solve complex commercial real estate problems. His work focuses on large tenant representation in Atlanta and portfolio management for companies with multiple leases. With more than 30 years in commercial real estate, Ken has built a career around relationships, responsiveness, and helping clients make better decisions in one of the most significant cost areas of their business.
Ken is also the author of The Prescription, a book created to help young professionals understand commercial real estate, how to enter the industry, and what to do from day one. He is the founder of the CREI Summit, a micro-conference built around commercial real estate influence, content, AI and community.
Connect with Ken:
LinkedIn: http://linkedin.com/in/kenashleyatlanta
Instagram: https://www.instagram.com/kenashley/
X by Twitter: https://x.com/kenashley?s=20
Website: http://www.cushmanwakefield.com/
The Prescription Book: https://www.amazon.com/Prescription-Blueprint-Breaking-Commercial-Multi-Million-Dollar/dp/B0GRWPCW1M
CREI Summit: https://www.creisummit.com
Resources:
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