CRE Broker Playbook with Jake Crandall

Ken Ashley has spent nearly 30 years at Cushman & Wakefield Atlanta, but the conversation that shaped his career happened over breakfast in the mid-90s. In this episode, Ken shares how that breakfast pulled him out of a CFO role and into commercial real estate, and why he's spent the rest of his career trying to repay it.

We dig into the 2009 downturn, when his wife Karen sat him down in tears and told him they were in trouble. Ken walks through the two paths in front of him, the one he chose, and the permanent changes he made to his business afterward, including building a roster of 14 enterprise accounts (with a goal of 20) to smooth out lumpy cash flow.

We also cover:

• His marketing thesis after COVID and why the buddy-call model is dying
• The difference between sales and marketing, and how social media earns him the right to ask senior execs for advice
• Why he stayed at a big shop for three decades and what it actually unlocks
• CREI Summit 2026 in Savannah and the Create Lab content sessions
• His new book, The Prescription, launching March 10th

If you're a CRE broker trying to build a career that survives the next downturn, this one's worth your time.

Ian Stroud, a real estate broker in Indiana, discusses the development and implementation of the CRE operating system he created on Notion. The system serves as a comprehensive business management tool, integrating AI, automation, and email functionality. Ian shares insights on using Notion for personal and business purposes, as well as his tech stack and tools. He also explores the use case for brokers and provides feedback on the system's impact.

Takeaways

• Development of a comprehensive CRE operating system on Notion
• Integration of AI, automation, and email functionality
• Use of Notion for personal and business purposes
• Insights on tech stack and tools
• Use case for brokers and feedback on the system's impact

Chapters

• 00:00 Introduction and Background
• 09:13 Development and Implementation of the System
• 16:29 Use of AI and Automation
• 22:12 Use of Notion for Personal and Business Purposes
• 31:10 Use Case for Brokers and Feedback

The conversation covers the importance of personal branding and authenticity in digital presence, the impact of external factors on business performance, and the significance of networking and relationship building in commercial real estate.

Takeaways

• Personal Branding
• Digital Presence

Chapters

• 00:00 Personal Branding and Authenticity in Digital Presence
• 10:05 Networking and Relationship Building in Commercial Real Estate

Fly Jamerson is a social-media strategist and content creator based in Baton Rouge, Louisiana.

She helps commercial real estate brokers turn everyday deal stories and field insights into high-impact social media content.

The conversation covers topics related to marketing collaboration, content creation, specialization vs. generalization, measuring social media success, content distribution and engagement, analyzing social media performance, social media analytics and business impact, reaching the right audience on social media, and effective content creation and distribution.

The discussion emphasizes the importance of a consistent content creation workflow and the impact of social media on business growth. The conversation covers topics related to translating personal voice into text, calibrating AI to personal style, optimizing content production for time, maximizing social media efficiency, Movo Media Marketing's services, investing in personal business, video and podcast content strategy, and contacting Fly Jamerson for further engagement.

Chapters

* 00:00 Introduction and Marketing Collaboration
* 05:59 Specialization vs. Generalization
* 13:04 Analyzing Social Media Performance
* 18:53 Reaching the Right Audience on Social Media
* 25:11 Consistent Content Creation Workflow
* 31:27 Calibrating AI to Personal Style
* 37:06 Movo Media Marketing's Services
* 43:20 Investing in Personal Business
* 52:26 Contacting Fly Jamerson

If you're a commercial real estate broker and are tired of getting killed by your taxes, then you've come to the right place.

You're an entrepreneur, ever since you started getting paid by 1099, you became a business owner. And now it's time to act like one.

If you'd like to get in touch with us, please reach out at ⁠⁠⁠cre-cfo.com⁠⁠⁠ and fill out the form there. We'll be in touch as soon as we can.

If you're a commercial real estate broker and are tired of getting killed by your taxes, then you've come to the right place.

You're an entrepreneur, ever since you started getting paid by 1099, you became a business owner. And now it's time to act like one.

If you'd like to get in touch with us, please reach out at ⁠⁠⁠cre-cfo.com⁠⁠⁠ and fill out the form there. We'll be in touch as soon as we can.

If you're a commercial real estate broker and are tired of getting killed by your taxes, then you've come to the right place.

You're an entrepreneur, ever since you started getting paid by 1099, you became a business owner. And now it's time to act like one.

If you'd like to get in touch with us, please reach out at ⁠⁠cre-cfo.com⁠⁠ and fill out the form there. We'll be in touch as soon as we can.

If you're a commercial real estate broker and are tired of getting killed by your taxes, then you've come to the right place.

You're an entrepreneur, ever since you started getting paid by 1099, you became a business owner. And now it's time to act like one.

If you'd like to get in touch with us, please reach out at ⁠cre-cfo.com⁠ and fill out the form there. We'll be in touch as soon as we can.

I interview my former professor Anthony Herrera about his career and various ventures into entrepreneurship.

We cover:

- is there value in an accounting degree?

- how do you go about solving accounting talent shortage?

- prioritizing family v business

- executive coaching

Thank you for joining us!